Crossdressed Stories

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Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Teen Boy Becomes a Girl for his BFF

by SissyKelly on Nov 23, 2017
Transsexuals & Crossdressers

Okay so this is the story of the first time I revealed my identity to someone I knew, this ended up being quite an important relationship in Kelly's life, so more stories from this will come! Names have been changed to protect the identities of everyone!! Let me know what you think and if you want to know mor stories from my life :) So Ryan went to my schoo...

Cabin in the Woods

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah... Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a...

Greg Tries a New Angle Ch. 01

by kjherts on Sep 15, 2017
Transsexuals & Crossdressers

It felt like I had flushed $199 down the toilet. For almost five months, I had been a paid member of an adult matchmaking site. Yet so far, I had only one meeting to show for it. When I divorced my wife six months ago, I promised myself that I would no longer suppress my bisexuality. Cocks of all shapes and sizes danced in my dreams those first few months...

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...

Polish Maid

by johnnysdirtysecret on Sep 19, 2017
Transsexuals & Crossdressers

'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, low cut with a short skirt, white apron, stockings and heels. M...

Made Up

by ChewToySub on Sep 15, 2017
Transsexuals & Crossdressers

My first story on Literotica! Hope you like x ***** For the longest time, I've crossdressed alone. I taught myself how to climb into girly clothes, how to roll on tights without tearing them, how to put on my wig without it looking like roadkill. It took time, but I slowly learned how to get myself ready to enter girl mode. But there's a few things I've ne...

Lady In The House Ch. 17

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Michele spotted the prospect in the mess hall. He was young, slim and effeminate and was in the company of Danny McGregor, a well know prison bully and pederast Michele was now firmly ensconced as the Madame of the Chelmsford Prison transvestite brothel which operated with impunity in E Wing of the old prison. She and Steve had had their differences, in fa...

The Roommate Pt. 13 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Lori left the bed before Leigh Ann woke up from her nap, and Lori again wished she wasn't wearing chastity. If only she could defeat it like before! But having to laboriously dial through 999 combinations on the tiny lock didn't appeal to her (although a hacksaw would probably do the job in a crude way). And so, still horny after the session with her new r...

A Favor for My Best Friend Ch. 02

by Verysecret93 on Sep 12, 2017
Transsexuals & Crossdressers

He put a firm hand on my back and bent me over the counter sink and he spread my legs open and took me from behind. What I had thought would be only a one time thing had turned into an almost daily fuck, except it was Michael doing all the fucking. He grabbed my waist as his cock slid in an out of my hole (which was no longer virgin tight thanks to him) I...