SHEMALE • SISSY 9,748 videos

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20:26

Shemale Trap Sissy Femboy Crossdresser Strip Masturbate Handjob Cum In Black Dress Stockings Heels

2 years ago

ShemaleZ

heels, dress, crossdresser
19:06

Sissy Femboy In Chastity Taking Big Dildos In Her Ass And Trying And Sissygasm

2 years ago

HClips

chastity
20:33

Fat shemale taking food with semen from her ass and taking it to her mouth, masochistic shemale whore

2 years ago

xHamster

fat, outdoor, latina, food, whore
16:21

Colorful Sissy Gets Railed With Kezra Knight

2 years ago

ShemaleZ

POV, sissy, teen (18+)
22:07

Sissy Quinn Stone takes Penetrate Machine Rear End Fashion

2 years ago

KeekAss

MILF, BBW, machine
15:45

Sissy In Chastity Pounding Creampie Fuckmachine

2 years ago

ShemaleZ

chastity, sissy
36:39

Two domina feminize a sissy maid

2 years ago

ShemaleTaxi

femdom, maid, BDSM, sissy
15:14 59%

Sissy Pov – Jenny Kennedy – Daddy’s Good Girl

2 years ago

HClips

POV, tattoo, crossdresser, sissy
27:29 82%

Chloe Clay – Caged Sissy Maid Gets Fucked Hard

2 years ago

ShemaleZ

maid, sissy, BDSM, amateur, fetish
17:15

Trans sissy gurl striptease lap dance and railing faux-cock

2 years ago

KeekAss

latex, dance, fetish, strip, small cock, crossdresser
15:38

Sissy Sadee Gives Horny Wife Surprise Anal Sex Filling Her Ass With Cum

2 years ago

ShemaleZ

wife, BBW, surprise, sissy
16:25

Cute Teen Ladyboy Cock Caged And Dildo Insertions Sissy Clothes And Fun

2 years ago

TXXX

cute, small cock, dildo, insertion, clothed, sissy
21:47

Tranny takes 14 inch horse cock dildo on nail machine dark-hued light w/ pop-shot

2 years ago

ShemaleMovie

huge dildo, machine
16:59

Sissy Catgirl Gobbles her Own Jism

2 years ago

KeekAss

crossdresser, webcam
18:07

Sissy Camgirl Hottest Climax in Geyser & Converse Part 1

2 years ago

TrannyGem

orgasm, flashing, cumshot compilation, orgasm compilation, femboy
17:23

SISSY WALK IN THE FOREST IN PUBLIC

2 years ago

KeekAss

public, sissy
20:56

Sissy Maid Strappado Torture ReDone with thicker fuck stick,weights and more cords

2 years ago

KeekAss

latex, maid, crossdresser
15:02

Wondrous sissy outdoor Bikini

2 years ago

TrannyGem

public, outdoor, bikini
32:54

The Lust of Sissy Boy - Meeting the hot new neighbor

2 years ago

xHamster

cartoon, sissy
18:35

Busty Tranny Dominates A Sissy Crossdresser With Isabelly Ferraz

2 years ago

Upornia

big tits, domination, shemale fucks guy
19:12

Emily sissy schoolgirl

2 years ago

ShemaleTaxi

taxi, femboy, sissy
19:53

Sissy crossdress in legal wheeler car

2 years ago

TrannyGem

car
33:56

Massive Dildo And Knot For Sissy Tranny - Bad Dragon Stan And Bishop

2 years ago

ShemaleZ

dildo, sissy
21:42 45%

Mistress turns femboys into bbc hungry sissys

2 years ago

XXXDan

small cock, BBC, sissy, femboy, small tits, black
20:12

Sissy superslut rectal masturbing in the garage

2 years ago

TrannyGem

public, heels, socks, skirt, solo
17:44

Trancess Triss Introduces: Sissy rectal sesh with fuckmachine

2 years ago

TrannyGem

train, dress, machine, chastity
17:45

Sissy Academy - Part 6

2 years ago

Upornia

fetish, BDSM, sissy, shemale and girl
20:58

Shemale, trap, sissy femboy, crosssundresser strips, masturbates, strokes, spunks in black dress with stockings and heels

2 years ago

ShemaleMovie

french, smoking, heels, dress
35:13

Small femboy sissy trap spreads their crevasse and takes node. (Whore nearly got caught by a stranger)

2 years ago

KeekAss

caught, whore, stranger, femboy
16:50

Rosy femboy finishes off palms free-for-all from vibration of the pink pucker and showcases her slot ( sissy trap )

2 years ago

TrannyGem

train, prostate, massage, vibrator, hands free
15:27

Sissy Podcast Slideshow

2 years ago

ShemaleTaxi

BDSM
32:26

Sissy plaything party

2 years ago

ShemaleTaxi

party, taxi, sissy
15:25

Sissyjenny88 Amateur Crossdresser Huge Big Tits Sissy Complete Alone-Outdoor Walk at Day Huge G-Cup Tits see trough

2 years ago

xHamster

homemade, public, outdoor
18:41

Sissy gal fucked red pumps massive fake penis

2 years ago

ShemaleTaxi

huge dildo, dildo, pump, penis, crossdresser
15:58

I am going to peg you like the sissy tart you are

2 years ago

ShemaleTaxi

bisexual, pegging
34:42

Sissy Maid Chained To Bed In Chastity, Gagged And Leather Bondage Mitts Handcuffed On

2 years ago

ShemaleZ

gagging, bondage, maid, leather, chastity
24:44

Sissy Virginity Ass Fucking Ballsack Hormone Feminization Trainer Spiral

2 years ago

TrannyGem

train, insertion, slut, sissy, chastity
17:42

Sissy Mindy handsome kitty fucktoy Sow

2 years ago

ShemaleMovie

sissy
27:02

Sissy Expect – ass fucking smash sesh with smash machine and chubby

2 years ago

TrannyGem

train, chubby, machine
15:41 50%

Sissy Dreaming

2 years ago

JizzBunker

shemale, compilation, sissy
18:08

Teen Guy Sucks Sissy Live

2 years ago

Upornia

sissy
26:44

Killer TGirls Pauline and Charlotte in 4some hookup hump

2 years ago

TrannyGem

party, british, group, orgy, deepthroat, foursome
25:44 70%

Sexy Cd Sissy Rich Fuck With Her Young Neighbor

2 years ago

TXXX

sissy, amateur
23:11

Confessions of a Sissy Slut part 3!

2 years ago

xHamster

BBW, vintage, slut, solo
19:45

Kimber's BBC Sissy Trainer

2 years ago

TrannyOne

BBC, sissy
28:41

Sissy bullied into BBC porn

2 years ago

AShemaleTube

homemade, interracial, BBC, sissy, domination
17:58

Japanese Satanic Sissy bi-atch gang Rave

2 years ago

ShemaleTaxi

japanese, strip, skinny, sissy, small cock
28:49

Sissy jism burst compilation

2 years ago

TrannyGem

ladyboy, compilation, sissy
20:42

Pegging her sissy hubby

2 years ago

TrannyOne

pegging, sissy
46:12

SISSY IS ALWAYS greedy FOR wet COCK

2 years ago

ShemaleTaxi

small cock, wet, taxi, sissy, shemale fucks guy
25:01

Sissy 1

2 years ago

JizzBunker

shemale, sissy
15:55

Your Sissy Girlfriend Joi

2 years ago

ShemaleZ

solo, girlfriend, JOI, sissy
19:19

Japanese Sissy Masturbation 03

2 years ago

Upornia

japanese, sissy
28:14

Working from home as a Purity Sissy Assistant is so much joy

2 years ago

TrannyGem

femdom, strapon, fisting, glasses, heels, pegging
15:07

Brainless Sniffing Sissy fag doofy sucker Mindwash

2 years ago

ShemaleTaxi

sissy
23:35

Sissy Trainer 16 - Stop go JOI

2 years ago

TrannyOne

JOI, hardcore, sissy
21:35

SISSY IS ALWAYS hungry FOR wet COCK

2 years ago

ShemaleTaxi

wet, small cock
22:49

Sissy gangbang

2 years ago

TrannyOne

crossdresser, gangbang, black
17:46

Super-Fucking-Hot trans top Ariel Demure makes me her tiny sissy

2 years ago

KeekAss

sissy, hardcore
15:20

Your Sissy GIRLFRIEND - Bunny Dame Edging Jerk Off Instructions

2 years ago

TrannyGem

instruction, piercing, 18, nylon, JOI
18:52

Breezies Transgender employees being sissy in front of the mirror

2 years ago

TrannyGem

hooker, whore
19:03

Sissy Lucy being locked up in iron V-Card for Locktober

2 years ago

TrannyGem

femdom, bondage, BDSM, glasses, shaving
17:49 73%

Sissy Vein Get Fucked And Cum At The End

2 years ago

Upornia

asian, gangbang, sissy
15:23

SISSY BITCH humps THICK faux-cock and jacks trouser snake

2 years ago

TrannyGem

dildo, riding
27:31 86%

Erotiche Sissies

2 years ago

ShemaleZ

shemale, ass licking, sissy, brunette
19:36

Plumper ladyboy and skinny Shemale Suck and Have Fun

2 years ago

ShemaleTaxi

kissing, BBW, spanking, close up, skinny
23:31

Sosobitch help sissy+ cd

3 years ago

TrannyOne

sissy
17:09

Sissy Fucked From Behind, Her First Big Arab Cock

3 years ago

ShemaleZ

arab, sissy
15:22 54%

20 instructions for Sissies

3 years ago

ShemaleTaxi

public, instruction, outdoor, boots, taxi, sissy
18:20

CD fucksluts sissy hump have fun inbetween pals

3 years ago

TrannyGem

slut, sissy, cosplay
16:14

Lovely mischievous sissy crossdresser nails her rump with coca-cola bottle

3 years ago

KeekAss

bottle, crossdresser
22:39

Sissy with Her bf on web cam

3 years ago

ShemaleTaxi

sissy
25:11

Bitch Rico Sissy Slut In Red

3 years ago

ShemaleZ

slut, sissy
17:44

Crossdresser sissy deep-throats and tears up with mature

3 years ago

TrannyGem

crossdresser
15:21

Doofy Dominatrix Hook-Up Replace. A Sissy Fuckfest Guide

3 years ago

TrannyGem

femdom, swiss
16:00 64%

Baby Doll - Sissy Chastity, Fills Hole And Is Humiliated

3 years ago

HClips

doll, sissy, chastity, solo
16:17 44%

Sissy Transformation Story Ep 1

3 years ago

TrannyOne

hardcore, story
40:44

Cynthia Sissy Makes Husband Cum In Her Mouth And Sissy Pussy

3 years ago

HClips

fetish, husband, cum in mouth, sissy
24:47

Sissy Trainer/Sissy Dreams Rus

3 years ago

TrannyOne

sissy
26:20

Sissy joi five

3 years ago

ShemaleTaxi

JOI, sissy
20:06

Mature sissy jizzes stiff while handballing and straponing

3 years ago

ShemaleTaxi

mature, strapon
19:54

Sissy Crossdresser Receives Pounded By Landlord

3 years ago

ShemaleZ

crossdresser, sissy
15:38

Smoking Hy-pno sissy instructing 03

3 years ago

ShemaleTaxi

smoking, instruction
29:45

Queen Sissy man sausage biotch

3 years ago

KeekAss

blowjob, compilation, handjob compilation, cumshot compilation, sissy
17:11

Sissy brainwash

3 years ago

TrannyGem

cum in mouth, cumshot compilation
32:54

Hooker sissy at work

3 years ago

TrannyGem

hooker
15:16

Nubile Sissy couple of trannies with a tail gargle each other

3 years ago

ShemaleTaxi

thai, taxi
22:41

Sissy luvs bbc

3 years ago

ShemaleTaxi

BBC, sissy
24:55

Sissy wishes trio trainer, music edition (love to love you)

3 years ago

ShemaleTaxi

sissy
16:41

Sissy ladyboy crossdresser in pantyhose stroking and jizz

3 years ago

ShemaleTaxi

pantyhose, taxi, sissy
20:23

Ejaculation At 10 Min Tgirl Riding Sissy Penis

3 years ago

ShemaleZ

penis, webcam
15:09

Sissy cleaning in purity gets bored, attempts to jism instead

3 years ago

ShemaleTaxi

british, sissy
17:12

The Sexy Slutty Sissy Stepsisters Have Another Quickie

3 years ago

Upornia

sissy
15:21

Sissy Play With Mr Hankeys Xxx Calibur Dildo

3 years ago

ShemaleZ

toys, dildo
30:27

Prádélko, sissy joi

3 years ago

VideoSection

BDSM, domination, JOI, sissy, creampie
56:35

Tv is for Sissies (Full Video)

3 years ago

TrannyOne

BDSM, sissy
16:21

Sissy 666AmberRayne666 BDMS Streching reaming Ear Pircings

3 years ago

ShemaleTaxi

sissy
28:18

Sissy Maids Self Bondage Armbinder and Chastity Belt

3 years ago

xHamster

latex, bondage, maid, chastity
18:41

Trans Sissy Hands Free Cum Pillow Humping

3 years ago

ShemaleZ

hands free, teen (18+)
29:14

Sissy is all you want and need

3 years ago

xHamster

JOI, sissy
15:28

Sissy Bimbo Snowbunny Pmv

3 years ago

ShemaleZ

sissy
1:33:58

Skinny german Sissy in stockings shows off sexy small ass

3 years ago

AShemaleTube

german, skinny, sissy
20:53

Bbc Owned Sissy

3 years ago

ShemaleZ

BBW, BBC, sissy, big cock
15:20

Guy gag sissy

3 years ago

TrannyOne

gagging, cum in mouth, sissy
26:30

Tranny fuck sissy man

3 years ago

AShemaleTube

latina
15:41

CD MEGA-BITCH PRUNING her COCK-SQUEEZING SISSY BEAVER FOR YOU then POUNDING IT ROCK HARD w GINORMOUS nine INCH FAUX-COCK

3 years ago

TrannyGem

train, shaving, bathroom
16:54

Clean-Shaven TRANSSEXUAL-Female rails a humungous black faux-cock

3 years ago

TrannyGem

riding, gape
16:23

Killer sissy Charlotte learns to gargle a massive fuck-stick

3 years ago

TrannyGem

homemade, latex, british, deepthroat, skinny
16:08

Tattooed Daddy Barebacks his Sissy Boy

3 years ago

TrannyOne

bondage, sissy
26:25

Sissy desires - three (eng)

3 years ago

ShemaleTaxi

shemale fucks guy
25:04

Carla Novaes ladyboy sissification

3 years ago

ShemaleTaxi

domination, sissy
18:24

Lovely Sissy Maid Shoots A Load Two Times. Part 1

3 years ago

TrannyGem

feet, maid, cum in ass
17:12

Sissy instructing instructional

3 years ago

TrannyGem

train, instruction, compilation
20:10

SISSY SHOOTS A LOAD IN V-CARD AFTER five DAYS OF V-CARD JIZM IN SHAFT CELL Virginity Jizm Compilation

3 years ago

TrannyGem

orgasm compilation, chastity
15:08

Suleika Spandex ravages a sissy buttfuck bi-atch (first-ever time)

3 years ago

TrannyGem

spandex, dutch, first time
15:12

TRANSSEXUAL Silly Tabletop Gamer Inhales and Boinks Dungeon Space Sir

3 years ago

TrannyGem

train, bondage, BDSM, game, sissy
18:45

Dominant Shemale MILF fucks Sissy Boy - 3D Animated Anal Sex

3 years ago

TrannyOne

MILF, 3D, domination
24:05

SISSY TRAINER PMV SISSY ANAL INVASION PMV SISSYMAKER EXTRAORDINARY BUTT WIDE OPEN HIGH HIGH-HEELED SLIPPERS BANG

3 years ago

TrannyGem

femdom, bondage, double anal, heels, gape, double penetration
27:39

Deep-throating commands for sissys are available in this flick

3 years ago

KeekAss

ebony, big ass, interracial, big tits, 18, deepthroat, bareback
20:55

Sissy CD in High-Heeled Slippers Fellates and Rails my BWC Vigorously - Cowgirl

3 years ago

KeekAss

handjob, heels, sissy

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