Crossdressing Shemale Videos » 21

KeekAss

Plumbing Stunning Latin Crossdresser Luna Sol Sideways

Categories: amateur, anal, ass, beauty, blonde, crossdressing, cum, femboy, hd, homevideo

aShemaleTube

Riding crop for a slut ass

Categories: ass, crop whip, crossdressing, domination, hd, punishment, riding, slut

KeekAss

super-sexy gams in fishnets (two)

Categories: amateur, big ass, crossdressing, fetish, fishnet, hd, high heels, lingerie, mature, nipples

KeekAss

Super-Cute Twerk

Categories: amateur, big ass, blonde, crossdressing, cute, striptease, twerk

aShemaleTube

RedHeadMasterbation

Categories: amateur, crossdressing, hd, masturbation, mature, redhead

ShemaleMovie

Hd videos, ladyboy cum

Categories: babe, beauty, big cock, college, compilation, cosplay, crossdressing, cum, cum in mouth, cumshot

aShemaleTube

Ebony Hunk fucks Black Femboy Ezra_Kyle25 on Christmas

Categories: amateur, anal, big ass, big cock, black, blowjob, crossdressing, ebony, femboy, hd

xHamster

Red Party Time Dress

Categories: amateur, american, anal, ass, crossdressing, cute, dress, hd, lingerie, mature

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

XXXDan

Sissy Kuroko in Chinese dress with huge dildo

Categories: amateur, anal, big ass, chinese, cosplay, crossdressing, dildo, dress, gaping hole, hardcore

xHamster

Full Feminization and Tucking Teen Sissy Crossdresser

Categories: amateur, beauty, big cock, crossdressing, dick, feminization, fetish, hd, high heels, latex

KeekAss

Encaged PHAT ASS WHITE GIRL Sissy plays with pink hole!

Categories: amateur, anal, anal toying, ass, big ass, buttplug, cage, clit, crossdressing, cumshot

KeekAss

My hottest pal visited me in SP

Categories: amateur, anal, asian, beauty, best friend, big ass, big black cock, big cock, big tits, brazilian

KeekAss

Rubberdoll Monique - Ballet high-heeled shoes & stocking

Categories: amateur, ballerina, crossdressing, fetish, hd, pornstar, pov, stockings

Pornstars: Rubberdoll

HClips

Sex Show Gigi And Dave, Webcam Pov, Shemale And Man 2025-04-27

Categories: amateur, blonde, british, crossdressing, hd, high heels, milf, mom, nylon, pov

aShemaleTube

Masturbation and swallow...

Categories: amateur, crossdressing, cum in mouth, cum swallowing, cumshot, fetish, homevideo, masturbation, mature, solo

aShemaleTube

This is what you gonna see when I will suck your cock 😉 🍆 😯

Categories: amateur, blowjob, crossdressing, dick, femboy, handjob, hd, homevideo, pantyhose, pov

xHamster

Crossdressing Dildo Fun Outdoors

Categories: amateur, anal, anal toying, beauty, british, crossdressing, dildo, fetish, funny, hd

xHamster

Red Underwear Cum

Categories: amateur, boss, british, corset, crossdressing, cum, european, handjob, lingerie, mature

xHamster

Serge3dx Futa Ba3 Episode Tasty Intense Orgy Hot Tasty Whore Swallowing Cum Intense Pleasure Thirsty Buttocks Fucked Hard

Categories: amateur, american, asian, big cock, black, compilation, crossdressing, cum, cum swallowing, cumshot

JizzBunker

Crossdresser Sissybritneylane gags on many guys cocks, crossdresser

Categories: amateur, bdsm, big cock, blowjob, couple, crossdressing, dick, gagging, gay, lingerie

KeekAss

Pretty With Glasses

Categories: amateur, ass, beauty, brunette, crossdressing, cute, dress, ebony, femboy, glasses

KeekAss

SisK underwear bevy EP16.trio: Crossdresser fapping off with crimson lace mitten and jizm in rubber

Categories: big cock, condom, crossdressing, cum, cumshot, handjob, high heels, homevideo, jerking, lace

KeekAss

Morning Procedures - prepping for my tryst

Categories: amateur, crossdressing, high heels, lingerie, masturbation, mature, milf, nylon, outdoor, pissing

aShemaleTube

Mirjam and Mrs Samantha Hug, Suck and Spoon-fuck!

Categories: amateur, anal, blonde, blowjob, crossdressing, dutch, high heels, lingerie, mature, small tits

KeekAss

Streaming on Chaturbate @ Warlock_Dominatrix

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

KeekAss

Sissy in fishnet stocking two/two

Categories: amateur, anal, ass, crossdressing, dildo, dress, femboy, fishnet, hd, ladyboy

xHamster

Fuck Machine Fucks Sexy Crossdresser

Categories: amateur, american, anal, big ass, crossdressing, femboy, feminization, hd, lingerie, sissy

xHamster

Serge3dx Principal Lesson Episode Tasty Slut Thirsty Teacher Hot Cum Pleasure Tight Pussy Dripping Tasty Cum Intense

Categories: amateur, american, asian, big cock, compilation, crossdressing, cum, cumshot, hd, homevideo

xHamster

Pizza BOY Cummed in my Pantyhose

Categories: boy, cosplay, crossdressing, cum, german, hd, high heels, outdoor, pantyhose, public

JizzBunker

Sissy Mykella sucks, strokes and eats her own cum

Categories: amateur, bbw, beauty, blowjob, crossdressing, cumshot, cute, handjob, masturbation, own cum

aShemaleTube

Ass fingering and dildoing

Categories: assfingering, crossdressing, dildo, leggings, mature, rimjob

aShemaleTube

Alice Latexy blowjob training

Categories: amateur, blonde, blowjob, crossdressing, hd, homevideo, latex, mask, sissy, solo

KeekAss

Messy Sissy Plays In Brighter Pantyhose Supah Scorching With Her Cooch And Her Ginormous bud - kasia_cd

Categories: amateur, anal, anal toying, big clit, brunette, clit, crossdressing, cumshot, dirty, fetish

aShemaleTube

Indian Crossy Housewife strips and pees

Categories: amateur, crossdressing, desi, femboy, hd, housewife, indian, pissing, sissy, solo

xHamster

Hot Crossdressing Goddess Gets Blowjob From Trans Kelsey Masters - Compilation 1

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

xHamster

Nylon, Spit & Multiple Orgasm While Riding Dildo

Categories: big cock, crossdressing, cum, dick, dildo, feet, fetish, hd, lingerie, nylon

JizzBunker

Tgirl Riley TgirlTrainerNL date 1

Categories: amateur, anal, beauty, big cock, blowjob, crossdressing, gay, hardcore, lingerie, masturbation

aShemaleTube

Touch Me in Crotchless Panties

Categories: amateur, asian, crossdressing, hd, homevideo, lingerie, masturbation, panties, pov, sissy

aShemaleTube

a supers sexy day

Categories: amateur, anal, big ass, cage, crossdressing, femboy, hd, homevideo, masturbation, mature

aShemaleTube

Big Tits Big Dick Shemale

Categories: amateur, big cock, big tits, crossdressing, femboy, glasses, homevideo, masturbation, solo, teen (18+)

xHamster

Bound sissy slut - fuck her somebody

Categories: amateur, big tits, bondage, bound, crossdressing, european, german, hd, lingerie, sissy

KeekAss

ideal bouncy arse in pinkish underpants and then nude

Categories: amateur, ass, big ass, brunette, crossdressing, dancing, homevideo, ladyboy, nude, panties

KeekAss

Stellar Sophie in Spandex Sundress and Mittens Lures you and Faps her Gal Jizz-Shotgun

Categories: amateur, beauty, big tits, blonde, bodystocking, boots, crossdressing, fetish, handjob, jizz

aShemaleTube

Indian Sissy maid Payal cums in own asshole

Categories: amateur, anal, ass, crossdressing, cum, cumshot, femboy, hd, indian, maid

KeekAss

Streaming on Chaturbate @ gurlzdotco

Categories: amateur, anal, big cock, blonde, crossdressing, feminization, gay, hd, lingerie, masturbation

xHamster

Fisting ass sissy travesti

Categories: amateur, ass, boy, crossdressing, dildo, extreme, femboy, fisting, gaping hole, gay

KeekAss

Uber-cute transgender princess toying in fresh mini-skirt

Categories: amateur, big cock, creampie, crossdressing, cute, femboy, hd, lesbian, miniskirt, sissy

aShemaleTube

Indian Crossdresser Playing with her Sissy Clit Cock

Categories: clit, crossdressing, dick, hd, indian, sissy

XXXDan

Sexy redhead crossdresser fucked in the ass by a doctor

Categories: amateur, anal, ass, big ass, blowjob, crossdressing, doctor, gangbang, hardcore, lingerie

aShemaleTube

no 215 suleika rubber bangs xhamster user maggie er bij

Categories: crossdressing, hd, rubber

KeekAss

Whooty vibrating at home. Phat Ass White Girl dirty dances and dances. CD trans having joy.

Categories: amateur, anal, ass, babe, big ass, crossdressing, dirty, feet, fishnet, hd

aShemaleTube

Trampling on high heeled boots

Categories: bdsm, boots, crossdressing, domination, fetish, hd, slave, trampling

KeekAss

Skitty in Gentle spanking into Rock-Hard Sissygasm

Categories: amateur, anal, anal toying, crossdressing, cumshot, dildo, fetish, fisting, latex, masturbation

aShemaleTube

Did anal play in a Nazrin cosplay and came on my soles.

Categories: amateur, anal, cosplay, crossdressing, cumshot, dildo, hd, homevideo, japanese, ladyboy

xHamster

Ladyboy jerks off huge cock in tights and makes a cumshot without hands

Categories: asian, big cock, crossdressing, cum, cumshot, handjob, hd, huge cock, joi, ladyboy

xHamster

With my creamy dildo

Categories: anal toying, big ass, compilation, creampie, crossdressing, cum, cum in mouth, cumshot, dildo, hardcore

aShemaleTube

crossdress VID_20240923_233214

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

JizzBunker

Crossdresser with female mask sandy-deluxe fucked

Categories: anal, crossdressing, fetish, hardcore, mask

XXXDan

Good anal pounding with a fucking machine

Categories: amateur, anal, beauty, big ass, crossdressing, dildo, french, fucking machine, hardcore, masturbation

TrannyOne

crossdresser wanking in red dress

Categories: amateur, bed sex, big cock, crossdressing, cum, cumshot, dress, feet, fetish, handjob

JizzBunker

Outdoor fun

Categories: amateur, anal, crossdressing, dildo, funny, hardcore, lingerie, masturbation, outdoor, polish

aShemaleTube

Bottom Jen is Riding BBC Dildo and Milking herself

Categories: barebacking, big black cock, crossdressing, cumshot, dildo, fake tits, hd, homevideo, lingerie, masturbation

KeekAss

Sissy-Kuroko Humungous Anal Invasion Cork

Categories: amateur, anal, anal toying, asian, ass, buttplug, crossdressing, femboy, hd, homevideo

KeekAss

Sunny Day with TRANSSEXUAL Leela Wong

Categories: amateur, anal, beauty, cowgirl, crossdressing, cum, dick, dildo, hd, lingerie

Pornstars: Sunny Day

ShemaleMovie

Joselynne the crossdresser enjoys a hardcore anal session with her sex toys

Categories: amateur, anal, anal toying, ass, big ass, crossdressing, dildo, hardcore, high heels, lingerie

ShemaleMovie

Amateur femboy, underwear

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

xHamster

This Video Is Smokin Hot

Categories: amateur, anal, beauty, crossdressing, deep throat, dick, dildo, doll, hd, high heels

JizzBunker

Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in Locked up Again!

Categories: amateur, beauty, big cock, blonde, crossdressing, fetish, skinny, slut, small cock, solo

aShemaleTube

Mature crossdresser secretary with a skirt bulge

Categories: amateur, crossdressing, hd, lingerie, mature, model, secretary, sissy, skirt, solo

JizzBunker

Lililaura, submissive crossdresser, takes a sexy walk to attract clients

Categories: amateur, anal, bdsm, big cock, blowjob, couple, crossdressing, hardcore, nude, outdoor

aShemaleTube

I want a Gangbang!!

Categories: amateur, big cock, crossdressing, dirty talk, gangbang, hd, lingerie, stockings

xHamster

Marilyn Eats An Apple Trans Temptation Food Play Goddess

Categories: amateur, american, beauty, big tits, blonde, crossdressing, fetish, food, goddess, hd

aShemaleTube

Bdsm crossdresser dominatrix

Categories: bdsm, crossdressing, domination, dominatrix, slave

aShemaleTube

My new monster toy almost didn´t fit

Categories: amateur, crossdressing, cumshot, dildo, fetish, german, hd, huge dildo, lingerie, masturbation

ShemaleZ

Crossdresser Crazy Handcuffed

Categories: amateur, bdsm, crazy, crossdressing, handcuffed, hd, redhead, solo, stockings

aShemaleTube

Trixy Is Home Alone Doing Whatever She Wants in the Kitchen

Categories: amateur, anal, beauty, blonde, blowjob, crossdressing, cum, cumshot, hd, high heels

ShemaleMovie

Disrobing from my lacy white panties and stockings

Categories: big cock, blonde, crossdressing, ladyboy, lingerie, masturbation, panties, small tits, stockings, white

aShemaleTube

Fit sissy with a big ass wrecking her hole

Categories: big ass, crossdressing, doggystyle, femboy, hd, sissy

xHamster

My ass wearing shorts and it was plug in

Categories: amateur, anal, ass, big ass, bikini, blonde, brazilian, buttplug, crossdressing, doll

aShemaleTube

cum in the forest

Categories: amateur, crossdressing, cum, forest, hd, outdoor, small tits, solo

XXXDan

Crossdressing couple spanking fun

Categories: amateur, anal, bdsm, couple, crossdressing, funny, gay, hardcore, lingerie, mature

xHamster

Asian Dildo Fuck

Categories: amateur, anal, anal toying, asian, bathroom, crossdressing, dildo, hd, masturbation, mature

xHamster

thrust power of dick Big cook Masturbation cumshot Big Daddy dick amateurBig dick masturbation long lasting squirti

Categories: amateur, anal, anime, asslick, barebacking, big cock, boy, bukkake, crossdressing, cum

aShemaleTube

Wild queens

Categories: crossdressing, lingerie, queen, transsexual, vintage, wild

KeekAss

Poundable Rump in a Crimson Micro-Skirt and Nylon Pantyhose

Categories: amateur, anal, ass, brunette, crossdressing, cum, cumshot, dildo, hd, high heels

aShemaleTube

Transgender Strip Pole Dancer cums on stage

Categories: amateur, crossdressing, cum, dancing, fetish, hd, homevideo, lingerie, mature, small tits

xHamster

WHITE LADYBOY SEXY HOT SHEMALE SISSY CROSSDRESSER FEMBOY

Categories: compilation, crossdressing, cum, cum in mouth, cumshot, dancing, femboy, hd, ladyboy, massage

xHamster

Big black dildo slipping out of my pussy

Categories: amateur, anal toying, black, crossdressing, cum, dildo, fetish, hd, high heels, ladyboy

xHamster

Note: Amane Misa Cosplay - Sweet Misa can play all by herself... Doesn't she deserve a reward? 💛

Categories: amateur, anal, asian, beauty, big ass, big cock, cosplay, creampie, crossdressing, femboy

aShemaleTube

crossdress VID_20240613_165746

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

aShemaleTube

Sexy Masturbation Femboy

Categories: amateur, crossdressing, cute, femboy, homevideo, kitchen, masturbation, oral, solo, teen (18+)

xHamster

Lacy-Rose wagging her tail

Categories: amateur, anal toying, ass, british, buttplug, crossdressing, hd, lingerie, pornstar, sissy

Pornstars: Lacy Rose

xHamster

Burning Passion: Fueling the Flames of Desire

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

KeekAss

T-Model Lashing Juice

Categories: amateur, bdsm, creampie, crossdressing, cumshot, cute, dick, femboy, fetish, fisting

KeekAss

Crossdresser Stroking and Spunking at Camper Park

Categories: amateur, blonde, crossdressing, cum, fetish, hd, jerking, latex, masturbation, mature

HClips

Crossdresser Anal Fisting Hands Free Cumming Many Times

Categories: amateur, anal fisting, brunette, crossdressing, cum, fisting, outdoor, stockings

aShemaleTube

My silk skirt simply presented as I like to wear it.

Categories: amateur, crossdressing, fetish, hd, skirt, solo, uniform

xHamster

Secretdreamsfuta Intense Hard Anal Sex with a Hot, Curvy Woman: Deep Fucking, Gaping Sweet Ass, Cum

Categories: anal, asian, ass, barebacking, bbw, big ass, big cock, big tits, creampie, crossdressing

xHamster

New Part Time Job

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

KeekAss

Insatiable femboy shoots a load in a vapid innocence cell and keeps railing

Categories: amateur, anal, cage, crossdressing, cum, cute, dildo, femboy, feminization, handjob

JizzBunker

Crossdresser fuck

Categories: crossdressing, gay, hardcore

aShemaleTube

Mature crossdresser holly smoking in pantyhose

Categories: amateur, crossdressing, hd, mature, model, pantyhose, smoking, tgirl, tranny, transsexual

aShemaleTube

Chubby guy eat CD's ass and cock

Categories: ass, blowjob, boots, chubby, crossdressing, dick, hd, high heels, homevideo, mature

xHamster

Ravishing Revelations: Unleashing My Inner Vixen

Categories: amateur, american, beauty, big ass, big tits, blonde, crossdressing, femdom, feminization, hd

KeekAss

Popping My Pooper

Categories: amateur, anal, ass, big cock, close up, crossdressing, extreme, fetish, gaping hole, handjob

KeekAss

Twunk sissy frolicking in the kitchen with a cucumber self facial cumshot

Categories: amateur, anal, assfucking, bikini, crossdressing, cucumber, cumshot, facial, hd, homevideo

Pornstars: Rose Marie

KeekAss

Femboy in white underwear screws silicone vagina

Categories: amateur, big ass, crossdressing, fake tits, femboy, hd, homevideo, lingerie, masturbation, sissy

aShemaleTube

Arab Sissy CD throating BBC in public park

Categories: arab, big black cock, blowjob, crossdressing, deep throat, hd, oral, park, public, sissy

xHamster

Crossdresser husband playing in stockings and heels. No cumming yet.

Categories: big tits, british, crossdressing, cum, hd, high heels, husband, lingerie, masturbation, mature

aShemaleTube

seamlessly: CD in pantyhose

Categories: crossdressing, homevideo, lingerie, pantyhose, solo, stockings

ShemaleMovie

German teenager Tight Tini gets pounded by crossdresser transsexual at user meetup

Categories: big cock, big tits, crossdressing, german, small cock, teen (18+), tight, transsexual

xHamster

Anal Pleasure for a CD Lady

Categories: amateur, anal, anal toying, crossdressing, cum, german, hd, high heels, lingerie, masturbation

HClips

Incredible Sex Clip Transsexual Stockings Private Exclusive Like In Your Dreams

Categories: amateur, crossdressing, fantasy, gay, solo, stockings, toys, transsexual

xHamster

Blonde Crossdresser get fucked by dildo

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

aShemaleTube

Kimi TV is Lewd Slut in Quiet Town

Categories: amateur, crossdressing, femboy, hd, lingerie, outdoor, sissy, slut, small cock, solo

aShemaleTube

Anal insertions

Categories: anal, ass, crossdressing, dildo, hd, insertion, mature, toys

KeekAss

All clothed in crimson and prepped to jizm sexp

Categories: amateur, brunette, clothed sex, crossdressing, cum, hd, lingerie, stockings, toys, webcam

xHamster

Trixy Love to Cumming! - Cumming Greatest Hits 2

Categories: anal, barebacking, bdsm, beauty, blowjob, bondage, crossdressing, cum, dick, femboy

ShemaleMovie

Double wedged doofy with Kapri Sun and Mistress Scarlet Kiss in thrilling sissy action

Categories: amateur, american, babe, bdsm, beauty, blonde, crossdressing, cum, dildo, high heels