‘crossdress’ stories

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crossdress 

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"Sissified": 12 Days of Sissy-mas

Straight man is turned into a submissive sissy by...

H
4.76
572.6k
821
204
1.2k
0

My Son's Big Cock

Widow helps son cross dress for Halloween, and….

H
4.69
279.9k
432
67
661
0

Popping His Cherry

She finally makes him her woman.

4.47
266.9k
416
30
633

A College Sissy Ch. 01

Freshman is feminized, used by male roommate and girl.

4.43
406.8k
383
21
606

Dream Girl Pt. 01

Get the girl... or become a girl for BBC.

H
4.7
187.5k
347
36
583

Good Little Bitch Pt. 01

College Halloween party dress-up opens new doors.

H
4.7
193.5k
265
20
391

Sissy for a Day

With his wife's help, a man becomes a sissy for black cock.

H
4.67
132.7k
229
34
344
0

My Initiation

One man's introduction to a new life.

HW
4.74
724.7k
203
132
255
0

A New Spin on Role Playing Games

CD plays damsel for a live RPG and becomes a sissy slut.

H
4.7
133k
202
26
266

Pool Day Takes a Turn

Randy forgot his bathing suit.

H
4.64
107.8k
198
26
314

The Femboy and the Tomboy

A shy college student meets the girl of his dreams.

H
4.72
56k
189
28
325
0

Violet Iodine

Futa and Femboy discover one another.

H
4.81
37.6k
188
12
287
0

Crossdressing Son and Dad

Dad unknowingly fucks crossdressing Son.

H
4.61
119.3k
187
8
330

Humiliated Sissy Husband

A wimp of a husband is forced to be a sissy by his wife.

4.27
302.7k
186
24
284

A College Sissy Ch. 02

Alex is publicly feminized before being pimped out to dorm.

H
4.59
192.8k
179
28
215

My Brother's Whore

Dressed as whore, he sucks brother's cock at party.

0
319.3k
178
8
243
0

Nylon Femdom

Sisters deal with David's nylon stocking fetish.

H
4.51
436.5k
178
46
230
0

Loser To Lauren

A guy goes from nothing to the girl of his dreams.

H
4.67
109.3k
177
44
216
0

Going Home with my Girlfriend

Secrets are revealed while visiting his mom with his gf.

H
4.54
110.3k
173
23
282
0

Teen Stud and the School Therapist

School therapist feminized by a student.

H
4.74
96.6k
172
26
248
0

Given Away

A boy is given away as a bride to his Father's coworker.

4.41
96.9k
170
16
298

Prom? Ch. 01

Andy becomes Anna to help a friend.

H
4.68
107.8k
169
18
252

FWB

A friendship becomes more when crossdressing is revealed.

H
4.72
60.6k
168
13
228
0

Teen is Forced to Crossdress

18-year-old explores his personal kinks.

4.21
814.7k
158
31
212
0

Payson's Wedding

A gentle young man and his fiance make wedding plans.

H
4.63
81.9k
157
16
242

Mommy's New Daughter Pt. 01

Mother and friend think of an unorthodox punishment for son.

H
4.65
115.8k
155
20
328

So Much Like Your Mother Pt. 02

Dad finally has his way with crossdressing son.

H
4.59
131.5k
153
8
192

The Barbeque

A lost bet leads to a day as one of the girls.

H
4.67
201.3k
151
15
196

Just Like My Friend

I'm my girly friend's girfriend's girl friend's girlfriend.

H
4.64
187.7k
136
18
174
0

Sissy/Cock Sucker Dictionary

A list to understand the nature of sissies/cocksuckers.

H
4.57
71.3k
134
45
183
0

Magic Panties Ch. 01

A man awakes to find a surprise at his door.

4.37
182.2k
130
20
157

New Job, New Life as as Sissy Slut Ch, 02

Man becomes more of a sissy slut for his "boss".

H
4.5
175k
129
26
141

Left Alone Ch. 02

Tonya and Walter get to know each other.

H
4.67
153.5k
125
27
134

A Lost Bet Leads To Sissification

A lost bet to a friend leads to a humiliating sissification.

4.41
105k
123
8
197

Stepmom's Sex Shocker

Son dresses in stepmom's lingerie.

4.3
360.8k
123
4
182

I Begged Him To Kiss Me! Ch. 01

A young married guy is seduced by his elderly male neighbor.

H
4.57
175k
120
41
147

Mr. Wallace and Me Pt. 01-05

My fat, ugly boss makes me dress like a girl.

H
4.64
128.6k
120
19
140

Making a Cuckold

She dominates, sissifies & cuckolds her boyfriend.

4.35
318.9k
119
0
164
0

Good Little Bitch Pt. 02

Chrissy's wild night continues!

H
4.73
59.8k
119
12
143

How I Met My Husband

Describing his journey from college guy to blushing bride.

H
4.59
188.2k
119
11
145

I Hate Him...

Can straight Texan jock lust for a pesky feminine activist?

H
4.76
38.6k
118
54
184

Hypnosissy 09

Brian begins his feminization journey.

H
4.75
75.8k
117
26
160

Tranny at the Truck Stop

Tranny is trapped in truckstop restroom and fucked by bikers.

H
4.58
117.8k
117
14
141
0

Feminized by Girlfriend

A curious boyfriend gets feminized by his girlfriend.

H
4.54
91.6k
116
46
225

Slut for All Pt. 01

New roommate turns me into a slut for many.

4.3
146.7k
115
8
188

A College Sissy Ch. 03

Ali is humiliated by a sorority.. and fraternity.

H
4.51
132.1k
114
32
143

A Prom(ise) Fulfilled

A closet crossdresser's stepbrother needs a prom date...

H
4.7
47.4k
114
17
176
0

Caught in Her Panties Ch. 01

I receive punishment after my wife catches me in her panties

4.41
149.9k
111
15
161

Fetish Factory

CD gets turned into a fetish doll.

H
4.66
67.1k
111
18
152
0

The 5-Day Plan

A naughty headmaster ensnares a delicate pupil.

H
4.54
50.7k
110
7
200
0

My Roommate, Brian

He gets feminized and loves it.

4.36
260.9k
109
23
129
0

Best Friend to Girlfriend Ch. 01

Evan finally gets the chance to be fucked by his best friend.

H
4.76
38.2k
107
13
185

A Night Out

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

H
4.72
55.7k
106
11
184
0

Blackmailed and Seduced by Peter

Steve is caught and tricked in pleasing an older man.

H
4.74
52k
105
19
148
0

A Halloween Treat

A Halloween Party with tricks and treats.

H
4.81
52k
104
30
153
0

Queen for a Night

Anniversary gift turns young hubby into weekend wide.

H
4.66
126k
103
12
145
0

Forced Entry

Transvestite caught in her hotel room is forced into sex.

H
4.52
255.7k
103
14
135
0

Sissy Downfall

My journey from sissy to transformed slut slave.

H
4.52
188.8k
102
7
156

Stuck at a Stranger's House

I get stuck at a stranger's house after my car gets totaled.

H
4.61
77.1k
101
12
124

Summer with Unkie

Feminine boy spends the summer with his Step Uncle.

H
4.67
60k
99
13
144

Finley and his Land-Lady

A gentle boy moves in with an affectionate, mature Land-Lady.

H
4.58
87k
98
20
135
0

My Life Pt. 01

A young trans girl's first sexual experiences.

H
4.66
74k
98
21
139

Homecoming Queen Ch. 02

Allison and Jason continue their relationship.

H
4.78
33k
98
9
124

The Family Pt. 01

Desperation leads to discovery.

H
4.84
31k
97
29
124

Maid to be a Housewife

Pandemic leads to housewife opportunity.

H
4.68
69.9k
97
21
139
0

Caught Cross-Dressed & Dominated

James is caught dressing in bondage by sexy neighbor.

H
4.56
257.5k
97
0
123
0

Walk of Shame

He's made to dress as a slut and walk through the ghetto.

H
4.53
62.8k
97
20
121
0

Birthday Breaking

A requiring her friends, their strapons and my submission.

H
4.62
151.5k
95
16
130
0

Giving In To Desire Pt. 01

'Straight' guy gets caught in panties and gives in...

H
4.62
122.7k
95
17
130
0

How Nathan became Natalie Ch. 01

Nathan discovers the bliss of being a sissy cocksucker.

H
4.51
61.5k
95
11
125

Epiphany

Young man experiences the ultimate feminine act.

H
4.58
293.7k
94
30
109
0

Obedient Delicious Submission

His wife comes home early and gets a submissive sissy toy.

H
4.63
92.5k
92
13
136
0

The Punishment

Fantasy football punishment leads to feminization, gangbang.

H
4.54
79.5k
89
13
140
0

Caught with Consequences

An intern learns a valuable lesson!

H
4.68
65.1k
89
7
127

Mom Teaches Son to be a Slut

Mom and son fuck go on an adventure, fucking guys

4.11
245.5k
88
21
129
0

All the Way Ch. 02

Continuing story of George and Clarissa.

H
4.64
53.6k
87
20
105

My Father-In-Law's New Bride Ch. 02

Father-in-law continues son-in-law's bridal training.

4.47
304k
87
10
96

Uncles Lessons

A young man goes to live with his Uncle.

4.43
176.1k
87
11
96
0

Homecoming Queen Ch. 03

Allen takes life as Allison even further.

H
4.81
27.2k
87
43
112

Becoming My Wife's Slut

Wife drugs her husband and turns him into her slut.

4.14
223.2k
86
12
115
0

The Making of Meaghan Ch. 01

An unsuspecting small town guy is turned into Dave's girl.

4.35
86.7k
85
8
119

Crossdressing Son and Dad Pt. 02

Son goes back for more with dad.

H
4.7
50k
85
8
125

Trained to Have Transvestic Fetish

Husband trained to have a severe fetish.

H
4.55
124.7k
84
20
109
0

Pool Day Takes a Turn Ch. 02

Forgotten bathing suit leads to a day of fun for a sissy.

H
4.74
67.8k
84
14
124

Jacki's Journey into Sissyhood

A crossdresser's journey into be a full-fledged sissy.

H
4.57
115.1k
84
6
123

Cum Sucker

Step-sister forces brother into sexual slavery.

4.25
333k
82
11
136
0

Wide Hips for a Guy

She pervs on his big round ass.

4.49
29.2k
82
10
117
0

Chrissy Gets Caught

Husband is caught en femme by wife

4.39
126.6k
82
25
98
0

My Little Pussyboy Pt. 02

A boy learns more about his wifely duties.

4.44
79.9k
81
10
124

Cara's First Time With A Man

Crossdresser Cara discovers herself on an innocent date

H
4.7
124.3k
81
27
91
0

My Best Friend's Girl

Femboy becomes his best friend's girl for a day...

H
4.72
46.2k
80
12
150
0

Been Caught Cheating

His girlfriend forces him to be fem.

4.21
232.3k
80
10
104

Sissy Maid to Be... Ch. 01

Married sissy in for the experience of her life.

4.47
117.1k
79
13
138

Left to Their Own Devices

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

H
4.81
21.4k
79
12
141
0

Feminized by Girlfriend Pt. 04

Carla continues to complete feminization.

H
4.66
57.3k
78
47
113

The Harem Ch. 02

It begins in earnest.

H
4.71
31.9k
78
11
109

How I Became a Sissy for BBC

The story of how I became a white sissy for BBC.

4.37
126.8k
78
0
102
0

Role Reversal for My 50th

Dressed and fucked by my wife for my birthday.

H
4.57
60.7k
78
7
110
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