1. Womp womp.

Didn’t actually have a threesome, but I got pretty close. I’ve been told its a funny story.

I had just finished my senior in high school at the time and I was enjoying my summer before going off to college. I had moved into the pool house attached to my parents house for the summer so I could basically come and go as I pleased. One night I was hanging out with my friend down the street at his house and a few other people that lived in the neighborhood. After a bit of drinking one of the girls asked if I wanted to just hang out with her and her best friend..alone. Me being drunk and oblivious to what they had in mind, invited them over to watch me play video games. ( I don’t know what I was thinking ) They agreed and we walked to my house and straight into the pool house. My parents were out at a dinner with friends. Usually that meant them being out fairly late. Anyways we got to my room and they both laid down on the bed. I went to the bathroom to pee and when I came out they were both topless and giggling. Game on! I dove right in and before I knew It I was half naked and we were doing some heavy petting. Just as things were heating up I heard the door to my parents house open and close. I could faintly hear footsteps outside. I leapt out of bed and ran to the door and was met by my mother. So at this time I’m fully excited if you know what I mean, and I’m awkwardly hiding halfway behind the cracked door. I tried playing it cool and I was like “oh hey ma, what’s up?” Of course my mom saw right through me and realized something was up. She pushed the door open and saw these two girls struggling to cover up and put their bras back on. She gasped and ran back to the house. I ran after her while trying to put on some shorts. I heard my mom scream to my dad (lets call him Robert) “ROBERT! HES GOT TWO GIRLS BACK THERE!” And then my dad surprised me by being pretty cool about it. He yelled back to my mom (lets call her Beth) “BETH! LEAVE HIM ALONE!” My mom went upstairs and when I went back to the pool house the girls were gone.

womp womp.

2. Preferring the intimacy of one.

I’ve had a threesome with two guys. They were friends, we were hanging out drinking, ended up really wasted. One of them was trying to get with me, I was kissing him but not really interested in taking it further. We went to bed, still kissing but I was planning to go to sleep, we’ve shared a bed before and nothing’s happened. Then the other guy came and got into bed and kissed me, and they were both touching me. So I kind of thought fuck it, it’d be an interesting experience.

The next day I was super hungover and went home, I didn’t feel awkward just ill from all the alcohol. Nothing’s happened between any of us since and we don’t really talk about it. But it definitely showed me that I prefer one on one sex, mostly for the intimacy.

3. Sounds pretty hot.

From a guy’s point of view the memory and idea of it were way better than the actual thing. We were in a car, one girl straddling me while making out with the one next to her. We took turns using our hands to make sure the off girl was well taken care of. When one finished they switched spots. Rinse and repeat.

I still fap to it to this day.

4. Just not the same…

I just couldn’t bring myself to do anything more than kissing and touching because it really didn’t turn me on at all. She did some stuff to me and it was alright but not the same as what I feel with a guy. It’s strange because I’ve always enjoyed lesbian porn but the real deal just wasn’t for me.

5. “Spit roasting.”

Me and a stranger spit roasted his girlfriend.

Allow me to continue…

I was in AIT for the Army and we had “phases”, where you had certain privileges, like leaving base, etc. I was at the final phase, so I could stay off post on weekends. Basically all the phase 5 people would tear up the clubs and strip joints and get a hotel for the night. This was one of those nights.

Long story short, I ended up separating from everyone else and going to this cheesy pop club, I can’t exactly remember. I was drunk. Ended up on the dance floor as like the only motherfucker on the dance floor. Apparently my moves weren’t bad, because this Puerto Rican-looking girl comes out of nowhere and we’re getting slutty with it. Then comes this short white guy telling me something. I’m thinking maybe he’s the boyfriend. He was, but he was asking if I wanted to go back to their hotel. OK why the hell not?

Cab ride. Girl is all on my junk, and his. We get to the hotel room and the spit roast begins. It was hilarious how immediately the spit roast just went down. Eventually I tell her I’m about to pop, to which she says, “That’s the point”, so I go in her mouth. She swallows. Her boyfriend finishes on her back then she goes take a shower and I get my pants all the way back on and kinda just look around awkwardly while the boyfriend is sitting in the bed, and I just say, “so.. uh… see ya later”, and I walk out and call a cab.

Never saw either of those two people again.

6. TL;DR

I’ve been in two actual threesomes and two fizzled attempts at them.

My first-ever threesome was when I was sixteen, and it took place in a hot tub at a friend’s New Year’s Eve party. That sentence alone should be enough to tell you that it didn’t go well. For as arousing or sensual as hanging out in a hot tub might be, it’s not really the best place to do your naughty dance. Still, hormones were bubbling, and the two girls I was with – one of whom was my girlfriend at the time – were both eager, so we gave it a shot.

Unfortunately, the entire thing only lasted about five minutes before a combination of awkwardness and physical discomfort brought it to a premature end. We’d tried “group kissing” – which my girlfriend had insisted was a thoroughly pleasurable endeavor – and a lot of mutual touching, but nothing was especially stimulating for anyone. My girlfriend got frustrated, our mutual friend got bored, and we all decided that maybe playing Ping Pong in the garage was more fun after all.

The next time that I had a threesome – if you could even call it having one, which I wouldn’t – went even less well. I’d made plans with an acquaintance to visit her apartment, get drunk with her and a random girl that she’d allegedly found on Craigslist, and then see where the evening took us. There was only one catch: Since the young woman hosting the event had already started drinking, I’d have to be the one to pick up our third partner. To make a long story short, it turned out that the two of them had already known each other, and that I’d been used as a free taxi service. I wound up leaving (at their request) within ten minutes of arrival.

Now, with both of those failed attempts under my belt, you’d think that I’d have an aversion to threesomes… or maybe you wouldn’t, I don’t know. The point is that I tried again (with different women) several years later, and it actually turned out to be a really good experience for all of us.

We started off by playing “Strip Scrabble,” the rules for which we kind of invented on the fly. Basically, any time someone scored fifty points or higher, the other two people would have to remove a piece of clothing. That requisite point value declined as the game went on, and by the time we’d used all of the tiles, we’d resorted to offering silly dares (since we’d run out of clothes to remove). At one point, I was tasked with imitating a Star Trek character while doing the “helicopter dick” across my bedroom. Not long after that, we all adjourned to my bed and jumped into more direct sexuality. We had some laughs in trying to figure out the mechanics (and at one point – completely by accident, I swear – I went in through the wrong entrance), but on the whole, it was a lighthearted and enjoyable evening.

I had a second threesome with the same two girls a few months after that, and it was even better.
I know you were probably expecting a story of things going catastrophically wrong, but honestly, it was as simple and casual as having a group conversation. My opinion on the matter is that everyone needs to be sane, honest, and uncomplicated. As long as you’re all just there to have fun, even the most awkward moment can be a building block for an entertaining memory.

Just be sure you get your angle of entry right.

TL;DR: Fizzle, fizzle, fuck, fuck, twice misfortune, twice in luck.

7. Experimenting with the husband.

Last summer, my husband and I tried to make a triangle work with one of my friends. We had loads of difficulties, and it has since ended, but the one thing that worked fine was the sex.

We had several threesomes, the first of which was away from home when we were staying in Belgium to go hiking. It was exactly what a first time should be like: fun, exciting, a little scary and very intense. My husband and I were both starting to fall in love with her, and it felt both safe and completely new.

The aftermath however wasn’t so great. The woman in question is very, very intelligent, funny, versatile etc, but also a little scary (think sociopathic tendencies) which come out when she feels vulnerable or unsure. She lashed out pretty badly.

Still, I wish that it’d worked out. She can be amazing, and I miss her.

And the sex was fantastic (both as threesomes and as pairings, for all of us).

8. A very “meh” experience.

Finally: story time.

One of my best friends in high school and college was dating this girl for a while, they were into the open relationships. He knew she wanted to fuck me and I was always down for some strange.

They went to college out of state, but came home to visit one time. He called me and explained that there was a family thing going on that wasn’t really for girlfriends, and asked if I would host her for a night. He said she was probably bringing a friend.

At this point, I knew what I was up for.

What I didn’t expect was him sending her with enough cash to buy all three of us dinner and enough liquor to have a party. The three of us and my roommate and his fiancé play drinking games and get steadily drunker and more raunchy. My roommate and his fiancé step out for a second and girl #1 leans over and says “you know we’re having a threesome tonight, right?” And then bit my ear, which is a huge turn on.

We eventually ended up in my room. Girl #1 got tied to the futon while I played with girl #2. We all played for a while, then went to the shower where the girls played with the removable shower head and I made use of whatever hole I was presented with.

It wasn’t great. I wasn’t comfortable, I felt like I was performing the whole time. I wasn’t THAT attracted to the girls and I felt like it was an opportunity I had to take because it was there. They fell asleep and I went up to the couch.

They left in the morning and left all the liquor, so that was nice.

2/10 probably wouldn’t do again.

9. Wanna play Madden?

Finally, my time to shine has come! Several summers ago I was out at a club with a buddy, let’s call him Kyle. we both frequent the place because the drinks are cheap and it’s relatively easy to pick up women. I knew a waitress there, and knew she had a thing for me. I was 21, she was 37. I’d never capitalized on her attraction to me, mostly because there were usually better looking girls who were just as willing to go home for the night. On this particular night however, I was tired and didn’t feel like laying groundwork with anyone, so as the night wore on I approached her and told her she should take me home once she was off work. Kyle had been striking out all night, so I threw in “kyle should come along too.” She eyed him up and down for about 2 seconds before nodding in approval, so it was on.

So the bar closes, and the waitress, we’ll call her Trina, gives us a ride back to her place, (in a minivan) while kyle and I drunkenly exchange glances that say “fuck it, may as well”. Trina has a small house and we follow her to her bedroom and proceed with the spit roast, Chinese finger trap, whatever you wanna call it. She looks decent naked. Now here’s where it gets weird for me.
Kyle has the bottom, (vagina), and I get the top (mouth), and he spanks her. Really hard. And says “suck it, Trina!” So he’s urging her to shlob my knob harder, which strikes me as weird because even though I’m fully aware of the other guy in the room, I’m only paying attention to what’s going on on my end. That’s the only way I was comfortable, I stay on my side, he stays on his and we only pay attention to Trina and like gentlemen, we ignore one another.

A little later we’ve switched ends and I’m giving Trina my A plus effort, hoping to wrap this up and call it a night. I’m approaching my vinegar strokes when again, Kyle interferes with my concentration by yelling “work your hips bitch!” At this point I’m done. I remove myself from the scenario and walk into her bathroom, furiously scrubbing my dong and using her hand towel to dry it, then walking Back through the bedroom to reach the living room, where I could wait out the awkwardness. Boy was I wrong.

I enter the living room to see that the tv is on, and remember it being off earlier. That years Madden game was paused on the screen, and I immediately realize I’ve made a mistake. Sitting right there on the couch eyeing me suspiciously, is her teenage son….. we lock eyes for what felt like an eternity, and I do the only thing I can think of. I say, “you playing madden?” Another pause, and he says “yeah”. Yet another pause, and I’m about to run out of the house, but then I say, ” you wanna play?” And he agreed!!!!!!

So we’re sitting there playing Madden. Me and this 15 year old kid, while you can still clearly hear Kyle slam banging his mother in the next room and I try to make the best of a shitty situation, so I let the kid win. Once kyle and Trina finished up, she gave us a ride home, (in her minivan).

We never spoke of that night again. However, 2 weeks later I’m in a different bar, this time with my buddy James. And no shit, Trina walks in. Before I can get a word out, James points her out and says “bro, about a month ago, me and my buddy tag teamed that girl.”

10. That got dark pretty quickly.

Finally! A chance to share!
It was about 5 years ago. I had a 22y/o employee (girl) which upon starting to work for me showed interest. We became Facebook friends and did a lot of chatting. She became friends with my wife as well (oh yeah… I’m married). One night over a fb chat which got intimate she mentioned that she always wanted to join a couple. I joked about it but was super turned on from the idea as my wife and I always thought about it but never acted.

About a week of continued chatting and she started getting both of us hotter by presenting the “what if rules”: no one falls in love , I’ll just be one time, no anal, etc…

She started luring me at work until one morning when I picked her up on my way to work and took her to see the ocean on our way where we made out for an hour or so.

We scheduled a Saturday for her to come over and watch the X-Man trilogy at or flat. She sat on the second couch during the first one, far from my wife and me. On the second movie she moved closer and snuck kisses with me when my wife went to the bathroom. Mid movie she put her hand on my thigh and got my wife’s attention. I kissed my wife and my wife put her hand on hers. I kissed her and she leaned to kiss my wife.

BEST SEX EVER!

3-4 HOURS

We ended up p breaking all rules. Almost got a divorce. Spent three months with her. Realized what a mistake I’ve done. Begged wife to take me back. Had to quit my job as it became awkward.

TL;DR: Had threesome with wife and employee. Best sex. Almost screwed my life.

11. OMG.

I (M) was involved in a fivesome with my then gf, another MF couple & another girl. Girls started with a show in the bathtub (pretty amazing) before we all moved to the bedroom. The two couples were sexing each other while the floater girl was going back and forth kissing the girls. Things were pretty hot for 2 minutes before I betrayed myself and released a silent fart. The stench filled the room within seconds. Everyone gasped at the stench and stopped fucking. Everyone was asking who did it (including me) and everyone denied it (including me). All 5 of us quickly left the room & things never did pick back up. This was 10 years ago & I my biggest sexual regret.

TL:DR involved in a five-way, I farted & ended it.

12. Screaming too loud.

Last year with my ex-boyfriend and some girl we go to college with. She was screaming the whole time while the three of us were fucking and was so loud that the people in the dorms around us could hear and were listening through the door and knocking. What assholes. But I squirted for the first time, so I got that going for me, which is nice.

13. This was like 10 years ago…

Will do a throwaway for this.

Male here, did a threesome once with two Transgirls that used to run their own website. Website has long been down (this was like 10 years ago) but still have fond memories of that night. They used to set up meets with their paying monthly members. All in all it was a fucking awesome night. I got to indulge in every fetish/fantasy I have ever wanted to try (pantyhose, foot fetish, sucking, getting sucked etc….). Think my favorite part was getting a stocking footjob from one of the girls while sucking the other girls dick.

Probably not what you were looking for in a response…..but that was my experience with a threesome.

14. :(

I’ve switched between right hand and left hand – does that count?

15. Banjo fingering!

Eh. It was okay. He was drunk and high on something, so I wouldn’t say he performed well. Plus he ended up trying to do too many things at once. Ended up going home with a sore vagina from ‘banjo fingering’.

16. Simply amazing.

Finally, my chance to share this story!

In a word? Amazing. Basically two girls picked me up at the bar and took me back to their apartment for “drinks” which was apparently a code word for me fucking both of them silly (as well as them going to town on each other) on their luxurious wrap around sleeper couch.
It was one of the strangest, most unexpected, and memorable nights of my life, but all in a good way. As I said, it was with two girls I had only met that night at the bar, so there weren’t any awkward moments because none of us really knew one another. Also, we were all drunk, so that helped smooth it out as well. They just knew what they wanted from me and from each other, and it all went swimmingly.

Needless to say the entire thing was incredibly surreal and even as it was happening I wasn’t sure if I actually believed what was going on. Pretty fucking awesome experience, though.
edit: I should also mention that there was absolutely no talk of a threesome (or sex of any kind) while we were at the bar, so the lead up wasn’t awkward at all. Just casual flirting and joking around, then they invited me back to their place to continue drinking, one thing leads to another and then we were all naked. And by that I mean that they walked out of the room to “make drinks” and when they came back they were in their birthday suits. That’s about the time my jaw, along with my pants, hit the floor. It’s pretty simple. They had gone out looking for a guy to add into their sexual plans for the night, and I happened to be the lucky dude they chose to bring home with them.

I sent one of them a text the next day saying I’d had a good time (no shit, right?), but I never heard from them after that. I see one of them occasionally but we’ve never spoken of it. It was the textbook definition of a one night stand and I am a-ok with that.

tldr – Got used by two bisexual girls I met at a bar in a gloriously unexpected three way, never spoke to them again. Wore out my hand with high fives the next day. Something I will never forget, but also something I probably won’t tell my future grandchildren.

17. Best night of my life…

It was AWESOME.
After graduating high school my girlfriend and I had the inevitable “so where do we go from here talk”, and we realized we didn’t want to do the long-distance thing. She left for summer session the day after my birthday, and we decided that my birthday would basically be a good bye party for all the grads one of my best friend’s houses.

At midnight when I actually turned 18, she grabbed my hand and took me upstairs. I was pretty fucked up but she said something along the lines of “hopefully you’ll never forget me” and when she opened up the door of the bedroom her best friend was naked on the bed.

Still some of the best sex I’ve ever had, and by far the best night of my life. We were all SUPER wasted, 2 18 year olds and a 17 year old can’t exactly handle their alcohol, but it wasn’t any more awkward than most high school sex. After we were done we smoked a couple bowls and drank on the roof and then cuddled in the master bedroom.

Great thing to wake up to. Best girlfriend I’ve ever had.

18. There is footage!

This was about a year ago.

Me and a buddy picked up this girl we knew from high school. Everyone knew that this girl was very promiscuous. We picked up a few drinks and headed to his house.

We were playing strip poker and everyone was down to our underwear. We had ordered pizza, so we heard a knock on the door. I had a funny idea to get my friend’s camera and act like the pizza guy walked into a porn shooting. The girl thought it would be fucking hilarious so she went ahead and took her bra off and opened the door. We joked around with the dude about taking a break from all the sex. He was awkward as fuck and kept staring at her tits like they were made out of gold (they were pretty nice.) I started feeling kinda bad for him so I threw in a fat tip.

After the pizza guy left, I just went over to her and started biting her ear and bending her over while grabbing her asscheek. My buddy decided to just start recording since he already had the camera out, and we fucked the living shit out of her on film. It was such a good night. I would do it again if she didn’t have a husband now.

Afterwards we just got drunk, ate pizza, and played battlefield til we passed out.

Edit: I message the girl on facebook and she does not consent to the film being exploited. :( OP would have delivered.