First Time With A TS

It was an itch I needed to scratch. It had started months earlier, one evening when my wife and teenage daughter were downstairs watching their favourite soap opera and I was upstairs in my office trawling my usual punting site to see if any interesting new escorts were around for my next trip to London.

I'd only ever looked at – and been with – women before, but somehow I got side-tracked into looking at the profile of a pretty transsexual. Intrigued, I looked at one or two more. Within a couple of weeks I found I wasn't looking at female profiles on the site at all, just at the T-girls. I felt confused; I'd never been attracted to other men before, but the combination of a pretty face, nice boobs and legs and, right at the middle of it all, a big rearing cock, had started to fascinate me, and become quite a turn-on for me.

So, a couple of weeks ago, I had a couple of business meetings set up in London, which involved an overnight stay. Nervously, wondering if it was really what I wanted to do, I had a look at the T-girls I'd short-listed on the punting site. I narrowed it down to a lady called Ursula, Swiss, 28 (ten years younger than me), slim but busty, a pretty face with straight blonde shoulder length hair, high cheekbones, blue eyes, and wide full lips that looked like they were made to suck cock. She was also a qualified masseuse, which is always a bonus in my book. Before I lost my nerve, I called her number. She had a deep voice but not an unfeminine one, and purred down the phone to me with a sexy European accent. So we arranged the details and I hung up, my heart already racing at the prospect.

My meeting on the day I was due to see Ursula didn't go well and I was feeling pretty crap by the evening. To be honest I nearly called her and cancelled, but I thought maybe a massage would relax me, even if I chickened out of anything else. So I took the tube to Hampstead and made my way to a quiet residential street and the modern four-storey concrete and steel apartment block where she did her business. She buzzed me in and I walked up to the second floor.

When she opened the door I was immediately glad I hadn't called it off. Ursula was even more beautiful in person than in her photos. She was dressed only in a silk thigh-length kimono which revealed a small amount of her substantial bust, and even barefoot she was a couple of inches taller than me (I'm five-feet-nine). Her nails, finger and toe, were painted scarlet. She greeted me with a warm smile and a peck on the cheek, invited me in and led me across the large stylish lounge we'd entered to a black leather couch, my eyes glued to her pert swaying bum and her long shapely legs. Offering me a choice of drinks, she sat me on the couch and brought us both a champagne flute filled with sweet sparkling white wine.

Ursula sat very close to me, her manicured hand on my thigh, and we chatted for a couple of minutes. Ursula told me this was only a part-time job for her and that she worked in the City as a software engineer. She then asked me what I was looking for. I told her I needed a good massage, and that this was my first time with a T-girl and I was open to whatever happened. (Even as I said it I wondered if it was true, and my heart started to race.) She took my half-drunk glass of wine from my hand and placed it on the table beside hers; then she slid her arms around my neck, pulled my face to hers and kissed me. Her tongue flicked against my lips and I opened up to a deep and very erotic French kiss. At the same time her hand dropped into my crotch and I could feel my cock straining to be released. Her kimono had fallen open and my hands found their own way to her big firm boobs, my fingers rolling her erect red nipples. After perhaps 20 seconds she broke the kiss, sat back and, with a chuckle, murmured "Okay, Phil, I think you're ready for that massage."

Taking me by the hand she led me through to a low-lit jasmine-scented bedroom barely wide enough for the double Futon bed which nestled close to the floor. Her kimono slipped from her shoulders and I saw her naked for the first time. I was relieved to note that her cock wasn't the ten-inch monster I'd feared, but was actually a little smaller than mine; big enough, though. Then she stepped towards me and, as if to test my commitment, took my hand and wrapped it, just for a moment, around her stiffening dick, before undressing me. She simply slipped my buttoned shirt over my head and off, then knelt before me, removed my shoes (I never wear socks on a punt), unbelted my cargo pants and pulled them and my briefs down in one go. For a second she slipped her lips over the tip of my erect dick and swiped her tongue across it, making it twitch in response. Then she told me to lay face down on the bed.

She poured warm oil onto my back then spread it around with big, strong, soft hands. She then sat astride my waist and started to massage my back. I could feel her balls resting on my back, and it felt quite strange. She leaned down and whispered close to my ear, "My god, your shoulders are like teak. I'm gonna have to work hard on them."

Standing she moved to the head of the bed and, kneeling, reached over my head to start working her fingers and thumbs into my tight muscles. As she did so, I'm sure by design rather than accident, her cock brushed against my cheek. It was clear what she wanted me to do and, with a mental gulp of nervousness, I shifted my head and allowed Ursula's stiff dick to enter my mouth.

It felt strange, but not unpleasant; the best way I can describe it is like an iron bar wrapped in velvet, with a rubber tip. Accommodating myself to it, and enjoying Ursula's firm touch on my shoulders, I started a slow rhythm of sliding my lips back and forth along her length and swirling my tongue around it. She seemed to be enjoying it because I'm sure her cock swelled in my mouth.

She allowed me to suck her for a couple of minutes then gently disengaged and walked to the bottom of the bed. Ursula's certainly a skilled masseuse – my shoulders stung, but they did feel more relaxed. Easing my legs apart, Ursula knelt between them on the bed and reached up to massage my back, her tits brushing against my bum and thighs. As she worked her way down she lightly scratched her fingernails across my buttocks, which felt very erotic. With each down my bum and between my thighs, her fingers briefly caressed my balls, making my cock painfully stiff. I gasped slightly as she wormed a finger deep into my bum, which felt surprisingly comfortable and satisfying. Then she grasped my buttocks and pulled them apart before I felt another sensation – it took me a moment to realise it was her tongue, pressing into my anus and tickling me. I realised I was actually gasping with arousal.

She pulled back and returned to the bottom of the bed. Clearly not rushing things, she massaged one foot and made her way up my leg, then did the same on the other. She left the bed for a moment, then I felt her kneeling between my thighs. She pulled my midriff slightly off the bed and placed a couple of pillows beneath me, raising my bum. Then her hand was inside me again, but this time spreading something wet and extremely cold around my cavity. I heard the familiar sound of a condom being ripped open, then a few seconds later there was an intense pressure on my sphincter and I realised Ursula's cock was pressing inside me.

She lay the length of her body atop mine and whispered "Tell me if it's too hard or you want me to stop." It was a very weird feeling at first but she took it slowly, pushing in until I felt her body pressing against my bum and I knew she was in me to the hilt. She started to fuck me, gently and rhythmically, and after the initial shock I found it was a sensation I enjoyed. Involuntarily my bum even began to thrust back at her with each stroke. As she approached climax she began to pant and rapidly increased her pace, gripping my hips in her hands. She gave a huge groan and I felt a sudden warm surge inside me as she shot her load into the condom. She gave one big final push then lay down on my back, her fingers interlaced with mine.

After about 15 seconds Ursula roused herself and withdrew from me. She wrapped the condom in a paper towel and mopped me out with a couple more, then told me to turn over. She stretched her length along mine, her tits resting on my chest, and kissed me deeply. Then, applying some more oil to my chest she worked it in and started to make her way down my body. As her face came level with my groin she slipped her lips onto my rampant cock, and started a face fuck me. With one hand she clutched my balls, gently squeezing them and stroking the tips of her nails across my scrotum. With all the stimulation I'd already had I knew I wouldn't last long but I strained to hold on. Finally I had to gasp "I'm about to cum." Ursula gave me a thumbs up to show she'd heard me but kept right on sucking. My restraint failing me, I burst into her mouth, my hips thrusting forward. She sucked even harder, greedily swallowing my cum and wanking the root of my cock with one hand. I sank back, my chest heaving, and once again Ursula climbed up the bed and kissed me, this time smearing my own spunk around the inside of my mouth.

By then the time I'd paid for was just about up, and I went to rise off the bed but Ursula gave me a Cheshire cat smile and pressed me back down. She shuffled up the bed until she was astride my chest, her cock rearing before me, and I obediently opened my mouth to receive it. Ursula shuffled her hips back and forth, helping me to pleasure her as I sucked and licked at her straining knob. It hadn't occurred to me that I was being rash giving a hooker a blow job without protection, but thankfully before she climaxed she pulled out of my mouth, grabbed my hand and encouraged me to wank her to a finish. With a wicked grin she licked her sticky cum off my hand.

I would have liked to fuck Sylvia, and she would have been happy to give me the time for free, but I was out of juice. We lay kissing and cuddling for a while, and I enjoyed the feel both of her breasts pressing against me and of her cock and balls rubbing against mine. After that we showered together, with her pushing her hand deep into my bum crack, then she dried me and I dressed. As I left we shared one last deep kiss then, her arms still locked around my neck, Sylvia told me, "You know, baby, I think I'll be seeing you again next time you're in town."

I think she's right.