Sexuality Part Trois

So after my previous two posts on sexuality, I thought I’d better finish the story here with tales of my failed sexual exploits with transgender people.

The first two were before I met Georgie, so maybe four or five years ago. I’m not proud of this but I joined a particular trans website – and some of the people on there are looking for just one thing, if you know what I mean.

I’d had desires to have sex with someone else transgender for decades and so I decided I really needed to do something about it. I didn’t want to lie on my deathbed thinking: what if? Sound familiar?

So I joined the website, sent a few messages and got to know two girls fairly well, sending messages back and forth for a week or two. I’m not easy!

Back then, I was quite a bit heavier than I am now, so virtually all of my girl clothes were too small, so I went in “bloke mode” while they got into their finery. Boo.

The first was a transvestite who lived about ten miles from me, so I drove to her house. I took a bottle of wine to settle any nerves.

It was clear from the second she opened the door that nothing was going to happen. There was zero sexual attraction on my part.

She was wearing a short black skirt and fishnets, I believe. I forget what top she wore. Her long, blonde wig looked like it came from a pound shop – it was awful. And her makeup matched it.

She worked as a mechanic when in boy mode, and her nails were dirty and broken. Also, the house stank. I had seen a photo before we met, but it was very small and poor quality.

I couldn’t exactly turn round and flee, so we just sat down, chatted while we drank the wine, and then I apologised and left. Disaster. I can’t even remember her name!

Girl 2 was Sammie. Now Sammie was different. When I arrived at her house, she opened the door and looked a million dollars, wearing black lingerie, a beautiful brown wig and perfect makeup. She, too, was a transvestite.

She’s a little older then me, but that was fine. She shushed me as her wife was upstairs asleep, which I thought a little odd – but apparently she knew about Sammie and allowed her to play.

Anyway, my feelings towards Sammie were different – but nothing happened because she wanted to go down the S&M route – we’re literally talking whips and chains here – and I didn’t. I wanted something more vanilla. This was to have been my first time with someone trans after all.

So we chatted and drank wine – again! I offered to please Sammie orally, but she was grumpy because I didn’t want to take part in her bondage plans, and so she refused.

Shame, but the experience was useful for something – I’d always been curious about cocks, as it were – no pleasant way to phrase that! The curiosity had now gone – I would have glady used it had Sammie not refused.

And the third time was after Georgie and I broke up in the summer. This time I was to meet a transsexual – again, I don’t remember her name, but I think this because she used about three.

This was another disaster. According to her profile, she was the same age as me. When I got to her flat and she opened the door, it was clear she was at least 10 years older, if not 15.

This time, slimmer and trimmer, I went in lingerie, with androgynous girl clothes over the top. But again, there was zero sexual attraction, and she’d annoyed me by lying.

And then she talked – for what seemed like hours, while I just sat in a chair listening. She talked about herself the whole time. Didn’t ask a single question about me.

At one point she tripped herself up by saying she’d seen Bowie and bands like Deep Purple in the 1970s.

“I thought you were 42,” (my age then) I asked, bearing in mind I was born in 1973.

“Oh, I am, I am!” The reply.

WHATEVER!

Plus I realised I wasn’t over Georgie either, so was just kidding myself. It was far too early to have sex with anyone, let alone her.

There’s loads more detail to all three stories, but that’s it in a nutshell. So there you have it. Still a trans-virgin.

Will that ever change? I dunno. I no longer feel like I’ve got to do this anymore. And if I meet the cis girl of my dreams, fall madly in love and settle down, it won’t happen.

And I’d much rather do that and live happily ever after than have a bit of kinky sex for an hour.

Andie x