Worst Threesome Experiences?

the one that comes to mind for me is more of an amusement....

having to tell two guys to get some rythm becuase i'm not an accordian!
 
How about arranging a 3way for your boyfriend, only to have all his fraternity brothers look in the tiny crack at the top of the window not covered by the blinds? They said they wanted to "verify for themselves that their brother was actually that lucky." Doesn't change the fact that they all saw me naked...
 
My worst (and best) experiences

Okay, so my "worst" threesome experience didn't even include sex exactly...

I met this couple on-line and drove three hours to meet them. We met at a restaurant and had dinner, and they were even hotter than their pictures. We were having an okay conversation (a little awkward), when i ask:

"So how long have you been married?"

They both gave different times and then he said "We're not married to each other."

I said, "Oh...do your spouses know about this?"

They didn't. Their partners in marriage didn't have any idea about their bisexuality and their cheating. I said a few words about it and they immediately said I was being "judgemental" and "closed-minded." We had a brief discussion (not heated, but definitely hostile). After drinks, we went to a swingers club (my first and only experience) and I had to pay something like $80 to get in.

I barely saw them the rest of the evening. Later, I found out that they had left me (they were my ride). I ended up having to call a cab to pick me up...not exactly a high point.

Now, in fairness, my BEST experience:

I had been chatting with a girl for a while on-line and we really clicked personality-wise, but we were long-distance and just friends for the most part (she lived in New York City). I chatted with her through her dating experiences...and then she told me she had started dating a guy who was bisexual like me, and how much it turned her on, but she never thought it would before.

She sent me pictures of him and I told her I thought he was really hot. When I visited NYC, I met them both at their apartment in Brooklyn and we had drinks and dinner, but nothing happened.

On the phone that night, she said that they had the most intense sex afterwards talking and fantasizing about me. I said I should come over tomorrow and she said "You should."

When i walked in, the house was dark, but there were candles lit. She called to me and I walked to the bedroom towards the back and she was in a bath towel on the bed. We started making out when he came out of the bathroom, he just crawled up behind me and joined us.

We had a marathon sex session, with one person taking a break here and there for drinks, cigarettes, naps, showers, snacks...it lasted until the sun came up.

The chemistry was perfect, there was no expectations of performance (if someone wasn't hard or wet, the other two played), and everyone was very open with each other.

Unfortunately, they didn't work out as a couple (had nothing to do with me!), and she now lives in Texas and she's on my Facebook.

She's married to a hot, cowboy-looking musician and I fantasize sometimes...WHILE LOOKING AT HER G-RATED FACEBOOK pictures.

Yeah, that's how hot it was.
 
My bf and I had picked up this cutie who said she was bi at a local club. Well we rode home together and she and I made out all the way home. It took about 5 minutes till we were all in the bedroom and strip naked ready for so serious fun.

What fun. All she wanted to do was fuck my bf and forget about me. No way. She was told to get out.
 
Worst but funniest

My worst threesome was pretty funny at the time too.

My then gf and I would meet girls online etc and one in particular we saw quite a few times.
One of these times I was lying along side the other girl looking down with her at my gf going down on her. The girl wasn't shave and had a nicely trimmed black bus and as I was watching, a thought entered my mind I couldn't get rid of and I started to laugh.

The both stopped and asked what I was laughing at so I told them that my GF, from that angle, looked like Tom Selleck.

I was kicked out the bedroom (yes I know, rightly so), and they made sure they made plenty of noise all night
 
My worst threesome was pretty funny at the time too.

My then gf and I would meet girls online etc and one in particular we saw quite a few times.
One of these times I was lying along side the other girl looking down with her at my gf going down on her. The girl wasn't shave and had a nicely trimmed black bus and as I was watching, a thought entered my mind I couldn't get rid of and I started to laugh.

The both stopped and asked what I was laughing at so I told them that my GF, from that angle, looked like Tom Selleck.

I was kicked out the bedroom (yes I know, rightly so), and they made sure they made plenty of noise all night

That is hilarious.
 
I'm a little shocked that no one has mentioned the "We THOUGHT we were strong enough to handle a 3some" scenario... I've been in it a couple times, on both ends.

When I was very young (22 or so) and married, my wife had a friend who we were close with, and we were all very sexually open. We had several 3somes with her, most of them successful, although the first couple were a little rocky because my wife got the impression that I was paying too much attention to her friend. I thought I was doing my best to make sure that DIDN'T happen, but looking back, I think that no matter how much attention I was giving her, the wife was gonna be a little jealous. Eventually she got past that, and we had ffm's with that girl and a couple other of her friends at different times. Had one mmf as well, which went just fine (except for the guy being too nervous to cum, but that's a different story).

On the other hand, I was part of a 3some with a married couple, where we met online, agreed to have drinks first... The first red flag was that she got drunk pretty quickly, and started making loud comments that others could hear, about our impending 3some-to-be... didn't bother me that much, but it was a little obnoxious... when we finally got back to their place and got naked, things went well for about 15 minutes, but at some point (maybe when he and I were sucking each other?) the "jealous" button went off in her head, and she started yelling at him... they got into a pretty serious argument, while I sat there VERY awkwardly... she stormed out, he followed, I started to get my clothes on. They came back in about 5 minutes later, said things were ok, and we actually ended up having fantastic sex in all combinations! But it was still very strange, and I didn't hook up with them again after that. Worried she might really go off on him/me next time. :D

So, today's lesson is, you can do all you can to make sure everyone involved is totally cool with the situation, but sometimes someone doesn't realize how much it bothers them to see their S/O fucking/sucking someone else, until it's actually happening. So that's an inherent risk.

Good luck and have fun tho! I've had numerous other 3somes that have been amazing with no drama whatsoever, so it's definitely possible.
 
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