Pre Covid I am in my local pub and have a good chat with a couple in their 50's who are proper regulars. The guy is a real good guy and the woman is the owner of the most enormous set of breasts. Absolutely eye-watering. This time she is rather drunk and tells me all sorts of stuff goes on in her hot tub with various folks. She asked me if I could handle 'these' and leant forward giving me a fucking beautiful view of her cavernous cleavage. I flirted for another half an hour until she asked if me and my missus as a couple would interested in the hot tub experience. At this point, contemplating my wife, who I know would not, no way, no how, be into this, I reluctantly said no. Her disappointed face I can see right now.
Every time since that I have seen her no mention of that drunken conversation has ever taken place and I know the door is probably shut.
Damn fool - I could at least have gone on my own!

Missed opportunities to spank a good butt.

I've got countless missed opportunities and could easily have doubled my fuck-tally if I'd taken up what I now realise were obvious offers. Ah well...

my thoughts are .. did you at least copy the sessions?

I was very shy when I was younger, in every way, not just with women. Had many missed opportunities with some lovely ladies unfortunately, but have thankfully made up for it in later life when I became much more confident and well aware of when to turn on the charm and how to do it.

When I was a teenager a much older female friend of my Moms came round to show off her new sports car. She visited fairly regularly and was very posh and prim and proper, and was also very attractive and although much older than me I fancied her like mad.

We went out to look at the car, and knowing I was into cars, she asked me if I would like to go for a ride. Of course I said yes, and the two of us sped off out into the countryside. We were away for about half an hour, she was real chatterbox and didn't stop talking so there were no awkward silences. She parked outside my house to drop me back, and then started showing me all the controls and flashy optional extras on the car. When she reached across to open the glove compartment her hand brushed against my leg. She didn't say anything, and then when she moved her hand back she rested it on my thigh, still talking away and I started getting a massive erection in my pants. She glanced down at my jeans then moved her hand to the gear stick. 'This feels nice to hold in your hand' she said softly in her posh sexy voice, I can still hear her saying it now, and with that she started slowly moving her hand up and down the gear stick, at the top of each stroke stopping to roll her thumb gently over and over the gearknob. I sat transfixed, quiet and very flustered. She gave me a lovely smile, and said she had to go home and make dinner. I thanked her for the ride, got out and waved bye bye.

She still visits family to this day, but neither of us has ever said anything.

Had so many wanks thinking about that afternoon and wishing I had known what to say or do.

100% true story.

Borderline painful to think of these, as I am currently in a very cock-obsessed stage of my life and there were so many opportunities with my buddies when younger, as well as business trip JO buds I arranged but then chickened out.

Girl-wise.... one of the hottest girls in my HS, at our 20th reunion, got drunk and grabbed my dick and made out with me a little. Said she'd always been lonely because guys thought she was unapproachable and she had wanted me to go out with her. I was married and this was in public so obviously both embarassing and dangerous, but when I thought of my HS-aged self I was like "IDIOT!" Though at the time it would never have even occurred to me to ask, she seemed completely out of my league - guess that was her problem.

Maybe worst of all... when I was about 26, I was fucking a girl I'd met online... she had gigantic creamy tits and underneath the slutty thong panties she wore on our dates was a juicy oozing pussy that tasted like cantaloupe - really! - and I could tongue her to orgasm 5-6 times per night even before I fucked her. We'd only hooked up a few times before the night when I came on her face and then slurped and swallowed my load off her. She didn't seem too upset at the time, but the next morning she emailed saying she didn't want to be with me anymore and it's pretty clear to me that was the reason. I reached a point where I had to stop jerking off to memories of her because the sense of lost opportunity and loneliness was too great.

I wish I hadn't been so shy in my teens, I found out that at least one curvy lass would have been up for some fun if I had just asked. My other regret was settling down too young and not exploring other opportunities with a few sluttier lasses.

So many lost oppotunities so many regrets. Here is one of them:

When I was 18 and living in a small village, there was a cute woman (in her late 30's) working as a bar tender at the local pub. She was knowned to be a slut and a nympho. My buddies and I went sometimes to that bar for a beer. We often chat with her but nothing else.

One weekend night, my friends and I were at a night club in a neighbouring town (about 30 minutes drive). One of my friends sees here getting inside the place. We started laughing and asking ourselves WTF is she doing here? She comes right at us like it was the most natural thing to do, like we were good friends. About 1 hour later, she wanted to leave. She starts talking in my ear and asks me to go with here because she didn't want to drive back alone. I decline saying it was too early in the evening. I tell her that she shall ask another one of my friends. Nope, it has to be me. She insists saying that she was afraid to drive at night in case her car breaks down. Then, I get it. And then, I start getting nervous (but still trying to keep my cool). The reason, I was still a virgin and got scarted to loose it with a late 30 year old woman knowned in our village to be a nympho. After she left, my friends asked me what she was telling me. When I told them, they all agreed that I was the stupidiest guy on earth.

Several.

I delivered newspapers when I was a teenager. There was an older fella who must have been dropping hints for months before I caught on. The last hint was so obvious but I didn't quite understand at the time, knowing only that guys and girls 'went together. I stopped at his house to deliver and collect and when I knocked, I heard him say, "Come in." He was sitting, feet up, in a recliner, a couple of Playboys on the coffee table beside him. He reached over, picked up his wallet and as he did, I could see the head of his cock sticking out of the leg of boxer shorts, which he had tucked up so it would show. "Here you go," he said, gesturing with the money. "The usual, right?" And as I got closer, I could see it swelling and getting harder and him grinning. It was a total Big Bad Wolf situation, complete with him saying, "Oops, sorry. Don't worry. It won't bite." I got close enough to grab the money and back toward the door. His smiled slipped when he saw that trap wasn't going to spring. "Say, uh, don't mention this to anyone, okay?" And I didn't. For years afterwards. He never tried again and I've sometimes wished he had. Knowing what I know now, that was a heck of a nice cock.

A woman friend of my mothers' made a play for me once that I completely misunderstood at the time. I started early so I knew what was what, but I didn't understand flirting. And it didn't occur to me that when a woman, not a girl but a real, live woman, 'accidentally' made sure that when she turned over to talk to you while you had just finished mowing her back lawn and you were coming to get paid, the tie of her bikini bottoms came undone enough to expose her nether regions to the sun, and you, and that she knew that she was exposed and stayed that way, smiling, on her back, legs apart, she was inviting you in. She asked how much she owed me, smiling behind those mirrored shades. She stopped smiling when I mentioned a dollar amount. While I did regret not following through that time, she tried again the following summer. THAT time I got the hint and took it out in trade.

And lastly, when I was in college, I volunteered at a local church. By that time, I could take a hint and knew when the game was afoot. There was a girl that kept throwing big signs. She helped with a Sunday school class and was obvious in how she might be willing to make herself available, always when no one was looking. Slim, sweet, tall like I 'em, and very pretty. One Saturday, while we were all in the parish hall sorting things out for a charity event, I looked over and saw her sitting cross-legged on the floor, in a skirt. She was trying to catch my eye. When I finally looked long enough that she knew I was looking, she twitched the skirt and showed me that she was wearing nothing underneath it. She winked, I blushed, she dropped the skirt, put a finger in her mouth, and I excused myself to use the restroom, after which I pled stomach upset and bailed. As well as I remember the sight of what was under her skirt, I will never regret not taking advantage of the opportunity. She was sixteen.

I could have easily up my fuck count but my fuck stick has been in plenty of people

Oh, my god, I think of the times in elementary and junior high when on the way home from school a girl would want to get into the bushes with me and show her my cock.

Seriously, I was sporting an 8" cock back then and someone in gym class must have spread it around. Girls would grab my crotch in the hall and I'd almost run, I was so embarrassed. Sure would love to time travel back to those times! I missed a lot of sex!!

I don't think I regret it. Boy I certainly missed on quite a few. But I've also had a few I wasn't expecting.