feminization, chastity, and thick cock pegging for sissy bf

veggiebabyy

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#Chastity #Feminization #Pegging #Sissy #Crossdresser #Femboy #Femdom #Sissification #Sissy Slut #Strap On
134 views • Aug 13, 2026 • 12:27 Full HD
I figured Layne was due for a wardrobe upgrade, so I went shopping! No more boring sweatpants for him, I got something that would much better suit the sissy that I know he is - an ADORABLE little plaid skirt, a cute crop top, and some white thigh high socks. Of course, no sissy outfit would be complete without a nice set of thong panties, and a tight chastity cage to lock up the useless little cocklet underneath them!!

After I have him dressed, I pull out my other surprise - a fat strapon cock, perfect for stretching out slutty little holes. In no time at all, he’s bent over the arm of the couch with his ass in the air, taking just my fingers at first, til I slip my fat cock into his eager boypussy and fuck his ass hard! The hard pounding is enough to make my little sissy fall in love with my huge cock. Next I have him ride it, tiny caged cocklet leaking and bouncing, showing all the world what a happy feminized whore he is!