Crossdressing First Time Stories

351,059 results
Orientation
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Infinite Scroll

Giving My First Blowjob

by SLMaid on Sep 16, 2017
Transsexuals & Crossdressers

After a few beers and chicken wings, I left Jim at Gunny's. As I got up to leave I handed him an envelope and told him to give me a half hour then come over to my hotel room. As I left I wondered if he would go through with this. In the envelope was a pair of black nylon full brief panties with a note that said "Put these on before you come over", Sara. Aft...

Tammy Truth and Fiction

by TammyPanty on May 9, 2018
Transsexuals & Crossdressers

One of the elements of erotic stories is they are based in most cases in fiction. But most fiction is grounded in fact. I get several pieces of feedback about my stories asking me about certain experiences I have described. Not everything in each story has actually happened, but I have personally experienced more of what I describe than what is fiction. Fir...

Mistress Mariegolds Academy

by Heinrich12345 on Dec 25, 2019
Transsexual

The Academy was founded and is still leadet by Maria Mariegold. With a lot of hard work and pasion she managed to make the Acadamy to one of the most prestigious schools in the whole Empire. Today some of the most influential Families send their kids to this fecilety to become influential Futanari or a great cocksucer for some high class Futanari. Over the l...

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Anime ENT

by akikuka on May 16, 2019
Exhibitionist & Voyeur

They always confused people around them of their true genders as their appearance and figure contrast their true physical self regardless of their claim. It doesn't help that most of them wear female clothing to further add our confusion(and our sexuality). They are called Traps, or Tomgirls if you will. Having the beauty that brings girls to shame, these tr...

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Girlboy Diary Day 01

by Hartford on Sep 16, 2017
Transsexuals & Crossdressers

Day 1 It might never have happened if my aunt hadn't caught me wearing girl clothes at the mall, clothes plus a wig and make up. How she knew it was me is a mystery because I can pass like nobody's business. Hate to brag but it's a fact. Anyway, my aunt followed me, got some still photos and video on her blackberry, and showed it to Mother. I found out six...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

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The Awakening Ch. 04

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Part Four – Michele Returns The woman is slim. She is wearing a cerise satin blouse, black leather skirt and black high-heeled pumps. Flesh-toned fully-fashioned stockings sheath her long well defined legs. She is wearing a blonde bob, her bangs direct your gaze to heavily madeup eyes, and she's wearing glistening ruby-red lipstick. She is mature but sexy...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...