Fantaseeboy Stories

46 results
Orientation
Length
Source
Infinite Scroll

Spanking Discovery

by fantaseeboy on Oct 8, 2019
Fetish

This story contains descriptions of incest and homosexuality. \ *** Even before Mallorie asked me to marry her, she had become very close to my mother. The two of them became fast friends immediately after I'd introduced them. I began spending less time with Mallorie because she was spending so much time with my mother. My mother loved to share stories a...

Aunt Pamela and Leslie

by fantaseeboy on May 15, 2019
Fetish

When my Statistics class drew to an end, I raced out of the room while struggling to keep from crying. I'd never gotten anything less than an 'A' on a test. And my very first quiz in my Freshman year at University I'd bombed with a 'B'. I was devastated. As I dashed down the hallway, I passed a bulletin board and a pink slip of paper caught my eye. It was h...

Payson's Wedding

by fantaseeboy on Jun 5, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Very early on in our relationship, Becky learned how much I enjoyed anal play. While lying naked across her lap, she was giving me one of her mind-blowing handjobs when she suddenly slipped a finger between my cheeks and touched my wrinkled hole! I obviously wasn't expecting it an...

Finley and his Land-Lady

by fantaseeboy on Jun 11, 2019
Fetish

As a child, I was rather sickly. My mother knew there was something wrong with me and after dozens of appointments with doctors and countless tests, it was determined that I had a pituitary issue. My mother took me to an Endocrinologist who prescribed several different pills to correct for my damaged pituitary gland. He also put me on growth hormone and taug...

Emery and Alice

by fantaseeboy on Jan 27, 2020
Transgender & Crossdressers

When my uncle, my only living relative, passed away in his sleep from an aneurysm, I returned to settle his estate. I hadn't been in that part of the country for nearly a decade. I had been in middle school when my mother passed and I was forced to move in with my aunt on the opposite coast. My uncle had always been the oddball of my mother's family. But he...

Legal Assistant

by fantaseeboy on Jan 7, 2020
Fetish

Mrs. Swanson was a very successful attorney who specialized in the defense of women who were sexually harassed in the workplace and women who were abused by their male boyfriend or husband. I was her very first male employee. It was her plan to hire a male assistant, knowing the older woman who had long worked for her would someday retire. She had interview...

Condo Cuckold

by fantaseeboy on Sep 23, 2019
Fetish

Arriving home at 1 am after spending the evening playing video games with my friend. I parked my car outside of my condo and made my way inside to learn my roommate has had friends over again. As I was walking in, the last three of her friends were staggering out. My roommate, Samantha was nowhere in sight. I figured she was probably passed out in her bed. W...

Summer with Unkie

by fantaseeboy on Jul 16, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** When my stepmother accepted a job in Europe just after my graduation from high school, I was sent to live with her brother, my step-uncle. This wasn't a bad thing. A new city meant a new start. And I could use a fresh beginning. I was never popular at all. I hadn't had a real frie...

Payson's Wedding Ch. 02

by fantaseeboy on Jul 16, 2019
Transgender & Crossdressers

The next morning, Becky and I walked into the jewelry store a few minutes after it had opened. The older man who owned the store looked at us with a funny expression on his face. We approached him hand-in-hand. Becky, with her Hispanic heritage, was wearing jeans, a white blouse that draped over her giant breasts in the most alluring manner, and white cross...

A Rainy Day Ch. 02

by fantaseeboy on Mar 26, 2019
Fetish

My first day with Peggy had been absolutely magical. She offered the love, tenderness, and affection that had been missing from my life. After spending the evening in each other's company, we retired to her bed. We slept together that night. She wore a sensible, nylon nightgown while I remained naked. There was no sex, although I was stiff and horny througho...