Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Timmy's New Job Ch. 02

by holycow614 on Sep 16, 2017
BDSM

Timmy was squeaky clean and drenched, much to his disgust, with a girly perfume. Timmy was taken to another room full of bright lights, make up, and extremely erotic lingerie. Mary unhand cuffed Timmy, then the other four girls forcibly strapped Timmy to a swivel type make up chair in front of a large mirror surrounded by lights. Puzzled, Timmy asked, "What...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

Lisa’s Evolution Pt. 02: The Crossing Over

by molotov_teacher on Oct 19, 2020
Fetish

Title: Lisa's Evolution Part II: The Crossing Over Author: Jack Riley --------------- As I pulled into the driveway of Lisa's large family house, I thought back to the previous year's unexpected encounter at our favourite conservation park. Lisa, who had been my friend and 'little sister' for years, had unexpectedly decided I would be the first boy she wo...

The Cabin Ch. 07

by MaddieKim on Sep 14, 2017
BDSM

This is the final chapter of The Cabin. The story would not have been posted without Kirk2004's editing abilities. Once again, thank you, Kirk. ~*~*~ The Kitten is curious "Admit it, Kit. You're curious. You wonder what it would be like to be tied up and fucked." "I don't..." Kit's fingers went to the scar. Oh hell, Michael thought. She had been tied u...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

Riley's Bar Ch. 08

by Just Plain Bob on Sep 15, 2017
Loving Wives

Naturally the first thing I did when I got to Riley's the next day was corner Candy and ask her about the "shame shame" sign she'd made the night before. "What do you expect when you are messing around with a married woman? Shame shame on you." "Give me a break okay? I didn't know she was married and come to think of it you didn't know either. You were the...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....