Cross Dressing Stories

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Halloween Cross-Dressing Bash Ch. 02

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman...

Hot Sex Instead of Dancing Ch. 14

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Tiffany discovers that her next door neighbor, Walter, is a cross dresser. "Walter?" Walter heard a voice that he immediately recognized. Cringing at the sound of her voice when he usually rejoiced at the sound of her voice, he was already turning a bright red in anticipation of her seeing him and him seeing her...

Summertime Cross Dresser Confession

by andtheend on Sep 14, 2017
Transsexuals & Crossdressers

After a long time coming, a lifetime of suffering, the first day of summer is when an aging cross dresser finally gives into the life he's always wanted to live. As if a new beginning, as if being born again, Donald looked to his transformation from man to woman, as his emergence from moth to butterfly. He couldn't wait to fly away to start his life anew. P...

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

Silky Stockings

by dirtyjoe69 on Sep 16, 2017
Transsexuals & Crossdressers

I can't remember the first time I put them on but I have come to love the feeling of silky stockings as I pull them up my long legs. It doesn't stop there either. After I first started wearing ladies stockings I took it even further. I know love wearing bras and panties as well. I just love how soft they feel on my body. My cock always responds in full forc...

Benns Feminisierung

by Racsomann on Apr 6, 2020
Amateur

So richtig Lust hatte Benn nicht auf den Geburtstag seiner besten Freundin. Sonnst waren nur Mädchen eingeladen. Aber er mochte Lisa, also ging der 18 Jährige am Freitagabend auf die Übernachtungsparty.What's next? Die Charaktere Aller Anfang ist Schwer What's next? Die Charaktere Aller Anfang ist Schwer...

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Lisa, A Story From A Male Admirer

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on the truth and real people. It all started in a routine sort of a way. Well, routine in a Literotica sort of way really! Let me explain. I am a lifetime fetishist. Male, 63, heavy build and hairy to gorilla standard. I experimented at an early age with wet clothing and kept at that converting to female attire through two marriages, tw...

Black Mistresses For Black Sissy

by Samuelx on Aug 18, 2017
Fetish

A lot of Black women in the world of BDSM consider themselves dominant, which is fine, but they seem to cater exclusively to White male submissive types. I take my clients anyway they come, since I am a professional dominatrix. I do enjoy playing with Black men, though. Unlike White subs, the brothers always make you work for it. My name is Shana Drummond an...

Chrysalis of Kirsten Ch. 01

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

The mob boss blowup doll

by Carterdruzba on Dec 23, 2020
BDSM

I was different from people I had long messy brown hair slim waist feminine type body circlet lips small dick set of thighs and thick plump bottom that jiggles I was curvy than a boy my dad didn’t pay mistress stone a strong ebony woman that leads underworld in New York she been looking for my dad for weeks plus my mom cursed when she died which her stuff th...

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