Dressing Stories

Sam walked into the house, checking from room to room to make sure no one was home. Today was the day. Today he would finally act out on his fantasies. The idea of cross dressing turned him on. To be 'sexy'. He was only sexually interested in women, but the idea of being sexy like a woman turned him on.  After he was sure no one was home, he went up to the bathroom with his goody bag. In it were all the things he needed....

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and fuck me shoes. I wore his favorite...

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend.I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends.I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me before having sex with me. He made it clea...

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow" my sister's clothes and had a...

"Does it feel good when I do this?" Vanessa asked, briefly clenching her pussy muscles around my cock as she pumped up and down on it. "It feels like your pussy is wanking me off," I cried. "My pussy is wanking you off and sucking you off and fucking you all at the same time. Isn't she a naughty, clever little pussy," she explained, her voice quavering and breaking in the ecstacy of the fuck. I grasped the cheeks of her b...

“That’s it, already?”You had turned your head to the side and then face back into the pillow.“My hands are starting to cramp up a bit, dear.”A special, playful emphasis on that last word.Damn, that I was simply viewing the most gorgeous woman on earth was my thought as I looked at your tanned body, prone on our hotel bed. I adored giving you those full body massages that you enjoyed, the effect producing sometimes total r...

I watched Sally wiggle her skirt to the floor. She had already removed her top to expose a cute black bra. I was treated to a nice view of her decolletage as she bent over to push down her skirt. My cock began to harden in my jeans as I examined how the pale skin of her breasts met the top of her bra. Her covered breasts hung and jiggled enticingly as she bent over. I shifted my stance as my groin started to become tight...