I’ve been curious for a while about anal play while I’m pleasuring myself. I’ve heard it generates a more intense orgasm. I can take fingers, but I’d like to try something more (on the smaller side of course). Being a guy, is there a position or toy that will give me the best penetration while pleasuring myself? I’ve never reached out to anyone regarding this before. Being a straight guy, there’s not too many people you trust with whom you can mention something like this.
Your question reflects the classic conflict between pleasure and shame we’ve all been socially force-fed. You’re right! Prostate play — reached by going in and up the ol’ backdoor — can lead to more intense orgasms.
You’re also right that identifying as a straight man limits who you can talk to about receiving anal pleasure. Seems weird, as straight men are so easily socialized to talk about their penises. Though straight men have been granted permission to seek sexual pleasure, alright, it’s only certain kinds. The prostate’s location really rips up that permission slip.
As you’ve discovered, the prostate is reached easiest with a curved shape — whether hands or toys — and pressure applied to the inner wall of the rectum. That’s right, up your butt! Charlie Glickman, co-author of the exceptional The Ultimate Guide to Prostate Play, describes what you’re looking for as “a plum half-buried in the sand.” Once found, use a press-and-drag motion to massage it.
Reported reactions to prostate stimulation include longer, more intense orgasms with aftershocks, stronger ejaculations, and all around sexual sparklers. Sounds pretty nice, yet many straight men can’t get past their fears — or sphincters…continue reading…
