Crossdressing Shemale Videos » 28

aShemaleTube

Scottish TS Sucking

Categories: amateur, big cock, blowjob, crossdressing, lingerie, scottish, stockings, sucking, transsexual

aShemaleTube

Long haired femboy trap plays with her dick

Categories: amateur, big cock, blonde, crossdressing, dick, dress, femboy, fetish, homevideo, long hair

aShemaleTube

Blonde in a little black dress, stockings and stripper heels

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

aShemaleTube

Tilia - Lisieux 2025

Categories: amateur, crossdressing, exhibitionist, hd, outdoor

aShemaleTube

bizarre life - outdoors

Categories: amateur, bizarre, crossdressing, fetish, outdoor, solo

JizzBunker

Sloppy Deepthroat and Gagging for Sissy

Categories: amateur, blowjob, crossdressing, deep throat, dildo, european, fetish, gagging, russian, sissy

KeekAss

Punk Sissy Frolicking & Sissygasm Dual Fuck Stick

Categories: amateur, anal, blonde, crossdressing, cumshot, cute, dildo, emo, femboy, goth

KeekAss

RileyDix wears a sundress taunts and filthy converses dirty dancing her large booty

Categories: amateur, beauty, big ass, booty, crossdressing, dancing, dirty, dirty talk, dress, hd

VideoSection

Young sissy, amateur crossdresser

Categories: amateur, american, anal, anal toying, ass, babe, bdsm, beauty, big ass, crossdressing

aShemaleTube

Pervert sissy femboy night dildo show

Categories: asian, crossdressing, cumshot, dildo, femboy, hd, homevideo, lingerie, masturbation, model

Pornstars: Viper

aShemaleTube

Goth Princess Whore Tiffany Minx - Male Voice Over Story Slow Motion Blow Job

Categories: amateur, blowjob, cage, crossdressing, cumshot, domination, femboy, goth, pornstar, sissy

Pornstars: Tiffany Mynx

XXXDan

Chubby Cheap Sloppy Pig Sissy Lara White Brainwashed Feminized Sissified Anal Slut

Categories: amateur, anal, bbw, beauty, big ass, chubby, crossdressing, cumshot, european, gaping hole

KeekAss

FEMBOY ENDED SANS ARMS

Categories: amateur, anal, assfucking, crossdressing, cumshot, cute, femboy, femdom, fetish, first time

KeekAss

Cross dresser frigs and shoots a load witnessing pornography then slurps it up

Categories: amateur, ass, assfingering, assfucking, big cock, boy, brunette, crossdressing, cum, cumshot

aShemaleTube

crossdressing maid

Categories: crossdressing, maid, vintage

aShemaleTube

Shemale fucks shemale in the garden

Categories: amateur, crossdressing, garden, hd, latex, mature, outdoor

aShemaleTube

Mature Sissy Crossdresser Maddi Takes Raw Cock

Categories: amateur, barebacking, big ass, blowjob, crossdressing, dick, mature, sissy

ShemaleMovie

Hd videos, shemale fucks guy

Categories: amateur, anal, beauty, big cock, crossdressing, cum, fishnet, hd, high heels, japanese

XXXDan

Cd anal fuck machine sex

Categories: amateur, anal, crossdressing, dildo, hardcore, huge dildo, lingerie, orgasm, russian, slut

KeekAss

Platinum-Blonde trap tears up cucumber

Categories: amateur, anal, assfucking, blonde, boots, booty, crossdressing, cucumber, dildo, food

TrannyOne

Tattooed Daddy Barebacks his Sissy Boy

Categories: anal, anus, ass, bdsm, bondage, boy, crossdressing, daddies, gay, lingerie

aShemaleTube

Another nice wank

Categories: amateur, crossdressing, cumshot, hd, homevideo, masturbation, mature, solo, stockings, wanking

ShemaleMovie

Big ass shemale, beautiful transgender

Categories: 3d, amateur, anal, animation, anime, asian, ass, babe, barebacking, bbw

XXXDan

Im not your friends wife, For those who know

Categories: amateur, big clit, crossdressing, feet, fetish, french, friend, high heels, lingerie, masturbation

XXXDan

The trans Jessica Moon rides the cock of the transvestite Bailey Wilde

Categories: amateur, anal, bdsm, beauty, big cock, crossdressing, dick, hardcore, high heels, lingerie

KeekAss

My sissy transformatoin

Categories: amateur, anal, assfucking, brunette, compilation, crossdressing, czech, dildo, hd, masturbation

KeekAss

Orgy machine makes me jizz

Categories: amateur, anal, anal toying, crossdressing, cum, cumshot, dildo, doggystyle, fucking machine, gaping hole

KeekAss

An alien get out off my butt hole

Categories: alien, amateur, anal, ass, crossdressing, lingerie, stockings, toys

aShemaleTube

Ruby's Cumshot Compliation 2

Categories: amateur, big cock, compilation, crossdressing, cumshot, hd, lingerie, masturbation, mature, webcam

aShemaleTube

Naughty bitch 2 - Brenna Knight - Kik: brennamason13

Categories: bitch, blowjob, crossdressing, femboy, hd, homevideo, naughty, sissy

XXXDan

Showing My Big Veiny Testicles And Hairy Close-Up- Young Man

Categories: anal, big cock, black, close up, crossdressing, cute, daddies, gay, hairy, handjob

aShemaleTube

Piss on thigh boots and maid

Categories: boots, crossdressing, hd, homevideo, maid, mature, pissing

KeekAss

lily starlet tgirl gimp made to fart on vid and plow chest nymph

Categories: amateur, anal, brunette, clit, crossdressing, cum, cute, doll, farting, feminization

KeekAss

Observe how I jerk, I think you like my monstrous fuckpole

Categories: amateur, big cock, crossdressing, dick, handjob, hd, homevideo, huge cock, joi, lingerie

TrannyOne

Crossdresser with fake boobs fucking hot

Categories: anal, ass, big cock, bisexual, blonde, blowjob, crossdressing, dick, european, fake tits

aShemaleTube

Old housewife Serge Lusin. 2025vb

Categories: amateur, american, big ass, crossdressing, european, housewife, ladyboy, milf, old, sissy

aShemaleTube

Submissive Sissy crossdresser fucked by BBC - she is a bitch4

Categories: amateur, beauty, big black cock, bitch, blowjob, compilation, crossdressing, desi, european, femboy

JizzBunker

Transvestite tranny sounding urethral lingerie toys dildo 8

Categories: bdsm, big cock, crossdressing, dildo, fisting, gaping hole, gay, handjob, hardcore, lingerie

TrannyOne

Shemale Porn Video Jane Gets A Invite To Jennys Party

Categories: anal, blonde, blowjob, crossdressing, domination, group sex, hardcore, mature, party, rimjob

aShemaleTube

pink small limp clitty in a smallest chastity cage kiss

Categories: cage, crossdressing, kissing

KeekAss

Domina makes gimp full salute their marked abdomen using a Bad Dragon plaything

Categories: amateur, anal, belly, crossdressing, dominatrix, fetish, hd, kinky, mistress, stockings

KeekAss

Tgirl Rubs Huge Cock Solo

Categories: amateur, beauty, brunette, close up, crossdressing, cute, ebony, femboy, futanari, glasses

TrannyOne

Karen Dior, shemales and CDs

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

KeekAss

Smoking blond cockslut - 1

Categories: amateur, blonde, crossdressing, dick, latex, lingerie, smoking, stockings, webcam

aShemaleTube

Cum explosion on leg

Categories: amateur, crossdressing, cum, cumshot, dick, femboy, hd, homevideo, masturbation, mature

aShemaleTube

ola gia sena 20240325_083836

Categories: amateur, big ass, crossdressing, fetish, hd, lingerie, mature, pantyhose, sissy, solo

JizzBunker

Moaning sissy rebecca fucks her asshole with a big dildo and uses big but plug to fill her lovely ass. end with cum

Categories: amateur, anal, ass, beauty, big ass, big cock, crossdressing, cum, cumshot, dildo

aShemaleTube

Mature CD waiting for some cock

Categories: amateur, crossdressing, dick, hd, mature, model, stockings, tranny, transsexual, wanking

aShemaleTube

webcams crossdress SVID_20240217_222406_1

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

aShemaleTube

Horny Younger Guy Fucks Trans In Motel Room

Categories: amateur, anal, barebacking, blonde, blowjob, creampie, crossdressing, hd, homevideo, lingerie

aShemaleTube

Luna Purple In Boots/eluna_84

Categories: amateur, boots, crossdressing, cumshot, fetish, hd, legs, masturbation, slut

KeekAss

Selenas XXL Rump Anal Invasion boinking Marathon Pin trio

Categories: amateur, anal, anal toying, ass, big ass, crossdressing, dildo, fucking machine, hd, ladyboy

TrannyOne

Toots La Femme

Categories: big tits, classic, crossdressing, fetish, hd, lingerie, mature, queen, sissy, stockings

KeekAss

Steaming Crossdresser Gets Plumbed by Banana

Categories: amateur, anal, banana, crossdressing, handjob, homevideo, masturbation

HClips

Appeared Wearing A Japanese Yukata...though Inside Was A Perverted Costume With Sissy Crossdresser

Categories: amateur, anal, asian, assfucking, cosplay, costume, crossdressing, dildo, hd, japanese

aShemaleTube

Dildo deepthroat traning

Categories: amateur, blowjob, crossdressing, deep throat, dildo, homevideo, hungarian, lingerie, sissy, small tits

XXXDan

Sizzling and Sensational: The Musical World of Crossdresser Kitty

Categories: beauty, big cock, big tits, caught, college, compilation, cosplay, crossdressing, cumshot, masturbation

KeekAss

Railing a Good-sized Dragon Fuck stick

Categories: anal, anal toying, beauty, big ass, bisexual, booty, crossdressing, cute, dildo, femboy

JizzBunker

Married man fucks a transvestite

Categories: anal, big cock, black, blowjob, brazilian, crossdressing, gay, hardcore, interracial, skinny

KeekAss

Lovely Femboy Rails Fake Penis While Noone Is Home

Categories: amateur, asian, brunette, crossdressing, dick, dildo, femboy, fetish, handjob, hd

KeekAss

My humid feets in the bathroom sissy juvia jolie

Categories: amateur, bathroom, beauty, crossdressing, feet, femboy, fetish, footjob, hd, homevideo

TrannyOne

Hot MILF with tight pussy without bra and panties reads a book

Categories: bra, crossdressing, dress, high heels, leggings, legs, milf, panties, pussy, spreading

aShemaleTube

Housewife Sveta Lusin. 2025ma

Categories: amateur, crossdressing, hd, housewife, ladyboy, mature, sissy, small cock, solo

aShemaleTube

TRANS GIRL. MARIKITA

Categories: american, anal, barebacking, beauty, big ass, big clit, big cock, crossdressing, femboy, feminization

KeekAss

Molten Trans Pops Firm!!!!

Categories: amateur, big cock, crossdressing, handjob, hd, kinky, masturbation, taboo, transsexual

JizzBunker

Sissy in diaper jerks off and cums

Categories: amateur, bdsm, crossdressing, cum, cumshot, diaper, fetish, high heels, latina, lingerie

KeekAss

Jaw-Dropping transgirl se corre con un vibrador pensando en su entrenador

Categories: amateur, big ass, brunette, bukkake, compilation, crossdressing, cum, cumshot, ebony, hd

aShemaleTube

Luna Dance And Tease, Submissive Slut- eluna_84

Categories: booty shake, crossdressing, dancing, fetish, hd, sissy, slut, solo, submissive, tease

TrannyOne

Take a SWalk on the Wildside

Categories: amateur, crossdressing, fat, gay, hairy, obese, transvestite

TrannyOne

Sauna cock suck with a tranny ends up being sexy

Categories: anal, crossdressing, dick, lingerie, sauna, sucking, tranny, webcam

aShemaleTube

Such A Good Gurl For Daddy

Categories: amateur, anal, barebacking, big ass, crossdressing, daddies, fetish, hd, homevideo, lingerie

aShemaleTube

Sexy black latex boots and fishnets compilation

Categories: black, blonde, boots, compilation, crossdressing, femboy, fetish, fishnet, hd, ladyboy

KeekAss

Spreading My Legs Like A Dirty Slut...

Categories: anal, barebacking, big cock, crossdressing, dirty, gay, legs, lingerie, old, sissy

JizzBunker

Dani Leg Monster Cumshot on Amazing Legs in Sexy Tan Pantyhose

Categories: amazing, big cock, crossdressing, cumshot, cute, feet, fetish, gay, high heels, legs

XXXDan

DeeDeeSlut69 takes it deep in her ass in the gym

Categories: amateur, anal, ass, big ass, crossdressing, dildo, gym, lingerie, slut, toys

aShemaleTube

Trans domina in heels fucks her sub after bareback fucked

Categories: ass to mouth, barebacking, crossdressing, domination, dominatrix, hd, high heels, pov, redhead, transsexual

KeekAss

Juggsy Dame Masker Z Bowl Stripper #4

Categories: amateur, big tits, blonde, brunette, compilation, crossdressing, fetish, hd, latex, lingerie

TrannyOne

Femdom latex MILF pegging crossdresser sub in his asshole

Categories: ass, big tits, crossdressing, femdom, fetish, latex, milf, pegging

TrannyOne

Little Blonde Trap swallows cum after blowjob

Categories: amateur, austrian, blonde, blowjob, creampie, crossdressing, cum, cum in mouth, cum swallowing, european

TrannyOne

Fat sissy in chastity using dildo

Categories: amateur, anal, anus, ass, bbw, booty, chubby, crossdressing, dick, dildo

aShemaleTube

Red and white minidress with black stockings

Categories: big cock, black, blonde, crossdressing, dress, femboy, hd, ladyboy, pantyhose, sissy

aShemaleTube

Foot Fetish & Sissy Femboy Dildo Play

Categories: asian, big cock, crossdressing, dildo, feet, femboy, fetish, hd, ladyboy, lingerie

Pornstars: Viper

KeekAss

japanese crossdresser nip ejaculation

Categories: cosplay, crossdressing, cumshot, fetish, handjob, hd, japanese, masturbation, solo

HDSex

Trans girlfriend enjoys playing with toys in bed, cums twice from dildo in her sissy trap ass

Categories: anal, anal toying, ass, bed sex, crossdressing, cum, dildo, femboy, girlfriend, moaning

XXXDan

Sexy boy with transparent lingerie skirt and long hair gets fucked in face to face position

Categories: amateur, anal, bdsm, beauty, boy, crossdressing, hardcore, lingerie, long hair, panties

TrannyOne

Legs In Slutty Leather Leggings

Categories: amateur, ass, crossdressing, fetish, homevideo, leather, leggings, legs, slut, tight

TrannyOne

fucking crossdresser bitch

Categories: amateur, anal, ass, ass to mouth, bdsm, bitch, crossdressing, domination, hd, ladyboy

aShemaleTube

Matures whores and a chubby guy

Categories: 3some, amateur, chubby, crossdressing, gay, group sex, hd, mature, obese, slut

KeekAss

Emo mistress feminize her tv cd sissy with female clothes pt2 HD

Categories: amateur, bdsm, clothed sex, crossdressing, dominatrix, emo, femdom, feminization, goth, hd

aShemaleTube

Crossdresser Anal Dildo Fucking Machine on Chair at Hotel Balcony

Categories: anal, anal toying, balcony, crossdressing, dildo, fucking machine, hd, hotel, lingerie

XXXDan

Smoking a cigarette

Categories: amateur, cigarette, crossdressing, dutch, smoking

aShemaleTube

Busty TS domina barebacks Black sub till cumshot on boots

Categories: ass to mouth, barebacking, big ass, big tits, black, boots, creampie, crossdressing, cumshot, dominatrix

KeekAss

Betty wears a Lollipop ring and high high-heeled shoes while talking!

Categories: amateur, blonde, crossdressing, dick, dirty talk, hd, high heels, lingerie, lollipop, masturbation

KeekAss

Fresh Playthings! Guts Have Fun Numerous Climax

Categories: amateur, anal, anal toying, assfucking, crossdressing, dildo, female orgasm, funny, hd, masturbation

TrannyOne

Change my flooded diaper

Categories: crossdressing, diaper, dick, gay, hd, locker room, small cock, striptease, transvestite

aShemaleTube

Tiziana White Vintage

Categories: amateur, anal, crossdressing, hd, lingerie, mature, stockings, toys, vintage, white

aShemaleTube

crossdress VID_VID_20241008_231013

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

KeekAss

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

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

aShemaleTube

webcams crossdress SVID_20240216_003954_1

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

KeekAss

28

Categories: amateur, anal, asian, blonde, boy, crossdressing, femboy, french, hd, italian

aShemaleTube

fisting and milking til cumshot

Categories: crossdressing, cumshot, fetish, fisting, hd, homevideo, masturbation, milk, model, pov

TrannyOne

Chubby Tgirl Alexandra fucking her womanized toyboy

Categories: amateur, bdsm, blowjob, chubby, creampie, crossdressing, cum, cum in mouth, cumshot, domination

aShemaleTube

LR Anal 4 - G038.1

Categories: anal, asian, crossdressing, femboy, hd, interracial, ladyboy, model, sissy, transsexual

aShemaleTube

Cosplayer's private with a man

Categories: blowjob, cosplay, crossdressing, cum, hd, japanese

aShemaleTube

The definitive Way to Prove You're Not Gay

Categories: crossdressing, femboy, gay, hd, lingerie, redhead, sissy, small tits, stockings

aShemaleTube

trans girl Stephanie sprays massive cumshot all over bathroom floor

Categories: amateur, bathroom, blonde, crossdressing, cumshot, femboy, glasses, hd, homevideo, lingerie

KeekAss

Insane Shark Ttuber Literally Cant Stop Tugging

Categories: amateur, asian, brunette, cosplay, crossdressing, cumshot, femboy, handjob, hd, ladyboy

KeekAss

attooed hefty parent hunk gobbling femboys boipussy, dt and sole fetish in fishnets

Categories: amateur, anal, blonde, blowjob, crossdressing, feet, femboy, fetish, fishnet, footjob

HClips

Playing In Hotel

Categories: amateur, crossdressing, hotel, stockings

aShemaleTube

Silk wrap dress

Categories: amateur, blonde, crossdressing, dress, femboy, fetish, hd, ladyboy, solo, uniform

aShemaleTube

Fucking Trans Kelsey Masters Raw and Masturbating - Compilation 1

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

VideoSection

Busty TV shemale pleasuring all her holes

Categories: all holes, amateur, anal, anal toying, big tits, blonde, british, crossdressing, cum, high heels

aShemaleTube

Asian CD Maid Dildo And Cum

Categories: amateur, asian, crossdressing, cum, dildo, homevideo, maid, masturbation, solo, stockings

aShemaleTube

MASTER SERGEANT Puts Faggyboi in Chastity

Categories: big black cock, blowjob, crossdressing, ebony, femboy, hd, lingerie, master, tranny

KeekAss

Transgender Princess Ginormous Rubber Pop-Shot & Jism Have Fun With Condom Mittens

Categories: amateur, babe, big cock, brunette, condom, crossdressing, cum, cumshot, fetish, fishnet

KeekAss

Random strangers manhandle my asspussy

Categories: amateur, anal, ass, bdsm, blonde, bound, crossdressing, femboy, fucking machine, hardcore

TrannyOne

Trans Wonder Woman ass fucks with sex machine and pumps the dong

Categories: anal, anal fisting, anal toying, ass, assfucking, big cock, crossdressing, femboy, fucking machine, gaping hole

KeekAss

t-girl niclo enjoy onanism on the couch

Categories: amateur, asian, blonde, couch, crossdressing, hd, lingerie, masturbation, mature, stockings

aShemaleTube

Asian sissy cum a lot after daddy masturbating her girl cock

Categories: amateur, asian, crossdressing, cum, cumshot, daddies, dick, femboy, futanari, hd

KeekAss

Super-steamy cascade young femboy brings himself to climax with a butt-plug in his caboose

Categories: amateur, anal, beauty, big ass, buttplug, cowgirl, creampie, crossdressing, cumshot, cute