How I Explored My Sissy Fantasies on the Phone

I always wanted to be humiliated by a beautiful woman. For some reason, I craved getting all dressed up and looking like a poor excuse for a sissy. If she made me be her French Maid that would be my favorite. My ideas came out of nowhere. I was very well adjusted and a successful businessman. I guess I just craved to lose total control of everything! I wasn’t sure if I was ready to explore this beauty in real life just yet so I thought I would try a kinky chat line. My hand was shaking as I dialed the number because I just didn’t know who I would encounter. I put my phone on speaker so I could wank at the same time.

“Hello,” A woman’s voice said. She sounded silky and smooth. “My name is Mistress Emily. You will obey me, or else.”

I gulped. “Yes mistress.” I whispered.

“That’s Mistress Emily to you!” She snapped.

Wow, this girl was the real deal. We talked a little about our fantasies with her questioning me as if we were in the middle of a top secret interrogation. Finally we got to the playtime. She described how she would dress me up in sissy garments, basically just an ill fitting bra, a pink thong and an assless apron. She told me how once I earned it, she would lock up my cock and put it under her control, and she would show me how she would put me to use on all her friends – male and female. This was my absolute cuckold sissy fantasy, it was like she knew exactly what to say. I couldn’t believe my ears on the sissy chat line and before long I was spewing jizz all over the place.

“Did you just cum without permission?” Mistress Emily seethed.

I just gulped.