Sissy Small Penis Stories

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Orientation
Length
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Infinite Scroll

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Behavior Modification Institute Ch. 13: Final

by NancyPan on Sep 25, 2017
Fetish

Thanks to all of you who encouraged me to continue writing this story. Stay tuned for new stories. Please vote! All respectful feedback appreciated. ***** "Wake up, Nancy. Rise and shine. Time to get up, sissy." I hadn't heard the key turn in the door lock, and I hadn't heard Ms. Jensen enter my room. I sat bolt upright, then remembered that I was wearin...

The Countess and the Contest

by darkheathyr on Sep 16, 2017
Transsexuals & Crossdressers

"Heathyr." The haunting, melodic tones of the Countess' voice rang out through the cold, silent house. Even after months in her service, I still couldn't get over the way the exquisite marble floors and twelve-foot arched ceilings managed to create seemingly impossible acoustics. It was as if the entire house was built to obey her beck and call -- which prob...

Sissy College Ch. 02

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All Characters 18+. Sorry for the delay. Life gets in the way sometimes. This is a sissy/interracial themed story - if these themes offend you, or you are unable to separate fantasy from reality, please read no further. Special thanks to Puzziboi for all her input. I love hearing about the mess you make in your panties, so please do leave feedback. ~~~~~ L...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Dani's Night Out

by Jemina004 on Sep 26, 2017
Transsexuals & Crossdressers

Danielle Winona was very nervous. Maybe it was because he was standing outside the door of a strange man's house at night in a mesh top, tiny skirt and thong panties. Maybe it was because he had just rang a stranger's doorbell and he had no idea of what awaited him inside. Whatever it was, and whether he enjoyed it or not, Dani had to be as pleasing and sexy...

Lace and Love Ch. 04

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake walked back to the living and was happy to see Alice in her second position, on the knees with her arms crossed behind her back. She was waiting in front of the leather sofa chair where Jake would sit. Jake walked up behind her as he noticed all the toys laid out on the coffee table. He bends over and grabs her long black ponytail and lightly yanks her...

How Nathan became Natalie Ch. 02

by saintlycd on Nov 26, 2017
Transsexuals & Crossdressers

"Studying hard, sexy." Kevin's deep voice said as he entered our dorm room. I was lying on my bed on my stomach with an open notebook and chemistry text book in front of me. I was wearing what was my now typical "hanging around the dorm room" outfit was; tight short girl's athletic shorts, and a cropped girls tee shirt with our colleges logo and mascot on i...