Thought Catalog

50 People On ‘The Sluttiest Thing I’ve Ever Done’

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Compiled from AskReddit.
Cameron Russell
Cameron Russell

1.

idontlikehamsters:

Showed my boobs for a panini

2.

MajesticStag:

Got head seeing cloudy with a chance of meatballs. 15 minutes into what was an empty theater a small family came in and totally knew what was up. We left shortly thereafter in the most awkward rush.. But it was hot.

3.

girlintheYODAshirt:

Had sex on the hood of a Ferrari on the Las Vegas strip – it wasn’t my car, or my gentleman friends, it was just some random car. Also A LOT of people stopped to watch. I didn’t care, I was drunk, young, and on the hood of a Ferrari.

4.

Nameyschmamey:

One time I had a date with a guy named Jon. After the date he came back to my place, we watched a movie, had some wine, and then we fucked 3 times. About an hour after he left though, I was already horny again and this other guy I was talking to at the time (named John) texted me asking me what I was up to…

I ended up having sex with both John and Jon in the same night. Definitely my sluttiest moment. (I did use condoms though!)

5.

White_smoke:

Met a girl in a Dunkin donuts parking lot at 10:00am. She invited me over to her house. We get there and after thirty minutes she asks if I want to have sex. Of course I say yes. No kissing or touching. She simply bends over and hands me a condom out of the biggest box of condoms I’ve ever seen. This should have been my cue to leave but at that point I was in too deep. I start from behind and two minutes in I misjudge a pump and end up cumming. So embarrassing. As I lay there in shame she starts at herself with a vibrator and turns to me and says “have you ever choked someone?” She takes my hand and puts it to her throat. So I choke her until she cums. I shuffle out after we exchange numbers and can only shake my head in disgust when I get in my car.

6.

anotherthrowaway3412:

My best friend and I visited his sister in college when we were seniors and she was a freshman, we went out to the bars with her and her friends (they all had fake ids). His sister was totally all over me all night. I continuously pushed her away (which made it worse) and explained to her that even though I thought she was really hot I would not do anything out of respect for her brother. Her brother gets tanked and I got really drunk as well and I briefly made out with her at one bars without her brother seeing. Later in the night I crossed the point where my drunkness outweighed my friendship and I let her blow me in the backseat of a cab while her brother was in the front seat. (Still had no idea). Her and her roommate snuck us into their dorms were my drunk best friend and the roommate immediately passed out. I then proceeded to fuck her not 4 feet away from her brother. He still does not know. I am a terrible, terrible friend.

7.

way_fairer:

Spring Break 2009: Fucked a random girl I just met in a Porta-Potty.

8.

__bieberhole69:

I fucked this chick my best friend hooked me up with, she left I went to bed with no shower. In the morning my ex girlfriend shows up to my place, things start getting heated she proceeds to suck my dick tasting all of the other girl from the night before. Yeah pretty sleazy.

9.

Seventh7Sun:

I made out with a girl at the theater during Schindler’s List.

10.

dick_herpes:

I had an affair with one of my oldest childhood friend’s lesbian partner and got her pregnant.

11.

whiskeynwaitresses:

I used to hang out with a lesbian couple pretty often. One night one of them is out of town and the other wants to hangout so we go to the bar and get hammered. We decide to go back to her place to crash cuz it was close to the bar and they had a guest room (my crashing at their place was pretty common occurrence). So we are chilling on the couch waiting for some pizza we ordered when we get on the subject of showers and growers. I say something along the lines of “you wouldnt believe the difference” she asks to see. I say “I dunno…” and she convinces me since she’s a lesbian it doesn’t matter and is akin to a dude seeing my dick in a locker room, which doesnt really make sense but I was wasted. Anyway, I pull it out and proceed to get hard. All of a sudden she is on top of me and we are making out and shes giving me a handy. We end up going upstairs and fucking, midway through doorbell rings and I say “The fuck is that?” and remember the pizza, hop off her naked run downstairs pay the pizza guy naked, like literally threw $40 at him and grabbed the pizza which i dropped in the foyer and went back upstairs and went back at it.

12.

Spatzman:

My girlfriend confesses to me that she has been having an affair. The thing is she has been messing with my best friend’s girlfriend. I pretend to be all upset while the whole time I am grilling her for details. I finally say that I want to ask my buddy’s girl why she would do that to me and my buddy. All the while I am scheming to get them alone so I can get something going with them both. My girlfriend says she is not doing that. I grab her phone and then call this other chick. The other chick answers the phone thinking my girlfriend is calling and has this really hot sexy voice. When I say it is me she goes all business class in her tone. I tell her that my girl has admitted they are screwing around on me and my buddy. I say that we have to talk this out right away and she should come over. I realize that I am pushing it but she agrees to come over. She arrives about ten minutes later. While we wait I hardly talk to my girlfriend. When the other girl arrives I just sit there for five minutes and don’t say a word. I finally admit that this whole thing has been a ploy to get her over so I can watch her and my girl go at it. Another lie. They both turn on me and call me every name they can think of. I then pull the sleaziest move of my life. I tell them that I can just tell my friend that I came home and found them messing around and that’s why I am calling him at 12:30am on a weeknight. I see them both thinking how they are going to get out of this. My girlfriend says fuck it and starts kissing the other girl. I sit there for about 5 minutes and try to work my way in. My girlfriend says no but the other chick gives me the go ahead. I then jump in and fulfill a lifetime of fantasies in about ten minutes. The three of us hooked like this whenever we got drunk for like the next 3 months. My girlfriend hated my buddy so we would always have to sneak around on him. I could hardly look him in the eye when I was sober. I still hang out with my buddy but have since been dumped by both girls. I never have told anyone because all my friends know each other and would ostracize me for being such a pig.

13.

headonthebar2516:

Stripped on a pool table while three guys watched and stuffed money in my underwear. I’m not a stripper I just did it for fun.

14.

ChiGuy_1988:

Well, my time to shine! I lost my virginity to my best friends mom… My friend has no idea that it happened.

15.

Viciouslicker:

Junior year of high school. Fucked my boyfriend on the bus on the way to school one morning.

16.

trippie_hippie:

Took a guy home from the bar, start fucking in front of his room mate, room mate joins, they basically fuck the life out of me. Hadn’t been fucked like that in over a year. One night stand success.

17.

Richard_Borrowitz:

I lost my virginity on top of a horse (yes, a live, full-sized horse) in its stable at the age of 17 while away at boarding school.

There were only about 40 students, and it was a VERY controlled environment. But I somehow convinced one of the counselors who ran the horse stables to help me and the girl I was planning on having sex with sneak out of our dorms after “lights-out” so we could fuck somewhere in the stables where no one could really see us.

We ended up sitting on a horse facing one another. She was giving me a handy and I was fingering her, plus lots of kissing, etc…

Eventually we decided to fuck, but she couldn’t exactly take her sweat pants off because we were atop a horse, so I simply grabbed the crotch area of her sweat pants and ripped the seam apart.

She hopped onto my lap and we fucked. ON TOP OF A HORSE!!!

It was the best 2 minutes of my life.

18.

DrakeSensation:

I fucked two roommates and they both wanted to keep it a secret from each other. It lasted until they both moved away. A few times, one had left my bed only hours earlier and the other entered. The fun part was how they each lied to the other about where they were going when they would come over to bang.

19.

PornDirectingPilot:

I fooled around with a girl I met at a party. When she passed out I proceeded to fuck her boyfriend with her lying right next to us.

20.

asqueakywheel:

I was CouchSurfing in New Zealand and had hooked up with my first host in Auckland. After traveling around the country for a few weeks I’d arranged to stay with him again before flying out of AKL. Unfortunately he confused the dates of a trip he was taking and was going to be in Wellington the day I arrived but had arranged for another one of his friends to pick me up and host me. Coincidentally the flight I was taking had a 7 hour layover in Wellington, so after masturbating in the bathroom at least 5 times during the first few hours he picked me up from the airport and we fucked a couple times in his car off the side of the highway.

He dropped me off at the airport just in time for my second flight and I arrived in Auckland where his two friends picked me up. Proceeded to pregame with two cheap bottles of wine as they drove downtown then went partying all night. Went home and fucked his friend less than 5 hours after him.

The next morning the friend made me breakfast and I went to the beach with the other roommates. We came back and were daydrinking when my last host in Auckland drove out to the Air Force base I was staying at and picked me up to go spend my last night at his swanky place in Ponsonby. Despite the fact that he was 16 years older than me the sexual chemistry was out of control. We went out that night and made it through maybe 2 drinks before we were making out and he was pulling me out of the bar. We were so horny we took a cab back to his place (the walk there wasn’t even half a mile!) and fucked until 5 in the morning. Then he drove me to the airport the next day and used his fancy frequent flyer card to get me in the accelerated line past customs :D

21.

auoiaf:

1st time at a strip club, I didn’t really want to go. After all my friends kinda found a girl and left a cute little stripper came up to me and asked why I was alone, she took me to the back for a dance. I was pretty drunk when she told me I was allowed to touch her and was instantly hard. She noticed and I told her she was allowed to touch it. I ate her out and fucked her without a condom. Got chlamydia.

22.

filteredfun:

Went in to get a haircut at a shitty mall salon and the girl cutting my hair got very flirty with me. She was making comments about how I was a nice break from the women and old men who come to her and even one about how she couldn’t stop checking my out in the mirror.

Haircut is done (she did an awesome job), I’m leaving and she writes her number down on a business card and gives it to me. Pretty normal procedure if you’re trying to get repeat clients. I grab the card, kind of nervous and don’t know what to say so I walk out.

My buddy was walking around the mall waiting for me so I meet up with him and we leave. Driving down the street I realize I forgot to pay her so I text her and say, “hey, I forgot to pay you! Totally embarrassed, I’ll be right back.” I get back and she is totally cool saying she’s glad she has my number now.

We keep texting that night and the next day. That day at work the texts got so fucking heated. Literally fucking each other via text message… She’s telling me she wants me to eat her ass… We exchange naked photos.

We ended up meeting late one night for a beer, neither of us had much time but she ended up blowing me in her car and THEN tells me she has a boyfriend.

I leave and we continue to text for a bit and she keeps telling me I need to come back for a “spray tan”. Their spray tan is done by the stylists with a tanning gun (?) and you get naked for it. So, I go back in after two weeks for another haircut (didn’t need one), it’s near closing time and I’m her last client. She is the only person there other than the receptionist.

During this haircut she starts talking dirty, telling my all she could think about when she first saw me was what my cock looked like etc. she even reached down to grab my dick under the cape. Haircut is finished (not as good as the last one) and she tells me to go check out what’s in this room in the back. I walk down and see it’s the spray tan room, take a hint and walk inside to wait for her.

She walks in a minute later. She’s super hot, floor length black skirt and a black tank top. She’s smiling and I lean in to kiss her. She goes into freak mode and drops to her knees to suck my dick. We end up rolling around on the floor that has a dirty towel on it fucking plenty of different positions. I never did eat her ass even though I love doing that.

I got $10 of my haircut and tipped her $20… It was worth it. I texted her after that and got no response (it’s cool, she has a boyfriend). I texted her a while later asking for another haircut and again, no response. It’s ok I hate going to the mall.

23.

krebstarpatron:

Banged a terrible person. She was a really judgmental Sex and the City wannabe type, who was also physically unattractive. But she had a nice body and I was wasted. She stopped to get falafel and I was so close to jumping in a cab and getting out of there, but something stopped me. My penis. Which I later tried to slip into her asshole as she drunkenly mumbled “Jesus Christ.”

24.

hookershow:

I recently met someone that pays hookers for me to fuck… he watches closely and touches a little bit here and there. Its like I found a cheat code for the universe…

25.

indieshometownhifi:

Got a blowie by my ex wife in a live peep show booth.

26.

iamaredditer:

I was banging a milf for about 6 months(34 I was 21) up until the day of her marriage. She would whisper in my ear it’s just sex don’t fall in love.

27.

MaximusStinson:

I let some girl shit on my dick and then I had her suck it off. Cringe I quit alcohol the day after.

28.

WeOwntheNightX:

I watched porn for 2 hours once… :(

29.

tonguejack-a-shitbox:

When I was 17 I had sex with my football coach’s wife. She was an older seductive curvy woman. His nickname was “moose” and he earned it. She ended up getting pregnant and he had a vasectomy prior to that. My mom ended up at her house banging on the door one night when I was there yelling and screaming that she was a whore and she knew I was in there. He ended up finding out. The story around town was that he had the kid tested and it was his but I grew up in a really small town where people cared about these things and talked about them a lot. I think they just said the test came out that way for looks. I never spoke to either of them about it again even though I did see them many times. I ended up marrying my football coach’s cousin’s daughter (told you, small town). They were at all the family events. They ended up moving to a city an hour away to get away from the rumor mill and got divorced.

30.

jarinatorman:

Fingered a girl in my art class in the middle of class. I don’t think anyone caught on besides our table mates and they were friend of hers and awkward types so I guess they just… Dealt with it. I don’t know.

Read more Thought Catalog After Dark articles here.

31.

throwawaybisex:

I had sex with my same gender cousin while we were both staying at his parent’s house.

32.

ohfail:

Had sex in a convent. In public. Very inconsiderate story, actually.

College, 2nd year and I’m FWB with this amazing redhead. She’s 6′ tall, stacked, and fit – with curly bright orange hair down to her waist. No obligation as a boyfriend. I couldn’t get enough, and neither could she. Sex anywhere, everywhere. We fucked standing in the middle of live concerts more than once. That kind of thing.

We took our spring break once in Chicago, doing volunteer work in homeless shelters and soup kitchens. A whole bunch of us went from the same college program – probably 15 of us in one of those huge vans. We didn’t really know one another at first, but made friends and did sing alongs on the long ride to Chicago. Snuck in some BJs in the back of the van on the way. At least, I thought we were sneaky….

Once we get there, we get set up with our host organization which had arranged for us to stay in some convent in a rough part of south central Chicago. Their plan? All of us together in the same large room, sleeping in our sleeping bags close to one another.

My non-GF and I started out just sleeping close to each other…then feeling each other up, horsing around…and by day 3 I’m taking her doggy style, naked, on top of our sleeping bags. In the middle of the common area, while everyone else was there. Yeahhhhhhhhh – I have no idea WTF we were thinking. It was dark? Fuck. I don’t know. Stupid rude of us.

By the 5th day, we were still going at it shamelessly and the other kids there started to simply move out into other areas of the convent. By night 6, we were alone in this big room that had easily slept a dozen or more of us. Obliviously sucking and fucking like the dumb beasts we were.

The rest of the group played it off fairly smoothly and – for whatever reason – no chaperone, host or organizer ever called us on it. Don’t know why; we were being asshats of the highest order.

33.

SayHelloToMyAfro:

Had sex in the catacombs in Paris, with two separate guys, 30 minutes between the two. One I’d had about a ten min conversation with, the other I’d not spoken to at all. They’re mutual friends so I suspect that if they didn’t know then, they do by now.

34.

coldbeeronsunday:

I was a Catholic schoolgirl. In 8th grade, I blew one of my guy friends in the confessional at the Catholic church next door to our school. It was pitch black dark in that little wooden booth, so after a while we moved and fooled around some more in other areas of the church. Later he told me he felt really guilty about it, but I never did. Going to hell for that one.

More recently, I blew a guy and he came so hard that he couldn’t get it back up afterwards. As soon as he left, I called another guy over to have sex with me so I could get off. Turns out, he had driven by my house earlier that day and asked me who owned the silver Mustang in my driveway (belonged to the other guy). I said it belonged to a friend of mine from school who just came over to chat. Weeks later I owned up to it. He wasn’t very pleased.

35.

purplepoptarts:

Had sex with my friend in the back of his car and ended up with a bunch of hickies. I went to a party with my (recently made) ex boyfriend right after. I hid my neck most of the night so he wouldn’t see. When we left we went back to his house and had sex with the lights off and he ended up giving me hickies as well so when we turned on the lights he just thought that all the hickies were from him.

36.

firecoloredfeathers:

I whipped out my boyfriends dick at a party next to a bonfire and gave him a blowjob for everyones entertainment.

37.

piggy_loves_truffles:

Had gangbang with 3 guys streaming live on webcam. I’m a girl.

38.

sweaty_yeti:

Slept with a friend’s professor to get her an A (wtf?)

39.

handjobbanana:

Slept with my cousin at a family reunion in a skatepark bowl and on my aunts bed.

40.

Dave_Likes_Peaches:

This is a throwaway as some friends of mine use reddit and know my username.
Earlier this year my wife did something very adventurous and out of the ordinary. It was valentines day night we had just gone out for dinner and left the baby with a sitter who was one of my wifes friends.

We have dinner, come home and my wife informs me that we are going to have a threesome with the sitter, her friend. I thought to myself oh this is a joke she is kidding but when I walk in to our bedroom as instructed there is her friend in just her bra and panties.
Now I’ve never had a threesome before and I’d only even slept with three women including my wife so this was pretty shocking but arousing. So I did what any full blooded man would do, took my clothes off.

This friend is seriously hot I’d never even thought about her in a sexual way before because I always found her kinda neurotic but god did she know how to suck a dick. So we had sex for what seemed like 10 minutes but in reality it was more like an hour. We all fall asleep. When I wake up in the morning the sitter and my wife are gone, I go to the bathroom piss, go downstairs and my wife is there. All is good we discuss the threesome and we are still pretty excited about it, just discussing it gets us turned on and we have a quickie right there in the kitchen.

Over the next few weeks we discuss it quite a few times and each time it leads to fooling around or sex. Sadly my wife and that friend stopped being friends after the threesome, my wife says it is unrelated to what we did they just stopped keeping in contact.

41.

malibugt:

Met a guy at a bar who was blackout drunk, got to his apartment to find out he lived with his identical twin brother (who was similarly intoxicated).

Proceeded to have sex with them at the same time. Not my best moment/probably ruined a family.

42.

theassholequeen:

Went home with my bestfriend and these 2 guys after the bars, halfway through we decided to switch partners… Lost all my self respect and shame that night

43.

Blue_Apocalypse:

I was dating a very religious cheerleader in high school who just wouldn’t give it up. We had lots of fun but no sex. This went on for about a year and I started to get frustrated. All of my friends were loosing their virginity and all I’d had was a handy. So this smoking hot strawberry blonde girl moves to town and my gf at the time is mentoring her in cheering. When I was introduced there was an instant chemestry between us.

I ended up having a couple of classes with the new girl and our conversations got quite heated… to say the least.

One night while my parents were out and after all of my siblings were a sleep, I invited her over to “study”. She showed up wearing the hottest short skirt and low cut top i’d seen at that point in my life. Within a few minutes of her being there I asked her if she wanted to see something cool. She agreed and I took her to my basement where my brothers and sisters have a fully functional bouncy house/moon walk.

Ill never forget the epic view of her thong and perfect ass as she provocatively crawled into the moon walk. Im pretty sure I sprinted and dove in after her. We continued to have sex twice before my parents returned.

44.

Blan21:

I’ll have sex with just about any guy who asks politely and doesn’t smell. Does that make me a whore?

45.

boobercal:

When I was (just barely) 18, my grad class went on a trip white water rafting. We all boarded the bus, picking up groups of people in cities along the way. At one stop a set of twins (male) get on the bus and sit near me and my other girlfriends. They bust open a case of beer and two hours later we are naked on the greyhound charter bus playing some silly truth or dare type game. Fast forward a day, we’ve all been rafting and drinking all day. I have been all over “Steve” (I don’t actually remember his name) and we are about to find a quiet place … Until “Sean” (twin brother, might not be his name either) shows up and follows us to the tent … Well what’s a girl to do when faced with this situation? Invite them both inside the tent, of course. And so commences my first threesome, my first Eiffel tower, my first sex in a tent. I specifically remember them high-fiving each other.

46.

DV8D:

Had just been dumped by the guy I was seeing. Proceeded to go to a fetish club near my house where I then got absolutely shit faced and brought home 2 girls and a guy. Vaguely remember pouring more drinks, some fun naked times with the girls and then passed out while giving the guy head. Woke up about mid morning, apt wrecked and my sheets ruined with just about every conciveable bodily fluid.

47.

candygrind:

Just to preface: I’m a girl.

Slept with a guy for about 2 months for the heck of it. Run into him about a month later and he introduces me to the new girl he’s sleeping with, which is cool since I originally called off our arrangement.

Fast forward a couple hours into the night and the new girl apparently finds out I’m bisexual so she starts hanging all over me. However, I ended up taking the guy and a completely different gotten back to my place to have a 3some.

I then started hanging out with the original girl and we eventually hooked up and have since become best friends with the occasional sleepovers…

48.

jankeyjenkum:

fucked practically everyone on MySpace from about 2002-2007

49.

ssraegi:

Maybe not that slutty, but I fucked three guys in the span of a day. A brunch and a screw with a guy who I was just starting to date. Dinner+drinks followed by an absolute pounding thanks to a fella who I was seeing casually for months. Then I flew three hours to a few states over on a scheduled visit to an ex/old friend. Got to his place around 6AM and sucked and rode him till I damn well earned my steak breakfast. Went raw with 2 of them (pills+sans diseases for everyone). Pretty sweet day.

50.

benjetta96:

I’m ashamed that this is finally my time to shine.

In 8th grade I have a guy a blowjob outside in the bushes at a college we were visiting for an abstinence talk.

We had only known each other for about fifteen minutes beforehand. TC mark

Read more essays about this in our newest collection here.

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