Sissy Hair Stories

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My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

Sissy Crissi Ch. 02

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2 -- Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and man...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

April’s Child

by 4glory6 on Sep 16, 2017
Interracial Love

"Annie, you take them children up third floor. They like to wear Miz. Irene out on the trip. And you, Toby, stop moonin' over Annie and get the ice chest goods into the house and in the ice box. You got ice in the ice box didn't you?" "Yes ma'am," Toby answered as he trotted out the kitchen door and down to the Buick car in the drive below. "And you, Miz....

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

The Snow Sissy Ch. 01

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

Somewhere, in the frozen northern regions of our great globe, in the shivering mountains, there is a school of demon. Now, we all know what demons look like – they are creatures of immense, horrifying beauty. Even with their skin (which can range from Jet black, through fiery red, to the purest alabaster white) they possess inhuman and powerfully seductive b...

The Descent Ch. 02 - A Slow Glide

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

I sat up, the dried remnants of last night's orgasm sticking uncomfortably to my body. I looked down at my...clitty, I reminded myself. My clitty. To something akin to horror I felt the familiar lurch in the organ, and the equally familiar sensation of tightening in my balls. My clitty rose, slowly at first, but soon to its fullest extent. It began to pulse,...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...