I am being flooded with PMs from men looking to explore their glory hole. Here’s a quick FAQ:

1. I recommend the Aneros Helix Syn to start with.
2. You will need to learn and develop kegels. It’s how you “work” a prostate massager (it isn’t a dildo; you don’t fuck yourself with it).
3. You most likely will not have a prostate orgasm the first few sessions. It might be the first session, it might be the 301st session — it’s different for everyone (it was about 2 months for me).
4. Do not dive head-first into pegging unless the woman is experienced and knows exactly what she’s doing. Women do not know how to fuck, naturally, so they can really hurt you if you aren’t careful.
5. Steal your girlfriends’ vibrator and hold it to your taint while you work the massager. Encourage your girlfriend to use the vibrator on your taint when she blows you (this has nothing to do with butt stuff, this is just an awesome pro-tip I give to women any chance I get).
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As a man, I’ve had the flip-side of this issue.

I own two Aneros prostate massagers, and I know how to use them. I’ve broken them out with let’s say, 5 partners.

3 of them were simply not into it — no biggie, I understand.
1 of them was flat-out disgusted — grow up, sweetheart.
1 of them was down, but more-so out of curiosity, less so out of experience or eagerness.

My last girlfriend expressed interest in pegging, but she chickened out when I was absolutely up for it (I even picked out some toys). I think she was trying to “freak me out” I really don’t understand the phobia. I’m not homophobic; I know I’m not gay, and I know that having my prostate stimulated feels incredible, especially when there’s a pussy throbbing on my cock at the same time.

And rimjobs? Jesus, at this point I’m convinced they’re only a thing of porn. Getting rimmed by a woman who actually wants to do it, rather than just doing me a favor, is a huge fantasy of mine (especially if she brings her girlfriend).

But seriously, what’s a dude gotta do to get a girl to play with his ass? I will eat your ass until you stop me, and I will love every moment of it. How come I know how to use all your toys better than you do, and am super enthused about doing so, but you won’t even entertain the idea of me using my massager while I fuck you?

I thought these were supposed to be progressive times.