Masturbation with anal stimulation

I have used a small anal plug and wow talk about shooting and intense.

 

When I was in my very late teens I dated for a very short time a woman who was way more experienced than me (I was the play toy) and she tried this on me and admittedly it felt foreign. I'm not homophobic and given the right drunken state moment and being single would probably do anything, but that aside being "plugged" at the time of orgasm didn't do much for me. Now that said I've never had a prostate massage and expect I probably never will as I don't think my wife is up for learning such things. But that's okay by me.

So bottom line. Thumb up the but didn't do anything for me...

 

I had a girlfriend that wad always messin aroud down there. Finally I told her ok go ahead. First in bed then the shower with me jerkin off. It took awhile for me to get passed the whole" guys shouldnt do this stuff" thing and man am I glad I let her. I love it and she totally loved doing it.