Sissy Baby Stories

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Sissyhood of Travelling Panties Ch. 01

by daddyslittlebitch on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1: Alex A pair of red satin panties lay on the bed. They were boyshort style with little red lace bows above the crotch. Very sexy and very slutty. Helen ran her fingers along the soft, smooth material. She was dressed in a black lace garter belt holding up thigh high stockings, her large, round breasts, still firm at the age of 45, stood out naked...

Straight Guy Gets Some "Strange"

by nancyvasquez on Oct 15, 2017
Interracial Love

The Negro saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the air He went to the counter. "How much to go in the back?"...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Natalie Succumbs Yet Further

by natalieukcd on Sep 28, 2020
Transgender & Crossdressers

I was lying on my bed on my back with my legs dangling over the side. I had Lewis stood between my legs, gloating at me in my underwear and cock cage. He suddenly moved around the bed and undressed quickly, as i watched him behind me. I was so nervous that i did not move. "Lift your knees up Natalie and hold them up behind the knees." I did as i was told a...

Sissy Amy Loves Mummy Belinda Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

Mummy Belinda Beynon was now in complete control, as she pushed my pram down the road. I snuggled against my satin sheets and was very content. Mummy Belinda removed my dummy every five minutes, wetting it with her saliva, before putting it back into my mouth. Staring up into Mummy Belinda's pretty face, was a dream come true. She would tease me, by blowing...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

The Sissy Diaries Ch. 1

by colettegrrl on Aug 18, 2017
Fetish

This is a story about my new life, my new way of being. I wanted to share my story so I started to record my events. I figured the best place to start was, well the beginning. Here's how it all started. * * * * * I come home to find you sitting at the dining room table, laughing and drinking with a tall, dark, well-built and handsome black man. You introdu...

Creating Ginger Ch. 07

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. Hopefully you've read the previous chapters to understand the nuances of this storyline. ~~~~~~~~~~~~~~~...