This was from a fun night a few years ago. Sorry in advance for the long story!
I was working a summer job during my undergrad with a bunch of other students. The pay was shit but I made some really great friends who I still talk to, to this day. Though I got along well with most of my coworkers, there was one who was my closest friend. Let’s call him Josh. We talked basically all day at work, ate lunch together, texted each other when we were home. Had a lot of shared interests and the same fucked up sense of humour.
We were all in our late teens or early 20s so we were always buying cheap liquor and crashing at our friends’ apartment. On one such night, a bunch of us were drunkenly hanging out at our friends apartment. Me and Josh were talking on the balcony and at some point we started making out. He was grabbing my tits through my shirt and I was rubbing his dick through his pants. We drunkenly stumbled into the bathroom and I gave him a blowjob. He told me he loved me right after he came (?) and promptly passed out on the spare bed in the apartment.
I was still awake and went back to the party. Another coworker, Brian, who I knew had a thing for me started chatting with me. I thought he was cute and charming and would flirt back, but he along with the rest of my coworkers knew about how close me and Josh were. We ended up talking for a really long time, the guy who owned the apartment went to sleep in his room and the rest of our friends passed out on couches in the living room. I was getting sleepy too so I told him that I was going to sleep in the same bed as Josh. Brian said he didn’t want to sleep on the floor and he asked if it’d be ok if he slept there too. I said it’d be fine with me.
Josh was still completely knocked out when we got into the room. I slept in the middle, with Josh on one side and Brian on the other. Brian and I ended up spooning because it was the only configuration that worked. I liked the way he felt behind me, so I did that cheeky thing when you wriggle against a guy’s crotch while spooning. He started kissing my neck, and whispered in my ear that he wanted to make me cum. He turned me around and started making out with me. With Josh passed out right next to me!! Brian started fingering me and dirty talking to me about how much he wanted to fuck my wet cunt. I didn’t realize how much I was into dirty talk til that night and it made me SO wet. That combined with his incredible finger work made me squirt. I had never squirted before, either by myself or with a partner.
I was ready for round 2 so we moved into the bathroom. Now that he had a bit more room, Brian started eating me out. He was so good with his tongue and I was dripping wet in no time again. He started to finger bang me while he sucked on my clit and I squirted again, all over him. He then laid down on the floor and asked me to ride his face. I hadn’t ever done this with a partner and it was so fucking hot. I came again.
Because he had drank so much, he wasn’t getting hard. I really wanted him to fuck me, but he was doing such a great job with his mouth and hands, I had no complaints.
We went back to the bed, exhausted. We fell asleep spooning.
Cut to the next morning. We all wake up extremely hungover and in my case, very dehydrated. I tell the whole story to Josh who took it really well and honestly found it hilarious that he didn’t wake up for any of it. The 3 of us didn’t do anything that morning together (though I wish we did). Our other friends were less knocked out than Josh and high fived me for bagging 2 guys in a night.
After all that, Josh and I actually ended up dating for 2 years after this hot mess of a night. After we broke up (it was very amicable, as he was moving to another part of the country for good), I did hook up with Brian a few times. Never led to anything serious, but he was still damn good.
Source: reddit.com/r/gonewildstories/comments/m7ejoy/i_hooked_up_with_2_coworkers_in_1_night_fmfm
Well done, both in the story and writing it