[MF] Time I [M] slept with my best friend/roommates ex [F] [part 1]

Some quick setup here; This was back around my 3rd-4th year in college. I was roommates with my best friend since grade school, after my initial year in the dorms, then a year in the fraternity house, and old friend transferred to my university and we rented a house. My friend, let’s call him James, was a serial relationship guy. Ever since grade school he’d always had a girlfriend. He and I were sort of opposites in that sense, as I just never focused on settling into anything until post college; just wasn’t a priority for me back then.James and I surely shared some crazy dating scenarios growing up, and especially with his choice in girlfriends.

One short story that connects here was a night I crashed at James’ place after I had gone to a party with my football teammates and didn’t want to go home after having alcohol breath. His girlfriend, let’s call her Shannon, was always around him and often stayed the night. I came over and literally just crashed (on the floor), but sometime in the night/morning I was awoken to the sound of sex literally happening a few feet from me. I pretended to be asleep, and even recall her multiple notes of concern I’d hear Shannon asking James, to which he reassured her I was a passed out (which I was at the time); But, I was not and heard it all. The skin slapping sounds, the shared moans (half attempted to be muffled), the wet joyous sounds of sex. When he was done, he promptly proceeded to the shower and she was left lying in bed, and I could hear her still breathing heavy. I just couldn’t help myself and said “so was it as good for you as it was for me?” Surprisingly, she wasn’t mortified, but laughed it off. I was much shyer back then, and probably a wiser (riskier) me may have attempted a move, but I didn’t. Shannon wasn’t shy to the bedroom as I pretty much knew all the things she had tried and encouraged with James. I’m certain she would have gladly partaken in more (which I had later gotten confirmation on).

Back to the current story…

Between the time I moved to college and prior to James transferring in, James and Shannon had a fall out. But James had sort of a cycle of keeping exes around and working back through his exes so he had companion fallback. When we moved in together, he had apparently just gotten back together with Shannon from High school. So it sort of felt like old times and there was a familiarity there as she clearly knew me, I knew her; We had spent a ton of time together through the years, and honestly never really had a thing for her. Shannon was always just kind of an extra friend, and now she was like an extra roommate. Through the years she had also, always tried to play match maker for me, and she had some modest success a few times, but I just never committed myself to a relationship.

Fast forward a bit… about a year in living with them, James and Shannon were going through a bit of a rough patch. She’d frequently talk to me about their struggles and I’d always offer an empathetic ear, and talk her through things, and sort of urge her to move on. James was sort of using her for sex and filling a gap until he found a new girl… it was sort of his M.O. and Shannon recognized it, as she’d gone through this pattern once before. One night, as happened many nights I clearly heard them having sex (or attempting it) in his room. Shortly after, Shannon came out clearly frustrated and asked if I’d join her for a smoke on the porch (it was her code for “can you talk away from James”)? I didn’t smoke, but didn’t mind sitting around it… James hated it, so he rarely would come out there. When we got outside, she just started to unload about all the struggles they had been going through and was worried he was already moving on. Of course, I’m reminding her of his patterns, but mainly I’m just sitting there just trying to listen and let her vent. I did ask her about how the sex has been as, to me ”…it surely sounds like you guys are healthily into each other” to which she replied, “Ugh, don’t believe all you hear.” Shannon then proceeded to tell me about their sexual struggles to, and how much of it was on his side, and in this current example how he was too stressed to get a full erection. Which, I did know he was under tremendous pressure because he was a horrible procrastinator (who wasn’t in college though?). It was about that time that he popped out and said he was going to the library to meet with his project team for some work on a class project.

After he left, Shannon and I just continued talking about everything going on, reminiscing on the past and the beers were flowing easy, and we got a little buzz going. Through the reminiscing, she actually started to recall the night when I had ’passed out’ on the floor next to her and James having sex back in the day. We had some shared, awkward laughs about it, and she said she just knew I was awake. It was then the conversation really started to take a turn as Shannon told me she thinks back to then and it makes her horny knowing I was there, listening in so close to them. Shannon also started to reveal that it still gets her excited today knowing I’m listening. I’d say I was shocked, but pretty certain I was just brushing it off as I ignorantly never connected it to me (at the moment). Don’t get me wrong, Shannon was attractive.. she was short, like 5’2”, very petite, and with a body that you’d be shocked she didn’t work out. Her best assets were her breast. Shannon’s breasts were proportionally gorgeous on her frame… a decent full handful, but not too big to think “I bet those are uncomfortable for you.” Clearly, This is when the conversation completely flipped from her woes with James, to solely focused on me and I think/know she wanted to get me riled up.

I think she saw my getting kind of squirmy and Shannon pivoted the focus off her views towards me, and she began probing me about my sexual preferences, keenly focused on what she heard from her friends she tried to hook me up with. She clearly was paying close attention to me and my ‘moves’ and our shared sexual behaviors and decorum. We were literally giving an each other a sexual play-by-play of what we’d do together and if I was squirmy before, I was definitely squirmy here as I was getting hard. Shannon totally caught me and called me out for it when she asked me to get us some more beers, and when I attempted to play it off by saying “we don’t need any, we just opened these!” [Coy] She quickly pressed “what?! Can’t get up because your cock is hard?!” [Shock]

My momentary hesitation to answer was all the confirmation Shannon needed, and I swear her foot was like ninja quick and dropped her sandal and was pressing on my hard cock trying to break through my pants. To which Shannon replied “Oh! Well that feels much harder than James’ earlier!“ and then immediately “You feel as hard as I am wet, probably best neither of us get up right now” [Melt]. I was just frozen, not wanting to pull away, and conflicted if I should engage. It was at this point we sort of did this joint ‘check the time’ and neither of us had realized we had been out there for a few hours. We both sort of pulled back, and in that momentary pause, James got home. Shannon got up and went inside and they both went back into his room. By the time I came in, I could hear them going at it with her moaning and being extra loud. Shannon wanted wanted to put a show on for me and it worked. I jumped into my room and left the door open so I could hear and had such a huge release thinking about the conversation and the events that just transpired.

Part 2 coming…

Source: reddit.com/r/gonewildstories/comments/12b0abg/mf_time_i_m_slept_with_my_best_friendroommates_ex