Almost went all the way with boyfriend and his bestie

My boyfriend (I'll call him B) has a best friend (I’ll call him D) who lives in the apartment across from him in a very small building mostly occupied by college students like us. I was over at B’s one evening, chilling on the couch and watching TV, wearing yoga pants and a sheer lace top with a dark, busy pattern that I though provided some modesty.

D knocks and walks in to chat with B who pauses the show. D is very, very nervous as he talks, looking out the window instead of at us, so I figure my top must be more revealing than I thought. I look at B and he looks back at me with this crazy grin on his face, glancing at my chest. He’s noticed D's nervousness too.

He asks D to close the door and as D walks over there he whispers in my ear, “take your top off when he sits down.” I whisper back “what?” and he nods and mouths “trust me”. D turns around after closing the door and B asks him what’s wrong. D's like, no, nothing, still only making quick glances at us. B tells him to sit down and relax and D hesitates, since there’s only the couch to sit on, but then walks over to the empty seat.

I wasn't sure what to do, but I didn't want to ruin whatever B had planned, so as D turned to sit down I whipped my top off. D sits down, sees my naked chest, says “whoa” or something and turns so he’s staring at the door. So now there’s this awkward moment with D looking at the door and me sitting there with my boobs out and I’m thinking if this is some kind of prank at D's expense it’s not going well.

B tells D “you’re so tense, man, relax” and “it’s not a big deal, just look”. So D looks at my chest again and then up at my eyes and he still looks really nervous. B then starts caressing my boob and tells D again that everything’s okay. D is now staring at my boob as B plays with it.

This is all kinds of weird and awkward but as B keeps reassuring D while playing with my boob and D just sits there staring I start feeling kind of disconnected from the whole thing, like I’m watching other people do this. B stops and asks to see D's hand. D holds it out like he's getting his palm read and B takes it and places it on my other boob, holding it there until D gives me a squeeze. Now they're both fondling my boobs and I lean back and close my eyes because it's actually starting to feel good.

B kisses me and I kiss him back passionately as D starts kissing my boob. D moves up, kissing my neck, and I turn and place my hand on the side of his face, raising it up so I can kiss him. As he and I start making out, he continues to fondle me as B pushes my top off my lap and starts stroking my pussy through my pants. I'm getting really hot now, kissing D even more passionately. I reach out and find B's dick stiff in his pants. I stroke it then reach out with my other hand to stroke D's dick. B takes his out, then D does the same, and now I'm slowly pulling the two of them off as they continue to touch and kiss me.

It was the craziest thing I'd ever done till then. I felt so turned on and realized that this was probably going to end with me fucking both of them, and that I was actually looking forward to it. Or I thought I was.

B started trying to pull down my pants, with difficulty since they're tight and D was almost lying on top of me at this point. I was kind of startled back into reality. I pushed D off of me and said, "okay that's enough", pulled my pants back up, picked my top off the floor, and made a sprint to the bathroom.

D was gone when I came back, but I ran into him in the hallway the next day when he apologized. I told him everything was fine, that it had been fun but that I'd just reached my limit. Same thing I'd told B when I came out of the bathroom, after he sort of apologized and explained (again) that he likes to explore and try different things, sometimes not thinking them through first. I told him that was cool as long as he accepted my limits, which he said he always would. I didn't tell him that I would've gone further if he'd taken it more slowly, and I also didn't tell him that I was kind of excited to see what he would come up with and how I'd feel about it.

Feb 16

Related Posts


  • newest
  • most popular
  • oldest
    • So very hot! This is a huge fantasy of mine. I know my wife would probably be down for this, unfortunately, i don’t have any close friends that live nearby.

    • Where do you live?

    • My young wife, my bud and I were drinking. She danced with each of us. Sexy conversation...
      Bud had been hot for my wife for 3 yrs. Wife notices...kind of enjoys the attention of a 2nd male.
      We play strip Monopoly I make up sexy new rules. Wife ends up standing as bud strips down her short-shorts. Then she does the same to him. She has to take turns kissing us. I remove her top. (she's braless, as usual - small breasts)
      She gets both of us naked. Then slow dances with bud - they kiss a little. Both get handsy....He pokes her with is boner - she stops, Takes his penis, pushes it down - spreads her legs and captures him between her legs against her pussy.
      They stop dancing - grab each others butts and begin to push themselves into each other. (I thought they were fucking/standing, but as she turns I see the head of his dick between her butt cheeks. They are dry humping each other. Well, not dry - I'm sure she's adding wetness to the situation down there!)
      She cums....he cums - out onto the carpet and down the back of her thighs...
      They come back to earth.....she kisses him goodnight and goes down the hall to bed.....telling us that this has "gone as far as" she wants it to go.
      It was crazy, we stop.
      The next morning, over coffee things are OK - maybe less sexual tension now between the two. He has a girl take care of his 'needs' without my wife. They've 'experienced' each other's bodies.
      It was a one-off - 6 years ago.

    • Are you sure? They could have met/be meeting surreptitiously.

    • You should have been tagged teamed by both. Filling you with cum. I know i would have lol

    • I wish I had went through with it now

    • Never pass up chances like that. My cousin and i were in the same spot as you with his gf. She wanted to know who was better in bed. She found out the hard way after she got 2 big Italian cocks in her for 6 hours lol

    • Yes if I could do it over I would have had two hard cocks in me at once

    • I can fill you up babe lol
      Anthonytaormina1959 gmail if you want to chat

Account Login
Is this post inapropriate?
Reason for reporting this post
Report this comment
Reason for reporting this comment
Delete this post?