Bully Boss Stories

42,866 results
Orientation
Length
Source
Infinite Scroll

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Step-Mother has a Secret

by call_me_dana on Feb 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "Rachel ... Wait! I can explain." The curtain had already closed and she was gone. I looked in the changing room mirror and my untucked bulge was quite evident. I hurriedly re-tucked, stepped into my leather skirt and into my heels. Looking at the pretty young woman who had been...

Amor Prohibetur Ch. 17

by CorvusTurrim777 on Dec 12, 2018
Loving Wives

Some of my stories start off as short stories, but they take on a life of their own and turn into full novels. In the Lovers From Beyond series, Vivian's Escapades was meant to be a short story, but it ended up being a full novel. Similarly, my first Heartbreakers short story turned into an entire trilogy. That's what happened here with Finding Paradise. Ori...

Becoming Taylor's Bitch

by wistan on Sep 24, 2019
Transgender & Crossdressers

Generally, my writing is quite... extreme. Non-consent, violence, magic, superpowers, even death sometimes. Literotica doesn't like that much, it seems, so this was an attempt to write something rather more conventional and consensual. I enjoyed writing it, may well continue it or do more like it at some point. Hope you like it too. All characters are aged...

A Creamy Blast from the Past

by SugarandSalt on May 7, 2019
Transgender & Crossdressers

This is a resubmission. All characters depicted are eighteen years old or over. * It was the sort of beautiful Spring day that transcends all description. The sky was crisp and clear and perfectly blue. Calvin didn't take notice of the fresh green grass crunching pleasantly beneath his feet nor the burgeoning trees, with their leaves dancing in the breeze....

As It Seems Ch. 08

by rowan3 on Sep 15, 2017
Interracial Love

Her head was still heavy from last night's wine, making it hard to open her eyes. She heard the steady thud of her pillow's heartbeat; she heard the comforting sigh of Janabelle trying to pull herself out of sleep. Alexa turned her head to see her eyes fluttering open. Each one laying their head on the opposite ends of Gauge's stomach. Each comparing their p...

Punished at St Sade's Ch. 03

by Julie20 on Sep 15, 2017
Fetish

Chapter Three Fallen Sister At 25 Sister Fortitude was not much older than the 18 year old girls at St Sade's whom she took for Gym lessons. When she was really honest with herself she had to admit to a tingle whenever she happened to go into the changing room and find herself surrounded by fresh young 18 year old girls wriggling out of wet swimming costum...

A Learning Experience Ch. 01

by Joscelyn2tg on Sep 19, 2017
Transsexuals & Crossdressers

Hello! I stumbled upon Literotica by accident one day, a few weeks after my transgender partner of 4 years, and the love of my life, died of an accidental drug overdose. Still out of my mind with grief, I found the TG stories on Literotica to be such a healing essence that I became completely enthralled by them. Because writing and editing have been an impo...

Sex And Susan Adams Ch. 03

by SteveLee1146 on Sep 14, 2017
Novels and Novellas

The following evening, Susan, wearing her nightgown under her robe, arrived to, as she said, "baby sit" with Jean. Both women had looked with great anticipation to being together for the night, but still were a bit apprehensive in what was a new situation. Still, the idea of "sleeping together" as opposed to merely sleeping in the same bed, had stimulated th...

Sex And Susan Adams Ch. 02

by SteveLee1146 on Sep 16, 2017
Novels and Novellas

As Jean closed the door behind Susan, she slowly climbed the stairs with her mind completely befuddled. On one hand she was concerned about Susan's problem, still somewhat shocked at her own violent and non-characteristic reaction to Susan's verbal attack, but, most of all, she was absolutely incredulous as she thought of her sexual arousal as she saw and fo...