Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

The Adventures of Sissy Madison Ch. 02

by sissymadison on Mar 6, 2018
Transsexuals & Crossdressers

They all got into Kim's car ready for the trip. Haley turned around as soon as Kim started the engine looking Madison up and down. "You are just sooo cute, I can't even get over it!" and with that Haley got out and hopped into the back seat with Madison. "So do you like being all dressed up like this?" Kent nodded but didn't say a word. "Oh don't be l...

The Theater Pt. 01

by Stephisissycd on Sep 15, 2017
Group Sex

About a mile from my apartment is a porno theater. It plays hardcore porn films and is as seedy as it gets. Most of the people there are black and Latin men. I'm a petite white guy who has recently started to crossdress. Something about wearing slutty girls clothes makes me really horny. I'd drive past that theater and imagine walking in dressed like a tot...

The Truth

by MoistVonLipwig on Feb 2, 2021
Fetish

Beth entered the room as quietly as she could, conscious that she was running late. These kind of things never start on time, she thought to herself as she slipped into the dimly lit meeting room. Apparently this one did as her eyes adapted to the dark. She saw a couple of free seats at the back and made her way to the round table to try and catch her breath...

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Whores And Pimps Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serio...

The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

Inaugural Crossdress Sexfight

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

Hi everyone and welcome to the Crossdressers Sexfight League (CSL). My name is Dani and I'm the primary author as well as a regular participant in the league. The league title says it all. It's an erotic sexfight wrestling league for crossdressers of all ages where the loser is forced to service the winner of each match. It takes place in living rooms, bedr...

Young Crossdress, Meets His Daddy

by Sliver02 on Sep 1, 2017
Transsexuals & Crossdressers

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not k...

Secret Lives Pt. 03

by WildDaisy85 on Jun 19, 2018
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 2. I highly suggest reading the previous chapters as they set the stage for this part. This part is more of a development chapter and some readers may find it lacking in the sex department, but I feel it is important to the overall tone of the series. I appreciate the feedback and please keep it coming. I am also lo...

That's What Friends Are For Ch. 03

by TurningintoCD on Sep 15, 2017
Transsexuals & Crossdressers

I didn't know what to do about David. He was my best friend and after years of teasing me, he had opened up a pandora's box of getting me to crossdress. Now I'm supposed to go as his date, as Angelina Jolie, but the host of the party, Ben, a real gentleman, wants me too. I wish I could be Ben's date, but I don't know how to escape from David's grip. "Alliso...

The Project Pt. 01

by Chloecrownofthorns on Sep 16, 2017
Transsexuals & Crossdressers

Dee's bedroom lit with a dim blue glow from her smart phone. Her nailed finger swept up the screen as she scrolled the strictly platonic listings. "Boring, boring, spam, fake. Can anybody complete a sentence on here!?" she thought. She was just about to give up when she read the headline, "Mess around with gender roles..." As she read the post, she smirk...