‘crossdress’ stories

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Active tags
crossdress 

Category

Teen is Forced to Crossdress

18-year-old explores his personal kinks.

4.22
815.4k
158
31
212
0

My Initiation

One man's introduction to a new life.

HW
4.74
725.4k
203
132
254
0

"Sissified": 12 Days of Sissy-mas

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

H
4.76
576.2k
823
207
1.2k
0

Nylon Femdom

Sisters deal with David's nylon stocking fetish.

H
4.51
437k
179
46
236
0

A College Sissy Ch. 01

Freshman is feminized, used by male roommate and girl.

4.43
408.3k
383
21
610

Michele and Buster: A Tranny Tale

Tranny Michele meets Buster for sexy fun.

4.07
382.4k
15
7
16
0

Stepmom's Sex Shocker

Son dresses in stepmom's lingerie.

4.3
361.1k
124
4
183

Cum Sucker

Step-sister forces brother into sexual slavery.

4.25
333.5k
82
11
137
0

My Brother's Whore

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

0
319.6k
178
8
244
0

Making a Cuckold

She dominates, sissifies & cuckolds her boyfriend.

4.35
319.2k
121
0
167
0

Fitting Room

A young man finds unexpected lust.

4.37
309.7k
38
16
48
0

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

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

4.47
304.4k
88
10
98

Humiliated Sissy Husband

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

4.27
304.2k
186
25
287

Epiphany

Young man experiences the ultimate feminine act.

H
4.58
293.8k
94
30
109
0

My Son's Big Cock

Widow helps son cross dress for Halloween, and….

H
4.69
281.3k
437
67
672
0

Popping His Cherry

She finally makes him her woman.

4.47
270.7k
418
30
641

My Roommate, Brian

He gets feminized and loves it.

4.36
261.2k
109
23
130
0

Caught Cross-Dressed & Dominated

James is caught dressing in bondage by sexy neighbor.

H
4.56
257.8k
97
0
123
0

Made a Maid Ch. 01

Joel gets caught, forced to become Josie.

4.4
256k
63
9
80

Forced Entry

Transvestite caught in her hotel room is forced into sex.

H
4.52
255.9k
103
14
137
0

Mom Teaches Son to be a Slut

Mom and son fuck go on an adventure, fucking guys

4.11
245.9k
88
21
129
0

Been Caught Cheating

His girlfriend forces him to be fem.

4.21
232.5k
80
10
104

A Good Little Male Slut

He dresses up for night on the town.

4.16
231.8k
21
0
24
0

Caught by My Wife

Life changes when wife surprises him on business trip.

4.26
228.4k
40
10
60

Becoming My Wife's Slut

Wife drugs her husband and turns him into her slut.

4.14
223.6k
86
12
117
0

Cum On My Step-Brother's Face!

Cross-dresser's step-sister forces him into sex tryst.

4.42
223.5k
76
12
121
0

Punished for Cheating

He is forced to wear panties and bra to work.

3.69
217.1k
15
6
19
0

My Summer with Auntie Ch. 01

Young man and his aunt become "close relatives".

4.21
216.3k
65
0
102

Future Mother-in-Law is My Mistress

Mother in law catches me with panties and takes control.

4.23
209.8k
73
25
107

Janie's Got a Dildo

Sister abuses her cross-dressing step-brother.

4.19
207.8k
63
5
100
0

Gay Banged

He is gang banged by neighbor and friends.

4.11
207.4k
46
10
67
0

The Barbeque

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

H
4.67
201.5k
151
15
196

My Father-In-Law's New Bride Ch. 04

Wife helps daddy with bride's new training.

4.44
197.3k
74
14
82

Good Little Bitch Pt. 01

College Halloween party dress-up opens new doors.

H
4.71
194.3k
265
20
391

A College Sissy Ch. 02

Alex is publicly feminized before being pimped out to dorm.

H
4.59
193.3k
179
28
215

Giving My First Blowjob

Crossdresser has oral sex with brother-in-law

4.14
192.7k
14
8
22
0

Dream Girl Pt. 01

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

H
4.7
189.9k
349
36
592

Sissy Downfall

My journey from sissy to transformed slut slave.

H
4.52
189.1k
102
7
158

How I Met My Husband

Describing his journey from college guy to blushing bride.

H
4.59
188.3k
119
11
145

Trapped and Trained Ch. 11

Candi's first day of her new life - back to training.

H
4.59
188.2k
60
14
73

Just Like My Friend

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

H
4.64
188k
137
18
175
0

Crossdressing For My Boyfriend

Chris dresses in lingerie for his boyfriend.

4.47
186.9k
50
18
61
0

Blackmailed into Humiliation

A young man finds himself humiliated by a group of girls.

4.02
185.6k
78
17
111
0

Magic Panties Ch. 01

A man awakes to find a surprise at his door.

4.37
182.4k
130
20
158

Our Sissy Slave Ch. 02

You adventures at the hands and dildo of your girlfriend.

H
4.57
181.7k
77
20
94

Uncles Lessons

A young man goes to live with his Uncle.

4.43
176.2k
87
11
96
0

I Begged Him To Kiss Me! Ch. 01

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

H
4.57
175.3k
120
41
149

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

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

H
4.5
175.2k
129
26
141

Dressed for Sex

He experiences fantasy: feminized by female friend.

H
4.51
168.1k
70
13
95
0

Lingerie Does Make the Man

Wife dresses husband up in pretty panties.

4.37
164.8k
34
7
48

Sister's Step-In

Boy's twin asks him to help her in an odd way.

4.34
160.9k
50
5
68
0

My Summer with Auntie Ch. 02

The sexual tension grows.

4.49
153.7k
22
0
32

Left Alone Ch. 02

Tonya and Walter get to know each other.

H
4.67
153.7k
125
27
134

Birthday Breaking

A requiring her friends, their strapons and my submission.

H
4.62
151.7k
96
17
135
0

Caught in Her Panties Ch. 01

I receive punishment after my wife catches me in her panties

4.42
150.4k
111
15
163

Slut for All Pt. 01

New roommate turns me into a slut for many.

4.3
147.2k
116
8
191

My Daughter's Cuckold Ch. 04

Forced to service my daughter's friends!

4.32
146.4k
66
9
84

Steve's Maid

Steve is sissified slowly by his new dominant maid, Tulip.

4.17
145.9k
44
5
72
0

A New Me...

College boy caught by sister; has his life changed.

H
4.51
143.9k
60
0
82
0

Dance of Lust

He's seduced by the hottest "girls" in school.

4.32
140.7k
54
5
74
0

Adam Loses a Bet Ch. 01

Adam looks good in booty shorts.

4.22
138.6k
148
6
267

Dinner for Two

Cross Dressed and forced to fuck Black Dick

4.35
138k
62
5
88
0

The Bet

Guy is bet he can dress as a girl & fool everyone.

4.4
136.2k
52
6
70
0

A Little Tied Up...

Daniel wakes up in an 'interesting' situation.

3.99
135.6k
32
6
58

Humiliated Sissy Husband Ch. 02

Max suffers more humiliation at the hands of his wife Tanja.

4.4
135.2k
72
27
85

Birthday Present Pt. 02

He becomes his wife's lovely lesbian lover.

H
4.71
135.1k
49
15
60

Caught by My Wife Ch. 02

Shocking changes continue as wife involves others!

4.2
134.8k
22
20
33

Been Caught Cheating Ch. 03

Just when he thinks things are getting better!

4.23
133.4k
27
18
34

Sissy for a Day

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

H
4.67
133.3k
231
34
349
0

A New Spin on Role Playing Games

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

H
4.71
133.3k
202
26
269

A College Sissy Ch. 03

Ali is humiliated by a sorority.. and fraternity.

H
4.51
132.4k
114
32
142

So Much Like Your Mother Pt. 02

Dad finally has his way with crossdressing son.

H
4.59
132k
154
8
194

Mr. Wallace and Me Pt. 01-05

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

H
4.64
128.8k
120
19
141

He Brought Me Panties

A description of a crossdressing liason.

4.22
128.7k
27
14
39
0

A Night to Remember

My first cock while dressed as a woman.

H
4.52
128.4k
43
18
52
0

More

Some games are more compelling than others.

4.42
127.9k
51
0
72
0

How I Became a Sissy for BBC

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

4.37
127.5k
78
0
102
0

Submitting to my Brother in Law

A crossdressing hubby is taken by his Brother in Law.

3.93
127.4k
25
4
43
0

Chrissy Gets Caught

Husband is caught en femme by wife

4.39
126.8k
82
25
98
0

Queen for a Night

Anniversary gift turns young hubby into weekend wide.

H
4.66
126.2k
104
12
145
0

Remember / Forget

You wake up from a hypnotic trance bound & blindfolded.

3.89
125.8k
22
11
47
0

Trained to Have Transvestic Fetish

Husband trained to have a severe fetish.

H
4.55
124.9k
84
20
109
0

Movie Booth Bang

CD's first time in an adult theater.

4.46
124.8k
27
11
33
0

Cara's First Time With A Man

Crossdresser Cara discovers herself on an innocent date

H
4.7
124.6k
81
27
91
0

Virgin Ch. 02

Twenty one year old virgin moves into new house.

H
4.58
124.1k
35
3
47

Humiliated Sissy Husband Ch. 04

Max is forced into losing his Sissy virginity with two men.

4.43
123.9k
72
20
93

Rich Bitch

She catches him dressed and claims him.

4.42
123.6k
57
11
90
0

Giving In To Desire Pt. 01

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

H
4.62
122.9k
95
17
130
0

Fond Memories: The Tale by the Sis

She decides she'd rather have her brother.

4.24
122.1k
23
7
48
0

Crossdressing Son and Dad

Dad unknowingly fucks crossdressing Son.

H
4.62
120.5k
191
8
337

Tranny at the Truck Stop

Tranny is trapped in truckstop restroom and fucked by bikers.

H
4.58
118k
118
14
142
0

Mommy's New Daughter Pt. 01

Mother and friend think of an unorthodox punishment for son.

H
4.65
117.7k
158
20
335

Sissy Maid to Be... Ch. 01

Married sissy in for the experience of her life.

4.47
117.6k
79
13
138

Cheap Sissy Whore To Call Girl

Sissies dream to become America's top call girl.

3.92
116.1k
33
8
46
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crossdress
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