Crossdressing Shemale Videos » 36

JizzBunker

Athletic athlete with abs fucks the ass of a 21-year-old transvestite

Categories: anal, ass, asslick, blowjob, couple, crossdressing, gay, hairy, handjob, old

xHamster

Natacha Mancinelli - I love my fuckmachine

Categories: amateur, anal, crossdressing, french, fucking machine, hd, sissy, slut, solo, webcam

aShemaleTube

First time sissy on a fuck machine

Categories: amateur, anal, crossdressing, first time, fucking machine, hd, homevideo, masturbation, sissy, solo

xHamster

Horny Latex Slut Locked In The Inverted Chastity Cage

Categories: beauty, cage, crossdressing, cute, hd, ladyboy, latex, sissy, slut, stockings

KeekAss

Transgender Princess CD Selenas assfuck pummeling Clamps from plowing Sesh on Wednesday Tweak two

Categories: amateur, anal, anal toying, assfucking, big ass, clamp, crossdressing, dildo, fetish, fucking machine

aShemaleTube

Tranny DreemZ Crossdresser Sissies in Bondage and Train

Categories: bondage, crossdressing, train, tranny

aShemaleTube

Blonde in pink lingerie and black latex boots

Categories: amateur, black, blonde, boots, crossdressing, femboy, fetish, hd, ladyboy, latex

KeekAss

CD Breezy WIth Hefty Booty Screwed By Machine Part two

Categories: amateur, anal, anal toying, ass, big ass, booty, chubby, crossdressing, dick, dildo

KeekAss

Jizzing in the couch

Categories: amateur, anal, couch, crossdressing, cum, hd, masturbation, mature, milf, pantyhose

xHamster

Futuretist Intense Hard Sex Hot Big Ass Whore with Tight Fat Ass Riding on a Huge Cock Intense Hard Sex Buttocks Thirsty

Categories: american, asian, ass, bbw, beauty, big ass, big cock, black, compilation, crossdressing

TrannyOne

Sexy Italian Pennymilano cums at 8:23

Categories: amateur, crossdressing, cum, cumshot, italian, lingerie, masturbation, sissy, small cock, small tits

xHamster

Sissy slut Raven cums while playing with her dildo - Maddy Diamond

Categories: anal, cosplay, crossdressing, cum, dildo, hd, ladyboy, latina, masturbation, nerdy

KeekAss

Underwear she-creature rails a nine" fake penis and jizzes - black miniskirt, brassiere and tights

Categories: anal, big cock, black, bra, crossdressing, cum, cumshot, dick, dildo, lingerie

aShemaleTube

sucking dildo with clamps on nipples to get plessure...

Categories: 3some, anal, clamp, crossdressing, cum in mouth, cumshot, dildo, domination, gangbang, group sex

aShemaleTube

Bouncing on a hard daddy cock

Categories: amateur, anal, crossdressing, daddies, dick, hd, homevideo, masturbation, mature, sissy

xHamster

Close up Cum

Categories: amateur, asian, barebacking, bbw, big ass, big cock, black, close up, creampie, crossdressing

xHamster

Crossdresser Emika shows off sexy legs in high heels and strokes cock

Categories: amateur, big cock, canadian, crossdressing, dick, feminization, hd, high heels, legs, lingerie

xHamster

BIG ASS Ladyboy Hot Bend Down Pose White Sexy Bubble Butt

Categories: 3some, amateur, american, ass, beauty, big ass, big cock, big tits, crossdressing, femboy

xHamster

Jessic Ajain 2nd video

Categories: amateur, beauty, crossdressing, feminization, hd, homevideo, sissy, solo, transsexual

aShemaleTube

I found him on the street with this gigantic 25 cm big cock hitting me hard, could I take it

Categories: amateur, big cock, big tits, compilation, crossdressing, cum in mouth, domination, fetish, hd, homevideo

TrannyOne

Thick cock gothic shemale cums

Categories: crossdressing, cum, dick, fat, goth, jerking, obese, queen, sissy, thick

aShemaleTube

Crossdresser standing piss

Categories: amateur, crossdressing, hd, homevideo, mature, pissing, sissy, small cock, standing, stockings

xHamster

Enjoying a cigarette

Categories: amateur, cigarette, corset, crossdressing, dutch, european, fetish, hd, mature, milf

XXXDan

River dance in the chastity cage

Categories: amateur, blonde, cage, cosplay, crossdressing, fetish, lingerie, nude, outdoor, public

aShemaleTube

webcams crossdress SVID_20240225_232008_1

Categories: amateur, asian, big ass, chinese, crossdressing, fetish, hd, homevideo, lingerie, model

xHamster

It's time for my birthday spanking!

Categories: amateur, american, bbw, bdsm, beauty, big ass, birthday, crossdressing, fetish, hd

aShemaleTube

anal pleasure games

Categories: anal, crossdressing, game, hd, mature

KeekAss

Superb Culo and beefy lesgs TransMilf punding her culo with giant faux-cocks and spunk - web cam showcase

Categories: amateur, anal, anal toying, ass, assfucking, big ass, crossdressing, cumshot, dick, dildo

aShemaleTube

Smoking Fetish Goddess Marilyn

Categories: amateur, blonde, crossdressing, fetish, goddess, hd, mature, mistress, pov, smoking

KeekAss

Awesome shemale monster beefstick meaty cum shot - TScamdolls.com

Categories: amateur, big cock, big tits, brunette, crossdressing, cumshot, dick, gay, handjob, hd

VideoSection

Transgender solo play with a greased-up crossdresser in cute lingerie

Categories: anal, bbw, close up, crossdressing, cumshot, cute, lingerie, masturbation, oiled, orgasm

VideoSection

Gorgeous solo trans performer Lolacd shows off her sexy style

Categories: amateur, asian, ass, babe, beauty, big ass, crossdressing, femboy, gorgeous, ladyboy

xHamster

Trixy and the worker short version

Categories: amateur, anal, barebacking, bdsm, beauty, big cock, blowjob, crossdressing, cum, cumshot

xHamster

Nuttytouch Big Booty Bitch Fucking Hard with Huge Monster Cock Intense Anal Sex Sweet Hot Ass Gaping

Categories: amateur, anal, asian, ass, barebacking, bbw, big ass, big cock, bitch, black

xHamster

Hot Horny Wank And Cum

Categories: amateur, crossdressing, cum, cumshot, dick, feminization, fetish, handjob, hd, lingerie

xHamster

Sissy Femboy Rides Big Black Cock Sex Doll

Categories: american, anal toying, big ass, big black cock, black, crossdressing, cum, dick, dildo, doll

KeekAss

Two traps sluts are having fun on cam

Categories: amateur, beauty, bimbo, blowjob, brunette, couple, crossdressing, funny, homevideo, masturbation

KeekAss

Trans Dude Uses Vibro And Fuck Stick to Demolish Ejaculation Numerous Times

Categories: amateur, big clit, crossdressing, dildo, edging, hd, homevideo, ladyboy, masturbation, moaning

KeekAss

sissy lady pokes with fuck stick like never before

Categories: amateur, anal, anal toying, big ass, crossdressing, german, hd, ladyboy, lingerie, mature

KeekAss

Arousing urinate and cum shot

Categories: amateur, bed sex, crossdressing, cumshot, hd, homevideo, latina, masturbation, mature, old

aShemaleTube

CdTina gagging on guest 1

Categories: amateur, big cock, blonde, blowjob, crossdressing, fetish, gagging, hd, long nails, mature

xHamster

Indian Crossdresser Shemale Super Sexy Rina Deep Fuck Dildo -

Categories: amateur, asian, barebacking, bbw, big ass, big cock, black, crossdressing, dildo, hd

VideoSection

Naughty crossdresser in lingerie performs on cam in a hot session

Categories: amateur, babe, beauty, big cock, compilation, crossdressing, cum, cumshot, fishnet, french

xHamster

Crossdresser in Lingerie Fucks Emo Girl

Categories: amateur, american, anal, crossdressing, emo, hd, lingerie, stockings

xHamster

I get fucked hard and deep with my dildos every day and I love it!

Categories: anal, anal toying, ass, crossdressing, dildo, hardcore, hd, huge dildo, lingerie, riding

xHamster

Trans Bailey Wilde Puts Crossdresser in Chastity

Categories: amateur, american, anal, bondage, boy, crossdressing, cute, femboy, gay, handjob

XXXDan

EDGEWORTH JOHNSTONE Preview 19

Categories: amateur, big cock, british, crossdressing, cute, european, fetish, gay, masturbation, mature

aShemaleTube

Davine plays with her ass and cums hard

Categories: ass, barebacking, brunette, cage, crossdressing, cum, cumshot, glasses, homevideo, lingerie

aShemaleTube

Secretary Sonia

Categories: amateur, blonde, crossdressing, hd, homevideo, masturbation, mature, secretary, sissy, solo

TrannyOne

Chubby Wife in Pantyhose and Skirt gives CD Hubby a Handjob

Categories: ball busting, chubby, crossdressing, dress, femdom, fetish, hairy, handjob, husband, lingerie

aShemaleTube

Lingerie, clamps and nipple suckers... Sounds fun, isn't it?

Categories: amateur, clamp, crossdressing, cumshot, fetish, funny, hd, homevideo, lingerie, masturbation

aShemaleTube

anyone want to have webcam fun with me? dm or comment

Categories: amateur, asian, crossdressing, funny, hd, homevideo, interracial, latina, sissy, solo

xHamster

Big Booty crossdresser gets fucked by Bigdaddy8inchz

Categories: 3some, amateur, american, anal, barebacking, big black cock, booty, creampie, crossdressing, cuckold

aShemaleTube

Outdoor hooker in pvc clothes

Categories: blowjob, clothed sex, crossdressing, hd, mature, outdoor, slut

xHamster

Trans Jessica Moon Sucks Bailey Wilde's Cock

Categories: amateur, american, anal, big cock, blowjob, crossdressing, cum, dick, femboy, feminization

xHamster

That's why we don't have carpets

Categories: anal, bdsm, bondage, crossdressing, cumshot, czech, domination, fetish, hd, high heels

aShemaleTube

Christina Hearts Dark Angel Dark Princess 005 Dark Angel Dark Princess Introduction

Categories: amateur, big cock, crossdressing, domination, fetish, hd, ladyboy, lingerie, mature, pornstar

Pornstars: Angel Dark, Christina Dark

KeekAss

Smoking Fetish Domina Marilyn Has A Message four U

Categories: amateur, beauty, big cock, brunette, crossdressing, dominatrix, fetish, hd, huge cock, lesbian

aShemaleTube

KIANA 2 JUNE 2025

Categories: amateur, crossdressing, hd, homevideo, mature, outdoor, pantyhose, small cock, small tits

aShemaleTube

I'm Ginger. Want to fuck?

Categories: amateur, compilation, crossdressing, cumshot, hd, lingerie, masturbation, mature, toys

xHamster

Sexy Trans Secretary

Categories: amateur, beauty, crossdressing, hd, masturbation, mature, secretary, solo, stockings, tranny

xHamster

Nuttytouch POV Swallow a Huge Monster Cock Intense Hard Sweet Tasty Ass Destroyed

Categories: amateur, american, asian, ass, barebacking, bbw, big ass, big cock, black, creampie

XXXDan

Anal masturbation 05.2023 - Huge dildo inserted a little deep

Categories: anal, bdsm, big cock, crossdressing, dildo, fisting, gaping hole, hardcore, huge dildo, insertion

aShemaleTube

Tranny Holly smoking in the pink

Categories: crossdressing, hd, homevideo, mature, model, smoking, solo, stockings, tranny, transsexual

xHamster

Sissy and Monster Dildo

Categories: amateur, anal, anal toying, ass, crossdressing, dildo, femboy, feminization, hd, ladyboy

KeekAss

in the camper by the roadside seamless tights

Categories: amateur, anal, beach, beauty, big ass, crossdressing, cum, dildo, feet, femboy

aShemaleTube

Asshole Workout part2

Categories: amateur, ass, crossdressing, homevideo, lingerie, masturbation, solo, stockings, toys, workout

aShemaleTube

BBC vs Sissy cock comparison & blowjob - Daddy humiliated me! @ Sasha_de_Sade on all website

Categories: abuse, amateur, big black cock, big cock, blowjob, crossdressing, daddies, dick, domination, fetish

aShemaleTube

Una Sissy en Celo

Categories: amateur, crossdressing, hd, kissing, public, romantic, sissy, spanish

HClips

Sissy Crossdresser - 20 Year Old Trans Girl Sucking A Married Straight Guys Cock

Categories: amateur, anal, assfucking, brunette, crossdressing, dick, handjob, hd, homevideo, latina

KeekAss

Sissy Stretches Her Gams For Firm Deep Butt Penetrating

Categories: amateur, anal, anal toying, ass, big ass, chubby, crossdressing, dick, dildo, fetish

XXXDan

Tranny maid gets fucked hard in the ass because she loves cocks

Categories: amateur, anal, ass, beauty, big ass, big cock, crossdressing, dick, fetish, hardcore

xHamster

Forged3dx Intense Hard Sex Delicious Hot Big Ass Dripping Semen Intense Pleasure Hard Sex Sweet Hot Ass Fucked Buttocks Thirsty

Categories: amateur, american, asian, assfucking, barebacking, big ass, big cock, crossdressing, cum, hardcore

xHamster

Natasha opens her

Categories: amateur, anal, anal toying, big black cock, crossdressing, domination, european, fantasy, feminization, french

xHamster

New tattoo same slut

Categories: amateur, anal, anal toying, boy, clit, crossdressing, cum, dick, dildo, hd

aShemaleTube

big tit girdle bondage 3

Categories: big tits, bondage, crossdressing, girdle, transvestite

VideoSection

Cute femboy Lanarini Ray enjoys some solo anal play with big toys

Categories: anal, anal toying, beauty, crossdressing, cute, dildo, femboy, ladyboy, masturbation, sissy

xHamster

Sexyfilomena Puts Her Toy on Her Massage Table and Sits on It

Categories: amateur, anal, beauty, canadian, crossdressing, cum, dildo, hd, homevideo, lingerie

KeekAss

Pound my muddy culo in this stockings undergarments

Categories: amateur, anal, big ass, creampie, crossdressing, cute, femboy, hd, latina, mud

JizzBunker

Secretdreamsfuta Hard Sex Delicious Big Hot Ass Cum Thirsty Sweet Tasty Ass Fucking Intense Pleasure Hard Sex

Categories: 3d, amateur, asian, ass, assfucking, big ass, big cock, cartoon, crossdressing, cum

TrannyOne

Butt Girl Tiffany Ciskiss As Raven Super Cut Fucking Ass On Huge Dildos

Categories: amateur, american, anal, anal toying, ass, cosplay, crossdressing, dildo, european, extreme

KeekAss

Shemale Masturbating Her Dick On Cam

Categories: amateur, beauty, big tits, blonde, brunette, crossdressing, dick, dildo, ebony, hd

xHamster

I Cumming in My Mouth

Categories: amateur, anal, crossdressing, cum, cumshot, european, feminization, hd, lingerie, sissy

aShemaleTube

Chubby&Milky. Serge Lu-sin.2023a

Categories: amateur, chubby, crossdressing, hd, ladyboy, mature, milk, solo

aShemaleTube

MELISSA MENDEZ UK T-GIRL COMP

Categories: compilation, crossdressing, hd, masturbation, pornstar, stockings, tgirl, toys, uk

Pornstars: Melissa Mendez

aShemaleTube

sissy tied with played and

Categories: crossdressing, sissy, tied up

TrannyOne

Mature crossdresser gets fucked hard and cummed in her mouth

Categories: anal, anus, ass, crossdressing, cum, cum in mouth, cumshot, drilling, facial, hardcore

aShemaleTube

Hot blue eyes Cumin

Categories: amateur, blue eyed, crossdressing, homevideo, solo, webcam

XXXDan

Fucking Hot BBW Trans Woman - Compilation 1

Categories: amateur, bbw, beauty, big ass, big cock, compilation, crossdressing, hardcore, transsexual

xHamster

Funy Editions 9

Categories: amateur, argentinian, asian, barebacking, bbw, big ass, big cock, black, creampie, crossdressing

xHamster

Rigid3d D3d Intense Anal Sex Compilation of Sluts Sweet Nymphs Tight Gaping Asses Swallowing Cum

Categories: amateur, anal, asian, ass, barebacking, bbw, big ass, big cock, black, compilation

aShemaleTube

CD mistress outdoor with nude guy in the woods

Categories: amateur, crossdressing, domination, exhibitionist, hd, latex, mature, mistress, nude, outdoor

xHamster

I'll stain my fitness clothes with my disgusting juices.

Categories: anal, asian, clothed sex, cosplay, crossdressing, fitness, hd, japanese, ladyboy, masturbation

KeekAss

Outdoor pervy sextimes

Categories: anal, bdsm, crossdressing, fingering, hd, latex, mature, outdoor, stockings, toys

aShemaleTube

taiwanese crossdresser fuck by big guy

Categories: amateur, asian, crossdressing, hd, homevideo, lingerie, model, stockings, taiwanese, transsexual

aShemaleTube

BBC Trainer Black Obsession

Categories: big black cock, black, crossdressing, pornstar, transvestite

Pornstars: Obsession

ShemaleMovie

Sissy always ready for some steamy man meat

Categories: anal, blowjob, creampie, crossdressing, gangbang, ladyboy, lingerie, outdoor, sissy, small tits

aShemaleTube

Macho dominicano me coje y me da leche en mi boca

Categories: amateur, anal, barebacking, blowjob, crossdressing, cum in mouth, cumshot, dominican, hd, homevideo

xHamster

MERRY CHRISTMAS AND A HAPPY NEW YEAR 2025 TO ALL MY FANS

Categories: amateur, asian, beauty, crossdressing, desi, hd, indian, masturbation, mature, pornstar

xHamster

Princess Bunnie: Naughty Maid Sneaks off to Masturbate

Categories: amateur, american, beauty, crossdressing, cum, hd, high heels, lingerie, maid, masturbation

aShemaleTube

You dirty, little, porn & cock addicted pervert...

Categories: crossdressing, cumshot, dick, dirty, domination, fetish, hd, latex, masturbation, model

Pornstars: Viper

XXXDan

Sissy jerks off in red corset and stockings

Categories: amateur, anal, big clit, corset, crossdressing, european, fetish, lingerie, masturbation, mature

xHamster

Another Slut Walk AntoniaCD77

Categories: buttplug, caught, crossdressing, doggystyle, hd, outdoor, public, sissy, slut

aShemaleTube

2 crossdressers facefuck and humiliate guy

Categories: abuse, blowjob, crossdressing, face fucking, humiliation, mature

KeekAss

stranger in d wrong house

Categories: amateur, anal, blonde, blowjob, crossdressing, ebony, lingerie, small tits, stranger, transsexual

aShemaleTube

Colleen TS Self Paddling - at least 100 strokes

Categories: amateur, ass, crossdressing, homevideo, pain, punishment, spanking, transsexual, webcam

aShemaleTube

Sexy show by Japanese cosplayer (part 2)

Categories: anal, cosplay, crossdressing, dildo, hd, japanese

xHamster

I'm getting fucked by a big dick

Categories: amateur, anal, beauty, big cock, blowjob, crossdressing, femboy, feminization, hardcore, hd

xHamster

Horny CD is outdoors such a sissy wearing heels and Mini skirt in public. no shame at all

Categories: big ass, brazilian, canadian, crossdressing, cum, feminization, hd, high heels, lingerie, masturbation

xHamster

No-pan Hotel Maid Pai-chan's Special Room Service

Categories: amateur, asian, crossdressing, dick, hd, high heels, hotel, japanese, lingerie, maid

aShemaleTube

Cute Brunette Tgirl Stroking Her Big Shaft

Categories: amateur, beauty, brunette, crossdressing, cute, homevideo, slave, solo, stroking, teen (18+)

KeekAss

Quickie toying with myself. Gobbled it all

Categories: amateur, big cock, brunette, crossdressing, cum in mouth, cumshot, handjob, hd, masturbation, mature

KeekAss

Sissy in observe thru sundress attempting on some Undies

Categories: amateur, babe, big ass, big cock, crossdressing, dress, fetish, hd, homevideo, legs

ShemaleZ

Frida - Crossdressing Cutie Gets Dicked Down

Categories: brunette, crossdressing, cute, dick, ebony, hd, interracial, pornstar, stockings

Pornstars: Frida

KeekAss

enjoy this veggie carrot poke in my butt toyplay cd tv

Categories: amateur, anal, ass, big ass, crossdressing, hd, homevideo, lingerie, mature, stockings

aShemaleTube

May Masterbation

Categories: amateur, crossdressing, hd, lingerie, masturbation, small cock

xHamster

Vlog #5 Trip to Medellin - Veronica Sanders

Categories: anal, big cock, blowjob, colombian, couple, crossdressing, dick, hd, latina, pov

xHamster

Didia Watching

Categories: beauty, belgian, big cock, crossdressing, cum, cumshot, european, hd, high heels, lingerie

xHamster

Femboy at night at home

Categories: amateur, asian, barebacking, big black cock, blowjob, crossdressing, cum, femboy, feminization, hd

xHamster

Masturbation in sexy black nylon, and dress

Categories: amateur, big cock, black, crossdressing, dress, hd, high heels, homevideo, lingerie, masturbation