SHEMALE • TRAIN 1,028 videos

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37:16

Shemale dildo hero - inflatable training

Yesterday

XXXDan

shemale
15:46

Blondealashes training

Yesterday

XXXDan

shemale, solo
47:00

One Day of Training in My Room

2 days ago

xHamster

japanese, solo, cute, asian
18:06

The magic hitachi helped the mistress wring out a pile of sperm from the guy

3 days ago

ShemaleMovie

sperm, amateur, BDSM, sissy, domination, shemale
26:51

Sissy Traning, Train Your Ass Like a Pro, and Be Always Ready for Real Cocks

4 days ago

xHamster

train
16:46

Sissy training with KatyKoroleva

6 days ago

xHamster

big cock, shemale, sissy, femboy
24:32

SIssy flashing her bum - public upskirt

1 week ago

TrannyGem

anal, sissy, public, crossdresser, big ass, femdom, flashing
15:55

New dame KYM VIRGINITIES LOST ON vid at The Sissy Institute

1 week ago

ShemaleTaxi

cumshot, teen (18+), sissy, teen anal (18+), shemale
15:41

Submissive ts anal training session

1 week ago

xHamster

dildo, solo, big ass
17:16

Feminization Sissy training Female energy for faggot

1 week ago

PornHub

solo, sissy, cumshot, blowjob
18:40

Aphrodite Adams trains You The stupid Basics

1 week ago

ShemaleMovie

shemale, POV, solo
26:25

My Girlfriend Trains My Anal And Does Handjob

1 week ago

ShemaleZ

stockings, BDSM, shemale and girl, shemale, amateur, anal
18:09

Sexy mouth bang training with a phat dildo as a warm-up. Sissy slave gets used rock-hard by 6 guys for 3 days.

2 weeks ago

ShemaleMovie

shemale fucks guy, shemale, sissy, beauty, dildo
23:51

Luxurious display. Dance, handjob, blowjob, vaginal penetration, slow buttfuck training. I wont cum with you.

2 weeks ago

ShemaleTaxi

anal, shemale, feet
20:17

Pussy Training

2 weeks ago

JizzBunker

hardcore, public, german, solo, mature
17:20

Deepthroat Blowjob Training and wax on jugs and nipples

2 weeks ago

ShemaleMovie

ladyboy, blowjob
16:57

Trans boy teaches his femboy to spank him and cum in ass. Femboy needs more training.

2 weeks ago

PornHub

amateur, shemale, french, creampie, anal, cumshot, ass
17:08

Scorching T-Doll with a Cock-Squeezing Rump Gets Machine Rode until She Pours Out (Fat Handsfree Jizz Shot)

3 weeks ago

TrannyGem

fat, train, huge dildo, orgasm, dildo, riding, babe
15:08

Training my sissy bitch by gagging her with a 9 inch cock and chockin

3 weeks ago

XXXDan

amateur, teen (18+), POV, couple, BDSM, swallow, big cock
45:38

Lily Rose Ray In Lilyrose Came Back And Trainning Her Fat Ass More Extrem 46 Min

3 weeks ago

ShemaleZ

train, shemale, stockings, fat
26:49

My girlfriend trains my anal and does handjob

3 weeks ago

PornHub

handjob, shemale, anal, bondage, 18, shemale and girl, small tits
15:08

POV: Virgin vampire girl Mavis Dracula trains her pussy before to have a rough sex with you

3 weeks ago

PornHub

shemale and girl
55:53

FREE PREMIUM VIDEO - Training this tight bussy Kendra Cutie

1 month ago

PornHub

solo, amateur, anal, shemale, train
16:24

Mischievous nymph secret night out✨It perceived so fine I pissed myself

1 month ago

TrannyGem

pissing, crossdresser, femboy, sissy, asian
16:40

Excellent lady plays tricks on her butthole late at night sans her Daddy prowess

1 month ago

TrannyGem

anal, japanese, sissy, masturbation, asian, crossdresser
16:18

Rump plugged emo attempts dual intrusion

1 month ago

TrannyGem

anal, emo, shemale and girl, masturbation
39:00

BIG COCK LATIN SHEMALE TOPS group sex bukkake spunk TRAIN

1 month ago

ShemaleMovie

bukkake, big cock, gangbang, shemale, group
15:25

She can use her humungous fake penis anywhere

1 month ago

TrannyGem

shemale, shemale and girl, japanese, public, toys
17:07

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

1 month ago

TrannyGem

mom, shemale, fat, anal, instruction, facesitting, shemale and girl
17:35

Hot Livi Dolls Ass Trained By Bbc

1 month ago

ShemaleZ

amateur, stockings, shemale, interracial, cumshot, BBC
23:41

Cosplay shemale riding a train of cocks in wild gangbang

1 month ago

PornLib

asian, japanese, gangbang, group, hardcore, cosplay
25:15

Francis Malice Sissy Dream 1

1 month ago

xHamster

big tits, shemale, german, solo, crossdresser
15:14

She-creature Julie Rouch ends up with a creampie After Anal Train Threeway

1 month ago

ShemaleTaxi

stockings, creampie, brazil, hardcore, train
16:22

Inked ladyboy Ruby Is trained Submissio - FULL VIDEO

2 months ago

VideoSection

beauty, shemale, ladyboy
15:08

JOI & ASMR Dream Trans Goth GF clicker trains you Pt.2

2 months ago

PornHub

shemale, train, 18, cumshot, masturbation, goth, JOI
16:28

Lady Alice compilation 06 Beauty and Sexuality (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR

2 months ago

xHamster

outdoor, MILF, strip, vintage, domination
51:55

Drone Pup Training

2 months ago

PornHub

pissing
19:45

Cute little trap anal training

2 months ago

AShemaleTube

shemale, sissy, femboy
25:31

Sissy training - Futa/hentai Brainwash

2 months ago

PornHub

creampie, futanari, sissy
26:05

PLUMPER Trans Biotch Buttfuck and Deep Throat Teaching

2 months ago

TrannyGem

shemale, blowjob, anal, BBW, dildo, sissy
22:03

JOI & ASMR Dream Trans Goth GF clicker trains you Pt.1

2 months ago

PornHub

amateur, teen (18+), solo, goth, JOI
26:04

BBW Trans Slut Anal and Oral Training

2 months ago

PornHub

amateur, shemale, blowjob, anal, BBW
30:53

Lizzy yum - daily anal training 2

2 months ago

JizzBunker

mature anal, huge dildo, orgasm, shower
20:14

Poon training

2 months ago

ShemaleTaxi

anal
22:12

Anal Toys - Whore Training

3 months ago

ShemaleZ

mature anal
19:44

Anal training with fucking machine and huge toys long version

3 months ago

XXXDan

small cock, huge dildo, anal, machine
31:32

Lizzy Yum, September 2023., ANAL TRAINING, view No. 2, orgasm after surgery, pussy masturbation

3 months ago

JizzBunker

mature anal, orgasm
17:38

Training My Sexy Sissy With 12 Inches Of rock-hard weenies gonzo Bondages Training

3 months ago

ShemaleTaxi

bondage
15:19

Long Sissy Training With anal invasion rod railing

3 months ago

ShemaleTaxi

sissy
18:42

Hypnosis BR - Porra no cú - BBCs Gigantes no rabo da Paula CDZINHA

3 months ago

ShemaleTaxi

crossdresser, creampie compilation, compilation, orgy, BBC, sissy
19:45

Sissy Hypno Training

3 months ago

AShemaleTube

anal, lingerie, crossdresser, sissy
18:37

Insane trans girl loves to get fucked in the butt with a thick dildo and cum hands free (training)

3 months ago

ShemaleMovie

cum in ass, dildo, train
22:41

Puppys Training time

3 months ago

PornHub

fetish, bondage
16:22

LizzyYum December 2023 Double Penetration Training (dual) Post Op Orgasm Pussy Masturbation Teasing

3 months ago

BeMyHole

orgasm, bath, bathroom
19:58

Slave Pups Bitch Hole Training

3 months ago

PornHub

pissing, bondage
1:16:23

Bondage & discipline female domination AI training

3 months ago

ShemaleMovie

homemade, bondage, domination
16:39

Lizzy Yum - December 2023 Double Penetration Training (dual) Post Op Orgasm Pussy Masturbation Teasing

3 months ago

ShemaleZ

orgasm
19:54

Sissy training

3 months ago

AShemaleTube

stockings, crossdresser, domination, sissy
42:59

Positive sissy brainwashing Sissy conversion Sissy training Sissy thinking Femboy Shemale Tranny

3 months ago

XXXDan

spanish, anal
17:19

Anal training with a monster black dildo. I want more!

3 months ago

JizzBunker

monster
33:59

Training is now complete

3 months ago

JizzBunker

mature
16:28

Restricted and trained in dress-up play.

3 months ago

JizzBunker

public, gagging, bondage, japanese, maid, dress, cosplay
28:57

Young amateur sissy femboy crossdresser anal gape training - part 1 of 2

3 months ago

AShemaleTube

sissy
50:30

Sissy femboy crossdresser anal gape training - part 2

3 months ago

AShemaleTube

sissy
17:02

Sissy Training day number two

3 months ago

XXXDan

public, train
16:26

Training program for women, part 6

3 months ago

JizzBunker

amateur
30:28

Lizzy Yum, September 2023., ANAL TRAINING, view No. 3, post-op orgasm, pussy masturbation

3 months ago

JizzBunker

mature anal, orgasm, shower, post op
34:48

Ana Lisa 32

4 months ago

xHamster

mature, latina, sissy
45:35

Listening to hypno training my sissy pussy in chastity like a good slut. Spit roast

4 months ago

AShemaleTube

chastity
33:37

Good anal training - Denise Humain

4 months ago

JizzBunker

german, dildo
30:07

Emo crossdresser on a walk at the train station. slut outfit

4 months ago

JizzBunker

small cock, public, emo, outdoor, crossdresser, heels, cosplay
17:15

Fisting training with machine

4 months ago

XXXDan

fisting, machine, cosplay, crossdresser
27:23

Her 43cm Black Deep Anal insertion - Pink Latex Bimbo Brandynette

4 months ago

PornHub

insertion
17:23

Bambi ass fucking trainer

4 months ago

ShemaleTaxi

indian, french, sissy
48:28

Shemale Brandy Loves Anal with Jason Follow Along with Us

4 months ago

xHamster

instruction, JOI
21:34

Gothic Witch romps trio Xxl Fuck Sticks

4 months ago

TrannyGem

huge dildo, dildo, sissy, gape, train
15:32 79%

Train

4 months ago

PornHub

amateur, japanese, masturbation, femboy
30:43

Tranny Training 2 - Scene 1

4 months ago

XXXDan

train
24:14

Tranny Train

4 months ago

BeMyHole

riding, shemale fucks guy, threesome
1:32:22

Brainwash Sissy Anal Masturbation Big ass Femboy Big Dildo Sissy mindset Sissy training Shemale Anal

4 months ago

PornHub

crossdresser
16:15

Sissy training

4 months ago

ShemaleTaxi

sissy
16:45

LizzyYum december 2023 double penetration training (dual) Post Op Orgasm Pussy Masturbation Teasing

5 months ago

xHamster

double anal, double penetration, post op
23:03

First time Sissy MixyXXX training FIST with hands free orgasm!

5 months ago

AShemaleTube

pantyhose, orgasm, fisting, first time, hands free
27:34

Jenny Kennedy - Trained To Be A Good Slut

5 months ago

ShemaleZ

slut, train
23:20

Sissy penetrates extraordinary long faux-cock and reaches a fresh private rectal record

5 months ago

TrannyGem

sissy
21:52

Petite Blue-hair Cutie Pleases Her Tranny Friend With Hot Fuck In the Train And Risky BJ In the Taxi

5 months ago

MyLust

public, train, russian
45:24

Take A Ride On The Trans Train - Khloe Kay, Casey Kisses And Jade Venus

5 months ago

ShemaleZ

kissing, stockings, shemale, train, threesome, MILF, riding
17:44

Sissy Bimbo Training

5 months ago

ShemaleZ

vintage
33:59

Training is now complete

6 months ago

xHamster

fetish
17:00

Feminization - Sissification - Sissy Instructing - Sissy Support - utter version - two

6 months ago

TrannyGem

POV, instruction, JOI
16:27

Young femboy anal training 1

6 months ago

AShemaleTube

18
15:38

Smoking Hy-pno sissy training 03

6 months ago

ShemaleMovie

blowjob, smoking, BDSM
18:55

Reality Sexy Shemale Fuck Girl In The Train

6 months ago

BeMyHole

public, shemale and girl
17:39

Maid cleans teachers palace

6 months ago

TrannyGem

femdom, public, train, upskirt, teacher, reality, sissy
27:06

A camper was waiting to watch my culo

6 months ago

TrannyGem

public, upskirt, sissy
17:35

Fantastic transmom train stepdaughter how to get men point of view jerk off instructions roleplay

6 months ago

TrannyGem

lesbian, JOI, dirty talk
22:25

Risky sex with sexy tranny in the train and in the car / Compilation

6 months ago

PornHub

handjob, amateur, public, flashing, car, compilation, blonde
18:13

Speculum training

6 months ago

ShemaleMovie

public
16:02

TRANSGENDER PRINCESS JISM COMPILATION STAMINA COMPETE - Can you make it to the end ?

6 months ago

TrannyGem

orgasm, compilation, cumshot compilation, orgasm compilation, sissy, anal orgasm
20:12

French Sissy Maid toying in her living apartment whil parents arent home

6 months ago

TrannyGem

teen anal (18+), dildo, gape
19:42

Slim femboy sissy training her smooth ass with a buttplug and big dildo

6 months ago

PornHub

russian, teen anal (18+), dildo, femboy
16:26

Training Program for sissies part 6

7 months ago

xHamster

solo
15:16

Virgin Becoming Pansy

7 months ago

TrannyGem

double anal
31:33 77%

Lucass Bi Slave Training

7 months ago

BeMyHole

train, 18, ass licking, domination, shemale fucks guy, hardcore
17:06

TGirl Gigi dildo fucked in the ass until she squirts lube out of her ass

7 months ago

PornHub

mature anal, huge dildo, squirt, orgasm, british, anal orgasm
25:34 90%

Assfucking Pummeling Machine - Compil 15

7 months ago

TrannyGem

french, train, BDSM, creampie compilation, compilation, machine, cumshot compilation
26:33

Aliza Breeze Trained To Be Completely Subservient To Hi - Liza Shay

7 months ago

ShemaleZ

ebony, interracial, big cock
17:16

Training For Male Slut

7 months ago

BeMyHole

public, blowjob, outdoor, domination, hardcore
30:00 75%

In Training With A Tran - Sinn Sage

7 months ago

BeMyHole

shemale, shemale and girl
22:28 72%

Mature Tgirl Ass 2 Mouth Threesome

7 months ago

PornHub

mature, small cock, mature anal, big ass, interracial, big tits, penis
26:50

Jeni Justice Trained And Turned Into A Sexy Sissy

7 months ago

ShemaleZ

stockings, big ass, sissy
27:00

Shelly Sexx bootie training

7 months ago

ShemaleMovie

dildo
20:21 77%

Forced By Step Mommy Sissy Enema And Anal Training

7 months ago

ShemaleZ

mom, sissy
40:03

Sissy training

7 months ago

ShemaleMovie

vintage, sissy
44:13

Marcela Dimov In Vitoria Mayer - Train Of Anal Sex 2

7 months ago

ShemaleZ

train, threesome, brazil
16:33

Shemale plumbs a girl on the train

7 months ago

ShemaleMovie

public, anal, ladyboy
22:05

SISSY BUM CREVICE Instructing three

7 months ago

TrannyGem

instruction
21:05

Training my anal pussy

7 months ago

xHamster

fisting, dildo, escort
15:31

Abased Sissy Maid - Domina Task

7 months ago

TrannyGem

femdom, crossdresser
24:43

Black cock sissy training bbc

8 months ago

PornHub

homemade, teen anal (18+)

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