Sissy Training 279 videos

• 18:51 thumb_up 20%

  Chick motivates guy to undergo transformation into woman

  10 months ago

  XXXVogue

  sissy, pegging, strapon

  flag
• 46:22

  Musky Sweaty Ball Sack Addiction Mind Fuck Version

  1 year ago

  xHamster

  sissy

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• 15:23

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

  11 months ago

  XXXVogue

  sissy, pegging, train

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• 1:17:25

  POV Cuckold vol 25

  2 years ago

  xHamster

  facesitting, pegging

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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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• 19:45 thumb_up 33%

  Remote controlled with Lovense Toys from Domina Lady Julina

  2 years ago

  xHamster

  sissy, pantyhose

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• 25:06

  Dildo Hero - The holes are the plot

  5 years ago

  xHamster

  sissy

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• 59:25

  SissyPlay

  4 years ago

  xHamster

  sissy

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• 18:31

  Foot therapy to sissy training: Amateur, Handjob Chaturbate Porn

  2 weeks ago

  XXXDan

  mature, sissy, train, feet

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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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• 16:05

  Snow Bunny In Masked Black Warrior Fucks Petite Slut Cuckhold Sissy Training ( Bbc Worship )

  2 years ago

  HClips

  mask, sissy

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• 19:53 thumb_up 33%

  Amator - Lady Satori - Sissy Training Part 1

  5 years ago

  HClips

  sissy

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• 16:38

  Pov Femdom Sissy Training With Strap-on - Jessica Starling

  2 years ago

  HClips

  sissy

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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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• 15:49 thumb_up 33%

  The Ultimate Sissy Training by MissBratDom

  10 years ago

  xHamster

  train, sissy

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• 22:03 thumb_up 80%

  Mistress Zita - Sissy Slut Training

  9 months ago

  VipTube

  femdom, stockings, sissy

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• 20:36

  Custom sissy pegging with Clara Dee - dedicated to Fred

  10 months ago

  XXXVogue

  sissy, pegging

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• 17:08

  Mistress Jenna's Deep Anal Insertions for Sissy Butt Slut Tiffany

  10 months ago

  xHamster

  stockings, pegging, british, femdom, sissy, strapon

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• 16:03

  Booty training in the third installment

  10 months ago

  XXXVogue

  sissy, train

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• 17:28

  Sissy bitches learn menstrual obedience from dominatrix lady Julina

  10 months ago

  XXXVogue

  sissy

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• 19:20

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

  11 months ago

  XXXVogue

  sissy

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• 19:43

  Convincing him to become a sissy

  1 year ago

  xHamster

  train, sissy, femdom, nylon

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• 19:52

  Turning him into a sissy with seduction and femdom persuasion

  11 months ago

  XXXVogue

  sissy

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• 15:03

  Sissification FemDom POV flick: jaw-dropping milf dirty talk and humiliation (Arya Grander) training sissy

  2 years ago

  MatureClub

  sissy

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• 16:41

  Sissy "D" on the milking table - 2

  1 year ago

  xHamster

  sissy

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• 27:37

  Latex Strap-on SISSY FUCK point of view FEMDOM POV video - rubber Mistress dirty talk (Arya Grander)

  2 years ago

  xHamster

  rubber, swedish, sissy

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• 17:03

  Training My Sexy Sissy With 12 Inches Of Hard Dicks Hardcore Bondages Training

  3 years ago

  Upornia

  sissy, train

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• 19:03 thumb_up 60%

  A living Sextoy for 2 Ladies - Sissy Trainig

  3 years ago

  xHamster

  pegging, sissy, strapon

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• 29:11

  EROTIC AUDIO: Sunday, Sissy Sunday by MistressAzralynn

  3 years ago

  xHamster

  train, sissy

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• 17:27

  Sissy in Chastity gets fucked hard

  3 years ago

  xHamster

  train, crossdresser, sissy, chastity

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• 56:50 thumb_up 80%

  Dildo Hero - riding the A train

  5 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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• 15:37

  Jerk Off Instruction For Sissy Slut (Joi, blowjob)

  5 years ago

  xHamster

  instruction, sissy

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• 20:02

  I steaming up my lover’s rump in order to have fun with it

  8 months ago

  VideoSection

  strapon, bisexual, train, prostate, ass to mouth, domination, pegging

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• 18:43

  Femdom Ideas - Top 10 +

  3 months ago

  Beeg

  sissy, femdom, fetish, pegging

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• 16:07

  Step-mother demands her step-daughter to wear these sexy outfits

  11 months ago

  XXXVogue

  sissy, cougar

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• 15:30

  Playing Dress up with My Step Brother (slut Diaries Ep08)

  1 year ago

  xHamster

  handjob, pissing, sissy, femdom, nylon

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• 1:11:36

  Huge Horny Tits vol 8

  1 year ago

  xHamster

  JOI, femdom, cum in mouth, strapon, cuckold, wife

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• 25:11

  Double Homework - Episode 6 Gameplay by LoveSkySan69

  1 year ago

  xHamster

  mom, anime, japanese mom, sissy, japanese uncensored, cartoon

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• 16:55

  5 Days of Pegging - Day 1: Mistress Stretched His Ass, Pegged and Farted in His Face

  1 year ago

  xHamster

  ass, farting, femdom, pegging

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• 15:05

  The femdom nurse: the choice of the chastity cage

  1 year ago

  xHamster

  mom, cheating, femdom, chastity, cougar, sissy

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• 15:57

  Jax & Abbies little game, fighting for dominance and enjoying the struggle.

  3 years ago

  xHamster

  train, game, sissy

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• 19:43

  Spanish anal JOI. Top best anal positions.

  1 year ago

  xHamster

  pegging, sissy

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• 15:11

  She deserves anal

  3 years ago

  xHamster

  sissy

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• 17:42

  Easter Anal Game with Ovipositor Primal Hardwere Krubera

  3 years ago

  xHamster

  huge dildo, sissy

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• 1:21:19

  POV Cuckold volume 15

  3 years ago

  xHamster

  sissy, chastity

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• 37:52

  ANAL INSTRUCTING ASSGASM

  5 years ago

  xHamster

  train, instruction, sissy

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• 21:08

  Strap-on Pegging, rimjob & fucking

  3 years ago

  xHamster

  prostate, pegging, sissy

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• 16:59

  Pov Femdom Sissy Training with Strap-on

  5 months ago

  Beeg

  fetish, femdom, sissy, kinky, strapon

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• 36:02

  Trashy gamer fantasy with Blkfamlovin in sexy outfits and sissy training

  3 months ago

  XXXVogue

  fantasy, futanari, sissy

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• 19:39

  Sissy training

  7 months ago

  Beeg

  sissy

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• 44:41

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

  9 months ago

  JizzBunker

  facesitting, sissy, femdom

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• 40:24

  Hard Femdom Sissy Training, Cock Sounding, Anal Destruction, Strapon

  9 months ago

  JizzBunker

  strapon, sissy

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• 40:34

  Strict femdom sissy training with cock sounding, anal ravaging, and strap-on action

  10 months ago

  XXXVogue

  sissy

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• 22:01

  Fsu - Empty Headed Sissy Training

  9 months ago

  NuVid

  sissy

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• 40:24

  Hard Femdom SISSY TRAINING, Cock Sounding, Anal Destruction, Strapon

  12 months ago

  xHamster

  pegging, 18, romanian, sissy, femdom, dildo

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• 17:52

  Female dom point of view: sissy training flick: strap-on point of view and sissification by Mistress Arya Grander

  1 year ago

  HDSex

  strapon, husband, whore, sissy

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• 20:28

  Pro Sissy Training Level

  1 year ago

  SunPorno

  train

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• 15:17

  Sissy Training With A Gorgeous Dominatrix In Sexy Lingerie

  2 years ago

  HDZog

  sissy

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• 17:33

  Sissy Training Cock Rating And Panty Fetish

  1 year ago

  HClips

  sissy

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• 22:40

  Miss Jade – Sissy Training The Complete Series

  2 years ago

  IcePorn

  sissy

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• 23:45 thumb_up 14%

  Asmr Sissy Training Joi With Godesses

  2 years ago

  HClips

  JOI, sissy, ASMR, webcam

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• 16:31

  Joi Sissy Training Kit

  2 years ago

  HClips

  sissy, JOI

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• 25:59

  Sissy Training

  3 years ago

  Upornia

  sissy

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• 17:42

  FemDom POV: sissy training video: strap-on point of view and sissification by Mistress Arya Grander

  2 years ago

  xHamster

  train, swedish, sissy

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• 27:33

  Encasement Of My Sissy Cuck Husband Pegged, Stuffed, And Teased With Sex And Sissy Training Teaser

  3 years ago

  Upornia

  pegging, sissy

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• 15:22

  Amator - Lady Satori - Sissy Training Part 2

  5 years ago

  HClips

  sissy

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• 19:40

  Sissy Training

  4 years ago

  HClips

  sissy

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• 15:16

  Sissy Training W/ Smoking, Makeup & Strap On Cock Sucking Instruction

  8 years ago

  HClips

  train, instruction

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• 17:12

  Anal JOI Sissy training

  5 years ago

  HDZog

  train, sissy, teen anal (18+)

  flag
• 20:08

  Strapon latex sissy training

  9 years ago

  TXXX

  sissy

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• 1:27:33

  Sissy Training

  9 years ago

  xHamster

  sissy

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• 1:27:33

  Sissy training

  9 years ago

  TXXX

  train, sissy

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• 21:58

  Mistress sissy training

  11 years ago

  Upornia

  sissy

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• 27:09

  Sissy Training with Mistress V

  10 years ago

  xHamster

  train

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• 15:39

  MJ Sissy Slut Training: Anal, Cumshot Pov Porn

  2 weeks ago

  JizzBunker

  sissy

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• 23:19

  Mistress Zita - Sissy Slut Training

  9 months ago

  VipTube

  femdom, amateur, masturbation, toys, sissy

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• 16:24

  Milking in sissy mouth and pegging training

  9 months ago

  XXXDan

  german, femdom, pegging

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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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• 18:50 thumb_up 20%

  The ultimate femdom sissy transformation experience!

  10 months ago

  XXXVogue

  sissy

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• 15:53

  Femdom mistress takes charge of sissys anal training, leading to sissygasm

  10 months ago

  XXXVogue

  sissy

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• 19:53

  Submissive sissy gets anal training in Spanish

  11 months ago

  XXXVogue

  sissy, pegging

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• 19:13

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

  11 months ago

  XXXVogue

  sissy, bisexual

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• 18:51

  Sissy boy Adventures Collection 1

  11 months ago

  XXXVogue

  sissy

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• 15:05

  Vol. 2: Submissive sissys wild escapades

  11 months ago

  XXXVogue

  sissy

  flag
• 20:05 thumb_up 61%

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

  1 year ago

  xHamster

  femdom, latex, strapon, train, prostate, pegging, sissy

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• 23:54

  How Id fuck you Cd Sissy Hypno Anal Slut Training Hero Part

  1 year ago

  SunPorno

  chubby, cute, sissy

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• 30:40

  30 minute extrem ass training from Sissy D

  1 year ago

  XXXDan

  big ass, train, sissy

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• 15:21

  Hattabi4ik sissy femboy trap squirt orgasm self tear up super-hot big butt compilation

  1 year ago

  HDSex

  sissy, cumshot compilation, orgasm compilation

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• 27:47 thumb_up 20%

  Latex Strap-on SISSY poke point of look FEMDOM POV video - rubber domina dirty talk (Arya Grander)

  1 year ago

  MatureClub

  sissy, femdom, latex, BDSM, rubber

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• 24:04

  Becoming Sissy Sabrina and BJ POV CEI for Sissy Jenn

  1 year ago

  xHamster

  sissy

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• 17:38

  Dirty Mistress Can't Stop Gaping His Sissy Ass!

  2 years ago

  xHamster

  strapon, sissy

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• 20:19

  Sissy D Asshole Treatment Part 4 of 4

  2 years ago

  xHamster

  machine

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• 15:36

  Alexandra Marchenko – Sissy Whore Training

  2 years ago

  IcePorn

  sissy

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• 17:45

  Sissys Anal Training

  2 years ago

  HClips

  sissy

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• 28:50

  CatClaw – Sissy Slut Training

  2 years ago

  VipTube

  sissy

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• 15:02

  Sissification FemDom POV video: sexy MILF dirty talk and humiliation (Arya Grander) training sissy

  2 years ago

  xHamster

  train, swedish, sissy

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• 17:42

  Miss Veronica Steam – Sissy Needs To Be Trained

  2 years ago

  VipTube

  train, sissy

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• 22:00

  Lady Cherry train her sub to a sissy slut.

  2 years ago

  xHamster

  nylon, JOI, sissy

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• 24:12

  Sissy Chastity Training Bbc Cuckold

  2 years ago

  HClips

  sissy, chastity

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• 16:28

  Anal Training Instructional Video (not Porn) For Beginner Subs Sissies And Anal

  3 years ago

  ManySex

  instruction, sissy, train

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• 16:23

  Sissy Pony Whipping Training

  3 years ago

  TXXX

  pegging, sissy, spanking, femdom

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• 29:39 thumb_up 53%

  Sissy Hole Training

  3 years ago

  XXXDan

  sissy

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• 23:29

  Anal Training For Sissy Bitch

  3 years ago

  Upornia

  sissy

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• 16:05

  Sissy Strapon Training

  3 years ago

  TXXX

  strapon, train, sissy

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• 17:23

  Basic Sissy Ass Training

  3 years ago

  Upornia

  sissy, fisting

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• 22:44 thumb_up 25%

  Arya Grander Latex Rubber Backstage Video With Azeria Strap-on Sissy Fetish Bdsm Training

  4 years ago

  Upornia

  rubber, sissy, backstage

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• 57:30

  Abr Dgn Training Her Sissy

  4 years ago

  HDZog

  fetish, facesitting, sissy, femdom

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• 20:17

  Sissy Anal Trainer - Gina Valentina Roleplay

  5 years ago

  xHamster

  sissy

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• 20:47

  Deepthroat trainng - sissy shares helpful advice & tips

  4 years ago

  xHamster

  gagging, sissy

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• 19:44

  Sissy Anal Trainer - the Pornstar Roleplay

  5 years ago

  xHamster

  instruction, sissy

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• 39:18

  Slut training Sissy Deepthroat Kawai Wife

  5 years ago

  HClips

  train, sissy, wife

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• 16:35

  Intense Anal Training for submissive Sluts (Dildo Roleplay)

  5 years ago

  xHamster

  sissy

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• 15:39

  Mistress Sissy Hole Training

  6 years ago

  xHamster

  sissy

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• 30:56

  Sissy cocksucking slave training

  5 years ago

  TXXX

  sissy

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• 17:49

  Sissy bitch training

  7 years ago

  TXXX

  sissy

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• 21:40

  Mistress train her sissy

  9 years ago

  JizzBunker

  sissy

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• 20:28

  Sissy slut training

  7 years ago

  xHamster

  train, BBC, sissy

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• 21:39

  Mistress train her sissy

  10 years ago

  xHamster

  train, sissy

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• 21:40

  Mistress train her sissy

  10 years ago

  TXXX

  sissy

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