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This is a question Biggest Sexual Regret

Our glorious leader Rob asks: Most of us have done it, right? You've seen a grown lady/man naked, right? What's your biggest regret connected to The Acts of Venus? "Your Mum" does not an answer make, but big fat lies about threesomes are welcome.

(, Thu 8 Dec 2011, 13:34)
Pages: Popular, 7, 6, 5, 4, 3, 2, 1

This question is now closed.

Hooray, I just thought of one
Some years ago I met a girl at a club, and ended up going home with her. Now that was not a common event, I can tell you - Cassanova has nothing to fear from me. Even more amazing, this girl was not only smart, pretty and funny, she was also 19 -- I was 35 at the time, so this was fucking amazing.

I'm not really a one-night-stand kind of guy (probably due to lack of opportunity, if I'm honest) and this was no exception - because we didn't get out of bed for two days. In the lulls between shagging like teenage rabbits, we talked, and it turned out that she had always considered herself a lesbian. But, after breaking up with her long-term girlfriend a couple of days before, her mates encouraged her to "find out how the other half live", and for reasons which entirely escape me, she chose me.

Now, I can hear the rumbling sound of an oncoming wall of "Honda Accord! Supermodel! Massive Drugs" accusations, so before you accuse me of blatant fantasizing, I can tell you that it didn't all go well. Clearly I would have loved to have carried on seeing her, but she decided that she didn't want to get into a relationship again, so soon after breaking up.

Yes, reading that back I know it sounds like a brush-off, and that I was so terrible in bed that she wasn't interested, but you'll have to trust me when I say that that certainly wasn't the case.

So, to the regret: it's not that I didn't convince her to stay with me. No, it's worse than that. A couple of months later, I bumped into someone in the street, and while they clearly knew me, and looked familiar, I couldn't place them. I'm very absent minded like that. It was only after they'd disappeared into the crowd again that I remembered who they were: my teenage godess's mate, and hence the only way I had to contact her again and possibly get together with her more permanently.

(, Fri 9 Dec 2011, 14:18, 5 replies)
I had the chance to have sex with another 4 women (not at the same time) when I were a lad.

1) Andrea (I think) 1st year at uni, she wanted it, I wanted it but had no condoms or access thereto (I was in the halls miles away from any shop and it was 2am)... only when she left did she tell me we could've done it cos she was on the pill. Balls. (having said that, she clearly had no clue about STDs so maybe it was a lucky escape?)

2) Laura, she was the sister of a friend, she had inordinately long nipples which amused me but her parents were in the bedroom next door and I simply couldn't get past that mental block, making it impossible to go through with the deed.

3) H (for that is her initial), I had a massive teenage crush on her when I was 27, but I was proper messed up and rather than noticing she was interested, I presumed she wasn't... even when I woke up next to her (I spent many nights in her bed with her) and she was naked. What a twat I am.

4) N (for that is her initial also), my only chance of sexing up someone who isn't caucasian but to be fair, we'd done too much of that illegal stuff in a nightclub before heading back to hers... I just laid there coughing all night after attempting to stuff my sausage meat into her glove...

Individual regrets yes, but the main reason I regret all 4 is that my favourite number is 23 and I've only shagged 19 girls...
(, Fri 9 Dec 2011, 14:02, 40 replies)
Receiving felatio from a lady I'd just met
in the toilets of a nighclub in north london (stay classy). Unforunately, for one reason or another, possibly due to the effects of alcohol (that's my exuse and i'm sticking to it), I was finding it quite difficult to come. The regret part came when she eventually took my penis out of her mouth and said "that's weird, the other guy couldn't come either".

Other guy?? We'd been snogging like a pair of teenagers only ten minutes previous.
(, Fri 9 Dec 2011, 13:56, 9 replies)
I don't know
What is it do you think? Is it that when a young man is in love, his happiness and self-confidence makes him more attractive to other women?

I’ve not performed the beast with two backs (two heads, four legs and arms and a conjoined set of sexual organs) with that many women, and I’ve certainly never had to bat them off with a fly swat, exept when I was twenty-one. In that year, I turned down three offers of sex from more than averagly attractive women, and all within weeks of having met the girl of my dreams (versions I & II).

Just twenty-one, lean and tanned, on Naxos; I’d just waved good-bye to the girl-of-my-dreams v1, when I was approached (that evening) by a pair of lovely Scottish nurses. One of them was so clearly smitten with me it was embarrasing (not for me, just everyone else). She even listened to me going on about the girl that had gone…what a knob I was. Why do I regret this? Because a couple of weeks later, I had no hesitation in having a one night stand (on a ferry) with a German girl – which I most certainly don’t regret.

The next time was 9 months later, shortly after meeting Xena – who would become Mrs Grimsdale. I’d been mildly flirting with the Canadian cousin of a good friend for a few weeks, but I had to put a stop to that when she started to get more obvious – at my 22nd birthday party. Shame really, because she was a big girl, and very pretty and I would have dearly loved to get acquained with her simply massive boobs, but it wasn’t to be. One week later, at my brother’s flat, I was introduced to a friend of his girlfriend. Very attractive, probably mid-twenties, slim and blonde. We all four spent the night playing cards (while I pined for Xena), and there were forfeits in the form Tequila…fast forward a couple of hours and I was lying on the floor like a semi-deflated blow-up mong doll, with this girl lying next to me, whispering in my ear “Che, I want to make love to you.” I was so very drunk that I can’t quite remember what happened, but I’m fairly sure we were both down to our undies…

…next thing I knew I was kneeling in the toilet with liquid/semi-liquid gushing from every orifice. So, regrets more about the drinking than anything, because I may well have been tempted to have one last shag before settling down forever with Xena.

That all said, I’ve no regrets about staying faithful to Xena for over 25 years. And it’s not just the (fairly) regular sex either!
(, Fri 9 Dec 2011, 13:26, Reply)
A shag is not a shag
A recent post from TheManOfScience reminded me that a shag is, indeed, not always a shag. This was brought home to me quite trenchantly when a housemate bundled into my bedroom one morning (way back when i was in my early 20s) ... we were sharing an old terraced villa in Portobello, Edinburgh's seaside-with-beach suburb ... Anyway, housemate caught me immediately post-flagrante and stood there open mouthed for a while, not managing any actual words, just strangled syllables. The sheet was pulled up - it was all very decent, nothing on show - but finally i thought i better break the silence.
"It's no big deal," i said, "I just had a shag."
"No you haven't," he squeaked. "That's a cormorant."
(, Fri 9 Dec 2011, 13:25, 6 replies)
I once had a sex-dream about Nicola Bryant,
but woke up before it turned wet. I was gutted.

Similar thing happened involving Brigitte Nielsen, but that just feels like a lucky escape.
(, Fri 9 Dec 2011, 13:20, 3 replies)
I regret never having got to shag Sophie Grigson before she got gigantically fat.

(, Fri 9 Dec 2011, 13:14, Reply)
I once wanked over a picture of Mary Whitehouse.

(, Fri 9 Dec 2011, 12:56, 8 replies)
Not putting two and two together
My 31 year old self, if I could intervene when my 14 year old self gets a bit aroused at a picture of an elf woman in a fighting fantasy gamebook, and pauses the dice rolling action to have a wank, might say to me that if I did a bit less of the former, I might need to less of the latter
(, Fri 9 Dec 2011, 12:37, 2 replies)
Yes I Do.
I was in on my own one evening and decided, in contravention of God’s direct orders, to spill my seed on stony ground.

I also decided it was time I knew what kind of face a pulled at my moment of crisis. I’d tried this in the past by looking in a mirror, but as every Schrödinger fan knows this never really works.

It was few years ago when videotronic recording devices where still quite expensive and not included in every phone, but I did have a video camera, so I set it up, had a wank etc, and went to plan.

Of course the following week I lent the camera to an acquaintance who was using it for some university project and loads of people got to see the tape. Praise the fucking lord that this was before the internet was video enabled.

Anyway, the thing that people found amusing was my lack of focus on the job at hand. I was stopping to watch telly, getting up to grab another beer, smoke a fag. The sound of the telly was clearly audible as well. After 40 minutes I finally got my freak on to the unmistakable sound of an episode of Dad’s Army. Years later and there’s still an occasional ‘Who do you think you are kidding Mr Hitler’ or ‘Don’t tell him Pike!’ from the people in the know.
(, Fri 9 Dec 2011, 12:33, 7 replies)
Every. Single. Time. that I've turned down sex
Mostly from being too young, inexperienced and scared to get the hint. Particularly the time in halls of residence when a girl whose main topic of conversation with me was about what a nymphomaniac she was, randomly knocked on my door - sober to boot - and started rubbing herself against me and asking if I wanted to wrestle. I told her her boyfriend would be back soon. She didn't have one. She wasn't wearing a bra, or - apparently - knickers.

No, I don't know what I was thinking. I suspect that goes beyond cluelessness and into the realms of some sort of medical disorder.

That's just the one that stands out most. There were several others. So; I regret every single shag I've never had, and none of the ones I have; no, not even the one that gained me a demonstratively self-harming stalker (which was around the same time as the Nympho Fail Incident), or the time I fucked my brother's girlfriend when he was out the house for ten minutes.
Actually, I have a suspicion that somewhere around 21, my shame circuits, sick of their strenuous working conditions, just packed it in and have been on strike ever since.
(, Fri 9 Dec 2011, 12:26, 5 replies)
It's indirect
but I definitely regretted the effect it had on my view of the opposite sex.

Basically, if your mate introduces you to his friend who's a gynaecologist, under no circumstances should you ask him what his worst stories are. I couldn't look at vaginas the same way for a good few weeks...
(, Fri 9 Dec 2011, 12:12, 8 replies)
A Shag is a Shag = *WWWRROOONNNGGG*
Just isn't true. Young horny men (and wimmin I suppose) getting your end away with any old person that wanders by ISN'T big nor clever. It's not even fun. Mostly.

You'll find this out the SECOND you blow your man mayonaise (men) / errmm... dunno? (wimmin) as the guilt washes over you and you realise the seedyness of the situation you're in.

Take it from me, A Shag isn't a shag.
(, Fri 9 Dec 2011, 11:56, 17 replies)
The first girl who i had a sexual relationship with (So it is a tenuous link). Ok it took me 10 years to tie the knot with her but i was only 16 when i met her and its too young to fall in love and into anything approaching a long term relationship. I split with her after over 20 years together and its not been fun. I wish i had left it till later and had a bit of time being single and having a laugh first.
(, Fri 9 Dec 2011, 11:52, 7 replies)
First Time Trauma
Both I and the lass in question had never discussed it until that evening, but as we were getting naked together for the first time - a few months into the relationship - we found out we were both still virgins.

Within thirty seconds of being inside her, I saw she was bleeding a lot more than I expected a girl would for her first time. I pulled out, nervous I'd been hurting her. She asked what was wrong, then saw the blood seeping from her and over my groin and over the bedsheets and freaked out.

She tried to get to her shower to clean up but fainted at the sight of her own blood, taking the full weight of the fall on her nose, breaking it in the process. Had to get her delirious self dressed and take her to the hospital. Had to answer lots of awkward questions about how she ended up in that condition. She blocked my phone number when she got out; embarrassed by the evening.

I felt I'd rushed sex. I'd wrecked a great friendship. I regretted it for ages. Took four years and waiting for the right person to feel it was OK to try to have sex again.

Me and the gal bumped into each other about six years after the incident. We went to a pub and we caught up over a few drinks.
Quote of the evening? Her summary of the relationship:
"The relationship kinda fell flat on its face that night, didn't it?"
(, Fri 9 Dec 2011, 11:49, 5 replies)
Having a fetish...
...cos there's nothing like awkwardly bringing up something you want to do in bed to kill the passion. And no, I'm not saying what it is. Except that it's not animals or scat or anything like that.
(, Fri 9 Dec 2011, 11:33, 61 replies)
It's not a story, but...
...I'd like to introduce you all to a word I invented*:
Schagenfreude: Taking pleasure in the sexual regrets of others.

(*Am sure someone's beaten me to it somewhere, because it's pretty obvious...)

**EDIT** Dun a google and there's 50 results - although a few are typos for schadenfreude...
(, Fri 9 Dec 2011, 11:33, 2 replies)
Hotel hooker...
It’s a long one – but hear me out…

15 years or so ago…

So there I was - a fresh faced 17 year old (might have been 18 but can’t remember) on my way to Harlow with my boss for a training course on how to sell PC’s (for a well known retailer).

Checked into the Hotel late and went to bed, went to the training course the next morning and upon returning to the hotel – it was decided that we would be heading into London that night for drinks and swearing.

We were joined by 2 chaps from Sheffield who were looking to let off steam and with 4 of us – it would make a cheaper taxi…

Off we went… drinks were had, pubs were visited. All in all – a good evening in progress.

Coming up to 11pm now and I’m starting to lag. My boss pulls me to one side and shows me a little bag in his pocket. ‘here – eat this’ he says. Within 20 mins, I’m talking like a horse racing commentator. I had just had a nice chunk of Speed – in its paste form. And judging by the look of my friends – so had they. The night was now young again.

Eventually – we roll back to the hotel about 2am and pile back to my room to talk at each other and smoke cigarettes. One of the lads spies my Loaded Lads Magazine and is having a flick through the pages – he comes across the classifieds at the back of the mag – and amongst the adverts for growing your own hemp and funny T shirts, our hero spots an advert.

‘Emmas Escorts – all areas’

We all agreed that this was a great idea – and we should book a ‘lady’ to attend to us asap – we phoned – they said she would be an hour and it would be a £60 call out fee for a massage – anything else is negotiated.

We sat and discussed how best to proceed. Blow jobs were the way forward, we all wanted one and as the Boss was paying the lions share, he would get to have her first. He would then tell her that there is another chap (me) in another room who would like a BJ. She would then attend to me and I would tell her that there is another chap in his room looking for a similar deal – and he would repeat these steps. It was fail proof – we all get a nosh, she pockets a few quid and everyone is happy. We congratulated each other on our ingenuity and looked forward to what was to come.

Well that was the plan… we had an hour to kill before she arrived.

We went to a cash point as we’d need at least £60 for the call out. I wanted to get a shower as I was pretty minging and had the worst brown coloured perished undies on – plus I thought it was only fair on the poor lass if I’m at least clean before she pleasured me.

But. As the hour rolled on into 2 hours – the Speed started to lose its effect and we started to come down and I was losing my confidence and starting to panic.

With that – she arrived. And my god was she amazing – Scandanavian, flowing blonde hair and cowboy boots… Jesus H Christ!

We got down to the point – there were 4 of us in the room and she sat on the bed – we asked about ‘extras’

Handjob - £60
Blowjob - £110
Full Sex - £200

That was not including the £60 we already already had to pay – so a BJ was £170. Bugger – thinking we had hatched the perfect plan – we had neglected to include the fact that we were not hiring some ‘Northern Lass’ who frequents dockland areas, we were in London and hiring a classy lady – who it turns out – we couldn’t afford.

We are now pretty much sober – so my boss throws £60 on my bed and says ‘Pat – I’m off to bed, you have the massage she came out for then’ and with that he left, and so did the 2 other lads, leaving me on my own with a beautiful blonde.

I may have forgotten to mention that at this point I was 17-18 years old and full of bravado – but I had as much experience with women as Ray Charles had with hanging wallpaper. I was terrified. I was way out of my depth.

‘Do you want to get undressed and lie on the bed?” she enquired?
“err – yeah’

I hadn’t had the shower I planned on having earlier – I drop my pants to reveal a horrible threadbare brown pair of boxershorts with my testicles clearly visible hanging out the bottom (I distinctively remember leaving my socks on too). I climb on the bed and she gets her massage oils out. She starts rubbing my back, I make token appreciative moans – but deep down I’m not interested. And judging by the amount of effort she is putting into the massage – neither is she. I get the impression by the fact there is a lot of oil everywhere – that massage is not her specialty.

I lie there listening to BBC News 24 talking about Bill Clinton whilst a blonde woman with cowboy boots straddles me and massages my back.. I should be on cloud 9, but instead I stop her, thank her for coming, and hand over the £60. “lets just call it a night” I said – she agreed and went off with her rather small minder who had been waiting outside.

I lay on the bed reflecting on what had just happened, turned off the tv and went to sleep.

30 mins later – the phone rings. ‘Pat – is she still there? – I’ve been the cash point and have enough for a wank – send her up’ I had to explain that she had just left and that the plan had changed since we all went to bed. and with that my phone rang again – ‘Pat – is she still there? It seems that as everyone went to bed – they all got hornier and on reflection decided that they probably could afford it.

We went home the next day. I had a hundred thoughts running through my head. WHY, WHY, WHY didn’t I make the most of it – even if I couldn’t afford anything – why didn’t I just ask her to stand in her underwear whilst I cracked one off, why didn’t I plead poverty and ask her for a cheeky tug, why didn’t I ask her to take off her bra while she gave the massage? Why, Why, Why…

Even writing this now makes me want to travel back in time and slap the younger me in the face and ask what the hell I was playing at…

No apologies for length – you could see it through my boxershorts….
(, Fri 9 Dec 2011, 11:29, 6 replies)
the time...
...when I stuck drawing pins into the shaft of my erect penis, took a picture of it and posted the picture and some clippings of my pubic hair to Trinny Woodall out of 'Trinny & Susannah'...

.....in all seriousness my biggest sexual regret is probably screwing other women behind my ex-wife's back and generally being a horrible philandering cunter :0(
(, Fri 9 Dec 2011, 11:22, Reply)
Nietzsche was right all along
I was always pious. And into computers. So I never really got close to a girl until I was 20. This was the now Mrs Chutney. Unfortunately she was a signed up Christian, youth groups, bible study before bed, everything.

She was great otherwise, and we got it together in an enthusiastic couple of weeks. Kissing is great! Who knew? But then she fell into a fit of holy angst when it came to anything physical. Despite a good bit of early groping, I never actually got to see her nipples for a few years. I genuinely loved her and believed anything she told me, and she did indeed believe it herself. I was actually happy with the situation.

Anyway, all this fell away over time. Theres no reason or purpose to life other than to do the best with what you've been given. Plato (I think) figure that out around 400BC. And so we are now happily married.

Its true that the world doesn't owe you a living. But you don't owe it an apology for being born either. I'm now (oddly, hypocritically perhaps) pleased that shes the only partner I've had, and vice versa. But I still wish I'd fucked her good in the first week. And then wiped myself off on the curtains on the way out.
(, Fri 9 Dec 2011, 11:01, 6 replies)
Biggest regret, and related to sex.
My first serious boyfriend. He introduced me to many things. Drug-fueled sex. Drunken morning uni classes. It didn’t work out because I was young and naïve and he was a pig*. It ended somewhat badly.

~~~wavy lines~~~

...and we both matured in the ensuing years, I thought. He acted Not-Pig well enough to convince me that we could be “ex-lovers that are now just friends” (I have since been schooled quite well that this is not a possibility in the known universe). He needed help with some grad school report and asked me to help, offering to drive me in his new car and show it off.

In the spirit of friendship, I agreed (idiot move). We went to his place. 20 fucking miles away from my car and flat. Of course I helped with the report and it got later and he offered some wine. I had a little. He had more, and oafishly dropped hints, and then outright proposed that, at the moment, as I was not with anyone, and he was not with anyone, that “we ought take care of each other’s needs.”

I declined, and said I thought it was high time for me to get home and was he okay to drive? This angered him, and he swore at me and said “You can get yourself home!” and went to sleep. In the days before ubiquitous cell phones and cell phone coverage, I ended up walking 2 miles in the dead of night to the nearest petrol station, too furious to be sensibly terrified.

I called my sister (bless her heart,) who came 10 miles to pick me up, let me sleep at her home, then got me home the next morning.

Did the wanker ever call to check if I’d made it home? No. I never spoke to him again. He occasionally attempts contact on stalkbook and such, and doesn't understand that I am no longer young and naïve, but he is clearly still a pig.

My regret? That I didn’t take his brand new car and drive it home, park it with the keys in the ignition in a nearby chavvy street, and leave it there.

My excuse to the polizei would have been "I must have misunderstood him when he said to get myself home! Did I forget the keys in the car? Oh dear!"

*and I never did fancy the way his bits slapped against mine on a warm night.

(, Fri 9 Dec 2011, 11:00, 1 reply)
I've mentioned this before, but you know that look girls give you when you're DEFINITELY getting laid?
No, me neither. That's why I didn't lose my V-plates til I was nearly 19...
(, Fri 9 Dec 2011, 10:26, 6 replies)
Non, je ne regrette rien.

(, Fri 9 Dec 2011, 10:16, 2 replies)
Murdering all those hookers
I'm sure they wouldn't have told my mum, thinking about it.
(, Fri 9 Dec 2011, 9:33, Reply)
I've had a few chances of a threesome and even one opportunity of a foursome
but unfortunately The Holocaust.
(, Fri 9 Dec 2011, 9:09, 5 replies)
I never did get those sweeties.

(, Fri 9 Dec 2011, 9:02, 9 replies)
The List

I was about 26 years old, when during a friendly discussion at the local before a night of clubbing, the conversation moved on to heaven. Everyone piped up with theories until one friend came out with the following:

"Well" he began, whilst taking a quick sip of his pint "I was at this comedy show one time when the guy doing stand-up made a quip about heaven. He said that all of the religions had got it wrong, and when you die, what actually happens is a guy shows up with a clipboard and simply passes it to you."

"And...?" we all asked in wonder.

"And on that clipboard is a list, with the names of every woman in your life that would have had sex with you had you merely asked".

He went on to tell us that all of the women at the show burst out laughing, whilst he sat shocked, gazing around and seeing similar expressions on the faces of every bloke in there.

The same expressions on all of ours around that pub table all those years ago.

I've never looked at life the same way since.

My greatest sexual regret is that I didn't know about 'The List' sooner.
(, Fri 9 Dec 2011, 8:50, 33 replies)
Fuckin' Munters
I've turned down the odd shag in my time, often with someone who I've felt is a bit below standard e.g. too fat, too old, too ugly. Although it's probably the right decision, there's always a slight pang of regret. A shag is a shag after all.
(, Fri 9 Dec 2011, 8:03, 2 replies)
One morning I woke up on a sofa
Not unusual, but it wasn't my sofa. I had no idea where I was - some living room in some tower-block flat, it seemed. And I had no idea how I'd got there. On the other end of the sofa was a middle-aged female gorilla, snoring heavily. I don't think we'd done the dirty - we were both fully clothed and I had no horrifying memory fragments of fat boobs or chunky varicosed thighs, so I was good to go. A noise caught my attention, and I looked up, to see two young girls, obviously female gorilla's offspring, nervously standing by the door. I tried to tap the shins of the slumbering monstrosity to wake her up, but I was still drunk and give it a bit more welly than I'd intended. So two girls, aged about seven and five, saw a twenty-five year old Chinaman kicking their passed-out mother in the leg, before he rushed past them to get the hell out.

Not my finest hour.
(, Fri 9 Dec 2011, 4:25, 7 replies)

This question is now closed.

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