Sissy Training 1,903 videos

• 22:53 thumb_up 95%

  Mistress T In Sissy In Pink Gets Cock Trained

  4 years ago

  HClips

  femdom, strapon, sissy, webcam, stockings

  flag
• 06:01 thumb_up 93%

  Two dominant goddesses teach sissy hotties to suck and swallow

  2 years ago

  xHamster

  femdom, bisexual, czech, swallow, domination, sissy

  flag
• 11:04 thumb_up 92%

  Mistress Training Sissy

  3 years ago

  HClips

  strapon, pegging, sissy, train, femdom, german

  flag
• 06:39 thumb_up 91%

  Domina Liza - Sissy Maid Caning Training - Femdom

  2 years ago

  DrTuber

  femdom, spanking, sissy, maid

  flag
• 06:39 thumb_up 91%

  Advanced High Heel Training: The Treadmill Part One

  2 years ago

  xHamster

  latex, rubber, boots, leather, sissy

  flag
• 17:50 thumb_up 90%

  Sissy Femdom Compilation 2

  5 years ago

  xHamster

  crossdresser, swedish, sissy, strapon, pegging, bisexual

  flag
• 05:37 thumb_up 90%

  Double Punishment for the Sissy (a Classic)

  1 year ago

  xHamster

  femdom, bondage, sissy

  flag
• 20:16 thumb_up 90%

  High Class Sissy Trained - Mistress T

  4 years ago

  TXXX

  femdom, strapon, train, fetish, crossdresser, domination, sissy

  flag
• 03:06 thumb_up 89%

  8 INCH Strapon fucking my chastity slut in Latex

  3 years ago

  xHamster

  strapon, train, huge dildo, pegging, sissy, chastity

  flag
• 12:48 thumb_up 89%

  Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

  12 months ago

  xHamster

  femdom, french, doll, train, husband, sissy

  flag
• 11:23 thumb_up 89%

  Sissy Trained

  4 years ago

  HClips

  strapon, sissy, femdom, bisexual

  flag
• 18:17 thumb_up 89%

  Sissy Poppers Intox Training Mindfuck Mesmerise Femdom

  6 years ago

  HClips

  train, sissy

  flag
• 12:51 thumb_up 89%

  Mistress nikita training her sissy bf

  2 years ago

  XXXDan

  femdom, fetish, sissy

  flag
• 07:17 thumb_up 88%

  PEGGING - The first step to making him a sissy boy

  1 year ago

  xHamster

  desi, sissy, pegging, cuckold, bisexual

  flag
• 11:13 thumb_up 88%

  How to bring a guy to a double orgasm

  2 years ago

  xHamster

  prostate, massage, double anal, swedish, girlfriend, close up, sissy

  flag
• 10:37 thumb_up 88%

  PROSTATE ORGASM COMPILATION SISSY

  3 years ago

  xHamster

  femdom, prostate, orgasm compilation, sissy, kinky

  flag
• 04:15 thumb_up 88%

  ALL ABOUT COCK COMPILATION – BIG FAT JUICY DICK WORSHIP

  4 years ago

  xHamster

  prostate, swallow, handjob compilation, sissy

  flag
• 05:56 thumb_up 87%

  Teen Femdom Training And Pegging Her Sissy Maid

  3 years ago

  HClips

  femdom, strapon, train, maid, pegging, sissy

  flag
• 03:06 thumb_up 86%

  Sissy Training Cock Sucking

  3 years ago

  PornL

  sissy, handjob

  flag
• 06:05 thumb_up 86%

  Cum twice in a row from cock milking with prostate fingering

  1 year ago

  xHamster

  prostate, polish, sissy, gay, mom

  flag
• 02:37 thumb_up 86%

  CHASTITY SISSY SLUT ROUGH FUCKED by DominaFire

  3 years ago

  xHamster

  femdom, strapon, domination, chastity, bondage

  flag
• 05:35 thumb_up 86%

  A girl in black boots fucks a guy in a chastity belt hard

  3 years ago

  xHamster

  femdom, boots, sissy, chastity

  flag
• 08:12 thumb_up 86%

  Diaper Sissy Lesson: Chastity Peeing and Fisting

  2 years ago

  xHamster

  strapon, lactating, diaper, chastity, sissy

  flag
• 09:26 thumb_up 86%

  Maitresse Julia - When i Give a Long Footjob in Pantyhose and Socks ! Reward for my slave !

  2 years ago

  xHamster

  footjob, sissy, bondage

  flag
• 06:57 thumb_up 86%

  Sissy Boy In Training

  1 year ago

  HClips

  toys, femdom, BDSM, sissy

  flag
• 03:31 thumb_up 86%

  Big Boobs in Pantyhose Fucking a Chubby Hairy Pussy Milf

  3 years ago

  xHamster

  husband, sissy

  flag
• 26:14 thumb_up 85%

  Sissy training dreams

  7 years ago

  TXXX

  train, sissy, anal

  flag
• 01:17 thumb_up 85%

  Maximum anal punishment

  2 years ago

  xHamster

  latex, rubber, pegging, strapon, bondage, femdom

  flag
• 07:19 thumb_up 85%

  Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

  1 year ago

  xHamster

  femdom, train, whore, domination, pegging, slut, sissy

  flag
• 07:48 thumb_up 84%

  I locked up my husbands ball sack on the beach

  2 months ago

  XXXVogue

  femdom, train, beach, BDSM, husband, dirty talk, domination

  flag
• 02:18 thumb_up 84%

  MONSTER COCK PEGGING

  3 years ago

  xHamster

  femdom, strapon, pegging, sissy, german, monster

  flag
• 15:48 thumb_up 83%

  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

  flag
• 23:35 thumb_up 83%

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

  11 months ago

  xHamster

  train, diaper, pegging, enema, sissy, chastity

  flag
• 09:00 thumb_up 83%

  Get Off With A Real Femdom JOI

  9 months ago

  Analdin

  cuckold, feet, JOI, sissy, femdom

  flag
• 1:00:35 thumb_up 83%

  Facesitters in Heat Volume 3

  3 years ago

  xHamster

  sissy, squirt, facesitting, pegging, ass licking

  flag
• 07:19 thumb_up 83%

  Sissy Cuck neat internal cumshot After Wifes appointment

  1 year ago

  VideoSection

  train, wife, cuckold, facesitting, husband, cumshot, wife swap

  flag
• 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

  xHamster

  strapon, prostate, pegging, sissy, husband

  flag
• 01:32 thumb_up 83%

  Horny rubber doll gets stuffed - Mistress Tatjana

  2 years ago

  xHamster

  rubber, train, pegging, sissy

  flag
• 17:37 thumb_up 83%

  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

  flag
• 02:38 thumb_up 83%

  Cristal Kinky playing with my latex sissy doll Preview

  3 years ago

  xHamster

  rubber, doll, sissy, femdom

  flag
• 12:42 thumb_up 83%

  Long and Hard Pegging with a big dildo Topped Toys Mordax 90

  3 years ago

  xHamster

  strapon, pegging, sissy, german, huge dildo

  flag
• 06:40 thumb_up 83%

  Slut Training My Sissy Sluts Ass + Whipping

  2 years ago

  HClips

  femdom, rubber, strapon, pegging, sissy

  flag
• 08:50 thumb_up 82%

  Sexy Wife with Big Strapon pegging her Husband with Handjob

  12 months ago

  xHamster

  strapon, train, polish, domination, pegging, sissy

  flag
• 06:44 thumb_up 82%

  Hot Wife Kissing & Sucking Sissy Hard Clit Then Going Doggy

  3 years ago

  xHamster

  sissy, fat, saggy tits, femdom

  flag
• 01:56 thumb_up 82%

  A GangBang for the Sissy Slut

  5 years ago

  xHamster

  latex, strapon, gangbang, sissy, chastity

  flag
• 16:00 thumb_up 82%

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

  10 months ago

  XXXVogue

  chastity, sissy, femdom

  flag
• 07:59 thumb_up 82%

  Mistresst - High Class Sissy Trained

  4 years ago

  InPorn

  femdom, sissy, train

  flag
• 05:28 thumb_up 82%

  Chastity release and humiliating countdown ejaculation - Mistress Julia

  2 years ago

  xHamster

  pantyhose, femdom, french, sissy, chastity

  flag
• 10:28 thumb_up 81%

  Mistress enjoys sex with a chastity belt

  3 years ago

  xHamster

  strapon, prostate, CFNM, pegging, sissy, chastity

  flag
• 08:34 thumb_up 81%

  Bbw domina Fucks Sissy Slave Hard Strapon rectal

  3 months ago

  HDSex

  femdom, strapon, train, husband, whore, pegging, sissy

  flag
• 11:40 thumb_up 81%

  Tantaly : You Will Never fuck Me Again: abasing ejaculation on a Doll and Eternal Chastity - Mistress Julia

  8 months ago

  MatureClub

  pantyhose, femdom, small cock, doll, train, domination, sissy

  flag
• 08:50 thumb_up 81%

  Cum training my cock tease

  1 year ago

  xHamster

  bisexual, cuckold, crossdresser, pegging, sissy

  flag
• 07:36 thumb_up 81%

  Hottie blonde trains smooth boyfriend in hotel room

  2 years ago

  xHamster

  prostate, crossdresser, pegging, hotel, sissy

  flag
• 06:36 thumb_up 80%

  Domme Victoria Rey Collars, gags, abases, spits on her steamy chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

  11 months ago

  HDSex

  femdom, small cock, train, gagging, husband, panties, sissy

  flag
• 15:00 thumb_up 80%

  Alexis Amadahy And Jade Sissy Training And Strap On

  4 years ago

  Upornia

  train, sissy, femdom

  flag
• 07:39 thumb_up 80%

  Private pegging and anal play - submissive partners explore their kinky desires

  10 months ago

  XXXVogue

  sissy, bisexual, pegging, cuckold

  flag
• 09:30 thumb_up 80%

  Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

  2 years ago

  xHamster

  train, sissy, chastity, pantyhose, BDSM, cuckold

  flag
• 05:31 thumb_up 80%

  A stranger touches my breasts in a parking lot

  1 year ago

  xHamster

  train, sissy

  flag
• 11:53 thumb_up 80%

  Milking the first drops from my SISSY's PROSTATE

  1 year ago

  xHamster

  femdom, latex, train, prostate, milk, sissy, chastity

  flag
• 22:03 thumb_up 80%

  Mistress Zita - Sissy Slut Training

  9 months ago

  VipTube

  femdom, stockings, sissy

  flag
• 06:05 thumb_up 80%

  Tied up femboy twink milking and cumming like a whore

  2 years ago

  xHamster

  swedish, sissy, milk

  flag
• 07:02 thumb_up 80%

  Sissy Training Step 3of5

  6 years ago

  TXXX

  sissy

  flag
• 26:00 thumb_up 80%

  Mistress Trains Her With Sissy Slave

  3 years ago

  Upornia

  sissy, femdom

  flag
• 03:55 thumb_up 80%

  Rubbertoy gets completely immoblized and his dick trained

  1 year ago

  SexVidXXX

  sissy, latex, rubber

  flag
• 03:00 thumb_up 80%

  Sissy & Cuckold Training - SissySlutTraining

  5 years ago

  TXXX

  femdom, train, sissy, cuckold

  flag
• 02:33 thumb_up 80%

  Tease and Denial Orgasm Pantyhose Footjob ! Edging Control for this Sissy Maitresse Julia

  2 years ago

  xHamster

  footjob, nylon, sissy

  flag
• 02:16 thumb_up 80%

  DominaFire Anal Training her Sissy

  3 years ago

  xHamster

  train, sissy

  flag
• 07:17 thumb_up 80%

  My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

  1 year ago

  xHamster

  sissy, pissing, femdom

  flag
• 02:21 thumb_up 79%

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

  3 years ago

  xHamster

  strapon, prostate, pegging, sissy, chastity, BDSM

  flag
• 02:25 thumb_up 79%

  FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

  3 years ago

  xHamster

  latex, strapon, filipina, sissy, chastity

  flag
• 10:40 thumb_up 79%

  ASMR sloppy caged cuck chastity cum (locktober final reward)

  2 years ago

  xHamster

  femdom, sissy, chastity, ASMR, cuckold, mom

  flag
• 06:16 thumb_up 79%

  Feminization and Pegging of My Chastity Slave: Teaser Live Cam Replay: Mistress Julia

  1 year ago

  xHamster

  pantyhose, femdom, boots, heels, pegging, sissy, chastity

  flag
• 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

  flag
• 07:50 thumb_up 79%

  Married couple home pegging training

  1 year ago

  xHamster

  czech, BDSM, pegging, sissy

  flag
• 20:22 thumb_up 79%

  Sissy Enema And Anal Training

  1 year ago

  HClips

  strapon, train, BDSM, pegging, enema, sissy

  flag
• 06:05 thumb_up 79%

  So hot cumming after 7 days in chastity and anal training

  1 year ago

  xHamster

  femdom, bisexual, train, sissy, chastity

  flag
• 02:07 thumb_up 79%

  Latex Goddess Strapon Fucks Chastity Sissy

  2 years ago

  xHamster

  femdom, strapon, pegging, sissy, chastity, latex

  flag
• 02:43 thumb_up 79%

  SISSYSLUT PUNISHIMENT by DominaFire

  3 years ago

  xHamster

  femdom, spanking, sissy

  flag
• 11:53 thumb_up 78%

  My wife use me to clean her wet pee pussy. She discipline me and we ended having sex.

  2 years ago

  xHamster

  pissing, amateur, cuckold, dirty talk, sissy

  flag
• 14:09 thumb_up 78%

  Cum Addict, by Jlodalisque

  4 years ago

  xHamster

  instruction, compilation, sissy, cumshot compilation

  flag
• 21:24 thumb_up 78%

  Bisexual husband gets fucked by three strapons

  1 year ago

  xHamster

  bisexual, pegging, sissy

  flag
• 21:14 thumb_up 78%

  Pegging Training Deflower Husband

  3 years ago

  xHamster

  sissy, pegging, bisexual, italian

  flag
• 10:10 thumb_up 78%

  Training The Sissy

  10 years ago

  xHamster

  sissy, feet

  flag
• 07:00 thumb_up 78%

  BECOME THE TART (no Text)

  5 years ago

  TrannyGem

  train, slut, sissy

  flag
• 01:32 thumb_up 78%

  Gangbang the sissy slut - Part3

  2 years ago

  xHamster

  rubber, chastity, latex, bondage, strapon, sissy

  flag
• 01:21 thumb_up 78%

  Too big to strap on - Mistress Tatjana

  2 years ago

  xHamster

  femdom, rubber, fetish, sissy, chastity, latex

  flag
• 06:28 thumb_up 78%

  Sissy Trained and Humiliated by DominaFire

  2 years ago

  xHamster

  femdom

  flag
• 09:34 thumb_up 78%

  Sissy Whore

  4 years ago

  xHamster

  train, whore, sissy

  flag
• 14:33 thumb_up 77%

  Sissy cumslut training

  6 years ago

  TXXX

  train, sissy

  flag
• 17:46 thumb_up 77%

  Admission of being a Sissy - Mean girls

  3 years ago

  xHamster

  femdom, strapon, nurse, BDSM, gyno, exam, machine

  flag
• 12:52 thumb_up 77%

  I put him in Pink Panties and started Pegging him

  11 months ago

  xHamster

  pegging, sissy, chastity, german, femdom, anal

  flag
• 02:33 thumb_up 77%

  Sissy's Daily Service - Brianna Beach - Faphouse Preview

  3 years ago

  xHamster

  sissy

  flag
• 16:29 thumb_up 77%

  Intense pegging session with humiliation and extreme BDSM with Kinky Navlia

  10 months ago

  XXXVogue

  sissy, pegging, tied, leather, bondage, femdom

  flag
• 26:48 thumb_up 76%

  Sissy Slut - Left in the park as fucktoy

  3 years ago

  xHamster

  latex, sissy, public, femdom, strapon, bondage

  flag
• 01:38 thumb_up 76%

  The final transformation - Mistress Tatjana

  2 years ago

  xHamster

  femdom, rubber, strapon, chastity, bondage, sissy

  flag
• 16:20 thumb_up 76%

  Girl dominate sissy girls and fuck them

  1 year ago

  xHamster

  femdom, strapon, train, polish, spanking, leather, pegging

  flag
• 09:29 thumb_up 76%

  Mrs Loving Begins Sissy Training at Mother s Request

  9 years ago

  TXXX

  sissy, femdom, granny, mom

  flag
• 09:44 thumb_up 76%

  Sunday Humiliation for Sissy husband Full

  1 year ago

  xHamster

  handjob, femdom, train, cuckold, husband, sissy, chastity

  flag
• 05:50 thumb_up 75%

  I Will Make You Suck His Cock, Slave! You Must Please Me! Arya Grander

  1 year ago

  xHamster

  spandex, feet, bisexual

  flag
• 05:02 thumb_up 75%

  Doctors and their sissy slave in a wild electroplay session

  4 months ago

  XXXVogue

  femdom, train, doctor, gloves, BDSM, electro, sissy

  flag
• 01:46 thumb_up 75%

  Mistress Mommy Spanks Round Sissy Ass

  5 years ago

  xHamster

  crossdresser, sissy, pantyhose, femdom

  flag
• 11:41 thumb_up 75%

  JOI CEI Domination Session With Mistress

  9 months ago

  Analdin

  femdom, JOI, sissy

  flag
• 16:37 thumb_up 75%

  German domina and slave crossdresser in BDSM session

  2 years ago

  xHamster

  crossdresser, german, femdom

  flag
• 14:05 thumb_up 75%

  Femdom Pegging Latex Sissy by Dominafire

  1 year ago

  xHamster

  femdom, latex, strapon, pegging, sissy, chastity

  flag
• 11:12 thumb_up 75%

  A cock for sissies (training with mistress)

  5 years ago

  TXXX

  sissy, femdom

  flag
• 01:44 thumb_up 75%

  Sorry no release but an ass fuck

  2 years ago

  xHamster

  rubber, strapon, sissy, chastity, latex

  flag
• 03:49 thumb_up 75%

  EDGING & SOUNDING by Sadistic Nurse DominaFire

  3 years ago

  xHamster

  train, gloves, exam, sissy, nurse

  flag
• 15:20 thumb_up 75%

  Mrs Loving Begins Sissy Training at Mother s Request

  9 years ago

  TXXX

  femdom, train, sissy, granny

  flag
• 02:16 thumb_up 74%

  Latex Asian Dominatrix Pegging her Chastity Sissy with Huge Strapon

  3 years ago

  xHamster

  latex, sissy, chastity, pegging, BDSM, german

  flag
• 15:24 thumb_up 74%

  Genitalia haircut & edging for innocence marionette

  5 months ago

  HDSex

  train, prostate, BDSM, husband, whore, shaving, toys

  flag
• 17:12 thumb_up 74%

  Sissy anal step by step training

  6 years ago

  JizzBunker

  train, sissy

  flag
• 21:06 thumb_up 74%

  RUINED TWICE!!! Post Orgasm Handjob

  3 years ago

  xHamster

  pantyhose, nylon, sissy, french, BDSM

  flag
• 15:16 thumb_up 74%

  Sissy training

  6 years ago

  TXXX

  bisexual, sissy

  flag
• 05:58 thumb_up 73%

  The bondage and feminization of a slave by a blonde queen

  1 year ago

  xHamster

  strapon, bondage, BDSM, pegging, sissy, femdom

  flag
• 12:23 thumb_up 73%

  MISTRESS LORRAINE TRAINING HER SISSY (COMPLETE MOVIE)

  2 years ago

  VipTube

  femdom, sissy

  flag
• 09:20 thumb_up 73%

  Maitresse Julia - What right to a slave who is no longer useful ? My smells! Humiliation !

  3 years ago

  xHamster

  domination, sissy, pantyhose

  flag
• 12:28 thumb_up 73%

  Sasha De Sade Sissy Inspection Hot!

  6 years ago

  TrannyGem

  femdom, train, bondage, crossdresser, sissy, BDSM

  flag
• 04:51 thumb_up 72%

  Training Sissy To Be A Good Whore For Her B.f

  2 years ago

  HClips

  sissy, amateur

  flag
• 01:57 thumb_up 72%

  Sissy would not swallow

  5 years ago

  xHamster

  bisexual, sissy, chastity, BDSM, femdom

  flag
• 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

  flag

Popular categories

Other free porn sites