SHEMALE • SISSY TRAINING 3,828 videos

Popular Latest Top rated

05:27 38%

Petite 19 Years old Sissy Chris Did His first-ever Glory slot Handjob & Getting Cum Facial

1 week ago

ShemaleMovie

cumshot, compilation, amateur, sissy, cumshot compilation, swallow, gloryhole
13:44 77%

Wonderful femboy in crotchrope takes gigantic cock in tight ass until cum

1 month ago

ShemaleTaxi

beauty, shemale, train, anal, big ass, orgasm, dildo
18:46 60%

Destroyed Climax For Circumcised DORKS (with Lina Lux)

6 days ago

TrannyGem

femdom, shemale, amateur, sissy, POV, german, asian
07:35 56%

Sissy Elf ladyboy In A bondage & discipline Feminization teaching

1 month ago

HDSex

beauty, train, bondage, BDSM, ladyboy, crossdresser, babe
05:15 75%

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

3 months ago

ShemaleTaxi

cute, beauty, stockings, teen (18+), strapon, train, couple
04:59 73%

Chained Innocence Sissy Marionette takes Supah-Sized Faux-Cock and female dominance Spandex Going Knuckle Deep by Domina Mercer

1 month ago

TrannyGem

femdom, latex, huge dildo, fetish, fisting, bondage, gloves
07:39 61%

Pump 2 Me - Sissy GOON Trainer

5 years ago

xHamster

handjob, compilation, swallow, handjob compilation, deepthroat, cum in mouth, cumshot compilation
17:44 86%

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

3 days ago

ShemaleMovie

femdom, sissy, BDSM, shemale, anal
17:35 33%

Adore Her Femboy Marionette (with Lina Lux)

6 days ago

TrannyGem

shemale, asian, amateur, femboy, sissy, femdom
12:38 71%

Sissy Training

11 years ago

xHamster

train, sissy
16:47

Inhale My Femboys Dick (with Lina Lux)

6 days ago

TrannyGem

femdom, shemale, amateur, femboy, POV, blowjob, asian
02:15 70%

Tied to the BIG BLACK COCK breeding simulator [recommended training]

4 months ago

TrannyGem

train, prostate, teen anal (18+), orgasm, bondage, 18, tied
10:39

Tough Morning Ass Fucking Boink Makes Transgender Lady Bellow and Squeal Noisily

1 week ago

TrannyGem

sissy, femboy, amateur, homemade, shemale and girl, creampie, couple
10:04 75%

Trans Sissy Slut French Maid Service Training

4 weeks ago

AShemaleTube

shemale, french, train, fetish, maid, ass to mouth, slut
28:06 61%

SADISM & MASOCHISM Sissy fellate instructing with clyster!

3 months ago

TrannyGem

amateur, stockings, shemale, blowjob, train, instruction, fetish
05:53 60%

Foolish sissy tramp take the dick inside mouth and suffers humiliated like a good girl

1 year ago

ShemaleMovie

blowjob, creampie, train, BDSM, crossdresser, facial, cum in mouth
04:22

Balaclava BIG BLACK COCK trains sissy femboy how to be a superb bottom

1 week ago

TrannyGem

small tits, amateur, crossdresser, BBC, sissy, femboy, big cock
03:21 52%

Trans BIG BLACK COCK 11-inch Dominance Xxx Wrecking This Skimpy Men Gullet In Leather Footwear!!! Jism Fountain

3 months ago

TrannyGem

black, femdom, lesbian, train, cuckold, leather, cum in mouth
04:34 79%

Sissy blows a load inwards undies

1 month ago

TrannyGem

amateur, femdom, teen (18+), shemale, creampie, train, big ass
08:04 77%

Trained to Be a Submissive Slut

5 months ago

AShemaleTube

stockings, shemale, blowjob, train, anal, cum in mouth, bareback
07:29 45%

Sissy Jessica Bloom teaches you how to suck dick and swallow cum

3 months ago

XXXVogue

amateur, beauty, public, train, dildo, crossdresser, swallow
02:52 49%

【Hands Free-For-All Orgasm】Japanese sissy 『Nipple Masturbation』Hands Free♡【ladyboy 女装偽娘 crossdresser】

2 years ago

TrannyGem

orgasm, japanese, nipples, sissy, hands free, shemale
17:13 50%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

3 months ago

TrannyGem

teen (18+), crossdresser, british, 18, whore, slut, sissy
14:00 79%

Tgirl nutting and degustating her own jizz for the first-ever time

7 months ago

TrannyGem

cute, teen (18+), train, crossdresser, 18, masturbation, blonde
07:48 56%

Sissification Feminization Reprogramming Female Domination POINT OF VIEW Brainwashed Sissy Mindfuck

2 years ago

TrannyGem

femdom, fetish, JOI, sissy, femboy, crossdresser
10:55 83%

Folks Gobbling She-Creature Jizz Compilation

6 years ago

TrannyGem

train, compilation, swallow, cum in mouth, cumshot compilation, sissy, brunette
10:11 67%

I cant stop spunking! T-woman no-arms utter assets climaxes with hitachi

3 years ago

TrannyGem

pissing, train, prostate, hands free, femboy, orgasm
05:06 20%

Handsome eighteen yr elderly ts female takes off in the countryside

2 weeks ago

TrannyGem

cute, small cock, creampie, dogging, crossdresser, ass licking, babe
06:50 86%

TRANSSEXUAL bitch has joy with two stiffys

1 week ago

TrannyGem

BBC, femboy, sissy, amateur, chastity, gangbang
10:53 79%

The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded

1 year ago

xHamster

toilet, pissing, creampie, whore, sissy, femboy
21:13 81%

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

1 month ago

ShemaleTaxi

beauty, small cock, shemale, train, orgasm, ladyboy, babe
22:45 81%

Amateur Couple and Trans - Train

1 year ago

xHamster

amateur, teen (18+), train, threesome, couple, teen anal (18+), sissy
18:28 80%

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
05:30 80%

Feminized she-male gets cooter penetrated

7 months ago

TrannyGem

train, fetish, orgasm, fisting, bondage, BDSM, sperm
07:35 88%

Bound Sissy Gets trunk jerked Then Fed Her Own Load of Cum - Jessica Bloom and Polieana

1 month ago

ShemaleTaxi

latex, train, orgasm, bondage, crossdresser, cumshot, jerking
18:28 80%

GIGANTIC Strapon Pegging with Bad Dragon and Hankey for whorish Sissy bi-atch by domme Mercer

1 week ago

VideoSection

sissy, shemale, BDSM, anal, pegging, strapon
10:48 47%

Sissy Teaching - Feminization - Sissy TASK - when you observe a chick

1 year ago

TrannyGem

train, compilation, dirty talk, cumshot compilation, JOI, BBC, sissy
08:12 80%

When your sissy is missing parents rod

1 year ago

TrannyGem

dildo, crossdresser, riding, masturbation, slut, JOI, sissy
07:05 83%

Top Trans Emo Damsel Bangs Masculine Masturbator Fuck-A-Thon Plaything Till Massive Jizz Flow and Ahegao Eye Spin

4 months ago

TrannyGem

femdom, teen (18+), emo, 18, dirty talk, cumshot, babe
10:16 60%

Femboy forces an whole fake penis up his booty and pushes it out until he cums

2 months ago

ShemaleMovie

amateur, train, huge dildo, anal, monster, riding, penis
07:22 81%

Sissy Popper Training 1

5 years ago

BeMyHole

train, sissy, shemale
02:19 55%

Chinese sissy Femboy GOKKUN messy milk Mushy core swim suits

3 weeks ago

TrannyGem

train, asian, japanese, milk, crossdresser, swallow, swimsuit
07:47 72%

Sissyfication Vol.4 by Sonechka25 (instructions on How to Achieve a gal dump for a gal with a Penis).mp4

3 months ago

ShemaleTaxi

amateur, stockings, prostate, instruction, orgasm, dildo, cuckold
04:07 88%

Killer trans girly bone spunk rigid

8 months ago

TrannyGem

handjob, hairy, 18, cumshot, college, sissy, femboy
15:04 68%

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

4 years ago

TrannyGem

mature, femdom, mature anal, train, granny, british, dirty talk
03:04 58%

CHINESE TRANSGIRL LEITAOXIV DANCING UNTIL SHE SPUNK

1 year ago

TrannyGem

cute, thai, asian, japanese, ladyboy, crossdresser, shemale and girl
03:19 75%

Ta nouvelle sexualité comme Sissy : EP5 Transformer un Branleur en Esclave - Maitresse Julia Female Dominance

10 months ago

TrannyGem

femdom, shemale, french, strapon, train, fetish, crossdresser
34:54 85%

Gorgeous tgirl Angel dildo training

1 year ago

AShemaleTube

train, anal, big tits, dildo, masturbation, ass, toys
02:36 74%

Monster 12 BIG BLACK COCK Ravages Skinny Femboy Sissy Fuckslut

9 months ago

TrannyGem

ebony, black, train, anal, interracial, monster, big cock
05:44 89%

2 BIG BLACK COCK Find out the Sissy Stud is a She, Youthful TRANSSEXUAL Sissy Trans Tranny Transgirl

5 years ago

TrannyGem

teen (18+), POV, train, teen anal (18+), crossdresser, gangbang, college
03:52 82%

Sissy Cum Swallow Training 2

7 years ago

xHamster

train, swallow, sissy, shemale fucks guy
15:35 61%

Sissy Hypno #2: Becoming A Cock Slut

4 years ago

xHamster

train, sissy, creampie
11:24 57%

The rosy Maid Used as a cock cockblower. Caught Playing the Whore. Vanessabitchx

2 months ago

ShemaleTaxi

french, blowjob, train, doctor, nurse, couple, bondage
08:14 64%

We Worship your Cock! (cocksucking and Sissy PMV)

6 years ago

TrannyGem

train, short hair
05:20 69%

HOTTEST Femboy Sissygasm Compilation #1

5 months ago

TrannyGem

feet, teen (18+), teen anal (18+), orgasm, milk, crossdresser, 18
07:33

Thick stream popshot on my hooters after the bathroom

2 weeks ago

TrannyGem

shemale, crossdresser, teen (18+), solo, shemale and girl, masturbation, nipples
17:07 66%

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

1 year ago

TrannyGem

mom, fat, instruction, facesitting, shemale and girl, stepmom, domination
03:20 81%

Having a fantastic sissy time

9 months ago

TrannyGem

BBC, sissy, amateur, chastity, shemale, bondage
23:35

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

3 days ago

XXXVogue

bondage, crossdresser, shemale, maid, domination, sissy
17:32 57%

Sissy bbc training Encouragement Crossdresser bi-racial Fiona Fortune

3 weeks ago

HDSex

amateur, black, shemale, creampie, train, anal, crossdresser
05:20

Foolish Sissy Feminization Captions

1 month ago

TrannyGem

amateur, sissy, slut
12:37 47%

Parent gets super-naughty while sissy does cowers

4 years ago

TrannyGem

train, chubby
17:29 94%

TS Schoolgirl Sasha Helps you Learn about Shemale Anatomy

6 years ago

TrannyGem

train, instruction, british, dirty talk, small tits, JOI, sissy
21:04

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

3 weeks ago

ShemaleMovie

train, bondage, dildo, BDSM, crossdresser, deepthroat, webcam
06:08 86%

Rigid Ass-Fuck Penetrate; Sissy; Female Dominance

3 years ago

TrannyGem

femdom, strapon, train, milk, crossdresser, whore, pegging
03:39

Trans Goddess Pummeling Machine

1 week ago

TrannyGem

fetish, dildo, sissy, cosplay, chastity
26:38 77%

Trained to Be Completely Subservient to Him

5 months ago

$$ FapHouse

amateur, black, train, interracial, bareback, sissy, hardcore
22:39 80%

Sissy Crossdresser - Amateur Couple And Trans - Train

11 months ago

ShemaleZ

amateur, stockings, teen (18+), shemale, POV, train, threesome
11:18

Kinky sissy brat gets punished with a paddling by Mistress Mercer

2 weeks ago

XXXVogue

domination, bondage, sissy, BDSM
10:44 76%

Tgirl takes two dildos in anal instructing flick

3 months ago

ShemaleMovie

shemale, sissy, ass, dildo, instruction
1:02:22 71%

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

1 year ago

xHamster

amateur, train, anal, crossdresser, dutch, bareback, skinny
18:22 66%

Sissy breezy Is What u Will Always Be

5 years ago

TrannyGem

cute, train, BDSM, spanking, clit, compilation, prostitute
1:27:33 71%

Sissy in Training

6 years ago

xHamster

train, domination, sissy
05:35 80%

Trans dresses as schoolteacher, costume play, wants to have fun with his college girls

3 years ago

TrannyGem

stockings, train, japanese, crossdresser, 18, teacher, college
10:10

Punk girl Evolutionlfn lets a dildo machine work her tight ass

1 month ago

XXXVogue

prostate, orgasm, dildo, anime, goth, toys, machine
07:31 76%

Phat donk femboy bum fuck stick compilation

1 year ago

TrannyGem

farting, big ass, dildo, compilation, BBC, gape
08:57

Micha Matures T-Model Compilation 1

1 week ago

TrannyGem

big cock, cumshot compilation, sissy, mature, mature anal, crossdresser, amateur
20:59 50%

White Sissy Virginity Instructing (Smash Machine)

1 month ago

TrannyGem

femdom, teen (18+), POV, instruction, fetish, teen anal (18+), bondage
42:54 51%

My Path to Life as A Sissy Hoe

6 years ago

TrannyGem

train, whore, sissy, compilation
05:48 71%

Egyptian cuckold mother caught stepson in underwear

7 months ago

ShemaleMovie

amateur, arab, bisexual, train, cuckold, crossdresser, husband
03:30 71%

Sissy Whore Hypnosis

5 years ago

xHamster

train, whore, sissy
12:10 62%

Bbc Neighbor Back For More messy Head From Pretty Trans lady

3 months ago

ShemaleMovie

black, train, deepthroat, BBC, sissy, femboy
04:24 79%

I jizm from snatch porking

7 months ago

TrannyGem

cute, teen (18+), train, fetish, fisting, bondage, japanese
13:20 94%

Blonde femboy fuck machine sissy training!

1 year ago

xHamster

sissy, femboy, dildo, beauty, machine, cute
10:45

SISSY Buttfuck Instructing by SPANDEX Domme

2 days ago

TrannyGem

crossdresser, femboy, chastity, amateur, femdom, latex, sissy
17:09 59%

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

1 year ago

ShemaleMovie

black, POV, train, anal, instruction, 18, full movie
06:18 79%

Glamgurlxoxo: Sissy CD gives Wet BJ and Swallow Hot Cum Load from Young Guy

5 years ago

TrannyGem

train, swallow, wet, sissy
10:21 73%

Stepsis Providing Me Some Ass-Fuck Instructing So She Can Knuckle Me

1 month ago

TrannyGem

shemale, train, huge dildo, instruction, fetish, fisting, 18
04:42 48%

Enormous, long, beefstick in my appetizing booty

5 months ago

TrannyGem

cute, femdom, strapon, train, fetish, fisting, bondage
07:06

Innocence Sissy Maid Service training With Ria Bentley

2 days ago

ShemaleMovie

ass to mouth, shemale, sissy, cumshot, anal, group
03:35

Open your jaws, I have prepped something mouth-watering for you

2 days ago

TrannyGem

cute, crossdresser, amateur, sissy, femdom, facesitting, handjob
04:59 71%

Fuck-Fest Gimps sixty-nine Dual female domination Pegging and Sissy Jizzing with Face-Sitting on the Fuckmachine

1 month ago

TrannyGem

femdom, strapon, bisexual, fetish, facesitting, reality, machine
02:22 78%

Halloween Killer Angel Sissy Biotch Lola getting jaws penetrated by immense black pipe

3 months ago

TrannyGem

sissy, BBC, crossdresser, femboy, interracial, slut
03:46 66%

Sissy Jizzes with Emasculation Dog Collar on -Elastrator Have Fun

2 years ago

TrannyGem

bondage
11:28 91%

Mistress and bbc train sissy in chastity

6 months ago

AShemaleTube

sissy, BBC, chastity, femdom
08:01 92%

Training Your Sissy

2 years ago

GetTranny

stockings, POV, train, crossdresser, facial, deepthroat, sissy
20:41 71%

Sissy Poppers Hypnose training IV

4 years ago

ShemaleTaxi

train, sissy, shemale
05:12

Stoner Girl

3 weeks ago

TrannyGem

smoking, train, anal, fetish, big tits, blonde, babe
05:33 95%

Getting drilled into obedience

9 months ago

TrannyGem

train, anal, fetish, bondage, ass, reality, BBC
06:13 95%

Femboy dancing and fapping with large penis

3 years ago

TrannyGem

amateur, train, dance, party, fetish, asian, orgasm
20:10 81%

Ass fucking Update two: queen Edition!

6 months ago

ShemaleMovie

beauty, stockings, train, dildo, solo, ass, toys
07:05 60%

Draped Trans domina penalizes Lazy Sissy Maid

1 month ago

ShemaleMovie

maid, sissy, anal, shemale, femdom
08:34 76%

Female dom dominatrix fucks bitch sissy ass, double jizz anal orgasm

4 months ago

ShemaleMovie

shemale, strapon, prostate, orgasm, ladyboy, double anal, crossdresser
05:41 60%

Feminization Sissification - Sissy teaching - FEEBLE SISSY BOY

2 years ago

TrannyGem

femdom, JOI, sissy
41:04 57%

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

1 month ago

XXXVogue

dildo, futanari, sissy, mom, shemale
09:11 54%

Strawberry assfuck

2 months ago

TrannyGem

amateur, shemale, train, fetish, crossdresser, 18, ass
11:52 55%

SISIFICATION, BBC ADDICTED Submissive Training Part 2 (Your ANUS Will Receive A Big, Thick And Very Veiny Cock) Sissy Training

5 months ago

BeMyHole

domination, sissy, BBC, cartoon, big cock, train
23:19 87%

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

2 years ago

ShemaleZ

black, POV, train, interracial, gangbang, BBC, sissy
13:28

SOUNDING WITH ELECTRIC TORMENT & BREATHPLAY FOR SISSY VICTIM

2 months ago

TrannyGem

cumshot, vibrator, bondage
11:04 71%

Sissy Cum Swallow Training

3 years ago

TrannyOne

train, swallow, sissy
05:04 88%

Russian transvestite fucks herself with a dildo (Part 1)

3 years ago

TrannyGem

teen (18+), train, russian, dildo, crossdresser, 18, sissy
08:31 73%

Sissy Training! 9 Min

2 years ago

TXXX

mature, shemale, sissy, domination
08:21

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

2 weeks ago

ShemaleMovie

cumshot, cumshot compilation, compilation, crossdresser, fisting, cum in mouth, sissy
20:21 79%

Forced By Step Mommy Sissy Enema And Anal Training

2 years ago

ShemaleZ

mom, sissy, stockings, train
06:38 61%

He CAUGHT ME Smashing my Sissy Poon Roadside and Sees me JIZM in Public

4 years ago

TrannyGem

public, voyeur, train, flashing, caught, sissy, skirt
09:55 58%

AmberSis - Sissy whore

5 years ago

ShemaleMovie

creampie, train, crossdresser, creampie compilation, compilation, prostitute, whore
02:26 76%

Trans gf Daniela Chanel penetrates my taut crevice with her phat girlcock.

10 months ago

TrannyGem

amateur, femdom, small cock, POV, train, shemale and girl, cumshot
05:14

Sissy Samantha teaches how to give a blow job using a real dick toy

1 month ago

XXXVogue

amateur, sissy, beauty, babe
05:37

Mistress Lord Maria trains her sissy bi-atch to give a blowjob in sexy black lingerie

1 month ago

XXXVogue

stockings, femdom, shemale, bisexual, train, BDSM, cuckold
06:04 69%

The banged of a sexy sissy femboy (full vid at fansly)

1 month ago

ShemaleTaxi

crossdresser, femboy, creampie, sissy, anal

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