Crossdressing Stories

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Crossdressing Playdate at the Lake

by montrealjane on Sep 16, 2017
Transsexuals & Crossdressers

At the end of the summer, I was lucky enough to have some playtime at the lake. I had been emailing and IM'ing back and forward with a girl that I had found on Craigslist. Craigslist is something of a lottery full of timewasters and scary people using many bogus identities, so it takes some time to filter out who really serious to get together and have fun,...

Crossdressing For My Boyfriend

by dmk241 on Sep 12, 2017
Transsexuals & Crossdressers

My name is Chris and I'm a 25 year old, white, bisexual male. I stand 5'9" and weigh 135 pounds with light brown hair and brown eyes. I've always had somewhat of a feminine body and I've always enjoyed being a "bottom" when with other men. I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of m...

Crossdressing Friends

by kinkyrubber on Sep 12, 2017
Transsexuals & Crossdressers

In the three years that I have lived in an apartment with my friend Joe, I've never thought of him in a sexual way. Recently, I discovered that he is a crossdresser like me. We both just hide it. I was looking in his room for one of my dvd's he borrowed and found wigs, women's clothes and even a Polaroid of him dressed as a woman. The moment my eyes glanced...

Crossdressing Cum Sluts Pt. 01

by rubystartina on Sep 12, 2017
Transsexuals & Crossdressers

Although I wish it was real, the following story is totally fantasy. Thanks to everyone that helped me edit and format my story. This is my first attempt. ***** It was late in the afternoon when I finally rode up to the Radisson Hotel. You had asked me to meet you there. I thought it was a little odd that you didn't want to ride up on my motorcycle with...

Crossdressing Cum Sluts Pt. 02

by rubystartina on Sep 12, 2017
Transsexuals & Crossdressers

Although I wish it was real, the following story is totally fantasy. Thanks to everyone that helped me edit and format my story. This is my first attempt. Sorry for the long delay getting to part 2. I've been having computer problems. Hint - you need to read Pt1 to get caught up... So where were we... Oh yes.. As we finally enter the room you say t...

Crossdressing at the Girls' Academy

by TiefBlau on Sep 19, 2017
Transsexuals & Crossdressers

How do I start the story of my transformation, from a young punk to a cock-hungry whore? I guess it begins with the summer of senior year of high school, a night I still look back to with shame. Those were dark times, when I was mostly a bundle of hormones and vanity. Still, I guess I need to start from the beginning. Looking back on the night, I never shou...

Crossdressing Dad Takes on San Fran

by vikkihawe000 on Dec 24, 2019
Transgender & Crossdressers

*A bit different than my other stories, but shares some similarities. Let me know what you think. xx Vi ***** Kelly sat in a parked car in the San Fransisco Airport parking lot waiting for her father, Rod, to emerge from the terminal. Kelly loved her father and was glad he was visiting all the way from England, but she was not looking forward to him spendi...

Crossdressing Days 01: Teachers' Day

by cdtycoon on Mar 3, 2020
Transgender & Crossdressers

All the characters in this story are all above 18 years of age. Also, it is my first story as a writer as well as from the series in which I have cross-dressed in saree during my high school. ---------------It all began with an announcement for the upcoming Teacher's Day. Every year, in India 5th September; which was due in a week, is celebrated as Teacher'...

Crossdressing Days 03: Sendoff Day

by cdtycoon on Mar 17, 2020
Transgender & Crossdressers

First, all the characters in this story are above 18. Second, it is the third story in this series as well as where the first one was mild and the second one was medium, this will be the hot one, at least from my perspective and I hope you will also think the same, thank you and enjoy the story. ---------------- Before going to the actual day, let me tell...

Crossdressing Days 02: Annual Day

by cdtycoon on Mar 17, 2020
Transgender & Crossdressers

All the characters in this story are above 18 years of age. Also, this is the second story from the series, so for better grasping, you may like to read the earlier one first, but anyway it is an independent story so let us start with it. ---------------- Again it all begins with an announcement for annual day drama or dance participation, which was due in...