Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

Jamie Cruises a Highway Rest Stop

by jr0777 on Sep 16, 2017
Transsexuals & Crossdressers

Hello again! I thought I would tell you about another recent adventure as Jamie. As you may know from reading my other stories, I love to crossdress and be used by strangers. I'm very submissive and especially good at giving a wonderful blowjob (or so I have been told by men after they have unloaded their hot cum into my mouth or on my face. I love to feel t...

Maid to Order Ch. 02

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Mick had been shit unlucky. He had driven over sixty miles on the day she bought all of his girly accoutrements. He had even stayed overnight, confident that she wouldn't run into anyone that he knew while he was shopping. But, as has been said, he was shit unlucky. Of all the people in the world who happened to be in the same city, shopping in the same sho...

CD Asst. Secy. Ch. 06.2: New Piercing

by cdtycoon on Oct 6, 2020
Transgender & Crossdressers

First of all, all the characters in this story are above 18. Also, it is the second part of my last story in this series. So, enjoy and keep reading. MADE TO SUBMIT Full submission as I was made to submit; ah.. almost; let's say about 90% from the next morning. You want to know why, well... The next day, 10th January 2021, I woke at my daily time of 5 a...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

Lady In The House Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Synopsis: Michele tried to use her feminine charms on the Warden at Chelmsford Prison. He rebuked her and sent her packing back to work in the prison brothel. Now Eddie has introduced her to a powerful friend of his called Davy... Can Michele seduce Dave and persuade him to help her escape the brothel where she works as a transvestite prostitute? From Part...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

T Ladies Orgy

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

(T minus three weeks) Mike Harris called it 'The Quickening'. He had borrowed the term from the film 'The Highlander' where the quickening refers to the awakening of special powers that lay dormant in certain people until they are triggered by a significant event. Mike applied dramatic licence to the feelings that regularly overwhelmed him and called these...

It All Started... Ch. 01

by trixie38cd on Sep 18, 2017
Transsexuals & Crossdressers

It all started when my sister in-law, Kim, came over after work one day to tell me my wife was just called out of town for her job. I had planned on her being gone, anyway, and so I'd left work early to get my other wardrobe out of the attic, thinking I'd have the place to myself for a few days. I just happened to be wearing a pointy cup black 36D bra, bla...

My First Time

by sexyctcd on Sep 18, 2017
Transsexuals & Crossdressers

As the rain pelted down on the roof I sank into the warm water of the bubble bath. I couldn't believe my luck. I was all alone in the house and now the rain had given me a day off as well. Just as I lay back against the tub my phone beeped a text from my wife. She had met her mom and they were on their way to the city for the day. I stretched out my long leg...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...