Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

Other Side of the Coin

by NaomiQ on Sep 15, 2017
Transsexuals & Crossdressers

If this is at all popular I will continue the story. The next chapters will be much more sex driven and dirty. ***** "So, you're saying that all I have to do is imagine myself as another form?" Michael asked. "Yes, but you must concentrate deeply in order for the transformation to take place. The change can be as simple as adding a freckle or as drastic a...

What if...

by protoborg on Dec 5, 2015
Miscellaneous

You stand looking about yourself. There is nothing but white in all directions. Nothing but solid, unending white as far as the eye can see and probably further than that. There is light or there isn't. The vast whiteness of the place you find yourself in makes it very hard to tell. The only thing you can be sure of is that you are standing naked in a seemin...

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Chance Meeting on eBay of All Place

by Leighharding on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story of a chance meeting which has turned out to be really rather amazing and surprising. ***** I was trolling eBay for some underwear to buy when I happened on a rather large lady selling some used kit. I messaged her to ask specific sizes and she responded straight away asking if it was for me. Normally I would deny that I was buying...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...

I Dress Up and Fuck My Friend Pt. 01

by tgirlchrissy on Apr 3, 2019
Transgender & Crossdressers

So last summer I was left home alone for a weekend while my parents were at a wedding. I was bored so I had my friend come over. I usually crossdress and masturbate in my sisters clothes while I have an empty house. Me and my sister are about the same size but she is curvier. She is also at college so I dress whenever I want. So me and Kyle sat around and wa...

My Sexual Fantasies

by Submissive Timmy on Sep 16, 2017
Letters & Transcripts

My Sexual Fantasies (OD Repost) I wrote this in November 2002 for my online journal on Open Diary. I'm posting this simply to have something posted. I do intend to actually write eventually. ***** I have a penis. Isn't that amazing? I also have two testicles. The flu had a stranglehold on them and killed my sex drive. But, I've since driven the flu off wi...

Wedding Date

by bullockhall on Sep 13, 2017
Transsexuals & Crossdressers

It was friday night, and I was at a sports bar watching college basketball with my best friend, Alan. We'd grown up in the same suburban town and had been friends our whole lives, meeting in kindergarten, and taking the same classes through high school. We did everything together, slept over at each other's houses, double dated, and were like brothers. We...

David and Jess Ch. 04

by TGDIB on Apr 22, 2020
Transgender & Crossdressers

This story is entirely fictitious. All names and likenesses are fabricated, and all characters depicted are over the age of 18. This story is multiple pages / chapters, and involves elements of romance and erotica. ---------------- Chapter Four: I stared in disbelief for a moment, frozen in place as my mind reeled. Surely I must have misheard. Jess's hip...

She Snuck Me a Pair of Her Panties

by anonymouspeggy on Mar 2, 2020
Transgender & Crossdressers

I woke up on Christmas Eve to the sound of someone knocking on the door. It was after nine o'clock. I was in a guest room in my uncle's basement sleeping in a tee shirt and pair of silky black panties with a red floral print. Next to me was another pair of panties that were stiff with my dried cum. Angela had used them the night before to give me a handjob...

Jessica Find Her Way To "The Gym"

by DCJessicaCD on Sep 16, 2017
Transsexuals & Crossdressers

My name is Jessica and I've been a crossdress most of my life. I'm about 5'11", leggy and really cute. I've long reddish brown hair and I usually am able to fit into a size six. One time I got the chance to be alone for the weekend so I had to find a way to amuse myself... Didn't find any luck on the chatlines...so I got up enough nerve, packed my stuff (...