‘sissy boy’ stories

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sissy boy 

Category

His Sissy Boy

A very dominant man uses his sissy 'wife'.

4.39
372.1k
164
21
205
0

Stepsister's Surprise

His new stepsister is pretty but is he ready for her?

4.23
296.9k
69
0
81
0

Sissy Boy Secretary

Dominant boss & secretary interact.

4.29
285.8k
55
10
76

Woken by a Blow Job

Mike wakes up to find his friend giving him head.

4.37
186.2k
49
0
58
0

Glory Hole Favors

Can't always take - you've got to give, too.

H
4.57
181.3k
111
7
140

The Perfect Age Ch. 02

A sissy boy learns more...and more.

H
4.58
178.1k
92
10
100

Plumbed During Work

Role playing with client gets out of hand.

H
4.53
166k
20
8
25
0

Daddy Discovers I'm a Sissy Ch. 01

My sissy secret isn't a secret anymore, and that's okay.

4.1
161.9k
81
19
125
0

The Perfect Age Ch. 03

A sissy learns much from his mother, from his boyfriend too.

H
4.57
161.7k
80
16
87

A Kept Sissy Boy

A sissy boy grows more addicted to his boyfriend.

4.36
156.8k
115
7
149
0

How I Became Sissy Willow Ch. 04

Willow's training as sissy for wife & lover continues.

4.35
145.1k
22
23
26

Sissy Boy Secretary Ch. 02

Dominant boss & secretary interact, again.

4.47
142.3k
18
4
22

Outed and Married

A sissy is exposed completely.

4.23
127.5k
76
9
101

Daddy's Little 'Girl'

The perfect dirty little sissy girl...that would be me.

4.41
124.4k
95
1
126
0

The Stepmother Ch. 3

Billy goes shopping for panties.

3.84
123.4k
8
4
8

A Working Sissy Girl

A sissy girl does what she has to do to please a client.

4.1
117.5k
23
2
34
0

Workout Partner with Benefits

He helps a sexy sissy boy and gets a big payoff.

H
4.59
116k
100
19
121
0

A Very Big Man!

My all-the-way-rock-hard 11" boyfriend.

H
4.62
101.2k
92
5
114
0

Mother Dear Pt. 02

a son helps his mother with household chores

4.26
100.2k
45
2
57

Sam's Pink Panties

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

H
4.63
97.4k
119
22
152
0

Sissy Boy Secretary Ch. 03

He returns to the store.

4.47
95.6k
16
3
19

Glory Hole Favors Ch. 04

The End: sometimes, you have to learn the hard way.

4.45
94.9k
41
5
45

Sissy Boy Secretary Ch. 07

Still more antics of dom boss and secretary.

4.1
90.9k
7
1
12

Sissy Boy Secretary Ch. 04

The fun continues, with friend's help.

4.46
90.3k
12
5
15

My Little Slut

Sissy boy slut finally gets used by Mistress.

4.29
89k
29
3
35

A Photo Session, My First

A sissy 'girl' gets put on display, for offer to others.

H
4.52
85.1k
61
4
88
0

The Perfect Age Ch. 06

A sissy 'girl' meets her first real lover.

H
4.67
74k
42
4
50

A Night at the Club

A sissy boy pleases a new man.

4.49
72.6k
47
6
63
0

Call Me, Lover!

A series of "first's" all in one visit to the adult store.

H
4.5
71.1k
35
6
46

Sissy Boy Secretary Ch. 09

Elaine's neighbor Tammy needs help.

4.01
69.3k
6
3
9

Mother Dear Pt. 04

Mary's lesbian slave girl learns about her son.

4.33
69k
23
3
26

Outed and Married Ch. 02

A sissy 'girl' and her husband entertain.

4.49
68.6k
41
7
49

Andy's Journey Ch. 04

Andy's delightful humiliation.

4.47
65.8k
27
11
41

My Little Slut Ch. 02

Sissy boy wants things to go further....

4.16
62.2k
8
0
10

Mother Dear Pt. 12

My total submission, in my Mother's house.

4.31
60.9k
22
1
34

Little Sex Toy Ch. 07

A sissy girl's first fraternity 'party'.

4.49
59.6k
41
3
52

A Biker Became My Daddy Ch. 02

The second chapter of being a Biker's sissy.

H
4.57
59k
60
8
77

For His Mistress' Pleasure Ch. 04

The party starts and he is the main attraction

4.39
56.5k
5
1
6

Mother Dear Pt. 08

A loving son satisfies his mother.

4.1
54.9k
26
3
34

A New Adventure...

A little experimenting never hurt anyone.

3.57
54.4k
20
4
29

Sucker Boys

A Domme, her best sissyboy painslut & you.

H
4.71
53.8k
15
3
23
0

Behind the Blinds

The man installing the shed discovers why the shades moved.

4.4
52.7k
29
6
39
0

A Very Dirty Little Sissy 'Girl'

A driven sissy girl sex addict speaks.

4.4
51.7k
29
4
37
0

The Man That Owns Me Ch. 04

A sissy is taken to a new level.

H
4.63
51.3k
39
4
48

Mother Dear Pt. 06

Mother's son and her lesbian lover reach an understanding.

4.33
50.9k
19
2
24

Outed and Married Ch. 03

A sissy displeases 'her' husband, but will make up for it.

4.41
48.5k
28
1
32

The Man That Owns Me Ch. 03

Sissy learns a new 'trick', consummates her relationship.

H
4.54
48.1k
29
2
35

Mother Dear Pt. 14

A loving mother introduces her son to a new man.

H
4.66
43.8k
23
2
38

The Agency Ch. 02

Mike returns to start his new job and faces new challenges.

H
4.61
42k
54
8
76

Mother Dear Pt. 13

A mother's reward for a loving and devoted son.

4.28
41.8k
23
3
33

Abandoned Parking Lot Pt. 01

After fighting with a drunk girlfriend, a boy is fed up with.

3.61
33.4k
7
5
10
0

Locked Away and Lovin' It Ch. 02

One year on I'm a happy established sex toy and proud of it!

4.16
28.9k
8
1
14

How James and I Started Together

James and Alin's first meeting gets a little sticky.

4.2
26.7k
6
2
8

Uncle Ernie

I really needed a change of scenery, boy, did I get it too!

4.14
22.5k
17
4
27
0

Shopping with Chantelle

Wear all these girlie clothes while we shop, darling. Mmm.

4.18
20.9k
7
7
15
0

Discounted Carpet

Filtering with contractor opens some new doors.

H
4.56
18.8k
14
3
16
0

Princess

She goes on a date.

4.36
18.5k
6
0
9
0

A New Adventure... Ch. 03

A little experimenting never hurt anyone.

4.15
16.2k
9
0
10

Secrets of The New World Order Ch. 04

Jennifer's new playmate; Sarah chooses the highest bidder.

H
4.5
16.1k
3
1
6

The Best Double Dare

My first night as a sissy boy.

4.43
11.2k
8
2
22

Party Pizzazz Ch. 02

It's a waste of precious time to deny who I am.

H
4.5
6.7k
1
1
2
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sissy boy
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