SHEMALE • SISSY TRAINING 4,073 videos

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08:37 83%

Dizzy Miss Sizzy Dizzyplined!

5 years ago

VideoSection

train, gagging, bondage, crossdresser
05:30

Sissy whore training hypno

1 month ago

AShemaleTube

shemale, sissy
11:12 81%

Platinum-Blonde TRANSSEXUAL Barbie likes to satisfy BIG BLACK COCK *MUST SEE*

1 year ago

TrannyGem

amateur, homemade, black, teen (18+), teen anal (18+), reality, tight
19:45 80%

Sissy Hypno Training

2 years ago

AShemaleTube

anal, lingerie, crossdresser, sissy
04:36 82%

Iskra Sissy Crossdresser

2 years ago

TrannyGem

feet, femboy, sissy, nylon, heels, crossdresser
12:06 67%

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

5 years ago

TrannyGem

femdom, train, teen anal (18+), 18, slut, sissy
06:27 76%

AmberSis - from Boy to Sissy Doll

7 years ago

TrannyGem

doll, train, bondage, sissy, compilation
08:00

Deep-anal, bbc-dildo, giant-dildo

1 week ago

XXXVogue

black, huge dildo, sissy, orgasm, dildo, BBC
10:10 60%

Punk girl Evolutionlfn lets a dildo machine work her tight ass

10 months ago

XXXVogue

train, prostate, orgasm, dildo, anime, goth, toys
06:02 83%

Korean sissyfemboy g/g have fun (full video at fansly)

10 months ago

ShemaleMovie

creampie, train, korean, crossdresser, gangbang, full movie, femboy
05:15 77%

He pokes me a ultra-cute dude who is very hot

1 year ago

ShemaleTaxi

cute, beauty, stockings, strapon, train, couple, teen anal (18+)
02:24 83%

Femboy locked in purity belt nailed by big black cock fake penis

1 year ago

TrannyGem

fetish, BBC, dildo, sissy, chastity, penis
05:08 71%

伪娘的仙女棒被紧身牛仔裤紧勒到喷射

2 years ago

TrannyGem

teen (18+), thai, train, chinese, sissy, femboy
18:36 80%

GRINDR FATHER POUNDS CD RIGID & FEEDS her a XXL MAMMARY FOUNTAIN of STEAMING JISM

4 years ago

TrannyGem

train, dogging, sissy, crossdresser
06:21

Sissy training with hands-free CUM compilation of explosive shots

4 months ago

AShemaleTube

sissy, compilation, hands free, shemale, train
07:35 60%

Sissy Elf ladyboy In A bondage & discipline Feminization teaching

10 months ago

HDSex

beauty, train, bondage, BDSM, ladyboy, crossdresser, babe
02:16 45%

Ass Fucking Instructing My Sissy Hubby

1 year ago

TrannyGem

shemale, BBW, femdom, wife, pegging, BDSM
12:56 74%

Huge DEEP rope-on pulverize of moaning sissy bitch! PEGGING FemDom Sex, Mistress Arya Grander

1 year ago

ShemaleMovie

femdom, latex, train, chubby, gloves, BBW, lingerie
06:38 88%

Glazing Her Lil Inverted Pearl In Sissy Juices

2 years ago

TrannyGem

train, squirt, orgasm, dildo, penis, anal orgasm, hands free
03:34 70%

Trans Eva Jerk Off Instructions Gets Predominated by TRANSSEXUAL Ria Bentley With Dual Rectal Plaything

2 years ago

TrannyGem

instruction, dirty talk, old and young (18+), slut, JOI, sissy
04:43 56%

PMV Tart Pop - Sissy Peach plow along

3 years ago

TrannyGem

kissing, lesbian, train, gangbang, orgy, machine, sissy
07:04 78%

Sissy Trainer; Feminization; Sissy Instructing; Sissifcation; BIG BLACK COCK

4 years ago

TrannyGem

femdom, strapon, train, instruction, compilation, whore, domination
05:45 82%

Dancing ladyboy with lil bud

4 years ago

TrannyGem

feet, train, dance, slut, sissy, cosplay, femboy
06:16

Hot trans girl anal invasion

1 month ago

ShemaleMovie

german, crossdresser, russian, sissy, shemale fucks guy, indian
09:11 53%

Strawberry assfuck

11 months ago

TrannyGem

amateur, shemale, train, fetish, crossdresser, 18, BBC
19:58 73%

Uber-cute tiny trap anal teaching

2 years ago

ShemaleMovie

cute, blowjob, train, dildo, crossdresser, riding, toys
06:24 88%

Danielle Dicksinme Experiences Arse To Jaws on Her Playthings

4 years ago

TrannyGem

mature, mature anal, train, dildo, crossdresser, ass to mouth, sissy
20:51 56%

Turning the staright boys faggot

4 years ago

TrannyGem

femdom, train, mature, sissy
1:07:40 78%

Tempting t-girls hardcore anal sex collection

4 years ago

Analdin

train, anal, interracial, dildo, compilation, handjob compilation, cumshot compilation
05:24 57%

BBC Bimbo Bimbogiga Sloppy Gagging Extreme Nails

7 years ago

TrannyGem

train, gagging
05:05 81%

Mommy sissy training

1 year ago

AShemaleTube

sissy, mom, train
15:24 79%

Sissy trainning

9 years ago

TXXX

train, sissy
09:34

Sissy Anal Pleasure: Hands-Free Training for Mind-Blowing Orgasms

3 weeks ago

AShemaleTube

amateur, sissy, hands free, shemale
24:46 67%

Chastity Sissy Gets tights Torn and Pegged by Bad Dragon Strapon by mistress Mercer

8 months ago

ShemaleMovie

femdom, strapon, train, BDSM, spanking, toys, tight
03:14 86%

Ultra-Cute sissy I wank ♡ chinese crossdresser getting off

10 months ago

TrannyGem

ladyboy, asian, sissy, cumshot, chinese, japanese
20:59 53%

White Sissy Virginity Instructing (Smash Machine)

10 months ago

TrannyGem

femdom, teen (18+), instruction, fetish, teen anal (18+), bondage, BDSM
16:33 67%

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

10 months ago

XXXVogue

strapon, train, crossdresser, girlfriend, sissy, boyfriend
10:44 77%

Tgirl takes two dildos in anal instructing flick

1 year ago

ShemaleMovie

shemale, sissy, ass, dildo, instruction
08:16 82%

Sissy in Pink Dress and Chastity Plays with Her Butt speculum and Gets porked firm by Machine

1 year ago

ShemaleMovie

train, maid, crossdresser, masturbation, heels, dress, machine
10:13 65%

Dominatrix screws Sissy Cockslut buttfuck doggie-style

1 year ago

TrannyGem

homemade, femdom, strapon, dogging, pegging, sissy, femboy
02:31 81%

Sissy College Girl Gets Demolished and Creampied by BIG BLACK COCK

2 years ago

TrannyGem

interracial, crossdresser, BBC, sissy, chastity, femboy
02:06 38%

Femboy Babecock type sissy teaser

3 years ago

TrannyGem

toys, BBC, sissy, femboy
11:32

Sissy beotches always guzzle jism - BOF CEI

3 years ago

ShemaleTaxi

train, swallow, taxi
03:30 76%

Sissy Whore Hypnosis

6 years ago

xHamster

train, whore, sissy, latex
06:28

Bitch Trixyit Comes Home and Gets Fucked rock hard by Her beau

3 weeks ago

ShemaleMovie

babe, sissy, crossdresser, anal
08:14 93%

Brie Meets Thad (feat. Thad Maxxx)

7 months ago

ShemaleTaxi

black, train, anal, couple, british, jerking, bareback
12:34 57%

Submissive teaching with nipple play and pain tolerance featuring Allywhorefrost

10 months ago

XXXVogue

BDSM, compilation, nipples
08:57 60%

Punk gal instructs her femboy brother to become a superb mega-bitch (Female Domination 3 DIMENSIONAL cartoon)

10 months ago

TrannyGem

femdom, strapon, train, instruction, bondage, crossdresser, shemale and girl
11:40 57%

Wringing a meatpipe into a micro cell

12 months ago

TrannyGem

sissy, chastity, penis, insertion
02:28 80%

Mind-Blowing nymph in office sight and high high-heeled shoes demonstrating her pansy figure

1 year ago

TrannyGem

feet, stockings, public, train, bondage, office, heels
02:41 53%

AB112 Maid human toy instructing - splooging,jizz flow (Asian and English subtitles)

1 year ago

TrannyGem

pantyhose, femdom, strapon, train, squirt, instruction, bondage
05:30 72%

Domme Eudoras ass-fuck bitch

1 year ago

ShemaleMovie

french, strapon, train, fisting, BDSM, domination, asshole
10:07

Trans Lubricated And Plumbed Condom-Free

1 year ago

TrannyGem

train, sissy, crossdresser, big ass, turkish, amateur
09:42 89%

巨大ディルドで尻の穴ヒクヒク

1 year ago

TrannyGem

amateur, indian, french, train, asian, japanese, korean
10:16 81%

Blessed Japanese Fresh Yr-Crimson food contest and super-cute deep-throat job

4 years ago

TrannyGem

feet, cute, pantyhose, stockings, femdom, train, asian
09:18

Sissy Training by Queen Daralis Part 3

7 months ago

$$ FapHouse

dildo, sissy, amateur, stockings
06:14 75%

Lola Spais In Hard Sissy Training Compilation!

1 year ago

HClips

outdoor, sissy, crossdresser, amateur, POV, public
28:54 83%

Sissy trains asshole for REAL COCKS (DAP)

3 years ago

IcePorn

stockings, train, solo, toys, asshole, sissy
07:58 80%

Popper Sissy Training II by Iggy

10 years ago

TXXX

train, sissy
10:18

Feminization Instructing to Turn You into a Obedient Sissy Foolish #0

1 month ago

TrannyGem

masturbation, sissy, instruction
24:54 50%

Sissy super-bitch plumbing her butt hole with phat fake penis

1 year ago

TrannyGem

cute, femdom, strapon, german, train, teen anal (18+), dildo
13:12 83%

Point of view: nubile Horny Femboy Trains His bum in Front of the Camera

1 year ago

ShemaleMovie

teen (18+), train, teen anal (18+), dildo, cumshot, babe, ass
11:26 68%

Sissy instructing - Feminization

2 years ago

ShemaleMovie

femboy, sissy, shemale, instruction, train, maid
19:52 66%

Feminizaton - Sissy Instructing - COSMIC SISSY FATE

2 years ago

TrannyGem

instruction, compilation, dirty talk, cumshot compilation, JOI, BBC
05:17 67%

Episode 1 the Sexy Shemale Gets You off Sucking Cock Its Goddess Lana as a Shemale

2 years ago

xHamster

instruction, dirty talk, dress, JOI, sissy, jerking
18:49 49%

Sissy breezy Jenni needs bbc mega-slut Training

4 years ago

ShemaleTaxi

train, slut, taxi, BBC, sissy, black
04:49

Sissy Kaluna deep-throats BIG BLACK COCK

4 years ago

TrannyGem

train, british, BBC, chastity, crossdresser
10:11 75%

Sissy Mara Jades UTTER Sissygasm Innocence Compilation!

4 years ago

TrannyGem

train, teen anal (18+), bondage, 18, compilation, cumshot compilation, chastity
12:29 66%

Adorable Sissy Virginity Gimp Let Out to be Taunted Denied Abased and Locked up by Domme Mercer

4 years ago

TrannyGem

femdom, train, tease, bondage, reality, sissy, chastity
21:01 60%

TRANSSEXUAL Silly Female Dom Honeypot Whips Blond Cable Kitten

4 years ago

TrannyGem

train, bondage, BDSM, 18, sissy, shemale and girl
19:27 85%

Sissy Silly Step-Sister Raunchy Drill and Gargle

5 years ago

TrannyGem

train, slut, sissy
32:24 69%

Sissy whore pic Bombardment Conversion Therapy

6 years ago

ShemaleTaxi

train, crossdresser, whore, taxi, sissy
06:12 54%

Sissy BBC training compilation

6 years ago

xHamster

train, creampie compilation, compilation, sissy
07:18 60%

Trans corporal Therapist Ria Bentley Works Wonders On big black cock Patient

1 month ago

ShemaleMovie

beauty, shemale, train, massage, bareback, skinny, BBC
54:11 33%

Hd videos, her bitch, french trans

3 months ago

XXXVogue

amateur, french, train, ladyboy, crossdresser, facial, prostitute
17:18 63%

Natacha slut from Lyon romped like a breezy

4 months ago

ShemaleMovie

french, shemale, crossdresser, sissy, BDSM, prostitute
03:48 80%

Made to Spunk On Her Back From Dual Intrusion

7 months ago

TrannyGem

amateur, sissy, prostate, hands free, anal orgasm, massage
05:47 60%

Amy Jizzes Firm for (D)addy

1 year ago

TrannyGem

big tits, dirty talk, riding, surprise, sissy, femboy
08:59 81%

Bdsm clothed transgender princess in zentai full bodysuit nylon

1 year ago

ShemaleMovie

pantyhose, train, boots, lingerie, BDSM, heels, full movie
11:14 60%

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

1 year ago

ShemaleMovie

handjob, beauty, french, train, lingerie, BDSM, prostitute
02:34 73%

Ria Bentley Gives Public Camper SUCK OFF Thick Facial Cumshot

1 year ago

TrannyGem

public, teen (18+), MILF, car, facial, babe, cum in mouth
07:17 86%

Cutlerx, bbc and Jackpot Hankeys playthings porking Chantals Tiny Hole

1 year ago

HDSex

german, train, huge dildo, dildo, toys, slut, BBC
08:12 50%

Lady Alice Compilation 07 - Mesmerizing Beautiful

2 years ago

xHamster

mature anal, outdoor, sissy, strip
06:26 72%

Fuck machine bdsm latex

4 years ago

xHamster

latex, teen (18+), bondage, danish, machine
10:22 79%

Super-fucking-hot pop-shot compilation of humid ejaculations slut femboy sissygasm mega-slut bum

4 years ago

TrannyGem

train, orgasm, creampie compilation, orgasm compilation, slut, JOI, anal orgasm
12:13

Ass Fucking vegetables injection

4 years ago

TrannyGem

train, insertion, anal orgasm
21:05 73%

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

5 years ago

TrannyGem

femdom, strapon, train, dress, slut, sissy, femboy
03:40 60%

Sissy training

2 years ago

XXXDan

beauty, black, train, BDSM, cuckold, 3D, gangbang
02:46 58%

Tied Up Bondage Asian Sissy Training 2

3 years ago

xHamster

bondage, maid, tied, sissy
05:44

Ash-blonde Futa Shemale Sucks Cock Before assfuck boinking

3 weeks ago

ShemaleMovie

sissy, shemale fucks guy, big cock, prostitute, futanari, train
07:59 74%

Trans Sissy Slut French Maid Service Training

3 months ago

GetTranny

femdom, shemale, french, train, anal, maid, lingerie
07:01

Sissy dame plowing in a Pegging date

4 months ago

HDSex

latex, strapon, train, lingerie, BDSM, british, mask
21:18 88%

Fresh fucktoy training For A Shackled Sissy by Mistress Mercer

7 months ago

VideoSection

femdom, train, bondage, dildo, BDSM, sissy, gape
10:14 60%

Trans Sissy tramp French Maid Service teaching

8 months ago

ShemaleMovie

shemale, french, sissy, cumshot, facial, train
23:35 29%

Satin-clad sissy maid Sissy Candy Sparkle gets dominated by her nymph in bondage and loses her virginity

9 months ago

XXXVogue

train, satin, bondage, maid, dildo, crossdresser, toys
03:30

Sissy Tramp snowbunny taking a monstrous black hard-on

9 months ago

TrannyGem

creampie, train, latina, crossdresser, shemale and girl, babe, slut
10:51 60%

Sissy In diaper penalized With stringent Pegging

10 months ago

ShemaleTaxi

crossdresser, sissy, diaper, pegging, strapon
12:16 17%

Sissification feminization sissy instructing - Sissy spouse story part two (english voice)

10 months ago

TrannyGem

femdom, bisexual, train, instruction, cuckold, big cock, JOI
22:26 60%

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

1 year ago

ShemaleMovie

public, shemale, train, outdoor, car, tattoo, crossdresser
56:10 50%

Sissy bi-atch Late Evening Supper

2 years ago

ShemaleTaxi

POV, train, orgasm, crossdresser, close up, kitchen, nylon
05:13 58%

Autofellatio Sissy Slut Part two

2 years ago

ShemaleTaxi

german, train, huge dildo, selfsuck, sissy, skirt, femboy
26:50 82%

Jeni Justice Trained And Turned Into A Sexy Sissy

2 years ago

ShemaleZ

stockings, big ass, sissy, train
21:05 60%

Training my anal pussy

2 years ago

xHamster

fisting, dildo, escort, sissy
04:03 77%

Train my sissy ass with my new big dildo

3 years ago

xHamster

public, huge dildo, anal, dildo, solo, masturbation, sissy
02:03 64%

Inhale discipline for Thick Sissy Victim.

4 years ago

TrannyGem

fat, train, bondage, piercing, nipples, tied, mask
11:15 79%

*Trailer* Sissy Instructing Basics With Kelli Frost

4 years ago

TrannyGem

train, instruction, chastity
16:48 67%

Sissification Lecture encaged Sissy Innocence Belts, Fap, Sissygasm by Dominatrix Veronica Taboo

4 years ago

TrannyGem

train, instruction, tease, JOI, chastity
16:48 38%

Sissification lecture Encaged Sissy V-Card Belts, Masturbate, Sissygasm by Domina Veronica Taboo

4 years ago

TrannyGem

femdom, train, instruction, tease, JOI, sissy, chastity
15:12

TRANSSEXUAL Silly Tabletop Gamer Inhales and Boinks Dungeon Space Sir

5 years ago

TrannyGem

train, bondage, BDSM, game, sissy
07:25 60%

Sissy Instructing Part two

5 years ago

TrannyGem

train, instruction, BDSM, cuckold
22:39 71%

Trained To masturbate off By cold-blooded Natalia Forrest: Abjecting Her latest Averse Spandex Sissy Maid

6 years ago

TrannyGem

latex, train, maid, uniform, spandex, masturbation
13:39 89%

Connie Cage Trains and Leaks for her Owners

6 years ago

TrannyGem

train, old and young (18+), chastity
23:32

A guide to sissication: Beginner - Am I a sissy?

6 years ago

xHamster

train, sissy
53:13 67%

Petra,s 10th teaching

3 months ago

ShemaleTaxi

amateur, stockings, train, huge dildo, anal, ass to mouth, ass
06:52 59%

Ryley takes charge and rides you hard

7 months ago

XXXVogue

train, BDSM, solo, british, cumshot, riding, blonde
04:36

She Dreams So Much It Was Hers That She Ejaculates

7 months ago

TrannyGem

shemale, hands free, chastity, train
05:59 80%

Mature domina adore JOI

11 months ago

ShemaleTaxi

mature, shemale, femdom, JOI, taxi
1:09:32

Petras pornography marathon part 1-three

1 year ago

ShemaleMovie

train, fisting, dildo, crossdresser, heels, toys, BBC
05:30 81%

Feminized she-male gets cooter penetrated

1 year ago

TrannyGem

train, fetish, orgasm, fisting, bondage, BDSM, sperm
04:24 81%

I jizm from snatch porking

1 year ago

TrannyGem

cute, teen (18+), train, fetish, fisting, bondage, japanese

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