Hi guys, love your site and I need some advice.

I have a hot fantasy that I want to do with my husband and I know he does too, but he is afraid or has hesitation. I have wanted to put on a strap-on, bend him over and give him anal for so long now. He knows that I want this too and every so often he will send me a message hinting that he might be into it. Like when he sends sexy pictures of couples together from your site and included are some of the ones with couples doing this.

I have not pushed him on it. He does let me rim him and stick my fingers in his ass. He squirms and loves when I do that. Should I just go for it when we are having one of these wild nights? Or should I talk to him first about it and let him know it is coming before we start our wild night? I want it to be great for both of us. Any advice guys? I do not want his worries about it to stop us from having this kind of fun.

– Dani

Dick of Dick-n-Jane.com
(layman with a website)

Hi Dani – we are not very active on this site anymore but your question came in and it has been churning in my head for a week. I had to reply because you sound like an adventurous, giving lady and your [very lucky] husband would be foolish to squander your desires. Especially since he has so much to gain from your little offer to peg him. Saying it is eye opening, paradigm shifting, relationship builder understates it… because it is also intensely pleasurable. I have written about pegging before, maybe the two of you could read Jane’s and my take on it together sometime.

I don’t know anything about your husband or you that you haven’t told me (obviously), so my advice here is a shot in the dark, really. It may be that your husband has a strong desire to be pegged but, because of the [unwarranted] gay associations attached to a man’s butt, he may be concerned about what his own pleasure might say about him. You can assure him until you turn blue but he knows he can’t brag in the locker room about being pegged without causing everyone else to grip their soap tighter.

To start, don’t dive into the gender-swap connotations of a phallic shaped object protruding from your crotch (I know, that’s what’s so much fun for you!) and pick up a modestly sized dildo that can later be used in a harness. Have a sexy night and make it clear upfront that you want to focus on his ass. Show him the dildo, point out the curve in it, and talk about the plan to stimulate his prostate. Then have fun driving him wild with your handheld dildo, your free hand, and your mouth.

How did it go? I thought so… now buy the equipment so you can have two hands free. The possible array of positions also opens up when the dildo is attached to you (think him on top for a change) and he’ll never look back.

Have fun Dani!
Congratulations Dani’s lucky ass husband!