Fantaseeboy Stories

46 results
Orientation
Length
Source
Infinite Scroll

And Kerry Makes Three

by fantaseeboy on Apr 8, 2019
Fetish

When Tammy first approached me and asked me out to dinner, I nearly fainted. No one had ever asked me out before. I'm not really the sort of boy who attracts the attention of the opposite sex. At twenty years old, I stand 5'4" and weigh just over 120lbs. Everything about me is small. I've been told I have a baby face with big blue eyes and a little button no...

Thrift Store Encounter

by fantaseeboy on Mar 12, 2019
Transgender & Crossdressers

For several weeks, I'd stopped into the upscale thrift shop at different times on Saturdays and Mondays, my days off. I was trying to discover when the store was the least busy. Once the research was complete, I stepped into the store on Monday morning at 10:00 am. Aside from the familiar heavy set, middle-aged lady behind the counter, I was the only person...

Stood Up

by fantaseeboy on Jul 14, 2020
Fetish

While out to dinner with my mother, I kept getting distracted by a woman sitting at a nearby table working her way through a bottle of wine. She was sitting all alone, hadn't ordered any food, and kept glancing between her phone and the door. The woman was near my mother's age, rather full-figured with a very large bust. Her face was plump and pretty. But at...

A Rainy Day

by fantaseeboy on Mar 11, 2019
Fetish

After the absolute worst day, I found myself waiting for a bus under a shelter in the pouring rain. Out of nowhere, a truck zoomed-by and a wall of water rose up from the street and soaked me from head to toe. I stood there on the verge of tears. It was a perfectly miserable ending to a perfectly miserable day. Above the noise of the traffic and the falling...

A Maid in the Making

by fantaseeboy on Feb 12, 2019
Fetish

Mother had always been a work-a-holic. She traveled a minimum of 3 weeks each month and would often leave for 2 or more weeks straight. The day before I began my freshman year at a local community college, she left to open an office for her company on the opposite side of the planet. It was St. Patrick's Day before I saw her again. She left again a few weeks...

Aunt Pamela and Leslie Ch. 02

by fantaseeboy on Jun 25, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** The days passed incredibly slowly after my meeting with Aunt Pamela. She dominated my dreams and fantasies. She often crossed my mind while in class and I would wind up with an erection and squirming in my seat with the memory of the spanking she'd given me and the reward I'd earn...

Little Mr. Casey Applegate

by fantaseeboy on Dec 2, 2019
Fetish

One evening, I had agreed to join a large group of friends for dinner at a local restaurant. One of my friends brought along a woman named, Ruby. I sat next to her that night and knew at first glance, we were physically complete opposites. She was a decade older than me, very tall with long, straight dark hair pulled back in a huge ponytail. She was extremel...

Remi's Story

by fantaseeboy on Oct 21, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** There was only one other car in the parking lot when I arrived for my appointment. As usual, the office lights were on, but the large glass doors were locked. While bouncing on my toes, I gingerly tapped on the door and waited impatiently. I didn't wait long, from down a hallway,...

And Kerry Makes Three Pt. 02

by fantaseeboy on Aug 12, 2019
Fetish

After discovering how quickly Kerry and I fell for each other, Tammy began arranging for the three of us to spend our weekends together. She would pick us up at our respective apartments on Friday afternoon and drive all three of us to her home in the suburbs. We were together from Friday afternoon until Sunday evening. Being dropped off at my tiny apartment...

Wild Night for a Young Man

by fantaseeboy on Jun 24, 2019
Exhibitionist & Voyeur

Sitting in Samantha's car outside of the theater, my entire body shuddered when she reached into the back seat and brought forth a plain white t-shirt and white flip-flops. She laid them on the seat between us, smiled wickedly and whispered, "Karter, you know what to do. Change into these things." She was right, I knew exactly what she had in mind. Without...