Flashback Friday – Crossdressers in the Cupboard

The youth group I mentioned in last week’s Flashback Friday turned out to be a really fun thing to go along to on a regular basis and though I really didn’t appreciate it at the time, looking back I can see that I had a very good (I won’t say “healthy”) sex life for a sixteen year old. The second residential weekend I went on with them involved once again, a bunch of LGBT young people with hormones flying everywhere staying in an isolated house in the countryside. Sounds like the opening to a really shit and predictable horror film, doesn’t it? It wasn’t.

I think, if I remember rightly, we were there to film an an awareness/coming out/ anti-LGBT-phobia type DVD for the health service but most of the weekend was spent just having fun in that way that teenagers consistently will. On what I assume was the Saturday night we had a drag workshop and so I ended up in a dress and make-up for the first time in my life (but definitely not the last!). There were very few boys there that weekend, I can only think of a few, but one of the others was a painfully flamboyant boy who at the time was called K but has since changed his name to L, so since we already have one story about a K recently we’ll stick with L. We were all a bit over-excited, running around this house, and L and I – whether by design or accident I’m not sure – ended up alone in one of the bedrooms. Against a wall. Ahem. We sensibly decided though that a bedroom anyone could walk into at any time probably wasn’t the safest of places to be at it so we ended up down the corridor in the boiler cupboard. Yep, I’m that classy. (What do you expect from someone whose first sexual encounter was at a church?)

The advantages of wearing dresses and skirts became obvious to me for the first time that night, in that you have almost unimpeded access to everything you need to have access to to have sex without having to actually get undressed in a cold boiler room in the middle of winter.

And wow, I’m all for sexual preferences, but to say that L was a completely submissive bottom bitch doesn’t even begin to sum it up. Had I been more experienced and adventurous I probably could have done just about anything to him and not only would he have accepted it, he’d have gotten off on it. It took a couple of attempts since I’d no idea what the hell I was doing really, and fell out a couple of times, but in the end we got there and I properly fucked someone for the first time. It felt great being on top, dominating, sort of powerful. Because I’m a far cry from being an Alpha-male, it’s a rare occasion I can find someone passive enough for me to completely take advantage of, so I have to enjoy it while I can, and I’m sure that it all stems from this one experience of fucking a boy in a dress in the cupboard.

After I moved to my current city I never really heard from him for a few years, though I got updates on his ever-growing level of campness from a mutual friend who sees him out and about sometimes. I ran into him a few weeks ago in a club on Barman night (I saw a lot of people from years ago that night, it was a bit disconcerting) but we have nothing to talk to one another about so we simply didn’t.

There we go, another tale from the archives. Submissive Sunday coming up, I’ve already had a few stories in and if everyone that has offered to write me a guest post follows through we should have some really interesting stuff coming in the next few weeks!

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  1. #1 by aphRAWdite on April 20, 2012 - 11:55 am

    My fave story so far ;-)

  1. Differences | sexwithdexxx

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