Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

My Name is Raquel Ch. 02

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. Well, at this point, I didn't know I was Raquel, just yet. I was just a thirty-something guy with a serious secret addiction to wearing and masturbating in panties. Secret that is, until my 19-year old stepdaughter caught me in the act. Now we share a panty drawer in her bedroom. We also have lots of masturbation par...

Eric's Dreams Pt. 03

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

Eric kept thinking about his sex problem. He was a crossdresser. But most gay men didn't like that. The sex, yes, but not the crossdressing. Gay men, at least most gay men, had no interest in lipstick and lingerie, and the thrill of passing as a woman. They wanted to fuck and be fucked by men. They wanted to have their cocks sucked by men. And they wanted to...

Sissy in The Hart of the Valley

by EvelynT on Sep 16, 2017
Transsexuals & Crossdressers

The story so far; having completed the first date with Harold Plumrose and with over a month until the scheduled second date Sissy Betty Blane spends time at a t-girl club with Cindy. ***** When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persever...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

Jessica Ch. 01

by jac0879 on Mar 18, 2020
Transgender & Crossdressers

It was a familiar ritual by now. I plugged the drain of the tub and turned on the faucet to draw a hot bath. It was really a pain keeping my body hair tamed, it grew in dark and quickly but I was determined. As the water ascended in the basin, I stripped my clothes, stood in front of the sink and grabbed a razor. I quickly dispensed of every last trace of st...

Man in the Mask

by MiOtroYo on Sep 16, 2017
Transsexuals & Crossdressers

Mel was sitting on the corner of the cheap hotel king-size bed. Aroused, nervous, simply scared by the whole story, he still wanted it to happen. Once a lifetime dream, now a striking reality -- it was all here, from the remote sound of the cars passing by to that filthy, nasty smell of the motel building... "Hi, my name is Melinda. I am a young closet cros...