5 comments/ 14501 views/ 11 favorites Made Up By: ChewToySub My first story on Literotica! Hope you like x ***** For the longest time, I've crossdressed alone. I taught myself how to climb into girly clothes, how to roll on tights without tearing them, how to put on my wig without it looking like roadkill. It took time, but I slowly learned how to get myself ready to enter girl mode. But there's a few things I've never been able to do; 1) I've never been able to put on make-up 2) I've never felt fully confident as my alter-ego, Danni 3) I've never been fucked as Danni. Last night I managed to tick off all 3 of these things, all in one go. This is that story. It started when I was contacted by a local dresser on my online casual dating profile. We got to chatting and hit it off instantly; although I basically spent 3 hours gushing over her pictures. She was immaculate! Not too drag, not too underwhelming, she was H.O.T. She was experienced in the art of the transformation, and while she wasn't interested in playing, she saw promise in me. She wanted me to be her pet project. I jumped at the opportunity! I packed a humble bag of embarrassing little pieces of clothing; I'd rather turn up with something than be empty handed and have the night cut short. A short taxi ride later and I found myself ringing a doorbell and standing on a doorstep, my heart pounding in my chest like it was going to burst. I realised I didn't know who would open this door, a man or a goddess... A beautiful trans woman opened the door and hugged me before I had a chance to say "wow"! I just stood there, my arms pinned to my sides and my knees touching, as this warm, beautiful woman engulfed me with love. "I'm so happy to see you!" she declared "You look amazing... Thank you for having me over" I stuttered out nervously "Aw honey, I'm happy to have company. And with someone with such good taste" she smirked. "Come on in, I've gotta see you as you want me to see you." I immediately felt so empowered to be around this woman. She knew exactly how I wanted to be talked to, and he long fluffy hair and flowing dressing gown relaxed me instantly. No pressure, no expectations, just a relaxing night ahead. "I'll be honest Miss, I kinda expected you to be fully dressed to the nines! Not that I wanted it! I just... all your pictures" "Aw honey, those are for nights out, or when I'm feeling slutty. We're having a nice night in were we get to have fun and you get to be yourself for once. I know how you feel, I was like you too." I found that hard to believe, but the concept of looking as great is Miss got me instantly elated. ... So to set-up, I had quickly shaved and removed as much hair from my body as I knew how. And for the past 6 months I've been working out (paying particular attention to my hips and butt with some deep squats for that bubble butt look I'm so fond of!), so body-wise I felt reasonably good. I carried in my bag a pair of thigh-high socks, high heels, my trusty long, red wig, and that was pretty much it. "Mmm, that's fine, hun, we'll sort out your clothes later. BCHNF! Body, clothes, hair, nails, face. that's the agenda. Let's get to work." Miss declared. Then nothing. She just stood there. We both stood here. In the middle of the living room. She was staring at me. Nothing. "Uhhh...?" I asked. "Well... Strip off! I'm gonna give you a look all over to figure out exactly what I'm gonna do with you! Danni is a blank canvas right now!" I took a deep mental breath, and tried to match her perkiness. I want to be so much like her. I drop my bag to the side, and strip off all my boy clothes. I am standing in the middle of her living room completely nude, cupping my genitals with both hands, and red-faced I wait. She circled me for what felt like an age or three. She prodded my back to have me straighten my posture, and lifted my arms to see all over. "Okay you've covered most of the hair, and your butt looks GREAT!" (I smiled so hard, Miss could tell it is my pride and joy), "but I'm gonna clean you up fully to get you super smooth. Now sit down for me please." I sat on her couch, and was shocked when she lightly wrapped her fingers around my ankles and lifted my legs up above my head! "Yeah I'll show you how to get all this smooth, if you want a man to spread this you're gonna want this to be trap-immaculate." My entire body turned red, and my cock twitched to life. "Hehe, that is the correct response!" ... With a bath and some magic lotions that removes hair from everywhere, the voice behind the door guided me to perfection. Then a full-body moisturiser had me feeling like human sex-toy. I was sat down in front of a huge mirror at a desk covered in all kinds of colours and fluffy things and lipsticks. Miss loved the colour of my wig so much she decided to work her magic on that rather than give me something of hers. It's my "signature". Beautiful wavy locks dangled down my neck as she finished brushing it while talking me through everything. I was so relaxed and pampered, it felt euphoric. "Okay now spin around honey, I'll do your face for you." Lipstick, eye liner, blush, all things I never even ATTEMPTED myself as I knew how much of a disaster it'd be. When Miss was done, I looked like a different person. I looked PASSABLE! I looked really fucking sexy, if I do say so myself. "My oh my you look beautiful! God, you look very fucking yummy, Danni. How does that feel?" Miss asked, as she turned me towards the mirror "I... I can't... it's... incredible! Thank you so much!" I hugged Miss so hard and tight, as hard and tight as she had hugged me at the door. She looked legitimately happy, too. "Okay, now, last thing's last, we'll get you dressed up and I'll do your nails while you watch TV. You wanna watch my porn videos? Hehe" she joked. "Well..." I implied "Haha! You dirty girl! Okay then!" ... We stood in front of Miss' open closet, my mouth nearly agape at the variety. It went from black elegant to pink cumwhore. I've never felt jealousy on this scale before. "So what do you want to wear?" "I've only been able to wear what was lying around. I've never worn "girly" clothes, or felt sexy." "Oh. I think I know where this is going." Miss reached into the Cumwhore Section and pulled out a latex corset so small it was basically a strip of rubber. "Whoa." "Yeah you don't want to wear this." "What? It looks super slutty!" "Honey, your ass turned red when I lifted your ankles, you don't want slutty you want to feel SEXY! And to feel sexy you need to feel believable and comfortable. That's the most important thing right now. When you feel like a natural girl, then we'll get you fucked and you can start worrying about catching jizz in your waiting mouth." she laughed. "So I'll ask yo again, what does Danni wanna wear?" We ended on some casual, tight streetwear. A sweet Beatles shirt, small hoodie, colourful form-hugging leggings under a little black skirt with pockets and old black Converse sneakers. Miss took a picture of my outfit, hair and make-up for future reference, and to remind me how I should carry myself. Remember point #2? I felt so comfortable and looked so much like a girl I could feel my confidence going through the roof. Miss was completely right! She seemed to beam with pride when I told her. ... So there we were, sitting on her couch watching videos of trans women sucking fat cocks and being fucked wide open. Chatting so casually about sexual experiences and fantasies and opinions, I felt like one of the girls. I wanted to go on a night out with Miss and her friends from the pictures. I wanted to flirt with older men at bars and high-five my new girlfriends on the way out the door. Miss reveled in this. She finished painting my last pinky finger a shiney black. "Honey, you're welcome any time. we'll have to protect you, you look so cute the men will be tripping over themselves to get to you! I'll feel jealous of them, too. I'm very bi, and I would top you in a heartbeat." And that was when I heard the sultriest, sexiest laugh in my life. I froze, but tried to hide it. My heartbeat increased. I wondered if Miss knew this, as she felt my hand and casually ran a hand onto my wrist. Then, in what felt like a choreographed moment of perfection, the TV faded into a clip of a young trap girl sucking the cock of a dominant, latex-covered shemale. "You like that?" Miss asked, with a voice hushed down a notch from her usual, perky tone. I nodded. "I know you said you didn't have much experience with sex as a girl. You feel like practicing?" I bit my lip and looked into Miss' eyes. I nodded, my hair slightly hanging over my nervous face. Miss reached up and brushed a lock out of my face, then ran her hand up to the back of my head. She pulled it down, and I followed obediently. As she did this, her other hand expertly pulled her gown to the side, revealing her beautiful bulge in a pair of smooth silver panties. I leaned right down onto her panties and took over. I began kissing over her panty-covered cock, taking secret sniffs of her while down there. She brushed my cheek with one hand, mostly to give her space to free her chubby, impressive cock out into the open. I kissed it on the tip, pulling the foreskin down a touch, and continued kissing the precum out from her. I sucked her for 20 minutes, and was surprised she gave me no notes, no advice, she just let me do my thing while she sat back and moaned in pleasure. I took this as a great sign. "Hun, you wanna feel like a real girl?" Her cock completely in my mouth, I managed a slight nod and a muffled "Mm-hmm!" I was subsequently bent over the couch, and Miss pulled my new leggings down to my knees. My skirt was thrown up onto my midriff. My perfectly smooth butt hung out in the air, and my new shemale mistress rubbed it all over. A sharp spank or two liberated me. Those spanks felt like girly initiation, so I thanked her for them with pleasure moans. I felt the cool lube drip down onto my ass, and my new pussy felt the intense, nerve-tingling sensation of a warm, wet cock rubbing up and down. Then I felt the pressure of Miss' tool pushing against my puckered hole, tip first. It suddenly felt much bigger in this context. I was fucked like a beautiful, sexy little girl. I felt like a slut, a whore, a bitch, a doll. I loved every fucking second of it. I wanted more! I screamed Miss' house down and covered her couch in cum (No hands! first time!). "Danni, time for your reward honey!" Miss exclaimed. She pulled out of my pussy, and yanked me down onto my knees. I already had my mouth open and my tongue out. She grabbed me by the back of the head and forced her soaking, filthy dick into my mouth and continued fucking like she forgot we changed positions. I felt thick ropes of warm cum shoot wads onto my tongue and down my throat, and when Miss slowed her humping, I pumped my head on her cock to keep it going ( I saw that a few minutes ago in one of her videos!) ... "Thank you so much" I wheezed. We lay on her couch, I rested my head on Miss' heaving chest. "You are definitely coming out with me on Saturday. I'll give you tits, we'll get you a Daddy. You're basically my daughter now." We giggled together. Made-up Detentions *This was written when I was 16 (I am now 25). I just found it while going through my files and figured I'd post it.* Mr. Jason Walker was the senior Science teacher at the local high school. He was quite young for his age, only twenty-five. He had had his eye on one particular girl in his last period class, Manda. She was 5'9, which for his 6'3 was perfect. A tall leggy blond. She didn't do very well in his class. She hardly ever did her homework and had gotten in trouble so many times and had never made up any of the countless detentions she owed to him. One day he got an idea. He had wanted fuck her for so long, since the first day she walked into his class in the nearly too short skirt and barely there top. Her 36 C breasts were always barely covered, just enough though. He enjoyed looking at them. It was a late April day, the end of the week. As the bell rang he called out,"Manda, I need to see you a minute." She gathered up her things and walked up to his desk. He always had on a suit, but by the time her class with him rolled around, the jacket had come off and the tie loosened. He had neatly cut blond hair and a very muscular frame. She had spent many a night masturbating while thinking of him. "Yes, Mr. Walker?" She stopped in front of his desk. He looked up from some papers he was looking through. "Manda, I see you haven't made up any of the detentions you owe to me." "Uh, well no. I guess not. I just get so busy. I never have the time to sit in here after school." "Well, if you don't make them up by the end of the year, your diploma will be withheld until you do." Her eyes went wide,"But..that's..not fair." "If you wouldn't have gotten in trouble in the first place, you wouldn't have to worry about it." "Well, isn't there anything I can do?" Mr. Walker grinned,"As a matter of fact there is," he said standing up, his eyes directed at her breasts. His hand slipped onto her thigh as she leaned against his desk,"I'm sure we could do something about it, don't you think so?" Manda looked down at his hand, where it was resting on her upper thigh, right below the hem of her skirt, and smiled,"Yes, I'm sure there is." "Good. Now that we understand each other..." he leaned forward and started kissing her hungrily. He slipped his tongue in her mouth and explored. Their kisses got harder and more hungry. His hand came up to cup her right breast through her shirt. His thumb teased her nipple through the thin fabric. She moaned into his mouth. Her nipples were throbbing to be released to his hands. He broke the kiss to pull her shirt off, and saw she was wearing no bra. He cleared his desk in one motion and leaned her back across it. His slid down and sucked her left nipple, licking, teasing. She moaned in pleasure. He slid down across her smooth stomach and easily pulled her skirt and thong off in one motion. His licked along her one pussy lip and then the other. She was wiggling beneath his tongue, she wanted more. He nipped at her clit, he could feel her getting wet. He licked her hole really quick, which brought forth a flood of her juices. He licked them up hungrily. Then his wonderful mouth left her pussy. She heard the jingle of his belt buckle and when he joined her again, he was as naked as she was. He teased her by just putting the head in at first. To his surprise she grabbed his butt and pushed him fully into her. She moaned again as he filled her with his beautiful nine inch cock. he groaned and he pulled back out and thrust back in. "Faster," she almost screamed as she could feel her orgasm building. All of a sudden he pulled out and turned her over so her ass was sticking in the air. He shoved his cock into her tight ass and fucked her so hard she screamed in pleasure and pain. His fingers found their way to her clit and rubbed up and down, squeezing gently, until her stomach muscles contracted and she went limp. Right then he pulled out as his cum poured down over her ass and onto her pussy. When they both had their energy back she kneeled and licked all the cum off his cock. "Now, I believe we can make that two detentions made up, Manda. I'll see you tomorrow same time?" "You can count on it," she smiled and headed towards the classroom door. Made You Look We are both competitive. I hate to lose and so does he. Our first date in college was a race around the track. He won. I didn't speak to him for a month. Because I hate to lose. Yet, somehow after that first date I let him take me out again and we never stopped going out. Maybe it's because he completes me, like in some sappy romantic novel kind of way, or because I just like the high I get from beating him at something. I'd like to think it was the romantic stuff but I wouldn't bet on it. So somehow our sex life devolved into a somewhat healthy competition. First off, our 'normal' sex life is actually quite sweet and romantic - the soft kissing, warm embracing, back rubbing, blah blah blah that leads to the dick grabbing and pussy licking that migrates to two (or more) happy orgasms. The competition aspect is a different animal altogether. He blames me for starting it on a warm spring morning. He's a morning person and I'm a night owl. Whenever we are amorous before noon it's a treat - I'm a lady, so I get to decide when & where. But every now & again I get the urge to give a little thrill at sunrise. One morning I woke up from a deep sleep and could feel that he was still naked from the waist down under the covers. The night before was all about my crotch in his face, so I figured I'd simply reciprocate his thoughtfulness. Half-conscious I slid below the covers and placed his limp dick sweetly between my lips. By the third suck his dick was clearly paying attention to my advances, but the rest of his body wasn't cooperating with our positioning. Without breaking stride, I continued to stroke and suck while I lifted the sheets slightly (too much sunshine and my mood would have been thrown) to find his phone was in has hand and his earpiece was in. I'd forgotten about his conference call with Switzerland. But he didn't stop me, so I was determined to drain his seed. It was taking longer than usual without his full attention, but I kept at it until, finally, my face was drenched with my well-earned prize. However, the victory didn't appear to be mine. While I lay soaked in his cum, he discussed engineering plans and government calendars for another 20 minutes. It was as if he could handle my best effort and still get his work done. He was the winner. Not me. The next battle was about a week later. My sister called after he'd gone to sleep and my talking kept him stirring. I offered to take the call into the living room, but he gestured that it was fine and put his head under a pillow. But after 10 minutes of rustling, he decided the best way to finish my conversation with my sister was to start a conversation in my panties. Knowing we could easily talk for another hour, he took his sweet time - caressing my back and kissing my neck, before working his way down my stomach onto my thighs. But I never slipped in my conversation with my sister - even when she was complaining about her afternoon commute and he was tongue twisting my nipples. There were several moments that had me on the edge of telling my sister that the house was on fire and I'd need to call her back tomorrow, but I held strong knowing that the real test was not too far away. Whenever one of us was taking too long during an oral activity, we'd discovered that a lot lube and a little pinky would expedite the interview. It seemed kinky at first, but once we tried it a couple of times it became pretty routine. So somewhere between my nephew's new tattoo and my brother's old tuxedo came the tip of a juicy pinky in my asshole. "Let-me-call-you-back-the-oven-is-on-love-you-bye," I exhaled in one breath and hung up the phone just before squeezing out the type of orgasm that comes after you've tried to hold one back for too long. My sister may have been confused about my cooking at 11:30 at night, but my husband was pretty certain he was victorious that evening - even if my thighs nearly squeezed his head off. But those battles were too much to continue because whenever one of us were on the phone, the other would be there trying to 'score' a victory. I think he blew two deals - or I 'blew' two deals (sorry, too easy) - over the next month. The game, however, didn't disappear. It just evolved into a more creative endeavor. It was a Thursday and he was in the middle of a call after dinner. Leaning against the island in our kitchen, he was also trying to watch sports highlights on the television in the living room. I walked up behind him and undid his belt, dropping his pants below his waist. From behind I began to caress his dick through his briefs, when he held the screen of his phone above his shoulder so I could see the call was from Sean, his newest client in New Zealand. I took this as a hint that we couldn't 'blow' another deal, so I slowly released my gentle grip and left him standing in the kitchen with his dick out. Frustrated with the game being over, I decided to simply change the rules. I walked to the other side of the island and drop my jeans, keeping my eyes locked on his eyes - which are still checking out the scores on the television. Then I pull down my thong, place it on the island, neatly fold it and push it to the center between us. For a split second he gave them a glance, then me, then back to the television as he rattled off some potential sales numbers. We were both still fully dressed from the waist up, so all he could see was my sweater covering my blouse. But when I closed my eyes and started touching myself, I heard him stumble over those potential sales numbers. I knew he was no longer interested in the television. It was now a battle between Sean's sales and my pussy. As I began to search for my own orgasm, I lost track of how many times I heard his throat clear. I was clearly taking the lead. And just as I was about to come he said "Talk to you tomorrow." Within 2 seconds his dick was inside me and we declared the event a tie. Now, when I'm doing my hair in the bathroom before heading to the office, he'll ask me a question from the shower. As soon as I begin to answer I can sense he's got his hands on his dick, stroking it to the sound of my voice. I have to keep talking as though nothing out-of-the-ordinary is happening. Or he wins. That's our game now. Admittedly, we don't mind losing the occasional battle, like when I pull back the shower curtain enough to watch him stroke his dick until his cum sprays ropes against the slate tile. Or when he kisses my earlobe just as I'm about to tremble on the coffee table. I'm okay not winning every battle now. Just as long as he knows that I'm ahead 82-69. That takes focus. I'm definitely winning.