Sissy Shemale Videos » 41

aShemaleTube

Trans Evolve MEGA PACK Compilation

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aShemaleTube

WolfPrincesss anal fuck machine show 💗

Categories: anal, big ass, blonde, femboy, hd, masturbation, milk, prostate, sissy, small tits

xHamster

Huge Dildos in My Sissy Slitty Ass

Categories: amateur, anal, ass, big ass, dildo, hd, huge dildo, lingerie, masturbation, mature

JizzBunker

Sissy Lisa in sports underwear loves BBC

Categories: amateur, big black cock, big cock, black, blowjob, crossdressing, deep throat, gagging, hardcore, lingerie

xHamster

Blonde Crossdresser get fucked by dildo

Categories: amateur, anal, blonde, crossdressing, dildo, femboy, feminization, german, hd, japanese

xHamster

I love Fucking Machines Clip 743

Categories: anal, anal toying, big ass, crossdressing, dildo, fucking machine, german, hd, homevideo, sissy

KeekAss

Turning Myself Into a Dirty Spandex Biotch

Categories: amateur, crossdressing, dirty, fetish, hd, homevideo, latex, sissy, small tits, spandex

TrannyOne

Sissy slut sucks and lets master fuck her

Categories: anal, cage, crossdressing, master, queen, sissy, slut, sucking

KeekAss

riskiy public walk in footwear and v-card

Categories: amateur, blonde, boots, crossdressing, hd, latex, leather, outdoor, public, sissy

KeekAss

Putita sissy se mete fuck sticks en el bum

Categories: amateur, anal, anal toying, big ass, cute, dildo, femboy, fetish, hairy, hd

xHamster

flip flops and skinny jeans - public crossdressing

Categories: amateur, crossdressing, european, feet, fetish, hd, high heels, jeans, lingerie, outdoor

xHamster

first video ever

Categories: amateur, bbw, german, hd, homevideo, sissy, small cock, solo, webcam

xHamster

Cdmichelle in the Shower

Categories: american, bathroom, crossdressing, hd, homevideo, lingerie, shower, sissy, solo, stockings

xHamster

Small Dick Sissy in Sissy Panties. Leaking Precum and Cum Ending. Alice Smallz

Categories: amateur, beauty, british, compilation, crossdressing, cum, cumshot, feminization, hd, ladyboy

JizzBunker

Man uses his sissy

Categories: amateur, anal, big ass, blowjob, cum swallowing, french, gay, sissy

aShemaleTube

White Lingerie Rina Teasing & Release

Categories: brunette, cage, crossdressing, cumshot, femboy, hd, homevideo, lingerie, sissy, stockings

aShemaleTube

Indian Crossdresser goes to Adult Video Store Part 1

Categories: crossdressing, gloryhole, hd, indian, sissy, store, theater

aShemaleTube

TSLucylux gets messy

Categories: amateur, anal, bathroom, femboy, hd, homevideo, messy, redhead, sissy, small cock

KeekAss

Sissy Vicky TRANSSEXUAL rambling the parking at night

Categories: amateur, bbw, big ass, brunette, crossdressing, latina, lingerie, mature, outdoor, public

HDSex

Transgender sissy Christian Xxx explores her side in high heels and takes some oral pleasure

Categories: amateur, big cock, blowjob, cum, cum in mouth, high heels, jizz, ladyboy, maid, oral

ShemaleMovie

Greek sissy slut compilation of solo anal pleasure and cum shots

Categories: anal, anal toying, compilation, cumshot, dildo, greek, lingerie, masturbation, pantyhose, sissy

xHamster

Femboy first time anal dildo

Categories: amateur, anal, anal toying, crossdressing, dildo, femboy, first time, hd, pretty, sissy

KeekAss

Domme sfonda il ass e la sissy ha orgasmi multipli, gode come una vera vacca troia

Categories: amateur, anal, ass, creampie, crossdressing, cumshot, domination, femboy, femdom, fetish

xHamster

Chubby Sissy Oiling her body

Categories: ass, bbw, big ass, black, chubby, crossdressing, fat, femboy, feminization, hd

xHamster

Playing with My Hole in the Bed with a Huge Cucumber on My Bottom Moaning Like Crazy It Won't Stop Until I Cum

Categories: anal, bed sex, big ass, crazy, cucumber, cum, greek, lingerie, masturbation, mature

XXXDan

Sissy and the ruffled rooster dress

Categories: big cock, creampie, dress, german, lingerie, masturbation, mature, sissy, solo

KeekAss

Very Hot Busty Tranny Jerks Her Cock

Categories: amateur, beauty, big tits, brunette, crossdressing, dick, femboy, homevideo, jail, japanese

aShemaleTube

Chubby Tranny and Skinny Shemale Suck and Have Fun

Categories: blowjob, chubby, cum in mouth, femboy, funny, glasses, homevideo, lingerie, redhead, sissy

KeekAss

Mayatsarina presents big butt and clit

Categories: amateur, big ass, bimbo, clit, crossdressing, hd, homevideo, sissy, small cock, stockings

aShemaleTube

Sissy Joyce humiliated and pegged by a goddess

Categories: abuse, anal, domination, femboy, goddess, hd, humiliation, ladyboy, model, sissy

KeekAss

Sumptuous Tiny Ponnyboy sissy ambling in store and outside

Categories: amateur, crossdressing, hd, husband, ladyboy, lingerie, outdoor, pov, public, shop

HClips

I Was Went Into The Wrong Bathroom But I Didnt Care, I Wanted A Dick - Sissy Crossdresser

Categories: amateur, anal, assfucking, bathroom, classic, crossdressing, deep throat, dick, hd, homevideo

ShemaleMovie

Hottest trans babe Jenniferstarts with a big ass takes on a fucking machine

Categories: anal, ass, babe, big ass, dildo, fucking machine, masturbation, sissy, small cock, toys

KeekAss

Thicc Trans Sweetheart Gets Drilled and Creampied By a Pulverizing Machine

Categories: anal, big ass, cage, creampie, doggystyle, drilling, gaping hole, hd, sissy, solo

xHamster

Complete Sissy Training Full Movie

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

xHamster

Trans Ria Bentley Worships Her Super Hung Grindr Match

Categories: american, anal, barebacking, beauty, big black cock, big cock, couple, cum, cumshot, femboy

KeekAss

Pretty Shemale Jerking Live On Cam

Categories: amateur, anal, beauty, big cock, femboy, handjob, homevideo, jerking, masturbation, nipples

XXXDan

BIG COCK INVADES TIGHT SHEMALE TRAP SISSY SLUT ASS

Categories: ass, big ass, big cock, gay, hardcore, lingerie, sissy, slut, tight

ShemaleZ

Really Tiny Dick Shemale Fucking Her Ass - Sissy Big Ass Milf

Categories: amateur, ass, big ass, hd, masturbation, mature, milf, redhead, sissy, solo

xHamster

misr4 - sissygasm anal masturbation

Categories: anal, anal toying, crossdressing, cum, cumshot, dildo, hd, lingerie, masturbation, orgasm

TrannyOne

Karen Dior in action

Categories: anal, ass, big cock, blowjob, classic, crossdressing, dick, hardcore, jerking, lingerie

aShemaleTube

VaneSsaBiTCHx & sa Copine RUBy avec un Client à MontParnasse [13oct23] PcTrv75

Categories: bimbo, blowjob, crossdressing, french, funny, group sex, hd, mature, sissy, slut

xHamster

Bangin' My Trans Girlfriend in the Kitchen

Categories: amateur, anal, barebacking, big ass, big cock, blowjob, condom, crossdressing, facial, girlfriend

xHamster

Marzia in fire

Categories: anal, anal toying, big ass, bitch, crossdressing, dildo, femboy, fetish, french, hardcore

xHamster

Elena Plays with Her Butt with a Bottle of Ouzo Plomari Tearing It and Screaming While Wearing a Red Mini Dress

Categories: amateur, anal, ass, bottle, dress, greek, hd, homevideo, masturbation, mature

xHamster

greek horny sissy has anal orgsm

Categories: anal, bbw, big tits, greek, hd, pantyhose, pretty, sissy, solo, vibrator

aShemaleTube

My Small dick 👠

Categories: asian, crossdressing, femboy, hd, homevideo, ladyboy, sissy, small cock, solo, teen (18+)

xHamster

Shemale crossdresser flashes and masturbates in public store wearing sexy lingerie

Categories: anal, anal toying, big ass, big cock, crossdressing, cumshot, flashing, hd, lingerie, masturbation

KeekAss

Smukke ash-blonde she-male kommer på sin seng i lingeri

Categories: amateur, ass, beauty, big ass, big cock, big tits, blonde, cumshot, feet, handjob

KeekAss

Sissy Crossdresser Cruelly Penetrated by Landlord

Categories: amateur, anal, blowjob, brunette, crossdressing, domination, femboy, fetish, hardcore, hd

aShemaleTube

Leni fuck

Categories: anal, big cock, hd, sissy, toys, uniform

aShemaleTube

Cumming A Little Bit Watching Myself And Handling My Own Body

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

xHamster

The Best Step Daddy Deepthroat Blowjob I Have Ever Had!

Categories: asian, blowjob, couple, crossdressing, cum, cum in mouth, daddies, deep throat, domination, face fucking

xHamster

I fuck my ass with my favorite dildo

Categories: amateur, anal, anal toying, ass, beauty, big cock, dildo, femboy, hd, latina

xHamster

Elena Andreou Crazy Slut Cross From Greece Plays with Her Butt with a Bottle of Ouzo Plomari Tearing It and Screaming

Categories: amateur, anal, ass, big ass, bottle, crazy, greek, hd, homevideo, masturbation

xHamster

Lovense vibrating in my ass, maximum power

Categories: amateur, anal, anal toying, ass, bitch, blonde, crossdressing, domination, femboy, hd

TrannyOne

taiwan sissy slut fuck in public toilet

Categories: amateur, asian, crossdressing, homevideo, model, outdoor, public, sissy, slut, small tits

KeekAss

Ria Bentley Strokes Her Fat GirlCock and Shoots Her Sperm

Categories: amateur, beauty, big cock, cum, cumshot, fat, fetish, huge cock, jerking, ladyboy

aShemaleTube

Plugging Sissy Maid, Sissy Onyx

Categories: anal, clamp, hd, maid, nipples, sissy, slut, submissive, uniform

TrannyOne

marktheWeakling HOGTIED TO GIVE HEAD

Categories: amateur, bdsm, blowjob, bondage, crossdressing, gay, hairy, hd, hogtied, maledom

aShemaleTube

Cute Young Bitchboi with a Big White Dildo

Categories: amateur, anal, ass, crossdressing, cute, dildo, gaping hole, hd, lingerie, sissy

ShemaleMovie

Hardcore compilation of goth sissy Jade Madison getting drilled

Categories: amateur, american, anal, ass, babe, barebacking, bdsm, beauty, big ass, big cock

xHamster

Big Ass MILF Tranny Streching Her Ass - Sissy 04

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

KeekAss

5 of My Most Super-naughty, Bad, Girly TOMBOY Nymph with a Pipe MEATY Cum-shots in Latex NYLON

Categories: amateur, bikini, bukkake, compilation, cosplay, crossdressing, cumshot, cute, dick, femboy

VideoSection

Sissy transvestite newhalf enjoys sissy training and anal play

Categories: anal, asian, beauty, crossdressing, femboy, ladyboy, masturbation, sissy, transvestite

XXXDan

Once a sissy whore always a whore

Categories: anal, creampie, gay, hardcore, sissy, slut

xHamster

Mrs Samantha Spanks and Teases slut Els, tied down with a chain

Categories: 3some, amateur, anal, anal toying, bdsm, crossdressing, domination, dutch, hd, high heels

KeekAss

KellyCD666 Christmas bounty! Jism in My Large Bootie! Total flick!

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

aShemaleTube

Hot Sissy Using Her Anal Beads

Categories: amateur, anal, beads, dildo, hd, lingerie, masturbation, sissy, solo, teen (18+)

aShemaleTube

Slutty Fat Ass Melody Sucks, Rides, Gapes and Cums

Categories: amateur, anal, ass, barebacking, bbw, big ass, blowjob, compilation, creampie, cum

aShemaleTube

Foxy leopard print bodystocking

Categories: big ass, blonde, bodystocking, femboy, fetish, hd, ladyboy, lingerie, pantyhose, sissy

xHamster

Who Want to Play with Sexyfilomena?

Categories: amateur, anal, canadian, crossdressing, cum, cute, dildo, hd, high heels, homevideo

xHamster

Foot Worship & Trampling Cumshot Sissy Licks Cum of Mistress's Feet

Categories: amateur, big cock, british, couple, cum, cumshot, domination, feet, femboy, femdom

xHamster

Tgirl Riley sucking long and fucking long

Categories: amateur, anal, barebacking, big cock, crossdressing, cute, dick, dutch, gaping hole, hd

xHamster

last live stream

Categories: anal, bbw, big ass, big clit, big cock, big tits, crossdressing, cum, cumshot, danish

aShemaleTube

Leggy Femboy Video Shoot

Categories: amateur, blonde, blowjob, compilation, crossdressing, cumshot, femboy, futanari, hd, lingerie

xHamster

Sissy Trans sucking her neighbor's husband's BBC cock

Categories: amateur, american, big black cock, big cock, blonde, blowjob, crossdressing, dick, feminization, hd

aShemaleTube

Travesti Estado de mexico

Categories: anal, fetish, hd, homevideo, mexican, sissy

TrannyOne

yellow top and short flower skirt ride huge dildo precum and cum hard

Categories: amateur, big cock, cum, cumshot, huge dildo, lingerie, mature, milf, model, sissy

aShemaleTube

Beautiful Butt Plugs in My Ass Compilation

Categories: anal, ass, beauty, big ass, compilation, dildo, masturbation, mature, pussy, sissy

ShemaleZ

Trans Fucks Asian Tgirl Into A Dick-down Stupor With Ria Bentley

Categories: american, anal, asian, assfucking, barebacking, brunette, crossdressing, dick, hd, lace

aShemaleTube

Foot and ass worship for a sissy

Categories: amateur, ass, crossdressing, feet, fetish, hd, homevideo, licking, mature, sissy

xHamster

The Tranny MILF - My Ass Dripping Cum After a Sissygasm

Categories: anal, ass, big ass, cum, fishnet, fucking machine, hd, masturbation, milf, pussy

xHamster

Sexy Maid Dress and Satin Panties, Sissy Clity Cum End

Categories: amateur, clit, cum, dress, hd, lingerie, maid, panties, satin, sissy

aShemaleTube

Shemale Foot Fetish

Categories: crossdressing, feet, femboy, fetish, hd, ladyboy, sissy, toes

aShemaleTube

dildo at the mirror

Categories: amateur, anal, ass to mouth, crossdressing, dildo, hd, lingerie, mirror, sissy, small tits

aShemaleTube

You are a good boi JOI!

Categories: amateur, crossdressing, cumshot, femboy, fetish, hd, joi, lingerie, masturbation, model

Pornstars: Viper

aShemaleTube

Butt Plugging for beginners

Categories: ass, buttplug, crossdressing, feminization, hd, lingerie, sissy, toys

TrannyOne

Sissy Transformation Story Ep 1

Categories: hardcore, sissy, story

aShemaleTube

Rebecca Farron - 2025.03.25 cam session part 1

Categories: amateur, crossdressing, femboy, hd, ladyboy, lingerie, sissy, solo, stockings, toys

ShemaleMovie

Sissyheartslave takes a serious plug from her master while dressed to please

Categories: american, anal, anal toying, ass, bdsm, fishnet, high heels, master, sissy, slave

xHamster

Tranny jerking off his cock.

Categories: amateur, bbw, big ass, big cock, big tits, crossdressing, cum, cumshot, cute, dick

xHamster

Nagawasan Og Sperms Cells Ang Reyna Para Pud Kay Daddy

Categories: anal, asian, ass, beauty, big ass, blonde, cum, cute, daddies, dick

xHamster

Rigid3d Intense Anal Riding Delicious Hot Big Ass Fucking Huge Monster Cock Intense Sex Sweet Tasty Pleasure

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xHamster

Tranny MILF in Fishnet Fucking Her Ass with Big Toys

Categories: anal, ass, big ass, big cock, cumshot, dildo, fishnet, fucking machine, hd, masturbation

xHamster

Marilyn McRow Making Milk in Minutes (Barbarella Rossa)

Categories: amateur, big cock, big tits, british, crossdressing, cumshot, european, hd, homevideo, lingerie

Pornstars: Barbarella

xHamster

Solo fun after training

Categories: amateur, big cock, cum, femboy, funny, handjob, hd, ladyboy, lingerie, polish

xHamster

Teasing Tyrell's BB12"NC rock hard for cum with a slow silky QOS panties striptease in my 9" BBC SLUT platform stiletto heels.

Categories: american, ass, big ass, big black cock, bitch, blonde, cosplay, cum, fetish, hd

TrannyOne

Fetish Goddess Slavena und ihre Sissy-Schlampe

Categories: big cock, blonde, boots, crossdressing, fetish, goddess, ladyboy, latex, lingerie, sissy

XXXDan

Rich Sissy

Categories: anal, asian, blowjob, doggystyle, licking, rich, sissy

xHamster

smoking lumina

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xHamster

Outside in pantyhose leotard miniskirt neighborhood walk.

Categories: american, crossdressing, dress, fetish, hd, high heels, ladyboy, lingerie, miniskirt, outdoor

xHamster

Sissi Stacy Deepthroat Sucking at the Forest

Categories: amateur, big tits, blowjob, crossdressing, deep throat, dildo, forest, hd, high heels, latex

xHamster

Mag jakol palagi ang dalagita para pud sa iyahang taga hanga

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aShemaleTube

CdTina draining #4

Categories: amateur, big cock, blowjob, crossdressing, cumshot, fetish, hd, long nails, mature, sissy

KeekAss

toying with 12in meaty faux-cock in my culo - sissy bitch

Categories: amateur, anal, ass, big ass, bitch, crossdressing, cumshot, dick, dildo, hd

aShemaleTube

Sexy crossdresser in nylon stockings and heels. hands free cum in castity cage

Categories: amateur, big cock, cage, crossdressing, cum, cumshot, femboy, fetish, hd, high heels

KeekAss

Hottest She-Male money-shot Compilation

Categories: amateur, anal, anal toying, ass, assfucking, big cock, big tits, brunette, compilation, crossdressing

TrannyOne

Suspended Sissy Slave Boy Slut Titplay and Cockjerk

Categories: bdsm, big cock, boy, crossdressing, dick, domination, gay, hd, masturbation, sissy

aShemaleTube

My first intro video sexy blonde t-girl with huge cock showing you her pretty smile. BWC

Categories: big cock, blonde, crossdressing, femboy, hd, huge cock, ladyboy, pretty, sissy, solo

aShemaleTube

Adorable Trap, Strips, Plugs Her Fat Ass and Jerks off for You

Categories: adorable, amateur, anal, anal toying, ass, big ass, big cock, crossdressing, cum, cumshot

KeekAss

I'm a Highly Servant Sissy Bi-atch that drinks your Jism - Onlyfans Veronica Sanders

Categories: amateur, asian, bedroom, best friend, bisexual, blowjob, brunette, colombian, couple, cum

xHamster

STAY EDGING WITH LEITAOXIV! NO CUM FOR ME!

Categories: asian, beauty, big cock, crossdressing, cum, edging, femboy, feminization, hd, japanese

xHamster

Sissy Feminized and Fucked by Mistress Pixie

Categories: amateur, american, anal, crossdressing, domination, femboy, feminization, hd, lingerie, mistress

xHamster

Big Hairy Cock fuck a Bubble Sissy Ass . Macho and a crossdresser travesty

Categories: anal, ass, big ass, big cock, crossdressing, cum, dick, hairy, hd, italian

aShemaleTube

Kitty Valentino in boots cums

Categories: big cock, boots, brunette, cum, cumshot, femboy, high heels, homevideo, lingerie, masturbation

KeekAss

Sissy Scarlet Sky Jizz Compilation!

Categories: amateur, anal, blonde, compilation, cosplay, cum, cumshot, cute, handjob, hd

KeekAss

Ass Fucking getting off in motel #5

Categories: amateur, anal, asian, ass, assfucking, crossdressing, dildo, gaping hole, handjob, hd

TrannyOne

Sissy slave slut Webcam bitch

Categories: amateur, bdsm, bitch, crossdressing, domination, gay, handjob, hd, masturbation, sissy

aShemaleTube

crossdresser big ass dildo

Categories: amateur, anal, big ass, crossdressing, dildo, lingerie, mature, sissy, solo, stockings