Crossdressing Brother Stories

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Infinite Scroll

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Mistress Chantel, Tranny Dominatrix Ch. 15

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fifteen: We Meet Each Other's Parents and There Is A Wedding Ready to Go. [Sunday late morning]. "How many sissy maids have agreed to come clean for us Hun?" Kerri asks. "Three little sweetie maids Babe." I smile and reply. "They will be by on Wednesday before our Friday wedding. They are all so excited to play sissy house maids for us while t...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

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Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

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...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

The Secret Panty Handjob

by anonymouspeggy on Feb 10, 2020
Transgender & Crossdressers

I didn't have a cell phone in the nineties. Even if I did, text messaging wasn't a thing. I had an email account through my university, but plenty of people still weren't using email. And even if they were you didn't always know their account. So I had no way of communicating with Angela. I certainly couldn't call her home phone. She was my aunt's step d...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...