Archive for Strange sexual encounters

The weirdest thing that ever happened to me

I’m not sure this is definitively the weirdest, but it’s up there. I was wondering how I’d define my weirdest experiences if someone asked, and it struck me that some of the things that might seem weird from the outside (a 300-person orgy in a crumbling central-London mansion for example) actually don’t feel that weird at all. But Ah-um-ah-Andy definitely still rates.

I met him early in my TG days, when he politely, nervously complimented my boots and asked if he might rub my feet.

Me: Yeh, probably, wait… J, can this man rub my feet?

Equally eloquent, J said something along the lines of “Yeh, why not,” and my new foot fetishist friend hoisted me up onto a huge speaker. I was dressed in a style befitting the location: skirt with no sides, pinstriped waistcoat, and platform boots comprising more buckles than leather. I set about removing these beauties without flashing too much muff, and belatedly realized I was also wearing Sleepytime Pooh Bear ankle socks.

I whipped them off hoping to belie my noob status, and hid them in my boots. The guy probably didn’t care anyway, and set about giving me a (mediocre) massage. He didn’t seem particularly comfortable making small talk, and when I asked him his name he paused then came up with “Ah… um…. ah…. Andy.” Nothing too strange about that though* and he was communicative and conscientious when it came to sharing his intent and seeking permission.

After a while he nervously asked me if it was ok if he wanked, and I’ll admit his underdog demeanor contributed to my saying yes. I flicked my eyes over to J, who was hanging out with friends some way off, made some lewd gestures and he nodded his assent. Ah-um-ah-Andy set to it and came fairly quickly. While he was cleaning up (I can’t remember the details – wet wipes, tissues, wipe it on the curtains?) I said, “I’ve never done anything like that before. How was it?”

To which this previously timid, whispering, almost apologetic boy looked at me, shrugged, muttered “You were alright, I s’pose,” and disappeared into the night.

Thanks Ah-um-ah-Andy, you were magical too.

* J and I have never been smart enough to come up with fetish alter egos, but there are plenty of good reasons why people do.


Silence gives consent?

Consent sounds like it’s cut and dried. I say yes or I say no. But contested rape cases, hazily remembered or uncomfortable evenings, or scenes with no safeword point to fuzzier boundaries.

I was discussing this with friends recently, and brought up the following incident. I don’t think I’ve posted it before so here ya go:

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Cybersex redux

Many things to write. Let’s start here because I promised part two a while back.

Last summer (a whole year ago, gosh) I had IM sex. I thought at the time I was chatting with a friend, but she told me later her boyfriend (a stranger to me) had used her laptop without her knowledge. More details here.

When sharing this story I hear an incredulous, oft-repeated question: Was the guy so good at faking it that I really, honestly thought he was my friend?

It’s a reasonable thing to ask, and I’ve wondered it myself. I had no doubt at the time and no reason to think a stranger would be lying to me – I was sure it was my friend. It was only when she told me, horrified and upset, what her boyfriend had done that I started remembering things that didn’t add up. The idea of an impostor slowly seemed to fit.

Then my friend moved abroad, leaving the nefarious boyfriend behind thousands of miles of ocean.

The filthy messages didn’t stop.

I think the realisation came with a flash and a crackle. Lies had been told but only when an ostensibly straight, ostensibly religious young lady woke up with a hangover, felt embarrassed or ashamed and made something up to assuage herself.

All the pieces I’d been trying to poke into place slid together seamlessly. The new messages read exactly the same as the first ones, at a time when the girl was alone in a new city. They were surprisingly explicit each time, which is maybe why she lied in the first place and why I accepted her lie – there was certainly an element to the language she didn’t use in person.

Needless to say, I’m over that shit. I asked her not to message me about sex any more. She ignored me. I told her next time she sent those messages I would log out of chat. She ignored me. I logged out. I stuck to my guns and eventually she stopped. *shrugs*

I rarely feel like my boundaries are threatened but this girl, thousands of miles away, managed to do so. I was pleased to find how easily and calmly I could defend them.

Still beating this drum

(And the drum should understand that we’re done when I say we’re done, not before.)

Thinking about sex work from a different point of view: There are women who pay men to fuck them. Probably not many, but certainly some.

There are more sex workers’ stories here.

Daily grind.

About eight months ago I nearly slept with a Thai hooker. It was an interesting experience and de-mystified things a little for me, but it was emotionally negative. I didn’t come out of it feeling particularly good.

About eight days ago I slept with two hookers in New Zealand. And I came out it bouncing off the walls. I was grinning ear-to-ear for days afterward, and wouldn’t hesitate to repeat the experience.

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Pushing back the foreskin of knowledge

Incongruously, I think the title of this post comes from Judy Blume. It’s certainly a quote from a children’s book – I was young enough to be shocked when I read it.

A better title might have been ‘Sleeping with Thai hookers so you don’t have to’ but that wouldn’t have been truthful. The woman took our money and ran long before anyone got laid.

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Paying for sex

A guy I met on Saturday was in the middle of bust-up with his girlfriend because he’d been sleeping with prostitutes.

There are lots of reasons why this could end a relationship – deceit, taking risks with sexual health, psych issues – but once, a million years ago, I was the maligned girlfriend and my problem was that the guy was able to compare me directly with someone likely to be much better at sex.

This tells you a lot about my self-confidence at the time, and my destructive habit of measuring my worth in units of sexual prowess.

But talking about it this weekend, I realised my approach now to competing with prostitutes would be different. Sure, they are gonna be good at sex (I should damned well hope so if they’re doing it for a living!) but would it be the end of the world if they were better than me?

I still credit sex with more mystical influence than it probably has, but the idea of not being the best shag someone has ever had sits ok with me now. Plus sex is more than the sum of its parts, and I have things other than expertise to throw into the mix.

(I am often down on myself for acting in ways that don’t confirm the person I’d like to think I am. Quite a few times lately I have caught myself doing the opposite, being surprised when I realise I have become more rational and level-headed about things that used to upset me.)