Not sure if this counts.... but(t)...
I’d forgotten I had a photo of this encounter until I read this Question…. So here’s My little story on the matter. (had to make ana account too!! :O)

First-time anal. Drunken-Ibiza-stylee.

A Few years ago (in 1998), I happened to be in the family resort of Ibiza sampling the local goodness, when my friend and I came across a bloke looking slightly lonely in a bar. We enquired of his nationality, and a rather slurred “English” came back. We though he might be drunk enough to be in the mood for buying a beer for us two lovely ladies, so we struck up a damned good conversation. (During which we earned much beer)

During our chat, It became apparent that he’d “accidentally” become separated from his friends, and he was trying to pluck up (Dutch) courage to allow him to embark on his secret mission: To loose his virginity to a man.
Too good to be true: so we egged him on.
To cut a long story short, we gave him tips on how to get a guy interested, and being no strangers to a wee bit of anal, my friend and I gave him tips on that too.
He ended was beginning to get exceedingly drunk when he suggested that we came back to his room: "he had somehing to show us"!!

The lad (who called himself “Waddy”) (strange because he didn’t seem loaded to us)(actually, rather NOT loaded in most ways) then let a rather large cat out of the bag. He said he’d climbed into another room via a balcony to nick some lingerie from a girl. Freak-boy!! (It’s for this reason that I don’t mind posting the pic of him)

I promised to cut it short, so here’s the result. He revealed that under his clothes he was dressed up in this girl’s underwear, and had been so since he swiped it. The photo was taken as he cavorted and pranced around in his very “relaxed” state of drunkenness, and “proving” (as requested) that he actually was wearing it.. and yes, i was nice enough to show him how to adjust it afterwards...



We then returned to the bar with him in tow, found a likely looking boy, and introduced them: totally breaking the ice for him!! We rule!! The rest is history, though he did look little nervous walking off hand in hand with the guy who we could only presume, would penetrate his arse for the first time.

The next day, we saw him and decided that from the way he was moving, he’d been totally successful, and his date had liked teh girly undies: the lad waddled, and looked like he’d had some serious meat “in the seat”. So: Here’s to a drunk and ginger mystery-boy, who lost his gay V-plates to a presumably well-hung guy.

It seems traditional to make a poor pun about length.. and as this is my first post, I’m truly sorry the thing is so long.

I still tell this story to all my friends in the pub: maybe one day it'll get back to him, and he'll remeber not to steal lady's underwear for his own kinky purposes.
(Chocolate and Wine misses her bed, Tue 8 Mar 2005, 10:23, Reply)