Author Topic: What is your worst missed opportunity? (Read 2952 times)

dobob · « **on:** July 13, 2022, 01:02:46 am »

The missed opportunity that troubles me dates back 40 odd years to my student days, when a girl who had a room in the same flat as my girlfriend declared she'd like to watch us bonk. So we did, and a very timid show under the covers we made. I'd love to know what happened in the alternate universe where me and my girlfriend had thought "sod it, let's give her a show" and lured her in to join along. I suspect it would have resulted in a disaster, but, who knows?

Cheers!

Dipper · « **Reply #1 on:** July 13, 2022, 04:18:52 am »

As a virginal youth after a night out a sexy blonde friend of ours was getting into bed… I jokingly asked “I’ll join you then…” to which she replied “ok” with a smile.

I’m ashamed to admit I completely bottled it and played the polite gentleman, by laughing off her blatant ‘come on’.

Many times I think back to how much fun could’ve been had humping the arse off of each other. I Could’ve and should’ve popped my cherry there and then.

Took me the best part of 18 months/2 years to get my end away from this point. Silly boy.

Ali Katt · « **Reply #2 on:** July 13, 2022, 07:38:00 am »

MMFF a few months ago. I just wasn't up to it I had that really nasty hayfever.

donnybob · « **Reply #3 on:** July 18, 2022, 07:15:30 pm »

Many years ago when my first marriage was breaking up I had a much younger busty but rather plain facially g/f

i was in a flat on my own and the wife and kids in the marital home, my gf said a gf of hers would like to come over, fuck me she was gorgeous, she ran some riding stables and just came straight over without changing, we had a few drinks the night wore on and she mentioned that she doesn't wear anything under her jodphurs

Cut a long story short she went to sleep in the spare room, I checked on her a little while later and judging by the clothes on the floor she was starkers under the duvet, i was kneeling at the side of the bed debating how slowly I could pull the duvet down when my gf woke up and came looking for me

however a few weeks later I had a very good idea of what she looked like naked as she was splashed all over the front page of the news of the world as being the mistress of a very much older man very high up in the horsey world

Oldrich · « **Reply #4 on:** July 18, 2022, 07:29:18 pm »

About 10 years ago ( I am now 63) I was on a work trip to Germany with a younger colleague approx 44 divorced. We
had been away before in groups but never just the 2 of us. After a long evening drinking and having a laugh we went back to the hotel outside my room she put her arms around me kissed me on the lips 3 times then went to her room. I felt guilty as I was already having an affair with her elder colleague. Regret this to this day that I didn't follow it up especially as when we left the bar she said we should go to bed now. Joking not together. As I have now left the company so no chance again.

willie loman · « **Reply #5 on:** July 18, 2022, 07:30:31 pm »

yes its amazing how we ignore it, when its on a plate, had a couple of offers from the carers of a relative of mine, if you are a single mother working in social care , you dont actually get much chance to meet anyone decent, unless its a relative of your clients.

jackdaw · « **Reply #6 on:** July 18, 2022, 08:10:35 pm »

My worst missed opportunities were work related I think…I could have earnt much more money I think if I’d not been such a stubborn git.

mr.bluesky · « **Reply #7 on:** July 18, 2022, 08:26:07 pm »

My missed opportunity is not punting related but in the 80's I was a keen amateur photographer and I would quite often hire a studio and model. The bloke who owned the studio recommended a young model he knew who wanted to break into modelling and would I like to make a booking to photograph her. As she was so young it would only be topless. I agreed and went ahead with the booking. The models name was Debbee Ashby who went on to be a popular page 3 girl who later went on to appear nude in all the big mens magazines. A few weeks before I had chance to photograph her she made her debut on page 3 of the Sun newspaper and had been snapped up by a top modelling agency so was no longer available

A missed opportunity 😢 I had to make do with another model but she was not in the same league as Debbie Ashby

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Liverpool · « **Reply #8 on:** July 18, 2022, 08:45:26 pm »

About 5 years ago I was at a well known dogging venue in Surrey and a couple turned up in a convertible. The couple get out of the car and put on a show of him fucking the woman in various positions in and around their car. At the end they asked if a few of us wanted to join them at a hotel they'd booked. I was one of the ones chosen. I bottled it.

Looking back I really should've gone and may have gotten to shag glamour model/porn star Dannielle Maye.

The Owl · « **Reply #9 on:** July 18, 2022, 09:02:55 pm »

Many years ago an older woman at work was trying to get me to buy a suit she had from an ex-boyfriend. She offered for me to visit her at home and try it on but I refused and tried it on at work in the gents loo. A few weeks later she pulled the same trick on another employee and fucked his brains out at her flat as a fling. I always did wonder if I'd missed an opportunity, she was an attractive but flaky Irish woman.

jayj301599 · « **Reply #10 on:** July 20, 2022, 10:53:05 am »

In my younger days in Wales, I used to work for a company and my colleague was a chubby emo-esque girl. Not pretty but not ugly. She mentioned loads we should go for a drive on the weekends and she'd make it worth my while, signalling a bj. But I was too shy. Sometimes I regret it but other times I'm glad I didn't as I'm private.

myothernameis · « **Reply #11 on:** July 20, 2022, 07:51:30 pm »

Done my time as an apprentice painter, and one day we were sent round the corner, to sauna & massage parlour. I would have been around 22 yr old at the time, and all ready punting, in Glasgow Sauna's

So we get down to our job, of painting the cabins, and lounge, and come the end of the week, we all finished, and begin to pack up. All 3 of us were offered massages, and out of the three of us, myself and one other guy knocked them back. The other guy went for his massage, and later on in the week told us, she got naked, and they fucked

Me pretending, I didn't know any better, and telling my work mate how lucky he was, and a few weeks later in Glasgow, bumped into one of the girls who work in the Paisley Sauna, and she knew why I refused

king tarzan · « **Reply #12 on:** July 21, 2022, 07:47:11 pm »

Quote from: Liverpool on July 18, 2022, 08:45:26 pm

About 5 years ago I was at a well known dogging venue in Surrey and a couple turned up in a convertible. The couple get out of the car and put on a show of him fucking the woman in various positions in and around their car. At the end they asked if a few of us wanted to join them at a hotel they'd booked. I was one of the ones chosen. I bottled it.

Looking back I really should've gone and may have gotten to shag glamour model/porn star Dannielle Maye.

🛑

starman · « **Reply #13 on:** July 21, 2022, 08:56:28 pm »

My first holiday abroad with my mates when I was 17. The hotel we were staying in had a shit disco down in the basement, but a couple of night in we went down to see what was going on. There were 2 cracking girls prancing around on the dance floor. They were with 2 blokes so we had a good ogle (at the girls) and then went elsewhere. A couple of nights later we ended up back in the disco and me and my mate went for a piss. My other mate was puking his guts up in our room and generally stinking the place out with a bad case of the shits. Anyway, as I'm standing wobbling at the urinal in full flow in walks one of the girls and comes up behind me and fondles my bum (which kinda interfered with steady stream of piss but I was prepared to let that go). We started chatting, as you do after an incredibly good looking girl fondles your bum and found out she and her friend were models and the blokes they were with were photographers (Yeah, likely story!). We both lived in East London and she asked if I had seen her picture in the local paper the previous week.(I hadn't). Anyway she asked if my room was in this part of the hotel and said she was leaving for the airport to go home in a couple of hours and what was my room like? Me being a dick head said yeah my room is in this part but my mate is up there and he's got a bad case of the shits. She didn't mention anything more about the room but reiterated that she only had a couple of hours left and did I want to walk outside or go down to the beach. I then said, "Oh, my mate has just bought me a drink". At which point she turned around and walked off never to be seen again. But the real pisser is the following week when I was back home I was sitting in the garden glancing through the local paper and guess whose picture I saw laying on her front butt naked on a furry rug advertising some beauty therapy!

Cactus · « **Reply #14 on:** July 21, 2022, 10:00:05 pm »

Quote from: donnybob on July 18, 2022, 07:15:30 pm

Many years ago when my first marriage was breaking up I had a much younger busty but rather plain facially g/f

i was in a flat on my own and the wife and kids in the marital home, my gf said a gf of hers would like to come over, fuck me she was gorgeous, she ran some riding stables and just came straight over without changing, we had a few drinks the night wore on and she mentioned that she doesn't wear anything under her jodphurs

Cut a long story short she went to sleep in the spare room, I checked on her a little while later and judging by the clothes on the floor she was starkers under the duvet, i was kneeling at the side of the bed debating how slowly I could pull the duvet down when my gf woke up and came looking for me

however a few weeks later I had a very good idea of what she looked like naked as she was splashed all over the front page of the news of the world as being the mistress of a very much older man very high up in the horsey world

So your biggest regret is not sexually abusing a woman by having a peek at her possibly naked body under the covers. The fact you got to the bedside whilst “checking on her” and contemplating this, but stopping as your GF came looking for you is bad enough and a serious violation of her personal space. If your GF didn’t come looking and you went through with it, which has clearly troubled you as it’s your biggest regret, things could have gone VERY badly for you indeed. A spell on the sex offenders register would have been best case, your separation from the wife and kids would have become much more complicated, with you being a convicted perv.

Seriously creepy behaviour, which you call your biggest regret. Think you’ve got some issues.

lillythesavage · « **Reply #15 on:** July 21, 2022, 10:21:26 pm »

Quote from: Cactus on July 21, 2022, 10:00:05 pm

So your biggest regret is not sexually abusing a woman by having a peek at her possibly naked body under the covers. The fact you got to the bedside whilst “checking on her” and contemplating this, but stopping as your GF came looking for you is bad enough and a serious violation of her personal space. If your GF didn’t come looking and you went through with it, which has clearly troubled you as it’s your biggest regret, things could have gone VERY badly for you indeed. A spell on the sex offenders register would have been best case, your separation from the wife and kids would have become much more complicated, with you being a convicted perv.

Seriously creepy behaviour, which you call your biggest regret. Think you’ve got some issues.

Every one reading it probably thought the same, if he did not realise typing it how creepy it sounds, then there was no point telling him

myothernameis · « **Reply #16 on:** July 21, 2022, 10:30:15 pm »

Quote from: lillythesavage on July 21, 2022, 10:21:26 pm

Every one reading it probably thought the same, if he did not realise typing it how creepy it sounds, then there was no point telling him

I wonder if it even really happened

Liverpool · « **Reply #17 on:** July 21, 2022, 10:31:08 pm »

Quote from: myothernameis on July 21, 2022, 10:30:15 pm

I wonder if it even really happened

In which case it's even creepier.

lillythesavage · « **Reply #18 on:** July 21, 2022, 10:33:13 pm »

Quote from: myothernameis on July 21, 2022, 10:30:15 pm

I wonder if it even really happened

Could have a point, even the Sport could not get away with naked on the front page

standardpostage · « **Reply #19 on:** July 22, 2022, 06:56:47 am »

No missed opportunities, on the sexual side.

That I'm aware of

King Nuts · « **Reply #20 on:** July 22, 2022, 10:49:48 am »

Long time ago, before my first marriage, I was friendly with a girl who lived close by. She was the classic suburban blonde, pretty, girl-next-door looks, big tits and ass and I always had the feeling she was up for it, but lack of confidence always held me back. I don't know why. Maybe I was ever so slightly in awe of her, because I fancied her quite deeply. Anyway, I saw her on and off for a few years and then she took off to live abroad.

She came back maybe a decade later. I was married and it wasn't working out and over a drink one evening, she claimed she still really liked me and couldn't understand why I'd never made a move. She'd wanted to, but lacked confidence. Duhhhhhhh.

I suggested we could pick up where we'd left off, but she said she was now happily married and wouldn't fool around on her husband. Oh crap.

So that was that. I've always had a bit of a 'thing' about the short, suburban blonde, big tits'n'ass look, and I think that's where it originated. Could I have made a go of it with her? Who knows. I know she's remained married and has kids, and I'd bet she's still the same babe she always was.

Mr Sinister · « **Reply #21 on:** July 22, 2022, 12:26:42 pm »

Most have been when having equipment failure' while on a one nighter that's why I learned to not drink so much on nights out, dates because you never know when you'll score a corker.

Not the worst but in my early 20s had a mixed group of friends, we would meet up regularly for drinks/rec drugs night outs. There was one big girl who had massive chebs, 30, not a looker at all, she would always flirt with me and be nice, rub my leg even chebs against me sly but I was too inexperienced, shy to go for it I know I could have easily had her as FWB.

One of the other guys in the group had drunken sex with her one time then said he regretted it due to her size.

lillythesavage · « **Reply #22 on:** July 22, 2022, 12:42:48 pm »

Quote from: Mr Sinister on July 22, 2022, 12:26:42 pm

Most have been when having equipment failure' while on a one nighter that's why I learned to not drink so much on nights out, dates because you never know when you'll score a corker.

Not the worst but in my early 20s had a mixed group of friends, we would meet up regularly for drinks/rec drugs night outs. There was one big girl who had massive chebs, 30, not a looker at all, she would always flirt with me and be nice, rub my leg even chebs against me sly but I was too inexperienced, shy to go for it I know I could have easily had her as FWB.

One of the other guys in the group had drunken sex with her one time then said he regretted it due to her size.

At a similar age, my friend and subsequent flat mate had 2 sisters, one a tall big girl who became the end of night bunk up and would fuck anywhere, usually outdoors, so was easy to keep secret, the other I thought was way out of my league and we had little in common, she did not like to party with the rest of us.

At a family do, I was amazed when she started flirting and we began dating, I really liked her even though it was very different from the norm for me, short lived though when some jealous person told her brother about my exploits with big sis, ended in a punch up, and end of little sis

.
Seeing little sis grow into a woman any man would love for a wife irked a little

Mr Sinister · « **Reply #23 on:** July 22, 2022, 01:36:57 pm »

Quote from: lillythesavage on July 22, 2022, 12:42:48 pm

person told her brother about my exploits with big sis, ended in a punch up, and end of little sis .

I've always stayed away from close friends sisters for this very reason. One time with a close mate, a group of us plus sister and her friends were playing truth or dare no dared lol try push the boundaries with the sister there was a few kisses here and there but her friends were fair game. One time the ugliest girl of the group was dared to stick her hand down my pants in the end I went upstairs with her and got a blowjob.

Of course I took a bunch of slack from the lads for it but when young fumbling around with munters isn't the worst thing in the world.

lillythesavage · « **Reply #24 on:** July 22, 2022, 04:01:59 pm »

Quote from: Mr Sinister on July 22, 2022, 01:36:57 pm

I've always stayed away from close friends sisters for this very reason. One time with a close mate, a group of us plus sister and her friends were playing truth or dare no dared lol try push the boundaries with the sister there was a few kisses here and there but her friends were fair game. One time the ugliest girl of the group was dared to stick her hand down my pants in the end I went upstairs with her and got a blowjob.

Of course I took a bunch of slack from the lads for it but when young fumbling around with munters isn't the worst thing in the world.

Sisters used to get me in a lot of trouble

, not relevant to this thread, but one in particular always found a way to be naughty and get me alone, looked like butter would mot melt too.

The good old days hey, not a care in the world

Watts.E.Dunn · « **Reply #25 on:** July 22, 2022, 08:49:02 pm »

Aw, dont yer just luve em really;)

Enjoy!!

External Link/Members Only

lillythesavage · « **Reply #26 on:** July 22, 2022, 08:52:47 pm »

Quote from: Watts.E.Dunn on July 22, 2022, 08:49:02 pm

Aw, dont yer just luve em really;)

Enjoy!!

External Link/Members Only

About 25 years too early, but did enjoy

webpunter · « **Reply #27 on:** July 22, 2022, 09:01:56 pm »

+1
It was good practice
& much more likely to get some action

Numerous times i'd not go for the absolute stunners as unlikely to get anywhere fast
I wouldn't say munters (ok a few) but more the GND & they were well up for it
They felt like the shag of the century at the time
Whereas with the absolute stunners you could spend ages taking them out spending money & get nowhere or next to nowhere
And if your mates never knew about the munter it didn't count

Quote from: Mr Sinister on July 22, 2022, 01:36:57 pm

One time the ugliest girl of the group was dared to stick her hand down my pants in the end I went upstairs with her and got a blowjob.

Of course I took a bunch of slack from the lads for it but when young fumbling around with munters isn't the worst thing in the world.

HighlyMotivated · « **Reply #28 on:** July 22, 2022, 10:19:02 pm »

Turned down a threesome in my uni days because I was afraid my wimpy penis couldn't handle it

badsin · « **Reply #29 on:** July 22, 2022, 11:26:22 pm »

Quote from: HighlyMotivated on July 22, 2022, 10:19:02 pm

Turned down a threesome in my uni days because I was afraid my wimpy penis couldn't handle it

Similar here. 6th form field trip bout 1991 I think. We were 17/18.
Two really nice (fit) girls, they came onto me...I took the back massage off them both but absolutely bottled it on the turnover 🙄
Still friends with them both. A mate of mine has been partners with one of the them for 25+ year's. She mentioned this event once, christ...... that was a chat....turned round into me being a pussy for not going for it.
Thankfully the other episode's never got a mention.

Bro's before ho's fella's

*I could write a review type account of this as it still gives me the horn all these years later *

cunningman · « **Reply #30 on:** July 23, 2022, 12:14:27 am »

Quote from: Mr Sinister on July 22, 2022, 01:36:57 pm

I've always stayed away from close friends sisters for this very reason. One time with a close mate, a group of us plus sister and her friends were playing truth or dare no dared lol try push the boundaries with the sister there was a few kisses here and there but her friends were fair game. One time the ugliest girl of the group was dared to stick her hand down my pants in the end I went upstairs with her and got a blowjob.

Of course I took a bunch of slack from the lads for it but when young fumbling around with munters isn't the worst thing in the world.

Surely a 'comely woman' that wants to have fun is better than a princess? Then and now?
I never think 'munter'. Could be a comely kinky nymphomaniac.

catweazle · « **Reply #31 on:** July 23, 2022, 10:55:49 am »

For a couple of years, I was the quizmaster at my (then) local pub quiz night. It was fun, and my "pay" was free beer.

Two m/f couples would always take part, stood at the bar. Over the months, as they were always there, I got to know them quite well. One of the women, Stephanie was a 30 something blonde with big boobs, which were usually well displayed in plunging necklines.

One evening, chatting to the four of them after the quiz , Stephanie kissed me - in full view of her fella, who didn't react in any way.

Over the weeks, it developed into full-on dfk snogging, again with nothing from her bloke.

One day she slipped something into my pocket. In the gents ' I had a look. It was a business card, which simply said "Stephanie" and a mobile number.

Stupidly, I never followed up. The pub changed hands shortly thereafter, and the new landlord cancelled quiz nights.

webpunter · « **Reply #32 on:** July 23, 2022, 11:05:59 am »

What a bell end you are

Thought you are supposed to be klevva to be a quizmaster ?

Quote from: catweazle on July 23, 2022, 10:55:49 am

One day she slipped something into my pocket. In the gents ' I had a look. It was a business card, which simply said "Stephanie" and a mobile number.

Stupidly, I never followed up. The pub changed hands shortly thereafter, and the new landlord cancelled quiz nights.

Edit:
I've been given a mobile number or three
On one i was in between finishing with one civvy & another on the horizon
Didnt follow it up
Left it too long & the opportunity passed me by

catweazle · « **Reply #33 on:** July 23, 2022, 11:26:30 am »

Quote from: webpunter on July 23, 2022, 11:05:59 am

What a bell end you are
Thought you are supposed to be klevva to be a quizmaster

I was asked to be quizmaster as I kept winning the quiz as a (solo) participant. But yes, really really dumb of me

webpunter · « **Reply #34 on:** July 23, 2022, 11:28:31 am »

We all make mistakes
At least you had the opportunity in the 1st place

Quote from: catweazle on July 23, 2022, 11:26:30 am

I was asked to be quizmaster as I kept winning the quiz as a (solo) participant. But yes, really really dumb of me

daverfc · « **Reply #35 on:** July 23, 2022, 11:31:02 am »

Back in my younger days, I was dating a student who was studying at university. She had a shared house with about 5 other girls. One of the girls was my GF's best mate at uni and so we all kinda hung out a bit a lot.

One time we'd had a few drinks and a threesome conversation came up and it was actually my gf who suggested it between the three of us. The other girl seemed game but we'd had too many beers by that point so decided to do it another time....

That other time never came about. That would have been a cracking fuck.

willie loman · « **Reply #36 on:** July 23, 2022, 06:21:21 pm »

my girlfriends mate visited one night and we all shared the bed, me in the middle. while my girl friend pretended to be asleep, i with some difficulty penetrated her mate,we were face to face , with a bit more lead from me, a full on threesome would have been on the cards, i would go on to see her mate on a few occasions,

threechilliman · « **Reply #37 on:** July 23, 2022, 06:51:19 pm »

Many moons ago, whilst still living with my parents, a female friend rang one evening to see if I was 'going out' that evening. What she was actually ringing about was to invite me to a MMFF she were organising. Sadly I was on holiday abroad at the time and I recall being pretty pissed off having missed it (another fella deputised for me that evening). Fortunately, she organised the same thing again a couple of weeks later and a good time was had by all, save the previous occasions deputy of course. We repeated a few times, adding the deputy for an additional M and quite a spectacle having her ride me whilst watching her boss get spit roasted on the living room floor.

Technically not a missed opportunity, but the couple of weeks after finding out I'd missed the initial one had me gnashing my teeth.

Ali Katt · « **Reply #38 on:** July 24, 2022, 07:12:59 pm »

I could have shagged Ava Coxx at GFE in Sheffield about 10 years ago. I didn't know she would become one of the best known UK pornstars; she is mega tall - could probably pass for Post-Op TBH.

webpunter · « **Reply #39 on:** July 25, 2022, 01:11:03 am »

Is that Ava Koxxx's sister ?

Maybe 5 years ago she was soooo close to where i am, 15 mins drive tops
150 for 30 mins
250 for the hour
Then the prices went off the scale 6-12 months later
I noticed that she was just down the road & texted her
A fast reply saying that she was leaving the hotel in the next hour & was busy with a sorry

Possibly post, but with her looks & rackage far from certain
& in any event if you cant tell it doesnt count

Recall mentioned on here that she was @ SS forever ago

Quote from: Ali Katt on July 24, 2022, 07:12:59 pm

I could have shagged Ava Coxx at GFE in Sheffield about 10 years ago. I didn't know she would become one of the best known UK pornstars; she is mega tall - could probably pass for Post-Op TBH.

Ali Katt · « **Reply #40 on:** July 25, 2022, 06:37:44 pm »

Quote from: webpunter on July 25, 2022, 01:11:03 am

Is that Ava Koxxx's sister ?

Maybe 5 years ago she was soooo close to where i am, 15 mins drive tops
150 for 30 mins
250 for the hour
Then the prices went off the scale 6-12 months later
I noticed that she was just down the road & texted her
A fast reply saying that she was leaving the hotel in the next hour & was busy with a sorry

Possibly post, but with her looks & rackage far from certain
& in any event if you cant tell it doesnt count

Recall mentioned on here that she was @ SS forever ago

Sandy's and GFE shared girls. Mainly for bragging rights, but who can you talk to it about other than other punters?

webpunter · « **Reply #41 on:** July 25, 2022, 09:13:11 pm »

One of my mates (who was caught) had to talk about his (very occasional

) punting exploits as part of his divorce hearing
In Court

Quote from: Ali Katt on July 25, 2022, 06:37:44 pm

Sandy's and GFE shared girls. Mainly for bragging rights, but who can you talk to it about other than other punters?

WDFORTE · « **Reply #42 on:** July 25, 2022, 09:32:12 pm »

Bitcoin

myothernameis · « **Reply #43 on:** July 25, 2022, 10:01:50 pm »

Quote from: webpunter on July 25, 2022, 09:13:11 pm

talk about his punting exploits as part of his divorce hearing In Court

Interesting, wonder if any of the male jury or males in the gallery took notes about the escort

Escort asks, how did you hear about me, new client in a divorce case

webpunter · « **Reply #44 on:** July 25, 2022, 10:08:40 pm »

Well there was more than one escort
Think he admitted to a couple
Not a CSI forensic examination but he did say it made him squirm a bit
Before the case moved on, phew TFFT
Tho his ex did score some points
Unfortunately his ex wasnt into sex (evaporated after kids) so diddly chance of catching her out having an affair

Quote from: myothernameis on July 25, 2022, 10:01:50 pm

Interesting, wonder if any of the male jury or males in the gallery took notes about the escort

Escort asks, how did you hear about me, new client in a divorce case

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Author Topic: What is your worst missed opportunity? (Read 2952 times)