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8

Stories

Stories by James19999

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Series: ExpandedSeries: Combined
Left to Their Own Devices

A shy femboy and his roommate's athletic sister experiment.

by James19999
Transgender & Crossdressers 03/23/2024

H 4.81 25k 88 14 157

Shown Up

A strong woman brings out a young man's femininity.

by James19999
Transgender & Crossdressers 01/02/2024

H 4.75 46.5k 108 13 201

The Femboy and the Tomboy

A shy college student meets the girl of his dreams.

by James19999
Transgender & Crossdressers 01/02/2023

H 4.72 56.8k 192 28 329

Soft and Hard

Chris gets more than he bargained for at the gym.

by James19999
Transgender & Crossdressers 09/04/2022

H 4.65 53.3k 124 14 232

A Night Out

A new sissy's first time with the fit MILF next door.

by James19999
Transgender & Crossdressers 04/26/2022

H 4.72 56.1k 109 11 188

Summer Reunion

An encounter with an old classmate takes an unexpected turn.

by James19999
Transgender & Crossdressers 12/15/2021

H 4.64 45.6k 94 12 171

Study Group Surprise 2 Parts
by James19999
Transgender & Crossdressers06/10/2023

123.1k 273 37 416

1
Study Group Surprise

James explores his feminine side with his crush's roommate.

by James19999
Transgender & Crossdressers 09/14/2021

H 4.73 75.2k 163 19 271

2
Study Group Surprise Pt. 02

James embraces being a femboy.

by James19999
Transgender & Crossdressers 11/30/2021

H 4.78 47.8k 110 18 145

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