Delectable Debbie

I can't explain why it was that I fancied having sex with a transsexual. I mean I'm a perfectly normal happily married man, couple of kids, mid-40s, a stone or so overweight but reasonable looking, my own hair and teeth and everything. I must admit, I've been with one or two...escorts, hookers, whatever term you prefer, over the years, but always very womanly ones if you know what I mean. I'd never felt attracted to nay bloke, and I certainly don't consider myself to be gay, or even bisexual, not really. But a while back, by accident, while browsing my favourite escort listings website, I came across a profile posted by a very tasty looking escort who turned out to be a T-girl, and, well, I started wondering what it would be like; what a cock would feel like in my mouth.

I decided to take the plunge on a recent business trip to London. If I was going to do this, I had definite ideas of what appealed to me: someone with a bit of experience, so not too young, not an Asian ladyboy, and most definitely not someone who looked and sounded like basically a bloke in a dress. I wasn't interested in being screwed myself, I wanted to be the one doing the screwing. I wanted someone British, who really looked like a woman, with a woman's voice and figure, but with that one extra appendage, as it were.

When I searched the escort website I was surprised how many listings I found: nearly 200 transvestites, T-girls, cross-dressers and so on in the Greater London area alone. I drew up, given that figure, a surprisingly short shortlist, but it was quickly clear that one lady (most seem to very much consider themselves female) stood out for me. She called herself Delectable Debbie: 32 years old, five-feet-five tall, dress size 8, with shoulder length blonde hair, pale complexion, a pretty smile, shapely legs, nice B-cup boobs (courtesy of hormone treatment), and not the slightest trace of an Adam's Apple or any seven o'clock shadow. The only indication of her true nature was a single picture in her private gallery, a naked profile showing an entirely hairless body and an impressive erection rising from her midriff. She had a dozen feedback reports on her services, all positive.

I phoned her a couple of days before I travelled down to London and I was impressed. Her voice was not in the least bit mannish, with a soft Scottish brogue, and it was clear she was intelligent and had a nice personality. We immediately seemed to hit it off, and she wasn't at all fazed by the fact that our meeting would be an entirely new experience for me; she assured me that she enjoyed meeting first-timers, and would ease me into my first T-girl encounter.

So, two days later, I took the train from Manchester to London, checked into my hotel, and prepared with mounting nervousness to meet Debbie. Showering and dressing carefully I left in plenty of time and, rather than get on a hot, crowded tube train during the rush hour, I walked across St James's Park in pleasant early evening sun to her place, an upstairs flat in an undistinguished looking terraced house in Victoria. She buzzed me in at the front entrance and I walked up a narrow flight of stairs to her front door, which was already open a crack as she peeped out. She hustled me into a dimly lit hallway, then nodded me towards a large brightly lit room, with a double bed to one side.

I certainly wasn't disappointed by my first view of Debbie in the flesh. She was as pretty as in her photos, dressed in a silky black nightdress, trimmed with red lace, which ended at mid-thigh, giving me a generous view of her bare legs. On her small pale feet she had a pair of fluffy pink slippers which revealed slim toes, the nails painted a dark cherry red. Taking my coat she offered me a drink and, my heart racing with nerves, I gratefully accepted a crisp white wine.

Debbie sat on an old saggy sofa and patted the seat next to her with a wide smile. I left a few inches of space between us but she shuffled beside me, her thigh pressed to mine, her warmth radiating through my trousers. We chatted and sipped our wine for a while and I began to relax, more or less forgetting this was more than simply an attractive young woman sitting next to me. After a few minutes she finished her wine, took my glass from my hand and, placing it on a coffee table, slipped a long slim arm around my neck, pulling me to her. We began to kiss and Debbie immediately slipped her tongue into my mouth, stroking it across my own tongue. She was a great kisser and I felt very comfortable with this, one arm around her neck, my other hand gently massaging her soft breast through the nightdress.

I soon felt pretty aroused and, sensing that, Debbie stood and said "I thought we'd start with a nice relaxing massage if that's okay, honey. So if you want to strip off and lay down on the bed I'll just go and get my oil." She left the room, and as I stripped I heard her humming a tune to herself as she moved around in her bathroom. I lay down and made myself comfortable. When Debbie returned I glanced up; she had removed the nightdress and was now dressed only in a tiny pair of black silk panties. I couldn't see any obvious bulge in them, but in a moment she was kneeling beside me on the bed, pouring a trail of warm oil across my back. She had a good massage technique, kneading my tense muscles, and I shivered as she leant forward and ran her tongue softly around the curves of my ear, then gently nibbled on the lobe.

Debbie then sat astride me to work on my back. I felt her nipples lightly trace down my back, then she began to massage my bum. Her fingers slipped lower, and on each stroke she ran her fingertips across my scrotum, then up between my cheeks, like swiping a credit card. That felt very sexy, and of their own accord my hips started to lift to meet each teasing stroke. She took advantage of that to cup one hand around my balls, one finger tracing lightly up my now very stiff cock. With a very girlish giggle she murmured "I think you're ready to turn over now Charlie."

Debbie was still astride me so I turned beneath her, and she grinned at the sight of my erection, then chuckled, "Ooh, that looks nice. I think that deserves a special massage, don't you?" She climbed off me for a moment and, her back to me, slipped off her panties. She had a gorgeous slim bum, and, as she climbed onto the bed again, I caught a first fleeting glimpse of her cock. Then she lowered her head to my groin and shuddered with pleasure as her lips slipped over my shaft. God, she was good at that; she caressed my length with her lips, her tongue tickling the sensitive underside. Occasionally she would slip her mouth right up to the tip of my dick, sucking hard on it and flicking it with her tongue, before plunging her lips back down me. She cupped my balls in one hand and gently squeezed them rhythmically, sometimes massaging the root of my cock between thumb and forefinger. After only a few minutes of that I was ready to explode; I warned her I was about to cum, but she just responded "Mmmmm," and licked and sucked me all the harder until a erupted deep into her mouth, my hips jerking at her spasmodically. She sucked me dry then, meeting my eyes with a smile, whispered, "Mm, you taste niiiice, honey."

She started to slide my body and, for the first time, Debbie's erection rubbed against my own. She noticed me shudder at that and, giggling, gently swayed her hips from side to side for a few seconds, our stiff cocks and our balls caressing each other. Then she continued to slide up until one of her nipples pressed against my lips. I willingly parted them and began to suck and nibble on the dug. Debbie gasped and pressed more of her boob into my mouth, circling her hips and pressing her erection into my belly. (She explained that because of the hormones her nipples were especially sensitive.) She seemed to go wild as I sucked first one nip then the other, then almost gasped, "Do you want to suck my cock?"

I'd been preparing myself for this moment, and I smiled and said I'd like to. Debbie shuffled up until her cock and shaved balls were an inch from my lips. I licked her balls and she gasped and shuddered; then I eased her hips back slightly and took her erection into my mouth. I hadn't been sure what to expect, but it felt burning hot, and like a metal rod wrapped in soft velvet. After the initial strangeness I began to enjoy the sensation and suck hard, swirling my tongue around the length of Debbie's prick. Debbie sighed with pleasure and shuffled her knees forwards on the bed either side of me. She began to ease her hips back and forth, fucking my mouth, her hands cradling my scalp and gently massaging my head. I reached around her and cupped her buttocks, massaging them as I sucked on her dick. She started to moan as she came closer to cumming; I began to worry slightly about her releasing in my mouth but then she withdrew. She pulled me down beside her on the bed and locked her mouth to mine, kissing me wildly and wrapping one of my hands firmly around her cock. I rapidly wanked her, and she screamed into my mouth as she shot her load in a fountain above her.

Debbie continued to shudder for a little while and I cuddled her, kissed her, and sucked on her nipples again until she asked me to stop. I was hard again by then, and Debbie slipped her mouth onto the tip of my prick and sucked it for a few seconds, then turned on all fours and presented her cute bum to me. She handed me a tube of lube and I squeezed it onto my fingers and liberally smeared it around her anal cavity. Then I rolled on the condom she had given me, gripped her hips and slowly eased into her.

I'd never had anal sex before and at first I eased in and out quite gently, but Debbie urged me to do it harder several times, until finally I was pounding into her, to the hilt, her bum cheeks rubbing against my belly with each penetration. She was quite tight and it was one of the most satisfying fucks of my life. As I came close to climax I reached around Debbie and grabbed her cock, stroking it as I thrust into her. She gasped "Oh fuck yes," and started to push back hard to meet each of my thrusts. When I climaxed I banged in to Debbie with one final huge stroke that made her gasp. She wrapped a hand around mine on her prick and helped me to continue to wank her until she came again a few seconds later.

Debbie and I had such a great time that she let me stay for a while after the time I'd paid for and sucked me off again before I left. I'm still very much into women, but I'll certainly be seeing Debbie again next time I'm in London, and if I can find another nice T-girl in my local area I'm definitely going to set up a meeting with her.