Friend “almost” Encounters

Outlawok

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Anyone have a story about their “almost” encounter with a friend that they can’t stop thinking about?

here’s mine: I’m in college my best buddy is married with a kid, working. He has no idea of my bi experiences in the past. I come back in town to party with him and some folks. After things wind down his wife and kid are asleep and we are pretty tipsy and still drinking. I’ve seen his cock in the past and it’s very nice about 8-9 in cut and very girthy,
He ends ups getting naked, I really don’t remember why, but I’m sitting on a chair and he stands at about arms length in front of me, he’s completely shaved, he’s flaccid not hard. He says you should shave your junk and balls it feels amazing. Well my mind is racing and I said let me feel yours to see what’s it’s like, hoping to get my hands in there. He then backs up and said we’re not playing that shit, I gave it one more shot with the c’mon just let me check it out. He like no way man. I’m like a”Fuck” in my mind for multiple reasons, desperately wanting to suck his dick and I’m worried I fucked up our friendship, conflict of interest here obviously,

Anyway, we crashed that night and got up and have never spoken about it. We are still great friends.

I still fantasize about sucking his cock to this day. He’s now divorced and I’ve thought about giving it another shot, but I think it’s just wishful thinking though.

Would like to hear similar stories!
 

Cecil56

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My biggest regret was a "missed opportunity" at work, when I was probably 20 years old. My coworker was 1 year younger. We were the only ones working in a mechanic shop at a small farm equipment dealership.

One day, he just walked up to me and whipped out his dick. I was shell shocked and didn't know how to react, so I did nothing. (in retrospect I would give it a squeeze and go from there) After thinking he might want to play around, and I was game, I did the same thing to him. Again, he did not grab my dick either. I think we were just both too shy on making the first move. I have regretted not grabbing his dick for many years now. I would handle it totally different, give the opportunity today.

He got married probably a year later. I was married, he and his wife, me and mine were friends. One night after the wives had been together, mine told me his wife Amy spilled the beans. Said my friend, in his teen years, messed around with another teen and they fucked each other. I never mentioned it to him what his wife shared, but maybe I should have!

Anyway, we got sent to another state together for 5 days each winter on mechanic training. On the second trip, we checked into the motel with prior reservations. Got to the room and there was only one bed. Went down to the desk and said we needed two. None available.
I said fuck it, guess we share the bed. He strongly resisted that, said we are not sleeping together. Ended up getting
a cot, flipped a coin and I lost. Did not sleep worth a shit on that thing.

I think he was scared that his hands might roam. I would have been totally OK with that.
I would not have been down for a fuck, but mutual handjobs would have been fine.
I regret what fun could have happened!
 

Outlawok

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My biggest regret was a "missed opportunity" at work, when I was probably 20 years old. My coworker was 1 year younger. We were the only ones working in a mechanic shop at a small farm equipment dealership.

One day, he just walked up to me and whipped out his dick. I was shell shocked and didn't know how to react, so I did nothing. (in retrospect I would give it a squeeze and go from there) After thinking he might want to play around, and I was game, I did the same thing to him. Again, he did not grab my dick either. I think we were just both too shy on making the first move. I have regretted not grabbing his dick for many years now. I would handle it totally different, give the opportunity today.

He got married probably a year later. I was married, he and his wife, me and mine were friends. One night after the wives had been together, mine told me his wife Amy spilled the beans. Said my friend, in his teen years, messed around with another teen and they fucked each other. I never mentioned it to him what his wife shared, but maybe I should have!

Anyway, we got sent to another state together for 5 days each winter on mechanic training. On the second trip, we checked into the motel with prior reservations. Got to the room and there was only one bed. Went down to the desk and said we needed two. None available.
I said fuck it, guess we share the bed. He strongly resisted that, said we are not sleeping together. Ended up getting
a cot, flipped a coin and I lost. Did not sleep worth a shit on that thing.

I think he was scared that his hands might roam. I would have been totally OK with that.
I would not have been down for a fuck, but mutual handjobs would have been fine.
I regret what fun could have happened!

Thanks for sharing that, hindsight is always 20/20
 
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samandtham

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Mine was with a work friend. We were at the same company in 2008 and got sent to many work-related trips together—he did sales and I did project management. Whether by convenience or genuine connection, we hit it off as friends during our time together. He's charming, good-looking, and most importantly, the type of guy who leaves an impression on someone, despite his 5'5" stature. He's also been very open (to me, at least) about his sexual adventures with both men and women. I wasn't fully aware of my bisexuality back then and would only listen to his stories without offering any of my own.

Two years later, he quit and moved to Hong Kong and found a more lucrative career there. I left the company not long after that, for reasons unrelated to him leaving. We tried to keep in touch, but as with many friends who find themselves separated by the ocean, the calls became less and less frequent, and conversations were more about reminiscing than talking about the present.

He sent me a message four years ago that we was going to visit his mother in California. I jumped at the chance to invite him to visit me. He said he didn't have a lot of time in the US, but agreed anyway. He was able to set aside two days (the most he could do) and gave me the freedom to plan out his time in NYC. I booked a hotel in midtown (I figured it would be better than having him stay in my tiny studio close to an hour to Manhattan) and put together a very touristy itinerary for him.

(In case you were wondering, no, up to this point there was no other intent from me besides catching up with an old friend.)

First day was uneventful. I picked him up from JFK, we had steaks at Keen's, and went to the usual places a tourist would want to see—Times Square, ESB, the 9/11 Memorial Site, Central Park. He was still reeling from jet lag then, so he promptly crashed once we got back to our room, which happened to be a King bedroom.

He woke up early the next day—again, jet lag. I don't know how long he has been up when he roused me in his underwear to ask if he can use the bathroom. I had no idea why he asked, but whatever. I went back to sleep and he drew a bath.

His last day in the city fell on a Saturday. I thought of doing more sight-seeing in the morning but this time I'll bring him to a club in the evening. Figured he might as well have fun.

I proposed the idea while we were taking a break in the afternoon. He asked me if I knew of any bars where he could meet guys. I suggested a few from a cursory Google search, and settled on a club.

We grabbed some food and then made our way to the bar around 10 p.m. I was actually quite surprised that he's still up. The day previous, you can tell he was ready for bed around the same time. Inside, he got a second wind. He was working the room, talking to everybody, and getting a few shots bought for him as a result. I'd check up on him every now and then, but for the most part, we weren't together at the bar.

Close to midnight, he came up to me and asked if we can leave. He's had one too much to drink. A guy was behind him—possibly someone he had been talking to—and was offering to take him back to his hotel. I declined and said I can bring him home.

Once we got to our room, took off his clothes and laid spread-eagle in the bed. I wasn't ready to call it a night yet so I let him have the bed for himself. I made myself a pot of tea (I used to have one of those collapsible tea kettles that I brought everywhere I traveled) and was trying to wind down when he asked, no, mumbled, if I was going to join him in bed. As he was saying this, I noticed he was stroking himself. I knew he was drunk and I knew what he was trying to imply, but I will never take advantage of such a situation. Basically, I watched him as he pleasured himself—he even stopped a few times because he was between being awake and asleep. Once he finished, I cleaned him up, then scooched him over, and fell asleep myself.

I heard him draw a bath the same time the next day. We had breakfast, and I took him to the airport for his flight back to California. He gave me a long kiss on the cheek as we hugged to say our goodbyes. He also said "thank you for taking care of me." Whether that was in reference to me showing him a good time in the city, or more specifically, that he was fully aware what transpired the night before, I don't know. Neither one of us has brought it up. And although we're still in contact until this day, our conversations are brief and mostly on the subject of us visiting each other again in the future.

If and when we do meet up, I wonder if things would be different.
 
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2484451

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Was in my teens, had a crush on this kinda punk kid, bleach blonde hair. Thought he was the cutest fucker I’d ever seen. His friend group and my friend group join together and now we’re big group of friends.
Some of us (as teens do) decided to get drunk one day, in a forest.

we all start drinking and punk guy (presumed to be straight) ends up making out with me! and not like “oh haha I’m straight and I’m gunna make out with this other dude” no. Like full on make outs going on. (Found out later he had fooled around with his guy best friend)
Well I started grabbing at his crotch, basically feeling his dick through his pants. I’d say he was average size if anyone cares about that.
The drinking continues and we all just have a great time the rest of the day/night.

Next day I get a text from him and he wants to come over, continue what we started and go a little further. We talk about our cocks a little, WELL, Im down I say, obviously.
I waited for the day we planned for him to come over.
Well then literally 10 minutes before he was to come over he chickens out, “can’t make it because blank blank blank”
Damnnnnnnnnnnnn.
Kissed a few times after that but never really spoke about bjs again. I understood tho he was nervous, it happens.
sooooooo badly wish it would have happened but! ‘‘Tis life.

All my friends have always known I am gay. So I have got a few stories like this, thanks to some open straight/bicurious friends. I’m like their gay tester or something hahaha!
 

mraz08

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Have this friend since high school. We didn’t talk much while we were in high school but ended up going to the same college. We grew to be very good friends in college until one semester he doesn’t return. We spoke occasionally on social media but that was basically it.

Fast forward a few years and he posted on social media that he is needing a place to live (bad situation with ex-girlfriend) so I offered my spare bedroom in my apartment. Before he moves in I let him know that I’m bi and will bring guys and girls over. He is totally fine with that, but shares that he had a guy friend very forcefully try to initiate some sexual things between them even though he insisted he was straight. So I figure nothing would ever happen between us. He moves his things in but doesn’t have a bed and won’t be able to get one for a few months, so he ends up sleeping on the floor in the spare room. I didn’t think he would go for sleeping in the same bed as me. But more often then not, he would come lay on my bed just as I was getting ready to sleep, but never stayed.

There were also many instances of him walking around the apartment in just his shower or boxers. One of the biggest missed opportunities was when a mutual friend between us randomly sent him a snap of his ass in his Halloween costume. Roommate wanted to send him an ass pic back and wanted me to take it, but then he backed out.

Another time was when I showed him a video on my phone, I received a message from a friend who sent me a dick pic, roommate was very interested to know what I was going to send back but I was so embarrassed that I quickly changed the subject.

He has since moved out and has two kids but just recently we’ve been planning a bachelor party together, some of the items that he wants to partake in; strip club, day spa, and a massage parlor where they give happy endings. Maybe my chance to do something isn’t over yet!
 

MilfBanger78

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back in high school, a buddy of mine who lived like 3 houses down would sleep over at each others houses sometimes on the weekends, playing video games etc all night then sneak porn. we were virgins. We had jacked off together a few times after school but didnt touch cocks

We were just so horny n frustrated that we dabbled with the idea of sucking each other just to see how it feels. we wound up jacking each other off with lotion never got to sucking. lol
 
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Outofbrooklyn

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It wasn't an almost encounter, but more of mixed messages, he sends me really dirty texts 'as a joke', which he knows I like anyway and also sends me so many amazing pictures where I can see the outline of his massive dick, but we are both to shy of eachother. I can share the pics if necessary ;)
 

maxmax25

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It wasn't an almost encounter, but more of mixed messages, he sends me really dirty texts 'as a joke', which he knows I like anyway and also sends me so many amazing pictures where I can see the outline of his massive dick, but we are both to shy of eachother. I can share the pics if necessary ;)


Yeah would be hot... Does he guess you would like to do something with him?

Maybe just return a dick pick of yours and tell him he had be the wrong adressee