SHEMALE • SISSY TRAINING 700 videos

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31:01 75%

Dutch, femboy anal, used hard

1 month ago

XXXVogue

amateur, public, blowjob, train, outdoor, dildo, crossdresser
29:44 58%

Mature, crossdressing, amateur

3 weeks ago

XXXVogue

mature, french, blowjob, train, party, BDSM, crossdresser
17:13 53%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

9 months ago

TrannyGem

teen (18+), train, crossdresser, british, 18, whore, slut
23:38 25%

Sissy Maid Gets Locked in bondage and Chastity to Be Fucked by Her romp dame

3 weeks ago

ShemaleMovie

amateur, small cock, bondage, maid, lingerie, BDSM, crossdresser
39:26 77%

Petra the hard-core ass-fuck cockslut (incl dap tap fist en huge dildo)

3 months ago

ShemaleTaxi

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15:07 57%

BBC plays with caged sissy queen Christinewest120

3 months ago

XXXVogue

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22:45 81%

Amateur Couple and Trans - Train

1 year ago

xHamster

teen (18+), train, threesome, couple, teen anal (18+), sissy
28:06 59%

SADISM & MASOCHISM Sissy fellate instructing with clyster!

8 months ago

TrannyGem

stockings, shemale, blowjob, train, instruction, fetish, bondage
34:54 88%

Gorgeous tgirl Angel dildo training

1 year ago

AShemaleTube

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42:54 47%

My Path to Life as A Sissy Hoe

6 years ago

TrannyGem

train, whore, sissy, compilation, threesome
18:28 79%

GOOD-SIZED Belt Dick Pegging for V-Card Sissy Victim Demolishing her Trampy Crevice by Domina Mercer

4 years ago

TrannyGem

femdom, strapon, lesbian, train, bondage, dildo, crossdresser
15:04 70%

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

4 years ago

TrannyGem

mature, femdom, mature anal, train, granny, british, dirty talk
15:35 68%

Sissy Hypno #2: Becoming A Cock Slut

5 years ago

xHamster

train, sissy, creampie
22:45

Dame Alice Compilation 07 mesmerizing Beautiful (mesmerize Version) sight Originals by Subscription 4K Uhd 60 Fps HDR

1 week ago

ShemaleTaxi

latex, crossdresser, compilation, pissing, amateur, pantyhose, gangbang
20:08

Crossdresser compilation, hot sexy shemale, crossdresser femdom

1 week ago

XXXVogue

indian, femdom, strapon, bondage, maid, BDSM, crossdresser
1:02:22 68%

Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5

1 year ago

xHamster

train, anal, crossdresser, dutch, bareback, skinny, sissy
31:08

Is Sissy well-prepped for the giant Game

2 weeks ago

ShemaleMovie

sissy, shemale, POV
18:28 67%

Humungous strapon Pegging with Bad Dragon and Hankey for whorey Sissy Whore by Mistress Mercer

1 month ago

VideoSection

femdom, shemale, strapon, train, BDSM, whore, pegging
54:11 33%

Hd videos, her bitch, french trans

3 weeks ago

XXXVogue

amateur, french, train, ladyboy, crossdresser, facial, prostitute
28:06 92%

Ryu Nymph Stretches her Arse with a Monster can

4 years ago

TrannyGem

train, boots, big tits, monster, ass, insertion, toys
27:39 78%

Trained to Be a Good Slut

11 months ago

$$ FapHouse

train, couple, lingerie, tattoo, facial, heels, bareback
27:04

Actual Training at the Sissy Institute

2 months ago

$$ FapHouse

bondage, sissy, shemale, BDSM, masturbation, dildo
19:58 83%

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

5 years ago

ShemaleZ

handjob, femdom, latex, train, fetish, crossdresser, domination
20:49 90%

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

4 years ago

TrannyGem

femdom, latex, strapon, bisexual, train, bondage, BDSM
17:07 63%

Step-Mom instruct a significant lesson to her fresh step daughter-in-law (How to be a tramp)

2 years ago

TrannyGem

mom, fat, instruction, facesitting, shemale and girl, stepmom, domination
17:09 57%

Feminization - Sissification - Sissy instructing - Sissy Support - full version

1 year ago

ShemaleMovie

POV, train, instruction, 18, full movie, BBC, sissy
1:27:33 66%

Sissy in Training

6 years ago

xHamster

train, domination, sissy
20:46

Natacha superslut from Lyon dual anal invasion

1 week ago

ShemaleTaxi

prostitute, shemale, french, sissy, femboy
21:15 83%

Sissy Training With Bailey Love

3 years ago

HClips

shemale, train, sissy, amateur
15:39 94%

Whife *

6 years ago

TrannyGem

train, anal, bondage, ladyboy, crossdresser, cumshot, babe
17:18 40%

Natacha slut from Lyon romped like a breezy

1 month ago

ShemaleMovie

french, shemale, crossdresser, sissy, BDSM
20:59 50%

White Sissy Virginity Instructing (Smash Machine)

7 months ago

TrannyGem

femdom, teen (18+), POV, instruction, fetish, teen anal (18+), bondage
20:41 70%

Sissy Poppers Hypnose training IV

5 years ago

ShemaleTaxi

train, sissy, shemale
20:10 73%

Ass fucking Update two: queen Edition!

11 months ago

ShemaleMovie

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27:03 78%

Playtime 69

3 months ago

ShemaleTaxi

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58:16 72%

Young goth femboy anal training

1 year ago

AShemaleTube

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17:41 76%

Sissy Pussy Training

5 years ago

xHamster

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18:22 67%

Sissy breezy Is What u Will Always Be

5 years ago

TrannyGem

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22:39 80%

Sissy Crossdresser - Amateur Couple And Trans - Train

1 year ago

ShemaleZ

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24:19 62%

Step mummy drills son-in-law culo and train jizm while being drilled

9 months ago

TrannyGem

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1:02:24 65%

Stunning Tgirl shoots a pile of jism while getting fucked bare on date #5

1 year ago

ShemaleTaxi

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15:05 33%

Wooly Fuckpole Adore - BrainWash Jerk Off Instructions

7 months ago

TrannyGem

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17:32 60%

Sissy bbc training Encouragement Crossdresser bi-racial Fiona Fortune

6 months ago

HDSex

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21:13 83%

Teen t-girl College Fuck Anal SEX TRANS dame finishes off trans porn

6 months ago

ShemaleTaxi

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20:51 77%

Turning the staright dudes homo

4 years ago

TrannyGem

mature, femdom, train, british, sissy
17:44 91%

Extraordinary Sissy Bad Dragon Gaping and FemDom Hole Destruction with Speculum flash Off by mistress Mercer

5 months ago

ShemaleMovie

femdom, shemale, strapon, train, anal, flashing, BDSM
25:17 83%

Sissy Fuckdoll Delivery

5 years ago

TrannyGem

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15:15

Sissy Kate learns how to use the assfuck fuckin machine with Lisa

1 month ago

ShemaleMovie

stockings, dildo, BDSM, crossdresser, riding, heels, machine
26:34 88%

Sissy Institute Mistress Bailey Trains SISSYSLUTS - Lily DeMure + Nyxi Leon

5 years ago

BeMyHole

femdom, train, sissy
17:29 89%

TS Schoolgirl Sasha Helps you Learn about Shemale Anatomy

7 years ago

TrannyGem

train, instruction, british, dirty talk, small tits, JOI, sissy
16:32 87%

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

5 years ago

TrannyGem

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20:21 80%

Forced By Step Mommy Sissy Enema And Anal Training

2 years ago

ShemaleZ

mom, sissy, stockings, train
20:59 65%

Breezy Teaching Jizz Slurping two

4 years ago

TrannyGem

train, swallow, riding, JOI, sissy
23:19 81%

Sissy Trained And Owned By BIG BLACK PENIS Bull

4 years ago

Analdin

train, anal, BDSM, deepthroat, penis, BBC, sissy
39:51

Sissy vibrator, anal masturbation, hd videos

3 weeks ago

XXXVogue

small cock, train, lingerie, crossdresser, masturbation, machine, vibrator
21:05

Lil Demon Humped a Transgirl Angel rock-hard in the CABOOSE

4 years ago

TrannyGem

femdom, strapon, train, dress, slut, sissy
41:04 50%

Your friends futa mommy takes control of your backside during the sleepover

6 months ago

XXXVogue

dildo, futanari, sissy, mom, shemale, train
18:30 69%

Just because I can..

8 months ago

ShemaleTaxi

latex, bondage, BDSM, crossdresser, heels, sissy
19:44

Whore training, holes, fucking machine

2 weeks ago

XXXVogue

shemale, amateur, sissy, machine
20:08

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1 month ago

VideoSection

cute, emo, train, anal, game, masturbation, goth
28:27 71%

TPP Sissy hypnosis

9 months ago

ShemaleMovie

sissy, compilation, cumshot compilation, big cock, cumshot
19:52 66%

Feminizaton - Sissy Instructing - COSMIC SISSY FATE

1 year ago

TrannyGem

instruction, compilation, dirty talk, cumshot compilation, JOI, BBC
25:04 88%

Dizzy In demeaning Sissy Maid teaching!

1 year ago

ShemaleMovie

strapon, train, bondage, maid, dildo, BDSM, domination
1:24:42 75%

PetraTVsletje training 02, romped by a meaty fuckpole and abused with some big toys

1 year ago

VideoSection

homemade, bisexual, train, BDSM, toys, domination, bareback
40:47

Shemale porn, french trans, the big dick bitch

3 weeks ago

XXXVogue

shemale, french, train, BDSM, facial, prostitute, big cock
26:38 78%

Trained to Be Completely Subservient to Him

11 months ago

$$ FapHouse

black, train, interracial, bareback, sissy, hardcore
20:52 84%

Lindsey Training Her Sissy Slave

1 year ago

AShemaleTube

blowjob, creampie, train, lingerie, crossdresser, big cock, domination
18:38

Sissy mega-bitch Kandi Dance Music movie

5 days ago

ShemaleTaxi

BBC, compilation, BDSM, public, gangbang, big cock, creampie
47:11

Solo, solo handjob, sissy nylon

5 days ago

XXXVogue

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27:21 63%

TS in Training

8 months ago

$$ FapHouse

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49:26 64%

Petra,s 9th training

1 year ago

xHamster

train, dildo, crossdresser, dutch, sissy, hardcore, femboy
15:21 83%

Hattabi4ik sissy femboy trap splatter ejaculation self shag warm humungous bootie compilation

2 years ago

TrannyGem

pissing, train, squirt, orgasm, compilation, cumshot compilation, orgasm compilation
23:09 75%

Mistress training sissies to play together

6 years ago

ShemaleZ

femdom, train, sissy
30:19

Submissive Asian Ladyboy Slave Training & Anal Casting

5 days ago

$$ FapHouse

ladyboy, amateur, casting, anal
15:28

Rides, sissy doll, hd videos

3 weeks ago

XXXVogue

doll, train, bondage, maid, BDSM, riding, sissy
22:26 60%

Risky bang-out with splendid shemale in the train and in the car / Compilation

1 year ago

ShemaleMovie

beauty, public, shemale, train, outdoor, car, tattoo
15:46 72%

Turning My husband Into Tranny tart, lady first time with Tranny

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
27:01 22%

HUMUNGOUS GAPES, Rosebutt, tummy swelling, AMPLE sugary-sweet gape farts, Twunk Jules Verne Assfuck FUCK HOLE DESTRUCTION

4 years ago

TrannyGem

farting, train, huge dildo, fetish, gape, chastity
17:33 46%

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

7 months ago

AShemaleTube

creampie, train, interracial, crossdresser, creampie compilation, compilation, cumshot compilation
23:19 87%

Sissy Trained And Owned By Big Black Penis Bull With Sasha Desade

2 years ago

ShemaleZ

black, POV, train, interracial, gangbang, penis, BBC
19:37 63%

Sissy Whore Training 3 - The Best

2 months ago

HClips

amateur, stockings, train, whore, sissy, toys
21:04 82%

Webcam session of trans femboy bondage & discipline Sissy fuckslut Alina old stuff

6 months ago

ShemaleMovie

train, bondage, dildo, BDSM, crossdresser, deepthroat, webcam
20:35 74%

White Sissy Chastity Training (fuck Machine)

3 years ago

ShemaleZ

train, BDSM, machine, sissy, chastity, solo
20:14 89%

Sasha Desade In Sissy Fuck Training

4 years ago

ShemaleZ

train, threesome, lingerie, sissy, chastity, brunette
29:51 40%

30 mins no break fellate spitroast contest!

7 months ago

TrannyGem

double anal, contest, gangbang, deepthroat, heels, secretary, slut
26:11 86%

Hattabi4ik super-steamy massive booty phat gold rain and cum-shot steaming ginormous compilation

1 year ago

TrannyGem

compilation, cumshot compilation, sissy, femboy, pissing, cumshot
19:58 71%

Uber-cute tiny trap anal teaching

2 years ago

ShemaleMovie

cute, blowjob, train, dildo, crossdresser, riding, toys
22:31 94%

Ryu Woman Takes Glowing Sinnovator 20in Deep

4 years ago

TrannyGem

train, dildo, machine, sissy, gape, shemale
32:02 67%

Hot sluts sucks gigantic dicks

5 years ago

XoZilla

femdom, train, fetish, tease, slut, JOI
23:03

Sissy Training I Transform My Husband Into A Real Sissy. I Fuck Him And Make Him Suck Like A Slut!

2 years ago

Upornia

husband, BDSM, amateur, sissy
19:45 85%

High Class Sissy Training

4 years ago

ShemaleZ

latex, train, BDSM, domination, sissy, brunette
26:50 81%

Jeni Justice Trained And Turned Into A Sexy Sissy

2 years ago

ShemaleZ

stockings, big ass, sissy, train
48:42

C4 Film (april 20, 2025) the boss Is a slut on a flick Conference with Her Banker.

1 year ago

ShemaleMovie

handjob, french, train, lingerie, BDSM, crossdresser, prostitute
16:33 60%

Turning my boyfriend into my girlfriend with female domination and sissy transformation

7 months ago

XXXVogue

strapon, train, crossdresser, girlfriend, sissy, boyfriend
37:42 60%

Sissy Slave And Sissy Slut In 7th Training

11 months ago

HClips

stockings, shemale, POV, blonde, slut, sissy
21:33 60%

Sissy Poppers Hypnose Training III

5 years ago

BeMyHole

train, sissy
18:41

Fake Penis Hero - Dudes take turns to bang you at Costume soiree in the nightclub

6 months ago

TrannyGem

party, sissy, 3D, fetish, JOI
25:34 83%

Assfucking Pummeling Machine - Compil 15

2 years ago

TrannyGem

french, swinger, train, fetish, BDSM, creampie compilation, compilation
18:51 63%

Sissy fuckslut Pegging Compilation Vol.1

7 months ago

ShemaleTaxi

train, orgasm, crossdresser, compilation, orgasm compilation, pegging, sissy
33:06 86%

SISSY Mindcontrol instructing - Sasha de Sade & domina whisper

11 months ago

ShemaleMovie

femdom, teen (18+), train, instruction, maid, BDSM, babe
17:26 69%

Salimur BJ training for big cocks

1 year ago

AShemaleTube

train, interracial, big tits, masturbation, toys, small tits, sissy
18:49 47%

Sissy breezy Jenni needs bbc mega-slut Training

3 years ago

ShemaleTaxi

train, slut, taxi, BBC, sissy, black
20:00 67%

Sissy Poppers Hypnose Training IV

5 years ago

BeMyHole

train
15:36 67%

Purity fox ninja cosplay with intense anal dildo play and destruction

4 months ago

XXXVogue

train, huge dildo, outdoor, dildo, blonde, toys, sissy
15:12 29%

She is worth anal invasion

8 months ago

ShemaleMovie

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16:02 57%

SHE-CREATURE JIZZ COMPILATION STAMINA COMPETE - Can you make it to the end ?

1 year ago

TrannyGem

train, orgasm, compilation, cumshot, ass, cumshot compilation, orgasm compilation
25:45 73%

Belt Cock and handballing-four jizzing in 1 orgy UTTER movie

3 years ago

TrannyGem

femdom, strapon, train, fisting, ass licking, shemale and girl, orgy
18:14 11%

Sissified Masturbation Mindfuck [extreme Poppers]

7 years ago

TrannyGem

train, nipples, masturbation, dildo
28:54 83%

Sissy trains asshole for REAL COCKS (DAP)

3 years ago

IcePorn

stockings, train, solo, toys, asshole, sissy
16:06

Sissy in pinkish sundress and innocence Plays with Her Butt Plug and Gets Fucked Hard by Machine

2 months ago

ShemaleMovie

solo, crossdresser, sissy, machine, shemale, maid
16:52

Super Extended Cut: Feminized Big Ass Sissy Huge Anal Creampie Farts and Ass Stretching Training

2 months ago

$$ FapHouse

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30:41 67%

Submissive Ladyboy Anal Casting & Slave Training

1 year ago

$$ FapHouse

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25:34

Lil knob sissy femboy have fun with protection pee on it guzzle it then jack and jism utter movie

2 years ago

TrannyGem

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20:38

Sissy teaching: how to jizz in purity? Rail ever larger fuck sticks to sissygasm

4 years ago

TrannyGem

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19:27 82%

Sissy Silly Step-Sister Raunchy Drill and Gargle

5 years ago

TrannyGem

train, slut, sissy
32:24 70%

Sissy whore pic Bombardment Conversion Therapy

5 years ago

ShemaleTaxi

train, crossdresser, whore, taxi, sissy
30:58 79%

Scotlands femdom-goddess Inka And Miss Maryln train Sissy hooker To suck penis

6 years ago

TXXX

femdom, train, hooker, BDSM, domination, penis, sissy
34:35 50%

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

8 years ago

ShemaleZ

train, sissy
19:20

Backing that rump Up into a 10 inch Monster penis fucktoy

1 month ago

ShemaleMovie

train, pissing, monster, shemale, sissy, anal
16:47 33%

Inhale My Femboys Dick (with Lina Lux)

6 months ago

TrannyGem

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