So over the last year or so the gf and I have been using a strap-on on and off. I never thought she'd be into it but she seems to really enjoy it.

Frankly, I have come to love it myself and get really turned on when she initiates it (I am still hesitant to ask for it). The problem is that I have never had one of those legendary prostate orgasms. The feeling always gets to be too tiring down there and I feel I have to stop. Is the strap-on maybe too big?

We've done a number of positions. My favourite is doggy style but she really likes me on top and seeing my dick bounce as I ride (I like this too). But still, I've never had an anal orgssm, though some of my dick orgasm cumshots have been epic.

Does anyone have advice for nailing that prostate orgasm? Does it just take more "practice"?

I'm getting hard just talking about it, but she's gone for the weekend

You may want to consider getting a prostate massage device such as an Aneros. There is a learning curve for getting to the point of having orgasms with prostate stimulation, but it's a fun ride. You can practice solo and then introduce it into your playtime.

She might not be getting the right angle. Squat a little, lube up your middle finger and reach from the front between your legs. With your palm resting on your taint, insert your finger and sort of close you palm. Reach in deeper. When yur fingertip feels a very smooth almost balloon type surface, your are poking your postate. She needs to go for that!

She might not be getting the right angle. Squat a little, lube up your middle finger and reach from the front between your legs. With your palm resting on your taint, insert your finger and sort of close you palm. Reach in deeper. When yur fingertip feels a very smooth almost balloon type surface, your are poking your prostate. She needs to go for that!

Just keep trying - practice makes perfect! Until recently, I had never had a completely hands-free orgasm. However, I would masturbate anally with a dildo and manually at the same time, and when I was ready to cum, I would stop jacking and just stimulate anally. I would squirt a little, and when that stopped, go back to jacking, and cum again - almost like a double orgasm. Recently, I was masturbating anally in the shower, and had my first hands-free. I wouldn't say it was life-changing, but it felt great. I have an Aneros also, but never had a hands-free with that. Maybe I was in too much of a rush to cum. In any case, cumming with a dildo or plug up your ass is intensely pleasurable, hands-free or not.