opportunities lost or missed

[muycurioso]

some of the things I didn't say yes to. repressed and rigid. or maybe they asked at the wrong time. by assorted girl friends at different times
1. get dropped off at gay bar and have to find ride home.
2. get dressed and dolled up
3. get pegged.
4. kiss my guy friend with women present playing strip poker

2 and 3 were from the same gf

 

[Always5]

Rimming a friend that let me blow him several times, I wish I had taken the chance. He also wanted me to cum on his ass and lick it off. I was so happy sucking him and licking his balls I just did that. He had the nicest smoothest ass too.

 

[CuriousTxGuy]

missed

Opened a door and saw one guy on his knees, another with his pants down around his ankles getting blown. The guy feeding that mouth looked my way with fear and surprise. I quickly shut the door.

That was soooo wrong. I should have grabbed my package and invited myself in on the party.

 

[GentlemanJedi63]

My missed opportunity

Several years ago, when Craigslist still had a personals section, I posted an ad looking for an older man (60+) to guide me into gay sex. A very nice, single, and gay man of about 62 answered my ad, and began his seduction. Because of traveling for work, but mainly from my own fear, I wasn't able to go through with his introduction into the forbidden, but sinfully pleasurable world of man sex.

 

[gurlsynthia]

Missed opportunity?

It seems that I might have missed that opportunity back in high school. A friend and I shared a table in what we used to call study hall. There was also a girl at the table with us. My friend kept telling me how good it felt to jerk off and that I should try it. I was embarrassed because I am sure the girl heard everything and I didn't want to talk about it in front of her. But, I had not yet experienced that pleasure and so I listened intently, so was the girl I think. I am not sure now whether he was suggesting that we get together for some stroking or just trying to get me to say I tried it, so as to embarrass in front of the girl. Guess I will never know, but I after reading all your posts, I really wish he had been more private about it and we had made arrangements to get together.

 

[curiousdude0023]

One time I was in our local Target and had a near encounter with a handsome Hispanic man. He was probably near 40 and I was in my mid 20s. At this point, I had some curiosity about being with a man, but hadn’t followed up on it or had even thought about it much more than some curious porn watching.

I was watching looking at some DVDs and he came up and made some small talk. After talking about movies, jobs, etc. he told me how great it was that I was a teacher and that he had such an admiration of that and that I had to be strong to do that job. I brushed it off and said it goes with the territory. He put his hand on my shoulder, gave me a suggestive stare, and said we should get a drink and he could see some of that strength. I panicked and left, but man if that had been just a couple years later I would’ve had him teach me a thing or two that I could have used!

Definitely the material for a lot of hot jerk sessions, though.

 

[Ilovesilkthongs]

Adult store

I was visiting a new city on a work trip and I found a local adult book shop with video booths. I was in the store section looking at different panties and sissy clothes. There was a large man working the register watching me intently. A sexy woman came in and started talking to the guy at the register. They were both watching me now. The woman kindly spoke up and said “the pink ones are more your color.” I was so embarrassed but turned on. I said thank you and proceeded to purchase the pink panty and bra set she recommended. I also bought some coins for the booth.

I wish I would have engaged her more. I wonder what they were talking about.

 

[Hitchiker69]

Visiting Auckland, NZ and I had a night to myself. Hadn't had a cock in my mouth or ass for months, and I thought I'd try a local gay bar. Bought myself a beer, got chatted up by some guys at the next table. They realized I was an American, and asked if I knew I was in a gay bar. I said yes, I am bisexual, and thought maybe I'd get lucky. Nobody came on to me directly until closing time. One of the guys said "I fancy you" I had never heard that before, and didn't know what he meant.
Now I know he wanted to have sex.
Could have had some good man/man sex that night, if only I'd known!

 

[Hitchiker69]

In Isla Vista, California I met an older guy, late at night in the park. He asked if I had a place to stay. When I said no he offered that I stay in his place, a studio apartment. I said yes. On the way he told me he was gay and wanted to suck my cock. I was OK with that so we got undressed as soon as we got there.
He was stroking my cock as I enjoyed running my hands through his thick chest hair. Soon he started sucking and rimming me. I was loving it.
AS we squirmed and writhed around each other, both of us hard and naked, he positioned his ass over my cock and started to moved down onto my cock.
It was the first time I fucked a guy and I loved it.
I spent the night and we fucked like minks.
In the morning he took me to breakfast, then dropped me at an on ramp. He gave me his card, and told me to call anytime I wanted him.
I felt awkward about the night before, so I burnt his card and never saw him again.
I ended up living just a few miles away, for several months. Who knows how much sex we could have had/

 

[Hitchiker69]

Did I miss a gay 3 way?

In Sydney I had been cruising Fitzroy Gardens on a weekend night, a well known gay cruising spot. Got lucky, met a guy and went back to his studio flat. Hours of talking and drinking wine, but neither of us made a move. I definitely wanted his cock, so without saying a word I took off all my clothes, got in his bed and started to stroke myself. He soon joined me and we had a great night of sucking, 69'ing and fucking.
I wanted to spend the night, but he said no, come back next Friday at 9 p.m. He had some friends he wanted to introduce me to.
I chickened out, never came back.
Could have been a nice 3 way gay night, orgy or more. I'll never know.

 

[Hitchiker69]

Fitzroy Gardens is an obvious gay cruising spot. I met an older fat guy there one night. Normally I might not have gone back to his place, but he clearly wanted me, and I was very horny. His apartment was very small. We sat in the kitchen and talked for a long time. He said he wanted to show me the view from his bedroom. I stripped out of my clothes, and he did, too. WE got in bed and I fucked his ass while enjoying the view over downtown.
Afterwards he said he'd loved my fucking, and wanted to see me again. I said no, but he begged me. I never saw him again.
I could have explored all my fantasies about older men. My first real gay sex was with older fat guys. He would have done anything for me.

 

[tristantrotsky]

Lost School Opportunity

It seems that I might have missed that opportunity back in high school. A friend and I shared a table in what we used to call study hall. There was also a girl at the table with us. My friend kept telling me how good it felt to jerk off and that I should try it. I was embarrassed because I am sure the girl heard everything and I didn't want to talk about it in front of her. But, I had not yet experienced that pleasure and so I listened intently, so was the girl I think. I am not sure now whether he was suggesting that we get together for some stroking or just trying to get me to say I tried it, so as to embarrass in front of the girl. Guess I will never know, but I after reading all your posts, I really wish he had been more private about it and we had made arrangements to get together.

This confession seems rather mild compared to some of the others here, but it has bothered me for a long time. When I was in the School Showers after games an auburn-haired boy in my class reached out and got hold of my cock. I looked up at his face and he was smiling hopefully. He wasn't a friend, I don't think I'd even ever spoken half-a-dozen words to him before that moment. But here we were, both naked in the showers, and he was holding my cock gently. Perhaps he'd glimpsed, or maybe he'd heard that I was sexually experimenting with my friend John? I don't know. I was not offended, just surprised. I should have reached out and taken his cock into my hand, and we could have contentedly jacked each other. It might have led to more... to a friendship, with sexual benefits. It might have. But I simply pushed his hand away. Afterwards, I regretted it, but then it was too late...

 

[saintcero]

opportunity?

I was on a business trip with a coworker. We had just finished dinner at the hotel and were talking shop talk and having a beer when I was asked if I wanted to go to his room. I declined but have always wondered what he had in mind for the rest of the night. He is still around the area. I may ask him if I can figure out how to bring the subject up in conversation.

 

[oneblueye]

hey ...

It seems that I might have missed that opportunity back in high school. A friend and I shared a table in what we used to call study hall. There was also a girl at the table with us. My friend kept telling me how good it felt to jerk off and that I should try it. I was embarrassed because I am sure the girl heard everything and I didn't want to talk about it in front of her. But, I had not yet experienced that pleasure and so I listened intently, so was the girl I think. I am not sure now whether he was suggesting that we get together for some stroking or just trying to get me to say I tried it, so as to embarrass in front of the girl. Guess I will never know, but I after reading all your posts, I really wish he had been more private about it and we had made arrangements to get together.

Sounds to me like he was trying to gauge the girls reaction to the subject matter and draw her into a "why don't we try a--" situation.

 

[PleasePeesMe]

When I was fifteen, the boy I sat next to in French class and I used to feel each other's cocks, fingers inside our shorts. Looking back, one or two of the nearby boys must've noticed, but no-one said anything and we never took it further. I hadn't fucked a girl at this stage. If I'd sucked him before I tasted a cunt, who knows what may have transpired?

 

[2wayroad]

Back in my younger days, when I had not yet come to fully accept who I am, a buddy of mine and I were at a bar. Women were scarce as it was a slow night. Talk about sexual exploits led to frustration. Eventually it wasn’t worth hanging around anymore and we decided to leave. On the way out he invites me over to watch TV and drink a beer. Thinking nothing of it, I follow him to his place and we relax. He’s where I missed several hints.

We’re watch TV and laughing, having finished a beer and he excuses himself to take a shower (hint 1). After he walks out in only underwear, drying his wet hair with a towel (hint 2). Then he asks if I want to use the shower (hint 3). Now I’m nervous because I think I know what’s happening, but I’m not sure and don’t want to cross a line and ruin a friendship or become outed. Especially when I was still figuring out and wrestling with who I was. He never pushed anything or even made a move, just put enough out there without making it obvious. I didn’t shower or react to him and we hung out for awhile longer. I decided it was time to go home and get to bed. As I was about to leave he offered to let me sleep there (hint 4). I declined.

I went home confused and frustrated. I wondered if I was putting out a vibe or if I had read it all wrong. I was wishing that I’d taken that shower and stayed and at the same time glad I didn’t. I couldn’t have dealt with the possibility of rumors at that time in my life. Once home, I got out my dildo, fucked my ass while I jacked off and all my frustration temporarily left my body. But, I knew the day was coming when a dildo would no longer satisfy me.

Looking back, If given the opportunity again, I would have taken the chance.

There was another more subtle time in high school. Maybe I’ll make a post on that later.

 

[muycurioso]

a few more

I was active duty USMC. I met a couple through a mutual civilian female friend. we had fun all day. he and I hit it off, he was Navy. Anyway, later, I said how cool they were and my friend that was a girl said they are not a couple, they are both gay and he wants to go out with you. She then said she told him I would say no sone don ask hIm. he was good looking, who knows what I would have said. this was before don't ask don't tell. I think I know why she said that.

the other, again hanging out with mixed people and this guy knew unless I went home with a woman, I'd be stranded he kept telling me he had a couch I could crash on. I thought he might be gay. I was interested but also scared of AIDS and getting accused of being gay by the USMC. This was before don't ask don't tell. I slept alone, outside that night. I did that a lot in California

 

[bobb_sledd]

In the early 80's I was in the Marine Corps stationed in Hawaii. One morning I was walking off base to the bus stop to head to Waikiki for the day. A guy driving a convertible stopped and asked if I wanted a ride. (Not uncommon.) After I got in he asked where I was going. When I told him I was heading to the bus stop then down town he said he was heading that way himself. He asked if it was okay to take the longer more scenic route; I agreed. Turns out he was a Navy medical officer stationed on base. During the conversation that ensued there was little doubt in my mind that he was hitting on me. I wasn't offended, but at the time I wasn't really interested either. It's wasn't the first nor would it be the last time I was hit on during that tour in Hawaii (or since).

 

[Samday]

Where

This confession seems rather mild compared to some of the others here, but it has bothered me for a long time. When I was in the School Showers after games an auburn-haired boy in my class reached out and got hold of my cock. I looked up at his face and he was smiling hopefully. He wasn't a friend, I don't think I'd even ever spoken half-a-dozen words to him before that moment. But here we were, both naked in the showers, and he was holding my cock gently. Perhaps he'd glimpsed, or maybe he'd heard that I was sexually experimenting with my friend John? I don't know. I was not offended, just surprised. I should have reached out and taken his cock into my hand, and we could have contentedly jacked each other. It might have led to more... to a friendship, with sexual benefits. It might have. But I simply pushed his hand away. Afterwards, I regretted it, but then it was too late...

Where did you go to school?

 

[gurlsynthia]

Sounds to me like he was trying to gauge the girls reaction to the subject matter and draw her into a "why don't we try a--" situation.

I was very naive and very very inexperienced as to sex with anyone even Mrs Hand and her daughters, so i missed that idea completely. This thread made me look back for any other missed opportunities and another did come to mind. This should have been the first I remembered, because there was no question as to what he had in mind. I was working that summer for a delivery company and my first week was a getting to know the ropes apprentice situation. Anyway on a return trip from a delivery the older guy driving was chatting me up and all of a sudden asked me if he could pull the van over to the side of the road and suck my dick. I stammered out a no with some feeble excuse to both his first and second request and finally he dropped it. If only only he had persisted with better and stronger arguments, I might have finally relented. I certainly now wish I had given in. Many of you might think how could he have not mentioned this first, but I had repressed this deep until this thread made me remember it.

 

[tristantrotsky]

We Meet Again...

Where did you go to school?

In your erotic imagination...
Why, did you attend the same school? Oh Gosh! Was it you in the school-shower...? In which case may I take this opportunity to apologise for my poor response...?

 

[muycurioso]

you got that right

In the early 80's I was in the Marine Corps stationed in Hawaii. One morning I was walking off base to the bus stop to head to Waikiki for the day. A guy driving a convertible stopped and asked if I wanted a ride. (Not uncommon.) After I got in he asked where I was going. When I told him I was heading to the bus stop then down town he said he was heading that way himself. He asked if it was okay to take the longer more scenic route; I agreed. Turns out he was a Navy medical officer stationed on base. During the conversation that ensued there was little doubt in my mind that he was hitting on me. I wasn't offended, but at the time I wasn't really interested either. It's wasn't the first nor would it be the last time I was hit on during that tour in Hawaii (or since).

being young, in shape, every weekend I get hit on by guys. I did feel that I was always being watched so I always said no. a few were good looking guys. one time I was on the bus and a guy got off and then jumped right back on staring at me. I didn't say anything and he got off.

 

[Barbelle]

Pretty tame compared to some but here's mine. Staying the night at a friend's place, sharing her queen-sized bed and reached down to adjust the electric blanket. I feel her hand caress my back (!). In some weird flurry of insecurity or plain dumbass naivety, I mentally excused it as her "having a dream about her boyfriend". I wish I'd just let myself see where it went.

 

[Hitchiker69]

missed opportunities, gay and straight

Too many to count...

As I look back over the years since I became sexually aware there have been dozens,
maybe hundreds of opportunities and propositions that I've missed. Both gay and straight.

Examples:

From High School days, when more experienced girls wanted me, but I wasn't ready, felt intimidated,
and as a result couldn't get it up when she was hot and ready. Could have gotten a good fuck with a more
experienced young woman. This happened more than once.

Another example: On Venice Beach on a summer afternoon. I was in my teens. I was stoned, enjoying the sun, smiling
at everyone and anything. An older gay guy noticed me, hit on me, but I was uncomfortable and I left.
Could have gotten a blow job at least.

In my early 20's I was propositioned by my gay boss. He was much older and had a skin condition...pre Aids days. He would have given me blow jobs regularly

Fast forward to the early 80's. I had an office job at a large corporation; my first time working around women.
I was 30 something, very fit and recently single (divorced). I dated a bit, nailed a few, and got a reputation.
Next thing I know women are available at every turn. They came on to me in several ways. Several propositioned me,
but I didn't follow through since I had feelings for some of the girls I already established sexual relationships with.

They came on with complaints like "my husband hasn't touched my ass in two years, I need a man"
"I've separated from my husband, I need a man, and I like tall thin men like you"...this from my boss.

At one point I was fucking 1 or 2 a week, and turning away another 1 or 2 a week.

And there are many more.

 

[klippert]

Missed opportunities; from the locker rooms to men’s rooms.