Being a newly wealthy woman I decided it was time for me to take on a kinky maid. I had done a few interviews and no one really seemed to be what I was looking for. Some were just not enough and some were just too much. But, finally, a young man walked through the doors. He looked perfect and I hope he would be what I was looking for. He was on the shorter side and had a very slender body. Just by looking at him made me want to get him into forced feminization.

His name was Derek, he was 22 and in college as a music major. He was a slave and loved to be humiliated. He had never experienced forced feminization but he was willing to try it cause it excited him. So I hired him and told him to expect an email for instructions on his start date. I was so looking forward to turning him into my little sissy maid. I couldn’t kee the grin off my face as I arranged everything that would be needed.

Derek showed up for his first day of work and I took him into my home office. On my desk was a box with his uniform in it. I told him to go upstairs to the second room on the right. He was to put on his uniform and be made over for me. Like the good little sissy boy he was, he went upstairs and started the forced feminization process. I was so excited to see him as a girl!

Forced feminization is just so much fun!

As part of his training, I invited one of my close guy friends over to the house. To be a good sissy maid isn’t just about cleaning my house but also to take care of any needs I have. And right now my need was to see him get used as the sissy slut he is. I had him clean my house making it spotless. And once he was done I told him that it was time for his sissy training!

I took him to my bedroom where my friend Jack was waiting. He looked like a bronzed Adonis sitting on the edge of my bed and if the man was gay I’d fuck him myself. Derek was so nervous but I could see the excitement in his eyes. Being his first time with forced feminization and being a sissy was a huge thing, just like Jack’s cock. I had him get on his needs and service Jack however he saw fit.

Jack grabbed Derek by the hair and forced his mouth on his cock. Face fucking him and shoving it all the way into his throat. I watched as Jack fucked that sissy maid’s mouth and was loving the live show. I sat on my chaise and started to rub my pussy. Jack pulled his cock from Derek’s mouth and shoved him face-first onto the bed. Shoving the maid skirt up to his hips and pulling the panties to the side so he could thrust his hard cock inside him.

Derek was about to get used as a real sissy slut!

Jack was fucking Derek’s tight little pussy hole and I knew it was just a matter of time to turn him into a cum slut. It was so hot watching Derek lose his anal virginity. Jack fucked that pussy hard and fast. He gave Derek the fucking of a lifetime. I knew Derek was hooked already. Moaning and begging for more as he thrust back into Jack. Grabbing hold of his hips and smashing Derek into the bed as he fucked him harder.

Jack pulled out and flipped Derek over and then shoved his cock in his mouth as he blew a huge load. Derek’s first day of forced feminization and being a sissy maid was a huge success. I couldn’t wait to fuck his tight little pussy myself. But that would be for another story, wouldn’t it? Maybe you should give me a call and be my Derek? I’d love to have sissy boy phone sex with you!