Ever had sex with your best friend and wondered what would happen to your friendship?

So my best friend is over literally everyday. During summer I turn my garage into The Bar. Several games , couple tv's and of course a bar. Behind garage have a pool. Through the years we've gotten use to saying screw it with clothes and just move from pool, to bar , to yard/firepit. He's always been the straightest person I know. I live 1 1/2 from Michigan line. We went there to get some weed( still blows my mind it's legal). I hadn't smoked in well over 30 years( truck driver) . Well recently had health issues and driving is done . I know, move on already. But have to get picture. Because I couldn't smoke he never did around me. Yes you can fail a drugg test from second hand smoke. Well started off usually, had a couple cocktails , maybe game if darts and clothes off jump in pool. Well when we went back into garage ,he rolled and fired one up. Being as I said 30 plus years since I've been high I had forgotten what it does to me .
I get horny as hell. If no sports we want to watch we usually have porn on tv's. It was off when we smoked one, but I turned on . Usually it girl/boy or lesbian. This time I looked for bisexual couples. Figured we get lesbian and guy girl. My ex and I did everything so I do like but up til now never put on. As it's playing we're throwing darts when it showed man blowing other. Was expecting him to say something because was very early in movie still. Instead he said nothing but stared at tv. And gradually grew a hard on. I was mesmerized watching didn't notice I was hard too. Thinking and doing are to different things. I've seen him and "thought about things", but never did. Been best friend 40+ years. Didn't want to screw that up. But this time was different. As I'm watching him watch the TV, I can tell he likes what he's seeing. So without hesitation I'm went to my knees in front of him. As I grabbed his cock nice amount of precum came out. I wasn't wasting it so immediately put his cock in my mouth and just went at it. He came in three minutes, and shot a huge load. As I stood up, he dropped down and sucked me off. He was terrible at it, but something about it was amazing.

So many memories about this. One day, I was hanging with a friend at his house, talking sports, women, having a few beers (and I'm acting like I'm enjoying them) and he announces that he's horny, sheds his shorts - he's in commando mode - and starts jerking off. I'm just sitting and watching him, mildly stunned because I'd never seen this behavior from him before. He's not drunk... that I can tell but, okay, something's up with him because the guy I know is one of those guys that if he goes into a men's room, he looks for a spot to piss where no one can see his dick and something I've laughed my ass off over and good-naturedly busted his ass for. And here he is working hard to get himself off and failing; he's muttering, "Come on, come on..." over and over and I think... fuck it. I get up from where I was sitting, politely removed his hand from his dick and replaced it with my mouth.

I can tell by the way his body tensed that he's surprised and shocked; I kinda peek up at him and he's got that "what the fuck" look on his face but he makes no move to make me stop. He pops his cork a couple of minutes later and after I had to kinda keep him seated; he's calling Jesus and as I'm swallowing his hoppy-tasting cum, I'm laughing to myself and thinking that Jesus can't save him. He goes soft, I release him and go back to where I'm sitting. He asks, "What the hell, man?" I shrug and say, "You were struggling so I helped you." Yeah, that "you don't look like the type" shit and I threw it right back at him and said that I didn't think he was the type to let a guy blow him and pointed out that he did nothing to stop me. He says that he doesn't think we can be friends any longer and I shrug and say, "Okay; no good deed goes unpunished..." and I get up to leave but, ah, he wants to know where I'm going and I say that I don't hang out with people who aren't my friends.

We talk. I'm indifferent at this point but I'm being polite. He's... calmed down. Has another beer. Um, do I think I could to that again for him? I say sure but what's in it for me? He knows what I mean and he balks and I see the moment where he says "Fuck it" to himself and agrees. We're draped all over the sofa and 69ing and for someone who had said that classic "I've never done some shit like this before," he's doing a masterful job of sucking my dick. He cums again; I'm about to and warn him and he stops and jerks me until I cum and probably all over his face.

Now he's like, "Maybe we can do this again some time?" I say we can if he wants to because this is just something friends should be able to do for each other. He fucked it up, though, by demanding that I come over and blow him and I needed to drop whatever I was doing and... bye-bye friendship because I don't play that shit.

so this I don?t think I have shared before.. I have worked for the same company for the last 20+ years.. it affords me a lot of leeway when it comes to travel.. my rout takes me all over the western states.. so about 6 months into this job,, I was in Albuquerque and had been having fun with the guys there.. I think it was the second night there and I had a very sexy gentleman in my bed.. I was on all fours and giving up my pussy to him.. when all of a sudden we hear someone at the door working the lock.. he asks if I am expecting anyone.. I told him to keep doing what he was doing that it was probably a drunk that lost there room.. next thing I know the door swings open and in walks my boss!!! There I was on all fours my pussy in the air my back arched an my head on a pillow.. the guy I was with was balls deep in my pussy.. we look at each other and I know that my job was over.. the guy that was fucking me never skipped a beat and just said come on in the pussy is great.. my boss stands there to what seems like forever an says: I think I underestimated your negotiating skills!! Then laughs!! Next he walks over and smacked my ass.. then he puts a finger in my mouth and just says suck.. so I did.. very shortly there after I had his thick 8? cock in my mouth.. so there I was being spit roasted by the very sexy guy I picked up in the hotel bar and my boss who just dropped by to see how things were going.. they tag teamed me till the wee hours of the morning.. they both filled my pussy a couple times before my guy from the bar left.. then he told me that it was time for some personal one on one negotiating training.. I figured that at this point there was nothing to loose so I told him I needed a min to freshen up.. so off to the bath room I go.. had a quick shower and douched myself out.. oiled myself up from shoulders to toes.. I found in my bag a pair of stockings and a garter all lacy and silky.. took a big breath and went back to the bed where he was sitting in the middle of.. he looked at me and smiled and said wow!! I got up on the bed and sat on his lap facing him. Put my legs around him and started kissing him.. we made out for a bit then I felt his fingers entering my pussy.. this sent shivers up my spine.. and my back involuntarily arched to allow him to finger me while we kissed.. Then he ask how do you negotiate one on one?? I gathered up the pillows and placed them behind my back and simply laid back legs spread and said talk to me.. he laughed and ask do you ever give a guy a chance.. I told him not if I don?t have to.. we must have fallen a sleep while we were fucking.. as I woke up when his cock fell out of me with him still on top of me.. the next day at breakfast he told me that I never had to worry about my job and that we were going to travel together quite a bit.. and we did.. over the years we spent many a trip to gather.. about six years ago he got married so our traveling together pretty much came to a halt.. we did have a few moments here and there but nothing like before.. he was my first real love interest as far as a guy goes.. I would have married him.. we are still very close but I haven?t been with him in over a year.. he is going to retire next year.. says his son is taking over.. won?t be the same around there..

Wow, that was quite an experience and hard to beat. That was an awesome outcome too.

Had a college buddy that we would travel to National parks together to backwoods hike and camp and had many missed "would be perfect" opportunities in tents and hotel rooms. We've drifted apart since but we were both vulnerable back then and I think if we acted we could have handled it. Hindsight, right?

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Originally Posted by seattle_guy50

Had a college buddy that we would travel to National parks together to backwoods hike and camp and had many missed "would be perfect" opportunities in tents and hotel rooms. We've drifted apart since but we were both vulnerable back then and I think if we acted we could have handled it. Hindsight, right?

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Most of the time 20/20 but not always.

I know a lot of guys who realize that they could have done it with a friend - and the friend knew it, too - but nothing happened and... shit. Missed opportunities like that just... messes with you. Lots of "what if" stuff banging around in your head. It's like... you know it should happen; you can feel it "in the air." And... it doesn't for some reason. Damn it! I've been in this situation with friends and, yeah, we gotta do something and... we don't. The moment passes and, like, the next day, we talk about, find out that we both wanted to, but we were both afraid to say something to get it going. Sometimes we did what we should have done the other day but usually, nope. The moment came, the opportunity presented itself and, the moment passed.

Oh, well...

I had a best friend that was 4 years older than I was. One afternoon we were playing in the woods and he told me he felt horny. He removed his pants and underwear, and starter stroking his cock. It was a beautiful cock, and I watched, as he got into it. Come and give me a hand , i won't tell, he asked. I sat beside him and jerked his hard cock. Don't be afraid to put your mouth on it, he instructed. I lowered my head and put it in my mouth. Ummm that feels so good he replied. Suddenly he started throbbing and pumping cum into my mouth. I didn't know what to do, I swallowed it all. I kept sucking him as he went soft. I promise you, I will never tell, that would make me gay. He told me that I did a wonderful job, and he offered to return the favor. I was still in shock of what I had done, and refused. He told me that we would do this again, and we did. We progressed from mutual masturbation, orally sucking each other, to fucking each other between the legs, to actually fucking each other. We continued for years, until we separated when I joined the service. No regrets, I still enjoy sucking cock!

Yes I did ,for 4 years up until we were 17 .
It all started out ,we were skinny dipping and and sitting in the shallow water and he told me if I d stand up he suck my dick.
So I stood up and he took my cock into his mouth a started sucking it ,I pulled away and sat down ,then he ask me to lay in the sand and let him bury me ,so I did .
He covered me in sand except my head and cock ,then he went down on me and sucked my 8" cock while I laid there for about 15 minutes,then he said it was my turn to do him .
So I wash the sand off of myself then I buried him in the sand and started stroking his hard 7" cock ,he beg me to suck him but I wouldn't and that went on for a year while he continues to suck my cock.
But when we were others playing hide n seek at night with others he ask me ,if Steve sucked my dick or if Billy did.
After a year I gave in and went down on him and it wasn't long before others knew I was and he was me .
We got busted by his older sister in a 69 and I was sent home I do think my parents found out, because my mom got weird but anyway.
It turned into to only me sucking him most of the time til we turned 17.
It got spreader around and by the time we were in our early 20 everyone knew ,it cost him the love of his live and me a wife and a lot of freinds and humiliated both of us .
He left and went to Alaska and I traveled for work for years and it's never really gone away.
I tried in 2012 he was helping me roof a house and I adh him about it ,and he said no because I had to run and tell everyone and I never told anyone,it was all him and his cousin Steve that ran thier mouths.
Found out shortly after that his mom had been having sex with him and his brother since his Dad's accident when we were 14 and his brother had been sucking my brother and his other friends .
Pretty crazy.
I started hooking up with guys again in 06 after my 2nd wife and I split because she was just a flat out whore.
So I became a whore with both guys and women.
I have been with over 200 lovers both male and female.
Married again and settled down haven't been with a guy in over a year now ,but it's hard to hook up out in the sticks any the wife is always around , because I am disabled due to my heart.

First sex of anykind was with my best friend. Went on for about two years and that was it. Moved on. Havent seen him in decades

not to long after I moved to Phoenix.. I met a guy named Gary.. we were almost instantly best friends.. we did everything together.. well most everything.. I had moved to Phoenix because of sex with men.. and the doctor that I went to to transition was there.. Gary had no clue what I was up to.. I had a big crush on him.. I dropped a lot of clues to him about my wanting him.. like I said he was clueless.. so about a year into transitioning and my body changing breasts at that point mostly and shaving my body..I couldn’t stand or hide it much longer.. one night he came to my place an I was with another guy,, I had makeup and my long hair done up.. I told him I was busy and would talk to him later.. he wondered why I wouldn’t let him in.. I told him I had company.. anyway the jig was pretty much up.. I called him later that night and he came over and I told him everything.. he laughed at me and told me he already knew.. said he had found out from one of the guys I had hooked up with a few months earlier.. just didn’t know how to tell me.. I told him I had a big crush on him,, he told me he had one too.. we had amazing sex for about a year.. and I made a full transition.. I had gone from being his best guy friend to his girlfriend.. then he got kinda weird and started demanding things be certain ways.. thins just kinda fell apart.. we separated and we never really got back together..

@Tight1-4u, yeah, that's the problem having sex with a friend and how some guys have sex with you... and now they think they own you. Being pushy; making demands and getting pissy when you ain't feeling that and... there goes the friendship. Like, I didn't end my friendship with my son-in-law when he wanted to know what it was like to suck dick with a guy and I got to be that guy he wanted to do this with. It was fun; I could get him to cum being sucked (and giving my daughter the bizness because I could make him do something that she couldn't) but then he started getting pushy and demanding and, oh, hell, no. We stayed friends and still his father-in-law but no more sex between us. He didn't like it but that was his fault and every time he'd mention those times and how he wished he had behaved better, I just remind him that he fucked up this good thing and there's no going back.