Crossdressing Shemale Videos » 31

KeekAss

Draining in Silk Pj's and Nylon Tights

Categories: amateur, big cock, crossdressing, cumshot, fetish, hd, lingerie, masturbation, mature, milf

KeekAss

All clothed in crimson and prepped to jizm sexp

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

KeekAss

SQUID GAME ANAL INVASION PARODY

Categories: amateur, anal, crossdressing, game, hd, latina, parody, perfect body, solo, tranny

aShemaleTube

Helga Wanking & Cumming In High Heels - [2025-07-22]

Categories: amateur, big cock, blonde, crossdressing, cum, cumshot, femboy, hd, high heels, homevideo

ShemaleMovie

Crossdresser anal, ladyboy ass

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

KeekAss

Solo Trap Babe Dildoing Her Tight Butthole

Categories: amateur, anal, ass, babe, beauty, big cock, crossdressing, dildo, femboy, futanari

aShemaleTube

crossdress VID_20231129_014357

Categories: asian, chinese, crossdressing, hd, homevideo, lingerie, masturbation, pantyhose, stockings

KeekAss

TRANS CATGIRL GETS PORKED IN THE CABOOSE BY JASON DRAKE

Categories: amateur, anal, blowjob, brunette, cosplay, crossdressing, emo, fetish, hd, small tits

KeekAss

Sissy having joy before bedtime

Categories: amateur, anal, ass, bed sex, blowjob, brunette, clothed sex, crossdressing, cum, dildo

TrannyOne

crossdresser humiliation and anal fuck

Categories: amateur, anal, anus, ass, assfucking, bdsm, blowjob, booty, crossdressing, domination

ShemaleMovie

Gorgeous crossdressing cutie Xdresserwithass home alone with a huge dildo

Categories: amateur, anal, beauty, booty, crossdressing, cute, dildo, femboy, gorgeous, homevideo

aShemaleTube

In my black short shorts

Categories: black, crossdressing, shorts

ShemaleMovie

Sensational photoshoot with sissy Bailey Wilde heats up the screen

Categories: amateur, american, anal, bdsm, bondage, crossdressing, cum, domination, femboy, jizz

aShemaleTube

Exposed Sissy Bitch Tiffany Minx – Expose Yourself 2

Categories: bitch, crossdressing, exhibitionist, femboy, fetish, hd, pornstar, sissy, small cock, stockings

Pornstars: Tiffany Mynx

aShemaleTube

Barbie minidress Public Slutwalk

Categories: amateur, big ass, crossdressing, domination, dress, femboy, hd, homevideo, ladyboy, lingerie

KeekAss

Full Salute in Grey lace nickers femboy crossdresser draining to Cuck being abjected

Categories: amateur, beauty, big cock, crossdressing, cute, femboy, handjob, hd, homevideo, lace

TrannyOne

Surprise Guest Girl Has Dick!

Categories: 18 year old, anal, anus, ass, assfucking, crossdressing, dick, extreme, hardcore, innocent

aShemaleTube

My asian sissyboy loves dick

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

aShemaleTube

Crazy 60 multiple sissy femboy Viper Fierce creampies and huge cumshots

Categories: anal, asian, barebacking, blowjob, compilation, crazy, creampie, crossdressing, cumshot, femboy

Pornstars: Viper

ShemaleMovie

Amateur transgender in pantyhose gets drilled in HD videos

Categories: amateur, anal, big cock, crossdressing, dildo, drilling, german, hd, lingerie, pantyhose

ShemaleMovie

Nun with a surprise rides big dildo and drains it dry

Categories: amateur, anal, ass, big ass, blowjob, cosplay, crossdressing, cum, cumshot, dildo

aShemaleTube

Black crossdresser webcam show

Categories: black, crossdressing, solo, spit, transsexual, webcam

KeekAss

Play And Solo Masturbation

Categories: amateur, beauty, brunette, crossdressing, dick, futanari, homevideo, jerking, lingerie, masturbation

KeekAss

Taunting whilst experiencing servant and adoring alpha wood

Categories: amateur, beauty, big cock, crossdressing, dick, femboy, handjob, hd, homevideo, lingerie

KeekAss

CD Selenas ass fucking Boning Marathon Pinch 197

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

KeekAss

This Gurl Belongs on Her Knees Facehole Open Pt two

Categories: amateur, blowjob, brunette, crossdressing, deep throat, hd, homevideo, knees, lingerie, mature

aShemaleTube

Fluttering fun with my satin nightdress.

Categories: amateur, blonde, crossdressing, femboy, fetish, funny, hd, ladyboy, satin, solo

aShemaleTube

Ready for the gym

Categories: crossdressing, gym, hd, mature, model, stockings, transsexual

KeekAss

Emo Trans female has solo joy in Hip High Shoes

Categories: american, anal, anal toying, ass, bdsm, beauty, bondage, crossdressing, emo, fat

aShemaleTube

crossdress VID_20231205_042348

Categories: asian, chinese, crossdressing, hd, homevideo, lingerie, masturbation, pantyhose, stockings

KeekAss

Mitts Free-For-All Buttfuck Ejaculation Sissygasm Compilation six

Categories: amateur, anal, anal toying, assfucking, cage, compilation, crossdressing, cum, cumshot, dildo

aShemaleTube

Fat bastard cum on feet and lick them

Categories: 4some, crossdressing, cum, cumshot, daddies, domination, fat, feet, granny, licking

ShemaleZ

Cd In Lingerie Edging

Categories: amateur, blonde, crossdressing, edging, lingerie, solo, stockings, webcam

TrannyOne

(3dxChat) BDSM room

Categories: 3d, animation, anime, bdsm, bondage, crossdressing, domination, fetish, game, hd

aShemaleTube

Auntie Holly riding a dildo in chastity

Categories: anal, crossdressing, dildo, hd, mature, riding, stockings

aShemaleTube

Seducing Nylon Stockings and Pantyhose Sissy Femboy Foot Fetish

Categories: asian, crossdressing, feet, femboy, fetish, hd, homevideo, lingerie, nylon, pantyhose

Pornstars: Viper

aShemaleTube

Blowjob Cum Swinger Club Barcelona BarbaraCD

Categories: amateur, blowjob, club, crossdressing, cum, cumshot, hd, lingerie, stockings, swinger

ShemaleMovie

Amateur sissy shemale enjoys outdoor anal play with toys and cums hard

Categories: amateur, anal, anal toying, beauty, crossdressing, cum, cumshot, european, jizz, ladyboy

aShemaleTube

Tvkina mr pinky can’t go deeper

Categories: anal, anal toying, crossdressing, dildo, fishnet, smoking, solo, stockings, wet

aShemaleTube

Two slaves drink crossdresser's piss

Categories: crossdressing, domination, hd, mature, piss drinking, pissing, slave

KeekAss

cum-shot of a bangable COUGAR in antique undergarments

Categories: amateur, anal, anal toying, brunette, cougar, crossdressing, cumshot, hd, high heels, lingerie

KeekAss

Selfbondage plowed by machine gone wrong

Categories: amateur, bdsm, bondage, corset, crossdressing, dildo, fetish, fucking machine, hd, high heels

aShemaleTube

CdTina cock slapped and gagging

Categories: amateur, big cock, crossdressing, dick, fetish, gagging, hd, homevideo, interracial, long nails

KeekAss

Window demonstrate

Categories: amateur, ass, brunette, crossdressing, hd, homevideo, lingerie, pantyhose, sissy, small tits

aShemaleTube

homemade toys

Categories: crossdressing, hd, homevideo, mature, toys

aShemaleTube

(1) Pink Maid Takes A Break While Her Employer Is Away. Cage & Plug. Cam4 Vanessabarbie Vanessabitch

Categories: amateur, cage, crossdressing, doll, european, fishnet, french, hd, high heels, maid

HDSex

Dive into the juicy bussy of a Chinese femboy Part 1

Categories: anal, big cock, chinese, compilation, crossdressing, cumshot, femboy, juicy

ShemaleMovie

Sissy crossdresser in anal play with sex toy

Categories: anal, anal toying, crossdressing, dildo, fishnet, gaping hole, masturbation, sissy, toys

KeekAss

Pink Pumped

Categories: amateur, anal, big ass, buttplug, crossdressing, cum, cumshot, dildo, fetish, gloves

KeekAss

Licking feet outdoor

Categories: amateur, crossdressing, domination, feet, fetish, hd, humiliation, latex, licking, mature

aShemaleTube

red lipstick smoking close up

Categories: amateur, blonde, close up, crossdressing, hd, lipstick, smoking

aShemaleTube

Sissy Lucy spitroast in chastity by double fucking machines

Categories: amateur, big tits, cage, crossdressing, fucking machine, hd, homevideo, mature, model, redhead

ShemaleZ

Cross Dressing Whore Very Hard Fucking Her Mistress

Categories: amateur, brunette, crossdressing, hardcore, hd, lingerie, mistress, slut, stockings, tattoo

JizzBunker

Swimsuit, pee, dildo and a huge load

Categories: amateur, anal, big cock, bikini, crossdressing, cumshot, dildo, european, hardcore, pissing

aShemaleTube

Zentai Spandex Suit Sissy Fucking Her New Ass Toy

Categories: asian, ass, creampie, crossdressing, cumshot, femboy, hd, homevideo, masturbation, model

Pornstars: Viper

ShemaleMovie

Lovely ladyboy strokes her big cock without hands in a steamy pre-cumming scene

Categories: amateur, american, bdsm, beauty, big cock, college, compilation, cosplay, crossdressing, cum

KeekAss

Sissy Breezy Lola gets handcuffed and pounded by BIG BLACK COCK

Categories: amateur, anal, ass, assfucking, bdsm, big black cock, big cock, blonde, crossdressing, femboy

KeekAss

Bone oral job Chinese Crossdresser Costume Play

Categories: amateur, anal, asian, blonde, blowjob, chinese, cosplay, costume, crossdressing, femboy

aShemaleTube

Master Fuck Zofe Susi

Categories: amateur, crossdressing, domination, master

TrannyOne

slap bitch bdsm

Categories: amateur, anal, ass, bdsm, big tits, bitch, crossdressing, fetish, latex, mature

TrannyOne

submissive crossdresser maid gets fucked in her ass

Categories: anal, ass, bdsm, blowjob, crossdressing, maid, oral, submissive, transvestite, uniform

ShemaleZ

Sexy Crossdresser In Golden Heels Takes Dildo

Categories: amateur, big ass, crossdressing, dildo, hd, high heels, lingerie, milf, solo, toys

aShemaleTube

Slut Sissy Samana (CB:showlover12) edging and cumming

Categories: crossdressing, cum, cumshot, edging, hd, homevideo, lingerie, masturbation, pantyhose, sissy

ShemaleMovie

Attractive transgender babe in lingerie gets naughty with anal toys

Categories: anal, anal toying, babe, beauty, blonde, braces, crossdressing, dildo, ladyboy, lingerie

ShemaleMovie

Gorgeous crossdresser gives shemale handjob and gets pounded

Categories: amateur, anal, asian, blowjob, cosplay, creampie, crossdressing, femboy, gorgeous, handjob

KeekAss

Alyssa maid demonstrates off her fucktoy!

Categories: amateur, anal, assfucking, blowjob, cosplay, crossdressing, doggystyle, hd, lingerie, maid

aShemaleTube

Pissing in slut ass and fuck her

Categories: anal, ass, crossdressing, dirty, fetish, pissing, slut, speculum

KeekAss

Gargle instructing with a dual finished fake penis. With Essex Dame Lisa and TGirl April

Categories: amateur, big cock, blonde, blowjob, british, brunette, crossdressing, dick, dildo, gagging

aShemaleTube

Sissy Lucy pegged by huge black mamba dildo and covered in fake cum bukkake

Categories: amateur, big tits, black, bukkake, clothed sex, crossdressing, cum, cumshot, dildo, domination

ShemaleZ

Crossdresser in Red Corset is Riding on Monster Dildo

Categories: corset, crossdressing, dildo, lingerie, riding, solo, toys

aShemaleTube

Cute Goth CD Shoots 1:56

Categories: amateur, asian, chinese, crossdressing, cumshot, cute, femboy, goth, pantyhose, sissy

KeekAss

Queer crossdresser lovely twunk or style lady on runway?

Categories: amateur, crossdressing, fetish, gay, hd, high heels, leather, outdoor, solo, striptease

XXXDan

The teacher calls, I get off to get fucked!

Categories: amateur, anal, big ass, crossdressing, dildo, german, hardcore, lingerie, teacher, teen (18+)

aShemaleTube

Jerking off while dressed

Categories: crossdressing, cum, dress, hd, high heels, jerking, lingerie, teen (18+)

aShemaleTube

Licking leggings

Categories: asslick, crossdressing, domination, hd, high heels, leggings, licking

aShemaleTube

Black Swimsuit

Categories: amateur, black, crossdressing, cumshot, masturbation, small tits, solo, swimsuit

TrannyOne

BUTTS AND SUCKING COCK DICK

Categories: anal, anus, arab, ass, bdsm, black, blowjob, booty, bukkake, creampie

aShemaleTube

Crossdresser Sissy Gina - Street Freak

Categories: big black cock, black, booty, buttplug, crossdressing, cum, hd, high heels, masturbation, nude

ShemaleZ

Ebony Thug Banging Bound Crossdresser

Categories: amateur, banging, bound, crossdressing, ebony, interracial

aShemaleTube

In the kitchen

Categories: amateur, crossdressing, femboy, fetish, homevideo, kitchen, ladyboy, latina

XXXDan

Crossdresser playing anal with vegetables and pee herself

Categories: amateur, anal, big ass, big cock, blonde, crossdressing, european, fetish, insertion, lingerie

KeekAss

Shemamle On Webcam Teasing And Talking

Categories: amateur, beauty, blonde, crossdressing, femboy, garden, homevideo, japanese, masturbation, nylon

KeekAss

Trans Mega-Bitch Gets Caned in Motel

Categories: amateur, bdsm, bitch, blonde, crossdressing, femboy, hd, homevideo, humiliation, motel

KeekAss

Sissy Restrain Bondage - Crossdreser corded and ball-gagged

Categories: amateur, bdsm, blonde, bondage, bound, crossdressing, feminization, fetish, gagging, hd

aShemaleTube

freehand cumshot! Crossdresser sissy slut enjoy sex toy in miniskirt and stockings

Categories: amateur, big cock, crossdressing, cumshot, fetish, hd, homevideo, ladyboy, latex, lingerie

TrannyOne

Cum for me in the End

Categories: amateur, anal, anus, ass, crossdressing, cum, european, extreme, fisting, gay

ShemaleZ

Amateur Shemale Guy 69 Blowjob

Categories: 69, amateur, blowjob, crossdressing

aShemaleTube

Sultry white lace lingerie collection

Categories: blonde, crossdressing, femboy, fetish, hd, lace, ladyboy, lingerie, pantyhose, pov

aShemaleTube

Sissy Mari enjoys her dildo

Categories: amateur, anal, crossdressing, dildo, hd, lingerie, masturbation, sissy, slut, small cock

XXXDan

Hot shemale nurse fucked wildly

Categories: amateur, anal, crossdressing, hardcore, nurse

XXXDan

Transvestite pink

Categories: crossdressing, fetish, lingerie, smoking, transvestite

KeekAss

Ball-Gagged and Thirsty for Boner

Categories: amateur, anal, blowjob, brunette, crossdressing, deep throat, dildo, drooling, feet, fetish

KeekAss

Subjugated Sissy mega-bitch deep buttfuck pummel machine while bound eyes covered & ball-gagged

Categories: amateur, anal, assfucking, bdsm, big ass, bitch, bound, crossdressing, fetish, gagging

ShemaleZ

Two Crossdressers Kissing

Categories: amateur, crossdressing, kissing

aShemaleTube

Femboy riding dildo and cumming a lot

Categories: anal, big ass, big cock, crossdressing, cum, cumshot, dildo, femboy, fetish, hd

KeekAss

Chubby sissy anal dildo masturbation in fishnet bodystocking

Categories: amateur, anal, anal toying, big ass, bodystocking, chubby, crossdressing, dildo, fetish, fishnet

ShemaleMovie

Crossdresser gets a good spanking in naughty role play session

Categories: british, crossdressing, lingerie, masturbation, naughty, office, secretary, spanking, stockings

KeekAss

Beautiful Pretty

Categories: amateur, beauty, blonde, crossdressing, ebony, high heels, homevideo, jerking, ladyboy, masturbation

Pornstars: Sexy Cora

KeekAss

Female with a boner fap with dribbling precum explosion dressed in brief cutoffs

Categories: amateur, beauty, big cock, close up, crossdressing, cumshot, dick, glasses, handjob, hd

KeekAss

Masked CD boinked by machine and have fun with bootie-labia

Categories: amateur, anal, anal toying, beauty, big tits, corset, crossdressing, dick, fetish, funny

TrannyOne

Young 18Yo Tgirls Mutual Sucking N Fucking

Categories: 18 year old, anal, anal toying, anus, asian, ass, assfingering, assfucking, big cock, bitch

ShemaleZ

Denise Adams crossdresser plays with a dildo

Categories: amateur, blonde, crossdressing, dildo, toys

KeekAss

Skinny Asian ladyboy fucked from behind

Categories: amateur, anal, asian, barebacking, crossdressing, femboy, from behind, hardcore, interracial, ladyboy

aShemaleTube

Sissy learns how to cum

Categories: brunette, cage, crossdressing, cum, cumshot, femboy, hd, homevideo, lingerie, masturbation

aShemaleTube

cum in the library

Categories: amateur, crossdressing, cum, cumshot, hd, librarian, lingerie, masturbation, public, sissy

aShemaleTube

Bunny creampie

Categories: anal, big ass, big cock, bunny, creampie, crossdressing, femboy, hd, small tits, teen (18+)

TrannyOne

Ebony wrestler anal fucks busty shemale

Categories: anal, anus, ass, assfucking, bdsm, big tits, black, blowjob, crossdressing, domination

HClips

afellowur CD 3some

Categories: 3some, amateur, blowjob, crossdressing, group sex

aShemaleTube

amateurs sissys cumpilation 2

Categories: amateur, anal, asian, big ass, compilation, crossdressing, cum in mouth, femboy, hd, interracial

aShemaleTube

Balls And Weight Dick Show - S017.1

Categories: amateur, asian, balls, big cock, chinese, crossdressing, dick, femboy, hd, homevideo

aShemaleTube

Tranny Holly's first time in chastity

Categories: amateur, crossdressing, first time, hd, homevideo, mature, model, sissy, smoking, stockings

KeekAss

Will-Less sissy clitty dildoing her donk on the open door while vans pass by

Categories: amateur, anal, anal toying, crossdressing, dildo, exhibitionist, feet, hd, masturbation, public

KeekAss

After Biking Cum Shot Into Nylon Tights

Categories: amateur, bdsm, crossdressing, cum, cumshot, hd, high heels, lingerie, masturbation, mature

TrannyOne

Undressing in C&A Elegant support 70 den in Paloma

Categories: crossdressing, gay, hd, tight, transvestite, undressing

HClips

CDs xxx func

Categories: amateur, crossdressing, lingerie, redhead

aShemaleTube

Pantyhose Experience Hitachi Anal Games

Categories: amateur, anal, barebacking, crossdressing, cumshot, european, femboy, game, hd, masturbation

aShemaleTube

Vegetables anal insertion

Categories: anal, crossdressing, fetish, food, hd, homevideo, insertion, mature, vegetable

ShemaleMovie

Insatiable sissy femboy gets wild anal domination in hardcore gonzo session

Categories: amateur, anal, big cock, blowjob, crossdressing, cum, cumshot, domination, femboy, hardcore

aShemaleTube

La morocha

Categories: amateur, big ass, big cock, crossdressing, cumshot, ladyboy, masturbation, nerdy, solo

KeekAss

lovely femboy in fever after exercise and needs to jism

Categories: amateur, ass, big ass, buttplug, crossdressing, cum, cumshot, cute, femboy, hd