My name is Rose and I’m a transsexual! Ha, this sounds like the start of a group therapy session but it isn’t, I promise. I’ve always liked to be open about my sexuality, although it hasn’t always been easy for me.
I’m only 25 but I always knew I was a girl trapped in a boy’s body. I’m not going to bore you with the angst and self-searching of my teenage years. Yes, there was plenty, but I come from a very grounded background with a supportive family, so I don’t think I’ve suffered like some trans girls have done. No, for me it was a rather surreal journey of discovery. I’m blessed with a naturally quite feminine body, smooth skin and very little body hair. I did get teased when showering after games at school, that was until about the age of 14. You see, despite my feminine body, my dick was bigger than any of the other boys who showered with me. This got me some man-points at school and there were a few rumours going around about me which I didn’t mind. A couple of the girls got curious enough to ask me about it and even though I was actually more attracted to the boys, I liked the attention, if I’m being honest.
I lost my virginity to a girl at a party when I was 15. Too much sweet cider for both of us had our adolescent fumbling turning into something more intense. The experience was brief but very pleasurable. What I didn’t know was the girl I’d been with was rather loose-lipped and the rumour mill started again in earnest. It seemed like everyone knew we’d had sex and a few of my friends quizzed me about it mercilessly. I didn’t kiss and tell though, preferring them to use their imaginations. The kudos of being one of the first in my year group to do the deed kept the bullying at bay. That and the fact that I’m quite athletic and held the school record for the 100 and 200 metres sprint. This made me a minor celebrity for a couple of years and helped me take my mind off the fact that I knew I was bisexual and really wanted to be a girl.
My best friend Ian and I used to admire the prettier girls in school. We talked about what it would be like to actually fuck them and how sexy their bodies were. I was in fact thinking about how lucky they were to have breasts, wide hips and the clothes they wore, and how I wish I could be like them. I never confided in Ian as he was rather an alpha male kind of guy and I valued his friendship. I suspected if he knew I fancied him as much as the girls we ogled, he might not be too pleased!
I managed to do quite well at school and got a place at University studying art. The course was easy and it gave me plenty of opportunity to meet new people and even experiment with my sexuality. I started to dress more androgynously and tried wearing make-up when going out. I don’t want to sound big-headed, but I’m quite nice-looking, with soft features and high cheekbones. I was lucky to attract some very nice girls and the boys seemed interested in me too. It was at the end of my first year at Uni that I lost my virginity for a second time. I hooked up with a very nice boy who was kind and patient. He persuaded me to let him fuck me and it was the most amazing experience of my life. I owe this man so much. I’ve heard of nightmare stories about gay guys’ first times so I was very lucky that Andrew was mine. He was two years older than me and quite experienced and he made my first time with a guy thrilling, loving and erotic. I was still seeing the occasional girl at that time, and whilst I still loved having sex with them, Andrew had opened my eyes to what sex could really be like.
It was during my second year that I started to transition. I confided in my mother that I really felt more like a girl than a boy and had done for as long as I could remember. She didn’t seem fazed at all by what I thought was a revelation. “Sweetie, I always knew you weren’t like your brother, so much more loving and sweet-natured. Dad won’t be surprised either and don’t forget, one of his best friends is gay, so I don’t think you need to worry about his reaction.” Wow, I was surprised and delighted by her reaction. I was dreading telling Dad, so when Mum said “I’ll have a little chat with your Dad, don’t worry. Then you can tell him yourself and we’ll take it from there.”
Mum and Dad were both so supportive. My brother, Billy, wasn’t quite as easy to win over. He seemed more worried that I’d used to bath with him when we were little and more worried about what his friends would think. When I assured him I liked girls as well as boys and that my sexuality had no bearing on his, he seemed to relent a little.
What I hadn’t told them was that I was intending to become a girl, albeit one with a cock. I wasn’t going to have that cut off in a million years. I was proud of it and loved the way it felt when being sucked by an eager mouth. Plus I’m a bit of a coward when it comes to surgery. I knew I’d have to have fake boobs, but the thought of somebody waving a scalpel anywhere near my private parts made me shudder and I quickly realised I’d never go down that route. I worked all summer and saved hard for my boobs. I must have started my own facial and body transition quite well because I got offered and I accepted a modelling job soon after finishing Uni. I was officially a degree-educated transsexual model and I started to feel good about myself for the first time in a long time.
Model work was a bit sporadic to start with and I started to consider the offers of glamour work. I had a word with an agent I knew who I figured would be sympathetic to my situation. Nicola was very obviously a lesbian and had made it clear that she fancied me. I figured if I told her I was transsexual, it would put her off, but it seemed to excite her even more. “Wow, really? I had no idea, you look so natural!” was her immediate response. “Can I see?” she asked, cheekily. She needed proof, and that made me feel more feminine as well. We slipped quietly off the set we were working on and into one of the toilet cubicles. I raised my short skirt up and untucked my penis from between my legs. It sprang out and the look of shock on her face was a picture! “Oh my God, that’s fucking huge!” I heard her say. She was shaking her head in disbelief as she reached forward to touch it. Then hold it. Then stroke it. It got even bigger with her attention and she looked up at me and said “Honey, it’s been a while, but…” and promptly started to suck my big throbbing cock.
Damn she was good! She swirled her lips and tongue all over the head of my cock, she fondled my testicles and even rubbed a finger up and down my ass crack. She started to take me deep into her mouth and sucked like she really wanted me to cum in her mouth. I hadn’t cum for a few days, so it wasn’t long before I felt a tingling in my groin and started to sigh deeply. “I’m gonna cum,” I whispered and relaxed my muscles as I filled her mouth and throat with several spurts of cum, which she swallowed, sighing how beautiful my cock was. She stood up and looked at me with cum dripping down her chin. When she kissed my mouth, I tasted my own cum for the first time and it was an incredibly erotic feeling, one I wanted to repeat with whoever I would fuck with next.
Nicola promptly signed me up to do some specialist glamour and hardcore model work and I ended up earning some very good money doing magazine and still photos for websites. It was an easy transition to doing video shoots and porn, but despite the money, the sex always left me feeling like I wanted more. The work was a bit sporadic and I needed more regular money to furnish my newly-acquired lifestyle. I needed a plan. One of the movie directors I worked with had often said if I wanted to meet with him after work, just say the word. I was tempted because he was a great-looking guy, so I decided the next time we worked together, I’d let him know I was up for it. Despite the on-screen sex I was getting, I still needed to feel loved and to have some properly erotic sex.
A few days later and Nicola called me with a booking with the studio Tag, the director, worked for. I decided that despite his stupid name, I would make it clear I was ready to meet him if he was still interested. We shot the movie, which was fairly ordinary fare, me revealing then stroking my big cock and then fucking and sucking with one of the nicer actors I’d worked with. Tag was very complimentary all the way through the shoot and very attentive to my needs. When we’d cleaned up and dressed, he asked me to come over and view the rushes with him. I must be a bit vain as I quite liked seeing myself on screen, straddling a big cock and having my own sucked. We looked good! Tag kept saying how beautiful he thought I was and how much he’d love to ‘spend time’ with me. Spend some time horizontally, no doubt. I looked up at him and said “Well, if you really mean it, I’m free tonight actually.”
Tag grinned and said “Oh Baby, that would be awesome. Give me your address and I’ll be round about 7 if that’s OK?” I nodded and tapped my address into his phone notepad, kissed him on the cheek and left the studio. I took extra care getting ready for our date, wondering where he might take me. I dressed in my sexiest, most expensive underwear and I was applying the final touches of makeup as I heard Tag knocking the door, just before 7. I slinked sexily to the door (well, I was slinking sexily in my mind) and tried to relax. Even though this guy had seen everything I had to offer several times, I was still a bit nervous. He breezed in, kissed me on the lips and complimented me on my appearance. He looked pretty damn good too. The place where I lived at the time was no more than a large bedsit, just one room which was the bedroom and lounge combined. There was also a kitchen and bathroom, of course, but inviting Tag into my home was immediately like inviting him into my bedroom. This seemed to tickle Tag as he wandered over to the bed and sat on it. “Join me?” he asked. He knew what he wanted and all thoughts of preliminaries and a proper date went out of the window. I sat next to him and he leaned in to kiss me.
Within seconds, his hands were all over my body and we snogged for ages. I was getting aroused and when Tag reached his hands down to my groin, my heart beat a bit faster and my cock got a bit stiffer. He was stroking my cock through my panties and unzipping his jeans with his other hand. “Stand up, Babe,” he asked and I stood in front of him as he sat on the edge of the bed. His jeans and boxers were now down around his ankles. His cock was standing to attention as he pulled me closer to him, lifted my skirt hem and slipped my panties down. This made my fully hard cock spring up towards him and Tag just sat there, his eyes wide with admiration. “Baby, you’ve no idea how much I’ve wanted to do this,” he said, as he took my cock into his hand, leant forward, then wrapped his lips around it. He sucked me long, hard and deep, savouring the size and taste of my cock. His hands were kneading my ass cheeks and I was breathing hard, surprised by how good he was at sucking dick and how quickly I started to feel the urge to cum, especially considering we’d shot a scene only a few hours ago. I pulled back, knelt down between his legs and pulled his jeans and shorts from his ankles. He lay back on the bed and I started to work on his cock. I love the feeling of taking a hard cock into my mouth for the first time with a guy. I love to feel it twitch and to hear his reaction to my soft lips and eager tongue. Without being immodest, I’m a pretty good cock-sucker! Practice makes perfect, they say, and I’ve had quite a lot of practice now. I’m also able to throat a cock without gagging, so I can go deep on any cock, no matter how big. Tag’s was almost as big as my own, but that didn’t faze me in the slightest. I can even take a cock into my throat and push my tongue out far enough to lick the guy’s balls at the same time. Tag enjoyed me doing this so much, he started to cum without warning, making me choke a bit on the amount of cum he was pumping into my throat. I kept sucking like a good girl until his knees went weak and he pulled away. I climbed onto the bed and lay next to him, hoping he’d kiss me and share the taste, but he didn’t. “I’m gonna need a few minutes to get hard again, but when I do, I’m gonna fuck that sweet ass of yours!” said Tag. Well, that was just fine by me. My cock was still hard and my ass was twitching in anticipation. I shuffled up the bed so Tag could reach my dick and he started to suck me again. He slipped one, then two fingers into my ass hole making me squirm. I could feel his cock getting hard again, so I rubbed it against my thigh. I could feel the orgasm welling up in my loins but I was unsure whether or not Tag wanted me to cum in his mouth. I moaned loudly to give him a clue and he picked up on it.
“I’m dying to fuck you Rose,” he breathed huskily. I reached over to the bedside table and found a condom. I quickly opened it and rolled it on to the full length of his cock, then lifted one leg over Tags hips. I eased myself down so my ass hole was poised over his throbbing cock head, relaxed my muscles and slid the entire length of his cock into my ass. Tag let out a loud groan of pleasure and I started to ride him slowly, gradually increasing the speed. If the meeting started with him in control, it ended with me controlling things. I bucked my hips and thrust myself down onto Tag, leant forward and kissed him, then leant back so he could fondle my breasts and I wanked my own cock in time with our thrusts. Tag’s eyes were closed with the blissful feeling of my ass clamped tightly around his cock. I love riding a guy and I decided to stay in this position until he came again. I wanted to time it so we both came together. I was surprised that Tag was close to cumming again, although when I looked at the clock on the bedside table, I realised we’d been fucking for well over an hour already.
I could feel his cock twitching deep inside my ass and his moans grew louder. I stroked my own cock harder and faster, more than ready to shoot my load over Tag’s belly. He gripped my hips and shouted “Oh my fucking God!” as he filled the condom. The feeling of his huge cock pulsating inside me tipped me over the edge and I pulled my foreskin right back as five thick spurts of cum shot over Tag’s chest and belly. I had never cum so hard before and felt totally drained. I slumped down hard on Tag’s groin and he winced as his cock was so sensitive after his second orgasm of the evening. I said “Sorry Babe!” and laughed a bit, as I traced my fingers over Tag’s cum-splattered belly. I couldn’t resist covering my fingers with my own cum then licking it off them. I ran my fingers over Tag’s chest, scooping up some more sticky cum, then offered them for him to lick. He did so, but very tentatively, so I leant forward and kissed him instead.
We were now both totally wasted and it was barely 8.30. I figured maybe dinner or a movie, so I was a bit taken aback when Tag said “Rosie, that was amazing. I have to get back to the studio now, but I’d love to see you again some time.” He slid off the bed, wiped his body down with a dry towel and started to dress. I slipped into the bathroom, freshened up a little and re-joined Tag in the main room to find him counting out bank notes. He handed me two hundred pounds and said “I think that’s about right for your time, don’t you?” I wasn’t sure how to react, so I smiled and nodded. He kissed me on the lips and turned around with a cheery “See you soon, I hope,” and disappeared out of my front door. I sat down on the edge of the bed and counted the money. I was feeling a bit deflated, like I’d just been used. Was I a whore now? Well, I’d just been fucked and paid for it, so I guess I was. The plan I had needed had written itself.
Over the next few days, I had no modelling or film work scheduled so I spent time thinking and planning what I would do next. I scanned the small ads for a bigger apartment, researched the local escort adverts, read up on escort reviews online and made my decision. I would become an escort to supplement my modelling work. If I had no modelling and could see one client a day, I could still make a thousand pounds a week. This could be lucrative and fun at the same time. It was a bit scary, but exciting. I found a chic apartment in one of the nicer parts of town and got a friend to help me move my stuff in. It had two bedrooms, what a luxury for me, so I decided to use the one that had the en-suite bathroom as my ‘business’ room and keep the other one for my private room. I had great fun decorating it and tried to make it as erotic and inviting as I could. I laughed to myself as I realised it didn’t really matter. Once my panties were around my ankles and my big cock standing erect in front of a client, they wouldn’t give a fuck what cushions I’d chosen!
I looked at all the websites that offered transsexual escort services and decided on one specialist one to advertise on. It wasn’t as expensive as I had thought it might be, which was good as I was now spending much more money on rent and had spent far too much on decorating. However, at the rates I was intending to charge, clients would expect decent surroundings. I know I would. I looked at the website as my advert went live and got a tingle of excitement. I wondered how long it would take to get my first enquiry. I’d bought a second phone so I had a dedicated number to use. I wanted to keep my escort life and real life separate as far as I could, so this seemed like a good idea. I was amazed to hear the text bleeper go off on my new phone within half an hour of my advert going live. I’d read that there are a lot of time-wasters and chancers in this game, so I didn’t build my hopes up too much. Sure enough, it was a text saying “I wanna fuck you!” from a withheld number. Probably a teenage wanker, but I didn’t care. It proved my phone worked and that my ad was visible.
Ten minutes later, the phone rang and a very polite voice said “Hi, is that Rose?” Bingo! “Yes, Darling,” I replied, “how can I help you?” The chap named Steve asked me for an appointment later that week, so I booked him in and sent him a text with my postcode so he knew where to come. My first client!
If you want to know what happened when Steve came to see me, have a look at the story entitled “Trans Delight”. https://noveltrove.com/story/2191/trans-delight Steve was my first client and my favourite yet. He’s come to see me a few times now and each time we have an amazing meeting. I get so carried away, we always overrun our time and Steve is so sweet. He always offers me extra money but I never accept. I may be a whore, but I have standards! We have a connection like I have with no other client. He will always be my proper ‘first’ and I have a real soft spot for him. A soft spot and a hard cock! We make each other laugh and a meeting with him never feels like a business transaction. He’s kind, considerate and sexy as hell!
I’ve built up a small but regular client base since that first meeting. I still do a bit of modelling and film work and I’ve even had a few repeat meetings with Tag, always paid for. I’m under no illusions that I’ll find my soul-mate while working as an escort, but very good money and regular sex will do me for now.
That is, until I can persuade Steve to leave his wife and marry me!