why is it all so complicated?
lost mine very late (much older than 20), after a couple of near misses at uni. Eventually met someone off the Internet and after a few weeks of enjoyable playing lost it to on the sofa. It was so good I went numb. Also went soft from nerves when inside her.

First penetrative sex with coming was with another woman. I couldnt feel much, and there wasnt even an orgasm. I've still not had satisfactory penetrative sex, although BDSM, hand jobs, tit fucking and good foreplay rock. It's the journey, not the destination that's important (I'm larger than average, have had my technique approved of and arent senseless down there, it's a pity it's not doing much for me yet).

Lost my bi V plates to a bloke I already knew from a club. Ended up going back to his and having a mostly great time - he made me feel so hot doing a couple of things.

Did it all sober, which seems remarkable in comparison with everyone else.

sod waiting for true love - being a virgin as you get older is horrific. Lose it to someone you like that wont bolt straight afterwards, as more experience is expected from older peeps..

I envy people that seem to manage 'I'm a man, you're a woman, we like each other, let's shag' because it's never that simple for me :(
(EssY, Tue 8 Mar 2005, 13:22, Reply)

viriginity
nice and boring really, no blood or anything. but i am guaranteed to go to hell now, as she was a good muslim girl (not anymore!).
(throbbo, Tue 8 Mar 2005, 12:26, Reply)

It lasted
as long as this post.
([sic] You're ad here?, Tue 8 Mar 2005, 12:15, Reply)

it's so boring I can't even be bothered
got drunk

fumbled around

woke up

err ugly bird in my bed
( darth munki is flipping livid, Tue 8 Mar 2005, 12:00, Reply)

it was ace
i was 17, my sis gave me a condom as a joke, it was 2 years past it's sell by date. anyway i told my girlfriend the story, and she just told me she wanted me, 5 mins later i had lost it.

and it was good.
(Nemo, Tue 8 Mar 2005, 11:48, Reply)

1993
i was 13 or 14, after lots of alcohol and some mildly strong lsd, in the back alley behind a club called xanadu while on family holiday to cyprus.

oooh, must have lasted all of 30 seconds. in my drugged up state i was more enamoured with the deep amazing colours of a nearby swimming pool. dont even remember the girls name or what she looked like. infact, i'm not even 100 percent the event actually took place.

but if it did, it was well over a year before i put my cock into another ladies part again.

*insert joke about length/girth here*
(Mildred is a slimy, double-crossing, no-good swindler, Tue 8 Mar 2005, 11:25, Reply)

Not Me, but a legend I met at uni.
So... My friend, lets call him Paul as that is his name, young age of 16, just picked up his GCSE results (and was very pleased with himself). Goes home to his Mum to tell her the good news and as she is so proud of him slips him a sly £100.

At the sly age of 16, V plates in hand Paul heads to town to the red light district and uses his mums money to break himself in with a prostitute.

Appologies for length (had to add that as FIRST POST).
(Robble, Tue 8 Mar 2005, 10:53, Reply)

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)

Took a dive
17. Senior in High School. Talked to my squeeze early in the evening. Said she had to babysit and wouldn't I like to come over around 8?

Told my folks I was going to a friends' house to do homework.

Her folks knew my truck. I was to park down the cul de sac and scamper along the back fence to house number 3 and come in through the back door.

Dark as the inside of a cow's stomach that night. I scrambled up and over the fence. I SAW the goddam swimming pool. Hopping down I proceeded to put one foot on terra firma, and the other into the pool; the rest of me followed that foot right quickly into the un-briny deep.

She heard the commotion and almost pissed herself laughing. Got me out of my wet clothes. Them into the drier, and me into her. Fair 'nuff.
(shamblinthru Grasshopper! Next time use the potholders!, Tue 8 Mar 2005, 5:48, Reply)

i don't know.
i don't know when i lost my virginity because i was never sure what counted. could have been in edinburgh after a shady afternoon by the train tracks heavy petting in the woods (look i've seen worse, someone taking a dump in cowgate at 6am) and then back to his house for something heavier but i'm not sure it went in (says a lot really), and then his mum came home anyway so we got dressed and pretended nothing had happened, ha ha

definitely had sex about a year later in my then boyfriends bedroom (different boyfriend), was really quite dull. and it hurt. i must have been about 19.
(corruptia, Tue 8 Mar 2005, 5:30, Reply)

it was satisfying
I was 16, she was 17. She was acting the lead role (a teenage, suburban prostitute reflects on her life) in my final project for my television production class. after my crew left for the day, i had her do some voice overs and watch the editing. we got bored and went to make out. she proceeded to go all the way, and i wouldn't stop her. needless to say, my mom came home right in the middle. We finished up quietly, and then mom made us both dinner.
(Baron von Aaron CHARGE!, Tue 8 Mar 2005, 3:05, Reply)

I was at school,
she was a SEN (trainee nurse)
She forbade me from coming to see her after school in school uniform, so I had to change. (To be fair, she did pick me up from school occasionally wearing her uniform, (which was major kudos))
The first afternoon we did it for real, she insisted to wear her heel shoes (but not uniform, unfortunately), and gouged holes in the walls of the nurses' accomodation. (Not me, I must admit, but uncle Rabbit).
Then the fire alarms go off, as they do with monotonous regularity in hospitals, and I have to hang around in the hallway of the nurses' home with various boyfriends, partners, pimps, and visitors; until she is happy that her patients aren't toast. Then we get back to the main event, which is, by now, like trying to put on a wet glove.
So. all in all, not a good start.
(etchi, Tue 8 Mar 2005, 1:18, Reply)

Third time lucky (older women rock(
1st near encounter: was at legal age, but had no protection. Therefore, did most things but not “the deed” as it were. Decided to lie through my teeth about doing it which really f*ck*d with my head later on, gave me deep psychological scars and I was mentally beating myself up about it while my friends lost theirs and I lived an enormous lie about getting some. Thinking such warped things such as “What if I never get any AT ALL? EVER?” and “What if I get killed tomorrow and die a v*rg*n??”

2nd near encounter: was with a friends-girlfriends-best-mate. Agonisingly close to “doing it”, but denied. She decided to go back to her ex, and dumb ass me couldn’t get over it basically, which caused and epic fall out with a certain crew. Which, to this day, I still don’t speak to

3rd proper encounter: started a friendship with the receptionist at work, who was over at the Newcastle branch of where I work. After a years worth or randomly chatting sh*t via email (as many as 50 in its heyday), numbers were swapped etc only a couple of months after seeing her at a Christmas work party. Liked what I saw, cracking tits, mid 30s, divorced, and not the evil trout faced munter I’d imagined (think about it, I was taking a hell of a liability randomly chatting crap to someone I’d never seen before)/

Anyhow, it resulted in me spending a weekend there (it was actually Valentine’s day week) over at her house. Got all my favourite food, favourite beers etc, and I seriously though that I’d never get my wicked way with her (despite sending smutty emails via work email account and explicit text messages). The first night I was there, late at night, she decides to cosy up to me on the couch while I was being all sheepish and shy, struggling to conceal a major “tent pitching” issue while watching a film with her. Frustration gets the better of us and she drags me upstairs and what we didn’t do wasn’t worth writing on a post it about. We slept little and were at it like rabbits. She has no idea she was the first woman, and never will.

Cracking way to get first shag though, out of town, enjoying the sights and scenery of the area, the pubs, and her obviously. Acting as a different person than plain old me, leaving it all behind, my cherry included. Like a f*ck*ng fairytale with a happy ending. F*ck*ng classical, man…

The best things come to those who wait, all those out there with “V” plates still intact….Have hope!
(Panteneman Isn't entirely sure why he bothered on, Mon 7 Mar 2005, 23:21, Reply)

No great anecdote on the performance, however...
I remember a voice in my head continiously whispering: "Oh my fucking God...oh my fucking God...this is actually happening.. don't fuck it up..." While I remained as quiet as Anne Frank.

The only other real memory I have of the event was, and I don't wish to be graphic, but - it was the MOST I ever physically ejaculated.

You see, being a sensetive guy, I went for the spectacular porno money shot on her lovely young tits. However instead of the usual teaspoon or so of man love, I produced what appeared to be a full litre of 'baby gravy'.

Shocked by this loveless emission sullying her physical perfection and the shattered attempted tenderness of physical love, she was silenced with horror -as was I -in bemusement of how I produced so much sex liquid when at the time I was bashing the bishop at least three times a day.

So, yes, there she was covered from waist to face in sexual effluvient waiting for me to do something or say something. So, I carefully leant over to her bedroom radiator and selected a towel to wipe this runny sex debris away. I pawed at a dark red towel - she shook her head, then I reached for the white one - she nodded and I wiped her down.

We went to sleep and in the morning I was free. We never saw again, but I thank girls like that for us turning boys into the supercharged sex professors we are today.

All hail lovely girls with sweet smelling wipe-clean skin.
( Your Mum, Mon 7 Mar 2005, 22:28, Reply)

hmm,
twas the early summer of '04,(i was 15 at the time) on a sunday i do so remember, (Apparently bad luck, seems true)and after what had become customary foreplay the previous 2 months, it happened.. and i will say the scream the blood and the inability for her to walk will be remembered for years to come..whats even better was the fact A) 2 weeks before she dumped me for my mate and B) she had a drama performance in a church in front of her parents, and had to explain why she couldnt walk.. class.. untill she slept with another mate of mine... 8 months on, revenge is nearly due.. im sending her what she left here ;)
( [DTMX] Fishing hook, Mon 7 Mar 2005, 22:15, Reply)

One of several.
It was one of several failed attempts to do the deed. Alcohol was my nemesis in those days ...

I was on holiday with several of the lads in Tenerife I believe at the tender age of only just 17. In the apartment above our were a group of 20 year old Mancunian lasses. Balcony flirting ensued and before we knew it we were in their apartment trying to look cool and probably failing miserably.

A pint of mixed spirits was passed around, including vodka, tequila and whisky. The idea was that maximum kudos and cool would be awarded to whosoever drank the foul brew. Unfortunately my inexperienced and malformed pride dictated that I would be the one!

After downing the aformentioned devils piss, one of the girls took a shine to me. I remember her skintight supergirl dress to this day.

She took me to one of the bedrooms in the apartment and whispered sexily to me "C'mon then love lets get down to it. Oh, and we're going out drinking afterwards so lets make it good eh?"

After some inexperienced fumbling involving easily four fingers (FOUR!) the sticky deed was fast approaching. I slipped on a condom and then .... the sickly brew of potent alcoholic spirits went straight to my cock who decided that now was a good time to do an impression of an understuffed chipolata.

At this point I recall stomping off to the bathroom and staring blearily at myself in the mirror. I pointed to my deflated appendage and exlaimed loudly "Come on you utter bastard! This is it!".

Unfortunately for me, the lazy worm had decided to sleep it off and didn't as much as twitch. It was crunch time.

I stomped back out of the bathroom and so as not to admit defeat started to go down on the now impatiently rampant Manc-whore.

Unfortunately approximately 3 minutes into this, another part of my body started to rebel against the surfeit of alcohol in my blood stream. This part was my stomach, which started to churn wildly.

As an upshot of this I sat bolt upright and (god knows why) exclaimed "Please may I go to the toilet!?".

Not waiting to hear a response, I dashed off and forgetting to either shut or lock the toilet door began to loudly vomit into the toilet bowl.

Little did I know that the evil whore had grabbed a video camera and was busy capturing close ups of my spasming arsehole as I was wretchedly vomiting.

I woke up the next day, naked in the apartment hallway to the spitefully gleeful cackling of my so-called friends (who had just been treated to a premiere of last nights filming) and a stinking hangover from hell.

The last I heard of it was that the footage was being shown around Manchester by the evil bitch whore as an example of the worst (near) shag experience she had ever had.

Meh.
( squirrels emit silent screams has updog, Mon 7 Mar 2005, 22:15, Reply)

It
was with Melanie Stark, she had pink knickers on....... 1986
(codename Gaz, Mon 7 Mar 2005, 21:00, Reply)

take a seat..............
my innocence was lost way back. A first attempt was ruined by my mate bursting in when a game of ‘postman’s knock’ got a bit lairy and I was about to pump some meat. So later on, I was going out with this girl and my mate had a Christmas party round his. Being the suave bloke I am, I offered he upstairs. She said ok, which was a miracle, into the spare room we went. Anyhoo, after feeding the pony and checking the mic for a while, I suggested we try a new game of bury the trumpet. The reply was positive, so out came the jonny I’d had in my wallet for 6 months, and on it went. Squelch, fart, rumble, awkward, bing, bang, wallop, the deed was done. Unfortunately Mr jonny had decided he’d had enough and disappeared during the main event. He was in the bed sheets, so we told him off and flushed him away.
A few months later of keeping my mouth shut came to ruins when matey told me he’d just nobbed his bird for the first time. I couldn’t hold back, told him the whole story and how I’d kept quiet. He wasn’t impressed as he shared the bed with his missus that night and thought it felt a bit damp, but put it down to the window being open.
( robbydogg - shabba best before end.., Mon 7 Mar 2005, 20:13, Reply)

BITCH!
Nicky was 13 as was I, we were virgins, i didn't want to be, she did.

Two years later, still together, still virgins, big row, she said she loved me, i called her frigid.

She got drunk on cider and shagged Les Short on the playing fields, then felt guilty and shagged me the next day, i found out the day after and punched both of them in the mouth.

I'm 26 now, i don't regret the sex or violence, i still hate them both!

(good news is that soon afterwards i got a sympathy shag off Nickys best friend Joanne when she was drunk on cider)
(DumbBeau, Mon 7 Mar 2005, 19:11, Reply)

It's been a while
and I think my virginity may be growing back!
Dammit.
(MrJelly, Mon 7 Mar 2005, 19:01, Reply)

21
I waited for the right woman and short after 21st birthday it happened. It was all romantic, she was a virgin, too, and we had martini and wine and a nice comfy appartment. We got drunk senseless and because of lack of experience I had no idea being drunk can affect you know what. But I really wanted it and we managed to just fine. Then she went to vomit a bit. Then we did it again. Then I don't remember much. Then her mother called and I think we did it again afterwards. The next morning her sister returned and they both needed morning after pills because she had a similar adventure.
Yeah, it was all romantic.
( Mr. Bell Division, Mon 7 Mar 2005, 18:27, Reply)

still haven't lost it
i'm 16, and still haven't even had a girlfriend. i've had offers, but turned them down. that makes me feel thick, but there we go.

but i've still got the v-plates.
(notjustahatrack peeling a sausage..., Mon 7 Mar 2005, 17:20, Reply)

Still a virgin at 17,
but i am going to Glastonbury this summer... (see Teviots post below, you fool)
(Graz Da Frog, Mon 7 Mar 2005, 16:17, Reply)

Well,
it was a few weeks before my 16th birthday (i never have been one to be told when or what i can and can't do) had quick, painful but strangely boring sex with my boyfriend of 3 months. It only happened the once, we split (pardon the messy pun) up soon after. One weekend back home visiting my parents 10+ years later, i decided i'd look him up as i was single and seduced him with the express purpose of seeing if he was any better than our first time....




He wasn't.
( Clairebare Back once again with the Ill behaviour, Mon 7 Mar 2005, 15:47, Reply)

Still
got it around here somewhere.

Some day I'll dig it out, dust it off and give it to someone special.
20 and waiting for miss right :p
(Nothing to see, Mon 7 Mar 2005, 15:32, Reply)

Crazy clean girl
Managed to get back to this girl's house who I'd been seeing for a little while. She announces after much heavy petting and near nakedness that she wants to go for a bath. "Aha, go for a bath," I think, imagining dirty, soapy going ons. "No, I need a bath," she says. OK, it's now 3.30am and I'm drinking after a late night the day before. After about half and hour, I fall asleep on her bed. Awake two hours later to find she is still in the bath and has obviously fallen asleep in the tub herself. I knock on the door and hear some frantic splashing about and she emerges two minutes later wrapped in her bath robe, shivvering and muttering weird nonsensical sleepy ramblings about how she was 'doing her best'. Had to wait until the morning for a lame hungover pump in the end. Dammit!
(pastypits, Mon 7 Mar 2005, 14:54, Reply)

Rock On!
Glastonbury festival 1997, I was 19, she was 23. We met after Ocean Colour Scene, drank a box of wine (classy). Watched Radiohead, in each others arms, in the mud. (Still one of my bestest memories). Wandered around the site for a while before being "invited" back to her tent. Cue much stress as I discovered a distinct lack of protection either on my person, or in any of the still-open shops (this was after all 2am...). Saved by some random drunk guy who heard my pleas at one of the shops - he donated his - what a gent...

Proceeded to sh*g, rather uncomfortably in a 2-person tent, before a morning stumble back to my tent for the daily beer. Never saw her again.

Still, if she's out there - thanks Jane

Apologies for length. But she LOVED it...
( The Teviot Moose major 5th., Mon 7 Mar 2005, 14:44, Reply)

to be honest losing my vaginity was funny
i had been seeing the girl *not to be named* for just under a week, slept with her, (her first time to) then dumped her 8days later!

after alot more sex of corse ;)

edit : 15
( Sir T. Skellington, Mon 7 Mar 2005, 14:41, Reply)