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Events leading up to me becoming a transvestite prostitute

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When one of the men who regularly had sex with me suggested I became a transvestite prostitute, I decided to give it a go despite being in my mid 40s.

I was 44 and my ex-wife finally decided to leave me. We had been tolerating each other for years, me having sex mostly with men, and her doing her own thing. It had been on the cards for years, but it still was somewhat of a culture shock as all of a sudden I no longer had to earn large amounts of money to support the married lifestyle we had had. It didn’t really bother me overly much, but in a way I cracked up a bit, as my life was not as full as it had been.

I wasn’t too sure of what to do, so I drifted back into dressing as a woman again. I had mixed feelings about this, and I raised it with my doctor. He suggested I had some counseling, so I had a number of sessions with a nice woman counselor. In the end it wasn’t very helpful, as she help going on about the fact that when I was underage I had been abused by the hundreds of men who had used me. In a way she was right. I had been abused by all those men, but it had been my own choice (apart for the times I got raped of course).

The sessions not being as helpful as they could have been, I decided to just go the route of dressing as a woman a lot of the time. It made me feel more relaxed. I placed a few ads in contact magazines, and began to meet a few guys who were more than happy for me to be in make-up and drag when they used me. Sure, I was in my mid-40s, but I didn’t look too bad as a transvestite – as can be seen from some of the photos attached.

Where I was living was a leafy, middle-class street, and it became a problem sometimes to go in and out of the house in drag. I looked around and found a small shop in Walkden, Manchester. A photo is attached. It had a small flat on top. It was ideal: it didn’t cost very much, and there was a lot more privacy. I was able to set up my business there, and live on top. Not many customers would come in very often, and so I found I was able to live as a woman for most of the time. A friend gave me a dog for security, and he and I got on okay.

I continued advertising in the contact magazines as I had done in the old address. Quite a few men would visit me in my new place and use me. One day, one of my regulars said he was a photographer, and suggested he took photos of me. I was happy to do so, and he took quite a lot of me in drag, naked and, sucking his cock. After a few such sessions, he said that I really should become a transvestite prostitute, as a lot of men would pay to have sex with me. Initially I laughed at the thought, but the idea grew on me and there came a day when I realised that if I became a prostitute then I would get to be used by a lot more men.

So I decided to become a transvestite prostitute, not for the money, but for the increase of men who would have sex with me. Admittedly, there was an ego element there. The thought that I could do it at 45 vastly amused me. I placed an advert with a photo of me, stating that I charged £30 for which they could do whatever they wanted to me. I listed the things they could do. I expected a trickle of replies, but I was totally amazed at the number of men who rang me for sessions.

There were a number of younger transvestites offering their services in the magazine, and I was puzzled why men would choose me over them. Then a friend told me that most of the younger ones placed restrictions on what could or not be done, and I had not placed any restrictions at all, saying that I would suck cocks, get fucked, get pissed-on, used as a toilet, and be beaten with belts or other implements. That was why I was so popular from the start.

In the next chapter, I shall relate some of the sessions in my time working as a transvestite prostitute.


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  • Reply Sammy Joe ID:5c8rcvm9b

    I would pay to fuck you . Looking forward to reading more of your stories .

  • Reply Cracksniffer ID:2dd0x5np8m

    Oh yes, would love to hear more about your sessions. I imagine there were a few rough and violent ones? You look great by the way!