7 comments/ 74559 views/ 12 favorites My First Time Dressing Ch. 01 By: ChrissyCD This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdresser to a full blown crossdressing slut. They will all be true and uncensored which is the way I have lived them. It covers the secret life that I have lived for the past 20 years and still do to this day. Please vote and I hope you enjoy the stories as much as I did living them and reliving them as I write them for your enjoyment. I started dressing in women's clothes shortly after high school. I didn't really go all the way buy usually just pantyhose, bras, and panties that I would borrow from my mom or sister. I had experimented with it a bit when younger, stealing my mom's pantyhose and jerking myself to incredible orgasms while wearing them. I loved the feeling of the silky smooth nylon on my legs and cock. I would occasionally put on one of her night gowns with the hose, the feeling of the satin touching the nylon hose would drive me nuts and I would just lay on the bed and roll around rubbing my legs against the gown. When I went off to college I was able to explore my fondness of all things soft and silky even more. I had a roommate but he would leave every weekend to go home to Houston and I would have the whole place to myself. This is when I first really started to "dress up" and be the woman I desired to be. I skipped class on a Friday and drove to Houston. I went to a lingerie store and bought myself some really sexy gear. I remember it like it was yesterday. I bought a red lacey "Wonder Bra", matching thong, garter belt, and a pair of black lace top thigh highs. I found a sexy red strappy spandex type dress that was short, but not too short, maybe about 3 inches above the knee and had a sexy slit up the side. I went to the counter to pay and the lady looked up at me and smiled. She told me that who ever I was buying this for sure would like it. I just smiled back and said I hope so, it's for a special night. She sort of giggled and said that she hopes she likes it and placed it in tissue paper and then slid it in a bag for me. I got in my car and drove off looking for a shoe store to buy some girly shoes. I went to a Famous Footwear store and went in. I browsed around trying to look inconspicuous in the women's shoe dept., without much luck. An older lady came and ask if I needed help. I told her no I was just looking, she smiled and walked away. I looked around and found a foot scale to see what size I wore in ladies. I checked my foot and went to the size 11 section. Apparently women who wear size 11 don't have a lot of choices for sexy shoes. I did manage to find a pair that would do. They were a pair of red velvet sandals with thin straps, a 3 inch heel and ankle strap with a buckle. I grabbed them and went to the end of the aisle and tried them on real fast, snug but they worked. I went to the counter to pay and when the lady saw what I was buying she just grinned at me and rang me up. As I was walking out I could here her and another lady giggling at me. I got in my car and drove to another parking lot to examine my purchase closer. I took out all my stuff and laid it out on the seat next to me so I could see it all. I took out the stockings and rubbed one on my leg. The feeling was electric! I kicked of my sandal and pulled one of the stockings up to my knee. I took one of the heels and slid my foot right in and buckled the strap. The nylon sure helped my foot glide in the shoe, and the look of that shoe on my foot was so erotic. I tucked everything back in it's bag and shoes in their box and drove home thinking of what laid in store for my evening. When I got home I scanned the parking lot for my roommates car. It was nowhere to be seen so that meant that he had already left for Houston. I grabbed my stuff and ran up the stairs. I was so nervous with anticipation I could barely get the key in the door. I got in and locked the door with the deadbolt and the chain. I went to my room and stripped to my boxers. I took all my new clothes and took the tags off and neatly laid them out on the bed. I went to the kitchen and grabbed a beer, went back to my room and sat in a chair with a raging hard on drinking my beer and staring at the wonderful outfit laid out before me. I drank a couple more beers and smoked a half a joint while watching some porn. Remember we are college guys so there was no shortage of booze, weed and porn around our apartment. I sat there for about an hour and finally decided it was time. I went and took a nice hot shower, dried off and blew dry my hair. I blew my hair upwards so it would have a full look to it. (this was the 80's and my hair was about 4 inches past my shoulders) I teased it up a bit on top and sprayed it with hair spray doing the best I could at feminine looking hair. I walked into my room and took the bra and wrapped it around my waist, spun it around and pulled the straps over my shoulders. I walked to my dresser and got a pair of tube socks and rolled them up nice and round and placed them in the cups of the bra. It felt so good, just enough wiggle from the water in the "Wonder Bra" and the softness of the socks to feel somewhat like real tits. I went back and sat in the chair and slid the stockings up my arm and pulled them down so they were bunched up at my hand. I put my foot in it and slowly pulled it all the way up my leg and then I did the other. I rubbed my legs together feeling the nylons against my skin. I took the garter belt and put it around my waist. I clipped the clips to the tops of my stockings and checked in the mirror to make sure they were straight. They weren't and I had to repeat this about 4-5 times before I got it right. I sat down and leaned over sliding my hand up my legs from the feet pulling the stockings snug and then adjusted the straps tight. I slid the thong up my legs and over the garter belt straps. This is how I saw the girls in pornos wear them so that's what I wanted to do. Be a porno slut. I reached over and grabbed the heels and slid my foot into one and buckled the thin strap around my ankle. I looked down and admired my leg with a sexy shoe and stocking covering it. I put the other one on and stretched my legs out in front of me and stared at them. I felt so sexy and feminine; my hard on was raging and oozing pre cum into my new thong. I stood up on very wobbly legs and walked to the full length mirror on the closet door. I stood there admiring this feminine being in front of me. I turned and looked at my ass, bent over, watching myself in the mirror the entire time. I was amazed at how sexy and girly I felt wearing this lingerie. I practiced walking around the apartment getting used to the heels, which was quite a chore. They were only 3 inches but felt like 6. I damn near fell a dozen times before I somewhat got control of it. I went and got a beer and sat on a bar stool at the bar and smoked a cigarette with my legs crossed like a woman I loved looking at my legs and feet with the stockings and heels, it was so intoxicating. I finished my cig and beer and walked through the kitchen again just to hear my heels clicking on the floor. I went back to my bedroom and got my dress. I held it up in front of me looking at it in the mirror as I held it against my body. I stepped into it from the top and pulled it up my legs and slid my arms through the straps. After a few minutes of pulling and adjusting it I finally had it on right. It fit very well, snug but not so tight that it showed my bra straps or garter belt. The bottom had just a slight flare to it and a nice slit so it hung a little loose on my thighs. I stood there looking in the mirror in a total daze of how sexy I looked and felt. I practiced prancing around wiggling my ass like a slut trying to get comfortable walking in heels. I loved the feeling of the nylons on my legs and the fabric of the dress rubbing the nylons. I was in heaven! I sat on the bar stool drinking beer and smoking cigs for a good hour, crossing and uncrossing my legs. I loved the way the slit in the dress showed just the top of my stockings and when I had my left leg over my right leg you could see the garter belt strap. It made me feel so sexy! I had a real good buzz on so I turned my attention to the TV where I had a good hardcore porno going. I was really getting into watching the guys fuck these girls like madmen. Just watching the girls turned me on so much. I loved how they always wore their thigh highs and heels while getting fucked. I started rubbing my cock through my dress getting myself horny as hell. I would pull my dress up and expose my thong and garter belt shaking my ass and slapping it. I finally couldn't handle it anymore, I had to cum. I had been all dressed up for over 2 hours sporting a hard on for almost all of it. I took off my dress and slid my thong down freeing my aching cock. I walked to the bathroom to get a bottle of lotion while watching my cock swing up and down as I walked. I felt so slutty! I sat on the sofa with my legs spread wide open and cock sticking straight up to my face. (I have a 7" cock, cut and fairly thick that curves upward like a banana) I pumped a couple of good drops of lotion over my cock head and this sent shivers through my body. I slowly started rubbing it all around my head, stroking and pushing it down between my legs so it looked like I had a real pussy when I closed my legs. I started stroking faster and harder while playing with my balls. I was rubbing my balls furiously when my fingers slid between my ass cheeks and I shuddered. I took some lotion and rubbed it all around my asshole. I leaned back and spread my legs wide in the air and slowly started to finger my ass with one finger. It felt amazing when it slid inside me. I fucked myself with one finger, then 2 fingers while pumping my cock. I could feel my load brewing deep inside my balls. I pushed my 2 fingers all the way inside my tight ass and jerked my cock like mad. I felt it coming so I bucked my hips upward and shot a massive load of hot sticky cum all over me. The first shot hit my chin, the second on my neck and the rest, 5-6 more shots landed on my bra and stomach. I pulled my fingers from my ass and slowly milked every last drop from my cock onto me. I lay there totally exhausted and covered in hot man cum. I reached down and rubbed it around with my fingers feeling the sticky cum. I scooped some up and brought my fingers to my mouth, I looked at it for a second or two, then I sucked my fingers in my mouth tasting my salty semen. I closed my eyes and moaned as I sucked my fingers clean. I took the rest of it from my chin, neck and stomach with my fingers and licked every drop from my hand. I laid there totally exhausted but in total ecstasy from the huge orgasm I had just had. I went to my room and slowly undressed the rest of the way. I put my lingerie on a shelf in the back of my closet and hung my dress on a hanger way in the back. I walked over and fell in my bed and went right to sleep. When I awoke the next morning I felt like I had the best night sleep of my life. I walked to my closet and took down my lingerie and stood the staring at it. I felt the bra and smelled the crotch of my thong. It smelled so sexy. I put them back where they belonged, closed the door and went and made me some breakfast. To be continued... My First Time Dressing Ch. 02 This is a continuation from my first story where I bought and completely dressed in women's clothes and started my transformation into a crossdressing slut. Chrissy's First Real Cock After my first night dressed up like a girl I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the thongs felt between my ass cheeks. I had 4 or 5 dresses, mini dresses of course. I bought 3 different mini skirts, 1 denim that was in style then, a black mini, and a red spandex mini with a nice slit up the side. I had 7 or 8 different tops from satin blouses, stretchy tanks, to slutty sheer see through tops. I would dress almost everyday watching porn and jacking myself off to incredible orgasms. I had even bought a few short night gowns and baby dolls to sleep in. I bought some satin sheets and they felt like heaven when I would run them across my stocking clad legs. Besides they made me feel sexy and feminine when I laid on them while dressed. I would make regular trips to Houston browsing my favorite lingerie store & boutique and got to be pretty good friends with the lady that worked there. She had soon figured out who the stuff I was buying was for and became very helpful in getting me the correct sizes and right fit. After the first semester of college was over my roommate decided not to return so I moved into a one bedroom alone. It was fantastic because I could dress whenever I wanted to now. I became fairly good at applying my make-up and doing my hair. I had let it keep growing to about 6 inches past my shoulders. My parents hated it, they told me I looked like a damn hippy. If they knew what I was doing I think my mom would have accepted it. My dad on the other hand, the ex Marine and Vietnam vet would have disowned me. I still only dressed in the privacy of my own place. I hadn't gotten the courage to venture out yet. On one occasion I decided to go to Houston for the weekend and check out one of the adult video stores to buy some new porn. I of course had on my panties and thigh highs under my pants and a nice little satin tank under my sweat shirt. I got there around 9:00pm and was browsing around the store when I noticed that guys kept going in the back through a door. I ask the clerk what was back there and he told me an arcade. I bought the required amount of tokens and journeyed through the door. It was very dark and lots of guys walking around and standing in doorways. I walked through and noticed that there were little rooms with a TV playing pornos. I went into one of the rooms and locked the door. I pumped in a few dollars of tokens and the movie started playing. I sat down on the bench and started watching the flick. Of course I started getting hard and decided that since I was alone in a room I could do a little stroking. I pulled my pants down to my knees and took my shirt off. I started stroking my cock through my panties when I thought I saw something on the wall about waist high. I stopped and focused on the wall, and I saw it. It was fingers poking through a large hole. I was totally shocked. Here I was wearing panties, thigh highs and a satin tank top with someone watching me. I went to the wall and bent down and the guy told me he liked my panties and stockings. I told him thanks. He then hit me with a question that sort of surprised me. He ask if I wanted my dick sucked. I said I guess, and he told me to put it through the hole. I put my cock through the hole and he sucked me into his mouth. I had my fair share of cock suckings, but this guys mouth was amazing. He sucked me for about 3 or 4 minutes before he pulled away. I leaned down to see what happened and then his cock came through the hole. I stared at it for a few seconds then I slowly started licking the head and took it in my mouth. It was a nice cock about 7 inches or so, thick and cut. I sucked for about 4 or 5 minutes when he pulled his cock out of my mouth. He leaned down and our faces met at the hole. He ask me if I wanted to go to his place which was right around the corner. I said sure. We met in the parking lot and introduced ourselves. His name was Todd. I was 19 and he was about 25 clean cut preppy type. I got in my car and followed him to his place. We went in and he offered me a drink, which I accepted and told him to make it strong. We made small talk and finished our drinks. I told him that was the first time I had ever touched another mans cock, let alone putting it in my mouth. He sort of laughed and ask if I liked it? I said yea I did. We went to his bedroom and started to undress. I got my pants and shirt off and started to remove my panties, stockings and little chemise top. He stopped me and told me to leave it on. He stepped close to me and took me in his arms and started kissing my neck and running his fingers through my hair. I started following his lead, doing to him what he was doing to me. He looked into my eyes and then he kissed me. I wasn't sure what to do. My emotions were running wild as I had never touched another man like this. I started kissing him back and pulling him closer to me. Our cocks were rubbing while we made out making me so horny I could barely stand it. He pushed me back on the bed and laid on top of me. I spread my legs open so he had one leg between mine as he caressed my leg running his fingers on my stockings. I laid there and let him take control. He ran his hand up my top and started pinching my nipples while we kissed. He slowly slid his body up so his cock was in my face. I took him in my mouth and was doing my best at sucking him off. I believe I was doing ok because he was moaning and rocking his hips fucking my mouth. He pulled his cock from my mouth and came down and started kissing me again. He got between my legs and I spread them wide for him so out cocks were rubbing one another. He pulled my legs up and started dry humping me rubbing our cocks together hard. He was running his hands up and down my nylon covered legs. He started kissing me hard and humping me faster. I wrapped my legs around his waist and pulled him to me. I did this knowing how much I liked it when girls wrapped their legs around me when I was fucking them. He reached down and pulled my panties to one side and started rubbing his cock on my ass. I had finger fucked myself plenty of times to know that I loved the feeling of something inside me. I had never imagined that one day I would have a real cock inside me. I grabbed his ass and pulled him tight against me, and I whispered in his ear that I wanted him to fuck me. He ask if I was sure, and I told him yes. He got up and went a got a bottle of lube and had a small brown bottle of something else. I ask him what was in the brown bottle? He told me it was a popper and he took the top off and inhaled deeply in one nostril, and then again in the other and held his breath. He handed me the bottle and I did the same. When I let my breath go I was so dizzy and light headed I thought I was going to faint. Then as the immediate rush passed I felt so relaxed and uninhibited. He pulled my panties down and licked my cock a few times while he was down there and then told me to get on all fours on the bed. I got on the bed in the doggy style position and he rubbed lube all around my ass and pushed a finger inside me. I eased forward a bit as he pushed and he grabbed my hips and pulled me back and said to hit the popper again and relax. I hit the popper again as he pushed a second finger inside me slowly pumping them in and out of my ass. It felt absolutely wonderful. I could feel my ass relaxing and giving less resistance to his fingers. I felt him remove his fingers and grab my hips pulling me to him. He rubbed his cock up and down the crack of my ass spreading the lube all over his cock. He took one hand off my hip and I felt him pressing his cock against my hole. It was much bigger than his fingers and I could feel it start to push inside me. I leaned away because it started to hurt a bit but he pulled me back and said to hit the popper again. I took 2 or 3 good sniffs in each nostril this time making my head spin, when I let my breath go I was so high I almost collapsed on the bed. I felt him push his cock against my ass harder. Then I felt the head pop right in. I let out a loud moan and he just told me to relax as he held still. He held his cock there for about 15 to 20 seconds. I said I was ok and he started to push his cock in slowly. He would push in a bit and then slide it out to where just the head was in. He did this quite a few times until I could feel his pelvis against my ass. I couldn't believe he had his entire cock buried deep inside me. He slowly started fucking in and out of my ass. I couldn't believe how great it felt to have his cock pumping in and out of me. He fucked me like this for about 10 minutes and he let his cock slip from my ass. I felt so empty when it came out. We changed positions because his legs were getting tired. He got on the bed and laid on his back and told me to climb on him. I straddled his body and we both took a big hit off the popper. He held his cock up while I slowly lowered my ass down on to it. It felt amazing when it penetrated my ass, it just slipped right in this time. I slid all the way down on his hard cock while I had my hands on his chest and was slowly rocking back and forth. I was enjoying having this hard cock buried inside me so much that I didn't even realize that he had a wall of mirrors beside the bed. When I noticed this I couldn't help but watch as I was having his cock slide in and out of me. He started talking dirty to me as I rode his cock, telling me what a slut I was and how he loved being the one to pop my cherry and fuck my tight virgin ass. As I started fucking faster on his cock he told me he was going to cum soon. I got off his cock leaving me feeling empty again. He rolled me on my back and pushed my legs back against my chest. He pushed his cock in hard this time making me yelp at the pain. He handed me the popper again and we both took nice big hits of it. He started driving his cock in and out of me as deep as he could. I could feel his balls slapping my ass he was fucking me so hard. I kept looking at the mirror next to the bed. My legs up in the air covered in black sheer stockings with a man between my legs fucking me. I couldn't believe it as I watched his ass rise and fall on top of me with each deep thrust. I finally got to wrap my legs around him to hold on. He was driving into me with such force that I could hear his balls slapping my ass. The bed was bouncing and I was moaning in total ecstasy. He told me he was going to cum and all I could say was yes, cum for me, give me that load. He pumped me real hard 3 or 4 more times and pulled his cock out and shot his hot seed all over my chest, stomach, and my cock. As soon as he finished shooting his load on me he rammed his cock back in my ass. It hurt, but it was a good hurt as he buried it all the way in. He continued fucking me until I could feel his cock getting soft inside me. He held it there and started rubbing his cum all over my cock. He stroked me fast and hard until I couldn't take it anymore and shot my load all over myself. He started rubbing our cum all over my stomach and licked his fingers and then he offered his fingers to me. I greedily sucked his fingers into my mouth and licked them clean. He scooped all he could up and brought his hand to my face and wiped it all over my mouth and chin. I was starting to lick it off when he leaned down and kissed me deeply. We kissed for what seemed like forever rubbing cum all over our faces. We laid together for a while until he went to sleep. I went his bathroom and cleaned myself up and got dressed. I left my number on a pad by his phone and quietly left. I drove all the way home in a sort of daze about what I had just done. I knew one thing though, this would not be my last time getting fucked. Too be continued...