First off, your blog is unbelievably sexy! I find it so sexy that y’all play with strap-ons. I would love to put one one my girl and have her fuck me (I’ve played by myself with eggs and LOVED it). How did you get he to do it? My girl is very inexperienced sexually and I’ve just introduced her to the magic of toys. Thank you!

Dick of Dick-n-Jane.com
(layman with a website)
Thank you so much for your kind words about our website, positive feedback never gets old! ;o)Your ability to receive unhindered, and sex-life changing, anal stimulation is entirely dependent on your partner and your relationship with her. You can’t force anything on her, she might just end up resenting you for it, or worse, passing judgment on you as some sort of sexual deviant (as if that’s a bad thing). I recommend baby steps… and including her at every step.

The worst mistake you could make is to explore a new sexual fantasy in her absence, fall in love with it, and then spring it on her out of nowhere… already experienced and rearing to go (pun intended). She needs to be in the loop, at least with knowledge of your desires, from the start. Exploring together is fun… being left behind and the trying to catch up is not.

Receptive anal sex, even with a dildo, is generally associated with homosexuality. Our culture assumes that only men who like other men have pleasure centers buried in their pelvic region, as if orientation has something to do with nerve transmission. This may be your first hurdle with her and will require communication and maybe some mutually pursued self education. Jane and I were both listening to the Sex Is Fun podcast (first 100 episodes) when I shed my own aversion to anal play for myself. There has been other sources of information and inspiration since, but it was a good place to start. It helped Jane and I both get past some of the stigmas associated with anal play for men.

I’m a firm believer that male anatomy (not female) was the evolutionary driver for the sensitive pelvic tissue which forms the prostate in men and G-Spot in women. It is common anatomy we share… and if she can understand her own response to G-Spot stimulation she can understand yours. Even better for her… once you explore prostate play it will better enable you to understand HER sexual response! Tell her that… it’s not smoke, it’s true.

It sounds like you have already started exploring on your own, I hope she has [at least] been aware of your interest. If not, broach that topic soon. I feel it is important to explore your own pleasure before asking a partner to pleasure you, you may want to read this blog entry on the topic. Once she understands that it is a real interest of yours, and that you are attaining pleasure from it, her interest in participating may grow. Allow her to witness your pleasure, participate in it, contribute with some prostate massage, and before you know it you’ll be shopping for a harness together.

Take it slow Ricky, be patient with her… you may be asking her to change some fundamental misconceptions about male sexuality. Your nurturing of her through your own sexual exploration and development will yield great rewards; sexually for you (obviously), and for your relationship as well.

Best of luck! Be sure to come back and keep us appraised of your progress.