The Third Gender

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Adventure in ladyboy fantasy.
1.4k words
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I told my friend and housemate that I was going out for some beers. I didn't want to let on for a moment where I was really going. It was just the sort of thing that doesn't go down to well in some company.

I made my way to the train station and found a phone. I called ahead to a place that looked suitable to my needs and waited for the next train. The whole trip towards my destination was marked out by nervous distraction. I was trying to weigh up the pros and cons of what I had in mind. It was impossible to deal with from an ethical standpoint so I instead gave way to desire.

When the train arrived I was deep in doubt about the whole thing. I went to the nearest hotel and bought some beer to calm the nerves and after about four or five I was able to overcome the fear and continue on. The establishment was back near the train station and I slowly made my way over, ringing the doorbell when I arrived. I was greeted by a very unconvincing transsexual.

The place itself was nice. It was a two-story terrace house. I was ushered to a waiting area just off the foyer. When seated I noticed one of the staff heading upstairs and again it was a very obvious she/he, possibly African.

All this had me worried all over again so I asked if I could meet with my potential sexual partner, seeing as I had already paid and didn't want to end up with some guy in drag. I was after an experience with someone as ambiguous in their sex as to warrant a third gender. The receptionist was happy to oblige. A phone call was made and shortly after I was greeted by a stunning oriental girl in a hugging crop-top, miniskirt and stockings; all black. The vision of this sensual creature was sufficient to allay any reluctance I might have felt. In a polite feminine voice she introduced herself to me and took my hand. It was this action which for a fraction of a second brought me back to the reality of the situation. Reality was the last thing I was looking for that night. What happened was: her hand, although not large or weathered, gripped mine with too much authority and it reminded me of both why I was there and why it bothered me. Was I just about to sleep with a man or a woman or something altogether different? I was undoubtedly fishing for the latter but with that said I was sufficiently captivated and ready to cast aside any real reservations in favour of the experience itself, whatever that might be.

She spoke in endearing broken English that was easy enough to understand. She was asking if I wished to go upstairs and as it happened, I did. Her legs were amazing. The curves of her calves and thighs were demanding attention without being confronting in either a masculine or feminine way. Her hair was stylish in a very Asian way and her face was to die for. I was reeling with confusion but not confused at all about what I now wanted, and so I followed her up a flight of stairs and down a narrow corridor to a heavily mirrored, but not overly tacky room.

By this time I was ready to dive straight in, as it were, but she asked if I would like to shower in a tone that suggested it was the right way to proceed. I took the instructions and wandered off to the bathroom across the hall to shower. When I was done I repaired to the room we were in only to find myself alone. I was sitting there in just a towel, looking at my reflection in the mirrors and wondering foremost what she would think of me. I had payed a not inconsiderable sum for this and I was still being self-conscious and egotistical. Shortly she returned in a short silk robe that just covered her arse. I could tell by the contours in the gown that she had a comparable if not better behind than the sexiest women I had been with. She placed a towel on the bed and inspected my prick for visible signs of something that might stifle her working life and, on seeing nothing suspicious, started making conversation. It was unsettling because I then had to assimilate into the equation, her humanity. I had to think of her in a personal way that was not commensurate with the experience I had sought. It makes me think of the way a negotiator in a crisis situation will try to make the potential victim become a person in the perpetrators eyes rather than an object.

I looked her up and down, as she did me. I was impressed by what I was seeing and I feel it's fairly safe to say she was happy with her client. Her eyes lit up with interest as she explored my tattoos and asked me what I wanted to do. While I was considering this she let her robe drop to the floor. When I saw her standing there with her spotless brown skin and perfect little hormone-induced tits, in nothing but a pair of black panties, I had plenty in mind as far as wants go. I wanted to abandon myself to days spent exploring the nuances of her flesh, but this was not on the cards so I tried to refine my requests to what was practical given time limitations. She asked if I wanted her to suck me. I said I did but not too long as I didn't want to come prematurely and ruin the whole thing. To my utter surprise she lent into my body and kissed me squarely on the lips, which is not done in the industry as a rule. I surprised myself by accepting this without question and drank her in deeply, feeling the fullness of her lips against mine as our tongues worked between them. Her breasts were small and firm as I took them in hand and mouth. Kissing her way she found my prick and enveloped it with a condom in her mouth. I was terrifyingly hard and didn't let her work to long at it as I really was in danger of losing it.

Looking at her again standing before me I felt the need to consume her. I asked if I could suck her off and she said yes with a smile as she rolled a rubber over her flaccid cock, which was smaller than mine and uncircumcised. I wanted so badly to feel the flesh in my mouth that I lapped at the base where the skin was exposed. She pulled it down to cover the whole shaft to make sure protocol was not broken. I resigned to the fact that, sensible as it was my fantasy in that regard would remain unsatisfied.

The rest of the sexual part of the encounter seemed to go very quickly. She lay down on her back, spreading first the towel beneath her on the bed. I would rather have taken her from behind but I was ready to consummate this arrangement and followed her lead, positioning myself above her missionary-style. I once again found myself locking lips with her and it was really a large part of the pleasure if truth be told. She guided me into her arse with consummate ease. She felt tight around me but not unyielding. I started to pump out a rhythm and busy myself with her breasts and mouth as I went. She was groaning but I figured this was a given part of the script. Her cock had grown somewhat hard and was pressing against my belly. After a fairly short while I came violently. Instantly, I had pangs of regret and insecurity. I shook these sentiments off as best I could and pulled my shrinking member from her. She was still moaning and carrying on. I thought to myself it was a bit late for an Oscar but she said soon after: "I'm not supposed to do that". I looked down at her crotch and it occurred to me that she had blown a load in the condom. It made me wonder if she meant that it was against house rules to come or if her doctor had told her that it probably wouldn't happen anymore.

After that she massaged my back and made small-talk on boyfriends and girlfriends, tattoos and what not. I had started feeling like it was all a big mistake and my body was going rigid with the sensation that I was subject to a violation. Of course it was more a case of self-doubt corrupting the moment but I had to get out of there and process it all another day.

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AnonymousAnonymousabout 18 years ago
A rather intelligent and insightful piece

I'm not one to leave comments, but there's a satisfying bit of pathos and thought in the story that lends it credibility and readability; definitely the literature part of 'litererotica'. I hope to read further submissions in the future.

AnonymousAnonymousabout 18 years ago
interesting and sexy

This story has the ring of truth about it. I love the writer's self doubt and the heady mix of pleasure and guilt. Well written. Very very sexy.

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