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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)
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This question is now closed.

It's an odd concept to me. I don't think I really regret any shag I've ever had. I ain't a fucking oil painting but then almost nobody is. Oh sure I've had girls who make people jealous and had to face the taunts of friends for humping what they called a whale or a facially challenged beast of burden but I can honestly say at least I got to have real sex with a real person while my picky friends had to console themselves with their hands. So yeah, like everyone I do have some stories of missed opportunities but I count them as part of my journey through life and every real encounter was one less wank, wonderful though wanking is my old numb handed buddies.
Regrets though are the subject so I must admit I bloody wish I'd done more and taken every sodding offer that came along. I bet some of them would have been unforfuckinggettable.
(, Sat 10 Dec 2011, 2:41, 9 replies)
A few years ago,
I was was working in a club in Scotland. We closed early one night so i decided I'd pop over to the bar we all went to on sundays and have a wee pint. I was in there for about half an hour - sober - amongst a bar full of drunk people. That didn't last long though, quite a few of the local girls started buying me nasty little shots with nasty little names and things got blurry.

Anyhow, i noticed across the bar a tall blonde woman was wearing a hustler shirt. She made eye contact and when i said "nice shirt", she lifted it. A bit unexpected, but later I end up at her house drinking coffee and whisky while she talked on the phone to someone. After maybe twenty minutes she finished her conversation and we went outside for a smoke, got halfway through before the tongue-wrestling began, then up to her room.

She must have been early thirties, but had a stunning body. I got her clothes off and noticed she had very nice lady bits so I went down town for pizza. Thought i did a marvelous job, and when I couldn't hold back any longer I came up and mounted her.

She was asleep.

This is what I did:

Pulled out, got dressed and took her bottle of whiskey for the walk home.

This is what i should have done:

Stuck it in her arse, jizzed under her pillow and taken the whiskey home.
Fucking wish i had.

Turns out she had a boyfriend who approached me at work a week later, I denied everything, he was a cunt anyway. And it turns out quite a few of the local ladies fancied me, hence the free shots. I never had a clue. Now I'm on the other side of the world in a long term relationship with one of Hitler's offspring.

Sorry about the length not being used more deviously on that cunts girlfriend.
(, Sat 10 Dec 2011, 1:17, 40 replies)
Not the biggest but the first that sprung to mind
Me and hubby thought we'd make a film of us having sex...fuck me, it was awful - the only redeeming thing about it was when I thought to watch it at high speed, which was quite funny. Now ex hubby :) (Not just because of that!)
(, Fri 9 Dec 2011, 23:42, 5 replies)
And when I opened my eyes, my mum was standing behind me with Hartley the Hare.

(, Fri 9 Dec 2011, 23:29, 3 replies)
My mum's biggest regret is shagging YOU.

(, Fri 9 Dec 2011, 21:50, 19 replies)
Captain oblivious strikes!
I've had at least 4 occasions now been chatting with various cute, interesting, and extremely taken friends of mine (married, engaged, long-term boyfriend, etc.) who've come out with the line "You know, I really fancied you before I was going out with X."



Why could they have not said this -beforehand-?
Why did no-one let me know?
Why was I not observant enough to notice?
Why do we not get a manual or handbook for this kind of thing?

When I think of some of the (not trying to be crude about it) hawt ladies I could have been involved with it drives me spare.

*wailing and gnashing of teeth*

There is actually another specific incident that still narks - the (apparently traditional) failed threesome.
Two young ladies and I, faintly drunk, all down to underwear and in bed, and misc fooling around.
One of them pipes up "Y'know, we could have him", to which I respond with a ha-ha-I-know-you're-only-kidding laugh.

Of course at this point, one of them is draped over me exploring my chest with her mouth, and the other is astride my crotch, and I've got a member you could have hammered nails with.
The magnitude of my idiocy knows no bounds. It all petered out and we went to sleep after that.

(Incidentally both of them came to me independently afterwards and said words like "You'll be lucky if that happens again. I know you fancy *other woman* more." There's no easy way of saying "can't I have you both" at that stage.)

(, Fri 9 Dec 2011, 21:20, 1 reply)
once, when visiting the town i grew up in
i went out for beers with some mates from way back when, and got monumentally, staggeringly, drunk.
I do vaguely recall licking the tonsils of some comely lass and taking her outside the club to find somewhere to get 'more intimate'.

During the next morning's dissection of events a friend's sister informed us all that the girl I copped off with had been - during her school years - a passenger on the special bus.

Didn't quite manage to live that one down.
(, Fri 9 Dec 2011, 20:50, Reply)
My biggest sexual regret
Was shagging your mam....
(, Fri 9 Dec 2011, 20:21, 2 replies)
If you ever pump your penis full of silicon
until it's eighteen inches in length and six in diameter, and the ideal recipient lady embarks upon a "stretching" campaign, wedging progressively more massive objects up her muff until it can accommodate things that would make hardened porn actresses head for the door, then assuming you can stuff it up her you'll find afterwards your mutual sexual organs completely unfit for purpose. Erections will be impossible, conventional toilets impractical, clothes will need to be custom-made and embarrassing. Ladies will be ashamed by their grotesque, misshapen vaginas that will repulse future sexual partners, be more liable to infections, and take a hit in self-esteem and comfort.

That's the biggest sex you'll regret.
(, Fri 9 Dec 2011, 20:16, 3 replies)
I had large white heron staying round my house for the night. He seemed civil enough.
But when I knocked on the guest room door, I found him rubbing one out to a framed picture of my mum.
And that was my big guest sexual egret.
Apologies for, well, existing, I suppose.
(, Fri 9 Dec 2011, 19:41, 7 replies)
I had a threesome
In Blackpool, on a stag do (Do I need to go into details about just how much alcohol was involved?). I was sharing a very small room with 2 friends. One of them pulled a girl, and my other friend tried some sort of long-game tactic on her friend instead of going in for the kill.

Anyway the 5 of us went into the small room. my 2 friends were in bunk beds and I had the double bed (I paid for the room, obviously)
Friend number 1 hops into bed with his lady and they begin doing the horizontal monster mash.

Friend 2 decides to conclude his long-game by saying to his lady friend "lets go see Frample"

And so I had a threesome or 'spit-roast' as I believe its called.

And I can honestly say I will never do it again....

...Even if she is fit next time
(, Fri 9 Dec 2011, 18:15, 12 replies)
Still think about this....
I was 18, she was 36 and my mum's work colleague. There was a party at our house and I was dancing with her. It did a hell of a lot for my hormone-addled adolescent's ego when she whispered into my ear "I want you to fuck me".

Although there were snogs, gropes and many other lust-fueled acts over the course of the next few months, we never quite found the opportunity to actually fulfill her wish (and, believe me, it was my wish too!). At that point, I went off to Uni and opportunity was completely lost.

Just once would have been nice....
(, Fri 9 Dec 2011, 17:25, Reply)
I regretted this

So I made sure not to make the same mistake with Bumbleflap.

(, Fri 9 Dec 2011, 17:17, 7 replies)
Regrets? I've had a few.
But then again, too few to mention.
(, Fri 9 Dec 2011, 17:08, Reply)
I wish I'd been wanking when I posted this.

wanking shooting fish in a barrel
(, Fri 9 Dec 2011, 16:47, 6 replies)
Second biggest regret..
Biggest sexual regret was posted earlier "Why I hate the Bee Gees".

As a 22 year old I went to the fair Greek isle of Spetses with two mates of mine. We went with a company called Twentys which was like an upmarket version of Club 18-30, or Club Aids 'n' Herpes as it was known. We were in a hotel with 40 others, of which 5 were male, two of those being gay.

We ignored the obvious charms of the 2 cock teasing catwlk models who would drape themselves over lads until they got a free drink. Instead we hooked up with 4 ex-Catholic High School girls from a rougharsed area of South London. They were a great bunch, all good fun and very bright , with varying degrees of beauty.

Most nights I would end up chatting with M (for that was her first initial)who was the least attractive of the 4 but the most fun. Afetr a few nights we had a night to ourselves drinking cocktails overlooking the sea and a glorious sunset.

Our romantic night together was interrupted when her friend burst into the bar the seek refuge from some Greek blokes who were pestering her. For her protection I had to pretend to be with this other girl, Frances, to deter the Greek lads from bothering her. This entailed me sitting next to Frances all night with my arm round her, holding hands etc. Eventually the Greeks lose interest and sod off. M and I walk Frances back to the hotel and she thanks me profusely (this isn't turning into a failed threesome)

Frances decides to call it a night so M says "Shall we go for a quiet walk on the beach" I am now heroic and gallant in her eyes for protecting her mate. We walk on the beach but within 10 yards we are out of sight behind a sand dune snogging. After much foreplay the time was right to mount up. Here I was on a beach with a naked girl, about to enjoy the delights of the lesser spotted ginger minge for the first time. I exhaled and just said "Oh Frances". Ooops.

Immediately I realised what I'd done and apologised as she ran off the beach, knickers in hand. She avoided me for the next few days then all of a sudden it was the last night and the leavers disco. Towards the end of the night she came over smiling and we kissed and made up. We both laughed about it and we had a slow dance.

What was the song we danced to? Well it was 1984 so appropriately enough it was George Michael ......."Careless Whisper".

To this day I have not and now never will experience the delights of the ginger minge.
(, Fri 9 Dec 2011, 16:38, Reply)

Never have sex with a boy who has a projector in his bedroom and insists on pausing Ghostbusters while you insert Tab A into Slot B.

The night I made that mistake is the night I found out that looking up at Dan Aykroyd's shocked expression made a million times bigger by being stretched across the wall all the way through sex makes me feel ashamed (and regretful).
(, Fri 9 Dec 2011, 16:30, 1 reply)
Conversation with an ex-girlfriend
We'd been going out a few weeks and rutting like rabbits, and were getting past that into something a bit more open, maybe. You know how it progresses. So we're chatting in bed:

Ex: Is there anything you'd like to do?
Me: Do?
Ex: You know...
Me: Oh! Right. Um... *goes shy*
Ex: You can tell me.
Me: But maybe you won't like it, and I'll feel embarrassed.
Ex: Just tell me.
Me: You won't like it.
Ex: Maybe I will.
Me: What about you, is there anything you want to us to do...?
Ex: Not really, I like what we do.
Me: So... you don't want to try anything different?
Ex: Don't change the subject! You can tell me. I won't be offended.
Me: It's not you being offended that's the point.
Ex: Well tell me then.
Me: *sigh* Okay then... *tells*
Ex: ...
Me: So...?
Ex: No chance.
(, Fri 9 Dec 2011, 16:19, 14 replies)
A lesson learned ...
~~ wavy lines ~~

It's always important before anal sex that all participants are relaxed. There's nothing more guaranteed to be painful than even mildy stressed bumming. So anyway ... picture the scene ... Hartley the Hare
(, Fri 9 Dec 2011, 16:10, Reply)
Female only piercing.
Imagine if you will a rather beautiful sex goddess with no clothes on.
Now imagine her perfect labia enhanced by two silver rings , one either side.
Imagine my delight at sticking my solid meat pole between said rings.
I did not imagine the pain I'd be in not twenty seconds after penetration after my rather long testicular pubic hair got itself tangled around the piercings and then my enthusiastic hip slapping managed to pull them free from my skin.

I Imagine she was not impressed at my crying all night.
(, Fri 9 Dec 2011, 16:10, 7 replies)
That last one reminds me . . .
25 years old, roughly. Female friend of mine, part of our group, who I'd always fancied a bit, brings another friend on a night out, and me and new girl end up in bed. This turns out to be quite a long relationship, about 5 years in the end.

Anyway, year or so later, original friend (Amanda) moves to a place in Buckinghamshire. She's single, lives by herself.

Me and the girlfriend go to visit. We have a few drinks over dinner, off to bed, fiddling around with each other, GF suddenly says 'Why don't you invite Amanda to join us?'. In my pissed state, I just chuckle quietly, and fall asleep.

Next day, a bit more sober, I say to her with a laugh 'You were trollied last night, you told me to go and get Amanda for a threesome'

'Yes', she says. 'She once told me she would quite like to do that'.

Pissing shitbollocks. I suspect it was probably better in the end that we didn't, but if I had realised it was a serious suggestion, I'd have been all over it.
(, Fri 9 Dec 2011, 16:04, 17 replies)
Following on to a previous post on this topic I was more into computers than girls up until around the age of 18. It was around this time that I started noticing this apprentice hairdresser working at the rather expensive salon across the road from my office.

Each season all the staff would wear a different uniform and this particular summer it was dungaree shorts with a black crop-top underneath. By my reckoning half of the girls in there were sporting at most 3 items of clothing each that summer and this one girl finally started to get my hormones a buzzing.

But this isn't really about her.

Leaving the office one day I was talking to a colleague about this unnamed chick across the road when our 16 year old office junior piped up that the girls name was Laura and she used to go to school with her and could perhaps introduce me to her. I hadn't really noticed the office junior at this point as she was rather... plain. Let's call it plain.. to be nice.

I started talking more and more to the junior to glean morsels of information that may assist me in my quest to have this dungareed temptress. She clearly took this as some sort of come-on and started to flirt with me. I was pretty oblivious to this as there were now only 2 things in my life. My Atari ST and dreams of Laura.

Jackie the temp decided to up her game one evening by bashfully presenting me with a small wrapped gift.

It was a condom.

"I know this looks forward and I'm not as attractive as Laura. But I'd really like to do this. I've never done it before."

my 17 or 18 year old virginal brain suddenly went into hormone mode at this prospect of an almost guaranteed cherry losing moment and to my shame, despite having no attraction to this girl I clinically arranged for the deed to be done.

A few weeks later my parents went away for their summer holiday so I arranged to pick Jackie up on my Honda 125cc Moped from her home in the flats.

Cutting the rest of the sordid details short I ended up rooting around in her guts for at least a good 4 minutes* before hopping off and delcaring myself spent. Despite her protestations about being scared of getting on my moped again I insisted it was the only way she could get back home and dropped her back on the outskirts.

She asked for a repeat performance on a number of occasions but I'd ticked the box and was happy to go back to the Atari ST again.

My regrets?

1. Making her take a terrified motorbike ride back home after she'd given up a gift she'd never be able to give to anyone else.
2. Not having a few more goes to get some practice before meeting a girl I really liked.
3. Never getting to rummage around inside Laura's guts as I'd lost my cherry and pretty much lost interest in girls for another 12 months.

* ok. 2. or 1.
(, Fri 9 Dec 2011, 16:04, 8 replies)
When I was 18 years old
When I was 18 years old, I set off for University.

My mother - not one to see her first born live out his Uni years in a run down old student house, decided along with my father to invest in a second property - namely a flat just outside the town centre near my University.

To say I was beside myself was an understatement - this place was the dogs bollocks.

In retrospect, I believe that I lost out on part of the experience of University - in the sense that I shared the place with no one - save for my neighbours.

In addition - I was also presented with a series of very strict ground rules - to name a few, no parties, only 1 friend over at a time (I know, I know) - looking back on it now, it was pretty harsh, but being only just 18, and with very little worldly experience, I obeyed my parents to the word.


So during the Freshers party, I bumped into this girl, who we will call Sophie.
It was strange, we took one look at each other - and I knew exactly what was going to happen that night.

Over the next couple of months we saw each other purely for sex. She didn't want any strings attached because she wanted to concentrate on her course work - I was to afraid to commit to anything as well, so all was good.

The flat my parents had invested in became my own personal sex cave - we shagged everywhere, and it was bloody marvelous.


Anyway - about 2 weeks before Xmas, I get a call from 'Sophie' at around 2:00 in the morning on a sunday - she's been out all night, is totally wrecked and wants to get down with the dirty.

Brilliant I thought, I was asleep, but was now totally geared up for her coming over…
That's when she asked whether her friend could stay aswell….

Asked the same question now - I would say no problem, expecting nothing in return, but at 18, and with the rules my parent's and laid down, I said word for word "I'm not allowed to have anyone else stay - I'm sorry"

After a brief exchange on the phone, She asked if it was ok for her friend to come in for a coffee and use the phone to call a taxi - to which I obliged her.

Everything was fine, until the taxi arrived, and we all went to the door to see her off.

Sophie's friend turns to her, french kisses her right in front of me….
then turns to me, kisses me as well and says the following words which have forever haunted me.

"you do realise you could have had us both right?"


She smiles, All I want to do is beg, but my 18 year old, loyal conscience prevented me from doing so.

"OMG are you fucking serious??????" I said to Sophie

"yeah, but it's cool - I understand about the flat and your folks and stuff, there will be another time"


I banged her out so hard that night - unfortunately that 'other' time never happened. And we stopped seeing each other shortly after Xmas.

Total and utter regret
(, Fri 9 Dec 2011, 15:52, 11 replies)
my mid teens
Ah fuck it, lets just go with what Drcuntface says ;) saves you reading all of what was here
(, Fri 9 Dec 2011, 15:50, 8 replies)
Just the one..
and a bit boring really but it's the first time i've answered one of these.

Girl at work, fancied her for ages (and she knew it) but as she said when i asked her out we all know work relationships should be avoided at all costs.

Anyway, works night out and at a point in the evening she asks if i'll walk her home (result i think!) but later on we ended up going to a friends house instead with the intention of getting a taxi home.

All is not lost though as when said taxi arrives she says, 'shall we just go to mine or do you want him to go to your flat after he drops me off'. I, of course, chose the latter.

Who knows, maybe she expected me to walk home straightaway after the taxi dropped us off (it was only a 20 min walk from there) but deep down it was a Rob Newman 'Oh no, i've just blown the chance of a definite shag' moment
(, Fri 9 Dec 2011, 15:42, 1 reply)
Too many to choose from.

It took me a long time to get to the point where I could tell the difference between my arse and my elbow, sexually speaking. Along the way I did a lot of stupid things - shagging women I didn't really know or even like very much.

And worse, I missed a whole host of opportunities to shag women I knew and liked, preferring the whole "worship from afar" bollocks. I'm 44 now, and at a guess I reckon I've wasted a good 15 years since my balls dropped following around women I fancied because I had some romantic dream that they'd come to love me if only I hung around long enough, without once making so much as an oblique hint that I'd like to get jiggy with them - no, somehow that was rude and uncouth, beneath my lofty romantic ideals.

All this meant that between the ages of 20 when my college sweetheart dumped me, having only lost my cherry about 8 months previously, and about 30 when I got into the habit of shagging whenever I got the chance (including, I'm ashamed to say, more than a few "sex workers"* if there was nothing else on offer), the most I did was wank on my own.

*I stopped doing this the day when I happened to catch an episode of Trisha when I saw a girl I knew from somewhere, but couldn't quite place. The episode was called something like "My daughter is a prostitute and wants to quit, but doesn't know how". It's the first and last time I've paid more than ironic attention to that sort of TV, let me tell you.

After that, everything seemed to calm down, I've had a couple of really rather good relationships that ended amicably and two years ago I met the woman I want to grow old next to.

The morals of this story, kids, are:
1. JUST DO IT when you're young, kids
2. Make sure you have a healthy and harmless sense of what "IT" really is once you get past 30
3. If it seems like nothing's going right for you and you just can't seem to get what you want, don't worry so much - the whiff of desperation is about the least attractive smell around, and in time the situation will change, or you will, or both.

Apols for lack of funnies
(, Fri 9 Dec 2011, 15:33, 2 replies)

Several years ago, I was going through a bit of a rough patch. Money was tight, my landlord was being a dick and I had probably the worst summer job I've ever had. However, the worst thing to happen was breaking up with my girlfriend at the time, whom I had grown particularly fond of.

Suffice to say, I wasn't in a good place and still being at the tail-end of teenagerism, much angst was had.

One Wednesday night on the way home from work, a female colleague of mine (whom we'll call "D" for now) admitted that she broke up with her girlfriend. Oh that's right, D was a lesbian. And not the pretty kind. In fact, she was in her late 20's but somehow was already missing a few teeth. What teeth she had left were at awkward angles. A pretty smile, she did not have.

The topic of her muff preference had come up a few times before, she'd been with men in the past but wasn't all that fussed on them. She simply preferred women, much like I did. After a few drinks and some consoling, I walked her home as that seemed like the right thing to do.

Now before you get too excited, I know what you're thinking, it DIDN'T happen. We didn't sleep together.

...until the following Saturday! After much more drinking, we both decided that frankly what we both wanted right now was a good shag and that's what at least one of us got.
Ok, that's somewhat unfair - for a woman that hadn't been with a man for the better part of a decade, she certainly had a few tricks up her sleeve. I was no slouch, either, possibly from being a bit of a manwhore in my slightly earlier youth. In fact, I genuinely surprised D who later admitted that she at thought I'd be completely shit. Never mind the fact that I was a man and couldn't possibly compete with a woman. Well, compete I did.

So much so, in fact, that D also admitted that I had converted her. She was no longer a lesbian "experimenting" but would quite happily tell people that she was Bi from now on and would, in fact, stick with men for a while.

And that's why I regret what I did. Because of me, the ratio of straight, pretty girls to straight, ugly ones has been tipped slightly towards the uggos. I'm really sorry, everyone.

Length? Wasn't much of an issue, she was a dirty bitch.
(, Fri 9 Dec 2011, 15:24, 15 replies)
I'm too nice, evidently
I have a long list of sexual regrets, mostly involving fat or ugly lasses, or mate's girlfriends, but one regret is by far my biggest.

It's the usual tale of a missed opportunity.

Many years ago, in a city far, far away, I did a boring job for a boring company. The office consisted predominately of blokes in their early 20's, women of a certain age and one girl who would definitely qualify as a hottie. Her name was Louise and she was as fit as a butcher's dog. She was the total package: pretty face and a slim body with amazing double-D tits.

She was on a neighbouriung team and I'd never really spoken to her that much. until, that is, we got stuck on a project together that required us to spend a week in each other's company. During this time, we chatted a lot to pass the time and it quickly emerged that we had absolutely nothing in common. Like seriously nothing - we liked different music, films, TV, books, football teams, food, cars, holiday destinations, bars, clubs... everything, basically. The only thing we had in common was that we are of the same species.

Despite the glaring differences, we got on like a house on fire and became really good friends. We'd chat via email all day, have lunch together every day and text each other all evening. We then started going out with each other, purely as friends. Since she lived with her parents and I had my own flat, she would often come round for the evening and would quite often spend the night, but they was no sex involved, only the occasional snog and a grope.

Our relatioship was best summed up when she drunkenly told me "you're like my gay best friend who isn't gay".

So one day, she texts me to say she's had an awful day and is coming round. She'd been at her grandad's funeral and some petty family squabble had bubbled over into a fight. When she arrived, she was pissed and clutching a full botlle of vodka. We (well, mostly her, to be honest) proceded to finish off this bottle of vodka before she announced that she didn't want to go home and would be staying with me that night.

We climbed into bed and snuggled up, like we always did. I was nearly asleep when she poked me and said "Scouse, I want sex"
I was suddenly very awake and said "what, with me?"
She slurred "yep, with you, right now"
And I said "no, you're pissed and emotional"
She said "I don't care, I want you"
I said "You don't really, you're too drunk to know what you want"
She said "Oh, okay" and went to sleep.

Not only am I still kicking myself about this now, ten years later, she still loves to remind me that I'm too nice to get in her pants.
(, Fri 9 Dec 2011, 14:23, 11 replies)

This question is now closed.

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