Sintellectual Sundays: June is Gay Pride Month
June 2, 2013
Homemade Cock & Ball Torture
June 18, 2013

Anal Training: I’ll be gentle, I promise

AssholeHandsignWhen you read the title, did your little puckered hole twitch a little? Aww, don’t worry, my nervous little subbie, I’ll be gentle with you. You can trust your skilled Mistress Jane with your anal virginity. After all, I want you to like it, perhaps even to beg for it one day, so I’m hardly going to have you ram a baseball bat up your sweet innocent ass…unless that’s how you like it (Ms Reaghan, a lesbian femdom with a penchant for strap-on training, owns a 15-incher!).

Why You Will Like Anal Play

Boys, you have a sex organ in there and it loves to be stimulated! That’s right – the prostate, the P-spot, the male G-spot. Even mild external stimulation will get you going, which you’ll see evidence of in the form of extra pre-cum. Imagine then how good even a tiny bit of penetration would feel… the tip of anything, though in this case I’m talking about a finger, a small toy, a conveniently shaped vegetable – not a cock. Because wanting your ass played with isn’t by definition gay, it’s simply feels gooood. Your home offers up a cornucopia of beginner insertables,so you can forget that lame excuse and get right to it on our next phone sex call!

The First Time Is Always Awkward

Bizarre foods and sex acts have something in common: they’re both such a surprise the first time you experience them, that you can’t judge it by the first ‘bite’. You need to try it twice to determine if it might be your cup of teabagging. Every lucky real-life man I’ve inducted into the realms of anal pleasure “hated it” the first time…then within a few weeks, they all wanted to try it again. Most wanted it a third, fifth, twenty-fifth time. Will you join their ranks?

Equipment for Anal Training Phone Sex

You need very little, actually. Lube of any kind, even olive oil, and something 6″ or less and fairly slender will serve our purpose: a carrot, a marker, a toothbrush, a taper candle…feel free to improvise here. There will be some playful teasing with your sexy makeshift toy, some stimulating instructions from me… and before you know it, you’ll no longer be wondering if you’ll cum – you’ll likely find yourself begging for sweet release.

4 Comments

  1. Oh my my my….I was smiling to myself as I read this. I used a highlighter once for a “first time toy” and while my pet on the other end in the beginning was whimpering like a bitch, by the end he was moaning like a girl and squirting all over himself. Ms. Jane, you certainly have a way of creating an unforgettable visual. Your callers will NOT want to miss out on this little treat! (Did you notice the guy next to you on the plane squirming in his seat when you got finished with this little gem?)

    • admin says:

      Ah yes, the joys of handwriting a blog post on a full flight. I did indeed notice that the “middle seat loser” was rather fidgety… 😉

  2. Probably because you offered him a Sharpie permanent marker when he asked to pass by to use the lavatory.

  3. […] I’m playing with an anal virgin, I start with my fingers.  Our first session, I might not even insert it, just press lightly on […]