Gay Sex Missed Opportunities

Too many to count. I’m just very dumb.

Also, a college roommate, a blond twink type. Very much my type. He would get drunk and come back and get naked and try to get something going, but I was afraid to do anything with him, as I was in the closet. Also, he was dating a scary redneck girl. So I figured if she found out she would kill both of us.

I made out with this musician I had a crush on back in the early 90's. I could have gone further, he was very hard the entire time we were deep kissing (I'd never seen so much pre-cum seeping through someone's jeans) but I stopped us just short of getting naked and going for it. I had a lot of friends dying at the time so I just didn't want to risk it with him. He's still alive. I should have fucked him silly.

It’s difficult because you don’t always know if people are sincere. A lot of people are just dickteases and want to see if you will respond - but then shut you down if you do.

Sometimes it’s just to feed their ego—sometimes it’s just to have a “story” to laugh at you about with friends later. “Guess what? — came on to me! “.

Worst case scenario you get bashed. That’s how Mathew Shepard ended up beaten and tied to a fence—by thieves that led him on.

I was waiting tables in Nantucket before I went back to grad school, and there was a hot as fuck guy who came in for breakfast one day, and started flirting with me. When I told him that I was going to Dartmouth for grad school, he lit up, because he tried to get in but didn't. He was in Nantucket for just a few days, but came in to the restaurant for at least two of his meals a day. It was obvious he wanted sex, but I was seeing someone at the time -- who wasnt on the island -- and I was being faithful. It has been 30 years, and I still think about that guy. He was so much my type. Dammit.

[quote] he definitely tried to get things going a few times

How, OP?

My roommate for a summer. I was too scared. I was 19. He was 29. We shared the master bedroom. I think he was a male escort. I slept on the floor and he had a queen size bed. He offered for me to sleep in his bed with him instead of on the floor. I laughed and acted oblivious to his come on, but I would jerk off in the shower thinking about him. This was right when AIDS exploded. 1989. I was terrified and retreated deep into the closet and only dated girls for like 10 years. I always longed for guys. Then the internet was invented and gay porn was invented and life got good again!!!

JFK, Jr.

I had a college roommate try to get me to jerk off with him. Later his girlfriend asked me In front of him why I tried to get him to jerk off with me. I was so shocked and embarrassed I didn’t know what to say because I was still closeted. I just looked at him and he looked at me sheepishly and looked away because he knew it was BS. She was drunk so it just fell by the wayside, but it it made me realize this guy was shady and a liar. Later he tried to OD on Sominex and left school due to depression so obviously I was the least of his problems.

Both the internet and gay porn were around long before 1989, r7.

Bodybuilder best-friend of mine. Great muscles, bubble butt. Very good looking. He initiated a couple times but didn't want to ruin friendship because he was going through personal issues. Don't regret it.

r10 You're a fucktard. The internet wasn't around until roughly 1995. You're thinking of INTRAnet not INTERnet. And streaming gay porn wasn't functionally useful until the 2000's!!! NoW FUCK OFF!

Prince Rahim Aga Khan

Tony Ward. New Year’s Day, 1996.

I’m a guy.

R7 Is right. I used to rent porn on VHS back in the late 80s but it was hard to find to rent unless you lived in the big city. And good porn was expensive to buy via mail.

Never regret having the intelligence not to fuck around with a roommate. As we all know, things can, and often do, get very weird after the deed is done. No regrets, there's always better sex in the future...

My college required freshmen to take an exercise class,I took weightlifting. We were paired up the first day and I got Tony, a tall good looking guy who wore those spandex shorts. Everyday other day from Noon to 2 I got to see his bulge. We got pretty friendly and he asked me when I was going to come down on a weekend an party with him (I commuted because I worked in my hometown 30 miles away). I came down one weekend and we go out Friday night. We both get pretty drunk and head back to his dorm. He had a single room dorm room so I was planning on sleeping on the floor. We get back and he gets down to his underwear and crawls into his bed. I just grab a blanket and start to lay on the floor an and he say s "don't be stupid there is plenty of room in the bed." So I sheepishly got in. He laughs, still drunk and says "I was hoping to get a blowjob tonight..." and me being young and dumb say "too bad you didn't hook up at the bar.." and that was that we went to sleep. Missed my chance to blow him.

R17 :( this story felt familiar to me.

So many missed opportunities!

The one that comes to the top of my mind is when I stayed at a gay guesthouse in Toronto and one of the owners took a shine to me. I thought he was smoking hot, too, but I went out on the town and missed him coming to my room. He was beautiful, muscular and....as I saw when he grabbed his cock through his shorts - hung.

r18 If your name is Tony and you remember it then yeah it would lol

I had a hot straight housemate I fantasized about when we were living together. Would jack off thinking about servicing him. A year or so later we reconnected and I admitted it to him while chatting. He invited me over and I got to fulfill my fantasy (he had just broken up with his gf). He has a. great cock, two huge loads from him. He even sucked me a bit. Very hot hookup. Haven’t seen him since but he’s married to a woman now. I did add him on Facebook and never got a response so like previous posters have mentioned, it can jeopardize friendships.

R6 standing in the door of my room, fresh out of the shower with his dick very visible under his towel for a long period of time, he would also just whip out that monster to pee outside in front of me, also would get drunk and crawl in bed to “talk”, sent me a picture of something random at the dorm and his dick was visibly hard in his pants in the picture and just generally flirtatious.

Rob Farrell. 6 ft 2, silky dark hair, big green eyes. He was 19 and I was 17. He asked me to come back to his place for sex but I chickened out. He moved away the next month and I never saw him again.

OP, if you still have a chance make your move. Years go by so fast and suddenly you're old and you've lost your looks. Grab your ex-roommate by the balls and suck that cock like it's the last one you'll ever see.

Michael O’Hare.

When I was an undergrad (in LA in the 90s), I saw a dermatologist for a cyst behind my knee. My derm was this extremely hot, young, hairy Middle Eastern dude who lived to the south, in one of the ocean communities. He flirted with me a lot, rubbing my legs, saying I had nice legs, "do you work out?" and that sort of thing. He told me he worked as a stripper when he was younger-- that's how he paid for medical school, he said. Once he invited me to come hang out with him at his place on the ocean but I just was too scared. I thought he probably had a huge cock and would want to fuck me, and I'm not a bottom. I was just kind of unnerved by him. But he was really sexy and now of course I regret it.

My best friend in high school/college. He looked like a thicker, Italian version of Mario Lopez. A true alpha jock. He would parade around in tight briefs, his fat cock and huge balls straining against the fabric. It used to drive me crazy. Some nights after the bar we would drunken wrestle. We grabbed each other’s cocks a couple times but never really went further. We lost touch after college but reconnected on social media a few years ago. He’s married with kids on the other side of the country but he will occasionally send me pictures of his cock or jerkoff videos. I regret never blowing him but I’m amazed and turned on by what’s developed.

Just out of college I worked in a store in Harvard Square, I was 21. there was a guy who worked in the store across the court who was great looking, dark-haired, about 25. He was always looking at me and checking me out, and I was interested but had a girlfriend at the time, I'm bi and hadn't been with guys yet. But still think about him. When I was at college one of my younger frat brothers was really cute. I had an apartment (seniors didn't live in the frat house) but he lived at the house. We hung out sometimes, he gave me a lot of hints, he fell asleep at my place a few times, on my shoulder once, but like a dumbass I did nothing. Still think about him too.

All you whores need some CONFIDENCE!!!

Fortune favors the bold, bitches!

r12 is a piece if shit moron who doesn't understand that VHS gay porn was common and easy to get since the early 80's and the internet was invented in 1969.

When I was 20 and a senior in college (long story), I accompanied a grad student singer in a recital. He invited me to his party after the concert. Although I was not out or sexually active then, it took me all of about 10 seconds to realize that all of his friends were gay....and they were cute. One really chatted me up and it was clear he was interested - we even talking about how fun it was to go out dancing - but I had no idea how to proceed and it was only about 2 weeks before graduation, so I didn't follow through or make any effort to contact him. That would have been a very nice introduction to gay sex. Instead, I waited another year and a half, and got off to a pretty tawdry start. (Let a stranger blow me in the infamous piers of Christopher Street).

There have been hundreds of other missed opportunities in my life. That was only the first. However, I managed to get a lot of fun in anyway.

The song that started playing after each missed gay sex opportunity by DLers

[quote] He’s married with kids on the other side of the country but he will occasionally send me pictures of his cock or jerkoff videos.

R27, it sort of sounds like your buddy's been fucking guys all this time. You don't just start sending wank vids out of the blue to your old buddy. Still, hope you get him one day although I'm not saying he should cheat on his wife. Then again, like said, he's probably been doing that with guys from the start.

[quote] When I was 20 and a senior in college

[quote] I was not out or sexually active then

WOW.

Not a bitchy or mean wow, just that I am surprised you got to age 20-21 and hadn't had sex yet!

R27 Please share said "wank" videos.

R33 I was the one who asked for the cock pics after he sent a few texts about not getting laid by his then girlfriend. But, you may be right that he has been fucking guys. He didn’t need much persuasion to send them. And in later videos he plays with his ass. I still wouldn’t want to mess around with a married man but I feel less guilty about jerking off to the stuff he sends.

R35 I would love to share the videos but I can’t in good conscience.

R37, of course you shouldn't. Ignore people asking it. The guy's your friend and doing this would totally alter your relationship, if only in your head since you'd know you leaked it.

R38 Thank you!

Loves it.

MG: Totally hot guy who would deal drugs in a low-key way. Seriously hot, nice dick (men's room peeping) and one time he asked me if I were bi. I said, No, gay. Two nights later he comes up behind me in a bar and whispers in my ear that he's having a small party at his place. Who's gonna be there, I ask. Just you and me, he says. He gave me the address and I mixed up the numbers. He never asked again, though was always pleasant. (I didn't buy drugs from him.)

HE: So achingly cute with a perpetual confused look on his face. Ran into him now and then. At a party, I was on the way downstairs to get a taxi and he stopped me and kissed me. Beautiful lips, soulful kiss. Thing was, I was terrified of his girlfriend. She was a total Italian princess who loved talking about how she'd fuck up any chick who messed with HE. You bet I was cautious.

[quote]he comes up behind me in a bar and whispers in my ear that he's having a small party at his place. Who's gonna be there, I ask. Just you and me, he says.

Smooth, heh heh.

I was sick of hookups and was trying to make friends instead.

I met a gorgeous, muscular guy who turned out to be Sam Champions ex. I sat in his apartment as he showered, came out in a towel, and dressed in front of me. We then went out and had lunch. I know he wanted to have sex, but I didn't take the bait.

Anyway, he did talk about Sam would beat him alot and the meth they both did.

We never turned down the opportunity for actia!

R43 this is now a Sam Champion gossip thread

Years ago, I was working in an office while some construction work and electrical work was being done in another part of the building. One afternoon, I had to go to the men's room, which was in the construction area. As I headed toward the men's room door, this amazing, scorching hot, young bodybuilder in a tank top came out of the men's room. Turns out he was an electrician, and he had one of the most beautiful bodies -- and one of the most gorgeous faces -- I've ever seen, a young Italian-American muscle guy, probably about 25. When I first laid eyes on him as he walked out of the men's room, my eyes got really wide and my jaw dropped, and he registered all of that and knew immediately that I was a gay guy stunned by his awesome body. I didn't know what else to do or say, so I just continued into the men's room, but when I came out, he was sitting alone with none of the other construction guys in the immediate area. So I spoke with him briefly and told him how amazing he body was, and he thanked me. Then I said it AGAIN, because I was just so overwhelmed, and he thanked me again. I'm pretty sure he would have been very willing to make a date for me to worship him, but I was too nervous to be forward enough to suggest that, so I went back to my office and never saw him again. I can't tell you how often I've wished I had been a little bolder, so that it might have played out very differently.

My college roommate was so annoying and had even more annoying friends that he'd bring into our tiny room while I was trying to sleep. They'd laugh like hyenas. He was gay, too, but I was still a virgin in the closet. I keep thinking maybe we could have smoothed over things a bit if we'd just fucked. He wasn't really my type, but he seemed like he'd have a big cock.

My other main missed opportunity was this really sweet guy who I used to see on Grindr a lot when I was single. He ended up working with my husband for a while and I got to actually know him and he was the sweetest guy in the world. Very tall and handsome and kind of reminded me of Armie Hammer. Once I got to know him, all I could think was that I wanted to climb him like a tree and should have done it back when I was single.

Story 1: I was just coming back home from a trip to Australia. It was early December. I couldn't sleep, so when the Uber brought me back to my apartment, I went to my car and drove around, stopping at a 24/7 dinner, before calling it quits around 4 am. My jetlag and exhaustion caught up with me as I woke up with a cold boarding on a fever. Since I was home, bored, and alone I thought I'd check out Grindr. I happen to catch the attention of a hot 22-year-old swimmer in town for his last day of winter break. He was was hot and very into kinky stuff. I had to laugh at a swimmer into light water sports (I've never done it). We were just being flirty and making jokes, typical Grindr. Anyway, he was about to head over when I finally had to tell him that I was actually too sick to hookup after he told me that he had a meet the next day. He thanked me for the honesty and agreed that he couldn't risk it. We have mutual online connections so I know he wasn't going to flake as he was about to head to my place. Unfortunately, we were never been able to meet before I moved.

Do I regret it? Somewhat, he was a hot 6'2 swimmer, looking to be dominated. But, respect and honesty are important and as a former athlete, I would never want to get someone else sick before a meet. I'm proud of myself, even if my dick was angry.

Story 2: Not really an option for full-on sex, sorry OP, but still somewhat relevant.

My mom befriended this single mother with 3 kids, 2 boys one girl. We spent some time together as my mom could bond with her over being a single parent, blah, blah, blah. Anyway, the middle child, Brian, was around my age so we would hang out. I was a sheltered suburban kid and he grew up in the rougher side of town. Always an adventure whenever we would hang out in each other's neighborhoods. He was a hot laddies man, that already slept with 2-3 girls by 7th grade. I was in the closeted but had never really held down a girlfriend. He joined my mother and me on a road trip out west. While in our hotel room, we ended up jerking off together. I'd never done that with anyone. I thought my dick was a nice size until he whipped out his beautiful uncut monster, he was very happy to show it off. He also bested me in the cum category, shootings so much that a bit got on my arm. I pretended to be disgusted, but when he walked away to get a towel, I tasted it. We were completely normal about the entire thing but I never pushed to do it again.

Fast forward a year and my mom was away on a week-long business trip. I stayed with Brian's family in his bunk bed, his older brother had the top bunk. Every night it took me a while to get to sleep because I was used to jerking off before bed, and now I was sharing a bed with a hot guy. My mother wouldn't allow me to do sleepovers growing up so this was a sadly a thrill. I'd sit in bed and listen to his breathing and could tell when he was asleep, at which point I would "accidentally" roll near him. On the last night, I was dozing off when I noticed his arm around me. I froze and listened to his breathing, despite his beth efforts I could tell he wasn't in some deep sleep. I then turned to put my hand down to my side near his crotch and boxers. I was wasn't sure of myself, but I remember he rolled over again giving me better access. I put my hands into the slit of the boxers to feel his dick. He was getting hard, but I was too scared to really give him a handjob. I think this slow dance went on for 20 min, as I slowly played with him, trying not to shake the squeezy bed with his brother dozing above. Our fun was interrupted when I heard our mothers coming down the hall. My mom stopped by to pick me up. I had never been more unhappy to see her.

In short, my mom's a cock block and I never got to stay other there again.

Jean-Marc Barr

R42 It may not sound like much now, but his intensity and breathtaking sexiness was in every word. I can still hear it some 30 years later.

R50, oh yes, I can totally imagine it.

BTW, thanks for the stories, everybody. They are fun to read.

R49 He was handsome in Hope and Glory. Details would be helpful. I mean, I sat next to Liam Neeson at a bar once but that doesn't mean it was a missed opportunity.

All of the above, and more.

Who r53

Just a DL fave. .

What r55, what's the point of mentioning him if you aren't;t going to name names. If he is a DL fave, then it won't shock the twinks lurking on this board.

He has children. He british, not unknown to the academy, and something of a sex symbol.

Jude Law

Mr. Bean

I met Don my freshman year in college, in the dorm. He lived on a different floor but had been high school buds with some guys across the hall from me. He'd sit with us at meals or swing by our hallway to chat and cut up, and we hit it off.

He wasn't beautiful, but he was very, very cute, with a big warm smile. Sort of preppy, fraternity-boy cute.

He took to casually massaging my shoulders when we'd all be hanging out, watching TV or whatever, while he talked, like it was no big deal. And I happen to love that, so I reacted positively and encouraged him a bit. Then, he'd do it when just he and I were hanging out. Once, he sat on my bed behind me and kinda spread his legs so I could sit down and let him rub my shoulders, and his leg touched mine. At that point I knew he was interested in more.

I thought about asking him to come hang with me in my room to watch a movie or something like that, on a night when my roommate would be out at a party or something, but I never quite found the right time to do it and it never happened.

Too bad. He was really cute and his body language let me know he was into me.

The interior of my office was being repainted and the work was spread out over a many-day period to inconvenience as few of us as possible. One day, one of the painters was assigned to do the inside of the men's room. Accordingly, he'd put "closed/keep out" signs in front of the door. I'd chatted with this particular painter several times during the project and got a hard-on every time. Besides being very attractive, he also gave off a vibe that triggered my gaydar.

On the day in question, I really had to pee and didn't feel like walking all the way to the second restroom, so I figuratively threw caution tape to the winds and went into the off-limits restroom. As I walked in, I immediately saw my Favorite Painter sitting on the toilet, pants down to his ankles, furiously jacking off. His dick was enormous. "Get the fuck out of here," he yelled. I mumbled a quick "sorry, man," and made a quick exit.

I've been replaying that scene in my mind ever since it happened, each time with the same outcome: I'd refuse to leave, confront him with the fact he wasn't getting paid to masturbate, and if he knew what was good for him he'd let me help him.

I can't believe some of these missed opportunities here, guys falling asleep in your apartment or on your shoulder??? Gurl I would have been got the dick!

All my "missed opportunities" are with coworkers, I don't fuck with coworkers ever because they can be vicious.

Your loss r62. I had that same rule till I moved to the “big city” and found that a lot of my coworkers fuck each other then go about their lives. Something about mutual distraction keeps things in check. Also they only fuck while single. Never someone above or below you on the work hierarchy. Always keep it discrete, except for their nosey gay coworker that knows how to keep an office secrete or two.

Got my straight coworker drunk during an impromptu afterhour trip to the bar. After a year of wondering he the size and shape of his cock. If these horny waitress would have left us behind I could have probably gotten him to show me. It’s not the same as a hookup but after 5 min of flirtatious coaxing it was nice to know what 3 of my female colleagues got to ride or suck.

There is an art to fucking coworkers that millennials a seem to have mastered at my job. Or they just don’t care about those rules anymore. If only the hot gay guys would stick around. Long enough for me to get my rocks off. Social media sos also he’ll. You will match with a coworker at some point or see their profile. Give them a positive swipe and they will remember that the next time everyone is out for drinks. Don’t be surprised if your two head home together, in separate Ubers.

Mutual destruction.

Darn, r60. You guys had such a sweet bond :(

Wtf r63? Is English your second language?

Doesn't matter if one is Gen Z or The Greatest Generation, it's unwise to fuck colleagues. Sheesh

[quote] Doesn't matter if one is Gen Z or The Greatest Generation, it's unwise to fuck colleagues. Sheesh

Never have understood the big deal. I mean I know people whose parents met when they worked in the same office. I've gone out with people I worked with. A friend and his girlfriend met when they worked at a bookstore. Ever see the movie Shop Around The Corner? After school or college, one of the main places people meet other people is in their workplaces. If you meet someone special, I don't care where, go for it. Life's too short.

R68, it's obviously all fine and dandy when things go right and you meet your soulmate, or when both parties can take a fling as nothing to get worked up about but when things end badly the whole workplace can suffer.

I had it happen in college when things ended badly with a schoolmate and I became a persona non grata in anything they did, which involved classes I was taking. Not fun, I can tell you. People can be cunts, especially when romantic feelings are involved, and it doesn't necessarily matter how old you are. Crimes of passion can happen in any age, which tells how people can react emotionally.

R69 more details, please. Did you guys just have secret gay sex or was it a breakup?

R70, he was bicurious and experimented with me. I wanted more but he pretty much pretended to his schoolmates that I was a crazy gay man hitting on an innocent straight guy. BTW, it was partly true since I really did fall for him and he most definitely was only experimenting and we certainly didn't have a a romance going on so I take much of the blame. But, it was a good example how a fling can raise strong emotions not just in the parties involved but in people around them as well, and a workplace is a perfect example of a place where things can go wrong especially since people's livelihoods are at stake and not just their dignity.

R71 you are right. Plus “straight” guys who play gay for a day often regret it afterwards and then resent you for having “made” them do it. They react to you like a sexual predator that took advantage instead of someone who willing participated. This can result in being ignored, hostile behavior, or physical violence. Be careful.

B. D Wong, among many, many inconnus.

He was my senior in college, he only dated girls his whole life, and I was (and still am) very closeted. We were doing a project in a small village where we had to share a bed for two weeks. There was a moment when he said that he would've a crush on me if he was a girl. The biggest missed opportunity was at our last night there, he asked me whether I mind or not if he's about to sleep naked (he usually sleeps with clothes on), he decided to sleep with his underwear on and then told me that he don't mind some cuddles. I was so tired that night and there's no cuddle.

Though a little off topic, I'm thinking there are so many self-imposed or societal taboos these days they may just be replacing former taboos, and that's not good either. For ex, gay relationships were once socially unacceptable, and work relationships were considered acceptable. Now it's the opposite. When I was in middle school I asked one of my teachers how she met her husband. She said he had been her professor (asst professor) in college, and asked her out. She said he was in his 30s and she was 20 or so. This kind of relationship is considered taboo today but wasn't when they met. But they were happily married so - maybe they would have had worse luck if they hadn't gone out. I know this is a radical thought but maybe today's taboos are just tomorrow's stupid prejudices.

Great thread.

Agree about straight curious guys blaming you for seducing them after the fact--had that happen twice in high school/college and it took years for me to realize that I had not in fact seduced them, that it was mutual or, if anything, the other way around.

But with that as background... I was working for a tech startup right after college. There was a guy who was around my age, he was one of the engineers (code monkeys) and it wasn't that big a place so we knew each other. One day I saw him changing his shirt--he was going to head to play softball and he had a great body, I am sure I was staring while we talked. Cute buy, blonde, blue eyes, sort of Slavic looks and from a more blue collar background than most of the people who worked there.

After that I always got a flirtatious vibe from him, like he'd touch or pat my shoulder or grab my arm when he passed me in the hall--it was bro-ey enough but I still got a vibe.

Cut to company holiday party and he is very drunk, I am slightly drunk.

He comes up to me and immediately starts rubbing my pecs, thumbs my nipples. I get hard right away but we're at a party and then his code monkey friends come up to us and I start squeezing his pecs back, like we're bro-ing it up and comparing pec sizes or something and they seem to think this is normal and funny.

They walk away and it's just me and him. Part of me is thinking I should bring him outside to smoke the joint I had with me and try and get something going, but another part is thinking that it's a small office, he's pretty deep in the closet if he's even aware of his feelings and is likely to react negatively the next day, he's seriously wasted and I would be taking advantage and so I steer him back to the main party and go hang out with the other product managers.

The next day one of his buddies asks me "why were you and Steve feeling up each other's pecs?" and I was like "cause I told him mine were bigger and he was jealous" which he laughed at and seemed to accept. (I was tempted to say "because he was drunk and coming on to me" but didn't.)

Steve was, of course, awkward around me after that, no more shoulder squeezes and no more stopping by to talk about the Dodgers or plans for the weekend.

I FB stalked him just now, he's still in great shape and appears to have a fairly serious girlfriend.

These "missed opportunities" so often have a Lady Chatterley and the gamekeeper vibe. What was that recent article about gay men wanting to claim a high social status? "I dreamt I lived in marble halls....."

Which ones R77?

Most seem to be about someone not coming on to their college roommate

The problem is when you have sex with a closeted or secretly bi man, you become the personification of their shame. If hetero co-workers have sex they might feel embarrassed or uncomfortable around each other, but eventually they move on. In this situation, you become a constant reminder of what he did—and something he more than likely doesn’t want to be. How that man deals with that reality can result in really ugly consequences for you.

R79 that’s actually a great point about fucking around with straights.

Lots-couldn't possibly catalogue all of them.

One day I was sitting at work and the phone rang and he said, "Hi. It's Mike." I didn't really recognize his voice and I know several Mikes but I didn't really think anything about it as I figured I would figure out who it was by the process of the conversation. After just a little chit chat, he proceeded to tell me that he was really wanting to get in my pants and slide his tongue up and down my thick cock shaft, etc. I had never actually taken the plunge but the conversation made me super hard. I was non-committal but kept chatting and kept trying to figure out who "Mike" was. I was really, really, hoping it was a particular guy but I always called him "Michael" and not "Mike." I couldn't figure it out and was just too stupid/polite to say, "Wait...WHO is this again?" because I didn't want to offend him. I ended up saying no.

I saw the guy who I hoped it was only a couple of more times before he moved away. If it was him, he never let on. I've always regretted how I handled all of that and wondered how things would have turned out differently if I had.

R82 — I had something similar happen. I got a call at home at about 10 pm from a guy with a nice voice who greeted me by name and said he'd been thinking about my cock since the weekend. I had no idea who he was, but I didn't want to say too much in case it was a prank setup by some friend. I coolly played along for a few minutes until I determined that the dude was serious. We realized at about the same time that it was a wrong number—he'd misdialed his weekend one-time hookup, who had the same first name as me, by one digit.

We then proceeded to have the most amazing phone sex for about 45 minutes, until we both came. I wanted to meet my sexy caller the next day, but he couldn't. He had only been in town for a week on business and was flying home the next day. He had originally called to chat with his weekend conquest and thank him for a nice time. I told him that he now had my number and to call me if he was ever back in town. That was 3 or 4 years ago. I don't think it's going to happen.

[quote]you become the personification of their shame

Mary!

[quote] Most seem to be about someone not coming on to their college roommate

Ha, had to laugh. It's probably not terribly uncommon for some interest to happen there.

I had two separate roommates in college - one my freshman year and one the fall semester of my sophomore year - who were hot dudes and, to my knowledge, 100 percent straight. Freshman roommate was a wrestler (I used to sniff his jock, etc. all the time) and the sophomore roommate was a wiry, lanky nerd. Hot, but nerdy.

In both cases, we ended up fooling around the very last week/10 days of living together.

So not quite a missed opportunity, but I took my own sweet time! And especially with the wrestler, I regret waiting so long. He had the perfect body and dick, with just a light dusting of blond peach fuzz in all the right places, and he had huge loads every time we played around. I could have gotten addicted to that very, very quickly!

And if you think you read about my freshman roommate before, you did - see R1 of this thread

bump

hump

pump

a few, so clearly I didn't learn my lesson the first, second or fifth time!

Two I want to travel back in time for and have had frequent faps over:

- I was in a frat in college and over a holiday break one of the brothers told me I could stay at his place because I had tickets to see a concert in the city. He was hot, tall, dark Armenian American guy. six two, stacked with muscles, thick black hair and eyes and a chiseled nose (i like a strong nose). He was also a campus cop (is now a sheriff). I had heard he was bi. So I go to my show, come home, take a hot shower and climb into his bed. It smells of him. Nice. In the middle of the night he slipped into the bed. He had "decided to come back early.' I move in my sleep a lot. I rolled over and my hand smacked him in the face and gave him a bloody nose. Totally ruined it :( I was too chicken. It was the mid 90s and i hadn't even really kissed a guy.

The other time i was living in a corporate housing situation for a college internship on the west coast. There was an issue with the bathroom and this SMOKING HOT plumber came by. It was about 5'11, very Italian looking, pale skin, black hair, scruff, dark brown eyes, great arms. I was a twink. I felt confident if i offered to blow him or more he would have done it but i chickened out. he even came back a few mins after he left 'just to make sure everything was still ok.' i was so nervous i was shaking. what a dummy I was!!!

Most of y'all really don't know how to work it!

I tend to do my workouts late, when the gym is fairly empty. One night, just a handful of people were still around. One guy, dark-haired and olive-skinned with an ASU baseball cap, somehow managed to always be on the machine I needed—or vice versa.

We were locked into that mutual orbit for nearly an hour, but never spoke. Ultimately, I lost sight of him but spied his ASU cap left behind on a weight bench. I glanced around but he was gone.

I headed to the locker room 20 minutes later, intending to change and head home, but since it was blissfully empty, decided to try out the sauna for a minute. Surprise- there’s ASU guy, sitting against the far wall, eyes closed and apparently half asleep.

I was too nervous to speak, but managed to croak out something dumb about “Did you have a cap on before?” A conversation slowly began- found out we have the same first name, that he’d just moved in with his fiancée, and that he was at the gym because she was at her bachelorette party.

Our towels gradually fell away, shy mutual compliments were murmured, and he pretended to doze off, yet managed to relocate his hand to my thigh and let it maddeningly rest there. His body was perfection, and within minutes, he had a semi. The spell was broken when an obliviously chatty older guy entered the sauna, and ASU guy retreated.

We got dressed, walked out to the dark parking lot, and he followed me to my car. He asked, “How late do bachelorettes go?” and then, “If I kiss you right now, I am asshole?” He put my hand on his bicep and then up the front of his t-shirt, but then got guilt-stricken and pulled away. He had me put my number in his phone, but never called me.

Still think about that night. A lot.

R92, correcting a typo: he’d actually said, “If I kiss you right now, am I an asshole?” Sorry for the long pot!

Fuck— I mean “post.”

you complimented each other's junk?

R92, aww, that was sweet and hot. Not for the bride, though, since I doubt the guy can keep it in his pants ;)

A “straight” married colleague stroked my thigh under the table at a work night out. He was handsome, an ex-policeman, very sexy. I was young and inexperienced, a raging mass of hormones, but despite being very attracted to him I played dumb and moved away from him. I have never fooled around with anyone at work. I’ve seen it go horribly wrong.

bump...no more stories??

hot hot hot stories

More importantly re: R12, AIDS “exploded” much earlier than 1989. Try about 1981 - 1983. Rock Hudson’s death was in 1985.

R12 I got my first computer in 1992, an IBM with Windows 3.1. The Internet existed at that time, definitely.

Years ago, when i was in training for a new job, we were sent to another city for a couple of weeks. We were staying in a hotel, and were forced to have roommates. I was stuck with this attractive straight guy, who was a little off. He thought there were cameras watching us in our workplace, and other mildly paranoid things. Despite that we had a decent time, we had dinner together each night, making sure to max out our per diems.

One night we went down to the hotel pool, and hot tub, neither of us had bathing suits, so we were just in boxers. I remember coming back up in the elevator he pointed out that you could see his whole dick through his wet boxers, I had definitely noticed as he had a huge dick.

Nothing happened on the trip, but when we got back to town, we ended up getting a drink together, and a friend of mine joined us. That night I had some other plans, so I left this guy at a bar with my friend, who was certainly no looker. The next day I found out my friend had slept with my workmate, the work guy had wanted my friend to cum on his face, and fuck him, he didn’t. I didn’t see much of him at work after that, and he ended up leaving the company. I still kick myself that I could have been fucking him all that week we were away, if I’d only been swifter in picking up his signals.

We actually had sex, but I wish I'd gone back for seconds. He awakened some sort of animal desire in me that I'd never felt before. You wouldn't think he'd be the type either. He was clean cut and preppy, but the first thing he did after we made out was stick a butt plug in my ass that had a tail attached. He told me I was his puppy and I'd have to do as he said. He pulled it out and started fucking me. He sat on my face and I got to suck on his perfect hole and squeeze his supple cheeks. I'd have never come up for air.

He took me to the bathroom and told me to lie down in the bathtub. He pulled out the biggest dildo I'd ever seen and tried to squeeze it into my asshole. I couldn't take it as first, so he gave me a bottle with poppers inside. I'd never had them, but I gave them a hit or two and it was the most amazing sensation I'd ever felt in my life. My asshole basically shot open and he was able to put the dildo inside me. He took it out and began fingering me, working one finger in, then two, then three, until his whole hand was almost inside. He got so close, but as much as I wanted it, it wouldn't allow him inside.

We finally finished each other off and went our separate ways. We tried to plan another session, but our schedules kept getting in the way. I never knew I could be into all of that stuff, but it turns out, I was. He made me embrace my inner whore and he'll always have a special place in my heart for that.

Beautiful story, R103.

Very touching, very Academy Of Dramatic Arts.

[quote] He made me embrace my inner whore and he'll always have a special place in my heart for that.

MARY!

Damn. I need to go pull my pud now. This thread is great.

send us photos R107

[quote] He took me to the bathroom and told me to lie down in the bathtub.

I had a furry, muscled father of five with a long, fat, veiny cock tell me to do exactly the same thing....but it wasn't so he could shove a dildo in my ass.

He turned on the water, huh, r109?

R110 Well...you could say that

[quote]He took me to the bathroom and told me to lie down in the bathtub.

r103 must be a dwarf. Who can lie down in a bath tub?

bump

A real beauty frat brother, still is per his Facebook page -- but he was very religious and I knew I would be a pariah afterwards, even if he was the one initiating the sex. So I passed and it was tense ever after for us. Even then, I knew that shit was too phony, sex one night, an open Bible left on my pillow the next (another frat guy, no lie, but I was in love with this one for years).

I wasn't so much closeted as not anxious to lock up a lot of numbers on my bedpost; as long as I was in love, it wasn't "bad". In that respect, I am glad I passed. Made up for it when I moved to LA and got a little older but, at the time, I would not have done well with shaming or any of that rubbish.

During the late 70's, I met a guy from a frat house across the street. Our frat had a couple of parties with them with a couple of Sororities. After talking to him at these parties, I came back to my room, with him sitting on the small couch in my room, talking to my room mate. My room mate left and him and I started talking. He slid over closer and put his arm on the couch behind me, not really odd, but I was getting nervous. He asked me to come over to his house and I did.

We went up to his room, and he had a single. When we got in the room, he stood there and took his shirt off, then asked if I would like to get comfortable with him. I said I had to go, and left. I was terrified.

I wish I acted on that one moment. It could of changed everything for me. He was a stunner. 6'6" and the body of a god with long brown hair. We would just waive at each other on campus after that.

R115!!! Oh man, you blew it!

R115 here...And HOW R116!

Always good to avoid the pious when it comes to sex. Later they blame you for their sexual downfall or pretend it was all about you, not them.

I had a religious friend lwho was clearly in denial about his sexuality (bi or gay) and would talk about being chaste—but would try to engage me in sex talk or quasi-sexting/phone sex when he drank or got really horny.

At first it was fun, but I got annoyed because when I was honest about sex—or talk about something relevant to discussions we’d had during “his moments of weakness”, he’d act like he wasn’t interested at all and would treat me like I was some pervert for even bringing it up.

So after that, when he’d start talking about sex, even if I was down for it, I’d flip the script and start talking about how I wasn’t interested, that a chaste life was best, etc After a while he got the message and stopped. He was hot and I was down, but his duplicitous, hypocritical bullshit was just insulting.

See R118 I think I wouldn't have minded whatever label he needed to put on me so long as he was down.

Yeah I’ve had hot sex with repentant hetero buds but it’s the risk if ruining the friendship. Is it worth it? But with that dude it was like I was his hidden sexual outlet. I would have been cool if he hadn’t been so dishonest and self-righteous about it and treat me like it was only me.

[quote]During the late 70's, I met a guy from a frat house across the street... he stood there and took his shirt off, then asked if I would like to get comfortable with him. I said I had to go, and left... I wish I acted on that one moment. It could of changed everything for me.

It certainly could have, R115. Too bad we couldn't have hooked up that night.

My stepfather. We kissed but I freaked out and stopped it. I regretted it all my life. We talked about it many years later and he was willing to give it another shot but by then he was fatter, older and unattractive so I said no again... and regretted that one too to this day.

These were initially missed opportunities with someone that wound up panning out over time.

Back around 1994, I had a friend in my university wind band who played tuba and was steaming hot. His name was Heath, and he had a beautiful body and hairy chest. He played basketball all the time, so he frequently wore loose shorts and tank tops. He was flirty and totally comfortable around me though he was a total pussy hound and knew I was gay. He always laughed at my jokes, even the dumb ones. A few times, he said if he were gay, he'd get with me so fast because I always made him laugh.

One night, I stopped in to see him at his job to show him the new car I'd just bought. We went for a short ride, and I drove toward my new apartment. I told him if he wanted a soda or a sandwich, I could stop in. When I turned off the car, he suddenly turned to me and said, "You know, even though I'm not into guys, I think I'd probably enjoy being on... the receiving end of... you know... if it were with you." Though I was so turned on from this that I felt the pre-cum on my thigh, I said, "Forget it. I'm not blowing anyone who won't blow me back!" and we had a laugh and I dropped him back off at his workplace.

A short time later, we were on tour with our university wind band and orchestra and were sharing a hotel room. After we got into the room, I stretched out on one of the two beds to take a nap, and then he started jumping around the room, shucking off his clothes. He said he was going to take a shower. Then, he just walked up to the side of my bed and started swinging his enormous cock back and forth in my face, laughing like a maniac. Jesus, it was a giant. Mouth-watering. Spectacular, and his balls were, too.

I was so conflicted. On one hand, I knew he was baiting me and would have been down for some action (although one-sided); I imagined him holding my head in his big hands while bucking his thick manhood mercilessly into my throat, not letting up until I'd swallowed his hot wad. However, on the other hand, I remembered all the skanky women I knew he was hooking up with and wondered if he might have an STD. Plus, his weird, random behavior reminded me of Kramer from Seinfeld, so it wasn't exactly erotic but mostly bizarre. I told him again that I'm not blowing anyone who won't blow me back, and he turkey-slapped me with his cock and went into the bathroom to take his shower.

I immediately jerked off there on the bed and was finishing up just as he was emerging from the shower. He knew I'd done it, and I guess wanted him to know. I still had some cum on my hand, and with one eyebrow raised, I showed the cum to him before I licked it off and grinned. He said he was going out to try to hook up with the harpist from the orchestra and would be back later if he didn't get lucky.

I was asleep when he got back. The room was pitch-dark as I'd closed the blackout curtain. When I awoke to pee, he was in my bed and was spooning me. I could smell that he'd been drinking. His cock was hard, and the heat that it emanated against my ass was too much. He started gently pushing it against me. I finally decided what the hell, turned over, and went down on him. I sucked and licked him as if his meat were my last meal. t was the first and last time I'd ever had one that huge in my mouth, and when he finally blasted, his semen was so copious that I couldn't take it all. He didn't reciprocate, but he didn't mind when I used some lotion and thrust against his ass crack until I too came really hard. When we fell asleep, I was spooning him nude with my cock still softening between his ass cheeks.

It was only that one time, and we never spoke about it afterward. He soon got a Mormon girl pregnant and was coerced into marrying her by one of our professors. He's now mostly unrecognizable to me... fat and ugly, bald, and has six kids. Mormon, Republican, yuck.

The guys in my fraternity knew I am gay. Several would try to “hang out” in my room after parties. I politely excused myself from some. The five guys in the house I really wanted to blow were rewarded when they hung around. Two got naked before we even started to play. Two of the five blew me in return. I believe this is common among fraternities.

So hot R123! Thanks!

R124 I bet they talked about you behind your back calling you a whore.

I noticed that one of the actors from KING KONG is now in THE PERPLEXED, and another actor from KING KONG is now in the DIANA musical. Sad.

Can't remember any missed opportunities.

I came out to a handful of close male friends during my 20s and 30s. A few of those friends eventually hinted about fooling around. I have fond memories of those opportunities.

bump

When I was in my late 20s, I managed a team of people, most of them kids still in college or just graduating. One of them was a big, blonde, beefy 20-year old kid who was a little dim, but who had a heart of gold. For some reason, I think he looked up to me as some kind of a mentor.

Occasionally, he would come over to my apartment after work and hang out. I was extremely attracted to him, but never let him know it. One night he came over and was wearing a pair of workout shorts. He was sitting on the couch across from me, his legs spread wide apart. He wasn't wearing any underwear, and his blonde, furry ball sack was peeking out the right side of his shorts.

I was going crazy and wanted to pounce on him right at that very moment. I kept trying to not to stare, and he seemed oblivious to the fact that he was hanging out. Finally I said, "Dude, your balls are hanging out." He just looked down and them and said, "Oh, yeah.." Then he smiled and looked at me and said, "You like what you see?" It was a clear invitation, and I was so tempted, but I just kept reminding myself that I was his boss, he was my employee, and how all of it could go terribly wrong and I could end up losing my job and worse.

So I pretended he was joking and just said, "Put 'em away, dude," then changed the subject. Although I really, REALLY wanted this guy, I'm glad I didn't act on it. The potential repercussions wouldn't have been worth it. But to this day, I sometimes play out the fantasy in my head of me accepting his invitation.

Today, he's married to a frauish woman and has 3 little rugrats. I sometimes wonder if HE ever plays out that fantasy in HIS head.

R12

Possibly the most most ignorant post I’ve read on here in a while. An intranet is just a non public IP network, you dolt.

The World Wide Web might not have been around, but finger, FTP and email were definitely around.

I hate people who act like they know what they talking about based on some 101 class.

You have discipline, r130!

R123 R130 Is it hot in here, or just me?

R130 It was NOT easy, that's for sure.

^ I meant R132

This one is embarrassing a bit. A guy I worked with (Italian with a good body and a handsome face) and I became friends over a period of time. I’m about 7 years younger than he, and at the time was deeply in the closet ( as I was hit on constantly,, and very wary). .When we first met, he had just broken up with a long time girlfriend and I was new in town and didn’t really know anyone.. He began to upon occasion make suggestive comments to me that led me to think he was thinking about me sexually. One Friday night(around 11:00), there was a knock at my apartment door, and it was him. I let him in, and the first thing he said to me was “I’m not wearing any underwear ”. I let that go without a response, and asked him if he wanted a beer. He drank it and left. I regret not saying “prove it”.... I never slept with him...pitty....

R136 How's that embarrassing? We've all been there when we've had opportunities right in front of our faces, and for various reasons, chose not to act on them.

I feel ya, buddy.

[quote] as I was hit on constantly

Define constantly

Every third blue moon r138

Every third blue moon r138

r138, R136 here. Like about every time I went out. And at work too (male and female).

I’m always wary of guys who do this because I don’t like being toyed with. Also there are guys think it’s funny to lead gay guys on then laugh about it behind their backs.

A few years ago I hooked up with an ex housemate and it was one of the hottest sexual experiences in my life. He identifies as straight and is married with a kid now so I think it cost me his friendship so think before you act.