If I had only KNOWN THEN what I know NOW!

Lots of missed opportunities. If rebirth is something that exists, I want to come back as a woman, that way I'll get all the sex I want. So much easier than a man in that respect.

In my early 20's, I was far too picky and "nice". So many girls I could have pounded and didn't.

I hear ya there. I was also in relationships. Shudda stayed single.

Three missed opportunities come to mind.

Studying with a girl in high school who at first I didn't find particularly attractive. She allowed her blouse to open, braless, and exposed large areolas. Didn't grasp she was seducing me.

In college library restroom, an older male student with an unbuttoned shirt exposing a very hairy chest approached me, rubbed his crotch, and urged me to follow him. Still scared of my bisexual fantasies, I left the restroom quickly.

I was in a seedy bar on a business trip, and an attractive woman approached me and asked to dance. We danced closer and closer, and I felt her, and realized she had a penis. I made an excuse I had to leave.

I still jerk off thinking of them, wondering what might have been.

The paradox is always like when you're single there are no opportunities, but when you have a partner then there are tons of opportunities that you [usually] cannot go for. Grrr...

I had an online jerk buddy who was somewhat local when I was about 19-20. He wanted to meet up but he was twice my age. We were pretty close friends and jerk buds online, and sadly with time we grew apart and fell out of contact. Looking back, I really regret not taking that leap. I had a connection with him that I've been chasing with other jerk buds ever since.

Oh well.

I got a ride while hitchhiking way back when. Really nice mannered guy talked me into undressing completely in his car in a remote area. He gave me my first ever bj. Offered to take me to his home to play more. I chickened out after the bj. It was fun but sorta wish I would have gone home with him.

A few years ago I was chatting with a woman I knew in HS but never got with her then. Then 40 years after HS we ended up hooking up for a weekend. It was a great time and then she said "You could have had this 40 years ago and every day since if you hadn't been so shy" She's right, I was shy back then.

When I was in high school 2 girls wanted me to by them some beer. They said they would give me a blow job if I did. I said no. So one of them said how bout I fuck you. I still said no. Guess I missed out that time

True story, I was in a bar on halloween with some friends and a girl and her husband came up to me and liked my costume and asked if she could wear it.

I said no, and she said "I'll give you a blowjob in the bathroom if you let me wear it".

My girlfriend was with me at the time, so I had to decline, but then her husband said "its cool man, I don't mind".

Looking back I should have just gone for it.

When I was around 9/10 and still at primary school a female classmate wanted me to go back to her house to "play". She had several older brothers and hinted that she knew quite a lot about boys. Unfortunately she actually was a bit smelly so I didn't.

Within around 18 months my hormones had kicked in and I was wanking almost non-stop and wouldn't have cared how smelly she was - but by that time we were at different schools and I never saw her again.

I will always regret not doing a threesome with my GF and a friend of mine in high school. I was so scared of what people thought of me back then (even though I was sucking my best friends dick regularly).

My GF told me she had a crush on one of my friends and said she wanted to fuck him but wanted me involved too and that she'd already talked with him and he was okay with it. I declined, but we did end up fucking in front of him as he jerked off.

I later found out she fucked him many times over about a two year period. Found out she fucked nearly ever male friend I had. I knew she had some dick on the side and I was fine with that, I just didn't know who.

Looking back I wish we'd have played as a couple. All that delicious dick I missed sucking and watching her get filled with big cocks.

Oh heck yes I do. From my youth, my early adulthood, my middle adulthood, and well even still. Usually didn't realoize the opportunity until too late.

I know what you mean about still missing opportunities. The last time I was in a casino before the pandemic, three different older guys smiled at me and were checking me out over by the machines. I didn't realize until later that they were cruising me. Oh well, I was with family.