Sissy’s Sinful Initiation

Mistress phone sex

 

My new sissy boy was eager to please, and I, his mistress, was ready to mold him into the perfect little slut. But first, he needed some thorough training.

I had him meet me in the seediest part of town, an alley known for its seedy reputation. Perfect for some kinky, public play.

As he entered, nervous and unsure, I pushed him up against the wall and asserted my dominance. “You’re mine now, sissy,” I purred, grinding my crotch against his face.I made him strip, enjoying his shy attempts at undressing. Once he stood before me naked, I examining his body, noting his softness.

“Kneel,” I commanded, and he obeyed, his knees hitting the ground with a thud. Good.

I began with some oral training. “Lick my cunt, sissy,” I ordered, spreading my legs. He obliged, his tongue trembling as it circled my moist lips. I moaned in delight, guiding his head with my hands.Then, I wanted to test his limits, so I grabbed a dildo from my bag of tricks. Sissy boys should know how to take it like a man—or better.

I pressed the toy against his virgin ass, and he squirmed, letting out a high-pitched whine. “Take it, my pretty little sissy,” I encouraged, slowly thrusting the dildo in and out, stretching him.

I revealed my strap-on, a monster of a cock that would test his limits. And oh, did he struggle as I mounted him, but I rode him hard, showing him the ways of true submission.Sissy soon learned to take my whole length, and I rewarded him with a lesson in sensitivity—a slap across his face for his efforts.

“You’re doing well, my little whore,” I praised, as he sobbed and moaned, his makeup running down his cheeks.

This sissy had potential. And so, I continued his training, whipping out my collection of toys and fantasies—his limits would be pushed, and his soul would be mine.

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