Any time you regret not going for sex?

[groomleader]

I'll add my time. I was 14, alone with my 14 year old girlfriend, in her house. Her bother and my brother had gone out with their dates, and we knew they wouldn't be back for a while. I talked her into modeling her bikini for me. This was 1972, so her bikini was quite modest by today's standards, but I still saw a lot of her skin that I had not seen before. I was too damn shy to try to put any moves on her, and just admired the view. That's the time that I remember, and wonder "What if?"

[pzmking]

There was this woman, Annie, who lived down the street from me. Her and her boyfriend/babby daddy- whatever he was had a few arguments in the street. He was a drunk asshole. She was trailer trash with a six and an 11 year old kid.

One night, I came home from work and he was pounding on her front door. I yelled at him to stop. Another neighbor yelled out the window that she had called the cops. The drunk asshole took off running. Annie came out and assumed I had chased him off and thanked me as I was walking*to my apartment.

Around midnight, I get a knock on my door and it's Annie. She started telling me about how I saved her a lot of headache by chasing the creep off. We didn't really know each other but here she was in my apartment after dark with the door shut. I can take a hint usually but for some reason it didn't exactly hit me that she wanted to fuck. We made small talk and all the signs were there but I was just too stupid to take the bait. And she was exactly the piece of ass I like too. Blonde, middle-age, about*145 lbs, 5'5''. Worn down and lived in. A bit vixenish, chewed up and spit out. That was pretty much a gimme, free piece of ass from the universe gift that I just passed up because I was a naive idiot not able to read women. Tried to take her up on it a couple days later but she shot me down. The moment had passed and I blew it. I made sure not to ever let that happen again after that. Even if it meant making an idiot of myself and guessing*wrong. At least the woman would know that I was interested even if she wasn't.

[pzmking]

You mean you had more chances like that after that night?
Not with her but other opportunities with other ladies came along that I capitalized on (or tied to anyway).

[storypost603]

yes back when I was 18 we use to have an older girl hang with us and she use to ride with me a lot of the time. She was at least 25 and we had stopped at my house a few times with no one home to grab things and I never made a move on her. I look back now and think wow how dumb was i..... She was hot also.

[dreamwriter]

Two I wonder "what if" about. One I got together with when she was older... she was 14 when we first met (I was in my 20's) and she asked me to take her virginity... I quite nobly said no... we got together when she was 18 by which time she was very experienced and quite the slut. The other was a former girlfriend who was 16 at the time and also asked me to take her virginity... again I said no because there were issues with her parents about the relationship and I didn't think that she was serious ... Though that was some time ago, I sometmes kick myself for not saying yes, I loved her a lot.

[Funcle2003]

Im 35 yo male I have a friend whos son is so sexy twink body type at the time he was 17 now 18. I took him shooting and had his ass in my crotch for a few moments. anyway I went to their apartment to swim with them and I couldnt keep my eyes off him. I bring up girls around him and he has no interest it seems. I had the chance to try and kiss him when we were changing and I chickened out. I want him so bad.

[Slanted]

Ive probably missed out on more opportunities with women that Ive been successful. After thinking about it the time I regret the most would have been my first time with a guy.

[DuzCuz]

There were a few times I wonder about why I didn't fuck them when I had the chance. But I have pretty much had the attitude that things happen (and don't happen)for a reason. I have always been pretty careless about cumming inside the pussies I fuck. So far, I knew about all my kids when they were growing inside their mothers. No surprises have shown up at my door, yet. I have to figure that those times would have ended up being a surprise, probably at the worst possible time. A couple were married and the surprise could have been an irate husband with a 12 ga.

[muhabba]

I'm one of those guys that need, basically, a direct statement of intent before I figure out what's going on. Last one was me and this girl and she was drunk but I wasn't. So we start making out on the floor and she's naked. She tells me that she's ready for bed so I take her to her room and tuck her in and give her a kiss good night and leave. It wasn't until 2 hours later that it hit me, "She meant ready for bed with me!". I am an idot.