Sissy Shemale Videos » 16

TrannyOne

SISSY IN HIGH HEELS HUGE STRAPON IN THE ASS Pegging Extreme Anal Stretching FEMDOM ASS FISTING

Categories: anal, anal fisting, anus, ass, bdsm, bondage, crossdressing, domination, double penetration, extreme

aShemaleTube

Crossdresser Fucks Cute Red Headed Girl

Categories: crossdressing, cute, queen, redhead, sissy

HClips

Sissy Slut Grindr Fucked Compilation

Categories: amateur, ass to mouth, blonde, compilation, crossdressing, cumshot, lingerie, sissy, slut, stockings

aShemaleTube

Sizzling POV Cum Session.

Categories: bbw, black, crossdressing, cum, cumshot, ebony, fat, ladyboy, lingerie, masturbation

aShemaleTube

Sissy nurse teachs you to cum in a condom

Categories: amateur, blonde, condom, crossdressing, cum, femboy, hd, latina, lingerie, nurse

xHamster

Gina CD Tranny Slut in PVC Wanking and Squirting

Categories: amateur, british, crossdressing, fetish, hd, lingerie, masturbation, mature, outdoor, pissing

xHamster

Patty crossdresser personal assistant Comment my new haircut

Categories: amateur, crossdressing, cum, european, fleshlight, french, hd, high heels, ladyboy, lingerie

JizzBunker

Cumming Like a Sissy Bitch - Sissygasm

Categories: anal, big ass, big cock, bitch, cum, dildo, fishnet, hardcore, masturbation, mature

xHamster

Extreme asshole training for sissy

Categories: amateur, anal, ass, dildo, extreme, fucking machine, german, homevideo, sissy, transsexual

KeekAss

This femboy came ready (innocence)

Categories: amateur, anal, assfucking, booty, crossdressing, doggystyle, femboy, femdom, handjob, hd

KeekAss

Ultra-Kinky Bride - the camera operator got HIGHLY aroused

Categories: amateur, bride, crossdressing, fetish, hd, high heels, kinky, ladyboy, lingerie, masturbation

TrannyOne

Crossdresser Sissy Gina - Black Widow

Categories: anal toying, ass, big black cock, big cock, black, booty, buttplug, crossdressing, dick, ebony

aShemaleTube

greek ass sissy crossdresser giouli

Categories: amateur, ass, brunette, crossdressing, greek, homevideo, lingerie, sissy, small tits, solo

ShemaleZ

Sissy Gets Grindr Bareback Fucked

Categories: amateur, anal, barebacking, blonde, blowjob, crossdressing, curly haired, lingerie, sissy, stockings

KeekAss

Excellent Sissy

Categories: anal, blonde, blowjob, cumshot, hd, homevideo, pornstar, sissy

KeekAss

Sissy Tramp jism with her 8in faux-cock

Categories: amateur, anal, big cock, blowjob, cute, dick, femboy, hd, mexican, sissy

aShemaleTube

Cute femboy Fiji sexy show💗

Categories: big ass, big cock, cute, edging, femboy, hd, latina, masturbation, orgasm, sissy

xHamster

Joselynne Cd In High Heels And Stockings With Sexy Mini Dress Show Big Ass

Categories: amateur, big ass, crossdressing, dress, feminization, fetish, hd, high heels, ladyboy, mature

KeekAss

Beauty Shemale Uses Dildo

Categories: amateur, anal, babe, beauty, big tits, blonde, caught, dildo, homevideo, jerking

KeekAss

Sissy Oksana railing a monster fake penis

Categories: amateur, anal, anal toying, cage, crossdressing, dick, dildo, lingerie, masturbation, mature

aShemaleTube

Vintage Crossdresser Ancelina and Mature Girl Lesbian s

Categories: crossdressing, lesbian, mature, queen, sissy, vintage

aShemaleTube

Sissy daily anal training

Categories: amateur, anal, cage, cuckold, dildo, femboy, feminization, homevideo, humiliation, lingerie

aShemaleTube

Hot White Femboys PMV PT1

Categories: anal, big cock, compilation, dildo, hd, masturbation, sissy, solo, white

TrannyOne

Mistress Her Sissy Gurl Cum

Categories: cum, gay, mistress, sissy

xHamster

My Miniskirt Too Short?

Categories: amateur, asian, crossdressing, hd, japanese, masturbation, mature, miniskirt, outdoor, sissy

xHamster

Chastity Sissy Riding a BBC

Categories: american, anal, big ass, big black cock, cage, doll, hd, ladyboy, riding, sissy

xHamster

Sissy jenny, Southampton UK slut

Categories: bitch, british, dildo, english, european, fishnet, hd, lingerie, sissy, slut

xHamster

TRANS SLUT UNIVERSITY: Jade Gets Ass Fucked To Get In PREVIEW

Categories: amateur, american, anal, assfucking, asslick, beauty, blowjob, cumshot, doggystyle, handjob

KeekAss

Encaged Sissy cuming Palms free-for-all with E-Stim

Categories: amateur, cage, crossdressing, cum, fetish, hd, pantyhose, sissy, stockings

KeekAss

mariaputa molten yellow view bottle

Categories: amateur, anal, anal toying, ass, big ass, bottle, crossdressing, dancing, doggystyle, femboy

aShemaleTube

I got blowjob from Amateur sissy crossdresser

Categories: amateur, blowjob, couple, crossdressing, cumshot, desi, homevideo, ladyboy, sissy

aShemaleTube

HANDS-FREE: The Most Beautiful Cumshot I Have Ever Recorded of Myself, I Am A Ladyboy, Sissy

Categories: beauty, college, compilation, cosplay, crossdressing, cum, cumshot, ladyboy, masturbation, pornstar

ShemaleMovie

Femboy Tiffany Ciskiss in cosplay goes to town with massive toys

Categories: american, anal, anal toying, ass, cosplay, crossdressing, dildo, extreme, femboy, fisting

aShemaleTube

MATURE SISSY PLAYING WITH HER OLD SAGGY COCK

Categories: amateur, crossdressing, dick, hd, lingerie, masturbation, mature, old, pantyhose, saggy tits

aShemaleTube

truck stop training slutwalk pink wig

Categories: amateur, big ass, caught, crossdressing, fetish, hd, high heels, outdoor, public, sissy

aShemaleTube

NikkiGee sits on a dlido and eats her cum!

Categories: barebacking, blonde, crossdressing, cum, cumshot, glasses, hd, homevideo, lingerie, masturbation

aShemaleTube

I love to do upskirts to flash my creamy white bubble butt sissy ass for rock hard BB12"NCs

Categories: ass, big ass, blonde, creampie, crossdressing, femboy, fetish, flashing, hd, interracial

ShemaleZ

asian bondage sissy in apron used by Master

Categories: amateur, asian, bdsm, bondage, master, sissy

aShemaleTube

Gigi and Dave Webcam Sex, 02.09.2025

Categories: blonde, british, couple, doggystyle, mature, outdoor, sissy, smoking, tease, webcam

xHamster

Big Beautiful Ass Tranny MILF Destroying Her Ass with a Fuck Machine and Cum

Categories: anal, ass, beauty, big ass, cum, cumshot, dildo, fucking machine, hd, masturbation

aShemaleTube

SIssy getting her pussy fucked in red panties wearing nylons doggystyle

Categories: amateur, anal, crossdressing, dildo, doggystyle, femboy, hd, homevideo, nylon, panties

ShemaleMovie

Assfuck, big ass

Categories: anal, anal toying, ass, assfucking, big ass, brutal, crossdressing, dildo, femboy, latina

xHamster

Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5

Categories: amateur, anal, barebacking, big cock, crossdressing, cum, cumshot, dutch, feminization, hd

xHamster

Destroying My Ass with a Huge Black 3 Level Dildo

Categories: amateur, anal, ass, big ass, black, dildo, fucking machine, hd, masturbation, mature

JizzBunker

Sissy Temptress

Categories: pornstar, sissy

Pornstars: Temptress

xHamster

Staying Wet

Categories: amateur, american, anal, beauty, blonde, crossdressing, femboy, fetish, hd, masturbation

aShemaleTube

I love teasing BB12"NCs rock hard for cum with upskirts and slow QOS panties striptease

Categories: big ass, blonde, crossdressing, cum, femboy, fetish, hd, interracial, ladyboy, lingerie

KeekAss

Fantastic Display Of Beauty And Erotic Prowess

Categories: amateur, american, beauty, crossdressing, cute, dildo, erotic, facial, fantasy, homevideo

TrannyOne

pale pink slut stroke her cock and ride huge dildo cum hard

Categories: amateur, anal, anus, ass, bdsm, big cock, cum, cumshot, dick, dildo

aShemaleTube

I'll fill your asshole with cum - dirty sissy slut fucked by BBC 1

Categories: amateur, anal, ass, barebacking, big black cock, cum, deep throat, dick, dirty, femboy

aShemaleTube

She uses her girlfriend's mouth then fingers her hard

Categories: amateur, ass, blowjob, deep throat, dick, fingering, girlfriend, hd, redhead, sissy

KeekAss

Sissy stroking off using a protection

Categories: bedroom, condom, crossdressing, dick, gay, handjob, hd, jerking, masturbation, sissy

KeekAss

Sissy gets her fuck-hole rode by a machine

Categories: amateur, anal, anal toying, dildo, femboy, fetish, hd, juicy, masturbation, sissy

xHamster

Latex dildo riding

Categories: amateur, anal, crossdressing, dildo, femboy, feminization, fetish, german, hardcore, hd

aShemaleTube

Gorgeous tgirl Angel dildo training 💋

Categories: anal, beauty, big ass, creampie, dildo, femboy, gorgeous, hd, homevideo, latina

HClips

Very Hot Sissy Maid Fucked By Boss

Categories: amateur, american, boss, hd, lingerie, maid, sissy, stockings

KeekAss

Beautiful Sissy And Girl Plays

Categories: amateur, beauty, big cock, blonde, dildo, hardcore, hd, homevideo, ladyboy, latina

KeekAss

Trans Woman ButtHOE Expose

Categories: amateur, anal, assfucking, crossdressing, hd, homevideo, italian, ladyboy, lingerie, milf

aShemaleTube

Naughty nurse in red leggings and 9" BBC SLUT platform stiletto heels teasing BB12"NCs

Categories: big ass, big black cock, blonde, blowjob, crossdressing, femboy, fetish, hd, high heels, interracial

TrannyOne

Ebony TS babe with a huge ladydick drills the sissy guy's ass nice and hard

Categories: anal, anus, ass, babe, bdsm, beauty, belly, big tits, black, blowjob

aShemaleTube

Another Tree fucked me

Categories: amateur, anal, crossdressing, hd, lingerie, outdoor, sissy, solo, stockings, toys

KeekAss

Lubricated up femboy penetrated and jizzes in innocence (ASMR squeals)

Categories: amateur, anal toying, big ass, boy, compilation, cumshot, cute, edging, femboy, hd

xHamster

Sexy horny slutty mature transvestite masturbates and cums on hotel fire escapes

Categories: amateur, big ass, big tits, crossdressing, cum, cumshot, french, hd, hotel, ladyboy

xHamster

Forged3dx Intense Anal Sex Delicious Big Ass Tasty Hot Intense Pleasure Open Anus Dripping Semen Intense Pleasure

Categories: amateur, american, anal, anus, asian, big ass, big cock, compilation, crossdressing, cum

xHamster

Sissy Pvc Maid

Categories: amateur, anal toying, bdsm, crossdressing, cum, hd, latex, maid, masturbation, orgasm

xHamster

Double Dildo Fun in Seethrough Panties and Vintage Bra

Categories: anal, bra, cum, dildo, funny, hd, homevideo, lingerie, masturbation, panties

KeekAss

Femboy Fellating Toes and Playing Donk Then Tonguing Own Jizm

Categories: amateur, beauty, big cock, blowjob, crossdressing, cum, cum swallowing, cumshot, feet, femboy

aShemaleTube

TS 548

Categories: amateur, femboy, homevideo, masturbation, sissy, solo, teen (18+), transsexual

xHamster

The Girl From Davao City Is Beautiful and Flirtatious Like That.

Categories: amateur, anal, asian, ass, beauty, big ass, crossdressing, cum, cute, dick

xHamster

Fisting ass sissy travesti

Categories: amateur, ass, boy, crossdressing, dildo, extreme, femboy, fisting, gaping hole, gay

ShemaleMovie

Melody undresses, plugs her juicy ass, and has an orgasm

Categories: amateur, anal, anal toying, ass, big ass, big cock, cum, cumshot, european, femboy

xHamster

Amazing Ass Tranny MILF Fucking Her Ass

Categories: amateur, amazing, anal, ass, assfucking, big ass, dildo, fucking machine, hd, masturbation

TrannyOne

Girls playing before going out

Categories: amateur, american, beauty, big cock, blonde, crossdressing, domination, femdom, fetish, ladyboy

xHamster

Dress Extravaganza: Trying on a Rainbow of Colors and Styles!

Categories: amateur, american, beauty, big ass, big cock, big tits, crossdressing, dress, feminization, hd

VideoSection

Shemale Daddyandlexa gets shared with a thick black cock in a wild compilation

Categories: amateur, american, anal, bdsm, big black cock, black, blowjob, bukkake, compilation, crossdressing

aShemaleTube

Fucking Goth Crossdresser Jade Madison - Compilation 5

Categories: amateur, american, anal, beauty, big ass, blowjob, compilation, crossdressing, femboy, goth

aShemaleTube

Smoking crossdresser

Categories: crossdressing, hd, homevideo, lingerie, mature, sissy, smoking, solo, stockings

xHamster

Anal hook BDSM

Categories: anal, bdsm, beauty, big ass, big cock, caught, crossdressing, cum, flashing, gaping hole

xHamster

Destroying My Huge Sissy Ass with Big Toys - Feet

Categories: anal, ass, big ass, dildo, feet, fishnet, hd, masturbation, mature, pussy

xHamster

Sisk on a Navy Blue Nightgown Riding a Fancy Dildo Ep1

Categories: amateur, anal, anal toying, asian, ass, clit, crossdressing, dildo, femboy, hd

xHamster

Sisk Plug Her Butt Wiht Wireless Vibrator

Categories: amateur, anal, anal toying, ass, bathroom, clit, crossdressing, femboy, hd, ladyboy

aShemaleTube

AcrylicKateQuinn Live Show Highlights 4

Categories: barebacking, big tits, blonde, cumshot, glasses, hd, homevideo, lingerie, sissy, toys

KeekAss

dream villa dressing bedroom gloss stockings and assets

Categories: amateur, anal, beauty, bedroom, big ass, brunette, crossdressing, cum, dildo, dress

TrannyOne

no.290 Suleika Latex fucks a sissy anal slut (first time)

Categories: amateur, anal, anus, ass, big cock, big tits, booty, couple, dick, dutch

aShemaleTube

A country cross dresser sucks a nice CL dick

Categories: amateur, country, crossdressing, dick, sissy, sucking

aShemaleTube

Shemale Suck Fuck Cum Compilation 1

Categories: amateur, anal, big ass, big cock, big tits, blowjob, compilation, cum, cum in mouth, cumshot

aShemaleTube

Sweet girl 5

Categories: big cock, creampie, cumshot, lingerie, masturbation, sissy, solo

KeekAss

Femboy Pops three times in Hip highs

Categories: amateur, anal, black, crossdressing, cum, cumshot, cute, dildo, emo, femboy

aShemaleTube

Outdoors peeing

Categories: amateur, crossdressing, dress, fetish, hd, lingerie, model, outdoor, pissing, sissy

aShemaleTube

Femboy plays with a vibrator

Categories: amateur, blonde, crossdressing, femboy, hd, model, sissy, small cock, small tits, solo

xHamster

Sissy Lissy

Categories: british, ladyboy, sissy, small cock

XXXDan

Nely big ass pink hole bitch play big clit sissy cum swallow

Categories: big ass, big clit, bitch, cum, cum swallowing, sissy

KeekAss

Naomi spunks on her face

Categories: amateur, anal, brunette, crossdressing, cum, cumshot, hd, lingerie, masturbation, sissy

TrannyOne

Asian sissy jerks long cock & cums

Categories: asian, cum, cumshot, dick, feet, fetish, jerking, masturbation, orgasm, oriental

aShemaleTube

A MUST SEE CROSSDRESSER fucked FULL MOVIE

Categories: crossdressing, queen, sissy

KeekAss

Latex T-WOMAN Attempt-on Drag!!! I jizz on Everything Instead$$$. My ARSE looks so pretty in my Stockings

Categories: amateur, ass, clothed sex, cosplay, crossdressing, cum, cumshot, femboy, fetish, handjob

XXXDan

Sissy Crossdresser being a slut for you

Categories: amateur, anal, big cock, crossdressing, dildo, latina, sissy, slut, small cock, solo

KeekAss

Femboy Ravages Herself with a Tiny Faux-cock

Categories: amateur, anal, anal toying, black, dick, dildo, femboy, feminization, hd, ravage

xHamster

Botat in My Ass Sissy Whore

Categories: ass, european, fishnet, hd, masturbation, sissy, skinny, slut, small cock, solo

xHamster

Fucking My Big Tranny Ass with Big Toys - Sissy Slut

Categories: anal, big ass, dildo, fucking machine, hd, masturbation, mature, milf, pussy, sissy

ShemaleMovie

Tights, wank

Categories: anal, ass, brunette, crossdressing, dildo, erotic, femboy, masturbation, sissy, stockings

aShemaleTube

Showing my ass in fishnet while I suck a dildo

Categories: anal, ass, big ass, crossdressing, dildo, fishnet, french, hd, sissy, solo

aShemaleTube

Chubby daddy creampied me after playing with my sissy clit

Categories: amateur, blonde, blowjob, chubby, clit, creampie, crossdressing, daddies, dick, hardcore

Pornstars: Cassandra

HClips

Crossdresser Joy Fucked By Alexandra - Alexandra Joy

Categories: 3some, amateur, anal, assfucking, blonde, brunette, crossdressing, deep throat, hd, homevideo

Pornstars: Alexandra Joy

aShemaleTube

Tr4p G0dd3sss95 - 70

Categories: big ass, big tits, blonde, homevideo, lingerie, masturbation, sissy, small cock, teen (18+)

xHamster

Her ass can fit all my big black cock so good

Categories: amateur, anal, ass, barebacking, big black cock, big cock, colombian, creampie, crossdressing, hardcore

xHamster

crossdresser walks on the street in transparent high heels

Categories: amateur, crossdressing, european, feet, fetish, hd, high heels, ladyboy, latex, outdoor

XXXDan

WINDOW EXHIBITIONIST SISSY CUMSHOT MASTURBATION SMOOTH SEXY

Categories: anal, creampie, cumshot, exhibitionist, masturbation, mature, outdoor, pov, sissy, solo

KeekAss

Trans female dances like a loser.~~~~~~

Categories: amateur, big ass, big cock, compilation, crossdressing, cute, femboy, hd, masturbation, mistress

aShemaleTube

Virtual sex Pov Simatra CD fuck BBC *5

Categories: amateur, anal, big black cock, big cock, crossdressing, femboy, fetish, hd, lingerie, pov

xHamster

sissy japanese cd multi dry and wet

Categories: amateur, anal, asian, balls, crossdressing, cumshot, femboy, hd, homevideo, japanese

KeekAss

Trans Christmas Elf paws herself with a hitachi

Categories: amateur, bdsm, big cock, bondage, cosplay, crossdressing, cum, cumshot, dick, femboy

TrannyOne

4 CUMS RUINED !!!

Categories: 18 year old, crossdressing, cum, cumshot, dick, edging, femdom, handjob, hd, japanese

TrannyOne

Various Close Ups Anal Destruction

Categories: amateur, anal, anal toying, anus, ass, close up, crossdressing, dildo, european, extreme

aShemaleTube

👑🦵🍑Collant Sexy, BasCulotte,Talons Verre. CAM4 [3sep25] VaneSsaBiTCHx ParisChienneTrvProd

Categories: amateur, big ass, big cock, bimbo, crossdressing, french, hd, pantyhose, sissy, slut

xHamster

Horny Sissy Old Foreign with My Pinoy Master Trans

Categories: abuse, amateur, anal, asian, bdsm, bitch, boy, crossdressing, cum, daddies

KeekAss

Trans Hints and Tips

Categories: big tits, crossdressing, fetish, hardcore, masturbation, sissy, smoking, solo, transsexual

AlphaPorno

Needy tranny wants this juicy dick fully down the butt hole

Categories: anal, ass, bed sex, bedroom, blowjob, cowgirl, cumshot, dick, fake tits, handjob

xHamster

Huge Ass Tranny MILF Fucking Her Ass Doggy

Categories: anal, ass, assfucking, big ass, dildo, doggystyle, fucking machine, hd, masturbation, mature

aShemaleTube

MY LOVE 013

Categories: asian, chinese, crossdressing, ladyboy, lingerie, masturbation, sissy, solo, stockings, uniform