Sissy Training 1,915 videos

• 07:46

  Strict mistress dominates sissy femboy with massive strap-on, rewarding him in the end

  11 months ago

  XXXVogue

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• 13:06

  Widespread sissy butt gets thoroughly examined P1 / 2

  11 months ago

  XXXVogue

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• 05:45

  Submissive sissy maid obediently cleans under her mistresss guidance

  11 months ago

  XXXVogue

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• 05:00

  Sissy Dick Sucking Training - Brat Perversions

  1 year ago

  xShemaleTube

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• 06:05 thumb_up 79%

  So hot cumming after 7 days in chastity and anal training

  1 year ago

  xHamster

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• 09:34

  Sissy biotch instructing

  1 year ago

  VideoSection

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• 06:16

  Sissy Games : When my Cuckold Husband Meets my Lover - Maitresse Julia Femdom

  2 years ago

  xHamster

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• 05:29

  New Violet Dildo for My Sissy Bitch

  1 year ago

  xHamster

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• 01:45

  Spanking & pegging his sissy ass and making him eat his own cum

  2 years ago

  xHamster

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• 03:05

  Crushing and Trampling her Cock with my Heels, CBT Training Technique, Mistress Julia

  2 years ago

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• 1:03:10

  Sissy lesson: how to be a good slut

  2 years ago

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• 01:32 thumb_up 43%

  Sissy Maid Service Training 2 The Inspection And Reward - Brookelynnebriar

  3 years ago

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• 08:16

  Egyptian sissy gets his pussy stretched

  3 years ago

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  BECOME THE SUPERSLUT - SISSY HYPNOSIS BITCH

  6 years ago

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• 19:38

  Smoker makes you a sissy

  5 years ago

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  JayneLynne69 - 443 Training A Sissy

  6 years ago

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• 11:47

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  4 months ago

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• 18:17 thumb_up 89%

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  6 years ago

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  Virtual Femdom Mistress JOI

  10 months ago

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• 05:49 thumb_up 43%

  My spouse in a chastity cage goes wild

  6 months ago

  XXXVogue

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• 13:57

  STEP MOMMY DRESSES HIM IN PANTIES AND MAKES HIM CUM TWICE

  1 year ago

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• 11:43

  Vends-ta-culotte - Stunning French Foot Goddess Explains How She's Going to Take Care of Your Ass

  1 year ago

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• 05:18

  I have fun with my husbands chastity cages

  1 year ago

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• 12:18 thumb_up 20%

  Vends-ta-culotte - Humiliation and punishment by a beautiful French dominatrix in a latex suit

  1 year ago

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• 07:08

  Sucking Small Dick Bitch Making It Cum In My Mouth And Swallowing Her

  1 year ago

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• 09:32

  Good Girl Gone Bad PART 6 by MissKitty2K

  1 year ago

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• 05:20

  My husband watches me while I get ready for my lover

  1 year ago

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• 05:10

  In the bath, my submissive in a chastity cage takes care of my feet

  1 year ago

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• 02:24 thumb_up 20%

  10 MIN MAX POWER CHALLENGE - SYBIAN PROSTATE ORGASMS Prostate orgasm overload. Sub Tommy rides Sybian

  2 years ago

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• 08:34

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  3 years ago

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• 10:26

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  3 years ago

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• 01:10

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  3 years ago

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  Every straight guy should experience a prostate orgasm at least once in his life -Institution X-

  3 years ago

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  I made him my slut and fucked his ass

  3 years ago

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• 17:05 thumb_up 60%

  Fucking My Bitch’s Asshole, Making Her Cum All Over Me

  5 years ago

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• 25:44 thumb_up 60%

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  5 years ago

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• 06:40

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  5 years ago

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• 14:03 thumb_up 60%

  Sissy Training at Work

  1 year ago

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• 07:00 thumb_up 78%

  BECOME THE TART (no Text)

  5 years ago

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• 13:29

  Sissy Training Session Part 1 - October 12.2023

  2 years ago

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• 05:33

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  3 years ago

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• 20:51 thumb_up 22%

  Stop! Feminine sissies do not jerk their cock - sissy training and feminization with Lady Julina

  2 years ago

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• 15:00 thumb_up 80%

  Alexis Amadahy And Jade Sissy Training And Strap On

  4 years ago

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• 22:46

  Rubber Sissy Training

  3 years ago

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• 05:31 thumb_up 43%

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  6 years ago

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• 08:00

  Sissy Slut Trained And Spit Roasted

  3 months ago

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• 04:22 thumb_up 56%

  Sissy training: The urge to suck

  8 years ago

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• 08:11 thumb_up 67%

  Dominatrix dominatrix April - two mistresses and a Sissy Whore P2

  10 months ago

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• 07:58 thumb_up 50%

  BDSM training for sissy maids in femdom group session

  7 months ago

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• 07:27

  Sissy slut dominated by big strapon - strap-on play, feminization & blowjob training

  11 months ago

  XXXVogue

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• 10:08

  Strap-on fucking my transformed sissy whore in black

  1 year ago

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• 08:28 thumb_up 33%

  Compilation of teaser trailers for Sissy Stocking Crossdressing Encouragement Harassment

  11 months ago

  XXXVogue

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• 11:58 thumb_up 40%

  Sissy gets anally pounded with her superglued pussy - part 3 of 3

  1 year ago

  xHamster

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• 27:14

  Sweet sissy ass tries two strapon cocks

  1 year ago

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• 11:46 thumb_up 40%

  DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

  1 year ago

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• 05:37 thumb_up 90%

  Double Punishment for the Sissy (a Classic)

  2 years ago

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• 11:43

  Closed Captions Anal Training for Sissies

  1 year ago

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• 06:39 thumb_up 91%

  Advanced High Heel Training: The Treadmill Part One

  2 years ago

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• 02:09

  Bi Humiliation with Sissy Slut and White Slave

  2 years ago

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• 04:15

  Slave Pillory 2.0: Outing of my Sissy Bimbo Slut

  2 years ago

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• 10:29

  Vends-ta-culotte - Bossy dominatrix woman wants to feminize you and train you to enjoy cock in your ass

  2 years ago

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• 02:16

  Sissy Crossdresser Boyfriend Dildo Training

  2 years ago

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• 12:06

  Teaching my SISSY grilfriend how to FUCK a real pussy

  2 years ago

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• 09:48 thumb_up 40%

  Miss Jade – Training you as my Sissy Slut

  2 years ago

  IcePorn

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• 02:02

  Sissy Slut Pegging Feminization Training Zero Miss Raven Femdom Sissyfication Rough Huge Strapon Strap On Male Slave

  3 years ago

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• 02:24

  SISSY SLUT FUCKED 8 INCH STRAPON by DominaFire

  3 years ago

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• 05:43

  Sissy Bi Encouragement Roleplay with Tattooed Punk Goddess Webcam Recording Live Private Show

  3 years ago

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• 10:41

  Ich ficke deinen Sissy Arsch!

  4 years ago

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• 17:33

  Sissy Feminization Bitch - come on, let me fuck your sissy pussy with my big fat strap on

  3 years ago

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• 05:46 thumb_up 67%

  Swallow His Cum Faggot (point Of View Cumshot In Your Sissy Mouth Femdom Training)

  4 years ago

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• 29:00

  Talishas Sissy Anal Trainer

  5 years ago

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• 03:39

  Sissy Goals

  4 years ago

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• 12:11

  Jerk off instructions for you, little anal sissy

  5 years ago

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• 01:22 thumb_up 77%

  Sissy Slut Training Pt1 - TacAmateurs

  5 years ago

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• 10:55

  Sissy Mind WARP

  5 years ago

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  German Mastix Silvia trains her sissy maid

  12 years ago

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  Sissy Slut Nina Training

  7 years ago

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• 18:51 thumb_up 33%

  Transformation from man to woman: makeup, lashes, and lipstick

  11 months ago

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• 09:02 thumb_up 43%

  My wondrous bootie with a strap-on fucks the beautiful ass of my guy

  9 months ago

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• 07:28

  Dominatrix Julias rewarding morning awakening: blowjob, fisting, pegging, and more!

  11 months ago

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• 20:38

  Metronome JOI Turning You Into a Fag Cocksucker While You Jerk off to My Voice

  1 year ago

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• 07:29 thumb_up 57%

  JOI CBT Roleplay in Spanish. Extreme level. Have fun with your eggs.

  1 year ago

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• 11:09 thumb_up 83%

  Wife dresses her husband in her lingerie and then fucks him with her strap-on and plastic cock

  2 years ago

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• 08:12

  Jennas Suprise

  2 years ago

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  2 years ago

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• 19:14 thumb_up 17%

  He wants a strong PROSTATE ORGASM, so I make him cum with my STRAPON - UnlimitedOrgasm

  3 years ago

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  How to bring a guy to a double orgasm

  2 years ago

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  FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

  3 years ago

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• 03:06 thumb_up 89%

  8 INCH Strapon fucking my chastity slut in Latex

  3 years ago

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• 05:31

  Pussyfree Whiteboi Softcore Trainer 2 - subwhtboy33

  4 years ago

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• 22:42

  ANAL ACCELERATOR 2

  5 years ago

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  Smoking Mistress Turns you into a CUM slut

  4 years ago

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• 18:31

  Foot therapy to sissy training: Amateur, Handjob Chaturbate Porn

  1 month ago

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• 08:19

  Humiliating Strapon ATM with Mr Hankey’s Toys Rentman

  5 years ago

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• 14:35

  Firm and fast strap-on pegging marathon – sissy training highlights with MrsVictoria

  2 months ago

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• 20:51 thumb_up 14%

  Stop! Feminine sissies dont jerk off their cock - Sissy training and feminization with Lady Julina

  1 year ago

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• 12:57

  Dee Williams Natalie mars sissy training

  6 months ago

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• 06:07

  BBC sissy training

  5 years ago

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• 11:20 thumb_up 20%

  Sissy Training Session Part 3 - October 12.2023

  2 years ago

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• 10:28

  Mommy dom sissy training joi

  7 years ago

  JizzBunker

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• 13:04

  Sissy training with Femdom Mistress Tangent

  8 years ago

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• 06:07 thumb_up 67%

  BBC Sissy Training - Worship Big Black Cock

  7 years ago

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• 02:16

  Anal Stretching Training For V

  2 months ago

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• 05:05

  Miss Adrastea Sissy Training

  9 years ago

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• 08:22 thumb_up 17%

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  3 months ago

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• 16:18 thumb_up 11%

  School for Boys and Good Sissies Cock Whore Training

  8 months ago

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• 10:49

  Freshies Juice Box - Latex Sissy Maid Training

  5 months ago

  IcePorn

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• 12:26

  Innocent slave experiences ruined climax on day one of training

  11 months ago

  XXXVogue

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• 17:28

  Sissy bitches learn menstrual obedience from dominatrix lady Julina

  11 months ago

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• 19:13

  Sissy learns anal submission in high heels under femdom cuckolds command!

  11 months ago

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• 09:29

  Turning into a sissy with Mistress Lynette Phoenixs guidance

  11 months ago

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• 19:20

  Messy sissy gets mind-blowing ruined orgasms with tied up balls

  11 months ago

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• 06:31

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  11 months ago

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  Chastity cage sissy virginity guidance during Locktober!

  11 months ago

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• 05:13

  Korean femboy Seoara0909 undergoes sissy boy training and gets fucked hard

  11 months ago

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• 20:05 thumb_up 61%

  Non stop PEGGING gives me 7x ANAL ORGASM, I rewarded with 1 for her SISSY dick

  1 year ago

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• 10:37

  Selling your panties - submissive guys get anal training from a top dominatrix in sexy lingerie

  11 months ago

  XXXVogue

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• 08:14

  First Step for Virgin Sissy, vag Defloration. rectal Stretching, face-sitting, Humiliation, Pee. Mistress Arya Grander.

  1 year ago

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• 43:06

  First Step for Virgin Sissy, Cunt Defloration. Anal Stretching, Facesitting, Humiliation, Pee. Mistress Arya Grander.

  1 year ago

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