Losing My Virginity: Pt.1

I believe I’ve told you about losing my man-cherry before. It was with a tall, skinny, boss-eyed twink in my local cemetery. All quite a shock for me really as up until that point I’d imagined it would happen on a beach with Tom Selleck and Burt Reynolds taking turns, and with Sean Connery playing with my nipples. (Never let it be said that I don’t go for a certain type). Anyway, the real event was a bit crap and unmemorable really, so often I try to pretend it didn’t happen, and that the first time my hoop was bludgeoned was some years later by a 6 foot hairy sailor in a deserted house, his rough, weathered hands pawing at me, as he had his way with me time and time again pushed up against the wall or on the bare floor boards. I went home with some odd bruises that night, I can tell you. Ah, good times…


Sigh.


Sorry, where was I....

Ah yes, what I want to tell you about is how I lost my virginity - WITH A GIRL! Shock, horror etc. Yes, for once upon a time I did indeed have a go at poking my pork sword up a girl’s squish mitten. And here's is how it happened…

(cue wobbly memory effect)

It was back in 1992. Saturday January 11th to be precise. I know because it was my friend's 21st birthday on the 8th and she threw a small party at her house the following Saturday. For the purposes of this story we'll call her "M", and just for the record I was also 21 years old.

The intended guests had received invites in the post some weeks before. It was to be a Murder Mystery evening, and everyone had a particular character assigned to them who they had to dress as and stay in character as for the duration of the evening. In her infinite wisdom "M" had decided that all intended invitees would be cross-dressing, and when I opened my invitation I found I was to be a fading Hollywood star, once a great actress but now pushed aside by younger upstarts. A Norma Desmond figure, if you will. I wonder why she picked me for this glamorous role...

In the intervening weeks I found all the items I needed, and on the afternoon of the party I collected my outfit and drove to "M"'s house where a team of girls were going to transform me. You know what girls are like when they get a sniff of being able to put make-up on a man.
Come 7pm and everyone was arriving. The girls were in a variety of male costumes. There was a farmer in wellies and on a toy tractor, a businessman in a suit and tie, a fisherman in waders and sowesta (with a fake hairy chest underneath), and assorted others. The men were all dressed as women; an old Miss Marple-style grandma, a power-dressed businesswoman, a harassed mother of three (complete with pram and "babies"), and various others.

And there was me; blue sequinned fishtail halter-neck gown (part of a Diana Ross costume I found in a fancy dress shop), big blond curly wig, 6-inch heels (courtesy of a friend's Mum who had big feet), suspenders and fishnet stockings, long, red (fake) nails, plenty of fake diamonds, and a face full of slap courtesy of my make-up team. The only thing I didn't do was shave my chest or legs - some things are sacrosanct! I waited until everyone had arrived and made a typically grand entrance down the stairs with a glass of champagne and a cigarette holder, darling.

So, for the entire evening we had to stay resolutely in character. We'd been given certain things to say, and "M", as the game's leader, had to reveal certain vital pieces of information. At some point someone guessed who the murderer was (I think), but the evening was about getting spectacularly drunk. We succeeded.

We'd all decided to stay at "M"'s house, so we'd all bought sleeping bag and changes of clothes. At some point a grand decision was made for us all to go to bed, so the sleeping bags were rolled out over sofas and floor, and people started getting ready for bed. Or in many cases - mine included - we simply collapsed as we were.

I'd drifted into the fitful sleep of the pissed, only to be woken by one of the girls. I should add that at this time I wasn't generally out to this group of friends - only three people present knew I was gay. Anyway, my sleeping bag was unzipped and in climbed a girl. The one dressed as the fisherman. With the fake chest hair, remember. We'll call her "H". I was still fully dragged-up, barring the wig and heels.

"H": Do you mind me coming in with you? My bag's not very comfortable.

OMO: Erm... no. I guess not. Gonna be tight in here with two though.

"H": That's ok. I don't mind being pressed up against you.

OMO: Er... erm... oh.


(To Be Continued...)