Sissy Training 279 videos

• 17:37 thumb_up 84%

  Gentle guts mcabooseage and pegging of the male ass. He came in a entire puddle

  8 months ago

  MatureClub

  bisexual, train, prostate, massage, domination, pegging, sissy

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• 23:09 thumb_up 66%

  Sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

  1 year ago

  xHamster

  femdom, pegging, sissy, cuckold, fetish

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• 50:56 thumb_up 67%

  Becky Scolds Sissy bi-atch Michel for Not Cleaning the Kitchen decently

  1 year ago

  VideoSection

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• 16:29 thumb_up 76%

  Intense pegging session with humiliation and extreme BDSM with Kinky Navlia

  10 months ago

  XXXVogue

  sissy, pegging, tied, leather, bondage, femdom

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• 36:32 thumb_up 65%

  Inexperienced pegs and fists his tight asshole

  11 months ago

  XXXVogue

  strapon, gloves, pegging, sissy, mature

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• 20:16 thumb_up 90%

  High Class Sissy Trained - Mistress T

  4 years ago

  TXXX

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• 55:00 thumb_up 79%

  Prostate Milking Anal Training Pspot Orgasm - INSTITUTION X - COMPILATION 1 - 2

  3 years ago

  xHamster

  femdom, strapon, train, prostate, BDSM, milk, handjob compilation

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• 15:29 thumb_up 59%

  Blindfolded sissy slut training

  1 year ago

  xHamster

  bisexual, train, sissy, blindfolded

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• 1:28:40 thumb_up 65%

  Kinky Carmen In Sissy Bitch Training By

  3 years ago

  TXXX

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• 19:41 thumb_up 67%

  Sissy Training - Sucking That Dick and Swallow the Load

  6 years ago

  Analdin

  sissy, teen (18+), swallow, train, amateur

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• 15:24 thumb_up 72%

  Genitalia haircut & edging for innocence marionette

  5 months ago

  HDSex

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• 47:59 thumb_up 61%

  Sissy Maid Cleaning for 2 Warm Dominatrixes

  5 years ago

  TrannyGem

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• 15:20 thumb_up 75%

  Mrs Loving Begins Sissy Training at Mother s Request

  9 years ago

  TXXX

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• 15:20 thumb_up 60%

  Sissy training

  6 years ago

  xHamster

  bisexual, train, sissy

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• 32:55 thumb_up 51%

  Girlcock Hypnosis Pt.7: 555 Foxy Babes (and their cocks!)

  4 years ago

  xHamster

  train, pool, lingerie, babe, futanari, sissy, softcore

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• 19:38

  No mercy prostate wanking and passionate painal pegging. ( camera shut down, no concluding :( )

  3 days ago

  VideoSection

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• 17:24 thumb_up 69%

  Mistress Turns out her Slave for Face Fucking, Ass Play, and Facials

  6 years ago

  TrannyGem

  femdom, train, fetish, sissy, amateur, blowjob

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• 16:00 thumb_up 86%

  Cuckolds shame - sissy gets trained in chastity by femdom mistress in high heels

  10 months ago

  XXXVogue

  chastity, sissy, femdom

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• 21:14 thumb_up 73%

  Pegging Training Deflower Husband

  3 years ago

  xHamster

  sissy, pegging, bisexual, italian

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• 17:50 thumb_up 91%

  Sissy Femdom Compilation 2

  5 years ago

  xHamster

  crossdresser, swedish, sissy, strapon, pegging, bisexual

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• 1:10:38 thumb_up 67%

  Sissy Training Day

  3 years ago

  TXXX

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• 17:11 thumb_up 52%

  CUM HUNGRY

  4 years ago

  xHamster

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• 18:37 thumb_up 69%

  Sissy Cock Training

  4 years ago

  xHamster

  sissy, beauty

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• 27:59 thumb_up 63%

  Pegging His Tight Asshole with Large Dildo - Strapon & Ass Fisting & Cum

  1 year ago

  xHamster

  fisting, pegging, sissy, french, strapon

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• 23:17

  Mistress Lizbeth takes back whats hers with some intense femdom action

  1 week ago

  XXXVogue

  strapon, train, whore, domination, pegging, sissy

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• 23:35 thumb_up 83%

  Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

  11 months ago

  xHamster

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• 15:52 thumb_up 53%

  Homewrecking Mistress Domination JOI

  3 years ago

  Analdin

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• 16:20 thumb_up 76%

  Girl dominate sissy girls and fuck them

  1 year ago

  xHamster

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• 17:46 thumb_up 77%

  Admission of being a Sissy - Mean girls

  3 years ago

  xHamster

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• 17:11 thumb_up 45%

  Dominatrix Mistress April - Rose Garden Part one

  3 years ago

  xHamster

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• 16:40

  Femdom with Hottest Dominant Whore Kendra Hart

  2 months ago

  Analdin

  pantyhose, femdom, train, facesitting, crossdresser, whore, domination

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• 17:42 thumb_up 60%

  Sissy Wife's First Anal JOI - Clara Dee JOI

  2 years ago

  xHamster

  instruction, sissy

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• 20:48 thumb_up 43%

  Sissygasm Tutorial - Sissification with the Lady of Feminization

  2 years ago

  xHamster

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• 16:37 thumb_up 77%

  German domina and slave crossdresser in BDSM session

  2 years ago

  xHamster

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• 15:48 thumb_up 75%

  Your sissy cunt will be fucked today with my huge strapon - Sissification & Feminization with Lady Julina

  2 years ago

  xHamster

  spandex, leather, heels, lipstick, sissy, leggings

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• 17:35 thumb_up 59%

  Moan for me my sissy bitch - sissification with collar, anal plugs and rubber pussy

  3 years ago

  xHamster

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• 18:02 thumb_up 73%

  Sissy Training Level 7

  5 years ago

  xHamster

  train, sissy

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• 21:24 thumb_up 70%

  Bisexual husband gets fucked by three strapons

  1 year ago

  xHamster

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• 22:43 thumb_up 60%

  I destroy my husband's ass

  2 years ago

  xHamster

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• 20:24 thumb_up 48%

  POV Sissy Pegging - Custom for FRED

  4 years ago

  xHamster

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• 16:15 thumb_up 67%

  Comeback of the Slut

  1 year ago

  xHamster

  strapon, squirt, fisting, cougar, sissy

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• 23:36

  Top 10 Sissy Ideas 2023 (pegging, donk speculums, urinate, Chastity, Diapers, Enema)

  1 year ago

  VideoSection

  train, diaper, pegging, enema, sissy, chastity

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• 1:00:53 thumb_up 11%

  Sissy fag hypno lesson: how to be a soft sweet girl

  2 years ago

  xHamster

  sissy, femdom

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• 18:40

  Femdom sissy feminization!

  3 years ago

  xHamster

  sissy

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• 23:58 thumb_up 62%

  Sissy Maid female dominance Pegging Compilation

  1 year ago

  VideoSection

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• 22:53 thumb_up 96%

  Mistress T In Sissy In Pink Gets Cock Trained

  4 years ago

  HClips

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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

  xHamster

  crossdresser, sissy, chastity, natural

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• 16:21 thumb_up 72%

  The evolution of the size of a chastity cage cock

  1 year ago

  xHamster

  train, husband, dirty talk, sissy, chastity, story

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• 17:52

  Heat of Warmed Body - Whipping by Lady Wolf and Goddess Valkyrie

  2 years ago

  xHamster

  sissy, femdom

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• 15:37 thumb_up 69%

  Spanking punishment from a nun

  2 years ago

  xHamster

  spanking, nun, femdom, sissy, BDSM, homemade

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• 20:17 thumb_up 33%

  Spanking, Sucking and Milking My Slave

  3 years ago

  xHamster

  milk, pump, sissy, femdom

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• 26:14 thumb_up 85%

  Sissy training dreams

  7 years ago

  TXXX

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• 1:09:11 thumb_up 62%

  POV Cuckold volume 3

  4 years ago

  xHamster

  train, facesitting, creampie compilation, sissy, chastity, cuckold

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• 38:10

  My owner becomes my SIssy

  2 years ago

  xHamster

  femdom, strapon, boots, sissy

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• 19:35 thumb_up 50%

  Mistress was merciful and feminized sissy in chastity cage got his ruined orgasms

  8 months ago

  xHamster

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• 22:43 thumb_up 50%

  Sissy Cuckold Training

  3 years ago

  TXXX

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• 21:06 thumb_up 74%

  RUINED TWICE!!! Post Orgasm Handjob

  3 years ago

  xHamster

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• 24:04

  CEI deep-throat Your jizz Down JOI by princess Chy Latte

  5 months ago

  HDSex

  ebony

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• 17:04 thumb_up 70%

  Horny Sissy Caption Story – Quarantined With Black Friend!

  5 years ago

  xHamster

  sissy, story, black, mature anal

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• 30:40 thumb_up 50%

  30 minute extrem ass training from Sissy "D"

  1 year ago

  xHamster

  bondage, sissy, german

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• 15:49

  Wife Swap Strapon Slave Husband

  2 years ago

  xHamster

  wife swap, pegging, sissy, bondage

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• 16:50 thumb_up 71%

  Mistress dominates her sissyboy with pegging and sissy training, transforming him into her obedient slut

  10 months ago

  XXXVogue

  sissy, pegging, strapon

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• 44:42 thumb_up 60%

  Newbie sissy training with Arya Grander: stretching her sissy snatch with fingers and indulging in face-sitting and pussy worship

  5 months ago

  XXXVogue

  femdom, train, big ass, gloves, facesitting, sissy, granny anal

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• 43:57 thumb_up 70%

  The installation of the rubber doll - Sissy Training

  3 years ago

  xHamster

  femdom, latex, rubber, doll, train, leather, sissy

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• 15:18

  Pimping You Out - Miss Faith Rae's Femdom POV Sissy Training Findom Debt Contract - HD 1080p MP4

  1 year ago

  xHamster

  instruction, JOI, femdom, domination

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• 30:51 thumb_up 68%

  Sissy Slut - Outdoor Domination

  3 years ago

  xHamster

  femdom, latex, strapon, train, sissy

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• 23:55

  ASMR Sissy Training JOI With Godesses

  3 months ago

  Analdin

  JOI, fetish, femdom, cuckold, ASMR, sissy

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• 25:44 thumb_up 60%

  Best black cocks ever comp

  5 years ago

  xHamster

  train, sissy

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• 16:13 thumb_up 57%

  Become a sexy sissy girl of german dominatrix

  3 years ago

  xHamster

  sissy, spanking

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• 23:09 thumb_up 45%

  Sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

  10 months ago

  XXXDan

  femdom, strapon, train, husband, sissy

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• 27:14

  Sweet sissy ass tries two strapon cocks

  1 year ago

  xHamster

  pegging, sissy

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• 29:17 thumb_up 71%

  Sissy Caption Story: 1 Month

  4 years ago

  xHamster

  sissy, swallow, slut, cumshot compilation

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• 50:10

  Deeper. Anal hypno training

  2 years ago

  xHamster

  prostate, sissy

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• 18:17 thumb_up 89%

  Sissy Poppers Intox Training Mindfuck Mesmerise Femdom

  6 years ago

  HClips

  train, sissy

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• 19:38

  Smoker makes you a sissy

  5 years ago

  xHamster

  sissy

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• 16:30 thumb_up 57%

  Sissy training

  3 months ago

  JizzBunker

  sissy

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• 19:26 thumb_up 67%

  SISSY TRAINING...EAT YOUR OWN CUM

  1 year ago

  SunPorno

  train, sissy, kissing, masturbation

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• 44:41

  Newbie Sissy Training: Meeting #2. Stretching Sissy Cunt with Fingers. Facesitting. Pussy Worship. Arya Grander

  9 months ago

  xHamster

  train, sissy, femdom, big ass, facesitting

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• 1:00:35 thumb_up 83%

  Facesitters in Heat Volume 3

  3 years ago

  xHamster

  sissy, squirt, facesitting, pegging, ass licking

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• 26:48 thumb_up 76%

  Sissy Slut - Left in the park as fucktoy

  3 years ago

  xHamster

  latex, sissy, public, femdom, strapon, bondage

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• 47:04 thumb_up 67%

  Dildo game day 1 part 2 Job interview

  4 years ago

  xHamster

  train, JOI, sissy

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• 26:08 thumb_up 40%

  Disobedient muscle fuckslut dominated and punished with intense anal training. Submission is now the norm in this femdom-led relationship

  10 months ago

  XXXVogue

  sissy, pegging, muscle

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• 16:18 thumb_up 11%

  School for Boys and Good Sissies Cock Whore Training

  7 months ago

  Beeg

  sissy, pantyhose, whore, redhead, femdom

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• 43:06

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

  1 year ago

  xHamster

  leggings, femdom, train, facesitting, sissy

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• 19:52

  Turning him into a sissy with seduction and femdom persuasion

  10 months ago

  XXXVogue

  sissy

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• 20:22 thumb_up 79%

  Sissy Enema And Anal Training

  1 year ago

  HClips

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• 17:12 thumb_up 74%

  Sissy anal step by step training

  6 years ago

  JizzBunker

  train, sissy

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• 15:33

  Make your SISSY fantasies come true

  2 years ago

  xHamster

  crossdresser, futanari, sissy

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• 22:35

  Weekend Wreckage 2 - Hardcore brutal domination: She destroys him with fists, massive dick, and baseball bat

  10 months ago

  XXXVogue

  sissy, pegging, huge dildo, femdom

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• 18:51 thumb_up 20%

  Chick motivates guy to undergo transformation into woman

  10 months ago

  XXXVogue

  sissy, pegging, strapon

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• 18:51 thumb_up 33%

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

  10 months ago

  XXXVogue

  sissy, pegging, lipstick, cuckold, lesbian

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• 21:55

  What is your kink? - Experience classic dominance, feminization, aroma and extreme fetishes with Domina Lady Julina

  2 years ago

  xHamster

  boots, leather, sissy, BDSM, pegging, classic

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• 1:08:00 thumb_up 17%

  POV Cuckold vol 39

  12 months ago

  xHamster

  train, facesitting, husband, pegging, sissy, american, chastity

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• 17:05 thumb_up 60%

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

  5 years ago

  xHamster

  big clit, sissy

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• 1:20:50 thumb_up 72%

  I made him my slut and fucked his ass

  3 years ago

  xHamster

  prostate, czech, ass licking, sissy, bisexual, kinky

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• 18:31

  Foot therapy to sissy training: Amateur, Handjob Chaturbate Porn

  1 week ago

  XXXDan

  mature, sissy, train, feet

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• 17:28

  BrookelynneBriar Sissy Wife Training CFNM Part

  3 weeks ago

  VipTube

  CFNM, strapon, femdom

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• 15:16 thumb_up 70%

  Sissy training

  6 years ago

  TXXX

  bisexual, sissy

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• 29:00

  Talishas Sissy Anal Trainer

  4 years ago

  xHamster

  instruction, sissy

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• 17:27

  Sissy in Chastity gets fucked hard

  3 years ago

  xHamster

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• 56:50 thumb_up 80%

  Dildo Hero - riding the A train

  4 years ago

  xHamster

  sissy

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• 17:14

  Cocksucking Training for Females and Sissies

  5 years ago

  Upornia

  train, sissy

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• 19:44

  Sissy Anal Trainer - the Pornstar Roleplay

  5 years ago

  xHamster

  sissy

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• 15:23

  Susie the strap-on dildo mega-slut dominated by Mistress Kiana

  10 months ago

  XXXVogue

  sissy, pegging, train

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• 26:49

  Strapon Training Is Just the Beginning... Smoking Fetish Sissy Cocklust

  6 years ago

  TXXX

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• 20:38

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

  1 year ago

  xHamster

  train, dirty talk, JOI, sissy

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• 20:38 thumb_up 44%

  Multiple clips of messy cumshots. Beware. A lot of cum and spit.

  6 years ago

  XoZilla

  sissy, spit

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• 25:06

  Dildo Hero - The holes are the plot

  4 years ago

  xHamster

  sissy

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• 15:49 thumb_up 53%

  Sissy Training Session Part 2 - October 12.2023

  2 years ago

  xHamster

  sissy, machine, tied, bondage

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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

  XXXDan

  sissy, BDSM, crossdresser, german

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• 1:01:11 thumb_up 64%

  Sissy Training and Devotion

  4 years ago

  xHamster

  train, sissy, femdom

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• 20:15 thumb_up 40%

  Pounding non-stop for 7 anal climaxes during pegging session, rewarded with sissy treatment

  10 months ago

  XXXVogue

  sissy, pegging, latex, strapon, femdom, prostate

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• 15:49 thumb_up 33%

  The Ultimate Sissy Training by MissBratDom

  10 years ago

  xHamster

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• 1:03:10

  Sissy lesson: how to be a good slut

  2 years ago

  xHamster

  sissy, pegging, bondage

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• 17:12 thumb_up 29%

  You Will Be Wearing a Headscarf Today Sissy Kelly

  1 year ago

  xHamster

  lipstick, sissy

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• 1:41:05 thumb_up 70%

  German Mastix Silvia trains her sissy maid

  12 years ago

  TXXX

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• 21:33

  Gentle prostate rubdown and facesitting in thankfulness. I came on his face and he came in my mitt and

  8 months ago

  VideoSection

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• 20:48

  Mean Girls Joi

  5 months ago

  Beeg

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• 40:31

  Dildo game day 1 part 1 my little helper

  4 years ago

  xHamster

  instruction, game, sissy

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• 59:25

  SissyPlay

  4 years ago

  xHamster

  sissy

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