6 comments/ 81834 views/ 29 favorites Tony to Tanya By: joshy029 My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. My ass isn't half-bad either. I'm an open-minded person when it comes to sex. I'm also adventurous. I'll try almost anything at least once, and if I like it, I'll do it again. I'm currently dating a girl called Sarah who's really into being the dominant one in the bedroom. And like I said, I'll try anything, so I'm all for it. She'd only had me do "normal" things like licking her pussy and role-play, which I'd do anyway. My sex-life was about to change dramatically. I was just leaving college one day, when my phone rang. "Hello?" I said as I answered it. "Hey, Tony." Sarah said with a cute voice. "Sarah, how are you?" I asked. "Fine." She answered. "I was wondering if you'd come over to mine tonight. I've got nothing to do, and my parents are out, so I thought we could have some kinky fun. Are you free?" "Sure. I've got a few things to do, first, but I'll be over later." I told her. "Great. What have you got to do, anyway?" she enquired. "Oh, I gotta send an email to Paul." I answered. Paul was in the army and was currently stationed in Afghanistan. "Then I'll eat, shower and come over." I finished. "Alright. Give Paul my best." She said. "I will. Love you." "Love you, too." She hung up. Half an hour later, I walked through the front door. I had a little chat with my parents about my plans for the evening, and went to my room to send my email. When I'd finished, I went back downstairs and made a bacon sandwich. I ate it while watching a comedy quiz show and went for a shower. In the shower, I could hear my sister, who was 20 and home for the summer, listening to some of my music, and I sang along to it quietly. When I got out of the shower I dressed in my Guns 'N' Roses T-shirt and jeans and headed back downstairs to finish watching my show. When it had finished and I'd finally managed to stop myself laughing, I put my shoes on and left the house to catch the bus to Sarah's. I spent the bus ride wondering what kinky things Sarah would do with me. When I arrived at Sarah's, I knocked on the door and she answered it quickly. I'm always stunned by her beauty, but today she was dressed very sexily. Sarah is 5 foot 5 inches tall, with long, curly, blond hair, and an amazing body, including 34C boobs and a lovely heart-shaped ass. But instead of her normal sleeveless top and jeans, she was wearing a top that revealed her flat and toned stomach, and showed that she had no bra on. She was also wearing the shortest mini-skirt I'd ever seen. "Hey sexy, come on in" she said with a radiant smile. I walked through the door and closed it behind me and my surprise must have shown on my face because her smile became even more radiant. "Cat got your tongue?" she asked. "You are the sexiest girl I've ever seen." Was all I could say. I pulled her towards me and kissed her passionately. After a minute she broke the kiss and took my hand. "Come on, lets go to my room. I have a present for you up there. Besides me, that is." I let her lead me to her bedroom and I sat in the chair at her desk while she closed the door. She came over and straddled my lap, kissing me fiercely. She broke the kiss and climbed off me and went to the drawers she kept her clothes in. "Close your eyes." She ordered. I did as I was told and I heard her rummaging in one of the drawers for something. "OK, you can open them." I opened my eyes and saw that she was holding her school uniform from the year before: white blouse, green skirt that would reach about halfway down her thighs. She even had the knee-length socks and the shoes. "I thought you were already dressed up for me." I said, slightly confused. "I am. These are for you." She clarified. It dawned on me what she wanted me to do. I have no real negative views of dressing up as a girl, I just never thought I'd do it before. And I never knew that Sarah would want me to do it. I was shocked to have it being sprung on me so suddenly. "You want me to-" I started. "Dress in my old school uniform? Yes" she finished for me. "You don't mind do you? You said you'd try almost anything and this isn't one of those 'extreme' things that you ruled out of trying." "True." I thought it over. "Since it's just between you and me, I'll do it but it's not something I'd ever thought of before." "It'll be easy. This'll fit since we're the same size." She told me. She wasn't wrong. I don't have the same figure as her, but I'm not muscular or anything. My body's toned and slim. Her old uniform would fit. "I don't quite see where this is going." I said. "You will." She assured me. "Let's do your make-up and then you can change in the bathroom while I prepare everything else. Wear this, as well." She finished, throwing me a black lace thong. She did my make-up: a bit of eye-shadow, a small amount of blush and some pink lipstick. She brushed my hair as well, making me look like a very pretty girl when it was all done. I set off to the bathroom to change. I stripped to my boxers, put the blouse on and buttoned it up. I couldn't believe I was going through with this. I then took my boxers off and pulled the thong on, I had to rearrange myself so I was comfy. I pulled the skirt and socks on with no difficulty and my nervousness was starting to disappear. When I had the shoes on I stood up and looked in the full-length mirror. I was astounded. I looked immensely cute and shy, like the new girl in school. It was as if I wasn't looking at myself. My cock started to push against the material of the thong. I was really starting to get into this idea, but I still didn't have the full picture of what we were going to do. I went back to Sarah's room. "You look cute, sweety." Sarah said as I walked in. "You need a girl's name to finish with and I thought of one: Tanya." "Tanya." I repeated. "Sure." "I need to ask you something. Do you have anything against receiving anal?" Sarah asked. "No." I said. "I've experimented." My sister went to a college in another town, so she was only ever home for the holidays. She had a lot of toys of different shapes and sizes. When she was either at college or out, I experimented with them: dildos, anal beads, vibrators and butt plugs. I even went to school with a butt plug in, once. I enjoyed anal more than I thought I would when I first tried it. "Good," She said, "Because today, I'm going to fuck your ass. Do you need lube or anything?" she gave me a smile. She was clearly being careful with this experience. "I don't need any lube." I said, returning her smile. "I can tell you're excited, so lets start with the foreplay, shall we, babe?" she asked. I nodded and she motioned for me to lie on the bed. I did as she wanted and she straddled me, rubbing the crack of her ass against my cock as she kissed me. I opened my lips when her tongue brushed against them and our tongues started exploring each others' mouths. After a couple of minutes, Sarah broke the kiss and stopped grinding on my cock. She moved up to my head and took her panties off, she then straddled my face while facing my feet. She spread her ass cheeks and lowered herself. "Lick my asshole." She ordered. Something else I'd never done until then. I extended my tongue to that tight, rose-pink bud and licked around it. She moaned with pleasure and ground herself into my face. I licked around once again and then pushed my tongue into the tight hole. Doing this made her scream with pleasure and lust. "Get on all-fours." Sarah told me, climbing off of my face. I did as I was told. She got on her knees behind me and spread my cheeks, moving the thong to one side, which made me tense with excitement and nervousness. She spat on my asshole and started to lick, working her saliva into it. The sensation was amazing. It was one of the most erotic experiences I had ever experienced. I groaned in pleasure and happiness as she slowly pushed her tongue into me. I was starting to hope the sensation would never end. She stopped licking and spat on my asshole again. She sat up and rubbed her saliva in, before slowly pushing two fingers into my ass as deep as they could go. As I was reaching new heights of pleasure, she doubled them by slowly pumping her fingers in and out of me. After a while of doing this, she added a third finger and carried on fingering my ass. My cock was straining against the thong she'd given me. "Turn around and close your eyes, but stay on all-fours." She told me, removing her fingers. I positioned myself as I was told, while she reached under her bed. I closed my eyes while she was searching. I heard her fiddling with something and I began getting a little more excited. "You can open your eyes now." She told me. I did so. There she stood, wearing a strap-on dildo. It was purple and fairly big at 10 inches long. It also looked very thick. She stood in front of me, looking at me with lust. "Suck my 'cock', you little slut." She commanded of me. I was happy to oblige. I leaned forward, grabbing the shaft of that huge fuck-stick and licked the end, before I slid it in my mouth. I bobbed my head, while swirling my tongue, sucking the strap-on how I liked my cock sucked. "That's right you little bitch. Suck my big cock like you mean it." She encouraged. "Suck it as deeply as you can." I slid it as far into my mouth as I could manage without choking which was about 7 inches. I was really into this, now. Sarah started thrusting in my mouth, getting just a bit of the dildo down my throat. She pushed my head away and turned me around. "I'm going to tie you to the bed, now, slave." She said forcefully, tying one arm to one of the bedposts at the head of the bed. She than tied the other arm to the other bedpost, giving me just enough slack to lay my head on the pillow comfortably. Once again, she moved my thong (as I began to think of it) aside and spat on my asshole. This time she rubbed it in with the strap-on, mixing her saliva and mine. She grabbed my hips and positioned the head of the dildo at the entrance to my ass. After a bit of prodding me, she pushed the large, thick 'cock' into me. I winced from the small amount of pain and the sudden intrusion, but within a few seconds, both sensations had dissipated. Sarah was letting me have a bit of time to get used to having something so large in my ass. Slowly and gradually, she began pulling out of me. When she'd pulled out to the tip of the dildo, she reversed direction, pushing it back in a little more gently than when she first entered my ass. After the first thrust, she set a slow steady pace of thrusting. It felt amazing. I could feel my ass squeezing the dildo gently, as if it was trying to keep it inside me. My cock was straining more than ever against the thong I was wearing, as if it was trying to get loose by breaking it. Sarah started thrusting faster as she reached around towards my stomach to slowly pump my cock with her hand, after moving the front of the thong aside. She rubbed her finger into some of my pre-cum and put it to my lips for me to taste. I stuck my tongue out and licked her finger. It was quite a nice taste: slightly salty and a little sweet. I was really getting into having my ass pounded like a little slut. When Sarah picked up the pace again, I began to meet her strokes, making the dildo go into me as deep as I could accommodate. I started feeling my balls tighten, ready to release a massive load all over Sarah's bed. I didn't want to cum so quickly, I was having too much fun, so I fought with the feeling. I couldn't fight it off longer than a couple of minutes. As I was just reaching my boiling point, I let out a groan. "Sarah, I'm cumming!" I yelled. "Yes! Cum for me. Cum from having your ass fucked." She said in response. Long, thick strings of cum flew from my cock, covering her bed and hand. She once again put her hand to my lips and I lapped my cum up without letting a single drop fall from her fingers. It had a stronger taste than my pre-cum, and it was thick and rather difficult to swallow, but it tasted great. I was surprised I was doing it, but had no misgivings about it. Sarah kept pounding my ass until the friction of the strap-on against her clit caused her to cum with a squeal of bliss. She collapsed onto my back and I fell onto my front in the pool of cum on her bed sheets. The dildo was still in my ass and I was content to leave it there for a while longer. "Did you enjoy that, babe?" Sarah asked me. "I loved it." I told her. "Did you enjoy dressing up and do you think you'll do it again?" "Yes and yes." I answered. "I think we may need to go shopping, then." She said and kissed my ear-lobe. Tony to Tanya Ch. 02 Author's Note: Thanks to everyone who read, voted and commented on the first installment of the "Tony to Tanya" series. I'm really appreciative of you all. It is, after all, always good to get such positive comments as a new writer. I'd also like to say that i have another installment after this one. It's only the most basic of ideas right now, but it will come to me. I'll start on it, or at least outline it, when it comes to me. i do, after all, have other projects to do on other sites that i've been meaning to do for a while now. Thanks again to everyone that have read and enjoyed this series so far. Enjoy. *** Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays. The reason he was excited suddenly hit him. On Tuesday, Sarah had told him they were going shopping today. This had been right after a great fucking-session in which Tony had been dressed in Sarah's old school uniform and she'd fucked him with a strap-on dildo. It had been a very kinky evening. Very carefully and gently, Tony extracted his arm from underneath his girlfriend and made his way to the door. He went down the hall for a shower, wondering what shops they'd be visiting and what they'd be buying for him. He knew it'd be girl's clothes, but he had no idea what-so-ever what kind. While he was pelted with water from the shower, images came to his mind. Thongs, skirts, stockings, dresses, blouses, and every other kind of girly clothing-article he knew of. In his mind's eye, he was wearing them and examining himself in a mirror. Tony's hand drifted towards his crotch as he thought of these things, and he began to stroke it absently. Thankfully, Tony wouldn't have to be sized-up for these clothes. He wasn't much taller than Sarah, and the extra height was just leg. He'd be dressed up when they went out, and he'd be using his best girly voice, which he'd been practicing in his spare time. When he was trying anything on, Sarah would go into the changing room with him, under the pretext of helping one of her girlfriends find clothes that suited "her". Nobody would know it was actually her boyfriend. Tony just hoped he wouldn't see any of is friends in the town centre; that would be uncomfortable. The sound of the bathroom door opening snapped him out of his thoughts, and he realised that he was actually stroking his cock. He quickly stopped. "I'm in here," he called, thinking it must be one of his parents or his older sister. "I must have forgotten to lock the door." "Don't worry," Sarah's responded. "It's just me. Nobody else is home." "Right," Tony said, feeling like an idiot. His parents would be at work and his sister would be out with the friends she hadn't seen since her last holiday from college. "I forgot that nobody would be in at this time." Sarah walked into the bathroom and looked around the shower curtain. Her eyes wandered Tony's body and she noticed his erection. "Excited about today, eh?" she asked with a sly grin. Tony blushed slightly. He was comfortable with being naked in front of Sarah, and he was comfortable with what had transpired on Tuesday. But for some reason, admitting being excited about the day's planned shopping was slightly embarrassing. Instead of saying anything he just nodded. "Well, we can't have you walking around with a raging hard-on, now can we?" Sarah asked, sounding amused. "Unless you want people to know you're cross-dressing?" Tony shook his head vehemently. He didn't want people to know that. He wanted his life to be without people automatically thinking he was gay, which he was certain most of his friends would do if they were to find out. "Then you'd best make sure that goes down before we go out." She told him. "Wash yourself with this hair-and-body wash and use some conditioner, your hair's long enough for you to not need a wig." She added. She left to have breakfast, leaving Tony to wash himself as she told him to. He had to be able to pass as a girl in scent as well as looks, after all. When he'd finished showering, Tony went downstairs wrapped in a towel and made himself a bowl of cereal. He went to eat it in front of the TV where Sarah was eating her own breakfast and watching a sitcom. While he was eating, Tony kept giving Sarah side-long glances. She didn't seem to notice, or if she did, she didn't show it. He was starting to get nervous about today's plans. He'd be out, dressed as a girl, and with England's weather, the skirt he'd be wearing would probably be caught in anything from a strong breeze to a strong wind. That would probably expose him to everybody in the vicinity. Tony still couldn't quite believe what he'd gotten himself into. He'd always known his girlfriend was kinky, but he'd never in a million years imagined she'd get him to dress as a girl, fuck his ass, then take him shopping for some girly clothes of his own at the weekend. He enjoyed it, but he was still apprehensive about the entire thing. "We'd better get ready." Sarah told him, breaking his chain of thought. "Sure," he said. "You are going to help me, right?" "Of course I am." She told him. "You'll have to practice the hair and make-up part yourself, but I'm sure you can dress yourself." She added teasingly. Tony took their plates into the kitchen then they both climbed the stairs and went back onto his room. Sarah went through a drawer where she left some of her clothes for whenever she slept over. It saved her having to bring a change of clothes with her. 'Two changes in this case.' Tony thought to himself. She brought out two pairs of panties; a thong and a full-seat pair, two skirts and a couple of plain tops for them both to wear. She handed him the panties, keeping the thong for herself, and then a skirt and top before going back into the drawer to get herself a bra. They got dressed quickly and Tony waited while Sarah did her make-up. When she'd finished, she motioned him to sit in the chair she'd just vacated and she did his. Nothing extravagant, but enough to ensure nobody recognised him as a boy. Then she did their hair; straightening it and ensuring that it made them both look sexy, and in Tony's case, like a girl. Sarah handed Tony a pair of stockings and pulled a pair on, herself. When he had them on, she picked a pair of shoes for him and then they went downstairs. She put on the shoes she'd brought with her the night before and grabbed her handbag. They were ready to go out and Tony was extremely nervous to say the least. An hour later, "Tanya" and Sarah were walking down the high street in the city centre. Sarah had noticed that Tanya looked worried and only one thought passed through her mind when she had first noticed it: cute. Many people turned their heads to get a second look at the two of them. This was what Tanya was worried about; that somebody might notice she wasn't actually a girl. Luckily, she hadn't seen any friends from college. If she had, she'd have probably passed out from fear of discovery. They reached a clothes shop exclusively for girls and went inside. It was beautifully set-out. Unlike the unisex or men's shops in the city centre, everything was in a specific location. Underwear was hung along one wall on hooks and on a few small stands just in front of the wall. There was a wall exclusively for shoes and then there were skirts, dresses, blouses, stockings and tights, trousers and even hats in their own little, neat sections. "Welcome, ladies!" the woman behind the counter said, enthusiastically. "How may we help you today?" "Oh, we're just looking for some clothes for my friend, here." Sarah said, without even a hint in her voice to insinuate that Tanya was actually Tony. "Alright, what sort of thing are you looking for?" the shop assistant asked. "Some sexy clothes." Sarah told her. "Something that suits Tanya, here." "I think we have something she'd look very sexy in." the shop assistant said, winking at Tanya. She motioned them forward and they walked towards the changing rooms. They stopped half-way down the shop and the woman grabbed a few items. They went further and she grabbed a few pairs of stockings. "I'm grabbing you things that go well, together. I hope you don't mind me picking a few items to try." She said. "Not at all. Any help you can give me is welcome." Tanya replied. "My name's Sophie." The assistant said. "Nice to meet you, Sophie." Tanya said. As they'd been walking, Sophie had grabbed more things for Tanya to try. They reached the back of the shop and stopped. "You can wait here, if you like, Sarah. You don't need to keep an eye on me. I remember our deal." Sophie said with a wink at Sarah. She pushed Tanya into one of the booths and pushed her down. "You're very sexy, Tanya." She said. "Or should I call you Tony?" "You know?" Tony said, reverting back to his own, male voice. "How?" Sophie chuckled. "Sarah and I are friends. She comes in here to shop every so often and we built up a friendship. She came in on Wednesday and told me of your hot fuck-session. I wish I was there to watch, and maybe join in." A large grin was on Sophie's face by this point and Tony was seething silent anger towards his girlfriend. She'd told him this was to be a secret and then she'd gone and told this woman all about it. "Before you two were dating, Sarah and I were actually fuck-buddies." Sophie continued with her monologue, ignoring Tony's obvious anger. "She's told me quite a bit about you when we've had lunch together and we both think you'll like me." At that point, Sarah popped her head around the door and Tony's head snapped around so he could glare daggers at her. "Sorry, Tony. I had to tell her. She's not you're average girl." She said apologetically. "Anyway, she falls under the category of one of your fantasies." Tony was baffled, he had plenty of fantasies. Every guy did. He was running through them all when Sarah spoke again. "About the agreement, Sophie." She said, and Sophie's head snapped around. Sarah smiled. "Anything goes. I was a bit reluctant, but go for your life." "Thank you, Sweetie." Sophie said and Sarah left, closing the door behind her. Sophie quickly locked it. Tony was still going through all his fantasies. Or rather the fantasies that were relevant to the situation he was in. Lesbian seemed to be the obvious fantasy. But then, there wasn't another girl in the room...unless his alter-ego, Tanya was involved. Tony's mind was racing when Sophie answered which fantasy it was. Sophie unzipped her skirt and pulled hit down, revealing lovely pink lace panties. She had brilliant legs and Tony could also see she had a magnificent, round ass. There was something out of place, however, but before his brain registered it, Sophie was pulling her panties down, as well. When she stood up straight again, Tony could see a rather large cock between her legs. Sophie was a Transsexual. Tony had had fantasies of fucking a shemale for years. He thanked Sarah in his head with extremely humble apologies for being angry at her. He cock was responding to the amazing woman before him. "By the way, I figured I ought to tell you why Sarah has that strap-on." Sophie said. "It was so she could return the favour to me. We usually only ever did anal, and she liked to fuck my ass every once in a while." Tony's cock was fully hard by the time she'd finished and he was dying to get a piece of her. He felt very restricted in the panties Sarah had given him earlier that day. Sophie smiled as if reading his mind before kneeling down and sliding her hands up his thighs slowly and seductively. Her hands reached the waistband of Sarah's panties and her fingers hooked under them. She pulled them down, stopping only so Tony could raise himself of the changing booth's bench so she could take them off. Once Sophie had pulled the Panties over the shoes Tony was wearing, she bunched them up and put them next to him. Tony noticed that the beautiful Transsexual woman was looking at his cock and licking her lips. She stared at Tony's cock while she gently pushed his legs open. When they were open a decent amount, she leaned forward and licked up his shaft, causing Tony to grunt with pleasure. "I want you to use your girly voice, not your every-day voice," she told him with a smile, before diving back to licking his hard shaft. Tony released a small, girly moan of pleasure this time, as Sophie wanted. When she got to the head of his cock, she swirled her tongue around it like a pro. Tony had to stop himself from screaming his assent. Sophie noticed this and picked up the discarded panties. She balled them up and pushed them into Tony's mouth so he wouldn't have to hold his moans back as much. When that was done, Sophie slid his entire cock into her mouth. Tony's pleasure was so much that he almost screamed into the panties in his mouth. He was having his cock sucked by a shemale, he was in heaven. Sophie started sliding her mouth up and down Tony's cock, swirling her tongue around the head when she reached it. He could hardly hold back from cumming, and even with his best efforts, he'd cum soon, anyway. As the thought hit him, he felt the familiar sensation in his balls that told him ejaculation was on its way. He couldn't say anything, because of the panties in his mouth, and he was feeling too good to take them out. Suddenly, Sophie stopped sucking him and looked him in the eye. She gently pulled him down off the bench and onto the floor where she straddled his head and got back to what she'd stopped. It was only then that Tony realised she'd been stroking her own cock. Without hesitation, he removed the panties from his mouth, raised his head and started sucking her cock, like she was his. They were now both sucking each other and moaning into each other's cocks. Suddenly Tony came. Moaning into Sophie's cock as he filled her mouth with his cum. She was milking every last drop from him as she continued to suck. Before he'd finished cumming, her own orgasm started. Warm cum shot into his mouth and he struggled to swallow it before the next spurt came. He swallowed furiously, as he might do with a glass of water in summer after being outside for several hours. Eventually, their orgasms both stopped, and Sophie stood up, shakily. "That was amazing." She said. "We'll have to do more another time." She pulled her panties and skirt back on, and when she was fully dressed she'd regained her composure. She no longer looked as if she was about to collapse. Tony follower her example and took the panties he'd been wearing off the floor and pulled them back on. They were damp with his saliva. "Shall we go and get those clothes paid for, 'Tanya?'" she asked with a grin and a wink. Tony just nodded, and then followed her out of the changing room where they met Sarah. "Have fun?" she asked with a wide smile on her face. "Yes, thanks." Tony said in his best girl-voice. "I finish work at six if our plans or still on tonight, Sarah." Sophie said. "Sure, Sophie." Sarah responded. She then turned to Tony and said, "You don't mind having dinner with me and Sophie do you, Tanya? We'll do something fun afterwards, too." "Of course I don't mind." Tony said, still using his girl-voice. "I'm sure it'll be a lot of fun." Tony had no idea what Sarah had planned, or Sophie, for that matter. He was sure it'd be fun, though, and he already had his suspicions as to what the plans were. To be continued... Tony to Tanya Ch. 03 authour's note: i'm terribly sorry it took so long for me to write this. i know that at least a few of you are pretty peeved at me. to explain, i got writer's block and i just couldn't think of any way to end it. as a result, the ending isn't as good as the rest of it, in my opinion. as i've mentioned before, this is the last chapter planned in this series, though i may come back if i have any ideas in the future. i've currently started work on the start of another series, but i'm not revealing any details yet. i hope you enjoy the story. *** Sarah finished applying make-up to Tony's face. It was mostly subtle, just enough to highlight his eyes and cheeks. The only part that wasn't so subtle was the lipstick; bright red. He was already dressed up in a beautiful black dress that left his back and shoulders exposed and only went down to mid-thigh. It was one of Sarah's, since they didn't want to spend too much money on a dress that was only planned on being used once. He was wearing realistic breast-forms, glued on to fill out the chest of the dress a little. They looked pretty good to him. Underneath, he was wearing a pair of lacy, red, French-knickers to match the red lipstick his girlfriend had just applied to his lips. Tony was worried again, though. Just a few hours ago, he'd been shopping with his girlfriend Sarah. They'd gone to buy some clothes for him. Girl's clothes. He'd gone out dressed up, but that was only for a short amount of time, most of which he spent in a dressing room of a shop. This time they were going out for several hours, all of it in full view of the world. Surely somebody would realise he was a guy, not a girl, even if he had the figure of a young woman. He'd also met an old friend and fuck-buddy of Sarah's. She was called Sophie, a beautiful transsexual woman. Under the guise of giving "Tanya" help getting changed and to give her opinion on the new clothes, Sophie had sucked Tony's cock. Tony had returned the favour, sucking his first cock and carrying out one of his fantasies, being with a transsexual, in the process. Now he was going out to dinner with his girlfriend and Sophie, who he supposed was his new friend. They were going to a nice Italian restaurant on the other side of town. Tony had been there before, for his eighteenth birthday. They did good food and he liked Italian food. There was a knock at the door and Sarah went to answer it. When she came back into the room, she was accompanied by Sophie. "Hello Tanya," Sophie said with a wink. "How you doing?" "Fine thanks." Tony replied in his very best girl-voice. "What about you?" Sophie made a motion indicating that she was fine while Sarah told them both that she was going to get ready. She'd spent all her time helping Tony that she hadn't had time to get changed or put any make-up on. Tony and Sophie both nodded. Tony went and got the shoes he was wearing for the evening. They were black with 3-inch heels and the perfect size for him. "Has Sarah told you the plan for this evening?" Sophie asked him as he put his shoes on. Tony nodded. While he'd been in the shower, Sarah had been on the phone with Sophie, getting the details. After dinner, they were going to a nightclub for a few hours before heading back to Sophie's place for the night. Tony's parents weren't expecting him home and neither were Sarah's. Tony and Sophie exchanged a bit of small-talk on the sofa while waiting for Sarah. They told each other a little about themselves and things they enjoyed doing. The main thing they had in common was Sarah: they both enjoyed doing her. While they were chatting, Tony checked Sophie out. She was wearing a stunning red dress that barely reached below her ass and showed ample cleavage. Her shoes matched her dress, red with 4-inch heels. Her dress was riding up, so that it was practically around her waist. She didn't even attempt to adjust it, she just left it like that. Tony observed that she was wearing a blue thong that only just covered the slight bulge of her soft cock and her balls. Her hair was straightened to frame her pretty face, much like Tony's was, but much more elegant due to the fact that her hair was longer. It fell like a sheet down to her shoulder-blades with slightly curled tips. At first-glance, it didn't look like she was wearing any make-up other than her deep-red lipstick. Upon closer inspection, she had subtly applied blusher, mascara and a very light amount of foundation that was hardly noticeable at all. About ten minutes after she'd left, Sarah came back into the room and put her own shoes on while listening to their conversation. She was also stunningly beautiful in a dark-green dress and matching 4-inch heels. Her outfit was only slightly more conservative than Sophie's, reaching down to mid-thigh and showing less cleavage. The three of them sat talking for half an hour before getting in Sophie's car and heading to the restaurant. They arrived ten minutes before their reservation, but the booth that Sophie had reserved for them was free to they were seated and talking while waiting for the waiter to arrive and take their orders. When they'd ordered their food and drinks, they kept talking and joking to pass the time. Tony made sure to be careful with his voice, since he was out as Tanya, not himself. After eating, Tony excused himself to use the bathroom. Walking into the Ladies' room instead of the men's took a lot of concentration, he didn't usually think about it. He met the girls back at the table before they left and got back into the car. They pulled into a car park near the club and found an empty space. Tony didn't usually go to nightclubs, and even when he did, he wasn't dressed as a girl. Id they asked him for ID he was screwed, his alter-ego didn't have any. Luckily, he didn't need it. Sophie knew one of the doormen and they go in without a fuss. Unlike the rock bars Tony had been to, this bar was a mixer, playing all kinds of music, from jazz to indie, to rap. It turned out to be quite a fun place. They had a few drinks, Sophie going for water or soft drinks since she was driving, and a few dances. After a while, Tony needed to go to the bathroom again. Pushing through the people that were dancing, he didn't notice that somebody was following him. Still oblivious, he walked into the ladies' room and into a cubicle. A minute later, as he was leaving the cubicle, he bumped into Sophie. She pushed him back in and he stumbled back, ending up sat on the lid of the toilet. Sophie walked into the cubicle, closing and locking the door. Tony would have had no escape, even if wanted to escape. "Do you know how hard it is to resist your girlie-voice?" she asked, obviously flustered. "No I don't." Tony said in the very voice she was talking about. He grinned. "How hard is it to resist?" "Lets just say I wanted to throw you on the table at dinner and fuck you." She replied, even more flustered. "I wouldn't have minded." He told her, putting a hint of invitation into his voice. "We're alone here, how about I let you relieve your tension?" That brought a big grin to her face. She pulled the hem of her dress up and exposed her hard, thong-clad cock. Tony knelt on the floor and looked up at her. She looked back, her eyes begging for him to suck her cock. He waited until her eyes told him she was experiencing unbearable sexual agony before licked her cock through her thong. Sophie uttered a moan of relief and pleasure as he continued to lick, causing the material to slowly soak with saliva. As he licked, he moved a hand up and cupped her balls through her underwear, gently squeezing and manipulating them, occasionally going to lick them or suck them. Tony stopped licking and pulled the material of her thong aside, allowing her rock-hard cock the freedom it would be begging for, if it could speak. He began to lick it again, savouring the taste of her bare cock. He allowed his tongue to flick over the head of her dick, tasting her salty pre-cum. He wanted more that that, however. He licked down to her balls, licking and sucking them before licking back up her shaft and engulfing the head. Sophie sighed as he licked a circle around her engorged head, then slid more of her shaft into his mouth. Tony brought his head back, allowing his tongue to slide along the underside of Sophie's cock, causing another sigh of relief. When he had only the head in his mouth, he bit down lightly before sliding back down, taking more of her in, this time. He started bobbing his head back and forth, coating her shaft with his saliva, before releasing the beast from his mouth and standing up. Her disappointment was palpable. He'd stopped before she came and she wasn't happy. He kissed her before she could voice her outrage. Her tongue brushed his lips and he parted them in an invitation, which she instantly accepted. Their tongues danced a waltz, exchanging saliva and her salty pre-cum. Tony slid his hands up Sophie's waist, underneath her dress as she pulled his dress up and grabbed his ass. As she kneaded his ass cheeks, Tony stroked her waist and back, slowly going up until he had his hands on her large breasts. He ran his thumbs over her nipples, before squeezing them between thumb and forefinger. Sophie moaned into his mouth and sucked on his tongue while she slid a hand under the thin piece of material in his ass crack and rubbing his tight, puckered anus. Tony pulled her dress over her head, breaking the kiss for a second to do so, and dropped it on the lid of the toilet behind him before going back to work on her nipples. He alternated between squeezing, twisting and rubbing them. Tony broke the passionate kiss and stopped playing with Sophie's nipples. Once again, he knelt down, this time hooking his thumbs into the waistband of her thong and pulling it down to her ankles. She lifted each foot off the floor in turn so that he could fully remove her underwear and place it on top of her dress. All the while, he was watching what she was doing. He was as hard as she was, and it showed. The tip of his cock was peeking out of his own thongs waistband. He removed it and let his cock spring free, putting his underwear with hers, then he removed his dress and did the same. They were both naked now, apart from their high-heels. When Tony had finished removing his clothes, Sophie spat on her fingers. "Turn around, bend over and spread your cheeks." she told him. He did as he was told, bent over slightly with his hands spreading his cheeks so his anus was clearly visible. Sophie slipped he fingers between is splayed ass cheeks and rubbed her saliva into his anus. When his hole and her fingers were sufficiently wet, she slipped her middle finger in up to the first knuckle. His sphincter clamped down on it tightly and she slowly pushed into him until she had her whole finger in. Tony moaned in pleasure, despite the pain that accompanied it. He'd been dying to have Sophie in his ass, and now she was working to have the same thing. She slowly started to pump her finger in and out of his ass, allowing time for him to relax. When he had and his ass was a little looser, she started pumping faster, making Tony moan a little louder. After a while she slid a second finger in and a few moments later, a third. She continued to pump her fingers into him, hardly breaking the pace she'd set when she slid the next finger in. He moaned louder and louder with each added finger. When Sophie was satisfied that he could handle her cock, she pulled her fingers out of his ass and slid her shaft between his cheeks. As she rubbed her cock between his cheeks, Tony could feel the pulse of the blood flowing through it. The slight vibration of it felt wonderful. She offered the fingers that she'd had in his ass to him and he clamped his mouth around them. He sucked and licked them as if his life depended on it. After a short while, Sophie removed her fingers from Tony's mouth and used a hand to spread his cheeks while she lined her cock up with his anus. When she was ready, she gently pushed forward, easing herself into his tight, warm ass. Within a minute, she was balls-deep inside him and he was moaning in pure pleasure. It occurred to her that somebody could come in at any second and hear them fucking, but she didn't care. In fact, she welcomed them, maybe when they saw that she had a cock they'd want her, too. Slowly, she pulled out until only the head of her cock was inside Tony. She stayed there for a few seconds, then she slammed back in as deep as she could get, making him cry out loudly. She set a slow, steady pace and, after a while, Tony pushed back to meet her strokes, causing them both a lot more pleasure, their moans mixed; the sounds of shared bliss. As she ravaged his ass, Sophie reached around and grabbed Tony's cock and started to stroke it, matching the strokes of her hand with the strokes of her cock. Tony wasn't making any noises of pleasure any more; he was trapped so deeply in the throes of his pleasure at being penetrated, that his voice was failing him. On top of that, his knees were buckling. Soon he'd be on the floor. As if she was reading his mind, Sophie gently lowered him to the ground, not removing her cock from his ass. Once they were both knelt, she resumed her thrusts with vigour, increasing the speed and strength of them. Before long, Tony felt a tightening in his balls. He was about to cum, but he couldn't tell Sophie because he couldn't even articulate screams of pleasure. Suddenly, Sophie plunged balls-deep into him and held herself there. Her cock bucked several times, shooting jet after jet of hot cum into Tony's anal cavity. He could feel it splashing against the walls of his ass and trying to escape. At this point he was unable to stop himself cumming and he shot several jets onto the floor of the cubicle. Sophie held herself in his ass as she slowly softened inside him. He saw her reaching for her tiny handbag. When it was out of his sight, he heard her take something out, but he was too drained to turn to look. Finally, she slid her cock out of him. Before any of her cum could escape, she slid a butt plug into his still-gaping hole. Ten minutes later, they were searching the club for Sarah. When they'd both recovered, they had cleaned the cubicle, gotten dressed and touched up their make-up before leaving the bathroom. They found Sarah waiting impatiently at the bar, where they'd left her. They walked over to her and she hugged and kissed them both before turning to Sophie. "I told you that you could fuck him and come right back, not fall asleep afterwards." she said indignantly. "Sorry. We got a little carried away." Sophie replied. "Shall we get going?" Sarah nodded and the three of them left the club and got back into the car. Tony found this a little uncomfortable, since when he moved, the butt plug moved. It did help him walk a little more femininely, though. He'd practised that, but it was always forced. With the butt plug it was more subconscious so that he was comfortable. "So, did you have fun in the bathroom, you two?" Sarah asked. "Yeah," Sophie said. "It was a lot of fun. You should have heard Tanya scream." They both laugh and Tony felt himself blush a little. The rest of the long trip was almost silent and it was a relief when Sophie pulled her car into her driveway. Tony thought that the house Sophie lived in was that it was too large for one person. And he marvelled at the size when she gave him a tour while Sarah went to grab some drinks for them. It was a four-bedroom house, meaning there was a lot of unused space. The last room to look at was the attic, which was Sophie's bedroom. It was spacious and had two windows; a skylight and one on the side of the house, during the day the room would be very well-lit with natural light. In the middle of the room was the largest bed Tony had ever seen. It would easily be able to hold six people quite comfortably, and it looked extremely soft. The rest of the room was quite messy, papers, books and clothes strewn around, as if somebody had been looking vigorously for something and not tidies up afterwards. The only tidy things in the room were the TV stand, computer desk and bed. "Sorry about the mess," Sophie said. "I don't usually have a reason to clean up. The clothes on the floor are clean, I just don't have the time to put them away. Well, that, and I don't have the room for them anywhere." To show what she meant, she walked over to the wardrobe in the corner and opened it, then opened the drawers next to it so that Tony could look in them. Inside were a lot of clothes and items she obviously used when she masturbated or when she had somebody to fuck. Dildos, butt plugs, strap-ons, vibrators and just about any sex-toy that Tony could imagine was in the drawers. The wardrobe held mini-skirts, tops, catsuits, and sexy outfits of every kind made of just about every material. He found himself a little light-headed and he felt his jaw literally drop. When he heard the door open, Tony turned and watched as Sarah climbed the stairs carrying bottles of beer, vodka and coke in a box. "From the look on your face, I take it she's showed you her collection of toys and clothes?" she asked with a slight smile. Tony could only nod in response. "Aww, looks like she's speechless." Sophie teased, still calling him by his portrayed gender. She closed the wardrobe and drawers and gently pulled a still-speechless Tony over to the bed and pushed him into a sitting position. When he finally snapped out of it, Tony found himself cradling a beer he only just remembered being passed to him. He took a sip and collected himself. He noticed that Sophie also had a beer, while Sarah had a vodka and coke. They talked and joked for an hour while the alcohol lasted then had to decide on what they were going to do next; sleep or something else. It was Sarah who came up with the most fun idea. "Well I say we have a threesome." Sarah suggested. "I agree." Sophie piped in. "Tony?" "Yeah." he said, enthusiastically. Sarah jumped at them both, knocking them flat on their backs, and hugging and kissing them both, laughing. Tony had a feeling Sarah had wanted a threesome with him and Sophie for a while, now. She finally stopped and let them sit up. Sophie stood, walked over to the wardrobe and opened it, once again revealing her kinky clothes collection. She started rummaging inside, and when she turned around again, she had three outfits: a skin-tight latex bodysuit that looked like a one-piece swimsuit with a hole in the crotch that was obviously for her manhood, and two French-maid outfits. She tossed one of the maid outfits to Tony and the other to Sarah. "You'll have to take the breast-forms off for that, Tanya." she said. "It's a bit tight in the chest." Tony nodded and went to the bathroom to change and take the breast-forms off. First, he took his dress and shoes off, then concentrated on the breast-forms. The glue holding them on was water-soluble, so he daubed water around them until they were able to be easily removed. Next he got dressed in the outfit Sophie had given him. It was too tight in the chest for him to have worn with the breast-forms on, as she'd said. The outfit was a standard French-maid outfit: white blouse, black dress, white stockings, a matching garter-belt and a bonnet. He thought he looked quite sexy in it. He picked up the dress, shoes and breast-firms he'd discarded and carried them back into Sophie's attic-bedroom. He discarded them once again, where Sophie indicated and she handed him a pair of shoes to put on. They were simple shoes, black with flat heels. Sarah was wearing the exact same outfit as he was and looked very sexy in it. Sophie, however, was wearing what Tony suddenly thought of as her dominatrix outfit, her cock and balls hanging through the hole in the crotch. Tony to Tanya Ch. 03 It suddenly clicked; 2 maids, one Mistress. It gave him a feeling that Sophie was going to boss both him and Sarah around. A little thrill of excitement welled up inside him, warming him from his toes and slowly moving upwards towards his head. A threesome was new to him, but a threesome with bondage? He'd not been expecting that. He was even more excited now. Sophie moved over to the bed and lay down, beckoning them both over. Tony and Sarah did as Sophie motioned, and lay next to her, on either side when she gestured for them to do so. They lay there silently for a few minutes, before Sophie placed a hand on each of her maid's stocking-clad legs. She slowly stroked up and down, occasionally twirling her hands in circles. Tony was instantly hard and, from her increased breathing, Sarah was turned on as well. She slowly started to run her hands up their legs, to the hems of their skirts and beyond. The skirts rode up, exposing his red panties and he bulging cock they covered. Sarah was in a similar state; her panties were soaked already, Sophie was really good at this. Sophie gently manipulated Tony's balls and rubbed Sarah's pussy through their panties, causing Tony's panties to strain with the burden of keeping his cock in them. He felt constricted by the fabric and had the sudden urge to take them off. Sophie must have noticed his discomfort because the next thing she did was pull his panties down. She did the same for Sarah, and they were soon without their panties, that had now been thrown on the floor. Tony squirmed in pleasure and even more pleasure shot up his spine from his ass, causing him to squirm a bit more. He'd forgotten that he still had the butt-plug in, making almost every movement pleasurable. "Sarah, climb on top of me," Sophie instructed. "Tanya, lube your cock with her pussy, but don't stick it in." Both of them hastened to follow her orders and soon enough, Sophie was making out with Sarah, both of them fondling each other's tits while Tony rubbed his cock along the length of Sarah's pussy. He spread her juice along his shaft and pretty soon his cock was soaked. When she saw this, Sophie reached around Sarah and spread her ass cheeks, allowing Tony access. He took the hint and slowly slid his cock into his girlfriend's tight ass. He grabbed her hips while Sophie positioned her own cock at the entrance to Sarah's wet pussy and speared her with it. The two of them started fucking her and she moaned with ecstasy at the double-penetration. As Tony thrust in, Sophie pulled out and Tony's balls slapped into Sarah's pussy. Sarah was moaning loudly and it made Tony happy to know that he was at least helping his girlfriend feel good. Slowly, Tony and Sophie built up the speed and strength of their thrusts, causing Sarah to scream louder and more often. Within a few minutes, Tony could feel the cum welling up in his balls, but he held back. He didn't normally cum this quickly, but the situation was so hot that he could barely contain it. A few minutes later he couldn't hold off from cumming much longer and, with a grunt, deposited a large load directly into his girlfriend's anus. Sophie filled her pussy after feeling Tony cum. Tony pulled out breathlessly. He was about to apologise when Sarah turned around and kissed him fiercely. "That was amazing," she said, breaking the kiss. "Both of you." Even though he'd just came with all his might, Tony was hard again quickly, as was Sophie. It was time for a switch, and Sarah hovered her ass above Sophie's cock, holding herself in place with her hands. Meanwhile, Tony positioned himself in front of her. Tony and Sophie speared Sarah's orifices at the exact same time. The moan of ecstasy almost sent Tony over the edge again. This time, though. Sarah was all warmed up, so they didn't have to go easy on her. Within seconds they were ploughing into her like the pistons of a steam engine and Sarah was screaming like a banshee in the pleasure she was feeling. The room was filled with moaning and groaning from the three of them and, Tony was sure, the squishing sounds of sex underneath all that. It was a wonder there wasn't anybody in the house next door banging on the wall to tell them to keep it down. Before long, Sarah had a powerful, trembling orgasm, and her juices coated the shaft and base of Tony's cock. Some even dripped down and helped keep Sophie's cock lubed up. Before long, Tony felt his second orgasm coming on, and without being able to hold out, came inside his girlfriends already-cum-filled pussy. Sophie came at the same time and as Tony pulled out of her, Sarah slid herself off of Sophie. "That was amazing," Sarah said, rolling off of Sophie to lay next to her. "Yeah," Tony said, dropping onto the other side of his girlfriend. Sophie just grunted her agreement. They were all tired after the evening out and after a short amount of time, they all fell asleep.