Sissy Shemale Videos » 32

aShemaleTube

Mimsy corset self facial cumshot and masturbation

Categories: amateur, corset, crossdressing, cumshot, facial, femboy, hd, homevideo, ladyboy, masturbation

aShemaleTube

Hot me skykitty ladyboy fucked by big black cock

Categories: anal, big ass, big black cock, big cock, creampie, crossdressing, cumshot, femboy, hd, ladyboy

KeekAss

Kellystar518 in HARD BLACK COCK vs SISSY ASS

Categories: anal, ass, big black cock, big cock, bitch, black, cheating, crossdressing, dick, domination

KeekAss

Sexy Blonde Strokes Cock

Categories: amateur, asian, beauty, big cock, blonde, cei, crossdressing, cute, dick, homevideo

HClips

Cam Model - Emmysdesires Compilation, Sissy Fuked By Her Fucking Machine

Categories: amateur, anal, big ass, big tits, brunette, compilation, fucking machine, hd, model, sissy

TrannyOne

Sissy Monika CD in Chastity cumming on a Huge black Dildo

Categories: amateur, anal, anal toying, ass, assfingering, big black cock, black, brunette, cage, crossdressing

xHamster

Colorful Videos: Showcasing Cute Body and Sexy Dresses

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

KeekAss

Fellow To Monstrous Booty Sissy Transformation

Categories: amateur, big ass, big black cock, big cock, booty, crossdressing, femboy, feminization, fetish, hd

KeekAss

Transgender Kelsey Teachers Porked Wet Switch Sides Cowgirl

Categories: amateur, anal, beauty, big ass, cowgirl, cum, femboy, fetish, hardcore, homevideo

xHamster

Hot Crossdresser Bailey Wilde Whipped

Categories: amateur, american, anal, bdsm, beauty, crossdressing, cum, domination, femboy, fetish

xHamster

Crossdresser and Trans Woman Using Fucking Machine - Compilation 6

Categories: amateur, american, anal, barebacking, big ass, big cock, blowjob, compilation, crossdressing, cute

XXXDan

Sissy White Nylons Show With Handjob And Final Cumshot

Categories: amateur, big cock, creampie, cumshot, gay, handjob, lingerie, masturbation, nylon, sissy

KeekAss

So Delicate And Sensual

Categories: amateur, ass, beauty, boyfriend, crossdressing, cute, femboy, homevideo, jerking, kitchen

aShemaleTube

Sissy BarbieLoki Dildo Play and Cumshot

Categories: barebacking, cage, cumshot, dildo, femboy, hd, homevideo, lingerie, redhead, sissy

KeekAss

She-Male taunting herself in missionary pose flashing her Soles

Categories: amateur, anal, assfucking, big ass, big tits, boy, feet, femboy, flashing, hd

aShemaleTube

Fast as Fuck boy

Categories: amateur, anal, big cock, boy, crossdressing, femboy, fetish, hd, homevideo, lingerie

xHamster

Sequel to Sissy Slut Middle East Hotel Adventure - Ejaculation in a Tight Condom on the Hotel Balcony - Full Version

Categories: amateur, anal, ass, balcony, bathroom, condom, crossdressing, cum, cumshot, handjob

xHamster

Red Bra and Black Seethrough Blouse

Categories: amateur, black, bra, crossdressing, hd, lingerie, mature, sissy, solo

XXXDan

Russian shemale domina sissy slave

Categories: bdsm, dominatrix, russian, sissy, slave

xHamster

Your blonde sissy getting a huge cum

Categories: amateur, beauty, big cock, blonde, colombian, crossdressing, cum, cumshot, hd, ladyboy

KeekAss

Sissy nurse Kitty rails until you jizm

Categories: amateur, anal, anal toying, beauty, big ass, big cock, brunette, cosplay, cum, cumshot

aShemaleTube

Infatable Butt Plug 1

Categories: amateur, anal, buttplug, fetish, hd, homevideo, sissy, small cock, solo, toys

ShemaleMovie

Crossdresser anal, ladyboy ass

Categories: amateur, anal, ass, asslick, big ass, big cock, crossdressing, cum, femboy, jizz

xHamster

Celine Laffite again and again in slutty mode

Categories: amateur, anal, barebacking, beauty, creampie, french, hardcore, hd, milf, moaning

aShemaleTube

Second video

Categories: amateur, anal, bbw, femboy, hd, sissy, small cock, solo, toys

aShemaleTube

Big cock sissy pissing and wanking in the bathroom in lingerie

Categories: amateur, bathroom, big cock, big tits, crossdressing, homevideo, lingerie, masturbation, mature, model

aShemaleTube

[no porn] Pink Easter Bunny Vlog without App

Categories: amateur, asian, bunny, chinese, crossdressing, fetish, hd, homevideo, latex, model

aShemaleTube

dizzy miss sizzy bound and caned

Categories: bdsm, bondage, bound, crossdressing, femdom, gagging, hd, mistress, sissy

KeekAss

Ginger-Haired sissy rectally swallowing a beer by the open window at night

Categories: amateur, anal, crossdressing, cum swallowing, enema, exhibitionist, extreme, femboy, hd, lingerie

aShemaleTube

Naughty femboy pulls girls panties out of her pussy

Categories: amateur, anal, femboy, hd, homevideo, naughty, panties, pussy, sissy, solo

xHamster

Colorful Mismatched Socks and a Piggy Toe

Categories: amateur, big ass, cumshot, hd, masturbation, sissy, socks, solo, stockings, tranny

xHamster

Asian sissy Eva is your peacock tonight

Categories: asian, canadian, chinese, crossdressing, hd, ladyboy, lingerie, mature, pantyhose, sissy

xHamster

Greek Whiteboi Limp Clitty leaking from bouncing on Big black dildo

Categories: amateur, anal, big black cock, black, clit, crossdressing, dildo, femboy, feminization, greek

aShemaleTube

Webcam slut stretching her ass with huge dildos

Categories: amateur, anal, ass, big ass, compilation, femboy, hd, homevideo, huge dildo, ladyboy

xHamster

Dreaming of Marriage: Building a Future with a Girl

Categories: amateur, american, beauty, big ass, big cock, big tits, crossdressing, fantasy, femdom, feminization

aShemaleTube

More dancing for Daddies

Categories: crossdressing, daddies, dancing, masturbation, panties, sissy

KeekAss

Kellystar518 - Summer Punch

Categories: amateur, amazing, beach, beauty, brunette, buttplug, cosplay, crossdressing, dress, fantasy

KeekAss

Living Silicone Ditzy Damsel - miss Eva Mae - Transformation Masculine to Doll

Categories: amateur, bimbo, blonde, crossdressing, doll, fake tits, hd, homevideo, mask, sissy

xHamster

Beautiful trans girl fucks milf stepmother while stepson records her

Categories: amateur, bbw, beauty, big ass, big cock, blowjob, crossdressing, cum, hd, mature

KeekAss

Sissy harley quinn despairingly needs manhood

Categories: amateur, chubby, cosplay, crossdressing, femboy, hd, sissy, solo, toys, transsexual

aShemaleTube

Shemale wants to fuck her quickly

Categories: asian, barebacking, chinese, femboy, hd, homevideo, lingerie, sissy, teen (18+), toys

aShemaleTube

[R18+] Pink Easter Bunny Solo Cum [3rd]

Categories: amateur, anal, asian, bunny, crossdressing, cum, cumshot, fetish, hd, homevideo

xHamster

Angel Rios Looking so Beautiful Especially with a Huge Cock

Categories: amateur, amazing, american, beauty, big cock, crossdressing, hd, huge cock, ladyboy, latina

aShemaleTube

[no porn] Pink Bunny Sissy seduction moves on floor

Categories: amateur, asian, bunny, crossdressing, fetish, hd, homevideo, latex, model, pantyhose

ShemaleZ

Sissy Teen Ochani Fucks Dildo Vigorously On Table And

Categories: amateur, brunette, dildo, hd, sissy, solo, table, teen (18+), toys, webcam

aShemaleTube

Sissy Daytime Balcony Tease

Categories: balcony, hd, indian, public, sissy, small tits, tease, transsexual

ShemaleMovie

Raunchy sissy trap gets off on her own manhood

Categories: jerking, masturbation, raunchy, sissy

xHamster

MY GIRLFRIEND ALWAYS TALKS TO ME WHEN SHE FINISHES WORK BECAUSE SHE LIKES IT TOO MUCH WHEN I LEAVE HER STUFFED WITH CUM AND SHE SEES HOW IT SLIPS OFF

Categories: amateur, barebacking, beauty, big ass, couple, cum, femboy, fetish, girlfriend, hd

xHamster

After the party,fucked her asshole

Categories: anal, ass, crossdressing, dildo, domination, hd, high heels, ladyboy, masturbation, party

xHamster

Milking Machine cumshot

Categories: amateur, cum, cumshot, domination, fetish, handjob, hd, masturbation, milk, sissy

xHamster

Destroyed asshole gaping

Categories: anal, ass, barebacking, big ass, big cock, big tits, blonde, buttplug, crossdressing, feet

xHamster

Tgirl Missy Smoking Sexy

Categories: amateur, big ass, blonde, hd, sissy, smoking, solo, tgirl

xHamster

WEBCAM HOT CUTE SISSY FEMBOY BOOTY REDHEAD BUBBLE BUTT SOFT SMOOTH SKIN WHITE BIG ASS SEXTING MODEL CROSSDRESSER KITTY

Categories: amateur, american, ass, beauty, big ass, blonde, booty, crossdressing, cute, femboy

aShemaleTube

College Boy Meets Sissy At Bar And Then Fucks

Categories: amateur, anal, bar, big cock, blonde, boy, college, creampie, crossdressing, hd

KeekAss

It so great

Categories: amateur, anal, anal toying, ass, assfucking, blonde, crossdressing, feet, femboy, fetish

aShemaleTube

Femboy's Big Ass Sways in Erotic Dance

Categories: big ass, college, compilation, cosplay, crossdressing, cum, erotic, ladyboy, masturbation, pornstar

xHamster

Sissy Maid Self Bondage Predicament

Categories: bdsm, bondage, canadian, dildo, fetish, gagging, hd, high heels, latex, maid

aShemaleTube

sissy hypno 242

Categories: cum, music, sissy

xHamster

Foot Fetish Only, Amazing Sex Session Until Cum Like Asissy Slut

Categories: amateur, amazing, anal, big ass, cum, dildo, feet, fetish, hd, masturbation

xHamster

Riding huge dildo with final sissy squirt

Categories: amateur, anal, crossdressing, dildo, femboy, hd, homevideo, huge dildo, masturbation, prostate

xHamster

SISSYBOI FEMBOI RIDING DILDO WEARING FISHNET

Categories: amateur, anal, anal toying, big ass, booty, crossdressing, dildo, fishnet, german, hd

KeekAss

Trans nymph piss and spunk from phat fake penis

Categories: amateur, anal, bdsm, big cock, crossdressing, dick, femboy, fetish, fisting, hd

aShemaleTube

There for Him Until the End of Time

Categories: amateur, anal, barebacking, beauty, blonde, blowjob, cum, cum in mouth, handjob, hd

aShemaleTube

Chinese sissy Alicexiao high heel boots

Categories: amateur, anal, asian, boots, chinese, hd, high heels, masturbation, sissy, stockings

xHamster

Crossdresser Carrie jerks off and cums in cute lingerie

Categories: american, car, crossdressing, cum, cumshot, cute, hd, homevideo, lingerie, masturbation

xHamster

Sissy Kanisa Crossdresser Anal Penetration with White Anal Bead Dildo

Categories: amateur, anal, asian, ass, creampie, crossdressing, dildo, hd, ladyboy, masturbation

KeekAss

Large Weenie Ladyboy Stroking On Web Camera

Categories: amateur, beauty, big black cock, big cock, crossdressing, dick, femboy, gaping hole, hd, homevideo

xHamster

German Teen tranny fucks her ass in dirndl with dildo

Categories: amateur, anal, anal toying, ass, big cock, crossdressing, dildo, dress, german, hd

KeekAss

FtM Crossdress Taunt, Fap Missionary & Rear End

Categories: amateur, big clit, black, brunette, crossdressing, doggystyle, dress, fat, fetish, fingering

KeekAss

sissy crossdresser on webcam with speculum in her cooter fuck-hole

Categories: amateur, anal, big ass, big cock, blonde, crossdressing, handjob, hd, lingerie, masturbation

aShemaleTube

Vlog #6: Sexy Photoshoot and Masturbation - Veronica Sanders

Categories: big clit, colombian, cumshot, dick, feet, high heels, homevideo, lingerie, masturbation, photoshoot

xHamster

Sissy Destroys Her Pussy 3

Categories: anal, crossdressing, dick, dildo, hd, latina, lingerie, masturbation, pussy, sissy

xHamster

Sexy Gold Shiny Bullet Bra

Categories: amateur, bra, crossdressing, hd, lingerie, mature, sissy, solo, stockings

xHamster

Tiny dick sissy Alicia Smallz

Categories: amateur, dick, hd, masturbation, sissy, small cock, solo, tiny dick

aShemaleTube

Cum with cage and Dildo Fuck

Categories: cage, crossdressing, cum, cumshot, dildo, hd, sissy, toys

aShemaleTube

SUMM SISSY COCK RUBBING

Categories: crossdressing, dick, hd, masturbation, rubbing, sissy

ShemaleZ

Sissy Bitch

Categories: american, big ass, bitch, crossdressing, hd, latina, mature, sissy, solo, toys

KeekAss

Taking A Chance Juicy Denial With Dommy Bee Jerk Off Instructions Teaser

Categories: amateur, asian, beauty, big cock, crossdressing, cum, cumshot, cute, denial, dirty talk

KeekAss

Deepthroat my thick bone like a excellent tiny sissy mega-bitch

Categories: anal, big ass, big cock, big tits, bitch, blonde, blowjob, brunette, compilation, crossdressing

aShemaleTube

I fucked my sissypussy while my clit is in a pink chastity and my gf is out with her gf‘s💖

Categories: clit, dildo, girlfriend, hd, humiliation, sissy

VideoSection

Stockings, sissy crossdresser

Categories: ass, big ass, crossdressing, european, high heels, lingerie, outdoor, secretary, sissy, small cock

ShemaleMovie

Amateur femboy CD takes a risk outdoors in heels and mini dress, narrowly escaping discovery

Categories: amateur, ass, big ass, brazilian, crossdressing, dress, femboy, high heels, homevideo, ladyboy

xHamster

Alt Tgirl Masturbates for You

Categories: amateur, beauty, crossdressing, cum, deep throat, dildo, feet, femboy, fetish, hd

aShemaleTube

Blue Touch

Categories: big cock, blonde, cumshot, homevideo, jeans, lingerie, masturbation, sissy

xHamster

Sissy crossdresser solo bunny

Categories: asian, bunny, cosplay, crossdressing, hd, ladyboy, masturbation, pantyhose, pov, rough

xHamster

Nylon-terry 2

Categories: amateur, anal toying, beauty, crossdressing, european, hd, homevideo, lingerie, masturbation, nylon

aShemaleTube

Upskirts to flash my sissy ass in 9" BBC SLUT platform stiletto heels to tease BB12"NCs

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

KeekAss

Young Trans Has a Big Grubby Money-Shot

Categories: amateur, anal, big cock, brunette, crossdressing, cumshot, cute, dildo, femboy, hd

KeekAss

Your sick lil' fetish - Sissy trainer

Categories: anal, big cock, blonde, blowjob, brunette, compilation, cumshot, fetish, gangbang, gay

xHamster

Stefani Tarrago: Fucking a Shemale and Her Girlfriend

Categories: 3some, anal, blonde, cumshot, dick, dildo, girlfriend, hd, milf, outdoor

aShemaleTube

20250211

Categories: asian, barebacking, chinese, cumshot, femboy, hd, homevideo, lingerie, masturbation, sissy

KeekAss

Plow machine joy for sissy she-creature - Nokken, Marcel and Trotter

Categories: amateur, anal, anal toying, crossdressing, dildo, hd, huge dildo, sissy, toys, tranny

xHamster

Hot Blonde Crossdresser has Cock Rubbed by Guy's Feet

Categories: amateur, american, anal, barebacking, beauty, big cock, blonde, crossdressing, dick, domination

aShemaleTube

You should be licking feets of your beautiful mistress

Categories: beauty, big cock, crossdressing, domination, fetish, hd, licking, lingerie, masturbation, mistress

xHamster

Real Sissy Maid Service "Mopping the Floor"

Categories: american, crossdressing, fetish, hd, high heels, ladyboy, lingerie, maid, sissy, solo

aShemaleTube

Chat with BIG COCK shemales on Wachabate (Free Cams)

Categories: big cock, dick, hd, orgasm, sissy, slut, spit, tgirl, tranny, transsexual

KeekAss

Chinese Femboy Rails a Rock Hard Mean Dick

Categories: anal, anal toying, asian, chinese, cum, dick, dildo, femboy, hd, ladyboy

xHamster

Leggy Crossdresser in Nylon Stockings

Categories: abuse, amateur, crossdressing, cum, feet, hd, high heels, masturbation, nylon, secretary

aShemaleTube

Viper Fierce 70 insane cumshots compilation

Categories: anal, asian, big cock, compilation, crossdressing, cumshot, femboy, fetish, hd, latex

Pornstars: Viper

KeekAss

Huge Faux Mounds Crossdresser bikini carwash

Categories: amateur, bbw, big tits, bikini, cleavage, crossdressing, exhibitionist, fake tits, fetish, fishnet

xHamster

Sissy Maids Self Bondage Spiked Chastity Cage Torment for the Holidays

Categories: bdsm, bondage, cage, canadian, dildo, fetish, gagging, hd, high heels, holiday

KeekAss

Sissy solo have fun - femboy home alone

Categories: amateur, anal, boy, crossdressing, cute, femboy, feminization, funny, handjob, hd

PornGem

Rubber Sissy Strokes Her Shecock And Cums On Her Stockings

Categories: cum, cumshot, gay, latex, masturbation, rubber, sissy, solo, stockings, toys

aShemaleTube

LaurettaTr Italian Crossdresser Cum on Tits

Categories: amateur, barebacking, blowjob, creampie, crossdressing, cum, cum in mouth, cumshot, femboy, hd

aShemaleTube

Insane huge dildo - Part 5 (painful fart)

Categories: amateur, anal, farting, fetish, huge dildo, pain, sissy, stockings, toys

aShemaleTube

Pretty summer dress, nude pantyhose and heels

Categories: blonde, crossdressing, dress, femboy, hd, high heels, ladyboy, lingerie, nude, pantyhose

xHamster

Jenni plays with her toys to get her boyfriend hard

Categories: amateur, american, anal, big cock, boyfriend, fucking machine, hd, high heels, masturbation, nylon

xHamster

🔶️CAM⁴ BadBitch [⁷fev²⁵] VBx PcTrvProd⁹¹

Categories: amateur, big cock, bitch, compilation, crossdressing, cum, cumshot, french, hd, lingerie

KeekAss

Dominatrix does not let sissy spunk - Edging

Categories: amateur, dominatrix, edging, femdom, handjob, hd, sissy

aShemaleTube

Hung Spider-Girl cosplay edging🍆

Categories: ass, big ass, big cock, cosplay, edging, femboy, halloween, hd, homevideo, latina

aShemaleTube

Crossdresser mistress fuck her slut

Categories: crossdressing, domination, hd, homevideo, mature, mistress, sissy, slut

xHamster

Very beautiful legs and toes

Categories: bbw, beauty, hd, homevideo, legs, pov, sissy, solo, teen (18+), toes

KeekAss

Trans Taunted & Managed In Purity

Categories: amateur, anal, blonde, cage, crossdressing, fetish, fucking machine, hd, homevideo, lingerie

TrannyOne

Latex Mistress milks bound sissy's cock and feeds her cum

Categories: bdsm, bound, cum, dick, handjob, latex, mistress, sissy

xHamster

Merve Turkish Tgirl Sexy Blonde Sissy Stockings Tattoo Trans

Categories: barebacking, big ass, big cock, blonde, hd, masturbation, sissy, small tits, stockings, tattoo

xHamster

black pantyhose & lace bodysuit

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

xHamster

Msjamie is hot.... Stop slobbering.

Categories: amateur, american, anal toying, beauty, big tits, blonde, dildo, hd, masturbation, sissy

TrannyOne

Argentina Tranny Ts Perla Ate My Nut

Categories: amateur, anal, argentinian, barebacking, beauty, big black cock, big cock, black, blowjob, cum

xHamster

Huge glass plug ass VladAQueen Party 2

Categories: abuse, amateur, anal, anal toying, ass, bdsm, big ass, big cock, femboy, hardcore

aShemaleTube

crossdresser1 - DadaTrav

Categories: brunette, crossdressing, glasses, homevideo, lingerie, mature, pantyhose, redhead, sissy, stockings