couple times, its usually hard to time it because if im making my girl cum i wanna make sure she got to fully enjoy it before i blow my load and stop. the best is when the girl cums and then ur orgasm feels so good that it makes her do it again.
Frequently it happens for me and my boyfriend. Most of the time i'll have like 1 beforehand and then i'll have a second when he's having his. It takes my dude a little longer to get off.... for whatever reason. I think he just does it so he gets to have sex longer.
I could probably count the times that happened to me and my last girlfriend on my fingers. I couldn't usually tell when she was there because I'd be concentrating on whatever I had to to keep going and she hardly ever told me when I could come. I don't know if it was because it ruined it for her or it was because she didn't like being in control.
Yes, I love it. I get off on the other person's pleasure. I think its one reason I haven't had success with blow jobs, because the person blowing isn't really feeling the same thing as me. Being the bottom, I can usually cum pretty fast but I can wait for the top to get there too. When we're both there, bam. Ecstasy.
Mine usually coincides with her thirds or fourth. So its technically simultaneous, but she gets four times as many. My way of making up for blowjobs not giving her an orgasm.