27 Girls (And Guys!) On The Sluttiest Thing They Ever Did

I did what any not-at-all-self-respecting forever alone would have done - I hit Craigslist.

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As seen on AskReddit.

1. ummmitsjames

Had sex with my girlfriend next to my best friend in the same bed. He slapped my ass while I was mid thrust.

2. throwawayslutfucker

Ok so this just happened last Friday. It’s been about 7 months since I’ve had sex, and the dating scene wasn’t going as expected. I got hammered while I was out drinking with buddies, and decided that I was getting laid that night.

I did what any not-at-all-self-respecting forever alone would have done – I hit Craigslist. For those who don’t know, you don’t search the “casual encounters” section on Craigslist when looking for casual sex because it is full of scammers. My best option was a hail mary on the general romance section. I looked for the most casual post that I could find (it very simply stated that she wanted to go out for drinks), and that’s who I emailed. She responded back immediately with her phone number, and from the moment she started speaking I knew that she was a mess.

We agreed that I would pick her up, since she didn’t have a car. Upon picking her up, she offered a blow job but said that we couldn’t go back to her place because she lived with her ex who was cheating on her (made no sense to me either, but I didn’t really care). My place was out of the question because of roommates, so I paid for a cheap hotel (around $40), and a 12 pack of Coors light.

So here I am, in this hotel room, with a female janitor whose face eerily resembles Gene Simmons. She’s completely wasted by this time (started drinking while waiting in the car for me to pay for the room), and spewing utterly incoherent nonsense. At one point she asks me to clean her toenails out with a key, because she likes when her boyfriend does that. Nope. Hell no. WTF?

Finally she gets down to business… but either she did not know how to give a blowjob, or she was so wasted that she thought my cock was an arcade joystick, because she continued to wag it back and forth like she was practicing her ultra combo. I stopped her, and asked to simply have sex instead. She agreed, laid on her back, and made this disturbing grunting noise as I fucked her.

I don’t know how I managed to actually finish with this woman, but I did. I immediately got up, threw the condom away and got dressed. She was still yammering on about her ex when I stepped out of the hotel room without saying a word. I got a call from her a half hour later, after realizing that I left. She left a voicemail that stated, “I need your help, I’m locked inside the room.”

Never again.

3. sluttersmcgee

Threesome with a guest at the convention I work for.

Everyone knew; now I’m getting razzed about it by my staff. They want to change my badge name to “Guest Servicer.”

4. IBangedTwoSisters

I had a friend named K who had two sisters, R and S. R went through a bad break up, so K thoughts she should set us up. Things went pretty good and the two of us started seeing each other on a regular basis. After about a month, we started sleeping together, and things went fine.

Until a few weeks later. We were in bed and she was acting unusual. I asked her what was wrong and she admitted that the day before, she slept with her ex boyfriend.

I was upset, so I went to talk to K. I walked over to her house, but S answered the door, saying that K was out. I was noticeably upset, so she invited me in. I told her about what happened, and she started to rub my shoulder, trying to make me feel better.

We ended up kissing, and then things continued to escalate. We went into her room, and had sex.

5. phenguai

I was on my way to being drunk at the bar when a cute girl started giving me “the eye”. We started dancing and eventually started making out on the dance floor (first time that had ever happened).

We made our way out to my car where we continued to make out. As we are about to leave, her friends come out and drag her away. Now, I had just been kissing her ear and apparently her earring had come off right as her friends were (literally) dragging her away. I didn’t notice it at first, and she was gone so quick that I couldn’t give it back to her, I just put it in my change tray and forgot about it.

Fast forward to about 2 months later, I pull up to a comedy club and as I am parking, she walks by. I don’t know how I managed to recognize her,and I certainly didn’t know her name, but I remembered that I had her earring in my change tray still. I ran up to her and said “excuse me!” and she said “yes…” and looked at me as if she obviously didn’t recognize me. I said “I think this is your earring” and she said “OMG where did you find that. I said “in my mouth” and we just stared at eachother blankly for a few moments. She nodded and looked at the ground while sticking out her hand. I gave it back silently and walked the other direction.

6. neighborhoodrapist

Gave guys handjobs under the desk in highschool

7. JABRONIE_CoolWord

Once I got naked on stage at a strip club and had a stripper sit on my face. Didn’t even get herpes!

EDIT: I did not get pink eye or any other STDs from this incident. Also, I am a girl.

8. ULTRADETH

I fingered a girl on the couch while my dad was in the living room.

9. Coldhate

Had sex with a girl so I could play Minecraft on her computer.

10. [deleted]

This isn’t so much slutty as it is shameless. I was having sex with my ex-GF in her parents basement. Her Grandmother was in town and decided she needed to use the basement bathroom at 3:30 in the morning for some reason. She walks downstairs to see her Granddaughter getting her cervix punched by the head of my dick, doggy-style, by the nice blonde pale boy she had just eaten dinner with earlier. My ex didn’t notice Gram Gram on account of her facing the other way moaning into a pillow. Her grandma stood there stunned waiting for a reaction so i shrugged with one arm and mouthed “Sorry” but I didn’t stop because I didn’t want my GF to know. Next morning her grandma acts like it didn’t happen and my ex was none the wiser.

11. AngryOcelot

I once moved my shoulder so that my hairdresser’s boob touched it.

12. TheGreenBackPack

This is a recent story, and i’m a guy so i don’t know if it counts as “slutty” but here it is: i was recently on a study abroad trip in China for a month and a half. Next to the place i was staying there was a Chinese High School with Basketball courts so i went there every day to play. Everyday i went there would always be this girl there that would watch me, and every time i did something good she would smile. This indicated to me maybe, just maybe she liked me even though we never spoke.

Fast forward about 2 weeks of the same thing going on everyday and i walk up to the courts and see her sitting on a bench texting. Now i don’t speak any Chinese at all so i knew talking to her about anything substantial was useless. So i took out my phone, and do what any horny 20 year old boy would do who hasn’t been sexed in months would do. I took out my phone and google translated English to Mandarin “I think you’re beautiful and would love to have sex with you” and showed her. She saw the screen and just smiled grabbed my hand and took me behind the school and we had sex. I was so surprised this worked, but i also feel a little slutty that it happened.

13. Kaputaffe

Hooked up with three chicks one halloween night … dressed as an oompa loompa! I feel like Reddit could get a nice Oompa song going here…

Oompa, Loompa, macking on you…

14. eeu890

I had a girl that I used to hook up with come over one day to have sex, while also making plans for another girl that I had previously dated and was sort of talking to again to come over later in the evening.

Had really good sex with the first girl, but I just couldn’t get off. No matter what I tried, how good it felt, it wasn’t happening for me. She was a little bummed but I told her it was cool, and she left.
I had planned on cleaning up the house a little, washing the sheets, and showering before the other girl came over. Realized that I took so long trying to get off, that I had maybe fifteen minutes before the other girl would be getting here. Threw the sheets in the wash, didn’t worry about cleaning…but I realized I was still going to smell like sex. If I let her go down on me, I was still going to taste like sex too lol.

So I quick grabbed a washcloth and just tried to clean my junk as best as I could before she got there. Eventually when we started hooking up she was all ready to go down on me but I quick slipped it in before she could. She thought I was just really eager to fuck her…

I finally came with her and it was awesome.

Neither of them know about that.

15. I_Throwaway_Sluts

My teacher was always really flirty with me, and would ask me to do things that he thought I wouldn’t notice as “I like your tits so do this” such as making me shake spray paint for longer than usual, melting the nails into place while he held them from the other side (boobs RIGHT in his face) I would make a point to wear extra cleavage on the days I had had his class. Every time I work on an engine now I get horny, thinking of him.

He’s unmarried, so I had zero guilt. I’d wear short plaid skirts, and bend over his desk to grab something. One of the days he made me hold some huge piece of metal, which consisted of me wrapping my arms around it, while he was getting dents out. My hands happened to be wedged up against his crotch, and I looked up at him and gave him my best sex face, and teased him until he completely fucked up the metal because he wasn’t paying attention. Doing naughty things in public gets me off, and this was in the middle of class. Seeing him from time to time sends shivers down my spine, and I have an ultimate teacher fetish because of him.

High school was the best four years of my life because of him.

16. doot_doot

Was walking through my apartment building parking lot on the way to a friends house with my roommate when out of nowhere our upstairs girl neighbor (not very attractive) appears and says “let’s get naked you idiots.” she’s drunk, so are we. 5 seconds of silence and then like clockwork my friend begins making out with her while I gingerly place a hand inside her shirt and pop her right boob out. Looked at it, was unimpressed, my friend pulls back from his kiss and looks at the exposed boob, then looks at me and says “what do you think?” I shrugged and said “I’m about halfway hard, let’s just go.” he looks back at her and says, “we discussed it and decided we are going to go now.” we then walked away as she stared at us with one boob hanging out. Never spoke with her again. What was this thread about again?

Edit: since half of the replies I woke up to this morning seem to be asking what her boob looked like, here goes. You know when you throw a kids birthday party and a day or two later the balloons have been in the sun for a while and most of the helium has escaped? It’s this sad, quarter inflated shadow of its former self. It was kind of like that. It was hanging half out, kind of flat near the point where it came out of the shirt then floppy and oddly shaped. It was like her boob was created to hold 100 boobal units but ended up only being filled with 65. Also, the nipple was pointing directly straight down. She was maybe 20 years old, we were 23 I believe. Hopefully this helps explain my reaction to the boob.

17. mbacon101

Gave my boyfriend head in the backseat of the school bus in highschool. I remember the road being especially bumpy. We are still together 5 years later.

18. Malcriao

Threesome with two guys I had just met. On the beach.

Esta Cuba, haha.

19. think_less

Fuck throwaways, whatever…blew a guy while his roommate was in the room. I was still wearing a toga from the party…and I was actually very close to being sober…

Edit: To add to the awkward aftermath–when I was walking back to my room, I noticed I lost one of my earrings in the…events…so I had to keep bothering him and texting him to return it. So to all of you that are claiming it might be you–unless that happened, it wasn’t you, lol.

20. underthere

In college my roommate and I once fucked a pair of girls at the same time. I was in a lofted bed across from his bed: we reached across the gap to pound it but it was too far, so we ended up touching fingers like God and Adam at the Sistine Chapel.

21. sasha_fierce79

Brought 2 chicks home from the strip club.

Had an amazing time.

I am a female.

22. sparty_party

Lost my virginity in my mom’s bed..

23. Lambshank31

I sucked a guys dick on the sidewalk. Good news is it was in the ghetto and nobody even batted an eye.

Edit: I forgot : I also went to this fuck buddy’s house and I knew two out of the three guys there. I ended up giving blowjobs to both the guys I knew in the living room while the other dude just watched.

24. I_may_be_crazy

In my days as a drug dealer a lot of freaky shit happened. During a time I was selling a lot of extacy and coke, I was living with two strippers. They were hot as hell, and my best custies. One night after work they brought a half dozen of their coworkers home. Apparently they were bragging about my cunilinguistic skills at work, and one of their lesbian coworkers wanted to take the Pepsi challenge. She didn’t believe a guy could be as good at licking pussy as a woman. A room full of strippers watched as I got her off. The scene descended into a full scale drug-fueled orgy pretty quick. By the time it was all over I’d stuck my dick in 8 women.

25. silverbolt89

I was a freshman in college on my first marching band trip to our rival school. Now the football team and fans were always at each other’s throats, but the bands were tight. Each year, the other school’s band would visit for the football game and they would throw a party for the visiting band.

There’s at least 300 people crammed in that band house after the game. I start drinking and chilling with friends, meeting new people and shit. I notice a group of girls crowded in the corner and they would sometimes glance over in my direction and turn back to the circle giggling. I was a SAP at that point and I only had a few flings in college so far, so I had no fucking clue how to handle this situation. Luckily, one of the seniors from my band saw what was going on and gave me the rundown:
The senior lady section leader of the other band pick a rookie member of my band as their target. The goal? The first person in his pants, wins. Wins what you say? Alpha-female status? I don’t fucking know. Bottom line, I was the target, and everyone in my band knew it.

First girl comes on to me downstairs and we start making out. (Trombone section leader) After a while, she starts to lead me upstairs, but I am intercepted by the Piccolo section leader who brings me to the dance floor. She starts making out with me and puts my hand down her pants and starts feeling up my junk. Trombone section leader comes back and I was expecting a cat fight. Wrong. She joins in. The night wears on as I start to “meet” new girls and each attempt is getting more aggressive. At around 3:00 in the morning, I get dragged into the coat room by the piccolo section leader. She pushed me down on a pile of coats and had her way with me.

When I came out of that room, everyone who was still awake cheered for me. On the bus ride home, I felt like a fucking champion. The next four years in band, my reputation was solidified as “man-whore”.
TL;DR Band girls are slutty

26. stout-heart

In high school I went to my Gf’s house. She was there with four of her friends. One being her gay friend. The girls all agreed that if I let him fuck me in the ass, I could fuck all the girls. Let me just say I got to nail all the girls that night. P.S. That asshole went for 45 minutes on my ass.

27. koobear

One time I asked out a girl to lunch before I asked her out to coffee. Thought Catalog Logo Mark

image – Homo_Erectus