I was close friends with a (male/female) couple in my early twenties… call them Adam and Eve. Things started getting interesting when we all went skinny dipping together and then they fucked while i watched and masturbated. After that I watched them several times and sometimes Eve would instruct the two of us to masturbate for her before they had sex. Well, at a small party one time we all started getting a little drunk and Eve dared Adam and I to strip naked and run out into the front yard. We did of course - and the others locked us out. After a bit we realized we could get in thru the back door and Adam suggested “we should stroke our cocks so when we burst in on them our erections are waving around.” Which we did and hilarity ensued. But I always wonder what would have happened if I offered to help him get hard. Maybe with my hand… maybe my mouth. Would the others have looked out and seen me stroking his cock or, even better, on my knees. Eve was pretty wild, I like to think she would have invited me to join them and she and I could have spent the night pleasuring him.
For the Guys: Topic - "I wish I had <unfulfilled desire or missed chance goes here>"
- Thread starter Milo9012
- Start date
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
Those two guys should maybe have used one of the cubicles to provide the privacy to enjoy a good blowjob, like the rest of us do...
cdstefi
Lingerie addict
- Joined
- Dec 26, 2021
- Posts
- 2,816
IWIH...
Taken the initiative one evening when Fay, a housemate's girlfriend and I got stoned listening to my impeccably curated and cool small record collection (I have no idea where he was but they were kinda on the way to breaking up so he was probably out with the lads and trying to pull).
I was still a virgin at this point so incredibly shy about being with a sexy girl, particularly one I'd heard fucking many a time (she was a loud one). We were very relaxed and stoned and I think if I'd had the nerve I would have kissed her and then maybe gone on to something more, but faint heart failed to win fair maiden on this occasion and the chance never occurred again because she went on to go out with another mate of mine.
Taken the initiative one evening when Fay, a housemate's girlfriend and I got stoned listening to my impeccably curated and cool small record collection (I have no idea where he was but they were kinda on the way to breaking up so he was probably out with the lads and trying to pull).
I was still a virgin at this point so incredibly shy about being with a sexy girl, particularly one I'd heard fucking many a time (she was a loud one). We were very relaxed and stoned and I think if I'd had the nerve I would have kissed her and then maybe gone on to something more, but faint heart failed to win fair maiden on this occasion and the chance never occurred again because she went on to go out with another mate of mine.
Hmm the question I have asked myself again and again, I had a guy we were together for a little over a year and he was the 1st and only guy I had any type of long term relationship with and back in the late 1970's gay/bi wasn't a good thing to be in an Italian Catholic family (me) and an Irish Catholic family (Brian). While he wasn't by far the 1st guy I was with but the others before him weren't anything of serious nature while he was, I had been on both ends of sucking cock and jerking off with others but with him it was more, the 1st guy I ever kissed, the 1st ass I rimmed, the 1st mouth that ever rimmed me, the 1st guy I ever fucked and lastly the 1st guy who ever fucked me.
The thing I missed out on was my fault was him wanting to live his life and came out while I was too afraid of the consequences and we parted ways, he went into the service and I into my journey to find what I wanted to do with my life workwise and then lost track of him. I was with many guys after and although I had sexual fun I never found someone I wanted to be with, I kind of seemingly compared my time with him and well nobody lived up to that. I married my wife whom I am still with who never knew of my past and never will as I would never upset her or end what we have. I have since wondered many many times what life would have been like had I continued with him and those thoughts clogged my mind when he one day out of the blue sent me a friend request on Facebook all these over 40+ years later. I honestly think if I had come out as gay before I finally realized I was in fact bi when I started dating girls I may have still considered myself gay and still have been with him, but alas only God knows the what ifs in life.
The thing I missed out on was my fault was him wanting to live his life and came out while I was too afraid of the consequences and we parted ways, he went into the service and I into my journey to find what I wanted to do with my life workwise and then lost track of him. I was with many guys after and although I had sexual fun I never found someone I wanted to be with, I kind of seemingly compared my time with him and well nobody lived up to that. I married my wife whom I am still with who never knew of my past and never will as I would never upset her or end what we have. I have since wondered many many times what life would have been like had I continued with him and those thoughts clogged my mind when he one day out of the blue sent me a friend request on Facebook all these over 40+ years later. I honestly think if I had come out as gay before I finally realized I was in fact bi when I started dating girls I may have still considered myself gay and still have been with him, but alas only God knows the what ifs in life.
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
Yes... but on the upside of the equation, you might have got your cock sucked!
Bathtubbill
Literotica Guru
- Joined
- Nov 4, 2020
- Posts
- 902
Unfortunately I will never know
Opportunity missed
It took a long time to get round to it
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
Regret for missed opportunities is a terrible thing, those teasing possibilities will always gnaw away at your mind. And getting your cock sucked is the kind of bliss you don't want to miss out on.
Curiousewa
Virgin
- Joined
- Nov 10, 2023
- Posts
- 37
I wish I had said yes to the guy I met on a business trip. We were both in the hotel hot tub and he struck up a conversation. Seems we had a lot in common and hit it off. He climbed up on to the edge directly across from me. His shorts were loose around his legs. He spread his legs so I was looking directly at his cock which was starting to harden. I was fascinated with it and couldn't look away. He was looking right at me and was apparently pleased with my reaction. He then told me that he had a great bottle of bourbon in his room and invited me to come share it with him. I didn't and still don't want to cheat on my wife so I politely declined. In some ways, I still regret that.
dobbins1
Really Experienced
- Joined
- Aug 21, 2013
- Posts
- 446
At 66, looking back, there were too many "missed opportunities" that I could've experienced. Especially after I got married. I was in the foodservice industry surrounded by women. All I can say, I was an idiot!! I was only 23 and many of the girls/women were anywhere from 18 to 35. Prime real-estate. But alas, didn't have the balls to pursue.
SexyInMy60s
Back Again
- Joined
- Jul 9, 2023
- Posts
- 196
I’m an alcoholic and, happily, I’ve now been sober 15 years. I regret many things about my drinking days, including hooking up randomly with guys while I was traveling on business. It was all too easy to log onto Craigslist and find a guy to come to my hotel room and play. There were a few fun times but many bad decisions and unpleasant experiences fueled by booze.
After I somewhat miraculously quit drinking, I remarried and eschewed guys for a long time. But I began to have the itch again a few years ago during the pandemic. I wondered what it would be like to be with a guy while I was sober and in the moment.
I wrote a little fantasy story for Lit about a dream threesome with a real gay couple in my neighborhood. Between the nice feedback about that tale and my lingering interest in being submissive and bottoming for the right guy, I decided erase some of those regrets and have one last fling with bisexuality.
I came up with a sort of bucket list of kinky shit I wanted to try again while sober and fully able to appreciate the moment. There were basically three things I wanted: give and get and few really good blowjobs; enjoy a threesome and hopefully be the center of attention in a spit roast; and, top of the list, find a daddy type with a big dick who would really fuck the daylights out of me.
The idea was to complete my bucket list and replace some bad old memories with good newer ones. Why? Because life is too short to be consumed with regret.
So for the past year or so, I’ve been on something of a quest to fully and finally explore my sexuality and close the loop by writing the story - warts and all - for Lit. It’s coming soon.
So, in the spirit of this thread, I wish I had been less of a drunken asshole back in the day but now I’ve done something to replace that regret with some very sexy memories.
P.S. - here’s that fantasy story I wrote that sort of rekindled my interest: https://www.literotica.com/s/neighborly-7. Enjoy!
After I somewhat miraculously quit drinking, I remarried and eschewed guys for a long time. But I began to have the itch again a few years ago during the pandemic. I wondered what it would be like to be with a guy while I was sober and in the moment.
I wrote a little fantasy story for Lit about a dream threesome with a real gay couple in my neighborhood. Between the nice feedback about that tale and my lingering interest in being submissive and bottoming for the right guy, I decided erase some of those regrets and have one last fling with bisexuality.
I came up with a sort of bucket list of kinky shit I wanted to try again while sober and fully able to appreciate the moment. There were basically three things I wanted: give and get and few really good blowjobs; enjoy a threesome and hopefully be the center of attention in a spit roast; and, top of the list, find a daddy type with a big dick who would really fuck the daylights out of me.
The idea was to complete my bucket list and replace some bad old memories with good newer ones. Why? Because life is too short to be consumed with regret.
So for the past year or so, I’ve been on something of a quest to fully and finally explore my sexuality and close the loop by writing the story - warts and all - for Lit. It’s coming soon.
So, in the spirit of this thread, I wish I had been less of a drunken asshole back in the day but now I’ve done something to replace that regret with some very sexy memories.
P.S. - here’s that fantasy story I wrote that sort of rekindled my interest: https://www.literotica.com/s/neighborly-7. Enjoy!
That’s an incredible story and it really turned me on!
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
And no man in his right senses turns down the offer of a no-strings blowjob!
I totally agree, but I did have a couple of guys that turned me down before. They were all bent out of shape like I was asking them to suck my cock!
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
Some guys are just totally messed-up by a religious upbringing or by societal pressures that they are unable to simply enjoy the sensual pleasures of having their cocks sucked by a willing and hungry mouth. That is their tragedy.
Milo9012
Literotica Guru
- Joined
- Nov 18, 2017
- Posts
- 1,328
They might have been turned on by the offer but their adventurous spirit and fragile manhood were likely low, and likely regret it now.
It's weird how some guys react so angrily at the idea of being offered the discreet gift of something as simple and pleasurable as a NSA quickie
BJ.I don't know how to read the signs between those who Will accept and those who Won't, and since I try to avoid brawls, I don't offer. But I have been so tempted at times.
JoeSmith2022
Really Really Experienced
- Joined
- Nov 10, 2022
- Posts
- 440
The first guy I ever sucked off... I wish I had let him fuck me. I'll always regret that.
JoeSmith2022
Really Really Experienced
- Joined
- Nov 10, 2022
- Posts
- 440
That guy had a HUGE cock, and I should have gone for it.
In the part of the country where I live and especially back in those days, no guy would ever let anyone know they had any desire to have any form of gay sex. I was the same, I would never let anyone know that I had thoughts of sucking cock unless I was half drunk, then I would do about any thing.They might have been turned on by the offer but their adventurous spirit and fragile manhood were likely low, and likely regret it now.
It's weird how some guys react so angrily at the idea of being offered the discreet gift of something as simple and pleasurable as a NSA quickie
I don't know how to read the signs between those who Will accept and those who Won't, and since I try to avoid brawls, I don't offer. But I have been so tempted at times.
Astroman72
Really Experienced
- Joined
- Jun 27, 2015
- Posts
- 1,015
I've told my story here before, but I think I missed out on an ideal situation.
Way back in my 20s (early 90s), I had a coworker, Jim. We were the same age. We were both on the short side, although he was more thin and wiry and my build was more athletic. We became friends, and we were both pretty horny guys. We went to a strip club together a couple times, and also to a porn shop a couple times and bought magazines (just straight and lesbian.)
He had a girlfriend, and I didn't. He would joke around a lot, talking about how he had a pretty big cock, although I could tell he wasn't really joking. He said his younger brother was gay, and it was no big deal. He said that he'd show me a video sometime of his girlfriend giving him a blowjob.
Once, I got together with him and another friend of his, and that guy had said that he and Jim had watched a gay porn video some time ago, and how he thought it was gross. Jim smiled and agreed, but I got to thinking "well, ONE of them must have known they were renting a gay porn vid." One other time, Jim also joked (again, half-serious) that he and I should watch porn together sometime and jerk off. I jokingly said "Sure, that sounds good" and we both kind of laughed it off.
He left the job a little later, and we fell out of touch and nothing ever happened. Looking back on it now, I see that he gave me a lot of signs and I'm pretty sure he wanted me to suck his cock--or at the least he would have been open to it if I had suggested it. And I would have loved to give him a blowjob, and maybe more!
As others have mentioned, I remember at that age being so paranoid and worried about being perceived as gay, and I think it was the same for Jim, so neither of us made an explicit move. But it could have been an ideal situation, as we were both highly-sexed, mostly straight guys who would have kept things discreet.
Although maybe that's just a fantasy and he would have turned me down if I had made my interests more clear. You never know.
Way back in my 20s (early 90s), I had a coworker, Jim. We were the same age. We were both on the short side, although he was more thin and wiry and my build was more athletic. We became friends, and we were both pretty horny guys. We went to a strip club together a couple times, and also to a porn shop a couple times and bought magazines (just straight and lesbian.)
He had a girlfriend, and I didn't. He would joke around a lot, talking about how he had a pretty big cock, although I could tell he wasn't really joking. He said his younger brother was gay, and it was no big deal. He said that he'd show me a video sometime of his girlfriend giving him a blowjob.
Once, I got together with him and another friend of his, and that guy had said that he and Jim had watched a gay porn video some time ago, and how he thought it was gross. Jim smiled and agreed, but I got to thinking "well, ONE of them must have known they were renting a gay porn vid." One other time, Jim also joked (again, half-serious) that he and I should watch porn together sometime and jerk off. I jokingly said "Sure, that sounds good" and we both kind of laughed it off.
He left the job a little later, and we fell out of touch and nothing ever happened. Looking back on it now, I see that he gave me a lot of signs and I'm pretty sure he wanted me to suck his cock--or at the least he would have been open to it if I had suggested it. And I would have loved to give him a blowjob, and maybe more!
As others have mentioned, I remember at that age being so paranoid and worried about being perceived as gay, and I think it was the same for Jim, so neither of us made an explicit move. But it could have been an ideal situation, as we were both highly-sexed, mostly straight guys who would have kept things discreet.
Although maybe that's just a fantasy and he would have turned me down if I had made my interests more clear. You never know.
Astroman72
Really Experienced
- Joined
- Jun 27, 2015
- Posts
- 1,015
It's funny, I never drank until college, and by that time, I already had strong urges to suck guys' cocks. I had never really been around drunk people, and on TV and the movies people got drunk and lost all control. I remember being terrified that I was going to have one beer and then tell all my friends I wanted to suck them off!
Wow how old are you?
I wish I had anal sex before my prostate was removed. From what I understand the feeling of having your prostate stimulated is incredible and the orgasms are the strongest you will ever have. I think about every time I get pegged. But you can't turn back the clock and having it removed is better than being dead.
tristantrotsky
Literotica Guru
- Joined
- Jun 25, 2012
- Posts
- 9,556
Sucking their cocks is an even better way for friendships to get firmer...
spraybomb13
Really Experienced
- Joined
- May 1, 2004
- Posts
- 171
After I graduated and was waiting until I left for boot camp, I took a job at a grocery store regional bakery. The guy who was training me was a couple years older, and we had quickly become friends due to mutual interests.
I had been there about a month or so when he invited me over to his place after work. We were always talking about cars or music, so I followed him there when our shift was over.
His place was a small house that was on his family property and I remember thinking how cool that would be to have! We went inside and I sat on the couch. I've never been much of a drinker, but he offered me a wine cooler (this was back in 1992) and I accepted it. He sat down next to me and turned on MTV. We talked about the usual guy stuff as we drank. I had made it about halfway through my second one and was feeling good.
We started talking about girls and if we had girlfriends, which I didn't at the time. I remember he started saying how they were always ruining things and that I really didn't need one anyway. I was pretty naive at the time, I came from a small town with parents who sheltered me from a lot of things, so I wasn't following what he was trying to say...duh!
I finished my second wine cooler, and he went and got us a couple more. He asked if I liked watching "dirty movies", and I said that I guessed so, but by that time, I'm not sure if I had ever even seen one! He said he had a good one, and put in a tape in the VCR. VHS baby!
It started out like all pornos do, and was pretty cheesy, but I was pretty excited about seeing it. The girl in the movie was blonde, with long curly hair. Typical 80's style, which I STILL find super hot! I remember her denim mini skirt, and her lace topped white socks and black heels...and I still love those too!
The usual things that happens in porn began to happen, and it was causing the usual things to happen to my 18yr old body too.
I was super hard and was shifting around trying to get comfortable, lol. And that's about the time things got weird for me. The guy in the movie had pushed the girls skirt up to reveal her white thong from behind. He was kissing her cheeks and started pulling her panties off. She stepped out of them, and when she turned around, she had a dick! I had NEVER seen anything like this, and at the time, I don't think I knew there were people like this! The guy had started sucking her cock and I was freaked out, mesmerized, hard as a rock, and buzzing pretty good. My friend started saying things like, "See, you don't need a girlfriend" , "I'd love to do that.", and other stuff but I still hadn't caught on to what he was trying to REALLY say. I was almost hypnotized by what was going on in the movie. This was so new and different to me. I was turned on and somewhat ashamed that I was liking it. She was so hot, beautiful body, perfect breasts, lips, legs...and a cock. I couldn't take my eyes off of the TV! At some point, my friend got up and left the room, so I took the opportunity to rub myself through my pants. I wanted to touch myself so badly. I wanted some relief, I wanted to keep watching this movie!
When he came back into the room, he had changed into a T-shirt and shorts. Since we had come to his place right after work, I was still wearing my black work pants and collared shirt. He had brought me a pair of shorts to put on, but I was afraid he would see my hard-on if I got up to change! He said, "Go ahead and get comfortable ", so I slowly went to get up, and that's when things happened. As I went to get off the couch, he moved down and kissed me and grabbed my cock at the same time. I didn't know what to do. I wasn't gay, but it felt good and wrong at the same time. He started rubbing me through my pants, and asked if I "liked that"? I was a bit scared, and confused, and nervous and ready to cum in my pants!
I told him I didn't know and that I wasn't gay. He said that it was okay, we were just two friends helping each other out. I was rapidly sobering up, and began to panic a bit. I wasn't sure what was supposed to happen, why I was feeling certain things, and how was I supposed to get out of this situation.
I finally got up and said I had to go, and I would see him at work. He tried to apologize, and I said it was okay.
I left his place and went to my apartment. My roommate was at work, since I worked overnights. My mind was racing about what had happened. I had gone to bed, since I went in to work that night, but images of the movie were playing in my mind, and remembering him rubbing on me, I started to get hard. I began stroking myself to get some relief. What was really messing with me, was that while I was thinking about the movie and the hot blonde, I was fantasizing
I had been there about a month or so when he invited me over to his place after work. We were always talking about cars or music, so I followed him there when our shift was over.
His place was a small house that was on his family property and I remember thinking how cool that would be to have! We went inside and I sat on the couch. I've never been much of a drinker, but he offered me a wine cooler (this was back in 1992) and I accepted it. He sat down next to me and turned on MTV. We talked about the usual guy stuff as we drank. I had made it about halfway through my second one and was feeling good.
We started talking about girls and if we had girlfriends, which I didn't at the time. I remember he started saying how they were always ruining things and that I really didn't need one anyway. I was pretty naive at the time, I came from a small town with parents who sheltered me from a lot of things, so I wasn't following what he was trying to say...duh!
I finished my second wine cooler, and he went and got us a couple more. He asked if I liked watching "dirty movies", and I said that I guessed so, but by that time, I'm not sure if I had ever even seen one! He said he had a good one, and put in a tape in the VCR. VHS baby!
It started out like all pornos do, and was pretty cheesy, but I was pretty excited about seeing it. The girl in the movie was blonde, with long curly hair. Typical 80's style, which I STILL find super hot! I remember her denim mini skirt, and her lace topped white socks and black heels...and I still love those too!
The usual things that happens in porn began to happen, and it was causing the usual things to happen to my 18yr old body too.
I was super hard and was shifting around trying to get comfortable, lol. And that's about the time things got weird for me. The guy in the movie had pushed the girls skirt up to reveal her white thong from behind. He was kissing her cheeks and started pulling her panties off. She stepped out of them, and when she turned around, she had a dick! I had NEVER seen anything like this, and at the time, I don't think I knew there were people like this! The guy had started sucking her cock and I was freaked out, mesmerized, hard as a rock, and buzzing pretty good. My friend started saying things like, "See, you don't need a girlfriend" , "I'd love to do that.", and other stuff but I still hadn't caught on to what he was trying to REALLY say. I was almost hypnotized by what was going on in the movie. This was so new and different to me. I was turned on and somewhat ashamed that I was liking it. She was so hot, beautiful body, perfect breasts, lips, legs...and a cock. I couldn't take my eyes off of the TV! At some point, my friend got up and left the room, so I took the opportunity to rub myself through my pants. I wanted to touch myself so badly. I wanted some relief, I wanted to keep watching this movie!
When he came back into the room, he had changed into a T-shirt and shorts. Since we had come to his place right after work, I was still wearing my black work pants and collared shirt. He had brought me a pair of shorts to put on, but I was afraid he would see my hard-on if I got up to change! He said, "Go ahead and get comfortable ", so I slowly went to get up, and that's when things happened. As I went to get off the couch, he moved down and kissed me and grabbed my cock at the same time. I didn't know what to do. I wasn't gay, but it felt good and wrong at the same time. He started rubbing me through my pants, and asked if I "liked that"? I was a bit scared, and confused, and nervous and ready to cum in my pants!
I told him I didn't know and that I wasn't gay. He said that it was okay, we were just two friends helping each other out. I was rapidly sobering up, and began to panic a bit. I wasn't sure what was supposed to happen, why I was feeling certain things, and how was I supposed to get out of this situation.
I finally got up and said I had to go, and I would see him at work. He tried to apologize, and I said it was okay.
I left his place and went to my apartment. My roommate was at work, since I worked overnights. My mind was racing about what had happened. I had gone to bed, since I went in to work that night, but images of the movie were playing in my mind, and remembering him rubbing on me, I started to get hard. I began stroking myself to get some relief. What was really messing with me, was that while I was thinking about the movie and the hot blonde, I was fantasizing
