Delivery Boy Stories

111,188 results
Orientation
Length
Source
Infinite Scroll

Delivery Daze

by warmAmber on Sep 13, 2017
BDSM

(For those who have read my previous stories, this is not a soft romance. That said, I hope all enjoy it.) * I eased myself down to the floor, shivering a little as my bottom hit the cold oak flooring. I put the soles of my feet together, my thighs spread wide. I slowly moved the head of an eight inch dildo into the opening of my vagina. It was as cold an...

Stray Cats Ch. 07 - Final Chapter

by Dreamweaver594 on Apr 9, 2019
Transgender & Crossdressers

This is the last chapter of a story that I first posted in 2015 on this site. It's still relevant, well most of it is. I hope you enjoy it. Oh, as a reminder, you might consider going back to read the opening chapters as much of who these characters are established there, But, as always, it's your choice. Please leave a comment when you've finished, feedba...

Her First Day of Training

by Ottawa_man37 on Sep 14, 2017
BDSM

Chapter 1 – Arrival & Preparation After a 2 hour drive from your home, you arrive at the Renaissance Hotel, downtown Toronto. You are dressed as instructed by myself: wearing 2 inch heals a skirt, and a blouse. You have not been given any other instructions regarding the rest of your attire: you wear a lace bra and silky panties, but decide not to wear any...

Delivery Man

by Pantah6000 on Dec 24, 2019
Exhibitionist & Voyeur

We had been promising ourselves a mid-winter break for years, but every time we tried to arrange one something would happen. Christmas would arrive, New Year would come around and before we knew it Spring had sprung and we were looking forward to a summer holiday on some remote island in the Mediterranean. This year was to be different, we had booked four n...

The Maid and the Pizza Guy

by hollandguy on Sep 13, 2017
Transsexuals & Crossdressers

My name is Ryan I am 33 years old. I am 6'1 #200 with auburn hair and brown eyes. I am not in the best shape anymore but I wouldn't call myself fat either. I have been cross-dressing since the age of eleven. It started with just panties but has evolved to full dress over the years. I work as an electrician and take on side jobs when I can. With the recent...

Hooker Delivery Services

by notyouraveragewriter on Feb 4, 2020
Novels and Novellas

"Drop off on the left in a quarter-mile." said the disjointed, semi-automated voice from Jordan's phone, which was secured in the dashboard-mounted holder. As a way to make some extra cash, twenty-one year old Jordan Crawford had become a driver for Food2Me, the country's most popular online food delivery service. He spent his weeknights delivering greasy,...

Ashlee, JD, the White Girl Buffet

by DrHuge on Sep 19, 2017
Interracial Love

Kelli giggled as she watched the pizza man stare. This had become her favorite game. She'd answered the door in the nude. He didn't drop their pizza, like some of the other delivery boys did when they saw her large freckled breasts jutting out at a perky angle, then glanced down at her bush of orange-red pubic hair. Kelli smiled brightly. "Oh, good," she...

Violet's Anal Training

by Powerone on Sep 25, 2017
Anal

Michael sat in the chair as she entered. Powerone had described her perfectly, long black hair, green eyes, pale skin, very small hands and fingers, DD breasts and small hips. She had a gothic look to her, the black clothes standing out dramatically to her white skin. "What am I doing here?" Violet questioned, but she already knew the answer. Powerone had o...

Her First Time

by pahwhubby on Sep 16, 2017
Exhibitionist & Voyeur

She paced back and forth, nervously awaiting his arrival. She'd done some strange things, but this had to be one of the strangest. Mom would freak, she thought to herself, peaking out the window again. Mom - hell - Dad would die! He'd be furious...then he'd die! A heart attack, no doubt, at the thought of HIS daughter doing such an indecent thing! True, she...

Working Mom Pt. 03

by roidesoleil on Sep 26, 2017
Exhibitionist & Voyeur

Lacey had completed her first task of the week by getting several men on camera checking out her ass and cameltoe at the gym. It led to some great sex, with the excitement between us growing each time Lacey did her job. Her second task of the week was a little harder and more daring. Lacey was to expose herself to a random stranger (not at the gym), and c...