Happy Valentines?   :( 

Well, I semi-regretted it. Like it was fun, but maybe I would have liked a better 3rd.

Anyway, freshman year of college I was into this guy and he had slept with this other girl in our friend group but was also into me. Valentines day we're all single, we go at it, and we have a great time. Later I end up dating the dude and like 2 or 3 years into the relationship he cheats on me with 3some girl. ooglecat

Not Cute.

It was me, my girlfriend, and my friend. Well, ex-girlfriend now because she started dating my friend afterwords. TreGoa64

Got an unwelcome surprise......

Didn't realize the other guy was into me

Got an unwelcome surprise. grapestreet9

This is why it's really important when you do anything kink-related, even if it's supposed to just be a "vanilla" threesome, to negotiate rules beforehand. What's okay, what is definitely NOT okay. That way nobody gets unpleasant surprises.

Even when you think it's obvious, like "no you may not penetrate my anus without asking," some people may assume that it's okay. Raudskeggr

A Movie Plot. 

I (f) had a threesome with my bf at the time (now my ex) and a mutual female friend of ours.

He ended up cheating on me multiple times with her afterward, and then ended up becoming obsessed with her, almost to the point of stalking. He even stole a friend's car to go see her. It was wild. Lol. chengsao

Avenger.

The guy was built like a Superhero, so I spent most of the "experience" trying to suck my gut in.... praying for it to be over. OldmanShed

Blood is a No. 

This is my time to shine.

When I was 19 I (F) was invited by a couple to participate in a threesome. They were both super hot so I was pumped!!

So it starts and everything is going fine, we're all touching each other whatever. We get into a position where I'm sitting on her face while she lays on her back and her boyfriend has sex with her missionary. All good until the boyfriend kinda shoved me off her? I was like wtf? Then she gets up and her face is absolutely COVERED in blood. Like lion after eating a zebra blood. It's literally everywhere: the sheets, the pillows, her face, his hands, you get the point.

Turns out she sliced the inside of my vagina with her very sharp acrylic nails (they looked very nice just don't feel the best against my fragile vaginal membrane) and I was bleeding profusely.

I cleaned myself off and was like....."I'm gonna go..." and they were like bye...

It's still one of my absolute favorite stories ever. Reddit

Talons.

I'm gonna cut straight to the dish....

My buddy's big toe nail grazed my butthole while trying to switch positions with her. I never told a man to cut his toenails before and hopefully never will again. ImpossibleWeirdo

Oooof. 

I don't know if I regretted it per se, but I was the third wheel. After the sexcapade we passed out and later on that night her boyfriend went to the bathroom. She then cuddled up to me and said 'that was really fun and all but if we do this again can we get somebody I am attracted too.' Then her boyfriend walked back in and she realized that I wasn't him, I could literally feel the room fill up with awkwardness. Windbelow616

No Touching.

I had a threesome with two guys and it was kinda awkward seeing how they were trying not to touch each other during the whole thing. It was cool and everything but they were so trying to avoid any kind of touching and I get if two guys don't want their members to touch but they wouldn't even touch legs by accident and that is hard when you're getting dp'd by two tall guys lol. suki_ta_

Hindsight. 

I mean, i guess it wasn't necessarily unexpected, but it just ruined my relationship with my girlfriend at the time. We had a threesome with a female friend of hers, and she couldn't get the image of me having sex with her friend out of her head. She said that she couldn't shake the feeling that if I truly loved her, i wouldn't have been able to sleep with someone else.

Worst part of it was my gf was essentially my dream girl, and the girl we added to the mix wasn't nearly as spectacular as she was. So i traded a longterm relationship with my dream girl for one night of a threesome, and i would NEVER have made that trade with hindsight.

That said, waking up in the morning with a hot naked girl on each side of me was pretty incredible. Buffal0_Meat

OUCH!

I had a threesome with my girlfriend and best friend. She left me for him. They have been married for over 10 years. Tacomancer42

Salty Feels.... 

My ex came home from the bar with his friend and asked if I would have a threesome with them. I reluctantly agreed after drinking a little. The experience was pretty good but my ex was so insecure and made my life miserable for a few weeks after that because he was salty about the fact that I actually enjoyed it. No idea what he was expecting. Viiibrations

I never talked to those morons again.​

My girlfriend at the time was hanging out in her bedroom with her roommate. I was watching TV in the living room.

Her roommate comes out of the bedroom wearing a sheet. She looks at me and says, "We're having sex back here. You should join us" and drops the sheet.

She was physically attractive, but I didn't like her personality at all. I said no.

She shrugged, then went back into the bedroom. They were in there a good hour or so, when my girlfriend comes out, naked and crying. She kept apologizing for "cheating on me". I told her it was ok, I understood, everything was going to be all right.

About two weeks later she dumps me. Said she couldn't trust me BECAUSE I DIDN'T DO HER ROOMMATE.

She dumped me at my birthday party. She messed with my best friend that night in the room next to where I was sleeping, then came in afterwards to make sure I heard it and knew what was happening. She asked if I was okay, I said no, she started laughing.

We were all sleeping in a cabin in the woods and I was drunk as hell, so I walked away.

I never talked to those morons again.

I figure I got about ten miles out and passed out on the side of the road. Woke up when a couple of good ol boys tossed me in the back of their truck. They were going to drive me to the hospital, but I told them what happened and they drove me home... About two hours away. I gave them twenty bucks for gas and they turned it down. DoomOne

Cry not Pretty....

My ex gf's friend stopped us in the middle of it to ugly cry for the rest of the night about how she wanted her ex back... needless to say it stopped pretty quick. Grt38

Back Up Kids....

I was the third for this couple, they were both really keen on me. The experience was actually pretty normal, but afterwards they kept pestering me for more. I had realized I wasn't that interested in the both of them and kept politely declining their offers. They never stopped offering, so I finally had to say I wasn't interested. I'd see one or both of them around occasionally and they'd give me a half-hearted smile. A_Sassy_Sammich

ALONE....

I had really strong feeling for this guy, and we he been flirting for a while. It was going well, and one night I was over at his house with another female friend of ours. We got drunk, one thing led to another, and we had a threesome.

Now they are dating and I'm still alone. PinkAcrobelle

"Looks like you two are good, I will leave you to it."

I was asked by my girlfriend to have a threesome with her and her best friend... a friend I had known for a long time and who had actually introduced us.

A couple of minutes into it I realized that my girlfriend was not remotely interested and had pulled back... which made it awkward because I was not remotely interested in my friend sexually... I only agreed to it because my girlfriend asked and she had been a little distant lately... I thought it might help rekindle the relationship.

I carried on and did my best to make my friend happy... and then all of a sudden my girlfriend stood up and said "Looks like you two are good, I will leave you to it."

I stopped what I was doing and asked WTF was going on, and eventually they explained that the whole thing was a scheme for my girlfriend to break up with me and "pass me over" to her best friend who apparently had a crush on me.

Needless to say this did not go down well, and I ended up losing both of them from my life. hokeyWB

Not with my Wife...

My wife and I had a threesome with a friend of mine that had recently left the military. Everything seemed fine until he told us he was in love with my wife, his brother also happened to be my best friend (we're not as close as we were though) who is super insecure and apparently also had feelings for my wife.

Later my military friend was diagnosed with schizophrenia and his delusions were telling him I was the most evil person on the planet, and that aliens were gonna give him super powers and disintegrate me (that is not an exaggeration.) He now gets monthly shots from the VA and he's doing a lot better. lemonyfreshpine

​Late to this discussion.

Late to this discussion. Not exactly a one time threesome but more of a live-in crazy toy situation. So about 6ish months of threesomes and poly relationship. The dude was super sick and took meds all the time and had tons of doctors appointments. They told me he had Lymphatic cancer. This was only part of the truth.

A friend of theirs came to visit one day and saw the situation, asked me if I knew why dude was so sick and I responded "well yea, he has cancer" and I will never forget the look on friends face when he realized he would have to be the one to tell me that dude had AIDS.

I confronted dude and he lied to me. Irate, yelling and screaming at me for even thinking about accusing him. I called his wife in tears and asked her. The first words out of her mouth were, "I'm so sorry. We never meant to hurt you."

So yea. Never again. This happened 12 years ago. I was 17 at the time. I got lucky in that I didn't contract HIV. I still get tested annually and disclose that I've been exposed to it to any potential partners, but it definitely could have ended much worse. Dead_in_the_BrainPan

Don't Outdo!

I had an unplanned threesome with a close friend and her boyfriend. He's well endowed and apparently she couldn't handle giving him oral, but I didn't know that and while we were fooling around I gave it to him. Like, really good. Like so good he wouldn't stop talking about how good it was and asking why she doesn't give it like I do. It made her insecure and put a strain on our friendship as a result. Even after they broke up, my friendship with her wasn't the same. D0rkasaurusRex