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Search: sissy train
86K results
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24:27
Sissy Cuckold Husband Life Stages Chapter 1 Part 6
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94K
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6:21
Stepmom Makes You her Sissy Bitch
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93K
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16:21
The evolution of the size of a chastity cage cock
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86K
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9:35
Mistress Rides and Sucks Sissys Strap-on - Cock in Chastity Cage, Useless and Denied
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36K
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13:30
Fantastic pulsating ruined orgasm with spikes chastity on big dick. Amateur femdom handjob
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74K
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10:14
Shaving and balls busting part 2
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40K
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8:37
Mistress wants to dress you up like her fucktoy and help you train with a strap-on (FEMINIZATION ROLEPLAY - AI GENERATED)
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51K
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1:10
Mommy Ruby first time with a t-girl
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3K
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6:50
Jump, bitch, until you cum. Pegging without hands.
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160K
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2:50
My sissy bitch’s greedy boipussy swallows my 12inch BBC her clitcock has never looked so more tiny and pathetic
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25K
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5:18
Take Your Cum Facial - Sissy Bi Encouragement - Cumslut Training
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4.2K
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58:05
POV Cuckold vol 30
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7.1K
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24:57
What’s my name part 2
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96K
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24:06
Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training
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5.5K
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11:28
BBC worship – multiscreen
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154K
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9:11
Sissy Training Level 8
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246K
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26:34
SISSYGAMS Fest!! No mercy PEGGING gave me 8x PROSTATE ORGASMS!
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49K
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12:50
NEW sissy gets deflowered with monster DILDO
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82K
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1:33
AFTERNOON PEGGING: feminized boyfriend gets his ass pounded by mommy
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30K
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9:26
CUM CHALLENGE FOR BISEXUAL PERVS
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38K
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5:02
100 Seconds to Cum for BBC
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354K
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4:20
Locked in chastity under mistress
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146K
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14:05
Femdom Pegging Latex Sissy by Dominafire
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97K
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3:44
Sissy transformation
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272K
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17:32
How to stay limp and soft forever
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27K
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0:55
Dominafire Rough Pegging Tied up Sissy
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82K
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4:18
Sissy husband dressed up as a worthless slut and fucked in his ass by his mistress
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77K
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2:44
Obey Your Mistress
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26K
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1:38
The final transformation - Mistress Tatjana
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280K
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20:24
POV Sissy Pegging - Custom for FRED
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207K
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4:31
Sissygasm JOI - Rub That Clitty Like a Good Girl and Cum Without Stroking
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10K
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3:24
Dominant wife punishing and humiliating her cuckold sissy maid
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228K
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11:09
Wife dresses her husband in her lingerie and then fucks him with her strap-on and plastic cock
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226K
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2:34
Bitch boi husband dresses up as a sissy bitch and pegged in his tight boi pussy
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123K
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8:12
Trained Through the Screen: Denied, Rewired, Relocked
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24K
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56:50
Dildo Hero - riding the A train
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243K
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5:51
CBT : I Test a Humbler with Spikes on my Slave - Mistress Julia
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272K
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1:34
Pegging my sissy boi on holiday
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54K
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8:12
Double Domination - We Turn You Gay and Alpha Fucks You
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24K
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9:50
Cock Brainwash
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128K
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31:00
Anal instructor 3 (Hard anal Joi)
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190K
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40:31
DILDOGAME. DAY1.PART1. STEPBROTHER MY LITTLE HELPER
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128K
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16:24
Lady Fyre's School for Boys and Good Sissies
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63K
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93:16
Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest
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59K
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16:59
Friday Fun Time with Lisa, Charlotte and Mike
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329K
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1:10
Locktober - Cage 7: Business man transformed into Sissy bimbo slut by hot Mistress in Leather Leggings
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111K
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