Literotica
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Stories by James19999

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Series: ExpandedSeries: Combined
Forbidden Fruit is Sweeter

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

by James19999
Transgender & Crossdressers 09/07/2024
H 4.77 53.6k 164 26 305
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 51.2k 174 20 324
Shown Up

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

by James19999
Transgender & Crossdressers 01/02/2024
H 4.75 68.8k 163 16 313
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 70.9k 242 31 429
Soft and Hard

Chris gets more than he bargained for at the gym.

by James19999
Transgender & Crossdressers 09/04/2022
H 4.67 61.1k 144 17 281
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 64.1k 134 11 235
Summer Reunion

An encounter with an old classmate takes an unexpected turn.

by James19999
Transgender & Crossdressers 12/15/2021
H 4.65 50.2k 104 13 193
Study Group Surprise 2 Parts
by James19999
Transgender & Crossdressers06/10/2023
139.6k 301 41 501
1
Study Group Surprise

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

by James19999
Transgender & Crossdressers 09/14/2021
H 4.71 86k 182 21 332
2
Study Group Surprise Pt. 02

James embraces being a femboy.

by James19999
Transgender & Crossdressers 11/30/2021
H 4.78 53.6k 119 20 169
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