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11

Stories

Stories by sissysherry2

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Series: ExpandedSeries: Combined
A Surprise Blind Date

An Innocent party turns into something more.

by sissysherry2
BDSM 07/04/2019
4.06 12.2k 3 3 9
Another Sissy Shopping Adventure

Another sissy shopping assignment from a young mistress.

by sissysherry2
BDSM 07/15/2018
3.81 27.9k 6 5 14
Sissy Shopping Adventure

A sissy heads to the mall for some pure humiliation.

by sissysherry2
Transgender & Crossdressers 05/10/2018
4.33 55.5k 26 11 41
Tables Turned at the Mall 2 Parts
by sissysherry2
BDSM06/08/2023
74.9k 32 5 58
1
Tables Turned at the Mall

A sissy gets more than she reckoned with at the mall.

by sissysherry2
BDSM 04/20/2018
4.15 47.7k 23 3 44
2
Tables Turned at the Mall Ch. 02

The action heats up after a sissy is outed by young girls.

by sissysherry2
BDSM 04/28/2018
4.14 27.2k 9 2 14
Hung like a Grape 3 Parts
by sissysherry2
Transgender & Crossdressers06/08/2023
163.7k 75 23 121
1
Hung like a Grape

A small dicked Sissy is outed and humiliated.

by sissysherry2
Transgender & Crossdressers 04/01/2018
4.09 97.9k 45 14 84
2
Hung like a Grape Ch. 02

Lisa continues to strengthen her hold over Sherry!

by sissysherry2
Transgender & Crossdressers 04/05/2018
4.12 36.4k 17 2 23
3
Hung like a Grape Ch. 03

Sherry entertains some new friends at Lisa's party!

by sissysherry2
Transgender & Crossdressers 04/07/2018
3.98 29.3k 13 7 14
The Babysitter Takes Over 3 Parts
by sissysherry2
BDSM06/08/2023
196.4k 52 24 94
1
The Babysitter Takes Over

A closet Sissy is discovered by a teen babysitter.

by sissysherry2
BDSM 03/05/2018
3.83 96.8k 30 11 57
2
The Babysitter Takes Over Ch. 02

Teri the babysitter ups the ante with her sissy.

by sissysherry2
BDSM 03/13/2018
4.28 53.7k 10 7 19
3
The Babysitter Takes Over Ch. 03

Our sissy gets in deeper by the babysitter and others!

by sissysherry2
BDSM 03/14/2018
4.09 45.9k 12 6 18

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