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Search: sissy train
86K results
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5:29
You failed the exam, teacher wants to punish you by feminizing and fucking your sissy hole(FEMINIZATION ROLEPLAY - AI GENERATED)
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0:48
Date with Your Chastity Keyholders POV
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6:35
On the beach, I hold my husband by his balls
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4:30
Let me taste your cum like a slut
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3:27
Sissy Feminization
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My Sissy Sucks My Locked Husband… Who Thinks It’s Me - Mistress Julia
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Mommy's Sissy Anal Training
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I'll guide you to become the sissy you were meant to be (FEMINIZATION ROLEPLAY - AI GENERATED)
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1:51
Sissified, caged, humiliated & pegged
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Piss Enema Release and Fisting for Sissy Slut
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5:22
CUCKOLD CUMS IN PANTIES LIKE A GIRL
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6:14
Why is she scared of femboy sissy's cumshot?
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3:38
Mistress Fucks Her Sissy Maid with an Alien Dildo
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1:50
Roommate Makes You Wear Dirty Panties for Not Finishing Chores
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5:49
Female domination on sissy whore in chastity cage
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8:12
Sissy Cock Trainer
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6:54
Mistress trains Husband to do housework
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15:42
Pushing SISSY's PROSTATE until he leaks for me!
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20:32
ANAL DILDO HERO-ANAL MARATHON 3: PRO RIDER
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1:56
A GangBang for the Sissy Slut
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6:10
Blowjob in Chastity Cage for SissyBoy
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Mistress fucks her slave balls deep with MHT Cody Cachet Large and Willie Wanka sex machine, Sissygasm, Anal Orgasm
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8:31
Sissy Secretary: Submissive Male Feminized into Bimbo for Job Interview, Learns how to Pee Like a Girl, Bonus Pegging & Fisting
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7:09
I Own Your Cock
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7:45
Handjob with prostate massage for my sissy boy
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24:25
JOI Jerk off Instruction and Sissification for Newbie Slut
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4:35
Cock Worship Sissy Trainer
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9:07
Cuckolded, caged and humiliated
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Cuckold Humiliation Compilation
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10:06
Her femboy stands and flows like a whore
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10:11
Cock milking prostate massaage
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12:15
Sissy Training Level 4
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65:29
Best of Harmony Rose vol 1
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Cunilingus and piss in my cuckold's mouth outdoors
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71:08
Mistress Flo Fists the Ass of Two Mature Transvestites
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14:01
Slave’s Anal Training with the John Thomas’ Anal Torpedo
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11:01
The sissy fag curse by Goddess Lana
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Lady Cherry train her sub to a sissy slut
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17:11
CUM HUNGRY
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Maximum anal punishment - Sissy Training
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Super Mean - Sissy Gets Her Ass Fucked by a Caged Slave
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5:10
Guided Sissy JOI – Cock Sucking, Spit & CEI
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2:24
NEW VID: IMPATIENT SISSY SUCKS ME OFF WHILE I FINISH MY GAME
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8:06
JOI ANAL CEI - YOU'LL BE MY SLUTTY SISSY AND FUCK YOUR ASS
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8:50
Sexy Wife with Big Strapon pegging her Husband with Handjob
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11:38
Slowly working my hand in his ass. HIS FIRST FISTING!!!
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