The first time I knew I was a sissy trainer was the time I caught my step brother in my room. He was wearing my panties and bra, parading around like a little femboy he is. So decided to make him one of my first sissy’s I’ve ever trained.
First, had him kneel before me. I used the “I’m gonna tell mom” line to make him do as I pleased for the time I had him. Had him lick the folds of my flower garden. Just to make sure those seed he was gonna plant had a moist place to go.
Once I had my mind rocked by his tongue, I decided that I really wanted his ass after that. Of course he protested because it was “gay” to take one in the ass. However I reminded him about the fact that he was my bitch femboy sissy now. And would learn to like it.
So, don the strap on I did.
Took him a bit to get used to having a 10 inch silicon fuck stick in his cock holster of a sissy hole. However, he began to rock back into it. And I know he had the tip of my rubber dick just rubbing up against his anal bead.
He blew his load everywhere. All over himself and the sheets. Had him clean up that mess with his sissy mouth as he’s gonna get used to taking cum like that.
However, he does get to wear my good lingerie now. Such a good sissy
Diana
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