Crossdressing Shemale Videos » 37

aShemaleTube

Slave licking thigh boots

Categories: boots, crossdressing, domination, fetish, hd, licking, mature, slave

aShemaleTube

Jenn Sucks a Cock While On Her Knees

Categories: amateur, blowjob, crossdressing, dick, hd, homevideo, knees, masturbation, solo, sucking

KeekAss

CROSSDRESSER TVROSE BLACK FISHNET BODYSTOCKING EDGING EJACULATION AND VIBING ASSFUCK BUTTPLUG

Categories: amateur, anal, assfucking, black, bodystocking, buttplug, crossdressing, cumshot, dick, edging

KeekAss

Videoclip music by PinkKissy

Categories: amateur, anal, crossdressing, fetish, handjob, hd, ladyboy, lingerie, music, stockings

TrannyOne

Young Slut Cums With Huge Vibrating Dildo In The Ass

Categories: amateur, anal, anus, ass, crossdressing, cum, cumshot, dildo, gay, hd

aShemaleTube

Turkish CrossDresser Buse Naz Arican Slaves Koleler 1

Categories: compilation, crossdressing, slave, turkish

xHamster

Femboy Pegged

Categories: amateur, american, anal, beauty, blowjob, crossdressing, cum, domination, femboy, feminization

aShemaleTube

crossdress VID_20240927_225524

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

ShemaleMovie

Shemale femboy, amateur femboy

Categories: amateur, anal, anal toying, ass, beauty, big ass, crossdressing, femboy, fishnet, gaping hole

xHamster

Patty crossdresser trying a new dildo machine in secretary style

Categories: amateur, anal, crossdressing, dildo, european, french, fucking machine, hd, high heels, lingerie

aShemaleTube

sissy slut walk

Categories: amateur, chinese, crossdressing, hd, ladyboy, lingerie, masturbation, outdoor, sissy, slut

aShemaleTube

First Time Straight Mexican Pounds Blonde Sissy

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

xHamster

I want to model lingerie in a hotel room for u!

Categories: amateur, american, bbw, beauty, crossdressing, hd, hotel, lingerie, masturbation, mature

TrannyOne

SENSUAL

Categories: american, anal, anus, ass, couple, crossdressing, erotic, gay, hd, sensual

aShemaleTube

Mature crossdressers and old men with younger females

Categories: amateur, blowjob, crossdressing, homevideo, mature, old farts, stockings

aShemaleTube

FaRee's #100th Bang-Bang with Secret BF R@@zZ!!!

Categories: amateur, anal, bangladeshi, boyfriend, crossdressing, desi, hd, hijab, homevideo, sissy

xHamster

misr4 - Fleshlight double cumshot

Categories: blowjob, crossdressing, cum, cumshot, dick, dress, fleshlight, handjob, hd, ladyboy

KeekAss

Sissy in Wonder Gal's costume packing her butt hole with trio bottles of beer at once by the door

Categories: amateur, anal, ass, blonde, costume, crossdressing, enema, exhibitionist, extreme, halloween

xHamster

Fishnet Pai-chan's Outdoor Joy

Categories: amateur, asian, crossdressing, cum, fishnet, hd, japanese, masturbation, mature, outdoor

aShemaleTube

MAID IN STOCKINGS

Categories: crossdressing, hd, maid, solo, stockings

xHamster

Sissy Slut Ejaculates After Morning Wakeup Cum Show at Country House

Categories: amateur, beauty, country, crossdressing, cum, cumshot, feminization, hd, homevideo, lingerie

KeekAss

A Worshipper Sent Her A Fresh Plaything And It Made Her Climax Stiff

Categories: amateur, anal, assfucking, cage, crossdressing, cum, cumshot, hd, ladyboy, lingerie

KeekAss

Nip have fun

Categories: amateur, bdsm, crossdressing, domination, fetish, funny, handjob, hd, high heels, latex

KeekAss

Chinese Crossdresser costume play Onanism 20151106 sample

Categories: amateur, anal, asian, big ass, chinese, costume, crossdressing, japanese, ladyboy, masturbation

HDSex

Sexy crossdresser Rachelle59 rocks lingerie, heels, and a sissy dress

Categories: amateur, beauty, crossdressing, dress, high heels, ladyboy, lingerie, sissy, stockings

aShemaleTube

Bunny Fantasy

Categories: amateur, big ass, blonde, bunny, crossdressing, fantasy, femboy, fetish, hd, ladyboy

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

webcams crossdress SVID_20240613_170347_1

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

XXXDan

The biggest cock I can stand so far

Categories: amateur, anal, big ass, big cock, crossdressing, cumshot, dick, dildo, hardcore, huge dildo

xHamster

Leatransteen Masturbating as Sissy Bride

Categories: amateur, bride, crossdressing, cum, lingerie, masturbation, satin, sissy, solo, stockings

KeekAss

Overflowing lace and lust in a voluptuous and addictive assets.

Categories: amateur, beauty, brunette, crossdressing, cute, daddies, doll, femboy, hd, lace

xHamster

Piss drinking slut

Categories: amateur, anal, big ass, big cock, crossdressing, danish, dick, fetish, hd, latex

KeekAss

Cute orange sundress, uber-cute undergarments - lots of joy!

Categories: amateur, big cock, big tits, clit, crossdressing, cute, dick, dress, glasses, huge cock

TrannyOne

Two queens introduce you to gay pride

Categories: bdsm, big tits, bisexual, crossdressing, domination, femdom, gay, humiliation, jerking, joi

aShemaleTube

Purple Corset Wetlook Stockings (enhanced)

Categories: amateur, corset, crossdressing, hd, homevideo, latina, lingerie, sissy, stockings

xHamster

I want to CUM when i get fucked in the ass..

Categories: amateur, anal, anal toying, ass, crossdressing, cum, dildo, femboy, greek, hd

aShemaleTube

Crossdresser cums while smoking

Categories: amateur, crossdressing, cum, cumshot, hd, homevideo, masturbation, mature, model, smoking

xHamster

Forged3dx Tasty Hot Big Ass Thirsty for Pleasure Hard Sex Hot Big Ass Fucked Intense Sex Tasty

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

xHamster

Crossdresser hellpunk_meow Masturbating in red boots

Categories: amateur, asian, big cock, boots, crossdressing, fetish, hd, ladyboy, masturbation, sissy

aShemaleTube

Gay sissies

Categories: ass, big cock, crossdressing, gay, nude, sissy

KeekAss

Chinese Crossdressers four

Categories: 3some, amateur, anal, blowjob, brunette, chinese, crossdressing, handjob, hd, japanese

ShemaleMovie

Dulce Lunita's trio of fun with big booty and toys!

Categories: ass, big ass, booty, crossdressing, funny, ladyboy, pantyhose, small tits, toys, uniform

aShemaleTube

sissy paul chronic masturbator

Categories: amateur, crossdressing, hd, masturbation, sissy, solo

KeekAss

She-creature , anal invasion , gimp costume ,

Categories: amateur, anal, bondage, costume, crossdressing, hd, ladyboy, legs, pantyhose

aShemaleTube

Piss time for latex mature CD

Categories: crossdressing, hd, homevideo, latex, mature, piss drinking, pissing

aShemaleTube

Sissy Uncut Cock Foreskin Closeup Fetish with Huge Cumshot

Categories: big cock, close up, crossdressing, cumshot, dick, femboy, fetish, hd, homevideo, ladyboy

Pornstars: Viper

xHamster

Black femboy Big ass and big dick with dildo and cum

Categories: amateur, anal, ass, big ass, big black cock, big cock, black, crossdressing, cum, dildo

xHamster

Crossdresser Thai dress

Categories: asian, crossdressing, cumshot, dress, hd, masturbation, thai

KeekAss

Cum Shot gothic fashion

Categories: amateur, big cock, crossdressing, cum, cumshot, curvy, cute, dick, german, goth

aShemaleTube

Pantyluvn sissy she’s so high

Categories: amateur, chubby, crossdressing, cumshot, dress, hd, homevideo, lingerie, masturbation, mature

TrannyOne

TV GIRLFRIEND (UK 1990) part 1

Categories: british, classic, crossdressing, english, european, gay, girlfriend, hd, transvestite, uk

KeekAss

Charli Santa Masturbate

Categories: amateur, crossdressing, cumshot, cute, handjob, masturbation, mature, santa, small cock, stockings

xHamster

Midnight ladyboy Serge Lusin. 2025cg

Categories: amateur, american, big ass, chubby, crossdressing, european, gay, hd, ladyboy, mature

xHamster

my sissy pussy likes to eat eggplant

Categories: amateur, anal, ass, beauty, crossdressing, femboy, feminization, hd, homevideo, ladyboy

aShemaleTube

Being a good sissy (click full screen)

Categories: belgian, crossdressing, cumshot, fetish, lingerie, masturbation, mature, sissy, stockings, toys

VideoSection

Shemale fuck shemale, shemale lingerie

Categories: amateur, beauty, big cock, crossdressing, cum, high heels, hotel, jizz, ladyboy, lingerie

aShemaleTube

Sweet femboy JOI & Cum instructions

Categories: amateur, big ass, blonde, crossdressing, cum, cumshot, femboy, hd, homevideo, joi

Pornstars: Viper

TrannyOne

Vintage crossdresser Karen Dior just loves to be roughly drilled

Categories: crossdressing, drilling, retro, vintage

aShemaleTube

sexy Tgirl Payal strips from sari and cums

Categories: amateur, anal, crossdressing, cum, cumshot, femboy, hd, indian, lingerie, masturbation

ShemaleMovie

Hd videos, crossdresser dildo

Categories: amateur, anal, anal toying, crossdressing, dildo, feet, hd, high heels, masturbation, queen

aShemaleTube

HA64Being stuffed with a remote-controlled anal plug in the library and enduring an orgasm!

Categories: anal, asian, big ass, chinese, crossdressing, cumshot, flashing, hd, librarian, masturbation

KeekAss

Streaming on Chaturbate @ Warlock_Dominatrix33

Categories: amateur, anal, big cock, blonde, close up, crossdressing, feminization, gay, hardcore, hd

aShemaleTube

cummin without you

Categories: black, blonde, crossdressing, cum, dress, hd, masturbation, solo, stockings, wife

xHamster

misr4 - cumshot on stockings

Categories: amateur, crossdressing, cumshot, fetish, hd, masturbation, mature, polish, sissy, small tits

KeekAss

Juggsy Damsel Masker Z Bowl Stripper #trio

Categories: amateur, big ass, big tits, blonde, club, compilation, crossdressing, dildo, feminization, fetish

aShemaleTube

Swinging again

Categories: amateur, blonde, crossdressing, hd, swinger

TrannyOne

Flat chested shemale wanks her fat dick on webcam solo

Categories: ass, babe, crossdressing, cum, dick, fat, flat chested, huge cock, jerking, ladyboy

aShemaleTube

Riding

Categories: crossdressing, hd, riding

xHamster

Crossdresser penelopene fuck hardcore XXL dildo

Categories: anal, bdsm, crossdressing, dildo, hardcore, hd, ladyboy, sissy, slave, spanish

KeekAss

Banging the Nasty Crossdresser Without a condom - Onlyfans Veronica Sanders

Categories: amateur, anal, banging, big black cock, black, blowjob, condom, couple, crossdressing, cute

aShemaleTube

Ass licking slut

Categories: amateur, ass, asslick, boots, crossdressing, hd, mature, pantyhose, rimjob, slut

TrannyOne

MILF domme anal fists tgirl

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

TrannyOne

Ugly crossdressing cock suckers are eager to drill each other

Categories: anal, ass, british, crossdressing, dick, facial, gaping hole, juicy, redhead, sucking

xHamster

Indian Crossdresser Shemale Rina Har Fuck Deep

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

ShemaleMovie

Gets, shemale anal dildo

Categories: amateur, anal, anal toying, ass, crossdressing, dildo, femboy, gaping hole, homevideo, huge dildo

aShemaleTube

Mature Asian sissy in white lingerie rides massive 11-inch BWC dildo

Categories: amateur, anal, asian, crossdressing, dildo, femboy, hd, lingerie, mature, sissy

XXXDan

High heels shemale in lingerie anal masturbation

Categories: anal, big ass, big cock, crossdressing, cumshot, double penetration, feet, gaping hole, gay, hardcore

XXXDan

Jorden Crossdresser Dominated by BBC bareback

Categories: barebacking, bdsm, big black cock, big cock, black, crossdressing, gay

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

KeekAss

Raw my denim brief, fap and spunk

Categories: amateur, crossdressing, cum, cumshot, fetish, handjob, hd, jeans, masturbation

XXXDan

Sexy Crossdresser kellycd2022 in backless leopard print dress and heels in the garden

Categories: amateur, big tits, british, crossdressing, dress, fetish, garden, high heels, masturbation, mature

xHamster

Cam4 - 5 Dress Open_ass Nylon_stockings Sissi Cumshot

Categories: ass, bdsm, big cock, bitch, crossdressing, cum, cumshot, dress, french, hd

aShemaleTube

Cosplay crossdresser play a dildo

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

JizzBunker

SLOPPY TRHOAT DOLL

Categories: amateur, blonde, blowjob, crossdressing, cute, dildo, doll, fishnet, gagging, hardcore

xHamster

Ms300 Sarazia Exotic - Slut Day Act 4

Categories: amateur, american, beauty, big ass, big cock, creampie, crossdressing, cum, cumshot, exotic

xHamster

Milf crossdresser soap opera

Categories: anal, big ass, creampie, crossdressing, cumshot, fetish, hd, latina, masturbation, mature

XXXDan

Playing with my little clit

Categories: amateur, big cock, clit, crossdressing, european, lingerie, masturbation, mature, panties, pantyhose

xHamster

DeeDeeSlut69 in Pink Dress Sucking on a Thick Dildo

Categories: amateur, american, bra, crossdressing, cum, dildo, dress, ladyboy, lingerie, sissy

aShemaleTube

Sissy crossdresser first time hands free cum sissygasm

Categories: crossdressing, cum, femboy, first time, game, hd, sissy

TrannyOne

Redhead shemale goes down on her knees to blow BBC

Categories: big black cock, blowjob, crossdressing, facial, knees, redhead, sucking, throat, tranny, transvestite

VideoSection

Horny transgirl Jessica Bloom teases her huge cock and enjoys her own creamy release

Categories: amateur, babe, beauty, big cock, blonde, creampie, crossdressing, cum, cumshot, edging

xHamster

Feet Cum on the Mirror.

Categories: amateur, big cock, compilation, crossdressing, cum, feet, fetish, hd, ladyboy, latina

xHamster

Sissy Destroys Her Pussy 5

Categories: anal, ass to mouth, crossdressing, dildo, hd, latina, lingerie, masturbation, pussy, sissy

KeekAss

attempting on cock-squeezing mini sundress

Categories: amateur, crossdressing, dick, dress, handjob, hd, solo, tranny

XXXDan

Trans Femdom Feet JoI CEI Lick That Cum Off My Sweaty Heels Bitch - Jessica Bloom

Categories: amateur, bdsm, beauty, big cock, bitch, british, cei, crossdressing, cum, cumshot

aShemaleTube

Virtual sex Pov Simatra CD fuck BBC *6

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

xHamster

Sisk Plug Her Butt Wiht Wireless Vibrator

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

aShemaleTube

Smoke break with a slave

Categories: crossdressing, domination, fetish, mature, slave, smoking

TrannyOne

Pegging Femdom on Crossdresser Unknown

Categories: 3some, anal, anus, asian, ass, bdsm, brunette, crossdressing, dark hair, domination

TrannyOne

Sissy GF Loves To Cum

Categories: amateur, asian, compilation, crossdressing, cum, cumshot, dick, girlfriend, japanese, ladyboy

ShemaleMovie

fellow barebacks CD bi-atch

Categories: barebacking, bisexual, crossdressing

ShemaleMovie

German, shemale outdoors public

Categories: amateur, crossdressing, cum, cumshot, german, high heels, jizz, lingerie, masturbation, nylon

KeekAss

Shemale Barebacked Anal Sex

Categories: amateur, anal, barebacking, beauty, black, chubby, crossdressing, cute, homevideo, japanese

JizzBunker

Shemale getting ready for another hotel FAN-FUCK

Categories: amateur, anal, beauty, big ass, big cock, big tits, blonde, couple, crossdressing, cumshot

xHamster

Fishnet Pantyhose, Cumshot on Heels and Walking in These Heels

Categories: amateur, beauty, big cock, crossdressing, cum, cumshot, fishnet, hd, high heels, lingerie

KeekAss

Pretty Face Tranny Babe Masterbates On Webcam

Categories: amateur, anal, ass, babe, beauty, crossdressing, cute, femboy, hd, homevideo

KeekAss

Sissy V-Card Striptease Image Shoot in the Park

Categories: amateur, cage, crossdressing, fetish, ladyboy, mature, outdoor, park, photoshoot, pov

TrannyOne

Crossdressers Clip

Categories: bdsm, compilation, crossdressing, feminization, transvestite

TrannyOne

Raunchy tranny butts get drilled hard in a retro orgy

Categories: ass, crossdressing, drilling, girlfriend, ladyboy, orgy, pretty, raunchy, retro, tgirl

aShemaleTube

this sexy tranny swallows my big cock completely every time

Categories: barebacking, big cock, blonde, blowjob, crossdressing, cum in mouth, cum swallowing, cumshot, hd, ladyboy

aShemaleTube

Sissy unlocks her chastity device for much-needed cum eating reward

Categories: crossdressing, cum, cumshot, dildo, femboy, masturbation, sissy

JizzBunker

Blonde Bombshell Chronicles: Unveiling the Mesmerizing Aura and Irresistible Charisma

Categories: 3some, amateur, bdsm, beauty, big ass, big cock, big tits, blonde, bombshell, cosplay

aShemaleTube

Sissy crossdresser nurse with tentacle dildo

Categories: amateur, anal, big tits, crossdressing, dildo, hd, lingerie, mature, nurse, sissy

xHamster

Set to Clear Your Heart

Categories: amateur, asian, bbw, beauty, crossdressing, hd, japanese, ladyboy, masturbation, outdoor

aShemaleTube

webcams crossdress SVID_20240218_030234_1

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

KeekAss

plumper transgirl gets married stud humid

Categories: amateur, anal, barebacking, big ass, blowjob, creampie, crossdressing, cumshot, hd, homevideo

KeekAss

I'm flashing my worshippers the strength of my XXL transgirl meatpipe

Categories: amateur, big cock, crossdressing, cumshot, dick, flashing, handjob, hd, huge cock, joi

HClips

Transsexual Bang A Large Pig

Categories: 3some, amateur, bdsm, brunette, crossdressing, gay, transsexual, webcam

aShemaleTube

sissyTee

Categories: amateur, anal, ass, big black cock, big cock, black, booty, crossdressing, cumshot, ebony

JizzBunker

Big Cock Sissy Crossdressor Huge Cumshot

Categories: amateur, asian, beauty, big cock, crossdressing, cumshot, japanese, korean, masturbation, sissy