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Stories by James19999

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Series: ExpandedSeries: Combined
Meeting His Match

A ladies' man becomes a lady for a night.

by James19999
Transgender & Crossdressers 01/14/2025
H 4.74 36.6k 103 22 90
Baiting the Hook

A crafty femboy finds a way to make his fantasy come true.

by James19999
Transgender & Crossdressers 12/01/2024
H 4.81 20.2k 82 12 72
Forbidden Fruit is Sweeter

A young man is secretly feminized by his sister's friend.

by James19999
Transgender & Crossdressers 09/07/2024
H 4.75 104.2k 281 36 258
Left to Their Own Devices

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

by James19999
Transgender & Crossdressers 03/23/2024
H 4.79 71.4k 236 20 224
Shown Up

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

by James19999
Transgender & Crossdressers 01/02/2024
H 4.76 87.7k 199 18 189
The Femboy and the Tomboy

A shy college student meets the girl of his dreams.

by James19999
Transgender & Crossdressers 01/02/2023
H 4.71 84k 275 31 235
Soft and Hard

Chris gets more than he bargained for at the gym.

by James19999
Transgender & Crossdressers 09/04/2022
H 4.66 68.2k 154 19 155
A Night Out

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

by James19999
Transgender & Crossdressers 04/26/2022
H 4.73 71.8k 157 13 122
Summer Reunion

An encounter with an old classmate takes an unexpected turn.

by James19999
Transgender & Crossdressers 12/15/2021
H 4.67 54.6k 111 13 99
Study Group Surprise 2 Parts
by James19999
Transgender & Crossdressers06/10/2023
154.6k 334 43 247
1
Study Group Surprise

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

by James19999
Transgender & Crossdressers 09/14/2021
H 4.71 95.7k 203 22 190
2
Study Group Surprise Pt. 02

James embraces being a femboy.

by James19999
Transgender & Crossdressers 11/30/2021
H 4.78 58.8k 131 21 57