Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

Penny's Promiscuity Ch. 13: Freedom

by JennyGently on Sep 26, 2017
Loving Wives

My second day of freedom started a little more promisingly than the first, but only a little. I had enjoyed more sleep than the night before: the cold had woken me only once, forcing me to slide under the duvet and I had passed the night in relative calm. But as the alarm clock beeped alongside my head and I opened my eyes, the reality of the situation rushe...

The Destruction of the Vlkolak Ch. 08

by lilgirlsix on Sep 25, 2017
NonHuman

While this is the last chapter of this storyline, it will be hard to understand if you haven't first read my Wolf's Pet series. Since there are so many characters and interwoven stories, it's best if read in order:Wolf's Pet, The Twins Take Over, and then Destruction of the Vlkolak.I will be taking a hiatus for a trip to the Rhine River. When I return, hopef...

The New Matilde - 11 Months Later

by Nicky1985 on Nov 26, 2019
Fetish

This is a sequel to the story "The New Matilde". 1. Friday, August 28th: Hi. It's me again, Matilde Jørgensen, schoolteacher in Copenhagen, Denmark. And 30 (thirty!) years old later this autumn. My relationship with Thomas lasted around seven months. One day at the end of April he told me that he'd fallen for another woman and that "we" were over. Hi...

Prince Gyllen Ch. 16.1

by MythMaker on Jun 24, 2019
Sci-Fi & Fantasy

Not long after midnight, Gyllen stirred awake from a deep slumber upon a stiff mattress stuffed with straw only to be met with perfect darkness and the pressure of a colossal titan keeping a tight hold around his fragile neck from behind, preventing the teenage prince from picking himself up by his own will. For one fleeting second of ignorant bliss, Gyllen...

Dirty Sex Memories

by Brittni4u on Jul 27, 2020
Mature

Dirty Love Memories Author's Note: I want to thank the talented and gorgeous Skye_sub for co-writing and editing this story with me. It is because of her this was brought to life. If you have not read her work, you really need to do so. She is an amazing writer. I love you KYT. In a much needed moment alone, Bob was sipping a beer, seated by his in-ground...

Toyboy

by Sandman2025 on Jun 8, 2020
Romance

1986, Yorkshire, England. Part one Chapter 1 It was around 11am I received the phone call that turned my life upside-down. "Edward, it's for you", my mother shouted from the hall. "A girl." Who this mystery female caller could be, I had no idea. My mother handed me the receiver with that knowing wink only a mother could give to her son. "Hello?"...

Delivery Pt. 01

by Willowifey on Oct 8, 2019
Loving Wives

Is this really a good idea? I asked myself as I started getting undressed. Everything else was ready. The door was unlocked, the trace to the living room was traced by Ron's favourite pieces of my lingerie, the letter was laying on the coffee table. Last thing to prepare was myself. I already took a long, refreshing shower. I don't usually spend too much...

Fucked: The Interview

by thereshegoes123 on Sep 14, 2020
Transgender & Crossdressers

The camera winked on, and the familiar scene of the influencer's bedroom came up on the screen. A Cheeky grin. Showtime... "Hey guys, I'm Dizzy-Dom and today, we're doing another crazy Q and A!" Dom's carefree blond hair and cherubic features radiated energy. "Today we are joined by a very special guest... Jessica Deluxe!!" Lounging in the chair next...

Baby Sister Ch. 02: HOme aloNE

by SZENSEI on Mar 3, 2020
Exhibitionist & Voyeur

Maria Blanco felt a cool breeze caress her body as she lay atop her covers. Lashes batting against an irritable bright light she rolls over to hide her face in her pillow. The draft now terrorizing her backside made her shiver dramatically. Why was her room so chilly? Groaning against the daylight forced upon her through her balcony doors she realizes they w...

The Fantasy Twist Ch. 02

by oneguy4fun on Sep 18, 2017
Transsexuals & Crossdressers

Sunday morning was a morning for sleeping in. Dan spooned Lisa's naked body. This was not typical of Dan, as he usually preferred to sleep facing away from Melissa. Melissa was happy with this change. She enjoyed the warmth of his body. She stirred under the covers, snuggling even closer to Dan. Dan broke the morning silence, whispering into Melissa ear, "L...