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Anal Play Phone Sex with Mistress ClaireOne of my favorite things to do with a new sex partner or even a friend-with-partial-benefits is to introduce him to his own ass. Seriously, whether he’s 23 or 53, I’ve always been the first woman to “go there” with the exception of one (the body worship artist, heh). Now I’m not even talking about strap-on play — I mean even a fingertip!

Anal Play: Being Gentle With a First Timer

Unless the guy has indulged in a little anal masturbation before, first time anal play is usually fraught with mental gymnastics about whether liking something in his ass makes him gay. I just tell him to slap that voice down and let’s get started. First, there’s the teasing pressure of my finger tip, which usually makes him impatient for the whole finger. Once that happens, it only takes a minute to work him up to two oiled-up fingers. Does it seem like he wants more? Well then I cross those two fingers and penetrate in a twisting motion while my other hand works his cock.

When Fingers Aren’t Enough

The second time, I give him a choice of things I’ve gathered from around my house…usually a ridged hairbrush handle, a smooth taper candle and a carrot. I handle and stroke each one of them, extolling their individual virtues for anal insertion so he can make an informed selection. However, just hearing me go on about this often results in “all of the above!”, lol. These things are all longer than my fingers, so I explain that to get it all in, he’s got to make like he’s trying to push it out and then it just slides right in. Heh, he didn’t think it would be all that different from my fingers, but a whole new world of pleasure opens up at that point!

Keeps it sassy!
— Claire —