Strap-on Anal Training: Stretching and Fucking Him Hard

The strap-on anal training he craves!

A strap-on anal training session isn’t complete without a deep, rough fuck! And, of course, the toy is the main attraction. So trust me, I have plenty of toys ready to go when it’s time to fuck my sissy’s tight little ass! Sometimes I even give him a pegging punishment with some very creative toys, and other times it’s full-blown costume playtime. For the most part, though, I love to warm him up with an enticing butt plug pegging session. Often, I’ll give him a little ‘homework’ that will warm him up for a strap-on anal training session. It’ll be something more manageable, such as wearing a butt plug all day. That really helps stretch his tight little ass and get it ready and relaxed for me.

And once he comes home, we get to have all the strap-on anal training fun that we want! First, I make him shower up so he gets his booty ready to play. And then I’ll often give him something to try on for me. Sometimes it’s a little on the sissy side, and I’ll make him wear a cute lace thong. Other times, the thong just gets in the way! So I’ll have him put on a mini skirt with no panties. Isn’t that so much easier to fuck? I certainly love it, and so does he.

He bends over eagerly.

Just like that—showing his ass off and holding it up in the air for me. When he’s all dressed up, or even just bare and naked, I love to see his ass! Sometimes I even tease him, ordering him to “assume the position.” But often, he does it all on his own, knowing exactly what I want. Isn’t he such an obedient little sub? I bet you’d be very obedient and greedy to take my big toys too! Whether or not you behave, we’ll be having a hell of a strap-on anal training session. I can be sweet and gentle or very rough and turn it into a punishment session. Either way, I LOVE giving a good, rough pounding with those toys.

But the best strap-on anal training session always involves my biggest strap-on. I have an impressive, thick, twelve-inch black monster that even vibrates! Doesn’t that sound delicious for a good ass-fucking? It has a nicely shaped head, so I often have to lube it up very well. Of course, this also involves warming up my little sissy slut’s ass with those butt plugs and toys first. Could you take such a big cock without being stretched out slowly first? If you’re greedy to try it, I’d certainly let you have it…

But the best strap-on anal training takes time!

Inch by inch, I love slowly stretching my sissy’s ass out. Sometimes I even have him lay on his back for the occasion. Because it’s always so much more fun to see the look on his face as he watches me slide my cock into him. It’s so exciting for me to make him fit it all. As all of it slides in, you can imagine the feeling, the pressure. The waves of ecstasy rock over your body, especially strong when the vibrations from the toy brush gently over your prostate. Strap-on anal training can be such a rush of pleasure. I certainly always want to dish out more of it. Could you handle a rough training and stretching session like my sissy can? Call me—I’m sure we’ll both love to find out.

Call Kali 1-888-317-3123