This college girl loves having fun with my sissies.
I remember when I had my first experience with a sissy boy. He really liked for me to treat him like shit and embarrass him horribly. He liked that he was so much older and i was just a college girl. My current sissies (two) are on multiple levels though, one more like my first one. One enjoys my forcefulness with him and me making him an “almost woman” and things including blackmail and the other just likes for me to dress him up, but no makeup.
I enjoy showing both of them off even though it mostly embarrasses the one that’s not into makeup. With him, he found that he was into dressing up in his wife’s lingerie when she was gone. He also loves toyplay with her many sex toys.
I caught him at school one day bending over and that pink thong was showing.
I took a picture before saying anything him about it. It was just that afternoon that he undresses for me in the empty classroom and I saw his thigh high stockings, panties, and corset that he hides oh so well. I took bunches of pictures and even recorded him on my phone.
For a week I threatened to tell his wife and show her every piece of evidence. That’s when my good grades got better and he offered to serve me in every way that I wanted to be served. I sent him on task shopping trips, gave him dress up tasks, and tons more. All of which include me humiliating him, and I think that’s my favorite part.
His latest task was to deep throat my strap-on while being recorded, while a butt plug was in his ass. Like I said before he likes embarrassment so his cock gets hard and he has to be to the point of pain before he allowed to cum. He loves it so much that I get a weekly allowance for training him and tasking him. Something about the older sissies and the young college girl experience.
Now my other sissy is more open to all of the sissy games and is a bit younger than the other.
I met him while shopping in the mall for some sexy night clothes and under the wig and outfit I noticed him. I really just wanted to give him clothing advice but we interacted so we moved on. We went shopping together and I showed him how to apply makeup.
Its almost like having another girlfriend but this in different which is obvious. He likes when I get a group of friends together, some girls and guys. The college girls wear strapons and they gang bang his little pussy hole and the mouth of his. He’s probably the biggest cum whore I know. It’s also great to have sissy phonesex with him. He does have a massive dick that I do rub on sometimes but I would rather explode him than to be selfish.
Of course, my sissies have many tasks just like my slaves but it is mostly at requests. Training is most of it and I so enjoy it. Would you?