SHEMALE • SISSY TRAINING 4,078 videos

Popular Latest Top rated

16:06 86%

OIivia Jade - Sissy Training

1 week ago

AShemaleTube

sissy, shemale fucks guy, shemale, cumshot, stockings
14:59 60%

Lingerie Sissy Candy Is Locked on Her Dildo Stand in restrain bondage and jizzes with electro-hitachi

1 month ago

ShemaleTaxi

stockings, small cock, train, bondage, dildo, BDSM, solo
05:14 79%

4 Inch broad plaything on Machine

5 months ago

HDSex

pantyhose, stockings, train, huge dildo, orgasm, dildo, lingerie
31:01 82%

Dutch, femboy anal, used hard

2 months ago

XXXVogue

amateur, public, blowjob, train, outdoor, dildo, ladyboy
08:51 79%

Brunette shemale Gaellecentre2 shows off her skills in front of her audience

5 months ago

XXXVogue

feet, stockings, shemale, train, couple, lingerie, BDSM
04:59 69%

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

9 months ago

TrannyGem

femdom, latex, train, huge dildo, fisting, bondage, gloves
02:15 71%

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

11 months ago

TrannyGem

train, prostate, teen anal (18+), orgasm, bondage, tied, machine
07:39 60%

Pump 2 Me - Sissy GOON Trainer

5 years ago

xHamster

handjob, train, compilation, swallow, cumshot, big cock, handjob compilation
10:48 50%

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

1 year ago

TrannyGem

train, compilation, dirty talk, cumshot compilation, JOI, BBC, sissy
10:55 82%

Folks Gobbling She-Creature Jizz Compilation

6 years ago

TrannyGem

train, compilation, swallow, cum in mouth, cumshot compilation, sissy, brunette
12:38 72%

Sissy Training

12 years ago

xHamster

train, sissy
39:26 83%

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

5 months ago

ShemaleTaxi

train, huge dildo, fisting, dildo, double anal, crossdresser, taxi
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
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
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, fetish, bondage, dildo
11:47 44%

Jism countdown with TRANSSEXUAL PHAT ASS WHITE GIRL opening up her immense succulent caboose & cock-squeezing rosy crevice

10 months ago

TrannyGem

teen (18+), train, teen anal (18+), 18, college, JOI, sissy
29:44 60%

Mature, crossdressing, amateur

2 months ago

XXXVogue

mature, french, blowjob, train, party, BDSM, crossdresser
10:11 62%

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

4 years ago

TrannyGem

pissing, train, prostate, orgasm, 18, hands free, femboy
06:18 57%

Feminized to Go to the Club

2 weeks ago

ShemaleMovie

strapon, train, couple, BBW, lingerie, crossdresser, british
11:32 25%

Hd videos, beautiful trans, mommy sissy

3 weeks ago

XXXVogue

mom, indian, shemale, strapon, train, fisting, BDSM
02:44 57%

Sensual Sissy Anal Fisting Training with Massive Gape and Prolapse

1 month ago

Sexu

amateur, femdom, train, fisting, dogging, goth, sissy
04:42 65%

Enormous, long, beefstick in my appetizing booty

1 year ago

TrannyGem

cute, femdom, strapon, train, fetish, fisting, bondage
02:52 46%

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

3 years ago

TrannyGem

asian, orgasm, japanese, nipples, hands free, femboy
17:13 51%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

11 months ago

TrannyGem

teen (18+), train, crossdresser, british, 18, whore, slut
03:20 86%

Having a fantastic sissy time

1 year ago

TrannyGem

train, fetish, bondage, BDSM, slut, BBC, sissy
10:53 72%

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
05:05 88%

Trans dame kneads beefstick and shoots a load in undies

2 years ago

TrannyGem

feet, japanese, cumshot, cute, sperm, handjob
08:04 84%

Trained to Be a Submissive Slut

1 year ago

AShemaleTube

stockings, shemale, blowjob, train, anal, ladyboy, cum in mouth
34:54 88%

Gorgeous tgirl Angel dildo training

1 year ago

AShemaleTube

train, anal, big tits, dildo, masturbation, ass, toys
03:35 74%

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

7 months ago

TrannyGem

handjob, cute, femdom, facesitting, crossdresser, cosplay, femboy
09:34 67%

Dude Transformed Into damsel to Go Clubbing

3 weeks ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, british, shemale and girl
18:53 73%

Female dominance IDEAS - TOP 10 bonus

1 month ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
28:06 59%

SADISM & MASOCHISM Sissy fellate instructing with clyster!

10 months ago

TrannyGem

shemale, blowjob, train, instruction, fetish, bondage, BDSM
12:52

Feminization, cumload, ts

1 week ago

XXXVogue

BBC, swallow, black, shemale, sissy, big cock
04:34 83%

Sissy blows a load inwards undies

8 months ago

TrannyGem

femdom, teen (18+), creampie, train, big ass, teen anal (18+), crossdresser
07:05 84%

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

11 months ago

TrannyGem

femdom, teen (18+), emo, 18, dirty talk, cumshot, goth
15:07 52%

BBC plays with caged sissy queen Christinewest120

5 months ago

XXXVogue

black, train, bondage, BDSM, british, bareback, BBC
03:19 76%

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

1 year ago

TrannyGem

femdom, shemale, french, strapon, train, fetish, crossdresser
08:14 59%

We Worship your Cock! (cocksucking and Sissy PMV)

7 years ago

TrannyGem

train, short hair
07:29 53%

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

10 months ago

XXXVogue

beauty, public, train, dildo, crossdresser, swallow, big cock
11:20 13%

Making You a feeble Soy fellow Sissy

3 weeks ago

HDSex

teen (18+), shemale, POV, train, lingerie, ladyboy, crossdresser
42:54 45%

My Path to Life as A Sissy Hoe

6 years ago

TrannyGem

train, whore, sissy, compilation, threesome, blonde
07:10 71%

Trans sweetheart Gets boinked and Then comebacks the Favor

2 weeks ago

ShemaleTaxi

teen (18+), shemale, train, anal, teen anal (18+), bondage, crossdresser
13:44 86%

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

8 months ago

ShemaleTaxi

beauty, train, anal, big ass, orgasm, dildo, crossdresser
07:31 59%

Transgender mom, young petite, sissy feminization

2 months ago

XXXVogue

amateur, mom, indian, beauty, shemale, train, asian
03:04 56%

CHINESE TRANSGIRL LEITAOXIV DANCING UNTIL SHE SPUNK

1 year ago

TrannyGem

cute, thai, dance, asian, japanese, crossdresser, chinese
06:08 86%

Rigid Ass-Fuck Penetrate; Sissy; Female Dominance

4 years ago

TrannyGem

femdom, strapon, train, milk, crossdresser, whore, pegging
14:07 87%

Elf femboy in chastity belt gets tight bootie stretched by bbc cock and nail machine until jism

7 months ago

ShemaleMovie

beauty, train, dildo, 18, babe, ass, toys
12:37 51%

Parent gets super-naughty while sissy does cowers

4 years ago

TrannyGem

train, chubby, teen anal (18+)
10:04 80%

Trans Sissy Slut French Maid Service Training

8 months ago

AShemaleTube

shemale, french, train, fetish, maid, ass to mouth, slut
07:22 82%

Sissy Popper Training 1

5 years ago

BeMyHole

train, sissy, shemale
07:48 56%

Sissification Feminization Reprogramming Female Domination POINT OF VIEW Brainwashed Sissy Mindfuck

2 years ago

TrannyGem

femdom, fetish, crossdresser, JOI, sissy, femboy
15:35 69%

Sissy Hypno #2: Becoming A Cock Slut

5 years ago

xHamster

train, sissy, creampie, black
22:45

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

1 month ago

ShemaleTaxi

pissing, feet, pantyhose, latex, train, huge dildo, outdoor
12:29 74%

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

5 years ago

TrannyGem

femdom, train, tease, bondage, chastity
07:35 82%

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

8 months ago

ShemaleTaxi

latex, train, orgasm, bondage, crossdresser, cumshot, jerking
05:53 60%

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

1 year ago

ShemaleMovie

amateur, creampie, train, BDSM, crossdresser, facial, cum in mouth
22:45 82%

Amateur Couple and Trans - Train

1 year ago

xHamster

teen (18+), train, threesome, couple, teen anal (18+), sissy
20:49 89%

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

4 years ago

TrannyGem

femdom, latex, strapon, bisexual, train, bondage, BDSM
11:33 87%

Feminization Sissification Sissy Threesome Training Blowjob

1 year ago

HClips

blowjob, POV, train, threesome, tattoo, sissy
02:25 71%

I do everything which me say my holder, including fellatios on public place. I am enslaved sissy hoe

2 years ago

TrannyGem

public, sissy, crossdresser, beauty, outdoor, reality
28:06 92%

Ryu Nymph Stretches her Arse with a Monster can

4 years ago

TrannyGem

small cock, train, anal, boots, big tits, monster, ass
11:28 90%

Mistress and bbc train sissy in chastity

1 year ago

AShemaleTube

sissy, BBC, chastity, femdom, train
09:55 59%

AmberSis - Sissy whore

6 years ago

ShemaleMovie

creampie, train, crossdresser, creampie compilation, compilation, prostitute, whore
05:06 20%

Fellow Feminized by roomie as Discipline

1 week ago

ShemaleTaxi

shemale, strapon, anal, big ass, lingerie, BDSM, crossdresser
10:21 69%

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

9 months ago

TrannyGem

shemale, train, huge dildo, instruction, fetish, fisting, 18
11:24 61%

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

9 months ago

ShemaleTaxi

french, train, doctor, nurse, couple, bondage, maid
05:48 72%

Egyptian cuckold mother caught stepson in underwear

1 year ago

ShemaleMovie

arab, bisexual, train, cuckold, crossdresser, husband, caught
02:01 95%

I cant help it when Ive got a man meat up my bootie

4 years ago

TrannyGem

train, prostate, massage, orgasm, milk, toys, machine
08:31 72%

Sissy Training! 9 Min

3 years ago

TXXX

mature, shemale, sissy, domination, train
06:29

Ladyboy Trans Blowjob Training!

1 month ago

$$ FapHouse

handjob, bisexual, sissy, german, train
12:29 82%

Dominatrix Trains two Sissy Slaves

6 years ago

ShemaleZ

train, sissy, fetish
03:11 71%

51cm John Thomas Henry Humungous Assfuck Destruction Fuck Stick Slamming Deep into Slick Nice Femboy Asspussy

2 years ago

TrannyGem

huge dildo, dildo, hardcore, chastity
04:27 89%

The Only Way A Sissy Should Be Instructed To Jizz

2 years ago

TrannyGem

prostate, instruction, orgasm, milk, machine, sissy, anal orgasm
05:26 77%

Going knuckle deep the sissy mega-slut and rolen have fun piercings cock ball torture

2 years ago

TrannyGem

femdom, bondage, latex, fisting, piercing
21:13 81%

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

8 months ago

ShemaleTaxi

beauty, small cock, train, orgasm, ladyboy, babe, college
07:34 87%

Monster Mega butt plug. larissa1sexdoll sexy trans. Extreme insertions. Unique ass piercings.

2 years ago

xHamster

huge dildo, monster, sissy, insertion, dutch, dildo
18:28 75%

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

3 months ago

VideoSection

femdom, shemale, strapon, train, BDSM, whore, pegging
07:48 56%

TRANSSEXUAL Willow Hammerz - Snowbunny Sissy BNWO PMV

9 months ago

TrannyGem

interracial, cuckold, compilation, cumshot compilation, BBC, chastity
03:31 90%

Enormous black trouser snake plumbing sissy hoe Lola Crystals

3 years ago

TrannyGem

black, creampie, train, latina, crossdresser, slut, BBC
04:07 89%

Killer trans girly bone spunk rigid

1 year ago

TrannyGem

handjob, small cock, hairy, 18, cumshot, college, femboy
08:12 77%

When your sissy is missing parents rod

2 years ago

TrannyGem

dildo, crossdresser, riding, masturbation, slut, JOI, sissy
06:07 72%

Sissy Jessica Bloom Spitroast Teaching With Screwing Machine And Faux-cocks - Ass-fuck Sissygasms and Cumswallow

3 months ago

TrannyGem

train, huge dildo, anal, dildo, swallow, big cock, machine
27:39 78%

Trained to Be a Good Slut

1 year ago

$$ FapHouse

train, couple, lingerie, tattoo, facial, heels, bareback
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
05:04 88%

Russian transvestite fucks herself with a dildo (Part 1)

3 years ago

TrannyGem

teen (18+), train, russian, dildo, crossdresser, 18, sissy
12:29 68%

Blessed sissy dazed by numerous sissygasms railing phat 12.5”/32cm Fat Father fuck stick

1 year ago

TrannyGem

fat, train, huge dildo, orgasm, dildo, crossdresser, slut
08:04 71%

FAG Dirty Talk 22 SHEMALE CUM!

7 years ago

TrannyGem

train, dirty talk, cumshot compilation, JOI, sissy
03:07 82%

My homie toyed with me with a bang-out plaything

8 months ago

TrannyGem

cute, femdom, lesbian, train, fetish, orgasm, fisting
11:04 70%

Sissy Cum Swallow Training

4 years ago

TrannyOne

train, swallow, sissy
08:14 67%

Bbw sissy, white femboy, bbc fuck ladyboy

1 month ago

XXXVogue

black, train, couple, BBW, crossdresser, british, compilation
14:00 72%

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

1 year ago

TrannyGem

cute, teen (18+), train, 18, masturbation, blonde, slut
13:28 69%

SOUNDING WITH ELECTRIC TORMENT & BREATHPLAY FOR SISSY VICTIM

9 months ago

TrannyGem

cumshot, vibrator, bondage, latex
02:36 79%

Monster 12 BIG BLACK COCK Ravages Skinny Femboy Sissy Fuckslut

1 year ago

TrannyGem

ebony, black, train, anal, interracial, monster, big cock
18:22 66%

Sissy breezy Is What u Will Always Be

5 years ago

TrannyGem

cute, train, BDSM, spanking, clit, compilation, prostitute
06:18 86%

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

5 years ago

TrannyGem

train, swallow, wet, sissy
14:56 77%

Trans Gal Rika Fox Raunchy Bi-Racial POINT OF VIEW

1 year ago

TrannyGem

amateur, black, POV, train, anal, interracial, asian
06:13 92%

Femboy dancing and fapping with large penis

4 years ago

TrannyGem

train, dance, party, fetish, asian, orgasm, big tits
05:35 81%

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

4 years ago

TrannyGem

stockings, train, japanese, crossdresser, 18, teacher, college
10:51 54%

Guy Feminized by roomy as Discipline

1 year ago

ShemaleMovie

strapon, train, huge dildo, dildo, BDSM, crossdresser, full movie
15:39 94%

Whife *

6 years ago

TrannyGem

train, anal, bondage, crossdresser, cumshot, babe, ass
13:05 64%

Sissy Training with Mistress

7 years ago

TrannyGem

femdom, train, bondage, maid, BDSM, uniform, dress
03:55 67%

Domina feeding sissy humungous trunk

3 years ago

TrannyGem

femdom, strapon, lesbian, train, reality
07:47 75%

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

10 months ago

ShemaleTaxi

stockings, train, prostate, instruction, orgasm, dildo, cuckold
05:02 86%

Deep Fisting Compilation Real Sissy Training

3 months ago

HClips

amateur, public, train, outdoor, fisting, crossdresser, compilation
07:02 73%

Ria Bentley In Sissy Chastity Maid Service Training

4 months ago

ShemaleZ

stockings, train, maid, redhead, tattoo, group, sissy
05:41 57%

Feminization Sissification - Sissy teaching - FEEBLE SISSY BOY

3 years ago

TrannyGem

femdom, JOI, sissy
16:32 88%

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

5 years ago

TrannyGem

femdom, shemale, train, BDSM, shemale and girl, cumshot, big cock
05:51 92%

Chastity Sissy spunkslut Trains Her rectum And swallows Her Own Cum, Multiple Prostate Orgasms

1 year ago

ShemaleMovie

train, prostate, orgasm, fisting, dildo, crossdresser, british
06:38 64%

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

5 years ago

TrannyGem

public, voyeur, train, flashing, caught, sissy, skirt
20:41 70%

Sissy Poppers Hypnose training IV

5 years ago

ShemaleTaxi

train, sissy, shemale
10:17

Trans Gwen Tennyson Receives Gape assfuck Sex and the fattest internal ejaculation of Her Life

4 days ago

ShemaleTaxi

shemale, crossdresser, creampie, femboy, teen anal (18+), dildo, amateur
18:30 71%

Just because I can..

9 months ago

ShemaleTaxi

latex, train, bondage, BDSM, crossdresser, heels, sissy
11:52 65%

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

1 year ago

BeMyHole

domination, sissy, BBC, cartoon, big cock, train
03:12 61%

Feminization - Sissyfication - Sissy instructing - Support for the sissy FRESH

2 years ago

TrannyGem

instruction, compilation, cumshot compilation, JOI, sissy, chastity
27:04 60%

Actual Training at the Sissy Institute

4 months ago

$$ FapHouse

bondage, sissy, shemale, BDSM, masturbation, dildo
08:14 82%

My thickest anal dildo training session

5 months ago

XXXVogue

french, train, huge dildo, anal, dildo, lingerie, solo
05:14 80%

Mistress gives her caged sissy a little spanking for obedience training

6 months ago

XXXVogue

femdom, small cock, german, train, bondage, BDSM, crossdresser
05:20 81%

Trans ravaged pipe

1 year ago

TrannyGem

handjob, cute, fetish, orgasm, fisting, bondage, japanese
05:35 76%

Public piss and sissy training

1 year ago

ShemaleMovie

pissing, public, teen (18+), shemale, train, teen anal (18+), outdoor

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