I had an interesting experience this past Saturday night. My wife and I started the weekend off early Thursday with a hotel getaway. We had sex off and on several times Thursday night. Of all the sessions, I think I orgasmed two or three times - one of those times while having a long slender dildo worked in my ass. Friday night back home, the wife wasn't physically up for sex but did provide some prostate massage while I masturbated to another intense orgasm.
Saturday night it was game back on as my wife brought our new rabbit vibrator and laid it on the bed. She is hooked on that thing and the powerful O's it gives her. Once we had moved on to intercourse, I was stroking into her steady as she worked her clit with another new vibrator, a small but powerful WeVibe Tango. I was pacing myself and focusing on what she needed to pull of a couple more orgasms.
Once I was sure she had got hers, I ramped up the intensity to see if I was going to be able to get off - as sometimes my wife can't take the intensity that it takes for me to orgasm after successive rounds of sex. She held up like a trooper and I had a powerful but dry orgasm (no semen). I've had these on occasion before so I knew what I was feeling. Just as I was explaining to my wife that the powerful orgasm I just had was a dry one, I took a few more slow deep parting strokes preparing to pull out, when out of nowhere I had a second powerful orgasm, this time pumping out a considerable amount semen - especially for as many times as I had already ejaculated over the weekend. I told her i just had a double orgasm, but I'm not sure she believed - or if so, she didn't really seem to grasp what an event it was for me.
If I could do that all the time, I certainly would. Two powerful orgasms with a 10-15 seconds of each other ranks as one (2) of the best ever!
The closest I ever came to a multiple orgasm prior to that experience was a few times that I stopped stimulation, but not soon enough to avoid ejaculation - then following up with another orgasm a minute or two later.