39 People On ‘What Is The Craziest Sex Act You’ve Participated In’

Sep. 10, 2013
xsssy2Thought Catalog producer, wrote a Kindle Single about philosophy (except for funner). Talk to me on Twitter and Tumblr.

1.

[deleted]:

First time I dropped acid I experienced pretty severe synesthesia. Music itself was making me feel like I was orgasming. My wife decided to take advantage of this, laid me down and gave me the most passionate BJ and sex in existence.

What was crazy about this was that as we were having sex I felt that her vagina was a space vortex and her cervix turned into meteors continually hitting my dick. On top of that real squirt was flying everywhere as she was cumming like crazy, but to me it would just hang in mid air and glisten and eventually formed into a giant shining ball of pleasure on the ceiling (yes, it was squirting that far…we have 12′ ceilings). I was also narrating everything that was going on and trying to describe what I was feeling the entire time.

We did this twice that night…one of the best nights of my life, though the clean up was intense.

Tl;dr: Fucked a space vortex while being accosted by meteors.

2.

dorbin2010:

I was VERY stoned one night at my ex girlfriends house and was crashing on her parents couch when her identical twin came in with her boyfriend and she started giving him head about four feet away from me. The room was pitch black so I didn’t think she saw me laying there at all.

I was so out of it that I spent the entire time wondering whether or not she was my own girlfriend cheating on me. When my eyes adjusted, I saw her staring right at me and she winked, smiled, and kept going.

3.

TwasIWhoShotJR:

Spanish dark rooms. You show up, shower, and then walk into a completely pitch black room filled with people.

Everything goes.

yeah.

4.

wickedsun:

My girlfriend was giving me a blowjob and when I finished she sneezed or something… Came right back out of her nose.

She said it smelled like sperm all day.

5.

StayClassynet:

Back in high school my at the time girlfriend wanted to try out handcuffs. So I cuff her to the bed frame and get on with the task at hand. I had pretty good rhythm in my ummm, thrusting. I guess she was pretty into it. With each thrust came a “waeh”-type moan. For no particular reason, I picked up my pace and was giving it to her pretty hard. Her moans picked up in pace too. Now the moans sounded like “waeh-ooo”. Basically, it sounded like I was having sex with a fire truck.
So what the hell is a guy to do? I kept thinking about fire trucks. The more I thought about it, the funnier it became. I was trying not to laugh at her, but it was too funny. I was burying my face in her shoulder trying to hide the laughter (we were missionary position)… but the laughter was too much.

And that was that. She thought I was laughing AT her… pretty much killed the sex that day. She started crying and was really sad. I felt pretty bad about everything. It was at this point I recognized that she probably didn’t want to be handcuffed to the bed any longer.

Whatever though, I still think it’s funny.

6.

[deleted]:

My parents are extremist crazy fundamentalists (and I don’t use this term tritely). My girlfriend (now wife) and I weren’t allowed to sleep together much less have sex so we would sneak the sex whenever we had a few minutes alone.

Well, one day she was on top, in a skirt, and it looked like we were just rough housing, which was tentatively allowed. My mother, brother and sister walk in and starting talking to us…we continued. Somehow managed to hide the orgasm as we “play fought with her pinning me down.”

7.

redditluv:

Lady wanted me to masturbate her with the head of a Barbie doll she brought. She opened a little carry drawer made for Barbies. She had about 6 of em in there. She picked one.

She asked me to 69 with her while I masturbated her with the Barbie head.

8.

wanttosnugglewithjew:

It involved halloween, a dumpster behind wendy’s and a bun.

9.

LouisNZ:

me and a mate spit-roasted a chick. awesome.

10.

[deleted]:

Golden showers (didn’t really dig it), ass to mouth (twice, both times I checked his dick for shit before swallowing it), and two threesomes (FFM).

I’d love to try DP in a MMF threesome. And I wouldn’t mind trying out one of those fucking machines…cuz I wanna fuck a rowbutt.

11.

[deleted]:

one time i had sex with my left hand, she was a virgin so we took it reeeeal slow, about half way through her slutty right hand sister (they look similar but are really opposites) wanted to join in, and since my girl lefty was already tired i let her sis take her place, that was a wild 4 minutes.

12.

the_guapo:

I had a threesome with my 8month pregnant ex girl friend(not mine) and another girl we had just met.

13.

dicksquad:

Im a male, I let an ex gf fuck me with a strapon multiple times

14.

rocketpants85:

I dated this girl for a while. She was really a nasty freak. She just loved to get down with sex all the time. It was like, anytime of day, she was like, “Yeah, let’s go! I’m so nasty!” And I’d be nailing her and she’d be like, “Oh, you’re nailing me! Cool!”

15.

texasjoe:

))((

16.

firebadmattgood:

Plain old butt sex with a long-term girlfriend. Some of you are making me sheepish about not flying my freak flag high enough.

17.

jactation:

not so much a crazy on my part but once my girlfriend was giving me the most fantastic blowjob ever and just as im about to climax….. vomited on my dick (and lap)

18.

FancyLaserEyes:

Was with my wife and our two friends, who are also married. We had a small party and took ecstasy. Those of that have taken this know that things can often get frisky. We had all done it before, and there was definitely some inter-couple making out.

This time, things got a little fancy. My wife and I slowly but surely started making out, and clothing started coming off. I recall my friend sitting there watching us, while her husband was smoking a cigarette. Eventually, he came back in the room and started working on her. Within ten minutes, they were on the bed next to us, and there was all kinds of romping going on.

It didn’t get too crazy–I made out with my friend’s wife, he made out with mine, and the girls made out with each other. But there was definitely a lot of fooling around and sex–it was just kept in the respective marriages.

19.

rgnysp0333:

Got a blowjob…in a box….in the common room of my freshman year dorm.

Basically there was an end of year charity drive (with no donations at this point) in the common room, which was empty, so we were messing around in the giant cardboard box.

20.

Entraya:

At an awesome party for my best friends brother and at about 2:00am I retire to my friends bedroom with her and her boyfriend. We are just chilling and chatting and then her BF pulls out some Oxycontin, we snort it and start drinking. I had already had a cone so I was mellow as fuck and my friends gets down to her underwear to be more comfy. I get down to a T-shirt and panties and we just lay on the bed high as fuck. The her BF starts to go down on her, at first she’s tells him to stop and thats its awkward coz I’m there, then she just goes with it. Now my friend is as hot as fuck and I’m Bi so I love checking her out and she knows that if she ever wanted to I would be there in a flash and her BF knows this also. After she comes which was like sweet sweet music to my ears , she takes off her top and her BF takes my hand and puts it on her tits. When she doesn’t object I get my grope on. Soon after that he literally picks her up and hands her to me, pussy first (she only weighs about 45kgs, naturally always been thin) He then goes behind me and pushes my head onto her pussy and I eat her out. He then starts spanking my ass and leaning over and grabbing her tits. She comes again and he starts to finger her, and she tells me I should get to my self and we come together. I don’t really remember much after doing a line off her tits and then woke up at 5:00pm that day with her BF gone home and we didn’t speak about it ever again. The weirdest thing is she is so closed off about anything sexual normally and even though she is my best friend in the whole world (finish each others sentences etc) I never knew much about her private life that way, I went from nothing to face in pussy.

21.

zmmar007:

May not be “crazy” but it was certainly the most disgusting for me. I was with this girl I was dating at the time and unfortunately on this one particular night she happened to be on her period. Now we figured, “that’s ok no biggy”. There was no reason why I still wouldn’t be able to enjoy myself, courtesy of a little bit of fellatio right? But my girlfriend decides that a plain old blowjob wasn’t enough and she wants to have some more fun with it. She proposed the idea of tying my hands to the bed posts so that she could “tease me” and draw out the pleasure, bringing me to the absolute brink and then holding back. Now naturally, I was all for it, so after whipping up a few knots we were good to go. Now at first things were going great. The blowjob was lasting ages as I was unable to take control and make me reach my desired ending, which of course made the experience more enjoyable. But at some point my girlfriend decides that it’s unfair for me to get all the attention. So with me tied up and helpless, she hops up and starts moving towards my face. I sense what’s coming and begin shaking my head, just saying repeatedly “No…no, no, no”. She soon shut me up as she sat down on my face, smearing her bloody vagina across my lips and trying to force me to go down on her. It was disgusting and I had to sit there, unable to break free, as I clenched my teeth and tightened my lips together with blood trickling down the side of my mouth. It was the worst sexual experience I have had.

22.

[deleted]:

Incest, repeated, fully consensual.

What do I win?

23.

undieminer:

Had a girl who wanted me to put it in her ear. Every time I put it near her mouth she’d turn away.

24.

FearTheGinger:

M-M-F threesome (I am the F) while on shrooms. Just the one time.

25.

Schmibitar:

I had sex in a tree once. It was… weird.

26.

biggbuckz:

Everything pretty normal… but in an elevator

27.

philter451:

I used to work for a WISP so I had access to a lot of roof-tops which made for some sweet views. I met this really hot girl at a club downtown and thought I might get lucky if I invited her up for an epic view of the city.
Long story short I had sex on the edge of a sky-scraper. Most adrenaline fueled sex of my life. I was sitting on the edge with my back to oblivion while she went down on me. At one point she paused and said look down and for some fucking stupid reason I did. Then she got on top and rode me. So fucked up but I still feel like a badass for doing it.

28.

bunsofcheese:

The Blue Jays won their second world series (in a row) and I ended up in a parking lot with five other guys and we all had sex. It was kinda fun.

29.

gweezer:

Not an ‘insane fetish’ or anything, but pretty logically insane: I had a threesome with my husband and his ex who he had previously left me for and who I held a hatred/jealousy complex for. It’s hard to explain why I decided to do it, so I wont bore you guys with the details-but it was ultimately my decision.

30.

[deleted]:

My friend and I were under a blanket in her bedroom. She stimulated me with a riding crop while sucking my nipples. Meanwhile, her boyfriend was oblivious painting the next room and kept making small talk with us.

31.

[deleted]:

I generally think that people are too uptight about sex, and that too few people with reasonably open sex attitudes are willing to speak out.

My most extraordinary must have been a tested bareback party with 5-6 guys and 2 women that I put together a couple years ago. These were hand picked, good looking people who flew in for the occasion, and everyone was recently tested. The girls had a lot of fun, and we, of course, had fun with them. About 2 guys per girl seems optimal to keep the girls busy. There being more than one girl allows for intermittent girl on girl action, which is hot, and relieves each girl of the pressure where she would feel like she has to satisfy all the guys.

Awesome experience, would recommend. It was frustrating to organize – you have to find attractive, responsible, moneyed people who understand testing as a viable method of STD risk management, who are interested in group sex, willing to travel for it, and are available at the same time. It was worth it for the experience, though.

32.

sns_abdl:

Wet a diaper while I was going down on my girlfriend.

33.

[deleted]:

I dommed (BDSM) a guy once… strange experience. He was really into me stepping on him in bare feet, his face specifically. He bought a pair of my old shoes that I was gonna throw out for $20.

34.

MatthewX5000:

Rape fantasy.

35.

joyfield:

Me and an ex went to a swingers club and ending up having sex with a loot of peoples watching. Not really my cup of tea but now i have at least done it and can “brag” about if to at least a few friends haha. Nowadays i am forever alone and the craziest sex i have is with my hand.

36.

3DPK:

Front seat of a Civic in the mall parking lot during the middle of the day. People walking by and what not. There was an AX commercial shortly after that had a girl with a steering wheel imprint on her back, we laughed for days.

37.

FrankManic:

Once I had someone tied up, more or less at my mercy, and pretty much entirely clothed. I picked them up and threw them in the shower. It was hilarious and awesome and quite kink.

38.

historyboy:

had a dinner party at my place. two guys three girls. got blasted off of whiskey and 4loko, then decided to play a strip game. everyone ended up naked. we then proceeded to do body shots off of each other. then we got sticky and decided to shower together, before moving to my roommates’ room where we became a mass of humanity, sucking, licking, fingering, fondling and fucking.

39.

FishboneMinus:

Consensual sex in the missionary position. Shit was absurd. TC mark

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