SHEMALE • TEACHING 1,334 videos

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03:07 70%

Wife teaches and trains feminised sissy husband to become a BBC slut

2 years ago

AShemaleTube

train, interracial, wife, husband, shemale and girl, slut, BBC
05:55 70%

Drilling A stud In The teach

1 year ago

ShemaleMovie

shemale fucks guy, creampie, shemale, anal
07:55 70%

Tranny MILF Giovana Portylla Teaches A Guy How To Top

3 years ago

BeMyHole

mature, mature anal, latina
14:35 70%

TRANSFIXED - Femdom Emma Rose Teaches Babes BDSM Humiliation Using Fully Submissive Lauren P

2 years ago

AShemaleTube

BDSM, domination, shemale, pantyhose, femdom
09:52 70%

Girl Teaches a Nerdy Guy How to Suck a Big Trans Dick - Couple Shares the TS Cock

1 year ago

$$ FapHouse

teen (18+), blowjob, threesome, couple, 18, big cock, cum in mouth
05:50 70%

Asian shemale doctor teaches her MILF nurse a couple of fuck tricks

3 years ago

AnySex

doctor, asian, MILF, uniform, nurse
21:37 69%

Cumslut Teaching Sesh 1

4 years ago

TrannyGem

dirty talk, JOI, shemale and girl
08:15 69%

Sissy Femboy Restrain bondage Feminization Teaching

1 year ago

KeekAss

bondage, sissy, femboy, shemale
15:00 69%

Asian Tranny Angel Ass fucked in the kitchen - Let Me Teach You starring Venus Lux

3 years ago

xTits

handjob, creampie, spanking, kitchen, small tits, missionary
27:38 68%

Sissy sub firm teaching

3 years ago

ShemaleMovie

amateur, crossdresser, sissy
24:47 67%

Bianca Black, Bia Black And Sydney Summers In Teaches How To Fuck!

5 months ago

ShemaleZ

small tits, shemale, shemale and girl, black, tattoo, brunette
13:42 67%

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

5 years ago

TrannyGem

femdom, train, wife, orgasm, chastity
03:16 67%

Sissy teaching with and sans virginity

4 years ago

TrannyGem

train, cartoon, hands free, chastity
05:14 67%

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

11 months ago

XXXVogue

amateur, sissy, beauty, babe, train
10:42 67%

My trans stepmom teaches me how to suck cock

1 year ago

AShemaleTube

cum in mouth, stepmom
02:09 67%

Corporate Teaching two - trailer for futa flick

2 years ago

TrannyGem

cumshot, creampie, cartoon, futanari, shemale and girl
53:13 67%

Petra,s 10th teaching

4 months ago

ShemaleTaxi

amateur, stockings, train, huge dildo, anal, ass to mouth, ass
06:14 67%

Tramp marionette teaching

8 months ago

ShemaleTaxi

shemale, cumshot, amateur, beauty, ladyboy, swallow
10:13 67%

Teaching The Married Man How To Fuck An Ass FREE

11 months ago

BeMyHole

amateur, kissing, bride, small cock, anal, dogging, ass to mouth
10:25 67%

Sissy transgender princess teaches her uber-cute ass!!!

1 year ago

ShemaleMovie

amateur, cute, teen (18+), french, train, teen anal (18+), double anal
07:12 67%

Trans Ria Bentley teaches StepDaughter Eden Espi For buttfuck intercourse

1 year ago

ShemaleMovie

skinny, bareback, massage, femboy, kissing, train
08:06 67%

Black And Beautiful Professor Teaches You How To Please Her

7 months ago

ShemaleZ

shemale, black, solo, beauty
34:40 67%

Angelina Satiate-The Trans Teach - Spencer Bradley

9 months ago

KeekAss

threesome, shemale, big ass, handjob
09:02 67%

Transgender chick fucks her acquaintance on the teach

1 year ago

ShemaleMovie

public, train, tattoo, crossdresser, masturbation
09:10 67%

20 Inches Deep! Sissy Maid extraordinary Deep anal invasion teaching Jessica Bloom

1 year ago

ShemaleMovie

small cock, huge dildo, maid, dildo, british, babe, cum in mouth
06:21 67%

Sissy Russian Trainer - strap on dildo teaching (nstshemale, Rus Text, Voices)

2 years ago

ShemaleTaxi

strapon, russian, sissy, compilation
12:28 67%

TRANSSEXUAL Sissy Doofy Buttfuck Gape Teaching Part trio

5 years ago

KeekAss

skinny, sissy, gape
05:32 66%

Robin D Teach

3 years ago

ShemaleZ

solo
12:49 65%

Mrs Lovings Knicker Strangling Teaching

4 years ago

TrannyGem

train
20:34 64%

Bwc Teaches Schoolboy A Hard Lesson

4 years ago

Upornia

big cock, amateur
08:15 64%

Teaching My Ts Stepdaughter How To Fuck - Adira Allure And Avery Lust

9 months ago

ShemaleZ

MILF, shemale and girl, ass licking, blowjob
11:32 64%

MatureNL - naughty bbw Step mom Teaches Her Horny Stepson a Lesson!

2 years ago

ShemaleTaxi

BBW, blowjob, mom, stepmom
11:28 64%

Assfucking Teaching with Robin Banks and miss Jane

6 years ago

KeekAss

shemale, fetish, toys, webcam, small tits, amateur
06:26 64%

Busty nun with a huge dick teaches a teen to be submissive

3 years ago

YourLust

teen anal (18+), uniform, nun, cartoon
12:34 63%

Submissive teaching with nipple play and pain tolerance featuring Allywhorefrost

11 months ago

XXXVogue

BDSM, compilation, nipples
06:32 63%

Teaching rich Lardass for my phat nymph cock

1 year ago

ShemaleMovie

stockings, shemale, blowjob, BDSM, shemale and girl, big cock, domination
19:22 63%

After teaching, can you keep this secret?

5 years ago

TrannyGem

3D, anime, futanari
06:48 62%

Brunette mistress teaches cuckold sissy slave to dick sucking nice cock

5 years ago

TrannyOne

femdom, cuckold, sissy
26:00 62%

Sissy Lilly and her teaching

5 years ago

ShemaleTaxi

sissy
20:59 62%

Breezy Teaching Jizz Slurping two

4 years ago

TrannyGem

train, swallow, riding, JOI, sissy
05:41 62%

Feminization Sissification - Sissy teaching - FEEBLE SISSY BOY

3 years ago

TrannyGem

femdom, JOI, sissy, train
07:13 62%

Cherry Aleksa & Vincent Vega teach young stud some kinky tricks in bed

2 years ago

Sexu

mature, russian, MILF, short hair, shaving, small tits, stranger
10:12 62%

Brittney Kade And Khloe Kapri - My Trans Stepmom Teaches Me How To Suck Cock

1 year ago

ShemaleZ

18, cum in mouth, big cock, stepmom
07:29 60%

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

1 year ago

XXXVogue

public, train, dildo, crossdresser, swallow, big cock, babe
13:42 60%

Teaching my sub for blow

1 year ago

TrannyGem

femdom, train, gagging, fetish, bondage, BDSM, deepthroat
07:35 60%

Sissy Elf ladyboy In A bondage & discipline Feminization teaching

11 months ago

HDSex

beauty, train, bondage, BDSM, ladyboy, crossdresser, babe
07:13 60%

Cherry Aleksa teaches young stud some kinky sex tricks in bed with her mature pussy

2 years ago

HogTV

russian, wife, short hair, stranger
15:39 60%

Mama Studio Presents Teaching My Step Cousin To Eat A Trans For The First Time - Free

6 months ago

BeMyHole

mom, blowjob, creampie, big ass, MILF, latina, ass to mouth
10:14 60%

Trans Sissy tramp French Maid Service teaching

10 months ago

ShemaleMovie

shemale, french, sissy, cumshot, facial, train
08:00 60%

H*s*m-047 Hime.love Next Level Ill Teach You Discipline Your Dick And Anal Decensored With Yagami Noa

12 months ago

PePorn

shemale, japanese uncensored, asian, japanese
15:59 60%

Mature grandmother with Saggy Tits Teach blonde big natural Tits Teen how to bang with strapon at Old Young Lesbian Sex

8 months ago

ShemaleMovie

strapon, natural, shemale, lesbian, mature, saggy tits
46:02 60%

Petras 8th teaching (incl very first fist,fat dildo and more)

1 year ago

ShemaleTaxi

fat, huge dildo, fisting, BDSM, tied, riding, big cock
08:04 60%

Setsunas anal teaching sheer pleasure

1 year ago

ShemaleMovie

ladyboy, dildo, riding, creampie, asshole
10:56 60%

Sissy teaching for bimbo bitches

1 year ago

ShemaleTaxi

teen (18+), POV, train, crossdresser, machine, BBC, sissy
08:21 60%

Giant fuck stick ass-fuck teaching for Brit COUGAR Lisa and TGirl Gigi

1 year ago

TrannyGem

british, huge dildo, stockings, dildo, cougar, train
30:04 60%

Stellar Tgirl Riley teaching session #6 part I

1 year ago

ShemaleMovie

blowjob, lingerie, crossdresser, skinny, sissy, femboy
05:20 60%

Dirty bootie teaching sesh TRANSSEXUAL injection gape teaching

3 years ago

KeekAss

mature anal, toys, gape, mature, crossdresser
26:16 60%

Ass-fuck compete sissy teaching full length video

3 years ago

ShemaleTaxi

homemade, ladyboy, sissy
17:19 60%

Rectal teaching with monster black fuck stick. I want more!

3 years ago

KeekAss

monster, black
04:19 60%

Monstrous Muscle Elastic Backside Sissy Revealed at Teach Station Public Sissygasm

4 years ago

KeekAss

mature, public, muscle, crossdresser
19:27 60%

After Teaching THREE DIMENSIONAL Anime Porn Futa [honey Select 2]

5 years ago

KeekAss

lesbian, anime, futanari, japanese lesbian, japanese
29:42 60%

Sergeant Miles teaches Iliana how to be a fuck slut

6 years ago

ShemaleZ

18, slut
29:07 60%

Teaching str8 young boy first time ladyboy experience

9 years ago

ShemaleZ

ladyboy, first time
10:54 59%

SISSY Teaching Level 1, Buttfuck, cork, clysters, innocence, feminization, PUBLIC TART

1 year ago

KeekAss

shemale, sissy, public
46:01 58%

Petra,s 8th teaching

1 year ago

HDSex

anal, fisting, dildo, BDSM, spanking, toys, hardcore
27:51 58%

Cumslut Teaching Sesh 3A

4 years ago

KeekAss

solo, cumshot
08:00 58%

My tgirl stepmom agrees to teach me some

3 years ago

KeekAss

handjob, beauty, stockings, lesbian, stepmom, skinny, small tits
08:12 57%

Sex Therapist Teaches You to Edge

2 years ago

xHamster

amateur, beauty, big tits, solo, blonde, FTM
15:24 57%

Priscila Araujo Teaching How to Make a Man Happy

1 year ago

$$ FapHouse

shemale fucks guy, big cock, brazil
07:08 57%

SISSYGASM sans CUM SHOT is the Highest SISSIFICATION Level! Sissy Domme Veronica Taboo Teaching

1 year ago

TrannyGem

chastity, crossdresser, anal orgasm
13:03 57%

Futa University Hermaphroditism Manga Porn Game PornPlay Ep.two ladyboy edging teaching

3 years ago

KeekAss

ladyboy, masturbation, futanari, hermaphrodite
07:51 57%

Let Me Teach You

5 years ago

AShemaleTube

blowjob
1:05:38 57%

Sammy Teaches you how to cum twice!

5 years ago

xHamster

latex, JOI, solo
18:15 56%

Trans teaching her friend a good lesson

10 months ago

AShemaleTube

fetish, latina, crossdresser, domination, shemale fucks guy
26:05 56%

PLUMPER Trans Biotch Buttfuck and Deep Throat Teaching

2 years ago

TrannyGem

BBW, dildo, shemale and girl, sissy, femboy
07:55 56%

Assfucking teaching XXL backside ass-plug sesh

1 year ago

TrannyGem

pissing, farting, huge dildo, fetish, fisting, dildo, skinny
29:50 56%

Futa mom teaches her daughter how to suck and pump a pussy

5 years ago

XXXDan

mom, teacher, pump, futanari
02:43 56%

PREVIEW GREATEST SISSY VICTIM REAL TEACHING BY TRANSSEXUAL QUEEN OF MILK WITHOUT A CONDOM FELLATE SPUNK SMACKING GAG USE UTTER ON ONLYFANS

3 years ago

KeekAss

blowjob, gagging, milk, crossdresser, domination, sissy
21:19 56%

BBC T-beauty Teaching The First Timer A Sex Lesson

5 years ago

ShemaleZ

big cock, teacher, ebony
12:42 56%

Cute teen teached by Asian stepmom - Only Taboo

1 year ago

NuVid

ladyboy, cute, teen (18+), stepmom, asian
04:12 55%

After Teaching - Futa Trans Nymph boned in the Arse on tabouret

3 years ago

TrannyGem

3D, 18, old and young (18+), sport, reality, cartoon, gym
03:59 54%

She-Creature mother pulverizes her step son-in-law in the bathroom

1 year ago

TrannyGem

mom, MILF, 3D, 18, stepmom, old and young (18+), cartoon
16:16 54%

Shemale Lucy Hart teaches her cute slut April Olsen to play golf and fuck passionately

2 years ago

YourLust

shemale
11:19 53%

Headmistress Teaching Her Sissies

5 years ago

TrannyGem

femdom, domination, crossdresser
12:36 53%

Magnificent Jade Venus teaches Trand Bestie How To smash - Jade Venus, Tori Easton - GenderXFilms

4 years ago

ShemaleTaxi

handjob, small cock, deepthroat, small tits, taxi, missionary
06:04 53%

Teaching a tranny prostitute!

7 years ago

AShemaleTube

homemade, gangbang, prostitute
09:48 53%

Feminization Sissification Sissy teaching - WHO YOU ARE

3 years ago

TrannyGem

femdom, train, bondage, JOI, sissy
17:10 53%

The Art Of Temptation Educational Training Fuck-A-Thon Tempt Dame Ejaculations Learn

5 years ago

TrannyGem

train, tease, glasses, seduced, masturbation, skinny
09:07 52%

Self-teaching No. 95: Wearing Sanitary Napkins and Tampons for an Exposure Walk - Part 2

7 months ago

VideoSection

pissing, public, anal, outdoor, japanese, BDSM, crossdresser
17:13 51%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

1 year ago

TrannyGem

teen (18+), train, crossdresser, british, 18, whore, slut
04:56 50%

Sissy teaching diary - very first day

9 months ago

KeekAss

sissy, shemale, handjob
10:32 50%

Tgirl Teaching You to Suck Girlcock and Swallow Roleplay

11 months ago

$$ FapHouse

shemale, solo, ladyboy, swallow, 18
13:30 50%

Platinum-blonde femboy pummel machine sissy teaching!

2 years ago

ShemaleMovie

homemade, beauty, emo, train, dildo, machine, sissy
13:27 50%

Teaching my femboy Krizfemgirl how to be the ultimate maid with slaps and facesitting

10 months ago

XXXVogue

boots, BBW, maid, BDSM, facesitting, spanking, heels
17:07 50%

Trans boy teaches his femboy to spank him and jism in ass. Femboy needs more instructing.

2 years ago

ShemaleMovie

shemale, instruction, spanking, 18, femboy, cum in ass
06:59 50%

Ginger Hair, lingerie, bdsm teaching

1 year ago

VideoSection

latex, machine, stockings
15:44 50%

Voluptuous mom and teen jaw-dropping sex movie

3 years ago

XoZilla

mom, teen (18+), swinger, nurse, wife, teen anal (18+), MILF
52:06 50%

Transgender princesses in teaching - (Episode #01)

4 months ago

VideoSection

shemale, shemale fucks guy, ladyboy, thai
26:36 50%

Torrid egirl lad displays you her feet and teaches you how to touch yourself

2 years ago

ShemaleTaxi

feet, goth, femboy
04:31 50%

Stepmom Will Teach You How To Jerk Off Babe Joi 5 Min

3 years ago

ShemaleZ

stockings, stepmom, JOI, webcam, jerking
16:59 50%

Russian femboy opens up her cock-squeezing fuck-hole with a giant man-meat and jizzes super hot with no mitts ( ass-fuck teaching )

4 years ago

TrannyGem

cute, russian, teen anal (18+), dildo, 18, riding
10:48 49%

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

2 years ago

TrannyGem

train, compilation, dirty talk, cumshot compilation, JOI, BBC, sissy
14:35 48%

TRANSFIXED - Femdom Emma Rose teaches girls BDSM humiliation using totally submissive Lauren Phillips

2 years ago

XXXDan

orgy, group, femdom, babe, shemale and girl, BDSM
12:30 46%

Sissy teaching After first-ever Time Feminization

2 years ago

ShemaleMovie

latex, train, BDSM, crossdresser, domination, sissy, first time
30:21 45%

Ebony lesbian master teaching this little slut for good behaviour

4 years ago

TrannyOne

ebony, shemale, lesbian, slut
21:37 45%

Cumslut Teaching Sesh 1

4 years ago

KeekAss

crossdresser
26:19 45%

Coach ramon teaches tgirl kylie maria with his monster cock

6 years ago

ShemaleZ

uniform, monster, bareback, big cock, shemale
11:09 45%

BIG BLACK COCK GARGLE JOB TEACHING & MENTAL ENCOURAGEMENT - Sissy Kelly Frost

2 years ago

TrannyGem

fetish, BDSM, big cock, slut, BBC, chastity
28:43 44%

Queen Ivory In Transroommate - Trans Babe Teaches Roommate Bareback Lesson

1 year ago

ShemaleZ

handjob, shemale, babe, bareback
12:50 44%

Dyked - Beautiful Milf Teaches curious straight dame How To Eat Pussy

2 years ago

ShemaleMovie

BDSM, MILF, beauty, blonde, strapon, teen (18+)
48:25 43%

Lady Becky Teaches Sissy Slut Michelle How To Masturbate In A Proper Way

2 years ago

ShemaleZ

sissy, creampie, amateur, stockings, shemale
09:47 43%

SISSY SPIT ROAST teaching - Computer

8 years ago

ShemaleZ

sissy
20:20 42%

Teaching The Faggot Sissies How To Smoke & Worship My feet! bbw Mistress Tina Snua Smoking cigarettes & Dirty Talking

3 years ago

ShemaleTaxi

feet, femdom, voyeur, smoking, chubby, BBW, british
24:23 42%

Step mommy bangs stepson ass and teach cum while being humped

3 years ago

ShemaleTaxi

mom, strapon, huge dildo, fisting, cum in mouth, cum in ass
06:31 40%

TS mistress teaches the sexy TS babe her blowjob skills as she headfucks the nasty lad like a pro

5 years ago

TrannyOne

femdom
05:30 40%

BF teaches how to prepare ladyboys ass for BB anal fuck

6 years ago

ShemaleZ

teen (18+), teen anal (18+), ass, toys, bareback
11:59 40%

Teaching my SPANDEX SISSY whore GUTS with my NURSE MITTENS

8 months ago

TrannyGem

handjob, femdom, latex, prostate, nurse, massage, tease
07:02 40%

Femme Fatale Teaches A Lesson

1 year ago

Fuxxx

domination, nylon, clothed, ass to mouth
04:04 38%

JUDE LYNX — COLLEGE +barely legal NIGHT CUSHION EJACULATION FTM OMEGA GUY

11 months ago

TrannyGem

mom, public, big ass, asian, japanese, pregnant, korean
07:59 33%

H*s*m-047 Hime.love Yagami Noa Next Level Ill Teach You Discipline Your Dick And Anal Decensored

10 months ago

GetTranny

japanese uncensored, japanese, asian, shemale

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