Missed Opportunities

[OdinElder]

As I look back over my life I realize there several times I had a chance to have an adventure but didn’t realize it at the time. A couple of examples:
In college a buddy and I went to an adult theater and watched the movie. Afterwords we went back to his apartment and browsed his collection of porn magazines, with him sitting very close to me on the couch. I look back now and wonder if he was trying to start some play.

Or the time I was dating an adventurous girl who kept talking about her older black coworker that was always dropping hints to her. If that were now I’d tell her to invite him over so I could watch him fuck her and then clean them up when they were done. But I was too naive and slow to take a hint.

What were your missed opportunities?

 

[Kitty_so_frisky]

EDIT: I just realized this thread was posted in the LGBTQ+ Chatter section. I came across it in the New Posts page and replied without realizing that. Apologies, wasn’t my intention to step on your thread!

——original post——

I was friends with these twins for several years. Twin 1 and I made out several times one day, and like a year later, he sucked my nipples on an airplane, without disclosing he had a girlfriend at the time. T2 and I actually dated for a while about a year and a half after that. One day, the 3 of us were hanging out at my place. T2, who I was with at the time, was lounging on the floor in front of the TV, with his back to the couch where T1 and I were sitting. T1 started trying to grope me and kiss my neck. I got mad and pushed him away and told T2, and asked if he was going to do anything about his twin. T2 kinda shrugged it off, which made me get mad and kick them both out.

It didn’t occur to me until yeeeears later that maybe the reason T2 didn’t get upset with T1 is that they came over with the intention of seducing me into a threesome. Stupid, stupid me! They were really cute and we had great chemistry too.

I did end up having sex with T1 another year or two after that…aaand spent another afternoon making out with T2 a couple years after that…until he told me he had a pregnant fiancé. Aaand then he told me he loved me a couple months later, while he still had that pregnant fiancé. They were cute, but messy AF!

 

[Elle4u2use]

I regret not having sex with a pair of bros when offered

I regret not fondling a lesbian when I slept in her hotel bed instead of mine

I regret not letting a lesbian trib me when asked

 

[carlg111901]

I was at a party at a coworkers house who was openly gay. Most of the people had left, except a small number of coworkers. My coworkers left to get more beer, I stayed back to hang with our gay coworker. As they pulled away, he said to me "we have about 15 minutes, let's go to my room and fool around." I laughed it off and reminded him that I wasn't gay, or into guys; and he said, "oh well, your loss." He did have a big mouth and bragged about some of the other "straight" coworkers he had fooled around with, so I don't regret turning his offer down. That said, that was the one and only time any of my friends had offered anything like that to me. If he wasn't a loud mouth, I probably would've taken him up on his offer and I would've sucked my first cock years before I actually did. I also regret not hanging with the "straight" coworkers he bragged about swapping head with. But they all quit after he spilled the beans to all of us.

 

[Hitchiker69]

So many missed opportunities I can hardly remember them all. I'll list a few
1) I had a roommate who was openly Bi. He would often hit on me when we were alone, by asking "How are you and Mary getting along?" Obvious that he'd suck me if I wanted
2) Other young hitchhiker I met on the road, who suggested we should 'practice' for the drivers who'd pick us up and want sex
3) Other hitchhiker who I traveled with for a week. He propositioned me when we slept in a shed
4) Guy who followed me home, then grabbed his crotch when he saw me in my apartment window
5) My gay boss at a restaurant, who invited me upstairs to his apartment after work
6) Guy I met at a crafts fair, who was sleeping in his car. We were both attracted, I could have invited him to stay in my motel room, and do some serious m/m fun sex
7) young guy at my pharmacy, who gets flushed and starts breathing heavy whenever I come in for a re-fill
8) Jay, the prettiest man I ever met. Our mutual attraction was obvious to all. We could have had a wonderful gay affair
9) Young John the runaway I met. I knew he was BI, but I didn't realize he was hot for me until he moved away
10) The old fat guy I picked up at a gay cruise park. We went back to his place and I fucked his ass. He begged me to stay, or to see him again, but I said no. I could have left my options open. We could have played out a lot of fantasies, since he reminded me of my first gay lover

... and many more

 

[1960curious]

When I was 19-20 I was in the back seat of the car with 2 other guys, we were going home from a party. We had been drinking, I layed my head back and closed my eyes. I felt a hand on my leg, it felt pretty good, my cock started growing. I opened my eyes a little to see what and who was going on. Just then the other guy started rubbing my cock. It felt so good. He un zipped my pants and pulled my cock out. One guy held my cock and the other guy started sucking me! OMG it was so good, but I had never been with a guy before and didn't think I should be, since I had a girlfriend and like women!
I jumped and told the driver to stop the car and let me out!
I got out and ran home.
Now I would love for that to happen again, I would be sucking their cocks too!
I relized after I got older that I am bi and love sex with men and women!

 

[BiDrew42]

My missed opportunities were all during the time when I was married.

1. I had an openly gay coworker who hit on me for almost the entire time I was married. I was flattered (he was just my type and I fantasized about him endlessly) but I never took him up on any of his many offers. I never did ask him how he knew I was interested but he surely did. Unfortunately, he passed away shortly before my divorce was final.
2. I travelled a lot for business and had opportunities with males and females that I never took advantage of.
3. Went to a strip club once that featured a trans porn star as the headline act. She was sexy, gorgeous, very feminine, and had a lovely big cock. I was right next to the stage and she singled me out for some special attention, shaking her cock and ass in my face during the course of her act. Afterwards, while she was mingling with the crowd and collecting tips, she gave me her card and told me to call her if I wanted a private show. I wanted to but didn't, and regret it to this day.
4. Went to a couple of drag shows in New Orleans with a colleague who worked in our San Francisco office. Back at our hotel, I accompanied him to his room for a nightcap, where he quickly got physical. I pushed him away and left. Back in my room I regretted not having sex with him and masturbated while fantasizing about him. Sadly, our relationship was no longer the same after I rejected him and I didn't get another opportunity.
5. One of my wife's cousins lived near us after her divorce. I had been fantasizing about her since the first time we met, and even tried to convince my wife to have a foursome with her cousin and her husband. I would occasionally go over to the cousin's house to help her with some projects. Once I was installing a glass door on her shower. When I finished I called for her to come and have a look. She came into the bathroom wearing nothing but a pair of sheer black panties and she looked incredible. She invited me to shower with her and began to slip her panties off but I stopped her and told her I had to go. By the time I got divorced several years later she was remarried and I kick myself in the ass every time I think about that missed opportunity.

Never cheated on my wife during almost 20 years of marriage. Missed a shitload of opportunities.

 

[Lighthousenorth]

I was on holiday and stayed in a hotel. On a gay chat I saw a call for a man who wanted to pose naked for an outdoor photoshoot. The photographer lived less than a kilometer from the hotel. He told me where he would meet me. I walked to that place but no one showed up. After a few minutes I walked back to the hotel and then saw a guy with a camera jumping on his bicycle. I had been just a short distance from the place he was. And I had forgotten to ask his phone number. How stupid.

Later I saw him again in the chat room and apologized for what went wrong. He said it often happens that no one shows up. I had already travelled to the next destination, so there was no second chance. How clumsy.

 

[BlueEyes1969]

I met a hung guy at a gay nudist resort in the steam room. We sucked each other off while sweating buckets in the heat. When we had devoured each other we went out to the cold outdoors shower and lathered each other up and kissed while the water ran over us. We toweled off and sat by the pool and snoozed for about an hour. He invited me to come home with him that evening for a light dinner and whatever we wanted to do after. I had a room at the resort and had made a date with another guy I met in the playroom, and so I turned down the invitation. He was clearly disappointed and left the resort. I had a light supper on my own and returned to my room to await my date. He was a no show. I went out to the pool and spa and ended up in the play room for some play with a number of anonymous, horny men.
I have always regretted not accepting that invitation and for not exchanging contact info. Never saw him again . . . .

 

[desire30]

As I look back over my life I realize there several times I had a chance to have an adventure but didn’t realize it at the time. A couple of examples:
In college a buddy and I went to an adult theater and watched the movie. Afterwords we went back to his apartment and browsed his collection of porn magazines, with him sitting very close to me on the couch. I look back now and wonder if he was trying to start some play.

Or the time I was dating an adventurous girl who kept talking about her older black coworker that was always dropping hints to her. If that were now I’d tell her to invite him over so I could watch him fuck her and then clean them up when they were done. But I was too naive and slow to take a hint.

What were your missed opportunities?

 

[roseburgsteve]

As I look back over my life I realize there several times I had a chance to have an adventure but didn’t realize it at the time. A couple of examples:
In college a buddy and I went to an adult theater and watched the movie. Afterwords we went back to his apartment and browsed his collection of porn magazines, with him sitting very close to me on the couch. I look back now and wonder if he was trying to start some play.

Or the time I was dating an adventurous girl who kept talking about her older black coworker that was always dropping hints to her. If that were now I’d tell her to invite him over so I could watch him fuck her and then clean them up when they were done. But I was too naive and slow to take a hint.

What were your missed opportunities?

One of my missed opportunities was I was 18 years old working in a hotel as a night janitor. I was in the middle of cleaning the banquet room I had the doors open and some music going. I looked over at a guy standing at the door looking at me and sucking his thumb every once in a while. I went over and shut the door. Then a little later I went up to the third floor to get some supplies. As I walked back to the elevator to go back down there was the same guy stand with another guy in their room with the door open. They both looked at me and the one guy I had seen before asked if I wanted a blow job from both of them. I was shocked and speechless. I got on the elevator and put it out if my mind. At that time I was bi curious. And I still kick myself for not taking them up on the offer. I will always wonder what could have happened if I went in that room. I will always wonder could I have explored my sexuality a lot sooner.

 

[SPARTAN047]

I think I've got too many of them, but some were due to me not being interested enough, distance, rude people, and some (especially women when I thought I was straight/bi) being too demanding with arrangements, expecting gang bangs only, or probably trolls posting just for attention with no intent to meet up.

 

[Hitchiker69]

I lived in a very gay neighborhood of Sydney, which is a very gay friendly city. People there just assumed all young men were Bi or gay. There were 2 gay bars within a block of my apartment, and a gay cruise park near by. I could have sucked cock almost any and every night of the week if I wanted some.
I did have gay sex about every 6 months but I could have had so much more. Problem was I felt shame after each gay encounter, and I sought out sex with women to re-establish my identity as a 'straight' man who just needed some cock to suck once in a while
Opportunities were all around me.

 

[GECuck]

What a great thread. I have many, that I still think about, but need to collect my thoughts so I can do them justice!

 

[Baddad2004]

A month ago I was at a truck stop buying seltzers. I was in flip flops and my toe nails were painted. I go do this monthly with my wife I don’t think it weird. When I was checking out I had an older trucker gentleman make a pass at me.

 

[GECuck]

Here’s one Ive shared before but right on point here. In high school, I was on a cruise and was in the sauna. I was by myself until this older (40?) guy came in. He was European and was naked so I tried not to think much of it. Until he got hard…he was watching me and stroking himself. I left before he came, but thinking back I wish I would have stuck around!

 

[Biman1120]

The one that sticks out in my mind was when i was with a group of friends visiting another friend. I was in my late teens (18 or 19 at the time). Early 20's guy who lived near the friend we were visiting was coming onto me big time, even naive me saw it instantly when he said he gave great anal while eyeballing my ass.
Later heard that rumor was he had a 10 or 11incher and was as good as he claimed.
Was worried bout my image with my friends but really wanted to take him up on his offer but didnt. Probably for the better but who can know for sure lol.