So we finally got a chance to try out the prostate massager this weekend. It was pretty interesting. It fit right over the head of my vibrating wand, and I lubed it up and shoved it in him.
His poor butt had been neglected for so long, though. It took him a minute to get used to it.
I like it. I like playing with it. He’s a bit on the fence, though. I’ve fingered him and played with his prostate, but he’s never really had a whole lot of pressure there before. The shape of it and the pressure it put on him took some getting used to. But all it took was a couple of minutes and a little bit of teasing his dick, and he was squirming and moaning like the delicious little slut he is.
Unfortunately, he wasn’t able to cum from that alone. That’s been my goal for awhile, now. I want to see if I can get him trained to cum exclusively from anal and prostate stimulation. And so far, I’ve been unsuccessful. But I’m going to just keep working on it.
Besides, how awesome would it be if I could make him cum without touching his dick? I’d never have to take him out of chastity again. I could just fuck his ass to milk him and then put him away for the night.
Omigod, that would be so awesome. And I’m determined to make that happen one day.
Domina Jen 
Ah great minds think alike….well maybe not minds…anyway, I bought my first ever sex toy…http://writingthebody.wordpress.com/2013/07/25/prostate-erotics-stuff-you-buy-and-other-mad-things-about-me-and-myself/
And well, it is the prostate thing. It is hard for him to cum that way…I think it is better to milk it…the thick stuff just keeps oozing and oozing. When he cums, later, which is still possible (but it will need a bit of hand work I am afraid), the cum is thinner than usual because of the milking. Goodness, why does he not love it? The feeling is glorious….
An award for you….I made it…the free rider award….as you can imagine. http://writingthebody.wordpress.com/
God where are you…..a further award…a liebster like you! http://writingthebody.wordpress.com/
O where are you and Kazander? What is happening to you? I miss you…..
I missed you too. Sending cyber hugs your way.
O thank you….thank goodness you are back!!! xx kisses for your feet or the floor or whatever it is you let me kiss…..and hugs too.
Aww, you’re too adorable, little one.