Shemale
2009-04-07

Let me set the scene- I was in a bar lonely and away from home. This girl was there and she seemed friendly – I bought her a drink and we moved to a booth where we were inconspicuous and could have a conversation without being overheard.
We had a few more drinks and she became very friendly and I thought I was onto a interesting proposition and thought I may be able to talk he into coming back to my hotel room with me.
The barman gave me a wink the last lot of drinks I bought and I thought well a wink is a good as a nod and I was onto a certainty.
I made the offer and she agreed – I was home and hosed I believed.
We got back to my hotel and we had another couple of drinks from the mini-bar and the bed was getting closer. Finally we kissed and the passion scale went sky high and I knew I was onto a good thing – sex was a certainty. She never hesitated when I began to fondle her breasts and she willingly exposed them for me. They were firm and I suspected a breast enhancement but said nothing – they still felt good and I was enjoying them and gradually working my way further south. She was a step ahead of me and before I could completely undress her she moved on me and I was suddenly having my pants pulled down and I was enjoying one of he best cock sucking experiences I had ever had. She was an expert and knew how to get me almost to the point of climax, then kill the sensation or reduce it and then resume bringing me back to my climax again – and again. I never really came until about the fourth time she brought me up to it. She was an expert and knew how to handle my balls and fondle my cock and masturbate me as she sucked semen from down deep within my prostate. She even knew how to finger my ass and stimulate my prostate as a doctor does when he gives you a prostate examination. I even asked as she was doing it and the semen was streaming out of my cock and into her mouth without me cumming, if she was a nurse.
She answered how did you know – and it was obvious she realised I had been given a prostate examination before.

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I didn’t complain – it was the only time I had enjoyed a finger up my ass, as well as being sucked off by one of the most competent cock suckers I had ever enjoyed.
After I had cum at least four times I decided it was time for me to give her some of the pleasure I had enjoyed in the way a girl enjoys it.
Then it happened. She was extremely reluctant to remove the bottom of her attire – was she playing hard to get or was she trying to avoid intercourse and me fucking her. I was getting a bit frustrated at not being able to get to her cunt. Then something I wasn’t expecting – she hugged me and began to cry. I couldn’t work it out – why when she was enjoying everything she was doing to me but resisting me giving her similar pleasure. I had performed a lot of vaginal and oral sex and I believed most of the women I had slept with had enjoyed the experience. Then it happened – she relaxed and I slipped the dress down and her pants in the same motion and I was completely shocked – she wasn’t a woman at all but had male sex organs – I had been seducing a she-male. She had a beautiful hard circumcised cock standing out from her manicured pubic patch.
I admit I was stunned – she was now naked and she hugged me and pleaded with me not to hit her ( I will continue to refer to her as a female).

It was only then I realised she had an Adams Apple. She would do anything I asked but please don’t hit her or throw her out. She would talk to me and if I wanted to I could use her sexually for anything I wanted. Well I took a few minutes to recover – after all I had been kissing her and her body and nipples – she had given me the best orals ex I have ever had.

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I had been treating her as a woman, but she obviously had been born a man. Then I said well what normally happens now. She lay back on the bed and said I am yours to do whatever you wish or I will do anything you ask. Her cock was still hard and sticking up.
I don’t know why I did it but I leant down and took her cock into my mouth - I had never sucked another cock in my life but I didn’t hesitate – I started to do what she had done for me. I wasn’t disgusted and it felt quite pleasant – different to giving a woman oral sex but all the same I wasn’t revolted by what I was doing. I asked her for directions and she willingly told me how she enjoys having oral sex. I followed her every instruction and actually began to enjoy it myself. My cock was soft now - - I was stimulated sexually but my cock wasn’t. We spent a good 18 or 20 minutes beginning and practicing and engaging in oral sex on her, and followed her every instruction and desire. Even to mssaging her prostate as well with my finger up her bum. There was no odour and it came out as clean as it went in – I was surprised and she told me she always prepared herself for this eventuality – often with another she-male partner. Any how she continued to enjoy what I was doing and to be truthful so was I. Then she said she was almost ready to cum and what did I want to do. I could take her cock out and masturbate her, I could take her semen and spit or the ultimate was accepting her cum and swallow it.

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I chose the latter – I had never done anything like this so why not do the ultimate – she had sucked my cock and swallowed every drop of semen I produced and never gave me any indication it was unpleasant. I thought to myself – there has to a first for everything – I was 28 years of age and had never tasted cum – now I was going to.
She told me exactly when it would happen and gave me the opportunity to change my mind – no way – I was going all the way - and she came with the most amazing oral exclamations – she was really enjoying it which made me feel good and I had a mouth full of her cum. I swallowed the lot and had this strange taste in my mouth – I was quite surprised – it wasn’t the tastiest thing I had ever tasted but it wasn’t as bad as I had imagined. Salty, sour and had the texture of phlegm. I had done it and hadn’t gagged as I had heard many do when they do it the first time. I got off her and she kissed me – and I enjoyed it. We were now both naked and our naked bodies were rubbing against each other and really it was no different to her being a girl other than I could feel her penis.

She described her breast enhancement and I enjoyed suckling on them as much as I had any other girl.
We got into bed and she stayed with me till the early morning and we had sex frequently in the way she-males enjoy sex. I had my first anal experience and actually fucked her anally – It wasn’t as bad as I imagined and apart from having to use a lubricant (she provided) to gain entry to her ass – it was not a lot different to fucking her vaginally. We tried it both doggy and missionary style an I enjoyed it both ways and came into her as I would have vaginally – she used the bathroom after each episode and removed a lot of air etc afterwards. I initially accepted an offer to try anal sex but stopped her when the top of her cock began to penetrate me and it began to hurt like hell when she was entering me – She never got more than the head of her cock into me before I had to stop. I have never had anything bigger than finger go up me there and she had a nicely proportioned 7 inch cock. I had gone beyond my wildest dreams in sucking a cock and swallowing cum.

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Having anal sex was not for me, even by a very attractive she-male.
She left me just before dawn and I called a cab for her. We kissed as she left and when I closed the door ---- I asked myself why did I do it – if anybody had asked me if I had ever had an experience with a she-male or told me of their experience I would have been isgusted I thought – but I had just done it and enjoyed it. I could still taste her cum – as I had sucked her off two or three times – she asked for it and I obliged her, without hesitation. I could not believe that I could say her cock looked beautiful – but under the circumstances it was. I have never been close to or held another guys cock but with hers I was enjoying the sensations I would had it been a vagina. Both in my hand and in my mouth it felt awesome. She never hesitated and initiated oral sex on me without being asked and performed it like I had never experienced before – obviously she had lots of practice.
One thing I was happy about – I had not completely achieved anal sex with her – that was just too painful for me and had it not been - I guess I would have allowed her to cum in my ass – and that is the only thing I was happy we didn’t achieve. She appreciated the times I achieved it with her and showed me how appreciative she was when I completed that with her.
When I think back on what I did – I can only say it was her beauty that I did what I did with her. Sex does some funny things to you and I could not imagine myself doing that with another guy – under any circumstances – but I did it with her.
Would I do it again – with her – yes - but not with anybody else probably, and I certainly would not suck another guys cock willingly. The chance of our paths crossing again would be almost impossible but I cannot honestly say I didn’t enjoy it – but I wont be looking at males to recreate the situation again – it was only going to be a one off.
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