‘crossdressing’ stories

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Active tags
crossdressing 

Category

Siss the Bride

What happens when a man marries his cross-dressed brother.

4.4
132.7k
142
8
207

Cheaters Never Prosper

An 18 year old senior feminized by his teacher.

4.48
231.4k
140
41
176
0

I Hate Him... No More!

Will a bulky jock finally fall for a beautiful trans femme?

H
4.9
91.4k
139
77
220

A Beautiful Teacher

A cross dresser runs into his sexy teacher.

H
4.67
86.2k
138
18
193
0

Becoming the Family Wench

A strict Aunt and Uncle turn their nephew into their niece.

H
4.68
75.3k
138
17
252
0

Lost Bet

Straight guy lost a bet, has to dress as a girl to a party.

H
4.79
119.6k
137
41
277
0

All the Way

My twist on the usual 'I got caught dressing' story.

H
4.5
125.6k
137
23
194

Being Sarah

Crossdresser Sarah gets tormented by two hot female friends.

H
4.64
105.5k
137
24
179
0

Nathalie's Makeover

Nathan gets femenised by his wife.

H
4.59
97.8k
136
28
206

Mother Tricks Son into Fucking Her

Mother and son become lifelong sexual partners.

4.29
111.1k
136
9
216
0

Daddies New Girlfriend

Doug discovers much more then Jerry's petty theft.

4.48
159.7k
136
9
162

Hypnosissy 11

Brian discovers he really loves getting fucked.

H
4.83
87.3k
136
183
202

The Halloween Wager

Two enemies wager on a costume contest.

4.42
204.7k
135
12
195
0

Last Friday: First Sissy Experience

A couple has a night with sissy chastity and a black cock.

H
4.62
87.3k
135
7
202
0

I Begged Him To Kiss Me! Ch. 02

Further submitting to his older male neighbor.

H
4.72
148.1k
135
42
154

Her New Girlfriend Ch. 01

Discovery: he's caught playing dress up.

4.48
289.9k
135
18
179

Story of Sissy Blackmail Ch. 01

Actual Story of how I was first discovered and used...

H
4.59
154.3k
134
24
177
0

Sister’s Satin Panties

Memories of what I did to my sister years ago.

4.17
310.6k
134
11
200

My Girlfriend Made Me a Sissy Ch. 02

Second part. Jess pushes her control further.

4.49
303.2k
133
18
173

Women's Studies Ch. 06

Rule number one: Never assume you're alone.

H
4.86
95.6k
133
26
152

Happy Birthday to Me!

Sam buys his first panties and the shop owner surprises him.

H
4.67
96k
133
20
194

Miss Johnstone's Lesbian Sissy Slut

Young man feminized and dominated by his mature teacher.

H
4.68
104.1k
132
15
214
0

Halloween

Halloween surprise.

H
4.73
82.4k
132
15
202
0

Awakening

The family that plays together, lays together.

H
4.66
503k
132
33
195
0

Aunt Diana Ch. 1

Diana helps Sharon deal with her son's crossdressing.

4.35
260.7k
132
33
217
0

Turning the Teacher

Matt makes the teacher his girl.

H
4.53
209.5k
131
11
168

BoyTrainers, Inc.

A kidnapped 18 yr old boy is turned into a wiggling priss.

4.22
265.1k
130
16
176
0

Shannon's Little Princess

Cameron's girlfriend dresses him up after he makes a mess.

H
4.58
142.4k
129
16
167

The Freshman Favor Ch. 01

College freshman agrees to help out his beefy roommate.

4.44
108k
129
19
183
0

Women's Studies Ch. 09

Lexi's holiday vacation ends with a bang and a blowout.

H
4.83
63.6k
129
56
146

A Boiled Frog Pt. 07

Forget the dash, let's make it a splash.

H
4.77
63.2k
129
162
150

After Church

Crossdressing teen and the dirty old man.

H
4.58
80k
129
7
163

Birthday Treats Ch. 02

A party means more special treats from more family.

H
4.54
162.1k
128
12
202

A Boiled Frog Pt. 02

Simmering in Las Vegas.

H
4.84
108.5k
128
60
150

Prince to Queen

A young Prince is made to marry the usurper of his kingdom

4.48
104.4k
127
9
170
0

Making of Tina Ch. 01: Caught

A story about forced feminization.

4.49
122k
127
6
246

Becoming Wifey Ch. 01

Steve and Danielle get married...with their roles reversed.

H
4.56
102.7k
127
26
187
0

The Sissy Chastity Diary

A sissy loses the key to their cage and soon loses control.

H
4.72
59.7k
127
9
215
0

Sister and Brother

A sister and her crossdressing brother.

4.45
201k
126
9
161

Daddy's CD Waitress

Young crossdresser learns to love living as a woman.

H
4.71
103.8k
126
23
155
0

Our Sissy Slave

My girlfriend and her friend force me to submit.

H
4.54
381.3k
126
26
171

Gay Fem Boy Finds His Man

Feminine gay guy and gay masculine man.

H
4.69
81.2k
126
9
162
0

Sisters Know Everything

My sister finds out my biggest secret.

H
4.57
88.1k
126
22
238
0

Blushing Bride Ch. 03

Crossdresser bride loses his cherry.

H
4.7
283k
126
22
148

Women's Studies Ch. 05

"You're a lady. Cock handling is your business!" Kennedy.

HW
4.82
131.6k
125
39
150

Soft and Hard

Chris gets more than he bargained for at the gym.

H
4.65
54.2k
125
14
237
0

Becoming a Sissy Maid & Slut Vol. 01

How I became a sissy maid & slut to a Master, vol. 1 Ch. 1-3.

4.4
151.3k
125
12
190

Seven Years as a Wife

Man is blackmailed into being a wife.

H
4.65
102.5k
125
68
200

Sexual Sissy Awakening

Man turns into a sissy with help from online author.

H
4.85
64.4k
124
45
230
0

The Consequences of a Winter Storm

A college aged babysitter is caught dressed as the wife.

H
4.73
88.5k
124
16
163
0

A Clean Shirt

Dressed like a boy on the train, I'm picked up by a Daddy.

H
4.64
109.6k
122
37
145
0

Aaron to Ashley

Halloween sparks the beginning of a new life for Aaron.

H
4.57
153.6k
122
20
155

How To Accept Your Cock Curiosity

Advice on becoming a cock sucker and more.

H
4.69
44k
122
66
208
0

A Mother's Promise Ch. 18

Bobby's journey intensifies with mom, aunt and Erika.

H
4.71
249.2k
122
114
147

Creating Ginger Ch. 01

A wife decides her cross dressing hubby needs to go further.

H
4.56
105.6k
121
10
245

Becoming a Bridesmaid Pt. 01

Ashley takes the role of bridesmaid for a wedding.

H
4.62
88.6k
121
12
216

Trophy Wife

Dumped by his Fiancée, Eric finds comfort w his Best Friend.

H
4.8
53.2k
121
17
223

Sam's Pink Panties

Henry's friend is a girl now, and he wants to know more...

H
4.63
98.1k
120
22
154
0

Sex, Drugs and My Neighbour Daddy

My hot neighbour blackmails me into being his little sissy.

4.36
158.5k
120
14
164
0

Let's Be Twins

Denise convinces him dress as her twin for Halloween.

4.33
263.7k
119
8
159
0

Becoming A Sissy Bitch For An Alien

Man becomes sissy bitch for a futa alien.

H
4.7
32.9k
117
11
206
0

That's What Friends Are For Ch. 01

Alex is teased into putting on panties for David.

H
4.53
207k
117
17
173

Weekend Slut for a Huge Cock

I cross dress for a huge white dick for the weekend.

H
4.57
127.2k
117
16
165
0

Caught In Pink Panties

Caught in panties by muscular older neighbor.

H
4.51
257.8k
116
34
157
0

Hypnosissy 09

Brian begins his feminization journey.

H
4.75
77.3k
116
26
161

Kneeling for Daddy

Caught crossdressing and Daddy takes advantage and control.

4.26
172k
115
10
165
0

Crossdressing at the Girls' Academy

Dressed as a girl, he's caught and forced into a gangbang.

H
4.64
119.3k
115
7
180
0

'Jenny' & 'Mike': Date Night

Beginning of a role reversal weekend for a loving couple.

H
4.57
111.8k
115
17
154

A Prom(ise) Fulfilled

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

H
4.7
48k
114
18
178
0

Bah Humbug

Not everyone likes Christmas, until...

H
4.82
53.4k
114
44
125
0

My Roommate's Maid Pt. 01

College student forced to be their roommate's sissy maid.

H
4.59
46.8k
114
17
184

Submitting With Sister

Submissive twins become human sextoys.

H
4.7
77.6k
113
12
272

The Agreement

A man's wife accepts his crossdressing.

H
4.54
145.7k
113
24
148

Shown Up

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

H
4.75
49.2k
113
13
211
0

My Brother's Lover

Lust over transvestites brings brothers together.

H
4.54
147.3k
112
30
138
0

His Son the Tranny

A different kind of father/son bonding.

4.13
251.6k
111
15
156
0

Pretty in Pink

Wife finds his stash of female clothing.

4.45
117.8k
111
15
163

Tabitha

A friend learns about himself while helping a friend out.

H
4.69
63.7k
111
20
142
0

Sissy Housewife Learns to Eat Cum

Sissy Tiffany forced to eat her yummy cum by Miss Jennifer.

4.26
279.3k
111
11
163
0

Shannon's Little Princess Ch. 02

Shannon takes Cameron further into femininity.

H
4.64
126.9k
111
12
134

The Ex's New Toy

Ex-wife brings new boyfriend to a party, Ex-husband becomes.

4.14
116.6k
111
12
161

Study Group Surprise Pt. 02

James embraces being a femboy.

H
4.78
48.4k
111
18
146

Bitch

Once a sissy whore, always a sissy whore.

4.36
157.3k
111
9
135
0

Kasey's Legs

His girlfriend encouraged his crossdressing and more.

4.47
140.9k
110
16
152

Girdled Ch. 01

A son gets caught trying on his mother's girdle & stockings.

H
4.54
93.7k
110
11
170

Mommy's Boy?

A mommy's boy becomes - something more.

4.33
338.8k
110
28
145

Women's Studies Ch. 08

Home for the holidays with Sister and Mom.

H
4.8
68k
109
27
139

Bettering Their Marriage

They wanted better sex, he didn't expect this.

4.29
260.1k
109
33
156

A Day with Ron as My Master

Ordered to give blowjobs for humiliation.

H
4.6
130.2k
109
19
132
0

Obey Thy Neighbor

Sexy neighbor discovers his crossdressing.

4.46
91k
109
12
173

Blushing Bride Ch. 02

He takes next step towards being a blushing bride.

H
4.69
232.5k
108
5
133

Sissification 101: Ch. 03

Eric(a) gets pegged for the first time.

H
4.72
71.4k
108
15
149

Arthur's Hypnotic Transition

Arthur's college roommates ensure college life is exciting.

4.47
152.2k
108
7
181
0

A Halloween Treat

A Halloween Party with tricks and treats.

H
4.81
52.8k
108
30
158
0

A Biker Became My Daddy

A young sissy becomes the girl he has always wanted to be.

4.45
79.8k
108
9
158

Working the Holidays Pt. 02

Classic Christmas tale of blackmail and forced feminization.

H
4.63
69.2k
107
9
138

A Girl And Her Sissy

A girl recounting the feminization of her boyfriend.

4.36
158.1k
107
13
149
0

Brotherly Love, Sisterly Love Ch. 02

The crossdressing twins enjoy a costume party.

H
4.68
202.2k
107
17
116
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