Virgin sexxx
When I was but a young lad my first serious girlfriend and I decided one summer's day that we should both lose our virginity by doing the deed in the local fields. We found a bit of a dip in the middle of one field that was like a lovely sunny nest and divested ourselves of our netherwear.

I would like to think that it was the massive manly girth of my John Thomas which seemed to make it impossible but in retrospect it was more likely because she was a bit nervous and rather dry. For what seemed like hours I manfully attempted to get it in there with no success. So inexperienced (and sore) were we by then that my girlfriend actually asked 'have we done it yet?' The answer to that question came from one of the four blokes standing at the edge of the hollow behind us - 'Fraid not love. Do you want us to show him how?'

That was even more embarrassing than the fact that his alsatian was excitedly sniffing my arse.
(fergus the bogeyman Beware of geeks bearing gifs!, Sat 21 Mar 2015, 12:39, 5 replies)

The night was hot and the air was sticky with sexual congress.
Username Failed Moderation was caught up in the ecstasy of lovemaking.
Without any warning he stopped dead, looked up, and uttered
"I suppose I shouldn't give the satisfaction, but this is the last time I will ever cum on this site."
He withdrew his penis then walked over to the bedside table and grabbed a wet wipe.
He crossed to the toilet and against all advice, flushed the wet wipe away before returning to the room where the sexual intercourse had occurred.
"So long, thanks for the laughs." he said before dropping his guts and leaving the building, forever.
( $$ ✅, Mon 23 Mar 2015, 9:26, 9 replies)

Caravan of Love
Sorry - it’s a bit long…

Like many here, I was unbelievably naive as an adolescent. Easy to laugh about much of it but there's one that still haunts me a little.

In the late 70s I worked in Southampton, after I fled the loveless family home at the opposite end of the country. Why Southampton? Well, firstly it was difficult to get any further away - but more than that they offered accommodation, a godsend for a penniless Manc. Didn't mind the place too much, worked with a good crowd - one of whom collared me one day, saying that a couple of them were getting a holiday apartment on the coast. Did I fancy going?

I did, but by the time we actually went, several weeks later, the holiday apartment on the coast had mutated into a six-berth caravan on a campsite at a place called Selsey Bill, just down the coast from Portsmouth. I'd seen too many of these shitholes in Wales to think they could ever be really enjoyable and, having spent my first night out on what we (over-expectantly) referred to as 'the pull', soon found that things were no better at the other end of the country. It was fucking dismal.

We spent a couple of boring days looking out of the window at the rain and the nights wandering round the various on-site bars. None of them were up to much - pool tables, arcade machines, shit lager... until I came back from the bar and found Kenny the Glaswegian (the only one who had any real chat) deep in conversation with a very attractive blonde girl, really pretty with a great arse, who looked about my age.

Then, from behind them, up pops her companion - her mother. Frizzy hair, skinny rather than trim, certainly battered round the edges. Probably literally, given where we were. There was a little girl, too, aged about six, really sweet-natured and very pretty with long blonde hair, who was playing with other children in the bar.

It turned out they were staying in a neighbour's caravan and were from one of Portsmouth's roughest council estates - can't now remember which one (I think it was the one famous for paedo marches a decade or so ago) but I came from a fairly rough council estate and even I recoiled slightly when she mentioned it.

To cut a short story shorter we all ended up back at ours. There were no social niceties to be observed - Kenny immediately disappeared with the blonde in the master bedroom (anyone who's ever been in one of these will know exactly what I mean) - and somehow I ended up in the middle bed with the mother (I think the others went for a resentful stroll for a while).

Now in theory I'd have dipped my wick in any woman who offered but I'm afraid this was beyond me. It was only when we were in bed I realised that I really, really wasn't up for it. At all. We fumbled for a while but Mr Floppy was completely living down to his soubriquet. She finally made some inane remark about me having had too much to drink, I eagerly agreed that must have been the case and so we got up and sat on the couches, waiting for her daughter to emerge from the back bedroom, where she was presumably being rogered senseless by the Glasgow Ram.

The others came back and as we sat there, she talked about their life in the most casual fashion - beaten by this guy, raped by that, her daughter raped as a child - it was a true catalogue of horrors.

I was glazing over and, to be honest, wondering if all this was just designed to elicit sympathy when I had the weirdest sensation of movement. It was a strange rocking motion, as if we were on the sea. I looked at the others - they looked back at me.. it took a few seconds to realise that Kenny and the blonde were now really getting down to it and the four of us were noticeably bouncing up and down on the couches as they approached the vinegar stroke. Surreal doesn’t cover it.

And while this happened the mother turned not a hair - not even a pause in conversation. Probably the most natural thing in the world to her.

But what still bothers me is when she told me about the old man who owned the caravan, who they’d come away with. I asked where the little girl had gone - he was looking after her, she said. And then she mentioned that they didn't pay for the stay. Like an idiot I said that must be nice of him. And she said, totally matter-of-factly: "Oh, no - he likes looking after X (the little girl). She shows him her knickers."

I had no idea what to say - or even what to think. This was so far outside my realm of experience that I just did not know how to react, as much as I thought it wrong. Plus, this was the child's mother talking - surely I must have got it wrong, somehow. I hadn't, though.

Even now I feel really guilty that I was told this and I didn't do anything. Do what, though? Take her away? That wouldn't happen. Tell the police or social services? At that time that sort of behaviour was more likely to be ignored than acted upon. There were no graphic depictions of the consequences - people like the old man were the ones you were severely warned to stay away from, with no-one ever wanting to say why. It just left you with the impression that while it’s bad, it can’t be that bad.

Presumably this was how the mother grew up and thought nothing of it. I wonder what happened to them all – did they grow up to be battered and abused in their turn? Was sex as casual an event for the youngest as it was for the other two? Did they end up on the game? Possibly – looking back I think that might not have been an unfamiliar scenario for the mother. What an awful thing to even contemplate – let alone experience.

ps: During the days we remained there, the blonde shagged everyone except me - presumably I got a bad review from the mother. Think I'll live with that, though.
(zebideedoodah likes florence but prefers venice, Thu 26 Mar 2015, 1:35, 3 replies)

I had sex twice and both times it ended in disaster
WE ENDED UP HAVING KIDS HAHAHAHAHAHAHAHAHHAHHHHAAAAAAAAAAAA
( Two Hats I saw someone eating M&M's with a spoon, Wed 25 Mar 2015, 12:02, 6 replies)

My mate told me that when Dodi Fayed took the old princess up the 'aris he repeatedly split her rectum
it was sexual Di's arse tears
( broadsword w⚓, Fri 20 Mar 2015, 21:18, 7 replies)

In a room in a London flat I was doing it in a standing position, thrusting away with her sitting on my computer desk with her legs apart
Worried that she might tip over my new flat screen (back when they were expensive), I decided to move things to my bed. Thinking it would be macho, I attempted to do this without disengagement, picking her up and carrying her there. It was either my trousers around my ankles or my dirty washing on the floor, but I tripped as I neared the bed. She bodyslammed on the floor, and my head (the one on top of my neck) went headbutting through the plaster wall, leaving a hole you could put your fist through. But it all worked out ok. I got my bond back
( cumquat may will not be commenting further on the allegations, Thu 19 Mar 2015, 22:58, 1 reply)

( Amorous Badger NAKED BEA ARTHUR PHOTOS 4U, Thu 19 Mar 2015, 19:12, 6 replies)

Met her in a pub in Kensington
Shocked at how fat she was
(dozers, do fuck off ur a nob m8, Thu 19 Mar 2015, 17:58, Reply)

The unkindest cut of all
Many years ago, before it became fashionable, I persuaded her that pubic depilation was a great asset to my obsession, oral sex, and that I was just the man to perform the introductory shave. Given that it was such a jungle down there, I explained that it would all have to be thoroughly trimmed before applying the razor and, despite her initial protests and misgivings, I took a pair of nail scissors and began Operation Close Shave.

It was all going very well until I was trying to daisycut the stubble to a length that I thought would suit the highest-tech two-blade razor that was available. I'd almost finished Stage One when I noticed a couple of stragglers and lined the scissors up perfectly to trim them as close as I could get them.

The resultant scream as I snipped her left flap had to be heard to be believed. I didn't know screams could be that piercing. Or that she could punch that hard.

It probably would have been better had we not attempted this whilst coming up on some good acid. Still, you live and learn. At least she had something to remember me by that had longevity and wasn't a baby.
(zebideedoodah likes florence but prefers venice, Tue 24 Mar 2015, 23:23, 12 replies)

Tampon trouble
Pearoasted

Back in my student days, when I did such things, I got drunk & picked up a (not terribly attractive) lady who invited me home for 'coffee'. I'd had enough Newcastle Brown for the offer to be acceptable & matters took their usual course until the point of clothing removal when she piped up with 'I'm on, but I'm nearly finished'. By this point there was no going back, so I just grunted & thought no more of it until the deed was done & I was leaving. This being student halls, it wasn't unusual to encounter debris on the floor. I thought I'd picked up some chewing gum or an old pie but when I looked I found a used tampon, that had been flung across the room in a moment of passion, glued to the sole of my shoe. I quickly peeled it off, dumped it in the nearest toilet & went home.
She never spoke to me again, so if you're reading this San, I didn't take it as a souvenir. Honest.
(grumpypolecat, Mon 23 Mar 2015, 18:01, 2 replies)

Many moons ago...
I was seeing an older lady who had a specific kink of me spaffing on her boots/shoes....
All was going well one evening and she was balanced with one foot on the floor and one on the bed sporting a pair of rather nice knee high stiletto boots.
Just as I reached the vinegar strokes she started to lose her balance, I was too far down the road to stop at this point and kept hold of her leg as she hopped trying to regain her composure. She fell with one hell of a crash onto the floor.
She wasn't too upset about the fall it was the fact I came laughing and got some in her hair just 3 hours after a "nice new hair cut".
( tim1701 I have no board signature!!!!!, Mon 23 Mar 2015, 13:33, Reply)

I wish I could claim this was said about me
A friend once bagged herself a Thor-looking motherfucker from her Uni course but found herself unable to do the deed, due to his, er, thunderhammer. Her exact words were "I didn't know whether to sit on it or lean up against it and wait for a bus"
(Darth Foxtrot A one-man army dedicated to making fetch happen, Sat 21 Mar 2015, 8:48, 5 replies)

Wanking disaster
Once I tried mixing things a bit by only stroking the helmet, rather than the usual spasmodic tugging. It takes some patience, but once things heated up, it was promising to be a dozy of an orgasm. I was lying down in my bed, all the tension in my body focused in my groin, ready to explode...

And that's how I came in my own eye.

Edit: doozy, not dozy. Though I do toss myself off to Dozy's livestream efforts.
(McChinaman banned, Fri 20 Mar 2015, 11:30, 4 replies)

Half way through my first time ...
... I realised I had no idea who this person was I was shagging. This bothered me a bit. So halfway through i thought to myself, "I can't do this without at least knowing her name and afterall this isn't exactly as memorable yet as I'd hoped..."
So half way though I stopped, held out my hand announced my name (we actually shook hands!) then she told me hers, we sat back and laughed before continuing like rabbits.
A while later (the deed took place in the back room of a party) a bloke came up to me asked me my name and when I told him he hit me, took hold of what I assume was the lady I'd just been with and man handled her into his car.
He'd broken three of my teeth and I never saw either of them again.
Pretty good shag mind (for a first attempt).
Her name was Laurie.
If you're out there and still remember the 80's ......actually, don't.
(John Elton, Wed 25 Mar 2015, 18:50, 2 replies)

Echoing snores
I had a girlfriend who was very keen on cunnilingus, and I was more than happy to oblige. The way she liked it was not fast and furious tongue flicking, but slow and rhythmic. A little too slow and rhythmic, on one occasion: I fell asleep.
(moon monkey is busy making memories worth repressing, Wed 25 Mar 2015, 12:25, 2 replies)

( 2 Can Chunder Word to your mums, I came to prod bums, Wed 25 Mar 2015, 9:45, 3 replies)

Losing my virginity to MatJ.
He spent months trying to talk me into it, and when I finally let him I was mortified. Looking back, though, I'm not sure it really counted, what with him cumming over my thigh before we'd really got going.
( monster munch person, man, woman... camera... TV?, Tue 24 Mar 2015, 12:28, 1 reply)

I told my friend I had an STD and when I was having sex last night it hurt when I came
"Gonorrhea?", he asked
"No, all over her face" I said
( cumquat may will not be commenting further on the allegations, Tue 24 Mar 2015, 12:17, 16 replies)

There was the time I withdrew, and the condom was hanging off the end of my knob

...which was odd, because I wasn't wearing a condom when I started.
(moon monkey is busy making memories worth repressing, Tue 24 Mar 2015, 10:59, 1 reply)

Zzzz
I'd had far too much to drink. She invited me into her room as I stumbled past. "We'll have to be quite, my room mate's asleep in the other bed", she whispered. I fell asleep on top of her, possibly inside her. "Did we do it?" I asked in the morning when I work up. "Piss off" she said as she booted me out the door.
(Smale is stuffed, Tue 24 Mar 2015, 8:13, 4 replies)

I once said "thank you" after getting a blowjob.
Not the done thing, apparently.
( monster munch person, man, woman... camera... TV?, Mon 23 Mar 2015, 9:22, 8 replies)

I was in a bar in Seattle, not really looking to pull, when she started whispering in my ear "If I get you home I'm going to do such things to you, you wouldn't believe"
but she was a slightly overweight liar. During sex, she mainly lay there like a stunned mullet while I did most of the work. False advertising, I thought.
On the way back from the bar to her place she drove her pickup through two red lights then stopped at a liquor store and asked me if I had money for a six pack. "I need to go to an ATM" I said and she screamed in frustration. Maybe that should have been a warning.
I woke in the morning and left while she snored. I had no wish to make conversation with her. It was six am. Dogs were barking at me. I was in the suburbs. I had no idea where I was.
( cumquat may will not be commenting further on the allegations, Mon 23 Mar 2015, 8:18, 1 reply)

Allow me to repost from 2011
Definitely one to make the chaps cringe......
Many moons ago, when I was but a lad (about 18 and discovering the joys of inappropriateness with the leydees) I suffered from a condition called Phimosis - feel free to google it but it's basically a foreskin that is too tight to retract without causing pain and swelling.....

One evening, lubricated by a number of pints of the lunatic special at the Old Man and Scythe I managed to get lucky with a lady and managed to "do the deed". It hurt like hell but somehow the old fella managed to perform and all was good.

Until later that night. If you can imagine the scenario - the foreskin retracts but decides to shrink around my bellend. Basically I was priapic with a persistent erection and my helmet was turning an angry purple and getting larger. I managed to live with it for a few hours until the pain became too much to bear.

Now the object of my affection that evening was a nurse and thought (due to the effects of being shitfaced) that it would be a simple process to relieve the pressure until I could seek professional assistance. So we commenced the operation...

Nail scissors sterilised in a ligher flame, ice liberally applied to the offending area to numb the pain and the banjo string and the stubborn ring of foreskin around the base of the helmet is cut! I was very surprised how tough human flesh is, even in the most delicate of areas.....

All was good for about 30 seconds. The pressure subsided and things started to look normal then the pain decided to kick in together with copious blood flow. If didn't know I could bleed so much and live. It was everywhere, the sink, the bath, the floor, the bathmat, towels - you name it, it got a soaking.

We decided at that point that a trip to casualty was in order.....the member for Quimborough was wrapped in a towel and the ambulance was called.

It was worth the embarassment of the consultation as the next day I'd had an emergency circumcision and a few weeks later (once the stitches had disssolved/been picked out) I discovered the true joy of sex.

Absolutely true and the most painful thing I've ever encountered but worth it in the end.
(penrose your dog's got tits, Fri 20 Mar 2015, 11:39, 3 replies)

In my more experimental days
Poppers. "Gets you going!" Well the stupid cunt nearly poured the whole fucking bottle down my nose. "Oops..." My entire face turned Alex Ferguson's nose red, I shook helplessly, like a baby in Louise Woodward's hands, and I was shitting myself that my head would do a Scanners.

I've had better nights.
(McChinaman banned, Thu 19 Mar 2015, 19:21, 1 reply)

I had sex
Needless to say I had the last laugh.
(PsychoChomp, Thu 19 Mar 2015, 17:55, 3 replies)