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Search: retro sissy training
278K results
Female POV - feel like a girl
10:40
Female POV - feel like a girl
209K
Sissy Training
87:33
Sissy Training
1.1M
I'm a dirty slave of my wife... she can do everything with me
43:45
I'm a dirty slave of my wife... she can do everything with me
21K
bd1sm
10:40
bd1sm
2M
Obey Your Mistress
HD
2:44
Obey Your Mistress
27K
sissy dildo training - ASS FUCKING
5:57
sissy dildo training - ASS FUCKING
463K
Double Punishment for the Sissy (a Classic)
5:37
Double Punishment for the Sissy (a Classic)
63K
Feminize Yourself
15:44
Feminize Yourself
620K
In Sisssy clothes this is how you will soon look
5:58
In Sisssy clothes this is how you will soon look
1K
Sissy Diagnosis - Hard training by Cezar73
7:27
Sissy Diagnosis - Hard training by Cezar73
460K
What To Do With A Chastity Caged Cock
5:15
What To Do With A Chastity Caged Cock
10K
Sissy games
40:58
Sissy games
1.3M
Apocalust - Ep 30 - Is She A Virgin By RedLady2K
7:02
Apocalust - Ep 30 - Is She A Virgin By RedLady2K
25K
sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!
23:09
sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!
282K
Look how pretty feminized you are, your new rules are now coming to leave your masculine life even further behind
HD
14:17
Look how pretty feminized you are, your new rules are now coming to leave your masculine life even further behind
1.6K
Sissy humiliation hypno trainer
6:42
Sissy humiliation hypno trainer
172K
German crossdresser meet bdsm femdom domina
9:43
German crossdresser meet bdsm femdom domina
110K
The Ultimate Sissy Training by MissBratDom
15:49
The Ultimate Sissy Training by MissBratDom
526K
Little Serving Sissy Wench
5:31
Little Serving Sissy Wench
3.2K
Sissy clit training
8:36
Sissy clit training
90K
Sissy Academy Part 1
8:12
Sissy Academy Part 1
112K
Solve The Riddle - Pt 10 - Who Is This Woman By MissKitty2K
8:35
Solve The Riddle - Pt 10 - Who Is This Woman By MissKitty2K
2.4K
Cucky alphabet sissy
2:18
Cucky alphabet sissy
422K
Hot Sissy Training Compilation
30:13
Hot Sissy Training Compilation
237K
So you want to be a sissy?
39:53
So you want to be a sissy?
167K
SISSY TRAINING VID: Feminized sissy gets pegged by mommy domme
HD
2:10
SISSY TRAINING VID: Feminized sissy gets pegged by mommy domme
73K
TTT
4:59
TTT
200K
Sissy training with Femdom Mistress Tangent
13:04
Sissy training with Femdom Mistress Tangent
1.2M
BDSM0001
57:53
BDSM0001
958K
Mrs Loving Begins Sissy Training at Mother's Request
9:28
Mrs Loving Begins Sissy Training at Mother's Request
844K
Therapeutic Submission: Unleashing Your Inner Sissy
HD
28:46
Therapeutic Submission: Unleashing Your Inner Sissy
75K
Mrs Loving Dressing Her Sissy Crossdresser
1:57
Mrs Loving Dressing Her Sissy Crossdresser
1.4M
Sissy Slut’s First Deep Pegging & Prostate Milking - Ruthless Mistress Trains Your Clitty to Cum Hands-free
10:18
Sissy Slut’s First Deep Pegging & Prostate Milking - Ruthless Mistress Trains Your Clitty to Cum Hands-free
23K
Sissy Goals
3:39
Sissy Goals
452K
Sissy Trainer
5:42
Sissy Trainer
579K
Sissy trainer
4:44
Sissy trainer
179K
Slave training in heat
15:27
Slave training in heat
200K
Sissy cuckold transformation
10:14
Sissy cuckold transformation
700K
Feminization, Crossdressing & Sissification
10:12
Feminization, Crossdressing & Sissification
23K
DAILY TRAINING SESSION
HD
2:57
DAILY TRAINING SESSION
120K
Feminized Training
3:43
Feminized Training
1.4M
Sissy  Cum Trainer
7:58
Sissy Cum Trainer
482K
Exercises 2
4:08
Exercises 2
372K
Tricked and trained sissy cuckold
10:30
Tricked and trained sissy cuckold
704K
Insex bifurcation
102:10
Insex bifurcation
1.4M
What is your kink? - Experience classic dominance, feminization, aroma and extreme fetishes with Domina Lady Julina
21:55
What is your kink? - Experience classic dominance, feminization, aroma and extreme fetishes with Domina Lady Julina
9.3K
1280 »
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