Crossdressing Shemale Videos » 45

xHamster

Marilyn Sexual Smoking Fetish Gloved Masturbation Cum Drip

Categories: amateur, american, anal toying, big cock, big tits, crossdressing, cum, fetish, goddess, hd

TrannyOne

Bi anal MILF 3way fucked by crossdresser in MMF 3some

Categories: 3some, anal, bisexual, crossdressing, cum swapping, milf, mmf

aShemaleTube

Submissive latex TS babe barebacked in asshole till cumshot

Categories: ass, ass to mouth, babe, barebacking, big ass, crossdressing, cumshot, hd, homevideo, latex

KeekAss

Sensual Cutie in Compression Have Fun with Cock-Squeezing Harness, Mask and Lil' High-Heeled Shoes.

Categories: amateur, balls, blonde, chubby, cleavage, corset, crossdressing, cumshot, cute, dick

aShemaleTube

Piss play compilation

Categories: compilation, crossdressing, fetish, hd, mature, piss drinking, pissing

TrannyOne

Jaime Camil transformation

Categories: amateur, crossdressing, lingerie, queen, sissy, stockings, transvestite, underwear

xHamster

Trixy Love to Cumming! - Cumming Greatest Hits 2

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

ShemaleMovie

A naughty nymph in an apron welcomes you

Categories: anal, asian, crossdressing, dildo, japanese, ladyboy, lingerie, masturbation, naughty, sissy

aShemaleTube

On my hands and knees waiting for your cock

Categories: crossdressing, dick, hd, knees, mature, model, stockings, tranny, transsexual

ShemaleMovie

Riding session with a sexy sissy in lingerie

Categories: beauty, blonde, braces, crossdressing, femboy, fishnet, jerking, ladyboy, lingerie, masturbation

JizzBunker

Kinky crossdresser in boots corset and seamed tights

Categories: bdsm, boots, corset, crossdressing, kinky, masturbation, webcam

KeekAss

Jerking And A Excellent Blast Pop-shot At The End Massive Elastic Bum Stellar Torrid Towheaded PLUMPER

Categories: big ass, big tits, blonde, crossdressing, cum, cumshot, cute, femboy, hd, jerking

KeekAss

Punk Femboy Plays With Fucktoys - Docking - Crossdressing - Sissygasm TGirl Rails Playthings

Categories: amateur, anal, big cock, boy, brunette, crossdressing, cumshot, feet, femboy, fetish

KeekAss

Glide Until Sissygasm Assfucking Cherry Teaching

Categories: amateur, anal, assfucking, big ass, crossdressing, cum, cumshot, dildo, feet, fetish

KeekAss

Nymph On T-Model Rectal Pegging & Sucky-Sucky Jessica Bloom And Polieana

Categories: amateur, anal, ass, beauty, big cock, blowjob, crossdressing, cum, cum swallowing, facial

KeekAss

TGirl Gigi fake penis humped in the bootie until she sprays grease out of her bum

Categories: amateur, anal, anal toying, crossdressing, dick, dildo, huge dildo, masturbation, mature, orgasm

aShemaleTube

LORD CURVINGTON Cheats on Girlfriend with Faggyboi

Categories: big black cock, blowjob, crossdressing, ebony, fake tits, femboy, gay, girlfriend, hd, lingerie

xHamster

Femboy in a hoodie and stockings bouncing on a dildo, masturbating and cumming

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

xHamster

Marilyn Leather Glove Smoking Fetish 120s Strip Tease

Categories: amateur, american, anal toying, beauty, big cock, blonde, crossdressing, fetish, hd, leather

xHamster

Anal orgasm

Categories: amateur, anal, anal toying, crossdressing, cum, dildo, hd, homevideo, hungarian, lingerie

KeekAss

Spandex Sissy Maid Plays with bud and culo teaser

Categories: amateur, anal, big ass, big tits, brunette, crossdressing, feminization, fetish, gloves, hd

KeekAss

Frolicking with my clitty in undergarments

Categories: amateur, clit, crossdressing, dick, handjob, hd, homevideo, lingerie, masturbation, sissy

KeekAss

Saray amay crossdreser with astolfo costume play

Categories: amateur, anal, cosplay, costume, crossdressing, cum, cumshot, femboy, fetish, handjob

KeekAss

GLORIOUS Dancer transgender princess hotwife at step-mom's guest room with her dresses

Categories: amateur, asian, beauty, big cock, couple, crossdressing, dancing, fetish, hd, homevideo

xHamster

Sissy Taniax -Slut walks part 1

Categories: amateur, colombian, crossdressing, feminization, hd, latina, lingerie, milf, outdoor, public

ShemaleMovie

Intense ebony shemale Luciferx1man puts on a wild strip and twerk show

Categories: amateur, anal, ass, babe, beauty, big ass, big black cock, big cock, creampie, crossdressing

xHamster

Cry For Love - cumshot compilation with sweet memories of severe spanking

Categories: amateur, compilation, crossdressing, cumshot, facial, german, hd, high heels, lingerie, masturbation

aShemaleTube

Sissy faggot joi

Categories: amateur, big cock, crossdressing, hd, joi, ladyboy, masturbation, sissy, solo

TrannyOne

Sissy takes huge enema then bounces on dildo whilst still inflated

Categories: anal toying, crossdressing, dildo, enema, hd, high heels, homevideo, humiliation, lingerie, sissy

xHamster

Marilyn McRow Making Milk in Minutes (Barbarella Rossa)

Categories: amateur, big cock, big tits, british, crossdressing, cumshot, european, hd, homevideo, lingerie

Pornstars: Barbarella

KeekAss

Lovely Sissy is giant devotee of BIG BLACK COCK rapper

Categories: amateur, anal, big black cock, big cock, big tits, black, blowjob, club, crossdressing, deep throat

KeekAss

Toying in pantyhose

Categories: amateur, anal, clit, crossdressing, fetish, handjob, lingerie, masturbation, mature, old

aShemaleTube

crossdress VID_20241209_235048

Categories: amateur, asian, big ass, big cock, chinese, crossdressing, femboy, fetish, hd, homevideo

aShemaleTube

Cum with ass contractions

Categories: ass, big ass, crossdressing, cum, cumshot, femboy, ladyboy, twink

KeekAss

Lovelylilush fuck dildo and cum on face

Categories: bisexual, crossdressing, cum, cumshot, dildo, femboy, fetish, pornstar, sissy, slave

ShemaleMovie

Cute Latina shemale with a perfect booty rides on the sofa

Categories: amateur, anal, ass, beauty, booty, crossdressing, cute, femboy, latina, moaning

xHamster

Preview of Red PVC Dres, Red Thigh High Heel Boots, Cum and Cum Eating

Categories: amateur, boots, british, crossdressing, cum, cumshot, hd, high heels, latex, lingerie

KeekAss

My messy jaws is yours to wreck!

Categories: 18 year old, amateur, anal, big ass, blowjob, brunette, creampie, crossdressing, cute, femboy

xHamster

Out for a walk

Categories: amateur, american, big ass, black, crossdressing, escort, hd, high heels, mature, pantyhose

aShemaleTube

crossdress VID_20240103_000646

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

aShemaleTube

A Tranny's bitch - Laylacross

Categories: anal, ass, bitch, crossdressing, cum, dirty talk, doggystyle, french, hd, kissing

xHamster

Deep Anal Dildo fucking with gape - Sissy fucks herself

Categories: amateur, anal, anal toying, crossdressing, dildo, femboy, gaping hole, german, hardcore, hd

aShemaleTube

smok in chastity

Categories: cage, crossdressing, lingerie, stockings

JizzBunker

Kelly cd feeling horny in the garden

Categories: amateur, british, crossdressing, garden, lingerie, masturbation, mature, nude, outdoor, pantyhose

xHamster

SEXY Hot Skirt White Legs Housewife Ladyboy Homemade Model Crossdresser

Categories: big tits, compilation, crossdressing, cum, cumshot, dancing, hd, homevideo, housewife, ladyboy

xHamster

BIG DICK sissy slut Tiffany Kitten stroking her clit BIG LOAD on high heels shoes 💦

Categories: amateur, beauty, big cock, big tits, blonde, clit, crossdressing, cum, cumshot, dick

xHamster

Hot crossdresser in satin latex and stockings

Categories: amateur, crossdressing, hd, high heels, latex, lingerie, mature, satin, sissy, solo

xHamster

i feel sexy come and fuck that ass

Categories: amateur, anal, ass, bathroom, crossdressing, european, femboy, feminization, fishnet, greek

KeekAss

She said the ladies have an saucy stiffy

Categories: amateur, babe, blowjob, crossdressing, cumshot, cute, dick, domination, femdom, fetish

aShemaleTube

sexy pink bunny loves a big dick in her ass

Categories: anal, ass, ass to mouth, big cock, blonde, blowjob, bunny, creampie, crossdressing, hd

KeekAss

Crossdressers mitt-job close up

Categories: amateur, ass, close up, crossdressing, cum, femboy, fetish, handjob, hd, homevideo

aShemaleTube

CdTina blue nails and cum

Categories: amateur, big cock, crossdressing, cum, fetish, hd, homevideo, lingerie, long nails, masturbation

aShemaleTube

Holly wanking her cock

Categories: amateur, crossdressing, cumshot, dick, hd, homevideo, mature, sissy, solo, stockings

XXXDan

Mummie Marina gets fucked hard by her Mrs Samantha

Categories: amateur, anal, bdsm, beauty, couple, crossdressing, dutch, hardcore, lingerie, mature

HDSex

Ass licking, blow-job, 4k porn

Categories: amateur, anal, ass, asslick, babe, barebacking, beauty, behind the scenes, big ass, blowjob

xHamster

Fisting a New Friend stretch_events, It Seems They Enjoyed Themselves

Categories: amateur, anal, anal fisting, ass, british, couple, crossdressing, cum, domination, extreme

HotMovs

Horny Adult Movie Tranny Solo Exotic , Watch It

Categories: amateur, crossdressing, exotic, gaping hole, gay, hd, piercing, solo, toys, tranny

aShemaleTube

crossdress VID_20240102_213621

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

KeekAss

Crossdresser tear up donk you fuck stick uber-sexy

Categories: amateur, anal, anal fisting, anal toying, creampie, crossdressing, cumshot, dildo, fetish, hd

aShemaleTube

Sissy outfit and upskirts to tease my BLACK DADDY Tre's BB12"NC rock hard for cum

Categories: big ass, black, blonde, crossdressing, cum, daddies, femboy, fetish, hd, interracial

aShemaleTube

CdTina swallowing

Categories: amateur, blowjob, crossdressing, cum swallowing, cumshot, fetish, hd, long nails, mature, sissy

ShemaleMovie

Asia in a ebony & milky with red dress

Categories: asian, crossdressing, dress, ebony, milk

aShemaleTube

Skirt bulge and panty play

Categories: amateur, crossdressing, hd, mature, panties, skirt, stockings

HDSex

Sinfulgrimz loves being a wild sissy femboy

Categories: amateur, american, anal, crossdressing, dildo, emo, femboy, gaping hole, goth, masturbation

aShemaleTube

Redhead teases with her hard cock

Categories: amateur, big cock, crossdressing, dick, lingerie, mature, model, redhead, solo, stockings

xHamster

Cumming From the Penetration!!

Categories: amateur, anal, anal toying, crossdressing, cum, cumshot, dick, hd, masturbation, mature

KeekAss

Hooker Robert Melissa candle fucking

Categories: crossdressing, ladyboy, sissy, slut, solo, tranny, transvestite

xHamster

Fuck cheongsam white stockings TSCD ladyboy

Categories: amateur, anal, asian, beauty, chinese, crossdressing, cum, doggystyle, femboy, fetish

aShemaleTube

Femboi Sissyboi Riding Big Dildo in Micro cage Chastity

Categories: anal, big ass, cage, crossdressing, dildo, femboy, fetish, homevideo, ladyboy, latina

aShemaleTube

crossdress VID_20231226_233825

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

KeekAss

[SISSY] I took out a stiffy from the wedge of the piercing in the park in the daytime.

Categories: amateur, asian, brunette, crossdressing, hd, japanese, ladyboy, outdoor, park, piercing

aShemaleTube

Unicorntrap Bunnybargle - Trap cums at desk

Categories: amateur, anal, big cock, crossdressing, cum, desk, glasses, homevideo, ladyboy, masturbation

KeekAss

Sissy CD mega-bitch candy taking married parent condom-free

Categories: amateur, anal, assfucking, bitch, brunette, condom, crossdressing, dick, doggystyle, hd

KeekAss

Sisgusting crossdressers calling themselves mega-bitch and poke

Categories: amateur, anal, bitch, blowjob, crossdressing, hd, interracial, lingerie, pov

xHamster

Nyl Intense Anal Orgy at the Gym: Hot, Naughty Sluts with Tight Pussies and Gaping Asses Get Hardcore Fucked Threesome

Categories: 3some, anal, asian, ass, barebacking, bbw, big ass, big cock, black, creampie

ShemaleMovie

Mature Tina TV enjoys sipping cum and guzzling it while looking fabulous in pantyhose

Categories: babe, beauty, crossdressing, cum, masturbation, mature, pantyhose, smoking, stockings

XXXDan

Amateur crossdresser Kellycd2022 pissing and masturbating my big sissy gurl cock in white seamless pantyhose

Categories: amateur, big cock, big tits, british, crossdressing, cumshot, dick, masturbation, mature, outdoor

ShemaleMovie

Insatiable sex maniac enjoys a wild ride

Categories: anal, anal toying, bdsm, beauty, big black cock, big cock, crossdressing, cum, cumshot, dildo

xHamster

Pretty pink heels

Categories: bisexual, crossdressing, european, feet, fetish, hd, high heels, italian, ladyboy, licking

xHamster

Cute slut in mini dress pantyhose and heels strips naked in very hot public

Categories: american, anal, big ass, crossdressing, cute, dick, dress, feet, fetish, hd

KeekAss

This Fucktoy was to large

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

KeekAss

Raina Riviere has a peaceful voluptuous fumble and rail sesh

Categories: amateur, anal, anal toying, ass, bbw, big ass, chubby, crossdressing, cum, cumshot

xHamster

Futuretist Intense Anal Domination: Huge White Booty Slut's Tight Ass Gaped by Monstrous Cock, Used as Cum Container

Categories: amateur, anal, asian, ass, barebacking, bbw, big ass, big cock, black, booty

xHamster

Ladyboy Serge Lusin. 2025bc

Categories: amateur, american, crossdressing, european, gay, hd, ladyboy, mature, old, small cock

aShemaleTube

You Can't Miss It - Daddy Gives Me a Triple Orgasm!!!!

Categories: crossdressing, cumshot, daddies, femboy, fetish, hd, homevideo, masturbation, model, orgasm

Pornstars: Viper

xHamster

Walk in the countryside

Categories: big ass, crossdressing, european, feminization, hd, ladyboy, lingerie, mature, outdoor, secretary

xHamster

Striptease with chair

Categories: american, bbw, crossdressing, dress, fetish, hd, homevideo, lingerie, sissy, solo

aShemaleTube

vanity translove buttplug fun

Categories: anal, buttplug, crossdressing, funny, hd, lingerie, sissy, small cock, stockings, tiny dick

aShemaleTube

crossdress VID_20231220_214118

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

KeekAss

Cramming Rubber For My Client

Categories: amateur, big ass, big cock, close up, compilation, condom, crossdressing, cum, cumshot, handjob

KeekAss

SISSY CLITO SPUNK

Categories: amateur, blonde, clit, crossdressing, cum, cumshot, hd, homevideo, ladyboy, lingerie

KeekAss

diminutive pipe plumper sissy compilation

Categories: amateur, bbw, compilation, crossdressing, lingerie, masturbation, plumper, pov, sissy, small cock

KeekAss

Astrid Apathy's G-String-face sissygasm

Categories: amateur, anal, anal toying, clit, condom, crossdressing, cumshot, dick, fetish, lingerie

KeekAss

sissysubkrystal Nail she-male girlfriend sans a condom trans all girl

Categories: amateur, anal, blonde, blowjob, condom, crossdressing, girlfriend, hd, lesbian, lingerie

aShemaleTube

Sweet Sara

Categories: crossdressing

aShemaleTube

Newly Transitioned Tranny Training For Big Dicks

Categories: anal, crossdressing, dick, femboy, fetish, hd, homevideo, ladyboy, sissy, small cock

xHamster

Red high heels MistressxXx

Categories: amateur, anal, beauty, compilation, crossdressing, domination, feet, fetish, greek, hardcore

aShemaleTube

Nerdy CD Inserts Into Her Friend

Categories: amateur, anal, asian, chinese, crossdressing, femboy, friend, nerdy, sissy, stockings

xHamster

Sex Queen

Categories: amateur, crossdressing, cum, hd, latina, queen, sissy, solo, stockings, transsexual

aShemaleTube

Sissyuki anna being fucked

Categories: asian, chinese, crossdressing, hd, sissy

aShemaleTube

Sissy Bitch

Categories: bitch, crossdressing, hd, latex, masturbation, sissy, solo, stockings, toys

xHamster

Smoking cock playing with oil on my big cock and my ass

Categories: amateur, ass, beauty, big cock, colombian, crossdressing, cum, cumshot, dick, femboy

KeekAss

Fetish gloryhole tramp in footwear and vinyl services many firm protection beefsticks

Categories: amateur, anal, bdsm, blowjob, bondage, boots, corset, crossdressing, deep throat, fetish

KeekAss

Super-Sexy Crossdresser High High-Heeled Slippers Stocking on couch with Necklace

Categories: amateur, blonde, couch, crossdressing, high heels, lingerie, masturbation, small tits, solo, stockings

TrannyOne

CD - Miniskirt stockings masturbation

Categories: amateur, crossdressing, gay, hd, lingerie, masturbation, miniskirt, skirt, stockings, transvestite

aShemaleTube

in cute outfit

Categories: anal, blonde, crossdressing, cum in mouth, cute, femboy, gangbang, hd, webcam

aShemaleTube

Sexy femboy with big dick

Categories: big ass, big cock, crossdressing, femboy, ladyboy, sissy, small tits, teen (18+), webcam

xHamster

Ladyboy Serge Lusin. Asshole

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

KeekAss

Stunning Blonde Rubs One Out

Categories: amateur, barebacking, beauty, blonde, brunette, crossdressing, cute, homevideo, jerking, masturbation

aShemaleTube

Hanjobs with a party guy, fucks my feets and accidental piss in mouth - Laylacross FR

Categories: amateur, blonde, blowjob, crossdressing, feet, fetish, footjob, french, handjob, hd

xHamster

getting fucked by a thrusting cock

Categories: amateur, anal, anal toying, big ass, bitch, crossdressing, dick, femboy, german, hd

aShemaleTube

crossdress VID_20231212_211451

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

KeekAss

V-Card sissy Raine frolicking with XXL FAKE PENIS

Categories: amateur, anal, anal toying, big ass, cage, crossdressing, cute, dick, dildo, femboy

aShemaleTube

Scottish Crossdresser shaking my booty on webcam

Categories: big ass, booty, crossdressing, latex, lingerie, scottish, stockings, webcam

aShemaleTube

Tranny in red dress has fun on her monster dildo

Categories: amateur, anal, crossdressing, dildo, dress, femboy, funny, hd, toys, tranny

aShemaleTube

pushing a carrot up my sissy cunt

Categories: amateur, anal, big tits, crossdressing, cunt, food, hd, insertion, lingerie, mature

TrannyOne

Tranny in leather mini skirt anal fucks guy

Categories: anal, anus, ass, assfucking, bdsm, blowjob, crossdressing, domination, fetish, hardcore

aShemaleTube

Dildo sucking sissy slut

Categories: amateur, blonde, blowjob, crossdressing, deep throat, dick, dildo, femboy, hd, sissy

xHamster

C⁴ [²⁰mar²⁵](8) The Black Panther😼

Categories: amateur, ass, bdsm, big cock, bitch, crossdressing, cute, fetish, french, hd

Pornstars: Black Panther

aShemaleTube

Sissy gets Messy Facial At the Gloryhole!

Categories: bimbo, crossdressing, dick, facial, gloryhole, hd, messy, model, sissy, transsexual