‘sissy’ stories

Active tags
Active tags
sissy 

Category

More than just a Glory Hole Ch. 01

A man trying to get quick release is forced to submit.

4.42
128.5k
115
28
183
0

My Black Son

White guy turns sissy slut for his adopted black son.

4.4
81.7k
115
12
148
0

One of the Girls

Eric unwittingly takes a job as a shemale porn actor.

4.42
99k
115
10
151

Kneeling for Daddy

Caught crossdressing and Daddy takes advantage and control.

4.25
171.8k
115
10
165
0

Not What We Planned Ch. 02

A couple finds a new life as a cuckoldress and sissy.

4.41
73.3k
115
38
145

My Roommate's Maid Pt. 01

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

H
4.59
46.4k
114
17
182

A Prom(ise) Fulfilled

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

H
4.7
47.9k
114
18
176
0

A College Sissy Ch. 03

Ali is humiliated by a sorority.. and fraternity.

H
4.51
132.6k
114
33
142

From Son to Sissy

A young boy's journey to understanding his true sexuality.

H
4.63
70.3k
114
7
180
0

Feminizing First Step Ch. 04

The sissy boy gets a new bikini & endures more humiliation.

H
4.51
165k
114
38
151

Submitting With Sister

Submissive twins become human sextoys.

H
4.7
77.3k
113
12
271

He Wears The Panties

Submissive husband becomes cuckold sissy.

4.22
350.1k
112
40
152
0

My Visit to the Feminization Clinic

A boy goes to a local clinic for a special procedure.

4.42
115.1k
112
61
194
0

Slow Descent into Sissy-Hood... Ch. 01

The beginning of a transformation into a sissy. Chapter 1.

4.47
107.3k
112
16
177

Wife And Bull Take Charge

Wife has to punish cuckold husband for disobedience.

3.95
225.9k
112
0
179
0

Sissy Brainwashing

I had no idea sissy brainwashing was real!

4.29
191.5k
112
14
173

Corey or Cora

Corey dresses as a girl for a friend, but ends up liking it.

H
4.62
75.6k
112
10
142

Lulu's Lockdown Diary

White boy is stuck at home with two big black studs.

H
4.66
48.6k
112
5
158
0

Shannon's Little Princess Ch. 02

Shannon takes Cameron further into femininity.

H
4.64
126.8k
111
12
134

Social Media Star Ch. 03

Boy gets forcibly "stretched" and transformed into a femboy.

H
4.53
94k
111
14
147

Sissy Housewife Learns to Eat Cum

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

4.26
279.1k
111
11
161
0

Caught in Her Panties Ch. 01

I receive punishment after my wife catches me in her panties

4.42
150.7k
111
15
164

To Wear the Horns: A Cuckold Family Pt. 01

Three fat women, three incestuous cuckolds.

4.24
103k
111
12
179

Shown Up

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

H
4.75
48.5k
111
13
209
0

The 5-Day Plan

A naughty headmaster ensnares a delicate pupil.

H
4.53
51.4k
111
7
201
0

Haven the Sissy Slut Ch. 01

Sunday equals Football and Gangbanging.

4.4
145.6k
110
13
139

Tale of Two Sissies

Max seduces and sissifies Jim.

H
4.76
43.7k
110
19
180
0

The Domme Diet Plan Pt. 01

A slut's journey to lose weight his Mistress' way.

4.25
108.3k
110
5
157
0

Study Group Surprise Pt. 02

James embraces being a femboy.

H
4.78
48.3k
110
18
145

The Gentlemen's Panty Club

A young man joins an exclusive fetish club.

H
4.73
90.6k
110
22
172

The Nudist and The Sissy

Max gets a nudist roommate who turns his life around.

H
4.63
45.7k
110
11
167
0

Teased, Denied and Sissified Ch. 01

Ashley discovers his fetish.

4.43
155.2k
110
10
166

Alex to Alexis Ch. 01

Alex is feminized by his mother and sisters.

4.25
121.2k
110
18
143

Best Friend to Girlfriend Ch. 01

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

H
4.76
39.1k
109
14
188

Tricia's Summer Project

A Domme with a gift transforms a shy virgin into a sissy.

4.42
164.6k
109
11
165
0

Deal with a Demon

Femboy makes a deal with a Demon.

4.45
72.9k
109
11
161
0

A Night Out

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

H
4.72
56.7k
109
11
192
0

Young Sissy Ch. 01

The former Master wakes up as a sissy in the Harem

4.41
142.6k
109
7
143

Cream Puff Ch. 01

Sissy finds becomes a strong man's bitch.

H
4.63
66.5k
109
9
152

Locker Room Lust

A smooth water polo jock is targeted by his larger opponent.

H
4.72
34.7k
109
8
191
0

My Dream Girl

A few kinky fetishes revealed and shared with a sexy sister.

H
4.56
99.8k
109
9
250
0

The Roommate Pt. 01-06

Nellie's transition into sluttiness. (Slight edits from og)

H
4.83
64.3k
108
8
194

A Rainy Day

A mature woman rescues a young man from a very bad day.

H
4.56
65.5k
108
14
169

A Biker Became My Daddy

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

4.45
79.6k
108
9
158

Sissification 101: Ch. 03

Eric(a) gets pegged for the first time.

H
4.72
71.2k
108
15
147

Chubby Sissy Meets His Daddy

A chubby sissy meets his daddy for the first time in a storm.

4.3
172.3k
108
16
136
0

Taking Donna's Dick

A sissy taken by his female lodger.

H
4.66
96.3k
107
9
160
0

Feminizing First Step Ch. 05

The sissy boy embraces his feminine side & gets some relief.

H
4.58
136.9k
107
20
147

Arthur's Hypnotic Transition

Arthur's college roommates ensure college life is exciting.

4.47
152k
107
7
179
0

Social Media Star Ch. 02

Boy reluctantly transforms to a femboy for online audience.

H
4.65
73.6k
107
29
148

A Girl And Her Sissy

A girl recounting the feminization of her boyfriend.

4.36
158k
107
13
149
0

The Black Doctor & My Wife

This is the story of how my wife became a black cock slut.

4.03
154.4k
107
10
170
0

Papi's Special Girl

A dominant pimp takes in a downtrodden white boy.

H
4.57
57.9k
107
8
194
0

Working the Holidays Pt. 02

Classic Christmas tale of blackmail and forced feminization.

H
4.63
69k
107
9
138

Bringing Out the Real Me

A black man teaches a white boy to accept himself.

H
4.72
35.3k
107
11
183
0

Under Mommy's Direction Ch. 03

A Son learns that he's a Sissy inside.

H
4.56
102.8k
106
9
135

My Husband. My Love. My Sissy. Ch. 01

Kelly walks in on Tony with her panties.

H
4.68
209.7k
106
38
131
0

I Love My Wife Completely

Being a slut has both advantages and disadvantages.

4.14
160.5k
106
16
168

Humiliated by My Own Sister

Sister forces me to stroke myself in front of her.

4.2
162.3k
106
13
197

My White Boy Sissy Pt. 02

White boy gets his cherry popped by the black dominant jock.

H
4.75
57.7k
106
25
146

Working Out with the Neighbor

Recently dumped guy meets his neighbor's teenage son.

H
4.68
50.6k
106
16
161
0

Hers

His girlfriend likes him feminine. He's hers.

H
4.56
98k
105
11
202
0

My Mom's Shemale Lover Ch. 01

My Mom's Shemale wife forced me to be her sissy.

4.23
79.8k
105
4
184

Straight Boy Fucked By Two Bulls Ch. 03

Liam get's another night with John and Trevor.

H
4.66
53.6k
105
12
165

Queen for a Night

Anniversary gift turns young hubby into weekend wide.

H
4.66
126.4k
105
12
146
0

Boyfriend Turned Girlfriend

Ashley turns Matt into Maddie for the first time.

H
4.59
74.4k
105
32
197
0

Trapped and Trained Ch. 04

The end of Candi's second (and hopefully last) session.

H
4.55
264k
105
21
131

Pool Boy Gets Dressed Up Ch. 02

Pool Boy turned Tranny by his mistress.

H
4.67
200.3k
105
18
135

My Boyfriend is a Better Sister

Girl catches boyfriend crossdressing, makes him weekend slut.

4.35
108.7k
104
12
169
0

Turned into a Sissy Pt. 01

How my ladyboy girlfriend turned me into a Sissy.

4.41
98.3k
104
20
211

Girly Daddy

Sissy dad supports masculine son in every sense.

4.13
122.8k
104
3
160
0

Caitlin and Mistress Vicky

A completely whipped husband is feminized by his wife.

4.34
274.2k
104
18
159

The Rose Diaries Ch. 01

A young man finds himself forced into a new life.

4.3
100.2k
104
15
180

Under Mommy's Direction Ch. 04

A Mother traps her Sissy Son.

H
4.61
113.7k
104
12
141

White Girl Turns White Boy Sissy Ch. 01

White boy comes out to friend and she knows what he needs.

H
4.55
70k
104
18
219

Her First Halloween Ch. 01

David is convinced to dress up for Halloween.

H
4.55
109.8k
104
14
208

Feminizing First Step Ch. 06

The sissy boy makes a new feminized "friend" at a pool party.

H
4.63
129.3k
103
23
145

Feminized by BBC Friend Ch. 03

My BBC friend slowly takes my virginity.

H
4.72
89.5k
103
19
142

Craig's New Life

Forced to play for the other team.

4.49
265.8k
103
25
138
0

How to Fight Racism

Mother punishes her son for his racist outburst.

3.59
71.7k
102
16
199
0

Being My Roommate's Sissy Pt. 01

A sissy has a failed first date and gets humiliated.

4.21
154.7k
102
6
161

Subliminal Obsessions

A lonely, loner guy meets a sissy that changes everything.

H
4.61
74k
102
16
160

Dominant Wife, Cuckold's Reward

A devoted submissive husband, a dominant wife.

4.23
286.1k
102
11
150
0

Turning Sissy - Week 01

A guy online gets more than he bargained for.

4.43
75.8k
102
11
180

Sissy Downfall

My journey from sissy to transformed slut slave.

H
4.52
189.3k
102
7
159

Jailhouse Reunion

An ex-con's past comes back to haunt him.

H
4.62
33.7k
102
8
148
0

Kissing Crossdressers Pt. 01

Hotwife turns hubby into crossdressing sissy.

H
4.53
142.5k
102
20
152

An Uneven Christmas

He's dressed up for Christmas and his friend's enjoyment.

4.45
128.6k
101
8
133
0

Her Property Ch. 01

Tony's new life is honey on a razorblade...

H
4.61
55.1k
101
9
159
0

Neighbors Sissy Son Ch. 04

Tiffany's trip to see the plastic surgeon!

H
4.66
73.9k
101
13
122

John to Jane, Becoming a Bi Cuck

How I became a bi cuck for my fiancé and her bull.

4.37
93k
101
17
168
0

Paul's Sissy Journey

A gorgeous wife molds her husband into Her cuckhold sissy.

H
4.64
75.9k
101
12
183

Lori and Alan, The Beginning

Couple starts down the road of submission and cuckoldry.

4.48
68.4k
101
20
126
0

My New Life in a Frat

Theme party leads to a new lifestyle.

H
4.62
47.7k
101
6
190

Jerkboy Life Ch. 01

Wife reveals husband's secret to her mom.

4.41
138.6k
101
15
172

My Initiation

How I lost my gay virginity. The hard way.

H
4.57
233.3k
101
18
142
0
Active tags
Active tags
sissy
Separate tags with commas. More info in the FAQ