"I take extreme measures in an attempt to win a game with a friend."
The Set UpNot that long ago I was out for lunch with a friend of mine, Ana. She and I had bonded quickly, and had become closer friends than anyone else we knew. We were both very promiscuous and would...
"Trying on her lingerie leads to punishment"
My ex-wife was on another date. We were still living together after the divorce, locked into a long term mortgage we couldn't get out of. It was getting awkward sharing our tiny two-bedroom apartment. She had complained about our marriage for a long time,...
It begins...Well, I found out that Anne fucked that professor again. She came to my dorm, drunk at 3 am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won’t even get...
"A closet crossdresser gets caught and has the time of her life."
Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought...
"A jealous sissy finds her revenge"
My wife Cindy had a sexual past before we met. I'd only been with a couple of girls before her but her sexual history was epic. I overheard her talking about me to one of her friends once and she said...
"I was horny and just needed to make sure he still wanted me."
In the aftermath of our first paid sexual encounter, I lay bent over the desk with my ass pleasantly sore and leaking cum down my stocking covered legs. Randy had left moments after pulling out of me, but I stayed...
"Randy wanted to pay me cash for sex, but I had a counter-offer."
It had been about a month since the night that Randy had forced his way into my life. Since his office was upstairs from my business we saw a lot of each other, but he never mentioned that night until...
"Lucy gives Danni the best orgasm of his life... as a girl."
Back at Lucy’s room, Dan put down the dainty bags of lingerie and girly clothes that she had bought for him. He had been totally and magically transformed into a girl for nearly a whole day now, and every moment...
"A young transvestite tries to navigate the challenges of a real life relationship with a man"
I was on personal display for him. He would have me walk sensually while emulating the grace of a pretty blonde haired runway model. In my role of girlish temptress, I wiggle my sexy bottom in my exotic, six inch...
"Crossdresser Steve/Steffie is blackmailed by coworkers into servicing their cocks."
Steve, or Steffie, was fearful of delaying too long in the bathroom, so, shaking his head, he picked up the panties and pantyhose left on the counter for him. He discovered that the pantyhose were crotchless, and considered putting them...
