"Timmy is alone for the holidays or will he."
Christmas break at the Boarding School. It was December 15th, the dorm was empty and I was alone in my room. My parents sent me away to an all-male College/Boarding School in the Northeast, USA. They suspected I was Bi...
"A perfect date for the weekend leads to more."
I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow....
"Vicky is taken to a gloryhole to enhance her oral skills."
My wife was very pleased with how I had performed as Vicky. My cross-dressing had progressed from a sexual role play with my wife to her setting me up for my first sexual experience with a man. At the same...
"Learning how to be a passable crossdresser"
So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop...
"Carlos finally takes the plunge"
Carlos sat in the car for a moment looking up at the sign of the sex shop. He had been in the shop on more than one occasion. A lubricant here and a toy there, to spice up the bedroom...
"A friend cheers me up"
It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me....
"Sam/Samantha encounters some online acquaintances in a park"
The street was still, silent, unnaturally silent for a night like this. Chloe’s perpetual gum-chewing worked in tandem with the sound of Samantha’s heels. “So where are we going?” Samantha asked.“Through here,” Chloe said.It was a narrow passageway, and at...
"Sam finds that dressing as a woman is one thing, becoming in trapped in a woman's body another"
“You coming to the party later?”“Maybe,” Sam said casually. “I haven’t decided yet.”His sister, Melinda, shrugged. “Then maybe we’ll see each other later.”“Yeah.”Sam watched as his sister turned and left the room, leaving a waft of scent behind her. He...
Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that...
"Young man lets his inner woman out during an encounter with an older man."
Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am...