[F] 21 My New Year’s Eve Recap (aka my roommate paying up and my first lesbian experience)

Ok so as promised here’s the update from last night on the streaking bet I had with my roommate (who we’ve decided to call E, that she lost) and as the title says the very interesting events after… Bear with me cause I’m super fucking hungover right now and there are parts about last night that I straight up do not remember.

Ok so a few weeks ago E and I made the decision to host a party in our ok sized 2 bedroom apartment. We’ve had some parties before with no more than 10 people and it worked out fine and since most people were still out of town because of break and Covid. It ended up being myself, E, S (our friend from other stories), one of S’s housemates and Sorority Sisters (we can call her R), my really close friend S2 (yeah the anonymity here might get a little confusing) and her boyfriend, our friend L and her boyfriend, and two guys who live nearby and one of their girlfriends (all three of which will remain without a pseudonym for a variety of reasons…). So with 11 people total it was a really full apartment lol.

Now part of E’s punishment for losing the bet in addition to ringing in the new year in her birthday suit was to try and convince others to join in with her. She had been trying to get me to join her ever since she lost but I was not going to give up on the opportunity to bask in her embarrassment. A few people came over at 8ish (S,R,S2,L and their respective boyfriends. S knew about the bet and had told R so it was fun to watch E elaborate on it to R and R to flat out refuse to do it. S said she was on the fence and would take some convincing. It was the first time L and the two boyfriends had heard about it (I had told S2 about it prior). L said she was in immediately and volunteered her boyfriend. S2 seemed unsure (mostly because it was down the street not around a building like a naked mile) and her boyfriend said he would only do it if she did.

Now the other three were the really fun ones to watch her try and convince since this was the first time either E or myself had met them in person (one of them lives in the neighborhood and is friends with S and R and since they didn’t have anything better to do NYE I made sure that S convinced them to come). Let’s just say it was really exciting that they decided to show up and that was really cool and leave it at that. Now they got their a little after 10 when the party was in full swing and we were all pretty drunk already especially E (who is all of 5’2” and like 100lbs). So it was hilarious to watch her explain to these three strangers (all of which even the girlfriend are over 6’ tall) that several of us would be streaking at midnight and that all three of them should join us.

Well it was quite clear that the one without the girlfriend was interested in seeing some girls running naked down the street and after some convincing from E (which consisted of her sitting on his lap very unsubtly) he agreed to join. This is where my memory starts to get a bit fuzzy. I remember those that were streaking agreeing to go just after midnight so that people could watch the ball drop and all that jazz. I remember the countdown and shooting off some of those cheap confetti cannons.

Now as the party was mostly couples everyone pretty much had a midnight kiss lined up (E chose the distinguished guest that she had convinced to join her as part of her bet). Again I’m really fuzzy on how it happened but I know someone had joked that S and I should kiss at midnight since neither of us had anyone and lo and behold with the confetti falling I found myself kissing S. It wasn’t anything crazy but it was more than a peck on the lips which I remember finding odd.

Very soon after that I remember E standing in the doorway in her Bra and Thong telling everyone that was doing this to come along. Everyone who wasn’t participating decided to stay up and watch from the balcony. I decided that since it was my bet I wanted to watch it from street level. Now E was the only one bold enough to wander down from our third floor apartment half dressed. Everyone congregated at the corner of the building (which is also the corner of the street). E was easily the first one naked with her head start and was eager to take off, but stood there covering herself feigning embarrassment. L and her boyfriend had followed through with joining as well as E’s now apparent date for the evening. Now I’ve seen both L and her boyfriend naked before (they were apart of our cards against humanity game) and I wouldn’t say either of them are insanely attractive (but if you’re into curvy girls or guys with a dad bod they are your couple). Now E’s date is a big athletic guy who had absolutely nothing to be embarrassed of (that was clear even in the dark and cold) though he did his best to keep himself covered the entire time.

The two surprises were S and the girlfriend guest. Idk when girlfriend guest decided to participate so I was quite surprised to see her stripping off with the rest. I was not as surprised to see S there but I was surprised when she started stripping she did it right in front of me and the fact that of all of the people that were there she was the only one who didn’t cover herself in anyway. Like at all.

Now I want to say that before any of this I’ve never been that attracted to girls. I’d make out with people at parties to mess with guys and on dares, but never really more than that. I also want to say that I can objectively tell if a girl is hot or not and S is an 11/10. Easily the best tits I’ve ever seen (including my own).

Now the group took off together running naked down the middle of the street (everyone was completely naked except the girlfriend guest who kept her thong on which as those of you who have followed along with these stories is always a subject of much debate). L and her boyfriend went the shortest distance only running to the end of our building and back. The two guest didn’t go much further than that turning back around shortly after L.

Now the entire time this was going on all of our friends are screaming their heads off from the balcony which draws the attention of others in the building so by the time the first four streakers made it back there were at least 5 balconies of people watching them get redressed. It’s impossible to tell how much they could see (though with the street lights and my experience of sitting out on that balcony watching cars drive past at night it was probably a lot definitely enough to know they were naked).

S and E though both ran the full length of the block and back. E because she had to due to our bet and S just for fun I guess. The both really only lightly jogged the whole way. I’m not sure why E didn’t run faster (maybe staying covered up slowed her down?) but S only jogged I’m pretty sure because otherwise her tits would’ve been bouncing around to much and she seemed to refuse to want to cover them up for some reason.

E got back first and quickly redressed there on the street corner into her underwear being sure to look at me and say “enjoy this now cause I’m gonna get my revenge yet” it was playful and we both laughed but I’m pretty sure I’m gonna have to be careful what I bet her in the future lol. S got back and picked up her clothes before carrying them around back to the staircase to put them back on. I followed her since she was the last one and watched her get redressed at the bottom of the stairwell where she expressed her disappointment that I hadn’t joined her yet again.

Now this is where I really have a hard time remembering details (and I normally never blackout so that’s how I know I was wasted). I know the party resumed in full force with music and dancing. E kept taking her dress on and off and (I don’t know why but I know it happened cause I have the photo of it…) all of the girls flashed their tits for a photo. All in all it was a pretty great fucking party that really died down when L,S2 and their boyfriends decided to head home (they all live together). Shortly after we realized that E and the single guest had “disappeared” and the other couple offered to drive R and S home. R happily accepted but S said she wanted to stay and help me clean up.

Again it’s all a bit fuzzy but the next thing I remember is that S is on top of me on my couch and we are full on making out. Like I said this is completely new territory for me as she’s feeling me up and I’m very into it. I’m not sure how it happened (I think I remember her saying that I got to see her naked and now it was her turn cause it was “only fair”) but right there in my living room I’m standing there completely naked as she starts to suck on my nipples and started to rub my clit. All the while while this is happening we can hear E (who is a screaming) just getting absolutely railed in her bedroom.

Eventually S and I find our way to my bedroom where she starts going down on me. Now it could have been the alcohol or how turned on I was from making all of those people streak (I was practically dripping wet from midnight onwards) but this was hands down the best oral I’ve ever had. Now I have no clue how long she went down on me for but eventually I realized it was my turn to reciprocate. Getting her naked and on her back I was incredibly nervous (like sobered up nervous) cause I’ve never done this before. Basically I just tried to recreate what I like which was diving in tongue first doing as much with her clit in clockwise motions as I could and reaching up and squeezing those fucking amazing tits of hers.

Now I hope she enjoyed it (and I think she did) cause I’m pretty sure she came after which she said “fuck! I wish we had a strap on.” Now something I have never confessed her is that my last long term boyfriend loved to be pegged. We only ever did it when I was feeling super dominant and him very submissive so I do have one strap on that I bought for that specific instant.

This is when I fully took over. I between the streaking and the bet and the fact that I’d won I was feeling very dominant. I made her lay spread eagle on my bed as I found the strap on (it had been awhile since I used it) and put it on. All the while I mocked and teased her about her streaking and how embarrassed she must be. I used lube mostly out of habit but by this point she was so wet I probably didn’t have too. It was really incredibly hot to watch her writhe underneath me as I thrust into her and to listen to her beg and moan my name (I now know why it turns you guys on so much). After awhile it got to much for me and I needed some sort of release so I pulled out of her, discarded the strap on and sat on her face while she ate me out again.

I don’t remember us going to sleep, but the first thing I remember is waking up as the sun rose to her tits practically in my face and trying to remember as much of last night as I could. After sleeping some more we both got up (and if I’m being completely honest I went straight to the bathroom and started puking my guts up). Though I did get to see the look of surprise on E’s face when she saw S walk out of my bedroom to make her walk of shame home. E’s man had snuck out before any of us woke up but he definitely left an impression on E (she still isn’t walking straight lol). My tits are covered in hickeys from S.

I’m about to go and see if the hangover has subsided enough for me to eat something solid without puking it back up. Ill also probably have to explain the whole night to E who I think is probably dying to hear about my hook up as I am about hers. I also have no clue what to say to S now cause that’s all sorts of weird… but yeah. I figured I owed you guys an update so here it is.

Source: reddit.com/r/gonewildstories/comments/kol29s/f_21_my_new_years_eve_recap_aka_my_roommate