SHEMALE • SISSY TRAINING 699 videos

Popular Latest Top rated

31:01 79%

Dutch, femboy anal, used hard

4 months ago

XXXVogue

amateur, beauty, public, train, anal, outdoor, dildo
39:26 82%

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

6 months ago

ShemaleTaxi

amateur, beauty, train, huge dildo, fisting, dildo, ladyboy
18:28 80%

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

4 years ago

TrannyGem

stockings, femdom, strapon, lesbian, train, fetish, bondage
15:04 69%

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

4 years ago

TrannyGem

handjob, mature, femdom, mature anal, train, granny, fetish
42:54 45%

My Path to Life as A Sissy Hoe

6 years ago

TrannyGem

train, whore, sissy, compilation, threesome, blonde
17:13 52%

Sissy Dani Firm Buttfuck Teaching PT two (Moist Audio)

1 year ago

TrannyGem

teen (18+), train, crossdresser, british, 18, whore, slut
22:45 82%

Amateur Couple and Trans - Train

1 year ago

xHamster

amateur, teen (18+), train, threesome, couple, teen anal (18+), sissy
34:54 88%

Gorgeous tgirl Angel dildo training

1 year ago

AShemaleTube

train, anal, big tits, dildo, latina, masturbation, ass
15:35 69%

Sissy Hypno #2: Becoming A Cock Slut

5 years ago

xHamster

train, sissy, creampie, black, domination, slut
28:06 59%

SADISM & MASOCHISM Sissy fellate instructing with clyster!

11 months ago

TrannyGem

shemale, train, instruction, fetish, bondage, BDSM, double anal
29:44 65%

Mature, crossdressing, amateur

3 months ago

XXXVogue

mature, french, blowjob, train, party, BDSM, ladyboy
1:02:22 69%

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
15:07 49%

BBC plays with caged sissy queen Christinewest120

6 months ago

XXXVogue

train, bondage, BDSM, british, bareback, BBC, sissy
18:22 65%

Sissy breezy Is What u Will Always Be

5 years ago

TrannyGem

cute, train, BDSM, spanking, clit, compilation, prostitute
18:53 60%

Female dominance IDEAS - TOP 10 bonus

2 months ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
22:45

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

3 months ago

ShemaleTaxi

pissing, feet, pantyhose, latex, train, huge dildo, outdoor
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
28:06 91%

Ryu Nymph Stretches her Arse with a Monster can

5 years ago

TrannyGem

train, anal, boots, big tits, monster, masturbation, ass
20:41 71%

Sissy Poppers Hypnose training IV

5 years ago

ShemaleTaxi

train, sissy, shemale
15:15 76%

TS Anna Katt Prepares Lilys Ass for Cock

7 years ago

TrannyGem

small cock, lesbian, train, anal, dildo, glasses, reality
15:39 94%

Whife *

6 years ago

TrannyGem

train, anal, bondage, ladyboy, crossdresser, cumshot, babe
19:58 83%

Marissa Minx And Sissy Tanya Ts Mistress Sissy Training

5 years ago

ShemaleZ

handjob, femdom, latex, train, fetish, crossdresser, domination
18:28 67%

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

4 months ago

VideoSection

femdom, strapon, train, BDSM, whore, pegging, sissy
17:29 90%

TS Schoolgirl Sasha Helps you Learn about Shemale Anatomy

7 years ago

TrannyGem

train, instruction, british, dirty talk, small tits, JOI, sissy
17:41 73%

Sissy Pussy Training

5 years ago

xHamster

beauty, public, creampie, train, masturbation, bareback, JOI
16:32 87%

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

5 years ago

TrannyGem

femdom, shemale, train, BDSM, shemale and girl, cumshot, big cock
27:03 80%

Playtime 69

6 months ago

ShemaleTaxi

train, couple, lingerie, british, facial, cumshot, 69
18:30 68%

Just because I can..

11 months ago

ShemaleTaxi

latex, train, bondage, BDSM, crossdresser, heels, sissy
20:10 74%

Ass fucking Update two: queen Edition!

1 year ago

ShemaleMovie

beauty, stockings, train, dildo, solo, ass, toys
58:16 75%

Young goth femboy anal training

1 year ago

AShemaleTube

homemade, small cock, train, anal, big tits, big cock, goth
21:13 81%

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

9 months ago

ShemaleTaxi

beauty, small cock, train, anal, orgasm, ladyboy, babe
1:02:24 65%

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

1 year ago

ShemaleTaxi

train, anal, ass, bareback, skinny, taxi, sissy
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, stepmom, domination, skinny
15:46 75%

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

1 year ago

ShemaleMovie

shemale, strapon, train, BDSM, crossdresser, husband, ass
17:09 60%

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

2 years ago

ShemaleMovie

train, instruction, 18, full movie, BBC, sissy
19:52 66%

Feminizaton - Sissy Instructing - COSMIC SISSY FATE

2 years ago

TrannyGem

instruction, compilation, dirty talk, cumshot compilation, JOI, BBC
16:06 88%

OIivia Jade - Sissy Training

1 month ago

AShemaleTube

sissy, shemale fucks guy, shemale, cumshot, stockings
1:24:42 76%

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

1 year ago

VideoSection

homemade, bisexual, train, BDSM, crossdresser, toys, domination
26:34 85%

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

5 years ago

BeMyHole

femdom, train, sissy
26:05 61%

PLUMPER Trans Biotch Buttfuck and Deep Throat Teaching

2 years ago

TrannyGem

BBW, dildo, shemale and girl, sissy, femboy
23:19 80%

Sissy Trained And Owned By BIG BLACK PENIS Bull

4 years ago

Analdin

train, anal, BDSM, deepthroat, penis, BBC, sissy
24:19 56%

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

1 year ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
20:51 56%

Turning the staright boys faggot

4 years ago

TrannyGem

femdom, train, mature, sissy
1:27:33 65%

Sissy in Training

7 years ago

xHamster

train, domination, sissy, shemale
17:44 91%

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

8 months ago

ShemaleMovie

femdom, shemale, strapon, train, anal, flashing, BDSM
23:35 20%

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

8 months ago

XXXVogue

train, satin, bondage, maid, dildo, crossdresser, toys
21:55 50%

Sissy Poppers Hypnose training III

5 years ago

ShemaleTaxi

train
20:51 81%

Turning the staright dudes homo

4 years ago

TrannyGem

mature, femdom, train, british, sissy, crossdresser
24:40 71%

Lady Nina - Sissy Maid Training (Full video - HD)

6 years ago

TXXX

train, fetish, maid, sissy
27:04 60%

Actual Training at the Sissy Institute

5 months ago

$$ FapHouse

bondage, sissy, shemale, BDSM, masturbation, dildo
26:38 79%

Trained to Be Completely Subservient to Him

1 year ago

$$ FapHouse

black, train, interracial, bareback, sissy, hardcore
23:09 75%

Mistress training sissies to play together

7 years ago

ShemaleZ

femdom, train, sissy
16:47 33%

Inhale My Femboys Dick (with Lina Lux)

8 months ago

TrannyGem

femdom, shemale, blowjob, POV, train, fetish, asian
23:19 87%

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

3 years ago

ShemaleZ

black, POV, train, interracial, gangbang, penis, BBC
27:39 78%

Trained to Be a Good Slut

1 year ago

$$ FapHouse

train, couple, lingerie, tattoo, facial, heels, bareback
20:21 79%

Forced By Step Mommy Sissy Enema And Anal Training

2 years ago

ShemaleZ

mom, sissy, stockings, train, fetish
25:17 83%

Sissy Fuckdoll Delivery

5 years ago

TrannyGem

train, bondage, BDSM, bikini, reality, slut, sissy
34:35 50%

Sissy Trainer - Dressmeuptoplay Sissy Boi Gif Training

9 years ago

ShemaleZ

train, sissy
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
29:51 53%

30 mins no break fellate spitroast contest!

10 months ago

TrannyGem

double anal, contest, gangbang, deepthroat, heels, secretary, slut
20:59 53%

White Sissy Virginity Instructing (Smash Machine)

10 months ago

TrannyGem

femdom, teen (18+), instruction, fetish, teen anal (18+), bondage, BDSM
16:02 53%

T-GIRL JIZM COMPILATION STAMINA COMPETE - Can you make it to the end ?

12 months ago

TrannyGem

train, orgasm, shemale and girl, compilation, masturbation, ass, cumshot compilation
16:02 53%

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
18:36 78%

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

4 years ago

TrannyGem

train, dogging, sissy, crossdresser
49:26 58%

Petra,s 9th training

1 year ago

xHamster

train, dildo, dutch, sissy, hardcore, femboy
32:02 63%

Hot sluts sucks gigantic dicks

5 years ago

XoZilla

femdom, train, fetish, tease, slut, JOI, sissy
21:15 82%

Sissy Training With Bailey Love

3 years ago

HClips

shemale, train, sissy, amateur
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
22:39 82%

Sissy Crossdresser - Amateur Couple And Trans - Train

1 year ago

ShemaleZ

stockings, teen (18+), POV, train, threesome, couple, redhead
26:50 82%

Jeni Justice Trained And Turned Into A Sexy Sissy

2 years ago

ShemaleZ

stockings, big ass, sissy, train
24:48 46%

Assfuck contest FOR SISSY

3 years ago

ShemaleTaxi

train, contest, taxi, sissy, femboy
41:04 53%

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

9 months ago

XXXVogue

dildo, futanari, sissy, mom, shemale, train
15:39

Femboy Rails Firm and Bangs an Rump with a Immense Fuck Stick and Gets an Rectal Ejaculation

5 years ago

TrannyGem

train, prostate, orgasm
28:54 83%

Sissy trains asshole for REAL COCKS (DAP)

3 years ago

IcePorn

stockings, train, solo, toys, asshole, sissy
21:18 88%

Fresh fucktoy training For A Shackled Sissy by Mistress Mercer

7 months ago

VideoSection

femdom, train, bondage, dildo, BDSM, sissy, gape
20:14 90%

Sasha Desade In Sissy Fuck Training

4 years ago

ShemaleZ

train, threesome, lingerie, sissy, chastity, brunette
32:24 70%

Sissy whore pic Bombardment Conversion Therapy

6 years ago

ShemaleTaxi

train, crossdresser, whore, taxi, sissy
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
28:27 71%

TPP Sissy hypnosis

1 year ago

ShemaleMovie

sissy, compilation, cumshot compilation, big cock, cumshot
56:10 50%

Sissy bi-atch Late Evening Supper

2 years ago

ShemaleTaxi

POV, train, orgasm, crossdresser, close up, kitchen, nylon
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
22:31 94%

Ryu Woman Takes Glowing Sinnovator 20in Deep

5 years ago

TrannyGem

amateur, train, dildo, machine, sissy, gape
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
18:14 11%

Sissified Masturbation Mindfuck [extreme Poppers]

7 years ago

TrannyGem

train, nipples, masturbation, dildo
17:32 60%

Sissy bbc training Encouragement Crossdresser bi-racial Fiona Fortune

9 months ago

HDSex

black, train, crossdresser, creampie compilation, compilation, BBC, sissy
33:06 88%

SISSY Mindcontrol instructing - Sasha de Sade & domina whisper

1 year ago

ShemaleMovie

femdom, teen (18+), train, instruction, maid, BDSM
18:49 49%

Sissy breezy Jenni needs bbc mega-slut Training

4 years ago

ShemaleTaxi

train, slut, taxi, BBC, sissy, black
46:20

Femmes Pub Gig six: A Sissy Feminization Series

5 years ago

TrannyGem

femdom, smoking, train
21:33 60%

Sissy Poppers Hypnose Training III

5 years ago

BeMyHole

train, sissy
17:33 46%

Sissy Training Encouragement Crossdresser BBC Anal Fiona Fortune

10 months ago

AShemaleTube

creampie, train, interracial, creampie compilation, compilation, cumshot compilation, BBC
19:37 63%

Sissy Whore Training 3 - The Best

5 months ago

HClips

amateur, stockings, train, whore, sissy, toys
39:29

Miss Abernathys Maid training

11 months ago

AShemaleTube

solo, sissy, amateur, latex, domination, maid
27:21 58%

TS in Training

11 months ago

$$ FapHouse

mature, latex, mature anal, train, spanking, toys, sissy
30:41 67%

Submissive Ladyboy Anal Casting & Slave Training

1 year ago

$$ FapHouse

casting, teen (18+), creampie, train, couple, teen anal (18+), ladyboy
19:45 80%

Sissy Hypno Training

2 years ago

AShemaleTube

anal, lingerie, crossdresser, sissy
18:41

Cdzinha, ass fucking, hypnosis

1 month ago

XXXVogue

creampie, train, crossdresser, creampie compilation, compilation, orgy, BBC
22:12 66%

Rubbish Gamers two (Every Gamers Wish)

3 years ago

TrannyGem

party, dress, cartoon, futanari, sissy
40:47 60%

Shemale porn, french trans, the big dick bitch

3 months ago

XXXVogue

french, train, BDSM, facial, prostitute, heels, selfsuck
15:28

Rides, sissy doll, hd videos

3 months ago

XXXVogue

doll, train, bondage, maid, BDSM, crossdresser, riding
39:45 40%

Submissive Asian Ladyboy Anal Casting & Slave Training

10 months ago

$$ FapHouse

casting, train, fisting, BDSM, sissy, 18, asian
15:21 81%

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
20:00 67%

Sissy Poppers Hypnose Training IV

5 years ago

BeMyHole

train
23:32

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

6 years ago

xHamster

train, sissy
53:13 67%

Petra,s 10th teaching

2 months ago

ShemaleTaxi

amateur, stockings, train, huge dildo, anal, ass to mouth, ass
26:11 67%

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
20:59 62%

Breezy Teaching Jizz Slurping two

4 years ago

TrannyGem

train, swallow, riding, JOI, 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
31:08

Is Sissy well-prepped for the giant Game

3 months ago

ShemaleMovie

sissy, shemale, POV, train
16:07

Sissy coming home from work

5 months ago

TrannyGem

homemade, anal, outdoor, cuckold, whore, slut, sissy
33:17 83%

Sissy Maid Covered with Fake jizz and violates Her fuckin Machine Before Having a Sissygasm

1 year ago

ShemaleMovie

shemale, sissy, anal, dildo, crossdresser, machine
25:34 83%

Assfucking Pummeling Machine - Compil 15

2 years ago

TrannyGem

french, swinger, train, fetish, BDSM, creampie compilation, compilation
15:24 79%

Sissy trainning

9 years ago

TXXX

train, sissy
25:04 89%

Dizzy In demeaning Sissy Maid teaching!

1 year ago

ShemaleMovie

strapon, train, bondage, maid, dildo, BDSM, domination
21:01 60%

TRANSSEXUAL Silly Female Dom Honeypot Whips Blond Cable Kitten

4 years ago

TrannyGem

train, bondage, BDSM, 18, sissy, shemale and girl
1:25:37

Petra's final check-up (incl piss drinking, fisting and more)

1 year ago

ShemaleTaxi

pissing, train, huge dildo, fisting, dildo, swallow, bareback
1:09:32

Petras pornography marathon part 1-three

1 year ago

ShemaleMovie

train, fisting, dildo, crossdresser, heels, toys, BBC
34:48 40%

Ana Lisa 32

2 years ago

xHamster

mature, latina, sissy, mexican
27:01 20%

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
28:09 77%

I leave my clothes behind and rail a immense faux-cock at a teach station park and road

4 years ago

TrannyGem

public, train, gagging, huge dildo, dildo, mask, clothed

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