Femboy

I was on Grinder about 2 years ago and I got a message from a cute little twink named Thomas. We chatted for a bit and eventually traded pics. He liked the kinky things I listed in my profile and the pictures I sent him of my toys and the ways I have used them on previous partners. I liked that he was smooth and thin and had a tight looking ass. I also liked that he sent me a pic of him in a thong. It didn't take long to discover he had kept panties from one of his girlfriends and liked to wear them while he jerked off.

I invited him over to my house and offered to buy him full outfits of girl clothes and let him try any toy he wanted. He agreed eagerly. In the space of an hour I had him confessing his crossdressing fantasies and agreeing to let me tie him up.

That Saturday I cleared my whole day and by god it was worth it. Like a lot of my younger partners and to be honest, like I was at his age he was eager to try everything at once. All the porn and unrealized fantasies were nearly enough to make him explode now that he was at the cusp of finally trying it all. I collared him soon after he arrived, it was thick and made of black leather with a ring for a leash. I pulled it tight around his neck so that he would feel it non-stop. I then jerked him off so that I could get the chastity cage on him. He was very, very submissive after that. I gave him time to try on the outfits and decide which one he liked best. He looked so cute in the french maid outfit I bought him, I couldn't help but fuck him in it. He honestly looked like a girl, and when I started licking his clean shaven hole he started moaning as if he was a girl whose pussy I was eating.

I got my cute little femboy maid hot and bothered with my tongue until he was dripping again and desperate to get fucked. That's when I stopped, put a leash on him and led him to my play room. I tied his arms behind his back and made him suck me on his knees. He was pretty inexperienced at it but I took my time and taught him how to suck a man the proper way. He was drenched in his own spit by the end and he was able to take a little of me into his throat. It was pretty hot. I then hooked his ropes into the anchor point I have on the wall before pulling out my toys. I put a prostate vibrator in his ass and played with the settings while he squirmed against the ropes. He didn't cum but he was leaking a steady steam of cum from his cage after a while and all I got from him were moans and screams. Finally I took the vibrator out and laid him on the bed before sliding into his hole. It was tighter than I had expected, one of the tightest I have ever had. He screamed and it occurred to me he'd look even cuter with a ballgag in his mouth. It turned out he did, a lot. Then I repositioned myself and grabbed his hair before breeding his tight little hole. I told him dirty things about breeding him and putting a baby in him and that seemed to only turn him on more. I came deep inside of him and filled his cute little ass up.

That was the first of many times I bred that cute little femboy maid that day, he lasted several more rounds before he had to stop because he couldn't take it anymore. I put his clothes in a box and he left looking like his normal self even if he was exhausted. I invited him to come back the next time he wanted to live out those fantasies. He took me up on that offer.