Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

The Pool Boy

by alupine on Sep 12, 2017
Interracial Love

Wendy was running late; she grabbed her keys from the hook on the wall and as she opened the door, the phone rang inside the house. "Damn it," she swore, turning back around and laying her large purse on tile counter. "Hello?" she said, answering with a pleasant voice she had to force. "Hey Wendy, it's me," she heard her husband say from the other e...

The Present Ch. 02

by Rickypillow on Sep 1, 2017
Group Sex

After a nice long nap and a shower, my little sex slave, we get dressed for the evening's festivities. I am dressed in a plain black suit and tie while you are dressed like the dirty schoolgirl you are. Short green plaid skirt, white buttondown, white ankle high socks, black patent leather shoes, pigtails, white satin panties (covering your still pink, spank...

To Pee or Not to Pee

by Tall78701 on Sep 1, 2017
Humor & Satire

To Pee or Not to Pee Or When You Gotta Go, You Gotta Go. So far all my stories have been pure fiction, so I thought it was time to branch out and try my hand (no pun intended) at non-fiction. The following four short stories are completely true. Only the names have been changed to protect the peeer. Your comments, thoughts and your own stories are very wel...

After the Windfall: 'Mother'

by GreaserBob on Sep 13, 2017
BDSM

My plan is to make this the first of several stories following Walter Winthrop as explores the world of sex and himself, but I can't promise anything. I hope you enjoy it. Warning: It contains some incest role-play, but no actual incest. I looked gobsmacked, I'm sure. "You look gobsmacked," Trilby Archer said to me with a wry smile. My family's attorney...

Santa's Little Helper

by stickivicki on Sep 17, 2017
BDSM

******************************** Proofed and edited by Brootforce ******************************** It was that time of year again; time to get the suit out of mothballs and dry cleaned, Nick thought to his self. He headed up the rickety stairs toward the attic, pushing the cobwebs out of his way. He reached the door and rattled the doorknob, causing the d...

A Houseboy for Mali Ch. 04

by gmikeisbad on Sep 13, 2017
BDSM

It's been a wild few days. Right now I am finding difficult to remember just how exactly I ended up: Bathing and servicing this beautiful Thai woman. How I became naked in the bathroom except for a hand made silver traditional Thai Femdom cockring; I don't seem to be able to remove... ...contorting my member into a bubbly shiny fat stump... After doing some...

The Wild Rose

by Lovepotion69 on Sep 13, 2017
Erotic Couplings

From the first day he saw her, he knew she was the one. It was the middle of October. Fall had arrived and the trees had changed into their yellow, red and orange attire. She was standing on the porch of a small picturesque house. Like Snow White her alabaster skin glowed in the sunshine, and her delicate hands were carefully arranging a rose bush in a pot....

Train Riding

by razmatazz17 on Sep 14, 2017
Transsexuals & Crossdressers

I'm still working on part three of Muscle Mature, so stay tuned for that. For now, enjoy a sex fantasy I've had for a while. The grammar is a little bad and some spelling may be off, I'm sorry about that, I rush to write these. Depending on how this story goes I'll decide if I make more of this story. Stay weird folks! ***** I was a tourist exploring Chica...

You're Lovely...

by Emily_Jane on Sep 14, 2017
Celebrities & Fan Fiction

Disclaimer: All characters are of legal age, although one merely looks younger than he is. The grandiose French doors to David's townhouse on Oakley Street swung open, unleashing wafts of an enticingly devilish aroma brimming with debauchery and drug-induced confusion. The doorman bore no expression as he held out his hand to assist the stiletto-sporting...

My Sexy Changes Ch. 04

by TaraJaden on Sep 16, 2017
Transsexuals & Crossdressers

At this point I wasn't the same person I was when At this point I wasn't the same person I was when I first entered the home of Auntie Louise and Alex. I was a person let loose and excited! Auntie Louise straightened my dress and looked me over. "I'm going to give Alex some money and he'll take you wherever you'd like to go." she said. "Your hair looks real...