3 comments/  60402 views/  36 favorites

Jacki's Journey into Sissyhood

By: jacki697



I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like what you see, send me your number and we can set up something, Steve." I sat there in a matching red lace bra and panties and black patent high heels, with my makeup, and my favorite blonde wig on, examining Steve's photos and offer. He certainly had a great body, for a man in his 50's he had a nice flat stomach, with broad shoulders and powerful arms, and just a dusting of dark hair across his chiseled chest. He was quite handsome in an all American guy sort of way, his short cropped hair was peppered with gray hair that continued to his well-manicured goatee. He was differently my type, the daddy/older guy type. I took one last drink of wine and thought to myself it's now or never, and entered in my number and hit send.

I guess I should explain how I got to this point. I had always considered myself a pretty normal guy, but I had a secret. When I had some time alone I loved to cross-dress. I started cross-dressing in college, primarily out of curiosity. I had become a fan of transsexual porn, so for me that kind of morphed into dressing myself. For me, cross-dressing was a sexual experience, I loved to post pictures of me en femme and have men salivate over my feminized body. I felt good to be viewed as a sexual object and be pursued as such. Not to mention how dressing in sexy, and sultry lingerie and women's clothes made me feel about my body. I considered myself straight, and I had many relationships with women, but when I was en femme I fantasized about being with a man. I was always was presented with offers by men to "make a woman out of me" but being too much of a chicken shit I never followed through with them. 

Eventually I met a girl, who I thought was the love of my life, graduated, got married, bought a house with a two car garage, you know the American dream so to speak. I hid my fetish away, and really never thought about it anymore. Then one day I came home early to find my wife of 2 years in bed with both of her business partners. Turns out her little three-way was just one of many the group had been having over the past month, and only one of the 4 affairs she had in the past year. I thought I'd married the perfect girl, only to find out Id married the perfect slut. Oh well, water under the bridge. 

After my divorce was final, I decided a new start was in order. I quit my job and headed for the west coast. 

So there I was in my mid 20's, in a one bedroom apartment, in a new city where I knew virtually no one. It didn't take to long for me to fall back in love with my old perversion. Thanks to my new job and the boatload of money I was bringing home, in about two months I had a girly wardrobe that would rival my ex-wife's. I had procured makeup, several wigs, and even purchased a set of silicone breast forms to complete my look. To help fulfill my sexual desires, I had even begun experimenting with anal play, and had even started a sex toy collection. 

I was always a smaller guy, and was fond of running, and yoga so I kept my body slim and in shape. I was short in stature, about 5'6" in shoes, 5'8-9" in heels. I now kept my body completely shaven except for the hair on my head. 

The only hurdle I hadn't cleared was fulfilling my fantasies. That brings me to the present. I had made a promise to myself to ring in the New Year this year in style and explore my desires. So a couple of days before the New Year's Eve I posted an ad. 

"26 year old crossdresser looking to ring in the New Year in style: My name is Jacki, and I looking for some manly company for New Year's Eve. I'd like to take my fantasies to the next level and want to be taken like a woman for the first time. "

I posted the ad with several pictures of myself in my lingerie and heels, and waited to see what turned up. As you might expect by the next day my mailbox was chock full of responses from men of all types and shapes. I set to work weeding through the numerous dick pics and childish one liners until I had about 5 men's messages singled out and replied to each. Steve was one of those guys. As it turned out Steve was the only of the 5 that lived in a reasonably close proximity, and was quiet attractive so he made the cut. 

After hitting send on my computer, I let of a sigh of relief and finished my glass. I then got up and walked myself into the kitchen to pour me another glass. My cellphone lay on the counter as I began to fill it, when all of a sudden my phone began to vibrate. 

As I looked down at the display, it was an unknown number, which I figured must be Steve. I swiped to answer then help the phone up to my ear and in my most seductive voice I said, "Hello."

"Hi, is this Jacki," a deep manly voice on the other end of the phone replied. 

I answered back, "Yes this is, is this Steve."

"Yes it is darling," he stated.

"Wow, you work quick Steve. You must have been sitting by the computer waiting for my reply."

He laughed, "I was afraid if I didn't act quickly, some other lucky guy might get you first."

I giggled back, "No, Steve, you got dibbs."

We made small talk back in forth for a while, before I asked, "So, would you like to come over and spend New Year's Eve with me tomorrow night?" 

"Absolutely, I'd love to," he asserted. "What time should I come by?"

"How about 10 or so, that will give us time to get acquainted before, we RING in the New Year," I giggled. 

"You got it, I can't wait. Just text me your address later."

We said our goodbyes and I collapsed into my sofa in lustful excitement. I let my hands rub up my silky legs and then pat my ass. "Here, that ass. Tomorrow night you get your cherry popped."

I tried to fall asleep around 11, but couldn't sleep and I tossed and turned all night as images danced in my head. 

The next day flew by, as I need to clean up the house, for company. Before I knew better it was 5 in the afternoon which signified the time for me to start my process. I had been periodically cleaning myself with enemas throughout the day, but I decided on one more before my bath. I filled the bag with lukewarm water and inserted the hose into anus and allowed the water to flow. I held a whole bag and half of another, before having to let it go. The water ran crystal clear signifying my rear was completely clean. 

I had filled the tub with warm water and my favorite bubble bath, and set my radio to Katy Perry new cd and relaxed. As the music played and the warm water relaxed me I used my razor to clean up all the 2 day stubble from my body. When I was convinced I was clean and smooth, I exited the tub and toweled dry. Next came the application of the vanilla scented body lotion which I applied liberally to my skin. The lotion had a little glitter to it giving my smooth skin a girlish luster. 

Setting down at my makeup table, I began sorting through brushes and powders and creams. Starting with primer, then foundation, and followed by blush. Next I curled my lashes, followed by eye shadow and mascara. Lastly came my candy pink lip gloss, I coated my lips and pouted them. I sat back to observe my work. Not bad I thought to myself, somewhere between slut and drag queen, just the look I wanted. I then opened my bottom drawer and retrieved my breast forms and body glue. I carefully applied glue to the back of the forms before slowly placing them on my chest. Once done a little concealer helped blend the edges in. The forms gave me a small D cup chest and really looked great, not to mention had a great feel and weight to them. 

I then went to the closet and began sitting out my outfit. First came my black lace bustier. It was accented with small pink bows and the back featured pink satin ribbon enclosure. The bustier also had garters and a matching lace thong. The thong came first, then I shimmied the bustier up my torso putting my arms through the shoulder straps then tightening the satin ribbons to achieve the desired look. I then retrieved a pair of black sheer stockings from my hosiery drawer. Sliding the first silky stocking up my leg and fastening it caused my clitty to leak precum, causing my to have to stop and clean it up with tissue before it made a mess. Eventually I got the other stocking in place and the lace top attached to the garters of my bustier. For my shoes for the evening I selected my sparkly pink platform pumps from closet and slipped my feet into them. Lastly my blonde shoulder length wig, was settled into place and I brushed and teased the wig to life. 

I stepped in front of my full length mirror to observe my work. Wow Jacki, you really outdid yourself tonight, I thought, as I stared back a young blonde bimbo. My false tits were pressed up nearly to my neck by the bustier and my bubble but look delicious in these heels. "Steve, is a lucky man tonight," I said to myself as I tossed my hair behind my shoulder with my hand. I the put on my black lace robe that covered my ass barely and tied the satin tie around my waste. I sat down at the makeup counter and affixed two gold hoops to my ears, buckled a rhinestone choker around my neck and added a couple of bracelets to each wrist. 

I looked at the clock to check the time, it was 9:15. I checked my phone to see a new text. I opened it: "On the way sexy gurl, be there about 9:50." I smiled, and laughed. I loved being called sexy. I hopped up to leave my room before catching myself. "I almost forgot my most important piece of Jewelry." 

I walked to my night stand where I kept my toy collection and fished out a bottle of lubricant and my glass butt plug with a pink crystal in the base. I crouched down on my heels and pulled my thong to the side exposing my hole. I then dabbed some lube on my fingers before massaging the liquid into my sissy pussy. Grabbing the plug by the base with the other hand I added another drizzle of lube to the tip of the plug. I placed the toy at my entrance and cooed as the cool glass touched my love canal entrance. I slowly applied pressure and the tip began to slide home. I gasped as the 1.5 in toy passed through my inner sphincter and set in place. I rearranged my thong and stood up. The cold glass created quite the sensation against my prostate, causing my clitty to throb and give off juice. I looked down and decided that I'd just place some tissue in my panties to minimize the mess until Steve got here. 

I was finally ready and in just enough time to pregame a bit. I poured myself some wine as I danced in the kitchen to some music. Good thing I had remembered to close the blinds or the neighbors would have gotten a show. As I finished my first glass, I noticed lights outside. I peeked through the blinds to see a black SUV had pulled up outside. A large well-built man stepped out. I thought to myself, its show time. I turned off my music and waited for the knock. 

Eventually there was a rap at the door. I shouted, "Just a minute," as I quickly straightened my outfit, and tossed my hair about. The clack of my heels on the hardwood followed me to the door. I reached to the door knob and opened it. 

As the door swung opened it revealed a hunk of a man, in a grey suit jacket and pants, and navy blue dress shirt. He was extremely handsome, and the pictures didn't do him justice. 

"Wow, you look incredible. Looks like I won the lottery," he said as he stood in the door way gawking. 

"Oh stop," I retorted blushingly. 

"You must be Steve, come in, ... come in, " I insisted motioning with my hand. 

Steve stepped inside and wrapped his left arm around me in a hug, "Wow Jacki, I think you smell as lovely as you look darling."

He released me from his strong embrace and I shut the door, "Well I'm glad you're pleased with the product."

"You could easily pass for a woman, hell any guy would be lucky to be here."

I smiled back, "You are two kind."

Steve lifted his right arm displaying a bottle of wine and champagne. "I brought you a present," he said with a wolfish grin. 

"Well you sure do know the way to a gurl's heart, or panties," I laughed. 

We laughed and talked and drank like old friends. Steve was really easy to talk to. In fact his story was similar to mine, he was divorced 10 years, after he found his wife cheating on him as well. We talked about our lives and fantasies, and drank some more. Before long we had drained the bottle of wine he had brought and finished off one that I had as well. Any inhibitions that I had were now long gone. 

We were having so much fun we almost missed the countdown. Steve quickly poured us a glass of champagne and handed me mine as the countdown started. We chanted in unison, "8, 7, 6, 5, 4, 3, 2, 1, Happy New Year."

I then felt Steve's hand on the small of my back and he quickly spun me around and planted a deep passionate kiss on my pink lips. I melted into his embrace and lustfully returned his kiss. We finally broke, "I'm sorry, I just couldn't take it anymore I had to kiss you," he apologized. 

"No, No I'm glad you did," I assured him as I smiled back. I then initiated a kiss and this time it was quite a bit hotter. Our lips met and our tongues explored each other's mouths. Steve's hands began to explore my body and he began softly kneading my firm ass. 

I finally pulled away and purred into Steve's ear, "I think I'm ready to take this to the bedroom, I'll go get it ready you stay here, I'll call you when I'm ready." 

This time Steve didn't answer, he just nodded yes. I spun around and walked myself to the bedroom. I shut the door behind me, then lit the candles on my nightstands and my dresser. I then turned the radio over to some R&B music, or baby making music as I used to call it, and turned out the light. When I was satisfied I had set the mood, I opened the door and gave Steve my best "come here big boy", and watched him sprint to my door. I grabbed him by the hand and led him into my chambers. He then pulled me close as and kissed me again. 

Our tongues pushed against each other's as Steve untied my robe and I lifted his shirt of his rock hard body. We broke our mouth to mouth lock long enough to release the garments and then we were back at it as Steve groped my now exposed butt flesh. I fondled the growing bulge in the front of Steve's pants before I finally couldn't take it anymore. I dropped to my knees in front of Steve, and seductively unbuckled his belt. I looked up into his eyes biting my lips as he stared down in lust. I buttoned his pants and let them fall to the floor, revealing a pair of black silk boxers. I then hooked my thumbs under the elastic of his waist band and forced them downwards. As the slid down his skin all of a sudden his hardening member sprung free nearly hitting me in the face. I gawked at it in all its manly glory. Steve's penis was at least 7 inches long at this point, and a good 2 inches thick with a perfectly shaped pink head. Accompanying the shaft might have been the biggest set of balls I'd ever seen, like golf ball big. This was the first time I'd seen a man's package up this close in all its glory, and it was beautiful. I glanced up at Steve in amazement. He laughed, "Go ahead baby he won't bite."

I raised my hand and caressed his silky shaft before grasping the shaft and slowly stroking his manhood. I was amazed how silky and soft it was as my hand moved back and forth over the stiffening rod. My mouth was beginning to water as I anticipated the first taste of cock. I stuck my lounge out as my hand guided the shaft towards its target. I flicked the tip tasting his salty precum, and felt his cock jump in my hand. I then swirled my tongue around his massive head as I had girls do to me as I heard Steve let out a moan. Finally to widened my lips and began inserting his dick into my mouth, before closing my lips securely around the head to savor the taste. It's hard to describe the taste, but it was like the first time I had a really good steak, I knew it was delicious and it definitely wouldn't be my last. 

Next I began working his penis in and out of my warm wet mouth, and using my tongue to bath the underside of the shaft. I worked his rod in and out a few times, as Steve rocked back and forth, before removing his cock and licking the shaft and the head liberally. I then returned his now swollen tool to my moist hole and allowed Steve to slowly move his cock in and out as he pleased, as my tongue probed his piss slit. I worked my hand furiously jacking his exposed shaft as he drove his cock deeper and deeper with each thrust. Steve then placed his hand on the back of my head and drove cock ever deeper. With each invasion I concentrated on swallowing as much as I could. Before long Steve pushed his entire cock down my throat and held it there as my nose was buried into his neatly trimmed pubic mound. The sensation wasn't unpleasant as I thought it might be, as I calmly breathed through my nose. 

Steve finally let me go and I removed my mouth from his sword. "Did I do good, Daddy," I giggled. 

"Yes baby gurl, that was amazing," he answered as he pulled me to my feet. He kissed me deeply and lifted me to my feet, before sweeping my up in the muscular arms and laying me down on the bed. He then climbed on top of me lording over me as we kissed. Steve's hands explored my body. He caressed the silicone orbs on my chest playing with them like a real pair of breasts, with one hand; the other caressed my stocking clad legs up to my ass. After a bit his hand began to touch my clitty, before I stopped him. "No daddy, please don't play with my clitty. Treat me just like a girl tonight." 

"Of course baby, I'll make you into a real woman tonight." 

He kissed me once more on the lips before moving to my neck with his kisses. I moaned as he kissed me, and I stroked his now rock hard cock with my free hand. Steve slowly slid down my body with his kisses, before stopping and lifting my legs, and exposing my nubile ass. He softly kissing my smooth bottom as I grabbed my legs and pulling them into my chest. Steve pushed my thong to the side saying, "What do we have here," as he rotated and tugged at my glass ass stopper. 

"That's your present daddy, I hope you like it," I cooed.

He replied, "That's sexy as hell baby girl."

Steve then firmly began to tug on the plugs base, as I moaned, "Oh, Daddy!!"

My anus could no longer hold the plus in and the plug came free with a loud "pop." My ass jumped as the glass stopper came free. Steve the inserted the plug bulb into his mouth tasting my ass as he moaned, "Um, baby girls hole is nice and fresh for Daddy. It tastes so good."

Steve sat the plug aside as he then turned his attention to my virgin bud. His tongue flicked at my opening lightly as my hole pulsed. I cooed as his wet tongue began to lap at my sissy pussy. My eyes rolled back into my head as Steve put his ass licking skills to work. 

"Oh, yes that's it. Lick that pussy Daddy," I whimpered as Steve's tongue danced at my love hole. This was obviously not the first ass he had licked. As his wet tool assaulted my pussy, my clitty now had a stream of continuous fluid leaking from the head onto my lace covered stomach. I began to breath heavy and was nearly at the edge of climax just from the Steve's tongue. 

I finally couldn't take it anymore and shouted in lust, "Fuck me daddy, please, give me your cock. Take me now!!"

Steve looked up from his work, with lust in his eyes. He was quickly to his knees and grabbed a pillow from the other side of the bed and inserted it under my hips lifting and exposing my ass. I then handed him a bottle of lube that he squirted a generous amount into his hand then some more into my ass. The slicked up his man meat with one hand and spread the lube into my pussy with the other. 


Jacki's Journey into Sissyhood Pt. 02



This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. 

*****

I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from under Steve's arm, only to have him pull me closer and kiss my shoulder. "Good morning Jacki," Steve said sleepily as he yawned. 

I took my free hand and grasped his erection, and laughed," It seems this guy has been up for a while now."

He chuckled back, "Yeah, well who can blame him he's next to such a hot piece of ass." 

"He does have good taste in gurls I guess, and he tastes good too."

We both laughed for a minute and then I rolled over and kissed Steve good morning. "Well I'm guessing you will be leaving me soon," I pouted. 

Steve glanced at the clock, "yeah I need to head out in a minute."

"You have time to do something with that erection," I questioned.

"I figured you're too sore for that this morning."

I answered, "Well I am pretty sore down there, but how about a blow job instead."

"I've never been a man to turn down a blow job."

I peeled back the blankets to reveal his stiff member cloaked in his boxers. I peeled down his boxers and set to work. This time I attacked his prick, quickly swallowing it and coating it in saliva. I used my hand one hand to work his shaft and the other to fondle his balls, while I bobbed up and down on the shaft. 

"You are cock hungry little slut this morning aren't you," Steve asked. 

I managed to gurgle out a, "yes Daddy," with his dick in my mouth. 

He laughed me on and began to moan slightly as I continued milking a load from his cock. I then pulled his cock out of my mouth and began sucking on his testicles. He sighed through his teeth, "That's it you dirty girls, such Daddy's balls." 

Spurred by his encouragement I rolled each testicle about in my mouth as my hand furiously worked his shaft. After thorough tongue bathing his sack I returned the attention back to his shaft and licked it from base to tip before returning it to my mouth. 

After of couple of minutes I felt Steve's cock pulse, and I knew he was close. He smiled and moaned, "Is daddy's gurl ready for breakfast?"

Once again I murmured, "Yes daddy," as I worked his tool. A few seconds later, I felt Steve raise his hips and moan, "OH god, baby I'm cumming."

His cock then began to spasm and launch ropes of thick warm seed into my throat. I tried to swallow as much as could, but there was once again a lot to deal with. Some of his delicious nectar began to leak out. 

I looked up at Steve as I released his cock and choked down the mouthful of his baby batter. As I swallowed he protested, "Looks like you made a mess, you need to clean daddy up." 

I returned to Steve's crotch and began to tongue up all the spilt jizz from his cock and balls. Once he was satisfied he tapped me on the head and said, "Good gurl, you learn pretty quick."

"Thank you Daddy," was my reply. 

"Listen I'm going to use your shower to get cleaned up, why don't you make me a cup of coffee for the road."

"I'd love too," I answered. 

Steve disappeared into the bathroom and the water began to run. I scampered into the kitchen and began preparing his coffee. 

About the time the coffee pot was done, I heard the shower shut off. I yelled through the door, "How do you take your coffee."

"Two sugars," was the reply. 

I returned to the kitchen, and found an old travel mug of mine. Filled the cup then added the sugar and fastened the lid. As I finished up, Steve emerged from the bedroom. 

"Great the coffees done." He walked up behind me and smacked my panty clad ass, which made me jump. He grabbed the cup, and said, "Thanks baby, I really got to run. Last night was incredible, and I've got your number so I call or text you later in the week Ok."

I nodded, "Ok sounds good." Steve kissed me once more and then was out the door. 

I stood alone in my living room, still dressed in my babydoll from last night, and my wig, with a butt plug in my ass containing a wad of a strange man's cum in my butt. I probably should have been embarrassed with myself but strangely I was a little proud. 

Before hand when I crossdressed it was simply about my sexual release, primarily achieved through me masturbating. However last night I hadn't even touched my dick. I had an orgasm, a powerful one, but it felt different. After my sexual release when I jacked off, I often lost my sexual desire and often felt ashamed. But my sexual release last night from my deflowering just made me hornier. 

And frankly I didn't particularly care about my pleasure as much as I cared about pleasing Steve. It was a revelation for me. I don't know what he knocked loose inside of me with his cock, but I did know this wouldn't be my last gurly experience I was hooked. 

The rest of the week went by pretty quickly for me. I was busy at work and had to work long hours. Thursday rolled around and I began wondering if Steve was ever going to call back. That evening I got off early than I had all week, I swung by the gym for a run, then came home for a little me time. I ran a bath and grabbed a glass of wine and set to relax. As soon as I got into the tub, my phone began to ring. 

I looked at the number, it was Steve. I answered quickly, "Hi there, I was beginning to think you were never gonna call back."

"It's been a long week sweetie, but all is ok. How was your week?"

"Busy and long," I laughed.

"Well listen, I was wondering if you would like to come to my place for dinner tomorrow night."

"Sounds lovely," I replied. "Can I come and get ready at your place early?"

"Why don't you just get dressed at your place, I'm sure you have a cocktail dress or something you could wear then you could pack an outfit for later," Steve insisted.

I stammered back, "But I never, have been out before."

"Listen you could easily pass, plus it's not like you are going to be out. Just in your car till you get here. I really want you to come, I have a little surprise for you."

I finally reluctantly agreed, "Ok, if that's what you want. What time?"

"How about 9. I'll text you later with address." Steve said his goodbye and then was gone. I sat there soaking in the tub in the tub and sipping my wine. What had I gotten myself into, a week ago, I was just a curious crossdresser who wouldn't have dared to venture outside. Now here I was about to drive myself across town to a man's house to be his sex toy for the evening. Somehow that felt good, I felt proud of that. 

The next day crawled by, as I was constantly watching the clock. I was able to get all my work done, and was able to scoot out of the office before 5. I stopped on the way home and filled up my car, so I wouldn't have to do it later, and then flew home. 

I jumped into the shower and set to work with my razor. Shaving every nook and cranny in effort to remove any stubble, then washed my body thoroughly. I began my booty clean out process as well. After releasing my first enema, I sat to work on my face. I tried my best, yet alas I still ended up looking like a streetwalker. I attached my breastforms to my chest, then ran my second enema. 

I then combed through my closet, trying to find something to wear. I finally settled on a green dress, it had wide shoulder straps that lead to a plunge neck cut with a pleated skirt, and was adorned with little polka dots. I grabbed a pair of matching green thong panties and bra. I quickly put the undergarments and applied my body lotion, before running my third enema. I was now clean down there and ready to finish my transformation. I stepped into the dress and drew it up my body. After some work I got the dress in place, and twisted myself around and was able to work up the zipper. Next came my white peep toe pumps. Lastly came my wig. Once finished I stood in front of the mirror and tugged and straightened until I was satisfied with my image.  

I grabbed a bag from, and filled it with assorted lingerie, panties, stockings and my black patent pumps. I grabbed my phone to see I had a text message from Steve, "Make sure you bring your plug for tonight." I smiled and laughed to myself, "I guess he plans on filling me up again."

By that time it was 8:30, and time for me to get on the road. I looked through the blinds to make sure there weren't a lot of people out and about. It was dark now and not many were out, so I cracked the door and peered out into the breezeway. I looked both ways a couple of times, took a deep breath, and then made the break for it. I scampered to the car as quickly as I could manage in my heels. When I reached the car and closed the door behind me I finally let out my breath. I started the car and was off. 

I followed the directions on my phone and made my way across town, and quickly made it to Steve's neighborhood. I hadn't ventured to this side of town before and was quite shocked at the massive sprawling houses that lined each side of the boulevard. This must be the nice side of town, check that the really nice side of town. I followed the GPS directions, and before long the voice told me to turn left, and then you have reached your destination. I picked up my phone and checked it again, "This can't be right," I thought out loud. 

I was sitting in a private driveway, starring at a large wrought iron gate. Next to the window there was a keypad, and speaker. A rolled down the window and pressed the call button. There was a loud buzz, then the gates began to swing open. Guess this is the right place. 

As I drove up the drive I noticed the size of the estate, the front lawn was expansive and expertly kept. The long driveway led to a large circle in front of a Spanish style villa, the front lights were on and a familiar figure stood on the veranda. I pulled up the circle and parked before shutting off the engine. Before I could manage it, Steve opened up my door and offered me his hand. I took his hand as he helped me exit. "I was worried you might have trouble finding the place," he remarked. 

"No trouble, GPS took me wright to it actually. I've never been over this far. This is so beautiful out here."

He smiled and said, "Not quite as beautiful as you look tonight."

"Oh stop," I blushed as I retrieved my bag from the car. 

Steve took my hand again and led me into his home. He opened the massive front door into a large front room, with high ceilings, travertine floor and bright plaster walls. On the far side of the room there was a large set of glass doors that looked out over a pool and garden. 

"What do you think," Steve questioned as we walked.

"I'm thinking this is the nicest house I've ever been in," I laughed. "What do you do for a living again."

We talked as he guided me around his home, and he showed me no less than 10 different bedrooms. As it turns out Steve had become quite successful in the construction industry after his divorce and due to lucky investments he had turned that success into a large fortune. He only continued to work because he enjoyed it. "Must be nice," I commented. 

As we walked the expansive halls, he turned to me and asked, "Enough of the tour, How about some dinner?"

"Sounds great," I replied. 

Steve led me to a small formal dining room, with a small table set for three. I looked at Steve and nervously questioned, "Are we expecting someone else?"

"Well that's the surprise you see. My girlfriend Laura will be joining us in a minute."

I protested, "But I thought, I mean I'm not ready, I mean what if she knows, she could out me."

"Easy there darling, everything is going to be fine," Steve comforted. "Me and Laura have an open relationship, we are swingers. You do know what swingers are?"

"Yes," I nodded in acknowledgement.

"Well see Laura really wanted to meet you, after I talked so glowingly about you. She allows me to indulge in my sexual desire for sissy girls such as yourself, but occasionally likes to join in on the fun if everyone agrees."

I once again nodded in agreement.

"Listen after dinner, you make the call on whether or not you would like to stay and go further. No hard feelings either way, Ok."

I nodded Ok, and we began dinner. I was quite, and a little nervous but the flowing wine helped to relax me. Eventually the door opened, and in stepped a gorgeous middle aged women. Laura was about my size 5'6" or so 130lbs with long muscular legs. Her red hair framed her face perfectly and draped down onto her shoulders. She wore a gold sling dress, which hugged her figure. Like Steve she was in impeccable shape and her curvy figure was highlighted by her large DD breasts and firm hips and ass. She glided into the room, "This must be Jacki the gurl Stevey can't quit babbling about."

"Yes ma'am," I answered coyly as I extended my hand. 

"Oh call me Laura," she insisted. "Stand up so I can have a better look," as she helped me to my feet. I stood deathly still as Laura walked around and examined me. She must have sensed my angst and touched me on the arm and said, "Relax darling, you are just trembling."

She turned to Steve and remarked, "I must say not bad, and like you told me with a little work she could be a stunner."

Laura then returned her attention to me, "Other than the makeup, the manly shoulders, atom's apple, and god awful wig, she could pass."

I thought to myself, "But I like my wig," as I twirled my fake blonde locks. 

We resumed dinner and continued the small talk. I began to loosen up as the wine erased my cautiousness. After we were finished dinner Steve collected the plates and turned to Laura, "Why don't you propose our idea to Jacki?"

"Ok dear," she smile back at him. 

"What idea," I questioned. 

"Well we have a proposal for you," Laura added as she looked deep into my eyes. "Steve and I are in an open relationship, do you know what that means?"

"Yeah he explained it some, you guys can sleep around a bit."

"A bit might be an understatement dear," she laughed. "We lead a pretty active swinger lifestyle, we sleep around and do as we please basically. However Steve also likes playing around with sissy girls from time to time. I'm fine with his fetish, but I don't like the secretive and unsafe nature of some of his rendezvous. When he told me about you and your potential, we began to discuss the possibility of you becoming our sissy."

I interrupted, "What do you mean potential."

"Well sweetie, I must commend you on the work you've done by yourself. But to be honest you just look like a man dressing like a woman. Your makeup is all wrong and your figure although well disguised gives you away. But don't worry those are things that we can work on should you choose to."

"Oh ok I see what you mean, I definitely could use some help and assistance in some areas, also what did you imply by our sissy," in enquired. 

Laura smiled and said, "Well we, Steve and I, were wondering if you would consider moving in here with us. We have a pool house that you could stay in, rent free and I could help further your feminization. Steve would pay for everything, you wouldn't be out anything but your time. During the day I will coach you, and at night or special occasions you will share our bed. The only stipulation would be that you would live as a woman or stay in dress the entirety of your stay with us, and you will take no other lovers, male or female, without clearing it with us. How does that sound."

"What about my job, and stuff, I can't be expected to be in dress in front of my co-workers," I questioned.

"We had already considered that. If I'm correct, you told Steve you worked as an accountant, am I correct?"

"Yes that's right," I replied

Laura looked pleased and said, "Well I run a small personal training business here, just a couple of clients really, and Steve could always use an extra hand keeping up with things. You could work from here essentially. We would set up a savings account in your name and deposit your salary into that. As I said before you wouldn't need to touch that account during your time here, as Steve would pay for everything else."

I pondered over the situation in as I sipped my glass. I then asked Laura, "That's a very tempting offer, but I have another question. It's fairly obvious what Steve would get from this arrangement but why would you agree to it."

"I thought you'd never ask honey," she joked. "Well, I guess I would start with that I have a dominant side that I've kept pent up over the years. Steve, has a dominant personality, and two doms in the classroom don't exactly mix. So inside of the bedroom, you would be my outlet for that energy. Outside of the bedroom, I could really use a girlfriend to go get my nails done, layout by the pool with, go shopping with. It's been difficult for me to make friends because A, women of my age are either jealous of my body, or aren't excepting of my lifestyle; and B, younger women just try and undermine me with Steve so they can get at his money."

"Have you ever done anything like this before," I questioned. 

Laura answered, "No not with a sissy, we tried with a younger woman but it ended in flames. That's when a swinger couple we know suggested training a sissy. Karen, our friend, has been sending me things about how they recruited and trained theirs. It peaked my interest, so Steve and I decided to try it."

"I see," I added as I pondered the information I had been presented with. "It's a lot to take in, I have to say that your offer does intrigue me but I'm unsure if it's for me."

"Oh darling, No, we didn't expect you to make the decision tonight. This is a big decision for you, take your time and when you're ready let us know. No hard feelings either way, yes or no, Ok."

I sighed a breath of relief and nodded Ok. 

"Enough of this talk, let's have some fun, why don't we," Laura insisted as she stood up grabbing her wine glass. 

"Yes lets," I agreed grabbing my glass and joining her. 

We clanked our glasses and downed them. Laura grabbed my overnight bag and my hand in the other and said to me, "Let's take this party elsewhere."

She led me down a long darkened hallway, as the click clack of our heels echoed off the tile. Eventually we came to two large wooden doors. Laura opened the doors, and turned to me and laughed, "And this is where the magic happens."

We stepped into a softly lit bedroom, with a giant 4 post bed that dominated the center of the room. It was the largest bed I'd ever seen, easily able to accommodate 10 people. Laura led me to the side and into the entrance to their dual walk in closets. On the either side of the corridor that separated the closet there was a sitting area with a mirror. Further down the corridor it opened up into a luxurious master bath. Laura tapped me on the ass with a firm hand and said, "Take a seat and let's get started." She motioned to one of the stools in front of the vanity's I sat down as commanded and Laura drug her stool close to mine. 

"Now off with this dirty wig off, and see what I have to work with," she remarked as she removed my blonde wig and let it fall to the floor. I kept my hair usually cut close, but I had missed a couple of haircuts and my brunette hair was longer than usual. Laura ran her fingers through it saying, "Yes, yes this will look quite cute when I'm done with it."

Laura handed me a wet washcloth and instructed me to scrub my makeup off, while she gathered some things. I found out later that before she had met Steve, Laura was a hairdresser and cosmetologist. So I was in good hands. When she returned with scissors and blow dryers and all types of hair product. She then set herself to cutting, clipping and shaping my hair into a more feminine style. Afterward she began applying makeup to my face, she brushed and blended until she was satisfied with the final look. She spun me around on my stool and said, "Now that's more like. How do you like it?"




Jacki's Journey into Sissyhood Pt. 02



"Wow, that is amazing," I exclaimed as I starred at a feminine young goddess in the mirror. I saw what she had meant about my makeup job, this was totally different. It wasn't too heavy, but lite and fresh. The transformation was made perfect by the new styling of my dark hair. It was a hip, young luck, kind of punk-rockerish but was quite cute. "I love my hair."

"Yes much better than that cheap mop you were wearing," she laughed.

As much as I loved my blonde wig, I had to agree with Laura, this was much better. 

"Now that's out of the way, on to the outfit," Laura noted as she started digging through my bag. "No, no, no, oh the shoes are cute, no on these things. The butt plug and the shoes will work." She turned to me and told me, "Stand up dear."

I stood up as she twirled me around, "yes, I have something I think will work." She disappeared into her closet, on to return a few minutes later carrying some clothes. She dumped the things on her vanity and then held up a hot pink, vinyl overbust corset. 

"Have you ever worn a corset before," she enquired as she sized me up. 

I shook my head, "no." 

"That's fine I can help you get into it quickly, so strip out of that dress and bra," she commanded. I hesitated a second, and she laughed, "Don't be bashful, I'm going to see it all anyway."

Upon her encouragement, I quickly let my dress fall to the floor, then unhooked my bra setting my breastforms free. She squeezed on of the false tits, making a disapproving face, "These really don't work on you, but they will have to do for now."

She then unclasped the corset and draped it around my body as she instructed me, "Start fastening the clasp from the bottom up." 

I followed her instructions, fastening each steel clasp bottom up until they were all done. She then tugged the corset into place, and stuffed my silicone tits down at the top, and motioned for to sit. I sat on the stool in front of her, holding the top in place as she had wanted. I was the instructed, "Now take a deep breath and hold it." As I did she began pulling on the laces of the back of the corset, tightening the fabric against my body. She tightened and tightened, and then tightened some more. The vinyl material and steel ribs of the corset compressed and reshaped my torso. It felt as if all my organs were being squashed together. Eventually, Laura tied off the laces, and told me, "Now breathe out." 

I did as I was told, but found it incredibly hard to get another breath. Laura place her hand on my bare shoulder and said, "Breath slowly in through your mouth and out through your nose." I followed her instructions and was able to regain my composure. 

She laughed, "You'll get used to it I promise." She then handed me a matching pink thong, and a pair of white fishnet stockings. "You can handle it from here, I need to get myself ready, oh and just wear your white peep toes you have on with that outfit." She motioned me out into the bedroom and told me, "get ready in here, I'll be out in a minute." 

I carried my things into the bedroom and laid them out. I started by trying to take my green thong off, only to find I was unable to bend at the waist in the constricting garment. I finally figured it out and wiggled the thong off. I then stepped into the pink thong that Laura had given me, I squatted down and drug the satin thong into place. It just barely covered my clitty and was little more than two strings running up my ass crack. Next came the stockings, which took some imagination on my part. I stood up and placed my foot on the bench at the foot of the bed, from there I was able to draw each fishnet stocking up and fasten the garters. Holding onto one of the bed posts, I then stepped back into my heels. 

"What a sexy sissy slut you make," Laura called from behind me. I spun around to face Laura wearing a purple, open bust corset. Her massive tits hung free, unsupported. She obviously had some work done, as they didn't sage but just sat on her chest and bounced with her every movement. Her plump nipples were pierced with metals bars that caused them to glisten. She wore black fishnets stockings and high heels, with a large strap on dildo fastened across her pussy."

"I think that might fit you better than it does me," she joked. She moved across the room towards me as my eyes were affixed on the large rubber phallus, she wore. She came up to me and kissed me firmly, sticking her tongue down my throat. I returned her kiss as her manicured hand dug into my exposed ass cheeks. "Where is Steve," I protested. 

Laura kissed me again, and said, "He told me what a good fuck you were, so I thought I give you a test drive before he joins us." She licked her lips and looked at me lustfully, "why don't you show off your cocksucking skills, on my friend down here," while she shook the fake cock with her hand. 

She placed her hand on my shoulder and commanded, "On your knees."

I lowered myself to my knees and took the dildo into my hand. From this angle I could see that while one end of the cock was in my hand, another end was firmly inserted in Laura's juicy cunt. I looked up at Laura as I began sucking the shaft of her toy. She moaned and sighed, "Good girl, Jacki." 

I covered the shaft in saliva and then used my hand to milk the shaft as I bobbed up and down on the shaft, as I had done on Steve's cock. "Well, aren't you just a cock loving slut," Laura chided as I made love to her strap on. 

After a minute or two, I guess Laura became bored, and pulled the cock from my mouth, "Steve said you can take all of him in your mouth, let's see if you can deep throat this." She grabbed my head and held it still and drove her tool into my mouth. I swallowed as much as I could but her speed and length made me choke with about an inch of shaft left. "Not quite, but we can work on that."

"Enough of that, let's see how well you fuck," she insisted as she pointed to the bed. "On your back sissy bitch."

I hopped to my feet and moved quickly to the bed, and laid down as instructed. Laura grabbed a bottle of lube from the dresser and followed me onto the bed, taking her place between my legs. She greased her rubber cock saying, "Legs up, grab your heels." 

I grabbed my heels and pulled my legs to my chest exposing my ass to Laura. She pulled aside the pink cloth string, and massaged my hole. "What a pretty pink pussy you have sissy. You want me to fuck your slut ass with my big cock Jacki?"

"Yes fuck me Laura," I answered.

My response was followed by a swift smack of my ass, "No, sissy in here, I am Mistress," she jeered angrily, then swatted my bare bottom again. 

I jumped and yelped at her smack, "Yes, Mistress."

She then lined up the fake phallus with my hole and pushed into me. Steve had been slow and easy, Laura was anything but. As soon as the head cleared my sphincter she buried the cock in my pussy. My eyes watered and I gasped in gain, "Oh shit, that hurt."

My tears, had little effect, as she immediately withdrew the strap on and slammed back into me laughing as she did so. Laura continued her strokes as my ass throbbed around the dildo. As she worked herself in and out she began to moan as the other end of the strap on stimulated her pussy. The pain in my ass began to yield to the pleasure of the cock stimulating my prostate, and I too began to moan. My cries of satisfaction, caused a lustful smirk to appear on Laura's face. "I knew you were a cockloving sissy at heart, tell me how bad you need mistresses' cock."

"Oh god, that's it, your cock feels so good mistress. Fuck my pussy harder mistress. Please fuck me," I pleaded. 

Either her clitoral stimulation or my cries cause her speed to increase, as she continued pounding me. In and out, in and out; faster and faster she went as the replica penis probed my bowels. All of sudden she shuddered and slammed into me, and shouted, "Oh yessssssssssssssss, I'm cumminnggggg!!" She collapsed as her body conversed in orgasmic bliss. 

Laura gathered her composure, and removed the phallus from me. I objected as my now empty pussy throbbed for cock, but Laura laid down beside me and said, "Time to put the pretty mouth back to work."

"Yes mistress," I replied, then crawled between my legs. 

"Clean up my toy, first." She harassed as she waved the cock in my face. I returned to sucking and cleaning the rubber dick, tasting my ass in the process. To my surprise I tasted good, and I happily lapped at the dildo. Laura unhooked the harness, and slid the strap on from her vagina. She then stuck that end into my mouth, giving me the first taste of pussy in over a year. Her scent was primal, and strong, and her taste mellow and smooth. I greedily lapped at the pussy stick till it was cleaned thoroughly. She sat the strap on aside, "now make me cum again," she said and tapped her pussy. 

"That was the only instruction needed and I dove in lapping her labia like a dog, she cooed and groaned. I felt her hand grab my head and then jam my face into her sex. My nose dug into her pubic mound and my tongue fought at her clitoris. She moaned and began grinding her hips into my motions. I looked up at her lost in ecstasy. Laura then looked up and motioned to someone else in the room to join us. I never lifted my head as to keep with my task to make her cum, but crawled to my knees and lifted my ass into the air, as the bed undulated and the visitor climbed aboard. 

"She's such a good slut isn't she, her hole is nice and ready for you just slide right in baby," Laura instructed the stranger. I then felt two large hands on my hips and the familiar feeling of Steve's hard cock at my love canal entrance. My earlier fuck session with Laura had indeed loosen up my tight pussy, as Steve pushed is meat into my rear completely. 

"Oh god, yes," I muttered into Laura's pussy, while Steve began fucking my hole with his rod. We continued fucking and licking in ecstasy for several minutes. My tongues gyrations on Laura's button began to bring her close, she threw her head back and moaned loudly, and her hand kneaded and teased her nipples. His girlfriends cried of joy, kicked Steve into high gear, his trusts quickened and his balls began smacking my taint. The motion of Steve's cock sent me over the edge first, sending ropes of cum from my clitty, and began to drip down as the satin G-string did little to contain it. As my ass orgasmed, I sucked hard at Laura's clit, sending her into a second orgasm. The spasms of Laura's body, caused Steve to grunt then bury his sword, and began spilling his seed into my sissy pussy. 

We froze in that position as our heads slowly stopped spinning. Laura broke the silence, "Holy god, that was intense." We all laughed in agreement. She then looked at Steve over my shoulder, "Did you cum in Jacki?" 

I interrupted, "Yeah, like a fire hose." We all giggled as she grabbed my butt plug from the night stand, "Here you go honey, plug her pussy so she has something to take home." Steve took the plug, removed his cock and inserted it into place. He tapped my ass, "There you go, baby. We will let that cum incubate in there for a bit."

We all collapsed on the bed in our post sex stupor, and laughed and talked. Apparently Steve had been in the room for pretty much the whole session, I had just been so focused on making Laura happy that I didn't notice. 

"Well Laura, what do you think? Did she pass the test," Steve asked. 

"With flying fucking colors, babe," Laura exclaimed. I blushed as the two gushed over me. 

After a while we climbed out of bed, as it was early in the a.m. now, and I needed to get home. Laura told me to keep the clothes as a gift. Since it was so late, and I was too tired to change, I borrowed a mini skirt from Laura to cover my ass gathered my things and headed out. 

Laura walked me out, putting her phone number in my phone along the way. She told me as I loaded my bag into my car, "No pressure, but I'm really excited about where this could go, I think you really enjoyed yourself tonight," as I nodded in agreement, "well I know we did to. Thank over our offer, and when you're ready, call me and we can talk."

"Ok, Laura, I will," I replied. 

We kissed passionately goodbye and I made my way home. 

My drive was a blur, as my mind danced with images of the night and the offer at hand. I had never intended on becoming a woman or a sissy, I quite enjoyed my old life as a man. But I had just had two of the most powerful sexual experiences of my life, like mind alerting sex, as a woman essentially. My mind was so preoccupied that I never even thought to look around the apartment complex before walking to my apartment. I was still wrapped up in post sex euphoria. 

I closed the door to my small one bedroom flat, and it seemed emptier, bleaker than it had before. I set down at the table, to hear a "rap" as my crystal plug touched the wooden chair. It reminded me that I was still carrying Steve's payload. I had to see my trophy for the night, I placed a bowl on the floor and squatted above the saucer and removed my plug, pushing the large glob of jizz from my rear. The cum splashed into the container. Once I was empty I picked it up. The bowl now contained about a quarter of a cup of still warm jizz, from my sex partner. There was never a better sign that I was now a sissy slut forever.



Jacki's Journey into Sissyhood Pt. 03



This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. 

*****

I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I going to surrender totally to my feminine desires? Could I really give up my male life, based solely on sexual release? What would people think? 

Well I had surrendered to them with Steve and Laura, and it had led to the best sex id ever had, as a woman!

With Steve and Laura I had felt really comfortable, like I could truly be myself. They had helped open up my eyes to new things, and I was comfortable with them.

Who did I have to disappoint? I was no longer married, and I sure didn't care what my ex-wife had to say. I had no children, no family to object to my lifestyle. Really there was only one other person that I cared about and valued there opinion. 

My friend Sarah and I grew up together. She was quite pretty, but she was the Tomboy of the school and played basketball, softball and ran cross country. We were pretty close throughout school, and I was the first person she came out to as a lesbian. When I got married, she objected adamantly. Turns out she was a much better judge of character than I was. After my divorce we talked fairly regularly, and if anyone could understand my predicament she could. 

I picked up my phone and dialed her number. 

We talked for a while about normal stuff and laughed a bit, then I dropped the bomb. I explained that I had been crossdressing, I rambled on about my New Year's Eve tryst with Steve, the threesome with Laura and Steve, and then the offer itself. I ended my plea for help with, "I don't know what to do, I'm so torn, help me Sarah."

There was silence on the other side of the phone, I wondered if she was angry that she had been friends with such a pervert and I was about to be the recipient of insults and slurs, then Sarah spoke. "Do you want my honest opinion?"

"Yes," I replied meekly, bracing for the worst. 

"I think you have already made up your mind to go through with it. Not to hurt your feelings but you always made a kind of crappy guy, but I always thought you'd be a beautiful girl. You told me to follow my heart, when I told you I was a lesbian; you need to follow your own advice. And you have my full support, I love you and always will. But once you transition I deserve pictures and an invitation to come visit."

I sat back in relief and astonishment, "Thanks Sarah, you're the best."

We hung up, and I felt like a weight had be lifted from my shoulders. I was a sissy, I wanted to be they're sissy.

I picked up my phone and texted Laura: "Hey, do you think you could come by Thursday. I would like to chat."

A few minutes later Laura texted back, "Of course, I'm so glad to hear from you. Someone was starting to miss you." A two pictures followed. One of her pussy, and another of Steve's erect cock. 

I replied, "LOL, tell them I've missed them too."

The next day I went to my job and turned in my resignation. I then went to the post office and change my address and told my building manager of my move. I returned home and began boxing up my belongings. 

Thursday rolled around and I was excited as I've ever been. I got myself up early and dressed in my red mini dress and strappy sandals. I tried my best with my hair and makeup, but I hoped Laura would bring hers. I patiently waited for 11 o'clock to come and Laura's arrival. 

Finally the time came and I saw Laura pull up in her Mercedes and trek towards my door. I opened the door as soon as she knocked, and welcomed her in. She kissed me on the lips and said, "I love the dress girl." She looked around the apartment seeing the moving boxes and looked back at me in excitement. "So, it looks like you made a decision."

"If the offer still stands, I'm all yours," I exclaimed. 

We jumped into each other's arms like a couple of school girls, dancing around in my living room. 

"Well now that's out of the way, how about some fun," Laura said as she dropped her coat to the floor revealing that she wore nothing underneath expect high heels, a pair of sheer stockings and her strap on. She grabbed me and pulled me close kissing me firmly. As our tongues wrestled, I teased her nipple studs with my free hands. I broke the kiss and lowered my mouth to her swollen areolas, sucking them like a hungry infant. 

"Let me see your sweet ass, Jacki," Laura demanded. I stood up and bent over the couch, and lifting the hem of my dress over my ass. Laura then pulled down my panties and had me step out of them, she then said, "here slut, stuff these in your mouth. I don't want your moaning to alert the neighbors."

"Yes mistress," I complied.

Laura the spread my ass cheeks with her hand and set to work on my hole with her mouth. Her tongue was every bit as talented as Steve's if not more. I bit down hard on my dirty panties as she licked my pussy. "Damn, Steve was right, you taste sweet."

She then looked at me, "are your ready baby," as she rubbed my ass. I nodded in approval. "Good slut."

Laura's dildo was positioned at my butthole, and with a gentle push she entered me. She fucked me slower this time savoring the fucking as she impaled me. I moaned through the panties as her strap on rubbed my P-spot. I began to rock my hips to meet her thrusts, causing the pressure on my prostate to increase. She could tell that her fucking had me close. Laura then withdrew her cock, leaving me open, then spinning me around and dropping to her knees, and taking my hardened clitty into her mouth and sucking me hard. In less than a minute I emptied my balls into her mouth. Once I stopped, Laura rose and brought her lips to mine, and we swapped my cum back and forth, before we each swallowed our share. We kissed once more before Laura looked at me and said, "Did you enjoy that sissy?"

I nodded, "yes mistress, I did."

"You might want to remember it, because it's the last blowjob you'll receive," she stated. "From now on when we play, you will not be allowed to jack your clitty. Your sexual release will come from anal play, and pleasing others. And since it's of no more use, we will keep it locked up. Your clitty shouldn't get hard because that's very unladylike."

I obeyed, "Yes mistress."

She reached into her bag, and fuddled around for a minute till she found a small pink plastic cock cage. It had two pieces, the first was a cock ring that went around the base of my testicles, and choked off the blood flow, while the second piece shrouded my cock and attached to the base with a small gold lock. Laura snapped the lock closed. The closing of that lock signaled the end of Jake, and the beginning of Jacki. 

We took and shower together and washed each other, followed by drying each other bodies. I then applied lotion to Laura's body, and she did likewise. To my delight she had brought her makeup supplies and quickly did my face. "We will have time for instruction and practice later, I'm just going to fix yours quickly so we can get loaded and on the road." 

"Sounds good, Laura," I replied. 

She quickly finished my makeup and teased my hair to life. She finished with a dab of perfume on my neck and showed me how to dab it on my wrists. I rose from my seat so Laura could finish getting herself ready. "Oh, Jacki, look in my bag. I brought some things for you and me to wear. There is a red and blue plastic bag, the red is yours, bring me the blue bag sweety."

"I'm on it," I laughed.

I scampered into the kitchen. I had already grown somewhat accustomed to the chastity cage on my clitty, and it wasn't as uncomfortable as I initially believed. I quickly found the appropriate bags and returned the blue bag to Laura as she curled her eyelashes. "Thanks darling, now get your butt ready we have work to do."

"Yes ma'am," I said playfully. 

Laura looked back at me in annoyance. She then just pointed with her free hand for me to go get dressed. 

I laid the bag on the bed and began sorting through the contents. The bag contained a black pleated mini skirt, and blue long sleeve shirt, with a slinky neck, and a pink Victoria's secret bra and thong. I removed the tags, and slipped myself into the thong and fastened the bra around me. The band size was perfect but the cups were quite small, only an A cup. "How are my forms going to fit in this bra?" I enquired. 

"Oh girl, don't wear those. I bought you some filler cups this morning, they are in the black box, in the bag," Laura replied as she sprayed her hair. 

I returned to the bag and found the box, and slid the silicon pads into the cups. They fit snug and looked a little more natural. Next came the skirt, which fit snugly around my waist, and covered my ass and legs down to mid-thigh. I quickly slid the shirt over my head, taking care not to mess up my hair and makeup. Checking my appearance in the mirror, I looked hot. The clothes fit perfectly and the skirt was young and flirtatious. I then realized I needed shoes. "Which shoes do you think Laura," I yelled. 

"Oh, what about those black pumps, that should be cute," she replied. 

Great, those are already packed. I sorted through my boxes, till I found the one marked shoes and opened it. I fished through the box till I found them. I closed the box back up and then slipped the pumps on my feet. 

"Oh Jacki, that looks so good on you," Laura exclaimed as she exited the bathroom fastening and ear ring to her ear. 

"Yes, you have great taste in clothes," I replied. As I admired her white halter type dress. Her auburn hair was layered perfectly and her gold stiletto sandals showed off her ruby red toes.

"I do, don't I," she agreed. "So are you ears pierced, I hadn't noticed."

"No, unfortunately," I replied.

"Not a problem, we can take care of it today." 

"I thought we were going to move my things today," I questioned.

"Honey," Laura stated, "who ever heard of moving in dresses and heels. A couple of Steve's workers are going to come by and take your boxes to the house."

"Oh ok, well that makes sense," I responded. "Well what are we going to do?"

Laura laughed as she touched my shoulder, "What girls do, we are going shopping of course."

"Are you sure I'm ready for that?"

"Yes, darling you look great," Laura assured me, "but even if someone does find you out, it won't be a big deal."

"Ok, if you say so."

The movers showed up later, and Laura instructed them about which boxes needed to go. And where they were to be unloaded. I got to check out the hunks that came to move the boxes. Laura caught me, "Pick up your jaw, girl, they are strictly off limits for you."

Once the boxes were gone, we got in Laura's car and headed downtown. First Laura had my ears and belly button pierced and bought me cute diamond studs for my ears and a cute rhinestone dangle for my navel. Then the afternoon was filled with dresses and shoes and lingerie. I have no idea how much money was spent on me but she spent a thousand dollars in Victoria secret alone. The last shopping stop was at Frederick's of Hollywood. Where she purchased several different items for me. One in particular she said was for tonight. It was a Red and Black babydoll, the front had a satin fly away design so that it exposed my navel, and in came with a matching red lace thong that was crotchless. Laura's trunk and backseat were completely full of shopping bags by the end of the day. I was completely exhausted, from putting on clothes and then taking them off, and the trying this and that on. But it had been a fun day. 

"Laura I hate to be such a wimp, but are we about done for today," I pleaded. 

"One more stop, but this will be some pampering, no more shopping," she promised. 

We pulled into a small shopping complex, and parked in front of a nail and day spa. I followed Laura into the place, and it was kind of dead. A small Asian lady saw us come in and yelled, "Customer." An older lady came to the counter, "What can we do for you lady's today?"

"We both need manicures and pedis, and a full wax," Laura ordered. The lady at the counter the led us to our chairs. We sat down and the young Asian lady removed both our shoes and washed our feet. I was a little nervous and I guess she caught on. "Relax, this is supposed to be fun," the lady stated. 

Laura laughed and pointed at me, "Don't worry she's a first timer." 

The Asian woman looked at me again, and then nodded, "oh I see now." I looked at Laura with my not amused look. "She knows what I am now for sure, Thanks."

"Relax darling, you aren't the first sissy she's seen."

Moments later a small army of women came out of the back room carrying various totes. Before I knew it, there was a woman at my feet and one on each hand as my nails and feet were sanded, buffed and primed. One of the lady's asked Laura, "What color would you like." 

"Red for the toes, French tip acrylics for the nails," she answered and nodded in my direction," and she will have the same." 

With their instructions given, each woman set to her task. Before long they were finished and I stared down as my hands now bore long acrylic nails, and my feet were more feminine and cute with bright red nail polish. Laura, then motioned for me to get up and follow her into the back, "We aren't quite done yet." 

She led me back to what looked like a massage parlor. Once inside she began removing her clothes, "what are we doing?" 

"It's time for our body wax, you have to be naked for that to happen," Laura laughed. 

I froze for a second, "I have to be naked?" 

"Well of course you do," she chided. 

"But she will see..." Laura interrupted "that you're a sissy, honey, she already knows, now relax and get naked."

Feeling a little defeated, I began to remove my clothes and lay them on the table neatly. I then stared and the table, which resembled part massage table, part gynecologist exam chair and part torture device. "How the hell to you get on this thing?"

Laura instructed, "Its easy lay on your stomach and lift your legs onto the leg supports." I followed her lead and it was surprisingly easy. I closed my legs to try and hide my caged clitty, like now was the time for modesty. Once I was settled, Laura yelled, "We are ready now."

On command the Asian woman accompanied by another came in and pushed a cart in-between the table. The little Asian lady came to my side of the table and asked, "Ready." 

"I guess," I replied. 

She then began spreading hot wax across my ass and applying cloth strips over the wax. With one swift motion she would rip the strip off of my body, taking with it the wax and 4 day old stubble. The first strip caused me to jump and yelp in pain. Which caused all the women in the room to giggle. That only added to my embarrassment. As she continued ripping the rest of the hair from my ass and the back of my legs, she began to spread my legs apart and wax the inside of my legs. This led her to the crack of my ass and taint which she laid bare in one fell swoop. After my crack was done, she tapped me on the ass and said, "Time to flip." 

I looked over at Laura and she just gave me to roll over motion with her finger. I reluctantly rolled over with my back on the table. When the little Asian lady caught sight of my caged clitty, she giggled, "it's so cute," as she touched it. I gave her a go to hell look, and she apologized, "Sorry, we continue." After what seemed like an eternity, she finally said, "All finished, thank you, "and quickly cleaned up and exited the room. Laura had been finished for some time, and just been watching and giggling at my discomfort. I removed myself from the bench and used the provided towel to clean myself of wax residue, and begin to dress. 

"So Jacki, how was your first wax," Laura cackled.

"If my skin wasn't so damn soft and smooth, I'd be pissed at you." My skin was incredibly smooth, unlike it had ever been. As I stroked my baby soft flesh, my clitty began to expand in its cage, straining against its confinement. For the first time it became uncomfortable, and I got dressed to keep my mind of it. 

Laura paid our bill and we exited from calls from the salon girls, "Come back to see us." 

As we exited into the twilight of the late afternoon, this was the first time I'd had to really admire their work. My hands no longer had a manly appearance, and I was already aware of the longer acrylic nails, "these are going to take some getting used to," I remarked.

Laura smiled back, "as are lots of things, but you look really hot now. Steve will be pleased with our work." I smiled back and we piled into the car and headed home. 

Today had been exhausting, yet thrilling experience. Laura had not only pushed my boundaries, but pushed me directly into the deep end of sissyhood. Yesterday, I was a normal guy with a crossdressing fetish, today I was a cockloving sissy, waxed, primped, and locked in chastity by my seductive mistress and daddy. Oh, who was I trying to fool, I thought to myself; I'd always been a sissy at heart, I just didn't know it.

I laughed a little at my realization, Laura noticed, "What's so funny over there, Jacki." 

"Oh nothing, just reliving some of today." I answered. 

"Well this is just the beginning honey," Laura chided. "I better call Steve and let him know we will need his help with all these bags."

She dialed the number and hit send as we pulled into the drive and she entered her code into the keypad. Laura told Steve to meet us at the garage to help with the bags. The gates swung open and we made our way down the drive toward the house. Laura steered the car around the house and into an open stall in their six car garage. To the right sat a bright red Ferrari, I commented, "Pretty car."

"Oh that's Steve's, he likes to drive the ridiculous thing to the beach, so all the young girls hit on him," she retorted. "He will probably want to take you for a spin in it."

As the garage door began to close behind us, Steve appeared and opened up my car door. He offered me his hand and helped me from the car, "Wow you girls look amazing. I love your nails Jacki, very sexy."

I smiled and said, "Aww, thanks Steve," as he wrapped me in a hug. He released me from his embrace and caught me glance at his red sports car. He remarked, "I'll have to take you for a ride, Jacki."

"Easy there cowboy, we have too much accomplish, to get our guest settled in, before the party tonight," Laura interrupted. 

Steve looked at her in disappointment, "Another time then."

"The trunk is popped, bring all the bags from the trunk and car into the pool house, I'm going to show Jacki around Ok," she instructed. Steve nodded in acknowledgement and I followed Laura into the breezeway that connected the main house, and the garage, to the pool house. As we made our way towards the pool house, Laura chuckled, "What did I tell you about that car." We both shared a laugh at her quip. 

We reached the pool house. Laura opened the door and guided me in, "Welcome home." I walked in to a large room which was setup, as a living room/kitchen/dining room. The space was well done and expertly decorated. The travertine floors of the main house flowed into the pool house, and the furnishing was of all the same quality. "Wow this is really nice, this won't take much getting used to."

Laura smirked and continued the tour. At the back of the living space, a set of double doors opened into a large bedroom. In the center sat a king sized, canopy bed, constructed of dark wood. The room was filled with a matching bedroom suite. To the side of the bed lay all of my boxes and belongings the boys had brought from my old apartment. We walked through the cardboard boxes into an opening. On one side there was a bathroom, with a large soaker tub, and walk in shower; to the other side a small sitting area with a vanity mirror, and a large walk in closet. Laura led me into the closet, showing me where I could put my dresses, skirts, blouses and lingerie; drawers for bras, panties, hosiery, and a shoe rack for my heels. 




Jacki's Journey into Sissyhood Pt. 03



It was a lot to take in, but I did my best to keep up. We walked back through the bedroom into the living space to help Steve, as he burst through the door arms full of shopping bags and deposited them in the mountain of bags on the floor. Steve gasped, "I think that's the last of it." 

"Well I guess I should help Jacki, start putting some of this stuff up," Laura said while looking over the floor full of clothes and shoes. 

"Uh hmm, babe, you might wanna look at the time," Steve interjected.

Laura glanced at her watch and threw her arms up in exasperation, "Your right, I need to start getting ready for the party."

"Wait what party," I questioned. 

"Oh, Steve and I have a party to attend. It was a previous engagement, I'm afraid we won't be back till later, but ill promise to bring you back a surprise to make up for our absence," Laura replied.

I nodded in understanding. "That's fine, I have plenty to keep me busy," I laughed, waving my arms at the pile of shopping bags.

Steve and Laura kissed me goodbye. Laura then said, "Ill text you later when we are on the way back."

"Ok," was my response as they left me to my task. I dolled over the heap of shopping bags try to decide where to start. As I pondered the proper starting point, I came to the conclusion that I might as well make myself comfortable. I dug through the mass and found the Victoria's Secret bags I was looking for and headed for the bedroom. Dumping the bags contents onto the bed allowed me to quickly sort through the items I needed.

As I dug through the pile of clothes and product on my bed, I became keenly aware that my manicured nails would require me to be extra careful. 

I picked out my desired products and walked to my sitting area, and laid my things out on the table. I then kicked off my heels, stripped off my clothes, and grabbed the scented body lotion that Laura had purchased. The scent was intoxicating and fruity, it reminded me of the Caribbean. I placed my leg on my stool and began massaging the liquid into my freshly waxed skin. Prior in the day, following the wax, I had said my skin had never been smoother. As my skin absorbed the lotion, it took on a buttery soft texture, the feeling was incredible and caused my clitty to strain against its confinement. The discomfort of my chastity did little to diminish the delight I experienced in moisturizing my body. Once done, I selected a pair of light blue boy shorts, with the word "juicy" across the butt. I laughed to myself, "Seems appropriate." I pulled the stretch material up my legs and into place, before fastening a matching bra into place. To complete my outfit, I squeezed into some yoga pants and a cute pink tee. I immediately understood why every 20 something girl in the country loved these pants, they make your butt look awesome and are so damn comfortable. 

After getting dressed, I poured myself some wine, and got to work. While dressing I decided to start in my bedroom and empty the boxes from my apartment first. I made quick work of the contents, and quickly placed my things in their place. I even found a place for my toy collection. 

Next up on the docket was the mound of stuff in the living room floor. I just started gathering bags and carrying to the bedroom before dumping the contents on the bed. I found it easier to just sort the jumble, putting up clothes and shoes as I went. 

In a couple of hours I had sorted through all the bags, not to mention drained a bottle of chardonnay. I stood in my closet to admire my labor. 

Everything had its place. Dresses over here with the blouses and shirts, then skirts, shorts and pants, followed by lingerie or all sorts: bustiers, corsets, babydolls, and robes. In the drawers of the built-ins I had organized my bras in one, panties in the next, while hosiery was neatly folded in the next. T shirts and workout clothes were folded away in a cubby, and all my shoes were on the rack next to their match. "Not bad," I thought to myself. 

Finally done, I cleaned up and the bags and boxes outside for Steve to take off, before falling into the couch to watch some TV. I flipped my back and forth between stupid reality shows for a while before finding something to watch. I sighed as I took in my surroundings. This felt right. Sarah had been spot on in her advice I belonged here. 

About 11:00 my phone vibrated with a text from Laura: "Mistress and Daddy are on the way home sissy. Get dressed in your red babydoll outfit I bought for you, and don't forget your plug either. Wait for us in our bed, and if you been a good sissy, I'll let you have your present."

Her orders set me to work. I flew into action and quickly was naked and found my outfit. I decided on no stockings or fishnets, as I wanted Steve to have full access to my newly waxed legs; and a pair of strappy sandal stilettos to show off my newly painted toes. The crotchless thong took some adjusting to not expose my caged clitty, but I managed to make it work. The baby doll fit my body well, with a bandage style lace detail across the bust. I hoped Steve wouldn't be too disappointed that I didn't wear my fake breasts, but they really didn't work with the outfit. The flyaway front of the babydoll exposed my newly pierced navel. I glanced in the mirror to check my look, before retrieving my butt plug and inserting it in my aching pussy. 

I made my way from my place to the main house. As I did the cool breeze caressed and excited my smooth skin, while the crystal plug in my ass rubbed my P-spot. The combination caused my imprisoned member to groan against its confinement. 

My pace quickened and before long I entered Steve and Laura's bedroom and bounded into bed. It wasn't long before car lights illuminated the bedroom, and I heard the back door open and close. Next came the unmistakable sound of Laura's high heels on the tile floor as she approached. She burst through the door like a sex filled tornado, "There is mistress's sissy girl."

"Have you been naughty or good tonight," questioning me, while examining my outfit. "Very good Jacki, do you think you earned your present?"

Steve entered and gazed at me with lustful eyes, "I think she has earned a reward Babe." 

Laura pushed her dress off the shoulder and let it fall to the floor to reveal her lingerie for the evening. She wore a strapless shelf bra in black lace, which barely contained her massive mammary glands. Further down around her waist a black garter belt held up fishnet stockings, while her pussy was bare. 

Laura climbed onto the bed and ordered me to lay down. She then straddled my head so I was now face to face with her pussy and ass hole. I now noticed that her privates were covered in tight latex, which she promptly peeled off exposing herself to me. 

I could smell her immediately, Laura's usual sweet scent, was now muskier with smell of wild sex about her. She lowered her well fucked pussy to my mouth and moaned, "Time for dinner sissy."

As she said those words, the first globule of cum came flowing from her vagina. It was salty mixed with Laura's own juices, to create a delicious sex cocktail. I lapped at her lips voraciously, trying to please my mistress and not miss a drop of her surprise. 

As I slurped up my Mistresses' sex, my cocklette's confinement became almost unbearable, and I squirmed my body around searching for relief. Laura sensed my discomfort and started to rub my testicles, stimulating by engorged clitty. Her teasing only elevated my distress as I moaned into her vagina. 

I felt Steve climb onto the bed and make his way over to us. Laura teased me, "Look Steve, at her little penis trying to get hard in her little pink cage, it's so cute isn't it, "as she slapped my captive clit. 

Steve laughed back, "It is, that thing must be painful."

"No our sissy girl, loves her cage. She would cry if I took it off her, look at how much fun she is having," Laura rebuked.

Steve kissed Laura passionately, as I went to work knowing on her clit. Laura began to moan, "Oh, our sissy is catching on quick. She knows how to make mistress cum." 

Laura leaned down and grabbed my ankles and lifted my legs into the air as she rocked back, exposing my smooth sissy slut hole to my well-endowed daddy. "Daddy why don't you give your sissy girl a good fucking to take her mind off her aching clitty."

At her command, Steve licked down the back of my leg, tracing a path to my entrance. He moistened my ass hole with his tongue spreading his spit around my opening. He sat back on his knees pointing his cock into the air and spoke to Laura, "Lube up my cock, babe." 

Laura then rocked back forward, with my legs in hand, and swallowed his cock. Basting his rod with her saliva. Laura then rocked back and spreading my legs, "She's all yours daddy."

Steve braced himself on the back of my thighs as he pushed his enlarged cock into my depths. The sensation of penetration and the pain of my straining clit, caused me bite down on Laura's clit. Laura called out in joy. Her cries and moans of passion, spurned him to tug at her pierced nipples with his mouth. 

Steve hammered away at my prostate with his cock, the ecstasy caused me to moan into Laura's pussy lips, and overpower the pain of my caged prick. Laura then released my ankles, and grabbed my head pressing my face into her harder, and began riding my tongue. The combination of me at her vagina and Steve's pulling at her tits, brought Laura into orgasm. Laura convulsed and filled my mouth with her juices before dismounting my head and collapsing on the bed beside me, as Steve fucked my pussy harder. 

Steve leaned in making out with me, and sharing in Laura's nectar. 

Laura regained her composure, "Darling, let's see our sissy slut ride her daddy's beautiful cock." 

He smiled at her, and unsheathed his tool from my ass. He then laid on his back next to Laura. She immediately attacked his dick sucking at it hungrily. "Her ass tastes so good doesn't it," Laura moaned. Steve nodded in agreement. 

I rolled over to my knees and straddled Steve's torso. Laura placed one hand on my shoulder and guided Steve's rod to its destination. I lowered myself down, impaling my ass on Steve's pole, and slowly started bucking my hips. 

Laura offered encouragement, "That's it, good, rock your hips, please your daddy sissy slut."

Steve's moans of pleasure signified his approval. I slowly rocked back and forth on his cock, stretching my hole wider. Laura leaned back, fingering her pussy and began making out with Steve. In a quest for pleasure I placed my hands on my daddy's chest, bracing myself as I sprang my ass on his dick. I used his cock head to scratch my bliss button, as my orgasm began to build. 

I moaned and bucked like a whore, as Laura cheered me on, "Yeah baby, ride that big dick." 

I rode Steve's prick harder until finally I couldn't hold back my orgasm any longer. My body rocked and quivered and my struggling clitty spit my fluid onto Steve's abdomen. After I came, Laura peeled me of Steve's cock and looked at me wildly, "Come on slut lets finish him off together." 

We shared Steve's cock like a popsicle, both licking his shaft and balls, savoring in my taste. We licked and sucked greedily, until his cock erupted in a semen fountain. We both lapped and slurped at the stream of cum that came forth from Steve's cock. 

We both cleaned his instrument with our mouths, drinking down his creamy sap. Laura then kissed me and we swapped our collected reward back and forth between each other's mouths. 

Laura and I eventually collapsed on either side of Steve. We girls fondled his softening penis, as the group shared a three-way make out session. After we all came out of our sex crazed trance, Laura shouted, "God that was good."

The three of us laughed in agreement. 

"You guys were awful worked up, must have been one hell of a party," I remarked and winked at Laura. "And my present was just what I wanted, it was delicious." 

"There a lot more where that came from," Laura replied. 

Steve butted in, "as long as I get to have this kind of sex, with these beautiful ladies every night I don't care how much of my money you spend."

We laughed and chatted, about the evening. Laura and Steve told me about their "party," that evening. What they called a party, was really a swinger's meeting. The couple belonged to a rather elite swingers club, which had periodic meetings at host member's residences. They consisted of likeminded couples as well as a few select single men and women, basically fucking and sucking to their hearts content. The group was very organized and formal, as each attending member had to have a clean bill of health logged with the club's doctor before they were cleared to participate. 

Steve and Laura had committed to going to tonight's event, prior to our relationship, and didn't back out the occasion for fear of losing their spot in the group. As we talked it became evident that Steve had abstained from sex at the party and had just enjoyed the view as he watched Laura suck and fuck till she was satisfied. The party is where she had collected my present for the evening, learning of its origin caused me to blurt out, "Well please thank to chef for my delicious snack." 

Laura cackled at my comment, "What a dirty sissy slut we have on our hands here."



Jacki's Journey into Sissyhood Pt. 04



The next couple of months with Steve and Laura were incredible, and the happiest of my life. I felt like I had found my place with people who genuinely loved me. I spent my days sharing their life and nights sharing their bed. 

Under Laura's tutelage, my metamorphosis continued. I was on a strict diet and exercise routine that helped me drop my weight and shape my feminine figure. Laura was pleased with my progress, as I was able to drop 20 lbs. We were now exactly the same size. My daily routine of squats and lunges, had fattened my ass and widened my hips much to Steve's delight. 

As the warmer months came, Laura and I would lay out by the pool and work on our tans after workouts, and we continued shopping and pampering ourselves to our hearts desire. My hair began to lengthen and due to mine and Steve's pestering, Laura died my hair a light blonde. She resented but after time, agreed I looked better as a blonde.

Laura and I became closer as the days past and 6 months in we were nearly inseparable. I came to know her better than I had known anyone, she became family. I learned that she had a son from her previous marriage, who was in the military, and she hadn't seen in over a year. I learned that she was known as a queen of spades in swinger lingo, and only fucked black men at parties. Steve was the only white man she had sex with. 

My feminization then went stagnant, I was unable to diet and exercise away the rest of my manly frame. Laura tried every trick that she knew, but to no avail. So she contacted the other swinger mistress she knew for advice. The answer was simple, estrogen supplements. 

Laura gathered all the information she could and presented me with the options. "If we you wish to go further, this is the only course I'm afraid," she summarized.

"This is a big decision, there is no turning back after this is it," I sighed 

"I'm afraid so Jacki," Laura said. 

My friend's advice to me about my indecision to move in with Steve and Laura popped into my head at that moment, "you were never much of a guy,..., you might make a pretty good woman." 

I contemplated my response, and then smiled at Laura, "we've already come this far let's do it."

Laura exploded into excitement, and we embraced one another. 

The next day I began supplements and injections. The first month was difficult, my moods, weight, and sex drive fluctuated wildly. I wouldn't eat for days, and then I stayed hungry constantly. My body ached all over, even my hair hurt. My nipples became extremely sensitive and my caged cock became numb. 

By the beginning of August my body began to adjust. My weight and mood normalized as did my sex drive. The transformation of my body was the amazing part. The hair growth on my head accelerated while my body hair growth slowed dramatically. The manly muscular shoulders, arms, and chest melted away. My hips widened and my ass got fatter. To my delight, my nipple puffed out as I formed small breasts that filled my bra cups. Steve really enjoyed the budding tits to play with, and I adored how they shook and bounced as he fucked me. The estrogen supplements also relaxed my voice, to a feminine tone, and softened my facial features. I truly began to look like a mid 20's woman. 

I now got no more long inquisitive looks from women while I was out with Laura. They now only viewed my as another woman. I also began drawing attention from men of all ages, who I would catch eyeing me everywhere I went. Being the flirt that I am, I would tease them, by flashing them a view at my panties when I uncrossed my legs or bent over. Laura would just roll her eyes, saying," you're insatiable," and laugh. 

The supplements shrunk my clitty down to the point that the cage no longer fit. Laura resorted to just tying it up with a cute bow, as it no longer would get hard. Most of the sensitivity of my clit and been totally drained except for the small cock head that stimulated me when it was rubbed. My orgasms had changed as well, they were even more intense than they had been before, and lasted much longer. My tiny cock no longer spurted cum during climax, but instead only dribbled clear liquid. 

By late September, all traces of the male I had been, were erased. I now appeared to be a real woman, with only my little nub to remind me I wasn't. 

The first day of October came, and while we were working out Laura stopped me. "I have a question to ask you, Jacki." 

"Sure, what is it," I answered.

"Steve and I have been considering, when might be a good time to introduce you to the lifestyle."

"What do you mean the lifestyle," I interjected. 

Laura responded, "The swinging lifestyle, the club we belong to,.., you know." She continued, "Anyway, I didn't want to bring you in till I felt you were ready. Now physically you are ready, you look stunning and I'm sure the women and men alike would love you, and you would be quite the hit at our parties. But I wondered whether YOU were ready."

I thought for a minute about my response as I finished my set, "Two months ago I would have said no. But I've been becoming more interested in what you guys do on those nights. And I love you two, but I've been wanting to kind of, well you know, experiment a little."

Laura smiled and laughed and then wrapped me in a sweaty hug before kissing me, "I thought you might say that, I've noticed you flirting with boys at the mall on our shopping trips."

"I learned from the best," I retorted and returned her kiss. "I have to ask, why are you bringing it up now?"

Laura replied, "Well for the last several years Steve and I have hosted the club's Halloween party. Steve thought it might be a good coming out party for you."

I squealed, "I love Halloween parties, I mean this would be my first as a girl, but heck it has to be even more fun as a girl."

Laura laid out the agenda, "well in order for you to be able to attend the party, we need to get you approved by a 3 members, and get your medical check-up."

"Well what are we waiting for," I said, giving Laura a wink. 

The next couple of weeks, Steve and Laura took me to dinner with 3 other couples they knew. I met each of them and we talked and chatted. They asked me questions about myself, and what I liked to do and so on. There was never and hanky panky, well except what happened with Laura and Steve afterwards, just dinner and drinks. 

The week before the party, at dinner shared the good news. "The McConnely's, Stewarts, and Conners all said yes, Jacki's on the list."

We all cheered and toasted the good news. Laura chimed in, "I'll call Tara, and get her an appointment for tomorrow so she is locked in."

The next day, was a normal morning. Laura and I woke up and did a quick yoga session, before going for a run. We made it back to the house, and Laura told me, "Go get some clothes together, probably a cute top and skirt, and come take a shower with me. I'll do your hair and makeup and we can head to the doctor's office." 

I did as I was told picking out a cream colored mini skirt, a sleeveless pink top and my pink peep toe platforms. For underwear I picked out a white lace pushup bra and thong. I then joined Laura in the shower and we washed each other. 

I played with Laura's nipple studs as we cleaned ourselves, "Laura, I think I'd like to have mine pierced as well."

Laura looked back at me in astonishment, "Well I guess we could do that after your doctor's visit today," as she fondled my breasts sizing them up.

I smiled back at her, "yes lets."

We exited the shower and got ourselves dressed and headed downtown to the doctor's office. 

Laura and I arrived early to the office. We were greeted by a cute young blonde receptionist, named Courtney. She was quite bubbly and commented on how much she liked my hair and how cute my outfit was. I thanked her and she told us that Dr. Conner would be with us in a moment. 

The door to the office and Dr. Conner stepped through the door and called out, "Jacki." I immediately recognized Dr. Conner as part of one of the couples we had dinner with. Dr. Conner was in her mid-30's, a brunette with shoulder length hair, and a short woman in stature; no taller than about 5'2" or 3". I remembered from our dinner that while she wasn't blessed with a large chest, she more than made up for it in ass. 

"High Laura, it's so good to see you again," she said as the two women embraced one another. "And nice to see you again Jacki, I was hoping I might see you again. When Laura called me last night I got all excited." 

We embraced and I said, "It's wonderful to see you again to Tara." 

Tara led us to an empty exam room and began the usual checkup procedures. Once they were completed she had me stand and turn for her. "I must say Laura when you told me your plan, I didn't think you could pull it off. But she looks as much like a girl as Courtney does." 

Laura commented, "Yes she has been a breath of fresh air." 

Tara then turned to me, "Jacki, take off your top and skirt and sit on the examination table please." 

I complied and stripped down to my underwear. I sat down on the table and Tara extended two foot stirrups. "Just rest your feet here sweety."

I put my feet into the stirrups so Tara could examine me. She removed my thong and handed it to Laura leaving my clit and ass exposed. Tara played with my shriveled cock, "Does it get hard anymore," she asked. 

"No not since I started the supplements," I answered. 

She then took a long cotton swab, and inserted it into my ass, swabbing my anus. She placed the swab in a bag and sealed it. 

Tara looked me in the eyes and patted me on the thigh, "And that's that, you can get dressed sweety."

I dismounted the table and began to redress, as Tara and Laura talked. 

"So are you and Steve ready for next Saturday," Tara asked. 

Laura responded, "We are getting there, we will really start prep this week."

"It must be nice for you having Jacki this year, to help," Tara added. 

"Oh it will be, I know she is excited for her first party," Laura replied. 

"It won't be her last I'm sure," Tara giggled. "So I took off for next Friday, and I was going to take Courtney to the salon, for mani pedis and a wax before Saturday. Why don't you and Jacki come along and we can have a girl's day."

Laura answered, "That sounds like fun, and we're there."

I finished dressing and we exited the room. "I'll get these to the lab ASAP, and I'll email you the finalized list this afternoon, see you girls Friday."

"Sounds great girl," Laura chimed. 

After the doctor's visit we made our way to the tattoo parlor, where the same pink haired girl, named Roxy, waved us back. "What will it be today, ladies?" 

"I need to get these done today," I said pointed to my tits. 

"Not a problem," the girl said, "what do you think Laura, bars like yours or rings?"

Laura replied, "I think bars would be best."

I took off my shirt and bra and handed them to Laura, before sitting down in the chair and leaning back. Roxy returned with a bowl of ice and snapped on her latex gloves. "Now, I have to use the ice to get them hard and numb them up." 

I nodded ok and we proceeded. Once Roxy was satisfied that my nipples were sufficiently numb and erect, she picked up the needle and looked at me and said, "Here we go."

In a quick motion she drove the needle through my nipple. Pain shot through my body and it caused me to bite into my pink glossed lip in order to keep from yelling out. The other nipple wasn't any easier but in short order my nipples bore stainless steel studs just like Laura's. Roxy placed two gauze pads over my throbbing nipples, and instructed, "Change these out before you go to bed, a little bleeding is normal. You can use ice to help with the swelling and pain. Keep them clean and wash them with this antiseptic wash. Oh, and Laura tell Steve not to tug on these for a couple of days, like yours." 

Laura laughed, "I'll have to tie him down." 

Roxy handed me a stack of gauze pads and a small bottle of antiseptic wash. I didn't think I could stand putting on the bra, so I just slipped the shirt over my head. We left the shop and headed home for the day. 

I got home and immediately took off my shirt, and I spent the rest of the afternoon with ice on my pierced teats, trying to subside the pain. I did get to show them off to Steve when he got home, and no surprise he loved them. Thankfully the pain had mostly gone by the next day, and was completely normal by Sunday afternoon. Now every moment stimulated me sexually, any brush against my nipples just got me hornier. No wonder why Laura was always randy. 

The next week was quite busy for Laura and me as we made plans for the weekend's festivities. It was unseasonably warm for October with temps rising well into the 80's. Laura and I even broke out our bathing suits, to work in. 

Laura had studied the guest list and there were over 100 confirmed couples and almost as many singles. Steve had some of his worker's help us with unloading trucks and helping us with decorations. There was plenty to keep us busy, not to mention we still needed costumes. 

Before we knew it, it was already Friday. Due to proper planning and a lot of hard work we had the majority of the prep work done. Today us girls would relax and meet up with Tara and Courtney for some pampering. 

Laura and I woke up, and decided to get a work out in. It was some dang hot that we cut our run short and walked back to the house. "Im so sweaty, I'm sticky," I said as I rang out my top. 

"Hey why don't we shower off and lay by the pool," Laura proposed. 

"Oh that sounds fantastic," I replied. "Hey, why don't you call Tara and invite them to lay out with us."

"That's a great idea," Laura remarked. 

"I'll go jump in the shower first, come join me when you're done," I said as I peeled off my workout clothes. 

I let the cool water run across my body as I waited for Laura join me. I was running my fingers through my hair when I felt her nipple rings on my back. Laura's hands reached around my body and tweaked my nipple studs, causing me to moan, "Don't get me going if we don't have time to finish." 

She laughed, "unfortunately your right, Tara and Courtney are on the way actually." 

"Well that's great," I replied. We quickly washed off our bodies, then lit in to getting ready. Laura sat out a shiny gold bikini with tie sides for me and her leopard print pumps. I slipped everything on and began brushing my hair. She appeared in the mirror, wearing her zebra print bikini with the push up top, and her black wedges. She watched me brush out and start to dry my chin length hair, "why don't we try something different with your hair for tomorrow night." 

"What did you have in mind," I asked. 

"Well your hair is long enough now for me to blend in extensions, but instead of blonde, why don't we make you a redhead like me," she suggested. 

I pondered the offer, and wondered how I'd look like as a redhead. "I actually kind of like the idea we will look like sisters that way."

"More like mother and daughter," she laughed. 

"A very kinky mother and daughter at that," I added. 

We finished getting ready, and Tara and Courtney arrived. We poured some wine and prepared to catch some rays. 

We talked and laughed about girl stuff mostly. Courtney and I really hit it off, as our personalities seemed to mess well. As it turned out, she was in a similar situation to me. She was a sugar baby for both Tara and her husband Greg. She had been living with them for 2 years, since they had introduced her to swinging. She had been working her way through college as a bartender when Tara had hit on her and talked her into coming home with her. Saturday would mark her 4th party with the couple. She said she would help me out at the party, so I didn't get overwhelmed. 

"Well aren't you two just hitting it off," Tara laughed. 

"Best friends forever," Courtney smirked. Courtney and I then locked our pinkies together. 

That in sighted laughter from Laura and Tara. 

Tara then spoke to me, "Jacki, why don't you show me to the pool house bathroom babe,"

"Sure thing," I answered. We both stood and Tara and followed me into the pool house. 

I led here into my bedroom and then pointed her towards the bathroom. The next event caught me totally by surprise. Tara walked right up to me and kissed me firmly on the mouth, pushing her tongue into my throat. I recoiled, "Dr. Conn,.., I mean Tara what are you doing." 

"Awe, Jacki I didn't really need to use the bathroom, I just needed a reason to get you by myself," Tara moaned. 

"But Courtney and Laura, I mean Laura might not want us to be doing this," I stammered. 

Tara reassured me, "Oh no it was Laura that suggested I try you out girly, I think she wanted to try out Courtney as well." We then looked out my bedroom window towards the pool to see Laura and Courtney making out and rubbing each other through there bathing suits. "See they are having fun let's have some fun of our own," she asserted. 

She then grabbed my head and pulled our lips back into contact. Her lips were plump and soft, and her body was softer than Laura's toned figure. We stood at my bedside with our tongues intertwined as we groped each other's body's. Tara then untied the sides of my bikini and let it fall to the floor, followed by removing my top. She fondled away at my cocklette while looking me in the eye, "I was kind of worried that we might to busy tomorrow night, and I wouldn't have a chance to play with you. You're all I could think about since your doctor's visit."

Tara then kissed me again, before turning her attention to my nipples. She licked and sucked at my buds and tugged at the metal studs with her teeth. Her simultaneous stimulation of my nipples and cock head made my eyes roll back, and my knees go week in pleasure. She sensed my ecstasy and stopped here stimulation, "get on the bed Jacki, Im going to take you for a ride." 

I climbed on the bed, and caught a glance of outside. Courtney and Laura were now completely naked; Laura's face was buried in-between Courtney's legs, tonguing her pussy.

I laid on the bed watching the love scene unfold, as a now naked Tara joined me on my bed. She carried her black tote and emptied its contents onto the bed. Among the suntan lotion and lipstick, there was a strap on harness, with a small clear glass dildo attached. It was only about 6 inches long, but the head bore a large orb that was wider than the shaft. The smooth shaft was dotted with raised pink hearts. Tara strapped the device around her waist as she said, "This is Courtney's favorite, and I thought you might like it as well."

She bent down and kissed me hard biting and pulling at my lower lip with her teeth, "Now on your back baby, let me see that pretty pink hole." 

I complied with her requests, and flipped to my back and invited her in. Tara moved into position and then lubed up her crystal wand, before leaning in to mate the tip of the glass rod to my orifice. The cool glass made my hole recoil in an attempt to get away. I hadn't been subject to a fucking in almost a week, and my hole had tightened so it took a minute for Tara to force herself into me. Due to her persistent pushing, my anus finally yielded to her demands, allowing the sphere of the dildo tip to pop home. 

The suddenness of the of my opening cause pain to shoot through my body, "Oh Shit," I cried. My cries of pain caused Tara to bury the rod into my body, and laugh, "Damn that little hole is tight."

I tried to smile back at her, as my pain waned. Thankfully the coolness of the glass not only caused a powerful stimulation to my p-spot, but also soothed my pulsating asshole. I bucked my body in acknowledgment that I was ready. And Tara began slowly fucking me. 




Jacki's Journey into Sissyhood Pt. 04



The glass shaft had a unique feeling, as the raised hearts glided in and out of my pussy. The large tip also did the trick of providing extra pressure on my prostate. In no time at all Tara's fucking had me writhing in joy below her. She moved in and locked her lips onto my nipples and ground her harness pussy into my ass rubbing her clit in the process. This motion caused the round tip to bounce on my prostate at the perfect angle. The sensation caused me to cry out in euphoria, "Oh my god, that's it right there, oh my god, fuck it Tara." 

My wailing drove Tara's desire she sped up her grinding, and teased my studded teats harder. Each thrust caused the tip to slam harder and harder into my orgasm button, and her twerking of my nipples pushed me closer and closer. In short order I was at the precipice, and screamed, "Yess, oh fuck, Im close." 

Tara new exactly what do to push me over the edge, withdrawing the crystal dildo to the tip, and the slamming it back into my pussy. My sphincter muscles clamped down on her glass cock, my eyes rolled back as the first wave of bliss hit and my climax washed over me. I convulsed on the bed beneath Tara moaning, "Oh fuck Tara, Im cumming!!," as my clit began spurting in release. Tara saw it squirt which drove her wild, she popped her dildo out of my hole and lapped at my clitty sucking up its juice. She promptly brought my secretions to my mouth and we both reveled in my sex. 

"Damn girly, that was one hot fuck. I'll have to keep Greg away from you, or you'll steal him away."

We both laughed hard at that, and she collapsed onto me in a sweaty tangle, giggling like teenagers. Tara then looked at me in the eyes, and touched my painted lips with her finger, "Let's put this pretty little mouth to good use."

She got up on all fours, bearing her perfect ass to me. She placed her head down on my comforter and pushed her rump into the air, taking her hand and smacking her behind, "Lick me baby."

I obliged her request, parting her voluptuous cheeks with my hands and licking her from pussy to butthole. This caused her wail, "That's what I like your dirty girl."

I set to task lapping at her sweetness. I probed both of her holes with my tongue. Grinding my nose full of her scent, her sex pheromones ignited my lust, and I attacked her pussy and hole with voracious appetite. My stimulation of Tara's orifices caused her to moan, and buck like a wild mare, "yeah Jacki, lick that pussy," she moaned. Her legs shuddered as she muttered through gritted teeth, "God that's good, fuck, fuck, Ohhh god yes."

Alas in the positon we were in I had little access to her clit. I quickly flipped over to my back, and positioning my mouth under her privates. Tara got the idea, and raised her torso grabbing a hold of my headboard for stability. She lowered herself to meet me as I buried my face into her mound. She grinded her pussy into my mouth as my tongue searched for her button. I finally found her spot, and began my assault on it. I licked and sucked at her engorged clit, as Tara moaned in approval, "Oh fuck baby, that's it suck that clit."

I continued by stimulation until I felt her body tense and her breathing quicken. "Oh fuck, oh fuck, oh, fuck, oh fucking god damn it, yes, yes, YESSS," Tara screamed. Her head rocked back and she ground her pussy into my face hard, suffocating me in her love juices, as a powerful orgasm washed over her body. She sat their motionless, and silent as her joy receded. 

The silence was broken, by loud clapping, "Bravo, Bravo."

Tara rolled off my face to reveal a totally nude Laura and Courtney. "How long have you guys been standing there," Tara questioned. 

"Long enough to see you big finale, I told you she had talent," Laura laughed, as both her and Courtney joined us in bed. 

"I told her that Greg was going to be dying to take her home after I saw the way she fucked, but on second thought, fuck Greg, she's coming home with me," Tara hooted. "I saw you two, and you looked to be having some fun as well?"

Laura and Courtney gave each other a devious look and chuckled, "Yeah fun was and understatement."

I caught Courtney eyeing my clitty, and remarked, "Well I guess my secret is out now."

Courtney then began fondling it with her hands, "Yeah that's what Laura was telling me, I didn't believe you were anything other than a genetic girl."

"Not quite," I giggled. 

We all lay on the bed in our post orgasm mess and lightly played with each other's naked bodies till it was time for us to get up and get ready. 

We got dressed in our dresses and headed out for the day. We grabbed a light lunch, followed a trip to the spa, for a massage. Courtney and I, took ours in the same room so we could flirt and tease the cute guys that were our massage therapists. We then headed to the hair supply shop, and Laura picked up the supplies to do my hair. Both Tara and Courtney agreed that I would look hot as a redhead. 

Our final stop was at the nail salon for a wax and mani pedi. Laura and I picked out a matching design for our nails. They were a white gel coat, with metallic blue tips. Then the nail artist applied little red crystals in the shape of an anchor. The finished product was too cute. When our wax jobs were finished we gathered the other girls and headed for home. 

Once we were home we all said our goodbyes till tomorrow night. 

The day of the party the house was a bustle of activity. Caterers, DJ's, and liquor trucks and their workers mingled around delivering their goods. By noon the all the bar's had been stocked, the DJ booth was set up, and the food was ready. Steve's workers rolled in giant black totes and left them in each room, Laura thanked, "thanks a lot boys, now you guys go home and get ready. Remember you are to be back here no later than 5, is that clear." 

I asked Laura, "Are they all coming to the party."

"Well yes and no. They come as help and servers during the party. They will be dressed in tuxes with the girls who are serving being in plain black dresses, and they all wear masks to conceal their identity. The members know they are strictly off limits, and if they are caught participating in any activities they are never asked back. They all make 1000 dollars for the night, plus tips, so this is a coveted job."

"I'll say," I responded. 

Just then Steve walked in, "hey girls is there anything you two need me to do?"

"Yes darling, why don't you head downtown, and pick up our costumes for the party," Laura asked. 

Steve responded, "Not a problem, I'll have my phone if you happen to remember anything."

Steve exiting, leaving Laura and I alone. "Come on sweety we have a little more prep to accomplish now that everyone is gone."

In each tote there were sets of rubber sheets that we draped over each piece of furniture in the room we then placed pumped bottles of lubricant sporadically in each area. It took us about 2 hours to get everything covered and ready. Steve returned shortly afterward with our outfits. "Steve why don't you get ready over at Jacki's, and that way us girls can use the master."

Steve handed each of us our garment bag, and left us to get ready. Laura and I quickly showered, and both of us cleaned our holes thoroughly. I then sat down so Laura could work on my hair. She colored and washed and dried it and then set work adding and blending in my extensions. She then brushed everything out adding volume and setting my look into place with hair spray. 

"What do you think," she asked. 

I tossed my flowing auburn hair about, and smiled really big, "I love it, it's perfect."

We laughed and hugged, and I moved over to the makeup counter, so Laura could do her hair. I began applying my makeup. I went with a smoky blue eye shadow and a luminous red lipstick at Laura's request. When finished I pouted my lips and let Laura inspect my work. "Perfect, Jacki."

Laura finished her makeup and then we started the process of getting dressed. We removed the costume and examined our purchase. The top was royal blue with red piping, and had a halter top design with large white collars with little sequined red anchors. I was delighted that the top allowed me a decent amount of lift and pushed my small breast up maximizing the little cleavage I possessed. Laura on the other hand was virtually spilling out her top, the fabric struggling to contain her large breasts. "Damn, I should have ordered a size up," she stated as she tried to stuff her tits into the garment. 

"It looks hot on you," I smiled back. The looked down and laughed, "Well I guess it is a swingers party so modesty really isn't an issue." We both chuckled as we continued, "Oh shit, I forgot our panties and stockings," she shrieked before disappearing into her closet. 

She returned quickly with four packages handing two to me, "Here you go, sweety. Let me show you these panties." 

We pulled the red thongs from their packaging and I followed suit as Laura slipped them into place. "You see these," as she fondled two chrome clasps, "these unhook so you can take them off without having to remove your garters. I thought it would be handy tonight." 

"Yes I could see where that might be useful on a night like tonight," I chuckled. Next came the mini skirt, which was the same royal blue, but had "CUM ABOARD" scrolled across the back, and four attached garter straps. Once on the short pleated skirt did little to cover, as my plump ass cheeks were clearly visible. We then opened up our hosiery. They were a white fishnet, with a white lace top and little red bows. The costume came with blue stripper platform sandals. I stepped into the shoes and strapped them on. To complete the look there was a white sailor's hat, with sequined anchor, which Laura pinned in place. 

Laura then motioned me over, "Come here sweety, let's decorate your little accessory." She squatted down grabbing my hips and pulling me close. She had my raise my skirt and she lowered my panties exposing my clitty. She then tied a red satin ribbon around it and tying it off in a bow. She then planted a kiss on its head, leaving a sparkling red lip stick print. "There now we are finished. I pulled back up my panties and straightened my skirt, as Laura stood back up. We stood side by side, checking our reflection in the mirror. We truly looked like mother and daughter now that I sported gorgeous red hair like Laura. As we gawked over our appearance, we spoke in unison, "Damn we are Hot!"

We exited the bedroom arm in arm, walking step for step. Steve was in the den drinking a beer and watching football. He stood at attention and his jaw his the floor when we strode in, "Holy shit, you girls are fucking smoking. I mean WOW!!"

Steve wore a short sleeved Navy officer's uniform and matching hat. 

We both laughed and teased Steve, "I don't think you will be able to keep the boys off of us."

"That may be, but I know I think I know where you girls will be spending the night," he quipped as he pulled each of us to his side and softly kissed each of us.

It wasn't long before the help started to funnel into the house and began setting up at their responsibility. I helped Laura doll out the responsibilities and make sure everyone knew where and what they were supposed to be doing. Steve did his best to help by drinking beer and continuing with his football game. "Steve turn that off and get in here and turn that off, our guests will be arriving shortly," she snapped. 

He reluctantly complied and joined us in the main room, "Come help me with the food," she motioned to Steve. She then grabbed a sheet of paper from one of the door greeters and handed it to me, "Have a drink at the bar and look these over, we will be back in a minute."

"Ok, I could use a drink," I replied. 

I walked to the bar and ordered a glass or red wine from the bartender and began looking over the paper. At the top the paper read: Party Rules, 1. NO means NO, any member has the right to refuse to play with another they don't want to. Any violation will result in immediate removal and expulsion from membership. I took a drink from my glass as I read further. 2: Absolutely NO drugs are allowed on the premises, Any person found to have any illegal drugs in their possession, will be removed from the party and removed from future events. 3: Be courteous to the staff, they are not hear to participate, but to serve. 4: Have FUN and fuck till you hearts content. 

I smiled at the last line and took another drink as Steve and Laura returned, and then joined me at the bar. They ordered a drink and then Steve offered a toast, "To Jacki's coming out Party." 

Laura then toasted, "To my darling Jacki."

I raised my glass to meet theirs, "To Me."



Jacki's Journey into Sissyhood Pt. 05



We finished our drinks and talked in excitement about the forth coming party. Steve then caught the glint of headlights as they turned up the driveway. "I better go make sure the valets get started parking the first cars right, or we will never get all of them in here." Steve sat down his beer and headed for the door, "Be back in a minute girls."

Seeing the lights of the arriving guest set off my nervous butterflies. I turned to Laura, "I need to tinkle real quick, will you come with me?"

"Of course darling, let's go," she answered and grabbed my hand and led me on. 

I pulled down my panties and sat down and began my business then asked Laura apprehensively, "Laura, are there going to be any other girls here like, well you know like me."

Sensing my distress Laura squatted down in front of me and took my hands in hers, "Baby, what's wrong."

"I just was worried someone might find my, you know, and think I was a freak or something. I thought I might feel better if there were other girls like me here," I muttered. 

Laura looked me in the eyes and said, "No honey, no one is going to think you're anything but a beautiful young woman they would saw their arm off to be with. Trust me."

I let out a smile, "Thanks Laura I needed that." 

"My pleasure baby," she replied and wrapped me in a hug, "now clean yourself up and touch up your lipstick, I need to pee too."

I wiped my clitty, then stepped in front of the mirror, and began reapplying my lipstick. "You forgot to answer me about whether or not there would be other girls like me here."

Laura wiped herself and pulled back up here panties, "Well there usually are, usually the members have 6 or 7 other t-girls on the list."

"What about other sissies, like me," I interjected. 

"You haven't been a sissy for some time now Jacki," she said. "Sissies are men who dress up as women. Darling you've been a woman for some time now."

"A woman with a little something extra," I laughed back.

We both giggled and finished touching up our faces, Laura then took my arm and said, "Come on lets go have some fun."

As we strutted down the hallway, we could hear music and laughter, as guests filed in to the main room. There were about 50 or so people already there and more pouring through the front door at each second. I saw Steve talking with Mr. Conner who was dressed like a football player, and Tara and Courtney were at each arm dressed as sexy cheerleaders. 

Tara spotted us as we bounded into the room arm in arm. "There are the two hot redheaded sailors we have been looking for." 

The four of us girls shared a hug as we complimented each other's costumes. "I love Jacki's new hair, you guys look like a hot mom and daughter pair," Tara said. 

"Well you two girls look fab, and so hot and cute," I replied. We all giggled, drank, and danced as the room began to fill. 

Steve brought a man over to introduce me to later. The man was quite good looking in the rugged lumberjack kind of way, and looked to be about my age. He wore a pirate costume that exposed his chiseled stomach, my ass puckered in excitement as he shook my hand and Steve introduced himself. "Jacki, this is Mark. He's an architect I work with, and an old golf buddy. Mark this is Jacki, she is an accountant for me, and has been staying in our pool house."

"Nice to meet you, Jacki." Mark said. 

Steve then said, "Why don't you two chat, I'll go get us a drink."

We talked for a bit, and Mark told me how pretty I looked, that made me blush a little. He had used to live here in the city, but had moved up state a year ago, but he was down this way quite often for work. The party began to fill up to capacity, and before long Mark saw a friend he needed to talk to, and turned to me saying, "Well it was lovely to meet you Jacki, hopefully I'll see you later?"

I looked at him coyly, "Maybe."

He smiled and winked at me, then walked away. Courtney then took his place, "Who was that hunk, you officially have me jealous." 

"Oh that's one of Steve's friends Mark," I replied. 

"Well if you don't take him, I'll gladly let him fuck the hell out of me," Courtney growled. 

I retorted, "I saw him first, dibbs."

By 7 the place was jam packed full of people of all shapes sizes and races. There was scarcely room to move, but from what I could see there seemed to be 3 women for every man. When the last couple of the evening arrived, the front door was closed, and Steve took to the microphone, and waved me and Laura up on the stage. Laura and I walked up to cat calls and whistles from the crowd. I felt a little embarrassed by all the attention, but Laura pulled me close as Steve began to speak. 

"I'm Steve Clark, and Laura and Jacki and I would love to welcome you all to our annual Halloween bash." The crowd erupted into cheers, after his opening. Once they settled down, Steve continued, "Most of you have been here before, but for the newbies among us just ask around if you need anything. Remember your rules, and most importantly have fun." He turned to us and took Laura's hand, "Without further a dew, let's get this party started." The DJ started the music back up as everyone cheered and danced. As we dismounted the stage I could see people begin to start filling out to other parts of the house. Laura and I were met by Tara and Courtney and yanked out on the dance floor. We danced around in the mob of people, grinding and dry humping anything that came up behind us. 

Slowly the party began to move from the main room to other spaces, and the dance floor began to clear out. I saw Steve being pulled towards one of the hallways by two young blondes dressed as naughty nurses. I had lost track of Tara and Laura in the mob, but I found Courtney grinding away on a middle aged man dressed as a vampire. I decided I would get a drink and see if I could locate the other girls or better yet Mark. I got another glass of wine, and fended off a couple of advances by other men, because I wanted to make Mark mine. I searched the crowd, as people filed out, but with no luck. More worryingly I now couldn't find Courtney. I settled in and danced a little more and waited to see if they turned up. After 5 minutes I decided they all had probably began having fun, without me. 

I decided I might as well do some exploring. I entered into the dimly lit corridor and could instantly smell the scent of sex. Everywhere I looked there were various couplings fucking in in lustful exuberance. I continued exploring to see what I could find. It seemed like each room had a different theme. The small formal dining room, was full of women fucking one another, the writhed and moaned in passion in various positions. Roxy, the pink haired girl, from the tattoo parlor was wearing a strap-on and hammering away at Tara's moist pussy, with a large strap on cock. Tara saw me watching and blew me a kiss, as Roxy fucked her silly. Well I had found one of my friends, I decided to continue on further. 

In a sitting room, there were about 10 or 12 men all together having a gay sex orgy. I caught sight of Mr. Conner fucking a dark haired twink in a jock strap on a couch. His long cock was pounding away at the boys, smooth hole, while he had his lips around another man's pole. The blonde man who Greg was sucking, then pulled his cock from Greg's hungry mouth and joined the two on the couch. He positioned himself behind Greg and slowly pushed at his back. Greg bent over and began making out with the twink he was impaling, stifling his moans. The blonde man then began to squeeze his cock into Greg's exposed orifice. He slid into Mr. Conner and they rocked together, as Greg's swollen cock was buried in the twink, as the fair haired stud at his back powered away at his hole. The scene was pretty hot, but I decided to move on further. 

Next I came to the den, where I found Laura. She was surrounded by 3 ebony studs. One laid on the ottoman, as she straddled him. He had his hands on her hips and bounced her up and down on his glistening shaft. The other two stood at her side with each of their massive black cocks in her manicured hands. Each one of them was at least 10 inches long, and so thick that her hand couldn't completely envelope their girth. From the visual of her stretched pussy the black stallion she rode, was every bit their equal. As she rode her African lover, her now exposed orbs bounced freely, as the two other men pulled at her nipple studs. 

The man that hammered away at her sweet cunt was talking dirty to her, "Damn L, you a true black cock bitch ain't you. You love this black dick don't you baby." The two other men joined, in unison, "yeah freak this black cock hoe, Fuck dat pussy up Tyrone." 

Laura's eye's glassed over in lust, as she came on the black dick stretching her snatch. She moaned, "Yes T, fuck my pussy, baby. Your big black dick feels so good fucking my white pussy, Oh god yes, fuck me, fuck me, give me your black nigger dick." 

"Here you go bitch, here that nut," Tyrone slammed her down once more and drove his pole deep into Laura's womb where he emptied his seed. "Damn L you a freak, hoe. You done creamed yourself on my dick again." 

Laura shook as the act of Tyrone filling her pussy caused her to orgasm again. She eventually rolled off Tyrone. He then stood up and walked over to two young white girls, and told them, "Be good white bitches and clean my dick for me, before I fuck you both." The two girls grabbed his rod and greedily lapped at its length. 

The two other black men then returned Laura to the ottoman, this time in doggy position. "I get this pussy next, L you suck his dick while I tear up your white ass," one of the men instructed. As they situated her for another round, she caught my stare. Laura gave me a horny grin and a wink, before she was penetrated from behind and a cock was shoved in her mouth. 

I turned to move on and a hand grabbed my ass, I turned hoping to find Mark, but instead I found a short man dressed as batman. "Damn, what a fine ass," the short man said with a slightly Spanish accent. He was a middle aged with a dark mustache, and not completely unattractive. 

"Would you like to take this party somewhere private," he questioned. I was horny as hell after watching Laura be pounded into submission, but I really wanted to find Mark. But in this crazy atmosphere who knew if I could. 

I bent down and kissed him on the lips and he returned my advance, or tongues wrestled as his hands explored my body. He was a good kisser, so I thought to myself, he will do. His kisses moved to my neck as I whispered in his ear, "I need you to fuck my ass hard."

That was all the encouragement he needed. Then led me down the hallway trying to find a spot. We finally found a room that was unoccupied and set to work. He went to close the door behind us before I stopped him, "leave it open baby."

He complied with my wishes, and he kissed me firmly as he pulled me close. His hands returned to kneading my ass, as mine massaged his stiff cock through his tights. I finally broke his kiss and allowed myself to drop down his body to my knees. I licked at his cock through the tights as he began to moan, then I hooked my hands into his tights, pulling them down and setting his member free of its confinement. His cock wasn't all that long, maybe 5 inches, but had quite impressive girth. I wrapped my ruby lips around his prick and took his manhood into my mouth. He must have been quite excited, because within a couple of minutes he was close to blowing his load. He pulled me to my feet and kissed me, "Let's see that beautiful ass." 

I then crawled on the rubber covered bed, and removed my thong and placing it beside me. He then pushed at my back and I went down on all fours, and lifted my skirt exposing my hole and clitty. I guess my little appendage didn't bother him to much as he dove face first into my hole. "Damn, you taste good baby," he muttered into my horny pussy, as he lapped ravenously at it. I let him continue to lick my now moistened rosebud until I just couldn't take it anymore, and I pushed his head back from my ass. He looked up at me disappointed, as I said, "No more tongue, I need a cock now." 

I crawled forward and allowed him to join me on the bed. I handed him the bottle of lubricant from the nightstand and offered him my ass. He greased his cock and then prepared to mount me from behind. His width proved to be an issue, as he struggled to push his dick into me. I relaxed and pushed out hard with my ass, and finally my anus accepted his cock. He quickly submerged himself in my rear, and slowly fucked my ass back and forth. His length left a little to be desired, but when the slammed himself into me hard, his wide head would rub my p-spot causing me to moan. We fucked back and forth, before he began to moan, and grunt. I then felt him spurt his hot seed into my rectum. He collapsed back on the bed and I spun around and took his cock into my mouth, sucking the last remnants of cum from his penis. He got up and pulled back up his tights, as I noticed Roxy in the hallway flicking her clit. The short man exited and I waved her in. She came in the door, and commented, "That was so hot, I hope you didn't mind me watching." 

"Well since you got a free show, how about you clean me up," I said scooting my freshly fucked ass to the edge and lifting my stocking covered legs. Roxy dove in and lapped at my creamed hole, cleaning it of the leaking cum. She moved back and I sat up bringing my mouth to hers. Her hand pulled at my nipples as we swapped the creamy treat back and forth. She broke the kiss, "these turned out nicely," she commented as she tugged at my nipple rings. She kissed me once more, and said, "Thanks babe," before turning to leave. After she left, I stood up and grabbed my panties. I tried to fool with the clasps but ultimately said to hell with it and stuffed them in my top. 

I walked out to find Courtney, walking down the hallway, "Oh there you are I've been trying to find you." We embraced each other and kissed. I could taste cum on her breath I wondered if you could taste it on mine. 

"I need a drink, how about you," I asked. 

"Lead the way girly," she answered. We walked hand in hand back into the main room. As we did I felt more cum leaking from my pussy and beginning to run down my leg, I thought it best not to draw attention to it. 

We found Laura, and Tara taking shots at the bar in the main room. They saw us and said, "There are our girls, I hope you two are having some fun." They passed us jello shots and we all downed them, then we were passed two glasses of wine. I drank half of mine in the first drink. 

Laura cautioned, "Slow down darling this goes all night." I laughed back, "I know I just worked up a thirst." 

Laura, I could tell had been having fun. Her stockings were shredded, she too was going commando as her cum soaked panties were wadded up in her bra, her red hair was tossed about and her sailors cap was long gone. Her inner thighs glistened with excess black jizz. Tyrone walked up behind her and wrapped her arm around her. "Damn L when you gonna let me have a piece of that white cookie," he asked motioning towards me. 

"Oh no, her delicate flower is not ready for the mandingo group," she laughed. "Plus that means id have to share some of my black cock, and you know how bad I am at sharing," as she groped his massive member through his basketball shorts.

"True dat,"he replied. "So you think your pussy be ready for round two, the boys are getting anxious."

"Sure I'm ready," she chirped. 

"I think I'll tag along if you don't mind Laura," Tara added. 

Laura looked at her, "Ready for some dark meat are we?" 

"As they say, when in Rome," Tara replied. They downed another shot and then placed Tyrone in the middle, and his hands on each of their asses. The group walked away leaving Courtney and me at the bar. 

I turned to Courtney, "Tara won't walk right for a week, I mean cocks like this," I held out my hands demonstrating Tyrone's endowment. 

She giggled, "Not my pussy, I'm not that much of a size queen I guess. Like 8 inches is the max, 6-7 inches is perfect for me."

"Same here," I said as we drank. 

"Speaking of cocks, I met two cute guys earlier, while I was looking for you. They said they wanted to dance, I told them I would meet them here once I found my friend," she explained. 

"Ooh that sounds fun," as I bent down to fix my shoe. When I did, my panties fell out of my top. Courtney picked them up and looked at them. She then took her other hand a put it under my skirt, fondling my naked clitty, and then feeling the sticky cum on my inner thigh,

"Your dirty girl you," she exclaimed, "Was it Mark?"

I sighed in disappointment, "Sadly No, I haven't been able to find him actually."

"Well I'm sure he will turn up," Courtney consoled. "Oh look there they are."

Courtney waved to someone across the dance floor. Two tall guys in firemen's costumes began to make their way over to us. Both guys were about 6'4" or so and looked like they could be brothers. Both boys had an Abercrombie model look to them, and with nothing on underneath their fireman's coat they both sported a delicious set of hairless abs. "Oh my," I cooed as they approached. 

"They are young and kind of dumb, so don't let them talk too much, but they are nice pieces of man candy," she chuckled as she sipped her drink. 

"So ladies, we heard there was a fire over here that needed to be extinguished," the one on the left said. 

Courtney was right, total idiots, I thought to myself. "Hi boys, this is my friend Jacki. Jacki that is Brad on the left and Curt," Courtney said as she introduced us. "Why don't you guys grab us another drink and we can do some dancing." The boys nodded and went towards the bar.

"See what I meant about not talking," Courtney laughed.

"Yeah no kidding, but they are both incredibly hot though," I added. 

Courtney then got serious, "I figure our best shot is to pull them out on the dance floor, dance for a while and then find a loud place to have them fuck our brains out." 

"Sounds like a deal, as long as we don't have to carry on a conversation with them we are good," I agreed. "But if I find Mark it's all on you."

Brad and Curt returned with our drinks and we promptly pulled each out on the dance floor. We danced our little hearts out grinding away on the guys crotches. Curt was fond of playing with my ass under skirt while we danced. I was a little buzzed from my drink, and very horny now from playing with Curt's rock hard body. I gave Courtney a wink to signify I was ready. We grabbed the boy's hands and dragged them towards the rooms. I caught a glimpse of Mark being led out by two brunettes. I considered chasing him down, but It was probably too late. Oh well, I thought, maybe another time. 

We wondered the halls with our boy toys in tow looking for a room. We walked around for a while before catching two couples exit a spare bedroom. I told Courtney, "I think that room has a stereo in it." 

"Perfect," she replied as we led the boys in. The room was now empty, so we entered bringing the boys in behind us and closing the door. I pointed Brad towards the stereo control on the wall, "Brad, why don't you find us some music, and turn it up loud."

Brad nodded in agreement, and Courtney and I entered the attached bathroom. As hip hop started blaring, I said, "So far so good." 

Courtney laughed in return as she removed her panties, "Won't be needing these now." 

I took off my top exposing my breasts. "Good idea Jacki, I'll go topless to. Less work," Courtney asserted. 

Once we were ready we entered the bedroom and looked at Curt and Brads hot bodies, Courtney then shouted, "Now lose the clothes boys."

Both Brad and Curt shucked their clothes quickly and stood naked before us. They're chiseled frames were immaculate and they're half hard cocks were glorious. We both attacked the boys dicks, on our knees in a flash; Courtney on Brads cock, me on Curt's. We sucked at their tools breathing life into them in short order. Curt was a little longer than Brad around 7 inches at full mast, But Brad trumped Curt in girth. I was so horny, I jumped to my feet and kissed Curt deeply and led him to the bed by his cock. 




Jacki's Journey into Sissyhood Pt. 05



"Lie down on your back," I ordered. He complied with my wishes, crawling on the bed and laying with his cock up. I picked up the lube from the table and lubed my hole, then added some to Curt's rod. I then straddled his prick and used my hands to guide it home. Curt's greased member easily slid into my waiting pussy, and I dug my fingers into his abdomen as I began to ride him. His cock felt amazing, as he rubbed my prostate as I bounced. My partner rocked his hips driving himself into me in sync with my hips. He was as adept at fucking as he was at dancing. 

Curt then sat up and wrapped him muscular arms around my hips, and placing his lips on mine. We made out as I rode his erection. His mouth moved down my body, and began suckling at my tits. Curt's tongue danced with my nipples as his cock kissed my prostate. I wasn't long before I was screaming myself through an orgasm. I came hard, while riding his dick. 

Not wanting the joy to end, I rotated myself into a reverse cowgirl position, getting myself up on my heels, and leaned back to brace myself with my hands. Curt then began hammering away at my pussy once more. 

I now could see Courtney, who was on her hand and knees on the bench in front of the bed facing me. Brad was behind her pounding her vagina. I could tell she was getting close by the expression on her face. I watched as my girlfriend was fucked into a state of bliss by her partner. 

After her orgasm I looked at her and said, "Wanna switch." 

She smiled and nodded yes.

I dismounted Curt's cock and pulled Courtney onto the bed. She immediately mounted Curt and lowered her cunt onto his cock. 

I laid on my back beside Curt and Courtney, and spread my legs offering my vacant hole for Brad's erection. He eagerly climbed up and filled my void. Our foursome fucked to the beat of the rap song that played. My ass milked Brads cock and I felt his pace quicken. I stopped him and pushed him free from my ass, as I wanted him to finish in my mouth. I rocked forward onto my knees and engulfed his rod with my mouth. I bobbed up and down on his cock tasting the combination of my ass and Courtney's pussy. Brad moaned and shot his load into my mouth. His creamy sperm I greedily lapped down, as I cleaned his beautiful penis. 

Seconds later Curt exploded inside of Courtney's cunt. After the boys came they got dressed and exited the room leaving Courtney and I panting on the bed. Courtney's used pussy, had started to leak out Curt's seed onto the rubber sheets. Seeing this I positioned myself between her thighs, and licked at her swollen labia. I lapped up Curt's nectar and then crawled up Courtney's naked body and kissed her. 

She smiled and kissed me back, "That was delicious, we have to do this more often."

We laid on the bed and recovered for a few minutes before gathering our clothes and exiting the room. Since the majority of the party had already left and most of our clothes were soaked in either pussy juice, sweat, or cum we didn't bother getting dressed and instead walked back to the main room, only wearing our skirts and high heels. 

The last few couples exited, as we entered to find Steve, Greg, Laura, and Tara talking. The women were completely naked except for their high heels, and Laura's ripped stockings. Steve and Greg only wore shorts. 

"There those two are," Laura exclaimed. 

"We were beginning to think you had been kidnapped." Tara added. 

Courtney and I just smiled and shared a laugh. 

Greg looked at his watch and looked at Tara and Courtney, "Girls we should probably be heading home."

Tara quipped, "Like hell, we are still horny Greg." 

Laura then chimed in, "Us girls are heading to the master. Once you boys get the help out the door come and join us." 

Steve and Greg, agreed and set to helping the staff cleanup. Laura looked at Courtney and me and said, "Come on you two dirty sluts, follow us." Laura grabbed Tara and the two locked arms and strode off towards the master, as their naked asses bounced. Courtney and I followed suit of our mentor counterparts. 

All four of us climbed into bed and made out for a while, as we waited for the boys. Greg and Steve finally joined us and they sat at the side of the bed. Laura then said, "Well Courtney and Jacki, me and Tara saved you guys a little present from Tyrone and the boys." They spread their legs to reveal their pussies were covered by those latex bandages that Laura had used before. 

"How many loads tonight darling," Steve inquired 

"I have 6 here," Laura answered as she tapped her mound, "Tara's little pussy only held 4." 

"Now girls this surprise came directly from Tyrone and the boys, they said if we fed you all the black cum it would surely turn you into black cock sluts like us. I don't know about that but Tara and I just want our pussies eaten." 

We crawled onto the bed together, Laura said to Courtney, "You come to me, Jacki you're with Tara."

I crawled myself in between Tara's thighs and positioned myself with my hands beneath her large ass. Tara then looked at me ordering, "Don't miss any darling," then removed her latex covering. Immediately her ravaged pussy began to gush and ooze with black semen. Tara grabbed my hair and slammed me face first into her used vagina. I lapped at the black seed that flowed from Tara as the boys stroked at their cocks. Steve quickly got hard and took positon behind Courtney preparing to stretch her with his massive erection. She squealed into Laura's ebony fucked pussy as Steve's girth stretched her tight pussy. 

Greg was unable to get himself hard quick enough, and resorted to rimming, and finger fucking my ass. Laura saw this and dug into her night stand throwing him a large silicone dildo, and said, "Here Greg, fuck her with this." Greg obliged her requests, he quickly lubed the phallus and then began working it into my hole. The fake cock quickly slid into my rectum as I sucked at Tara's pussy. I finished cleaning her pussy of all it's cum, and then turned my attention towards her clit. Greg knew where to find my prostate, and used the plastic dick to fuck my spot. 

I worked Tara into an orgasm, as I did she pressed my face harder against her button, and screamed, "Fuck, Fuck, Oh god yes," before squirting her juices into my pretty face. 

Tara then pulled my head free, "Flip around and suck my husband's cock."

As I repositioned myself, I saw Steve was on his back while Courtney was riding his cock in reverse cowgirl. Laura had her face in-between their legs, licking at Courtney's pussy and Steve's shaft as they fucked. 

Greg gave the sex toy to his wife, who resumed my fucking. I took Greg's soft penis into my mouth, and began to nurse his hardon back. I licked and sucked at his cock as it began to harden in mouth; meanwhile his wife worked the dildo in and out, removing it often to observe my gaping hole, which she would spit in before my ring closed. When Tara saw that I had worked Greg's cock back to full mast, she grabbed my hips and pulled me back off his cock and into her lap. She looked at her husband and his now hard cock, "Give her your cock baby, fuck her good." I scooted my ass forward resting my head on Tara's chest. Greg moved into position and lifted my legs so he had access to my ass. His swollen cock slid easily into my pussy and he slammed himself into me, bottoming out. He fucked me hard,the way he had fucked the boy on the couch from earlier. 

I moaned and sighed, "Oh yes, Mr. Conner, fuck my pussy." Tara's rubbed my nipples and added encouragement for her husband, "Fuck her hard Greg, fuck her ass hard baby. 

I looked to the other group in time to see Steve drive the full length of his cock into Courtney's cunt and deposit his load deep inside. The visual along with Greg's cock simulating my p-spot, sent me into orgasm and my muscle's squeezed his manhood as I came. Greg fucked my clenching anus harder as his breathing quickened. Tara could see he was close, and grabbed his head pulling his lips to hers. They shared a kiss, and then she ordered, "Breed this slut Greg." He gladly followed her demands, driving himself into me harder. Greg grunted and drove into me as he spilled his seed inside of me to the cheers of Courtney, Laura and Steve. 

Greg held himself inside of me while he caught his breath as he began to soften, "Holy fuck, her ass is good."

Steve agreed, "Jacki's pussy is incredible, Courtney's was as well."

We all slept together in Steve and Laura's bed in a naked, sweaty, cum covered tangle. 

The scent of sex lingered throughout the house, for over a week. I breathed it in reveling in the olfactory reminder of my cumming out party.



Jacki's Journey into Sissyhood



He then positioned himself in between my legs, aligning his weapon of ass destruction up with its target. I jumped a little as his soft cock head probed my entrance. I was full of lust, as I whined like a bitch in heat, "Pop that cherry daddy." 

He slowly applied more and more pressure as he tried to impale me. The pressure was intense, and I tried not to fight it. I was beginning to think his swollen penis wasn't going to fit, when the enormous head popped free. I gasped in pain as I pulled Steve close and clamped down my sphincter mussels around the invader. He softly whispered in my ear, "Relax baby, Daddy isn't going to hurt you. Just relax and the pain will subside." 

I tried to relax and as I did the throbbing pain in my ass slowly waned. With a tear in my eyes, I whimpered, "Ok daddy, I'm ok."

At my ok, Steve began to slowly push further into my depths. Slowly he fed his serpent into my sissy hole until he was all the way in and I was completely filled with man meat. He held himself deep inside of me, allowing me to adjust to his size as he kissed me intensely. Gradually my ass began to loosen and when he felt my death grip on his penis subside he began to slowly withdraw his cock about an inch and the replace it. I began to groan through our kiss as his body began to undulate on top of mine. 

As I moaned, "Oh, daddy," his pace began to quicken and his strokes became longer. He would guide his member half way out then bury it to the hilt in slow smooth motions. As he withdrew and entered his cock began to stimulate something a spot in my bowels. The motion of slow love making caused the stimulation to grow ever more intense. As with the tongue bath early, my clitty once again began to leak. 

Steve then broke our make out session, and pushed himself up and guided my legs up before pushing them down and commanding, "Grab your heels baby, daddy's about to make you his woman now." 

I grasped the heels of my pink pumps as Steve set to work. His thrusts became faster paced and longer as he pistoned in and out of my tight pussy with his cock. "Oh daddy, yeah fuck that pussy," as his battering on my ass began. Now as he finished his stroke his nuts were slamming into my ass like little wrecking balls. I sighed and gasped encouraging him on, "Fuck me daddy, make me your slut, your cock feels so good in my pussy, Fuck me Daddy, Harder, Faster."

"God yes, your fucking slut hole is so god damn tight baby," he exclaimed as he hit another gear. 

At this point he was slamming my ass with his rod. As his thrusts quickened so did the stimulus of prostate. After of couple about 5 minutes of fucking, I erupted, "Oh God Daddy, I'm cumming!!, " as my clitty began to spurt copious amounts of cum that began puddle on my lace bustier. 

My climax must have sent Steve over the edge, "where do you want my load slut." 

"Cum in me daddy, fill me up, make me a real slut," I encouraged. 

He yelled, "Here it comes slut, oh shit,..., Ohhhh, Gawdddd." He slammed his cock home, and I felt the shaft spasm. Then his testicles unleashed a torrent of cum into my pussy. The cum just never seemed to stop, as his ball unloaded their payload, and soon is was full with cum squirting from around his cock and leaking out onto the bed. 

We laid there gasping for air, covered in sweat and jizz, in all our post fuck glory. Steve finally broke the silence, "Now that was hot a hell, baby."

I echoed his sentiments, "I've never came that hard in my life." 

Steve's softening cock slid out of my well fucked love tunnel, with a loud suction sound, like removing a rubber boot from a mud hole. As he removed the obstacle, cum began to spill out of my overfilled ass. Steve quickly grabbed my plug reinserting it into me to stop the flow. He looked at me with a sly grin, "That's I lot of cum baby, you might want to save that as a souvenir or something."

I laughed, "Yeah I guess so, how about a taste."

Steve took his hand and swooped up the cum puddled in my ass crack and shoveled it into my waiting mouth. Having never tasted cum, I was unsure what to expect, but it wasn't bad. Slightly salty, slightly sweet, thick in a gelatinous consistency and a hint of vanilla which I suspect was from my body lotion. I finished cleaning Steve's fingers, then he kissed me deeply as we swapped the cum back and forth. He broke the kiss saying, "That was delicious."

I nodded in approval. 

Steve looked at the clock, it was now 1:30 in the morning. "Man it late, I guess I should go." 

I grabbed his arm as he turned to leave, "or you could stay."

"Are you sure?" he asked. 

"Of course daddy, we can cuddled," I laughed. 

He laughed back and kissed me once more, "Ok if its ok with you, I'll stay."

"Yay," I exclaimed. "I guess I should cleanup for bed," I said popping to my feet and trotting towards the bathroom. I looked back at Steve lounging on the bed, "make yourself comfortable, I'll be right back." 

I kicked off my heels, and threw them in the closet before trotting into the bathroom. I quickly stripped down. Using a washcloth I quickly washed the sweat and cum from my body, and reapplied some lavender body lotion. I removed my old makeup, then quickly reapplied some simple makeup to my face, and some clear lip gloss to my lips. I then began to rummage through my closet. I found my white silk and lace babydoll and matching panties, and quickly got dressed. I brushed my teeth, tossed my wig about then opened the door to the bedroom. 

Steve had made quick work as well, blowing out all the candles, and retrieving his boxers. He was now partially under the covers watching TV. He rolled over when he saw me and said, "Wow, well aren't you dressed like my little sissy bride."

"Kind of the look I was going for," I laughed. 

He lifted the covers up for me allowing me entry. I slid in beside him as he cocooned me in then wrapped his arms around me, and giving me a soft kiss on the lips. "I hope you enjoyed yourself tonight Daddy?" I enquired. 

"I'm still here aren't I?"

I smiled and he kissed me once more. We fell asleep in each other's embrace. 

TO BE CONTINUED...