Me, My Friend & Fiancee - My best friend and I used to have sex with my fiance (now my wife of 5 years).
I am dead-ass, 100% serious when I describe this situation, my wife used to straddle fuck my friend. I'd straddle his thighs, my knees between my wife's knees (her knees were spread far apart). I'd fuck her in the ass.
I swear this is true, we did this particular sex act at least 25 times, 90% of the time the three of us could time our orgasms so that we all came at the same time. I mean the SAME time. Literally, the SAME time.
Were we just lucky or were we really good? I've got to tell you I remember many of those nights very well. I still vividly remember certain parts of our first simultaneous orgasm together - just like it happened yesterday.
I was in my wife's ass, "ahead" of my wife and our friend - meaning that I was having to hold back my orgasm as I gently slid in and out of her ass. I remember my wife kissing my friend as he massaged her tits - the two of them getting ready to cum together.
We three were in constant communication, each of us announcing how many seconds we were from orgasm. As I said, I was having to hold back, though I was on a razor's edge.
My wife and my friend then announced, after a methodical build-up, that they were going to cum. I remember letting myself go, my orgasm just moments from starting. I remember feeling my wife's ass hole tighten and begin to pump and pulsate, while at the same INSTANT I felt my friend's shaft jolt powerfully as he pumped out his cum inside her pussy.
I came immediately, my friend and I simultaneously ejaculating inside my wife's throbbing pussy and ass.
I got to tell you, it was great. As I said we did this alot over a year long period and had a really high success rate of achieving a 3-way simultaneous orgasm.
All this is the honest to God truth, as were we really fortunate to be able to do this? As I said, we three were graphically open in our verbal communication so that we knew EXACTLY how close we were from cumming. We stopped doing this when we had our first child but the memories are still fodder for our fantasies and we hope to get back into it soon. I have attached a picture from one of our sessions. We had the camera on "timer" and got a few good ones.
BTW, the membrane between the pussy and ass is VERY thin. I could feel my friend's shaft slide in and out of her like we were sliding against each other. I'm sure he felt the same thing. Another comment, we never DP'd her vigorously for fear of tearing her membrane, which really is amazingly thin. - Keith