re: Looking back at times where you missed out on an obvious opportunity for sex

This girl I’ve known for years wanted me to go out with her friend on a double date with a guy she was trying to frick. We go eat at a restaurant and then hit the bar.

We end up back at my friends place. She had a fold out couch in the living room for me and the girl. She and the other guy go to her bedroom. The girl and I are making out on the couch when all of a sudden you here a crash.

Apparently, the guy got whiskey dick and couldn’t get it up. She kicked him out of bed and threw the lamp off her nightstand at him. He got dressed and took off in his truck. She came out of the bedroom and told us we’d had to go. I asked her if she wanted to get a hotel room, but she declined and went home.

When I was 17 one of my moms friends, whom I’ve known for most of my life stopped by our house for a visit (back when people use to show up to visit unannounced) but my mom wasn’t home.

She was in her early 40’s, face wasn’t all that great but body looked nice with a set of natural DD’s. I answered the door in swim trunks, no shirt and invited her in. I told her my mom was in Little Rock for the day. She asked where my dad was, and I told her he’s on a work trip.

She says well I haven’t seen you in months and gives me a hug. As she released the hug slowly, she let her fingertips go down my back, stopping at my lower back and gently rubbing it. The whole time she’s looking at me while doing this and I just take a quick step back like a bitch. I don’t know if I was more scared of that older pussy or my mom finding out.

I regret to this day not going in for the kill.

i wont go into boring details on specific instances but on a more philosophical level, the few times that this happened to me, i remember thinking shortly after that "there will be another time" or "i'll do things differently next time i see her" or something similar, but there never was another time for the couple of girls im thinking of.

it's so weird how that happens. i feel like i don't even remember the occasional instances where there actually was another time and things did go differently and we hooked up. those first encounters that i completely fricked up become meaningless due to the second chance, but they weren't any different to begin with.

now, all i remember are the opportunities that were squandered. brains are cruel.

In an Asian county in the late 80s. A roll in the hay (with a good looking native hottie) was usually $20. I was at one time presented with a proposition of two girls at once for $30, for whatever reason I passed (i think to t---ty frick a large breasted gal), I've always regretted that.

Worked with a very good looking and overly flirtatious older Hawaiian woman when I was single. She calls me up and says a bunch of friends from work are going out on her boat for that Saturday. I show up, and it's just the two of us. I don't think too much about it, cos I'm not too bright, and, cos she was married. I could have been Jody, easily. Thought about it, but I didn't want to be the guy that this ultimately happened to in the future.

Now, had she said her husband was cool with it? Prolly woulda given her some disappointment.

Girl I knew really well, total friend zone in high school and college, climbed into bed with me in college and took her shirt off. She was very attractive. I had passed out drunk early on at her house in her bed on top of the covers fully clothed.

I was so drunk I didn’t realize what was going on and said “oh sorry I’ll take the couch”.

Next day she told me what happened and said she tried to hook up and I turned her down and “probably for best anyway, might’ve ruined our friendship”. We are no longer friends anyway.

I think about this so much more than I should.

I’ve had a few but there is this one that was so incredibly hot that it actually bothers me to this day. I was younger than her by 2 years so admittedly I was intimidated.
She had a boyfriend too and I was worried about him because he and his friends were sort of a badass and they definitely would have messed me up. But she was soooooo hot and we were very intimate for about 2 weeks. we messed around a good bit and then it ended. Her boyfriend came back and it just ended.

I think back to one night where it was on. She met me out and we went back to my place at her request and it was so on. I gave her a foot massage, then her while body and she massaged me and it was totally erotic but we didn’t go all the way. It kills me.

I admit that I’ve tried to look her up to see what she looks like today but I can’t find her. Deep down I hope that she aged poorly so I won’t feel so bad.

She was so friggin hot

Thankfully our HOA has banned premarital sex.

If I had a time machine: Note to self, never, ever, miss an opportunity for good sex.