Boi Stories

663 results
Orientation
Length
Source
Infinite Scroll

The Ventriloquist

by justincbenedict on Sep 16, 2017
Humor & Satire

THE VENTRILOQUIST (Or, "Which one's the Dummy?") Okay, like, I don't know why it happened, but it was fuckin' weird, man. I was sitting in the lounge of Texas Tommy's Boi-Toi Ranch, when they got an outcall for a "Big strong, hustler". As Mickie at the desk said, they wanted the biggest boy there, ALL OVER. Next to "Detroit Half-Smoke" Willard, who's...

The Farm Ch. 03

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Ed took his time with me. He constantly taunted the two younger men as they waited eagerly for their turn to stuff their hard cocks into my cum filled sissy cunt. "Only right that your daddy gave his bitch to a real man before you two pathetic losers." After smothering me with his fat sweaty gut and smelly cock Ed had swapped ends never letting go of his pri...

The Making of an Angel Pt. 03

by AngelLawrence on Jul 31, 2019
Transgender & Crossdressers

The making of an Angel part 3. All persons are over the age of 18. *** On the drive home a myriad of thoughts were tumbling through my mind. I'm not gay but I could smell the stranger's cum on my breath and feel my panties teasing my puckered tight little hole. I was aware of my suspender clasps digging into my thighs and the feeling of the sheer nylons o...

Abducted and Turned Out Ch. 06

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

.... As I sucked the cock hungrily, I found myself fingering my kunt furiously, wishing I was being fucked by the beautiful cock I was sucking. I worked his dick over with my tongue stud on the underside, swallowing him whole and then backing off. I heard him moan and he said,"Come on slut, take it." I concentrated on the head and the area underneath and be...

Sissy Wants Her Wife's Boyfriend Ch. 03

by SissyArlene on Oct 31, 2018
Transgender & Crossdressers

I was elated as I entered the hall bathroom to freshen up. Cindy, my wife, had just invited me to sleep in the master bedroom. It would be the first time since Ty, her boyfriend, took my place in our marital bed. I didn't know what was about to happen, but I knew that I intended to take advantage of the situation. I figured I was either going to have "lesb...

My Girlfriend's Sissy Roommate Ch. 03

by SEVERUSMAX on Sep 16, 2017
Transsexuals & Crossdressers

I had to admit to myself that Larissa had never looked as sexy and drop-dead gorgeous as she did right then, bent over as I fucked her from behind and she took me deeper inside her twat. I fucked my new girlfriend so hard that she moaned and pushed back at Rain and me. He could feel the force of her hips and ass as she bumped her crack against his tongue. I...

The Making of an Angel Pt. 06

by AngelLawrence on Sep 24, 2019
Transgender & Crossdressers

The wait for Wednesday dragged... I'd gone clothes shopping and had decided on a red silk blouse with an above the knee pencil skirt with my black patent shoes and barely black stockings. I'd decided to go with my bob wig and full 90s style make up. I was looking forwards to seeing the final look and to tasting Zoe's delicious cock! I headed over to Zoe's...

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...