I was 8 or 9
On holiday in the Med, some random girl with another family, we were both far too young.
Thereafter didn't try again for another decade.....
It also hurt 2nd time around
PS I'm a bloke....
(pitviper, Thu 3 Mar 2005, 18:22, Reply)

Ahh - I remember it well.
5th May 1985 in Emerson Valley, Milton Keynes. I was 15 and was visiting a school mate who had recently moved up that way. Met his new "bird" and her sister ;). Within two days I was giving it large to the sister in my mates bed :)

Hi Sharon! *waves*
( djrich - Live from Houghton Regis got this thing for Clémence Poésy, Thu 3 Mar 2005, 18:11, Reply)

"its like dinny skipping in the widdle of minter".
I was 17, and he was 20, and I'd met him the week before at a mates house, where he'd told me he was madly in love with her ( my mate that is) and spent all night talking about her. The next day, totally out of the blue he text me when I was on my way to stay with my mom for the holidays,and tells me how much he liked me and how he wanted to see me again. The texts got dirtier and dirtier, then finally, the next week I went to stay with him and decided over dinner that I was going to bang his brains out *wry laugh* ahh,the best laid plans. hours and hours of foreplay and finally, the moment was upon us. (I had neglected to mention the sad fact of my virginity, turns out he didn't even notice) and he reaches for the box of flavoured condoms on what passes for his bedside table. He whips one out without looking at it,shoves it on and goes for it.Without any furthur ado he fumbles about,trying to stick it in me. He finally catches that really painful bit just below my hymen (girls, you know what I'm talking about) and I yell out "OW!What'd you do that for?" he looks a little startled and proceeds with a tad more finesse. It still hurt like bejesus though, but I gritted my teeth and held on. Just as I was getting into it, he got this suprised look on his face and pulled out. He grabbed the empty condom wrapper and squinted to see what flavour it was. "ow" he says "oh,jesus,ow." I sat up, trying to understand what the holy jimbob was going on, when he screamed like a girl and ran from the room. I heard sounds from the shower, and his pathetic whimpering noises "oh my cock,oh god it hurts,oh god owwwwwww!". I picked up the condom wrapper. "mint", it reads, then beneath "new improved flavour,extra strong,for her enjoyment" then it clicks.
Retard put the bastard thing on inside out.


Needless to say we didn't get much further that night,as a result I was petrified of sex and of hurting him without being aware of it. Again, it doesn't take a lot of imagination to figure out that everything went downhill from there and we would have done each other a favour if we'd never spoken again.
However,here I am, nearly a year on, and fully recovered I'm glad to say. However, I recently lost my brown wings, and I must say it hurt worse than anything I ever imagined and the guy i did it with was totally sly about it. We were doggying and he slipped out of me mid thrust, then slipped back in-but into the wrong hole- "totally by accident" he says "i didn't even realise I'd done it!" "i thought you were whimpering with pleasure!" Yeah, whatever bumgay, go tell it to the other rent boys.

Apologise for girth? Why? I didn't get a freaking apology!
(Skarlett_nailz, Thu 3 Mar 2005, 18:01, Reply)

There were fireworks...
Literally. Most of the story isn't particularly exceptional, we were both 16, been seeing each other for a couple of weeks or so, did the deed in the living room one night when my parents and brother were out. However, almost immediately afterwards, while still glowing, grinning and cuddling (as you do) we heard some bangs from outside... I pull the curtains slightly open and peer out to discover that a fairly large and spectacular fireworks display was starting up somewhere in the neighbourhood. Watching that together was a rather nice finishing touch :-) Never did find out what the fireworks were actually for, so I can still pretend they were purely to mark the occasion...

Somewhat related, and kind of funny, were my visitations around this time from the condom fairy. Shortly after starting to see my first girlfriend I was surprised to find that a 3-pack of condoms had mysteriously appeared in one of the drawers in my bedroom. The condom fairy wasn't finished there though, a week or two later, having noticed that I'd taken the first three, the fairy returned, and having decided that it had underestimated my appetites left me a 12-pack to replace it... :-)
(Dr Hotdog is considering getting shot in t'eyes with lasers, Thu 3 Mar 2005, 17:48, Reply)

20 years, no more than 3 months ago....
...somehow I just never had a girlfriend upto my current one. It was after a mate's birthday party, and she had gone out with people from her jujitsu society.

The missus is bi, so one of her best mates (who's from Finland, and named after a russian space station) decided it would be funny to 'tease' her. She became all flustered and begged me to come and join her in her Uni halls of residence.

We left our respective parties and went back to hers. I had been harping on to her how I want the first time to be perfect, and came up with a checklist as such. Trust me, there are some SAS missions that are less well planned than this. Everything had to be perfect, and sure enough it was.....

...up until the floor above set their carpet on fire, and we had to evacuate, wearing nothing more than tshirt, boxers, shoes and a johnny.
(rhyswynne - on every social network mullarkey known to man, Thu 3 Mar 2005, 17:43, Reply)

Erm...
So, we were on this school trip (I was about 15 at the time (two weeks ago)), and my hotel roommates and I had accepted "Insane In The Brain" by Cypress Hill as our theme music for the trip. Now, everyone on this ship of fools was coupling up, so my mates and I tried to find an ideal candidate for a little weeklong fling for me. We arrived at a decision that there was this one "bird" that would be more or less ideal. We stayed up most of the night, alternating between pouring water on the iron and making obcene sexual references/ bad-mouthing ex-girlfriends. They all said "Dean, you've got to tap that or I (we?) will." to which I replied some variant of "yeah". About a minute later (download "Insane In The Brain" for the full effect) I said "don't worry, I'll get insane in her membrane".
...
I never did.
The best part? This conversation was had at about 2AM on Valentines Day. In Dublin. We're from Los Angeles originally, so you get a rough idea of how weird it was.
And I never did lose my virginity, to this very day.
(Digitdean: Disappointing Fans Since 1989!, Thu 3 Mar 2005, 17:40, Reply)

very boring I'm afraid
Parents out shopping: check
Condom availability: check
Paranoid listening for return of parents: check
lack of foreplay: check
pain: check
excruciatingly shy & dim boyfriend: check
profound disappointment after the deed: check

damn you Just17!
and thank you university...
( Hidden Mouse, Sleeping Kitten Gromada? Gromada!, Thu 3 Mar 2005, 17:29, Reply)

sheep
nuff said.
(farmer, Thu 3 Mar 2005, 17:29, Reply)

24 hours sleep deprivation.
Sleepover at mine, everyone fails to show but one girl. Around 4am, she kissed me...then went to sleep feeling guilty about cheating on her boyfriend.

Six hours later, after having no sleep after the ensuing "wtf" and playing Doom 3 in the dark, I bought her a cup of coffee to wake her up. She never did drink that coffee.

About four days later, she got off with twelve people at a concert. I guess the rumours about her being a slut are true.

Her (now ex-)boyfriend's still after me.
( Reid got it going on like Donkey Kong, Thu 3 Mar 2005, 17:26, Reply)

Greenbat
Someone told me about that. Eww.

I lost my virginity to a girl (I'm female) when I was 12 or 13. Does that count?

I also remember the first time I ever gave a guy a blowjob and his best mate walked in and said 'Do you want a cup?'
(WaffleMonster, Thu 3 Mar 2005, 17:25, Reply)

Breaking the banjo.
I got the big come on from a nurse in my local one night. I was a late starter - about 21 - and she was as rough as a badgers arse. And ginger. It must have been the uniform......

God knows why, but I agreed to go out for a drink the next night. All went well, until it came to drop off time outside her parents house. She started massaging my neck, and after some fumbling it became clear that:
1) She wasn't wearing a bra under the baggy jumper, and
2) She did indeed have fantastically enormous lils.

After some frottage of the close encounter style, I suggested we go somewhere a bit more private than her parents driveway, and ended up in an apple orchard shagging in my Ford Orion. Needless to say it wasn't the most romantic or comfortable of settings, and before long biscuits were blown.

The next night she took me out for a drink, and when she dropped me off at my parents, she came in for a nightcap.

Parents upstairs, me kneeling in front of the sofa and banging her arse off. When all was said and done and pull out time came, I realised there was a lot of blood, and that my foreskin was the wrong side of my helmet! Talk about shocked! Once things had settled down (read soft) I managed to pop everything back into place, but the banjo had been split - so no more banjo playing for a couple of weeks.

What I didn't realise was that in my panicked state, I'd bled all over the rug. I had to throw it out and lie that I'd had a nosebleed.

It lasted 5 months in all. The end came when her mum made her stay in and knit rabbits for an Easter Fayre rather than come out with me, and she put up with it! She ended up marrying a mate of mine - but that didn't last long either.

No apologies for girth. You love it really. Just be gentle when playing the banjo.
(Hog UK, Thu 3 Mar 2005, 17:24, Reply)

Does it count if I lost my anal virginity to the talk board?

( ArthurTheRat, Thu 3 Mar 2005, 17:23, Reply)

gettin some pussy
19 years old, desperate, in the bedroom of the girl Id fancied since i was 6. So result in a way. Except she had taken to smoking 20 a day so her fannybatter tasted of marlboro. Still had enormous, stupendous tits, which I was very happy to see. Until she used the phrase "Christ, were you bottle fed?" which gave me the hint to move on.
No condoms so bareback and morning after pill....and clap as it turned out.
Oh and the title? because throughout the deed her semi feral cat was clinging to my thigh and biting my arse, and I didnt want to stop to remove it.
(littlebootshorse, Thu 3 Mar 2005, 17:11, Reply)

Planning is everything
Me and my mates from college had a competition to see who would be last to pop their cherry. Mate Stu got in there early doors and the pressure was on. I planned it with military precision so it would occur when my folks and brothers were out. Robbed a condom up from parents room, bottle of wine in. Perfect. Made sure i did with Napalm Death on the stereo just so i could say i lost it to Napalm Death (i'm still proud)
Both got the giggles but still lots of fun. I feel sorry for all you folk who had a crap time. You've just got to think about these things. Oh, and to all the girls who proclaimed
they lost it to a toothbrush or fishfingers or some such. Did your hymen break? No? Still a virgin then.
(Man Worm, Thu 3 Mar 2005, 17:03, Reply)

Seduced by an older woman
First year at uni... (yes I know it's rather late, but going to an all-boys school till the age of 18 meant minimal contact with females other than Mrs Musk, the 60 year-old history teacher with the damaged, wobbly face, who nonetheless was able to generate instantaneous boners among the classroom just by walking in).

Anyway, rather drunk from my 19th birthday night out, this 26 year-old Greek PhD student invites me to her room. Gigantic tits that were marred only by the film of fluff that was spread across them. But basically I was rather excited at the whole prospect.

Cue lots of kissing & fondling (something which I had learned to master over the previous 5 months) for about half an hour. Then the inevitable happened and nakedness occurred. "Don't do anything to betray your complete lack of knowledge, experience, skill and co-ordination", I thought to myself.

With this in mind, I confidently straddled her and simply expected my cock to slide in without a problem. Clearly it wasn't that easy. So I called upon the power of my right hand to carefully place aforementioned cock into the hairy greek old muff.

Me: "I think I might be too big for you"

Her: "no, it's lower than that"

Me: "oh"

*moves lower down, finds what appears to be the grand entrance, pushes for glory*

Her: "ow... no, lower than that"

Me: "fuck that really hurts"

It seems the feeling of pain corresponds directly to the bright red area of my foreskin, and I go to the bathroom to panic in private.

When I get back generally unscathed she's basically twanging the crap out of her banjo and pretty much forces me in to the correct hole. I was a bit disturbed that she was still frigging away while I was thrusting but it meant that she came rather quickly. Although it was as clear as day that I was NOT the cause of her orgasm, I still felt like a champion Shabba Ranks-style lover.

We hardly spoke to each other again after that.
(soma9766, Thu 3 Mar 2005, 17:01, Reply)

Lizzilla
That about covers it. Cleo's, Wimpy a shag in the cold.

I slept on the quay too.

This doesn't count, but I once went to bed with one of my sister's friends (a good source of flange when you're young) who was a virgin and maintained that she wanted to remain so.

Buggering a virgin is something that, even as an old married father, I remain proud of.
( Lord Manley of Ven www.justgiving.com/manley - please?, Thu 3 Mar 2005, 16:57, Reply)

no references to people or ages
but things had been building up (so to speak) for the week before the event. "Things" had been done the night before, I'd stayed at hers, and when we woke up on the Saturday morning it all went like in the movies.
Autumn sun streaming through the window, etc etc.
When we'd finished, we did it again just to make sure I'd done it right.
And then again later in the evening.
Typical - you wait for ages and then three come along at once...
( Gizmo.mp3 does not exist, Thu 3 Mar 2005, 16:53, Reply)

aged 14 in love with a guy same age
we were both 'learning' off each other and in the deep passionate kind of love you only get when you are 14
of course being fourteen, no booze or flat to go back to.... we had Worthing pier. Every weekend for about four months we went down there for a grope as you do, no complains there! then we decided we should do it.
lets set the scene: its christmas eve, on a stoney beach. christmas shoppers over the road at always at risk from townies coming under the seaweed covered pier for a smoke (learnt from the past)
so anyway, christmas eve. freezing. basically we failed, we had problem of 'keeping it in'. *cough* no one tells you about these kinds of things!
we gave up and did try again untill mothers day. 10th march 2002 (ooooh anniversary soon). my mum and brother had gone to see Monsters Inc so i called him up to see if he wanted to play on the playstation. i realised then we could get it on. and we did. it was rather special... then he signed and dated a bit of paper. i was soooo offened.
even more so when he dumped me two weeks later when we had been togther nine months.
what i have learnt: piers are not classy, don't give it up too early, cold does not help, practise makes perfect
(fluffytail, Thu 3 Mar 2005, 16:50, Reply)

A mate new a girl
who used a glass test tube. Unfortunatley her mum came in, and said girl shut her legs to hide it. The tube broke.
Rachy: could you give us an email (in profile)? I'm wondering who on earth you are. Thanks.
( Greenbat, Thu 3 Mar 2005, 16:44, Reply)

eeh by gum lass
On holiday at me gran's I ended up with the local farmer's boy, in the cow field behind t'pub, a bit tipsy from 5 pints of guiness.

he said he'd loved me since the first time he'd met me (when i was 12 and he was 19 - sicko) but i wasnt listening, i just wanted the jilly cooper experience... rampant cocks, squeals of pleasure, flesh pounding, grass in your hair...

needless to say i was let down. he was hung like a mule, but about as interesting as one too. shame.
(chesty, Thu 3 Mar 2005, 16:35, Reply)

Lord Manley
Nah, I figured outdoor sex on the building site that is now Bideford quay could be interesting, but if you lost yours after a night at Cleo's I can almost understand what led you to it. God I hate Bideford.
(Lizzilla, Thu 3 Mar 2005, 16:31, Reply)

First time, brown wings and firearms
My old University mate Doug lost his cherry to a girl he had met in his local while his parents were on holiday.

They both were drunk and went back to his folks house where they made the beast with two backs on his parents brand new white leather sofa.

She had been around the block before and said that she liked it up the arse - what she hadn't told him was that she had also come on..

Anyway in the hungover aftermath of him losing his cherry, he found that the expensive soft leather sofa was splattered and stained in cum, shit and blood. He tried his best to clean it - but the damage was done.

When his parents came back from holiday the first thing they saw was the ruined furniture. Doug panicked not knowing how to tell them the truth - so he blamed the dog for shitting on the sofa.

His Father took the dog outside and offed it with his shotgun.
(Catchag "You know!....For Kids!", Thu 3 Mar 2005, 16:29, Reply)

Frenchman ?
When I was 15 my Dad used to have business interests in Europe and he met a few other fathers who had kids of similar age to me. He thought it was a good idea that I did the foreign experience bit and have penfriends. Occasionally these pen friends came to visit. Cue in one very nice 16yo french horny male who was to stay with us for a few days. God he was gorgeous - but I'd never had sex before and sex education in the 70's on the IOW was watching some woman up full frontal having a child. Put me off having kids for ever......anyway I digress......This french lad, I think his name was Pierre or something, had his eye on me and as soon as my parents went to the sailing club we just looked at one another in lust. I didn't tell him I was a virgin and I must have made a good impression because we did what I would consider to be now, VERY good sex - 5 times in the space of about an hour - god - imagine that !! In the bedroom, kitchen, hallway, bathroom ...... boy would I like to do that again ! Woooooo !!!!!!
( Tiggy the diver, Thu 3 Mar 2005, 16:24, Reply)

I lost in it my car at the ridiculous age of 21
(TWENTY-ONE!) to a fat bird whose mate I really fancied. Her mate was banging her boyfriend in the house I was parked by, which was why we were in the car.
I then went on to go out with her for a whole year after, as I had no idea how to break up with someone. The idea petrified me. Plus she was a nympho of epic proportion (I estimate we did it about 3 times a day at least during that year), and so I just counted my blessings.
Oh happy days.
(Just recline and let me service you, Thu 3 Mar 2005, 16:20, Reply)

I think my first time was pretty standard...
We were both virgins. I was 16, he was 17. After arranging the date and time of my de-flowering a few days earlier (not a romantic bone in my 16-year-old self), neither of us really knew how to go about it.

It sounds like the perfect scenario now, in theory. He was too big, i was too small and so two days of bleeding ensued. After we had spent an age trying (him suggesting i impale myself on him - owwww!) we walked to Regents park, watched the sun set as blossom fell around us. He then had a mad dash home to hide some condom wrappers, in case his very religious mother found them.
(droopy, Thu 3 Mar 2005, 16:20, Reply)

I was in luuurve!
It was spring. The birds were singing. The sap was rising, as was my 16 year old libido. I smuggled him into my house under cover of darkness in a tumltuous mix of romance and lust.

It were crap.
( Miss Behave - Delicate little flower, Thu 3 Mar 2005, 16:14, Reply)

I lost mine on the floor of a mates living room after a house party at the tender age of 17. We thought all was well as there were a load of other pissed people asleep on the sofas and chairs and also on the floor so I was quite happy to bump uglies with the wench I was with.

I discovered 6 years later when everyone turned up to my birthday evening in the local boozer wearing t-shirts proclaiming the fact that everyone had been awake.

I still have not lived it down to this day
(_earwaxuk_, Thu 3 Mar 2005, 15:52, Reply)

Durham prison, 1991.
It's nice - we still stay in touch.
...Well, they all sign a card once a year.
( Zak McFlimby Twibbling @McFlimby, Thu 3 Mar 2005, 15:48, Reply)

Whats that smell?
I knew a girl at school who lost hers to some frozen fish fingers. No joke intended. Skank

EDIT: 2 weeks later one of her sea cadet buddies was so impressed (urgh! and he knew cause everyone knew what a skank she was) she lost it for real. I think she was 13-14. Oh and she showed us horrible close up photos of them tieing tongues, ewww! SKANK!
Thanks to the phonecall to mate who rememebers.
( Blobcat Less Jaffacakes this year, Thu 3 Mar 2005, 15:45, Reply)

17 - First real girlfriend met at college.
Planned to go to a house party at some randoms house. Party went well with lots of booze and chatting. She passed out... My mate (also a virgin at the time) went off and starting banging his girl on the bathroom floor with the rest of us listening in from downstairs.
My girl evetually awoke and dragged me off saying 'its your time'

We had a bedroom, she pushed everything off the bed in a proper movie style and we got down to it. I was scared (first time and all) she was a slag anyway so she knew what to do.
Went ok though, was going for ages, trying to hard couldnt perform properly. We both ended up giving up.
Following morning we tried again and Wooo. All was good :)

Big grin on my face we went downstairs. Everyone else was already up and had heard it all.. Oops. Especcially me shouting 'YES!'when i realised i was no longer a virgin.

We lasted about 2 months, i really liked her but things didnt work out.
Id still talk to her today, only seen her once since we both left college.

Meh..
( [Coo] is one of the Originals.., Thu 3 Mar 2005, 15:20, Reply)