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Stories by James19999

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Meeting His Match

A ladies' man becomes a lady for a night.

by James19999
Transgender & Crossdressers 01/14/2025
H 4.74 35.4k 103 20 87
Baiting the Hook

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

by James19999
Transgender & Crossdressers 12/01/2024
H 4.8 19.7k 81 12 71
Forbidden Fruit is Sweeter

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

by James19999
Transgender & Crossdressers 09/07/2024
H 4.76 101.1k 278 35 255
Left to Their Own Devices

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

by James19999
Transgender & Crossdressers 03/23/2024
H 4.8 70.1k 233 20 221
Shown Up

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

by James19999
Transgender & Crossdressers 01/02/2024
H 4.75 86.4k 197 18 186
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 83.2k 276 31 236
Soft and Hard

Chris gets more than he bargained for at the gym.

by James19999
Transgender & Crossdressers 09/04/2022
H 4.66 67.8k 153 19 154
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 71.3k 157 13 121
Summer Reunion

An encounter with an old classmate takes an unexpected turn.

by James19999
Transgender & Crossdressers 12/15/2021
H 4.67 54.3k 108 13 99
Study Group Surprise 2 Parts
by James19999
Transgender & Crossdressers06/10/2023
153.6k 336 43 244
1
Study Group Surprise

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

by James19999
Transgender & Crossdressers 09/14/2021
H 4.71 95.1k 203 22 187
2
Study Group Surprise Pt. 02

James embraces being a femboy.

by James19999
Transgender & Crossdressers 11/30/2021
H 4.78 58.5k 133 21 57