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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 4.82 27.5k 92 16 167

Shown Up

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

by James19999
Transgender & Crossdressers 01/02/2024

H 4.75 47.9k 109 13 207

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 57.6k 194 28 337

Soft and Hard

Chris gets more than he bargained for at the gym.

by James19999
Transgender & Crossdressers 09/04/2022

H 4.65 53.8k 125 14 237

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 56.6k 109 11 191

Summer Reunion

An encounter with an old classmate takes an unexpected turn.

by James19999
Transgender & Crossdressers 12/15/2021

H 4.64 45.9k 94 12 171

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

124k 273 37 418

1
Study Group Surprise

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

by James19999
Transgender & Crossdressers 09/14/2021

H 4.73 75.8k 163 19 273

2
Study Group Surprise Pt. 02

James embraces being a femboy.

by James19999
Transgender & Crossdressers 11/30/2021

H 4.78 48.2k 110 18 145

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