The Ballad of Sissy Mike

Guess who's legs, Give up? Mine!

Another tale from my first week as a professional fetishist:

I was alerted by the dungeon manager Bella, that a gentlemen dubbed Sissy Mike would eventually session with me. "He only sessions with the new girls," she told me. "If he likes you he will see you for a few months, but he always moves on the newest girl." Sissy Mike was a cross dresser and he wanted the same role play every time. According to Bella, Mike would fill me in about everything. Then Bella and the other girls, all dungeon veterans, giggled. That was all they were going to tell me. They didn't want to ruin the surprise.

One rainy Monday night Sissy Mike wandered in and requested a session with me. He was in his 50's and wearing a powder blue tracksuit. He was uncomfortably quiet, and he was all business as he dragged me to the sissy closet. He meticulously picked out a bra, panties and stockings, and then he grabbed a flogger.

"So do you like to be flogged?" I asked.

"No," he answered.

We got to the room and Sissy Mike laid out the scenario. I was a clerk at the lingerie store and he would come in to buy some presents for his girlfriend, but I would force him to wear the lingerie himself. So that's what we did. I dressed him in women's underwear and even did his makeup. Then he picked up the flogger and dug into this track pants pocket. He pulled out a magnum condom and unrolled it on the handle of the flogger.

"Call me a bitch and make me suck this."

That was how I learned that a cross dressing man never feels like his outfit is complete unless he has a 'dick' to suck.

I timidly asked his bitch-ass to suck my dick while holding the flogger a foot away from my body. He sucked and his lipstick smeared all over his chin and the condom. The sight of a hairy middle aged man in fuchsia lipstick sucking this makeshift dildo was gruesome. I needed a productive way to channel my disgust.

I took the flogger and put it between my legs with the handle poking out from my crotch.

"I don't think you are sucking hard enough, you ugly bitch!"

Then he really went at my dick. At some point he lay back on the ground, flipped his legs over his head and jerked off onto his own face. Surprise! It's been 4 years and I still haven't seen a man, other than Sissy Mike, ejaculate on to his own face.

After he came, he turned in to the friendliest man you could ever meet. He wanted to talk about literature, movies, the weather, my childhood. Sissy Mike was a completely different person once he got his cross dressing rocks off.

Sissy Mike saw me every Monday night for the next 6 months. He always wore the same track suit. He always barely spoke until the scene was over. His session always had to be exactly the same. I must have seen him come on his own face at least 25 times. When Miss Layla got hired and replaced me as the dungeon newbie, I never sessioned with Mike again. Sometimes I would see him with a new girl in the sissy closet picking out the perfect bra. I always said "Hi Mike" even though he would never answer back.