crossdressingstories

Forced Feminization

I decided to ride home that afternoon with the windows down and satellite radio off. The day had a surreal feel to it and somehow, the norm didn't seem appropriate. After many years of hard work, I was retiring. I didn't plan on just sitting at home, I just wasn't sure what the next section of my life would entail. My wife, Sara, had planned something special I am sure so I was kind of in a hurry to get home, but it was a nice day so I decided take my time.

I walked in the door to meet ...

Forced to CD Part 2

The next few weeks passed slowly for Ryan. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spices and unexpected flavors.

When Ryan was so rudely 'broken-in' a few weeks before, he had no idea that Theresa had been filming the event. He was kept in bondage for a week afterwards during which time h...

Forced to CD Part 1

Ryan was a not quite famous scientist who had made his contribution and was waiting for the rest of the scientific world to decide just how important that contribution was. This meant that he had time on his hands! He had never been romantically involved -- mainly because he was a secret transvestite and he had a terrible weakness for dominant women. He was also a coward! So, instead of looking for Mistress Right he had thrown himself completely into a brilliant career and had given up on the...

Dressed As A Witch

As soon as I finished my makeup training course I was eager to apply my new skills. I knew how to do regular makeup but I could also use it for artistic works. That's why I felt there was no better occasion to test myself than on Halloween night, where both me and my friend and roommate Rita were going to dress up. Even though it was a week away and we still didn't know what we were going to dress up like.

We had been invited to a party. Many of our friends were going to be there. What ...

Sleepover Part 2

Once Lauren, my dear Michelle's younger sister, had greeted all her friends she looked at me intently. "Who are you?" she asked. Quickly my little sister Carla replied, "Uh, this is Brenda, my distant cousin." Lauren replied in turn, "I didn't know you had a cousin. You never told me about any female cousins."

The rest of my sister's friends giggled, looking at me with complicity as if asking me to stretch the joke as long as possible. The rest of my sister's friends giggled, looking at...

Sleepover Part 1

After a year of living on my own I missed my hometown and my family. Most of all I missed my little sister Carla. Unlike other siblings we always got along very well.

During my teenage years I liked to take on the role of big brother and always be there for her if she needed me. But life has to take its course and naturally I had to move out at the age of eighteen to live on the university campus. At first it took me a while to adjust to having new friends and a roommate, but you get us...

Crossdressing in The Winter

This stories is written a little different than the normal stories I write. Let me know what you think of this new style.

We were hurried off the long range transport, our bags were unloaded, or should I say thrown off, and it was back into the Antarctic sky only minutes later, the first dark tentacles of the incoming storm chasing it. There would be no way out of here for five dark months.

I grabbed my two plain travel bags and followed my colleagues into the snowmobile and we pa...

Jason's Training

Jason was an average young man. He was a little shorter compared to many of his friends at school; but other than that he was average height. He was thin, he wasn't very muscular but he did have a somewhat toned body. Jason had short/medium length brown hair that he styled into a sweeping fringe, he wore it a bit messy but it pulled off the desired look.

Jason lived with his mother and older sister Lauren, who was one year older than Jason, in a small 4 bedroom house. Jason was just fin...

Forced to wear a bikini

This story happened a few summers ago. The weather had just gotten warm and everyone was out at the beach. I had never been a big beach guy, but I decided that I would make an effort to go out more. I worked at a real estate office and had become friends with many of my coworkers over the last few months. There was a girl named Cindy that I had particularly connected with. She and I had similar upbringings and faced many of the same struggles in life. She had a tall and athletic build. She al...

Crossdressed and Fucked by Another Student

Ryan was at the top of his class. He was considered by many to be the brightest person at his college. He was smart, one of the smartest. His longtime crush and academic rival was Deva. They've been competing since elementary, always trying to top each other in grades. Now in freshman year of collegel, Ryan and Deva were both invited to a Halloween party, and Ryan couldn't pass up the chance to outdo his rival and possibly make a great experience out of it too. Ryan made a bet with Deva that ...

Girlfriend wanted to try something new

My girlfriend Amber was one of the hottest girls I had ever seen. I couldn’t believe that she chose me as her boyfriend. We had been dating a few months at this point and everything was going well. We were a pretty normal couple and did many typical cute couple things. Everything changed one night when Amber said she wanted to try something new. I usually was the dominant one in bed and would do most of the work. Both Amber and I liked it that way so I was surprised when Amber said she want...

Forced to Crossdress, Tied Up, Fucked

Brittany and I had been friends since late college. She was tall, strong, and desired by many guys. I had befriended her in my computer science classes and had helped her cheat on the exams. In exchange, she would get me into exclusive frat parties. We had maintained a good relationship after college and happened to both be working in New York. She was working as a software engineer at Amazon and I was working as a data analyst at a small finance company. I hadn’t heard from her since I mov...