This week’s Erotic Journal Challenge is:

What would you like to explore in your sexuality over the next 30 days? Within the next year? Let’s keep it small, focused, and specific. Something you can plan ahead for and measure progress. And in the planning, consider the who, what, where, when, why, and how. Who would you like to explore this with, or is this a solo mission? Is it something taboo, that you are afraid of trying or telling your partner about? Why haven’t you already done it…or if you have, why do want to try it again? How are you going to go about reaching this sexual goal?

Right away, when I came up with this prompt, I was already thinking what I’d like to try…something small, that would actually be a challenge for me…something I could actually achieve that would feel like an accomplishment…something out of my comfort zone (because, really…how else would it be a challenge, right?).

It didn’t take much thinking, really. I knew I wanted something that involved Mr. D, because things are going well with us, and it seems like the perfect time to experiment and try something that pushes my sexual boundaries. And since I’m also trying to put his needs front and center, I knew I wanted this challenge to be something that would bring him pleasure.

So, my choice is prostate play.

We’ve done a little of this together, though not much. Once, long ago, I bought and used a strap-on on him. That didn’t go well, because the power dynamic was off. Neither of us felt comfortable with me in a position of power. BUT, using toys and vibrators, and fingers to bring him pleasure during sex of a blow job? We haven’t done much of that. And I don’t think it’s because he wouldn’t like it.

He does it on a regular basis to me, slips a finger in my back door while pleasuring me orally…and yes, it feels good, even though it makes me a little uncomfortable (embarrassed). It’s silly, I know, to be embarrassed about any mutually pleasurable sexual activity, especially when he initiates it. Anal sex has also been good for us, so I can’t imagine Mr. D not at least being willing to try if I suggested it. He’s much more open to experimentation than I am.

So, there’s that. My goal is to posit and initiate a little prostate exploration, with fingers or a vibrator, during both a blow job and sex, within the next month.

I’ll let you know how it goes.

5 Replies to “The Erotic Journal Challenge: Prostate Play”

  1. In my journey with my “teacher” Maria, I began learning ejaculation control. Next session as I gained control going from almost immediate ejaculation to now almost unlimited control she has gradually introduced me to anal stimulation and prostate massage. Learning to relax is the biggest thing. Now in a 2 hour tantric lingham session I enjoy a series of anal penetration and ofter kneel on all fours while she works both at the same time. Luxury! There’s so many nerves around the anus.

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