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‘gay sissy’ stories

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His Sissy Bitch Ch. 04

A man's sissy girl is to become his very public little bitch.

by keptsissy in Transgender & Crossdressers 09/03/2011
H
4.56
234.4k
103
11
109

The Perfect Age Ch. 02

A sissy boy learns more...and more.

by keptsissy in Transgender & Crossdressers 08/22/2011
H
4.58
178.6k
91
10
99

Was I Raped? Ch. 02

I confront the man who took my ass.

by eviltwin52 in Gay Male 12/19/2016
4.28
167k
60
12
80

Sissy for Older Men Ch. 01

Chapter by chapter of my experiences with older men.

by sissyforold in Gay Male 02/09/2013
4.15
137.9k
52
14
64
0

Turning into His Toy Ch.01

The beginning of how I went from man to a sissy slut.

by vaultdweller111 in Transgender & Crossdressers 06/19/2016
4.32
110k
56
8
70

Turning into His Toy Ch.03

My feminization begins.

by vaultdweller111 in Transgender & Crossdressers 07/17/2016
4.33
88k
33
5
37

Playing the Part

A 'boy' becomes a sissy when he is fucked by a man.

by Sissysdream in Transgender & Crossdressers 01/02/2020
4.36
86k
42
11
64
0

Turning into His Toy Ch.02

I meet daddy and he lets me choose my fate.

by vaultdweller111 in Transgender & Crossdressers 06/22/2016
4.22
74.5k
25
6
29

Sissies Don't Have Dicks

Straight man gets hooked on gay sissy hypnosis videos.

by CinaedeFuri in Gay Male 01/21/2021
4.07
47.1k
24
6
47
0

Lovely Brunette

She comes home and catches her husband wearing a dress.

by LoveIsUniversal in Gay Male 03/16/2018
4.47
43.2k
42
11
52
0

Simple Submission

Her neighbor wants to be submissive while wearing a dress.

by LoveIsUniversal in Gay Male 04/06/2018
4.3
34.7k
15
4
27
0

The Gentle Master and The New Slave

A sub, new to the scene is gently brought forward.

by eljayb in Gay Male 04/08/2019
4.1
30.4k
7
8
12
0

Lace and Love Ch. 02

Sissy Alice prepares for her master's return home.

by vaultdweller111 in Transgender & Crossdressers 05/23/2016
4.23
26.8k
10
1
12

Lace and Love Ch. 03

Jake returns home and is greeted by Sissy Alice.

by vaultdweller111 in Transgender & Crossdressers 05/25/2016
4.21
24.5k
9
1
12

Lace and Love Ch. 04

Alice gets face-fucked by Jake.

by vaultdweller111 in Transgender & Crossdressers 06/07/2016
4.17
19.5k
7
1
8

Sissy Sex Girls, Ellen at Her Best

A sissy girl is one of several pleasing men at an orgy.

by keptsissy in Fetish 10/16/2020
H
4.51
15.6k
18
5
28
0

A Sissy's First Wedding Anniversary

A Sissy Girl getting ready for her Black Husband.

by Smsumani in Transgender & Crossdressers 01/30/2024
4.29
13.4k
9
2
22

Rod's Boy Pt. 02

Being Rod's boy meant a lot of doors would need to be opened.

by Fag4cock in Gay Male 10/30/2021
4.45
13.3k
9
0
14

Rod's Boy Pt. 06

Part six in my transformation to Rod's boy

by Fag4cock in Gay Male 11/03/2021
4.38
7k
3
0
4
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