Crossdressing Shemale Videos » 25

aShemaleTube

Pantyluvn sissy H

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

aShemaleTube

Cumshot dildoin'my ass

Categories: amateur, anal, ass, crossdressing, cumshot, dildo, femboy, hd, homevideo, lingerie

aShemaleTube

Granny tranny smoking and showing panty show

Categories: amateur, crossdressing, granny, hd, mature, model, smoking, stockings, tranny, transsexual

aShemaleTube

Tranny Tgurl smoking slut Sarah Millward

Categories: blonde, crossdressing, fetish, hd, homevideo, lingerie, model, sissy, slut, smoking

aShemaleTube

Blue Dress POV

Categories: anal toying, blonde, crossdressing, dress, hd, high heels, lingerie, pantyhose, pov, solo

aShemaleTube

Dirty foursome in hotel room

Categories: 4some, amateur, crossdressing, dirty, hotel, mature

KeekAss

Becca dumps in shining stocking

Categories: amateur, anal, blonde, crossdressing, cumshot, hd, masturbation, mature, nipples, old

aShemaleTube

Drag queen Ursa cums and swallow

Categories: creampie, crossdressing, cum, cum swallowing, cumshot, homevideo, lingerie, masturbation, queen, solo

TrannyOne

Princess Bunnie: Maid for Pleasure

Categories: amateur, bunny, crossdressing, cum, cumshot, european, feet, fetish, french, hd

aShemaleTube

shoe suck

Categories: amateur, blonde, blowjob, crossdressing, fetish, homevideo, mature, pov, shoe, sucking

aShemaleTube

Daisy Taylor Trans SPH small penis humiliation JOI

Categories: bodystocking, crossdressing, dick, domination, femboy, fetish, humiliation, joi, pov, sissy

aShemaleTube

rubber mask live sex doll

Categories: amateur, anal, crossdressing, doll, hd, homevideo, mask, masturbation, rubber, sissy

VideoSection

Seductive tgirl Kapri Sun in amateur crossdressing action

Categories: 18 year old, amateur, ass, barebacking, beauty, big ass, big black cock, big cock, black, brutal

KeekAss

Brunette Sexy Shemale In Red

Categories: amateur, beauty, bed sex, big tits, brunette, crossdressing, cute, hd, homevideo, japanese

aShemaleTube

Turkish Sissy Nesrin Fuck guy and big cum

Categories: ass, big cock, crossdressing, cum, hd, sissy, transsexual, turkish

KeekAss

FN045 That day I needed it the most

Categories: amateur, anal, asian, big cock, brunette, crossdressing, cum, fetish, handjob, joi

KeekAss

nylondelux in wolford neon 40 stocking

Categories: amateur, ass, big ass, crossdressing, feet, fetish, hd, lingerie, nylon, pantyhose

aShemaleTube

Crossdress cosplay Tennis Rosalina panties and anal sho

Categories: anal, cosplay, crossdressing, panties, tennis

VideoSection

Lolafrina's first time pegging, exploring that prostate pleasure

Categories: amateur, compilation, creampie, crossdressing, cum, cum in mouth, cumshot, femboy, first time, jizz

aShemaleTube

Tgirls Cum Is Finger Lick'in Good

Categories: crossdressing, cum, femboy, fingering, licking, masturbation, sissy, tgirl

KeekAss

Nice blondie CD thumbs and slaps their monstrous donk

Categories: amateur, anal, ass, assfingering, blonde, crossdressing, cute, dick, fat, femboy

XXXDan

Nice freshly shaved legs, I love legs more than any other part of the body.

Categories: amateur, asian, beauty, college, cosplay, crossdressing, cute, european, fetish, legs

aShemaleTube

Mature mistress fucked by her slave

Categories: amateur, crossdressing, hd, mature, mistress, slave

KeekAss

Alexa Cosmic t-model swimming at waterfall in t-shirt and t-t-shirt...

Categories: amateur, bathroom, beauty, crossdressing, hd, milf, model, outdoor, small tits, solo

TrannyOne

Teasing my sissy while she is caged. Part 1

Categories: amateur, bdsm, cage, crossdressing, dick, femboy, femdom, humiliation, masturbation, mistress

KeekAss

Lynsey the feminization instructing outdoor Streaking

Categories: 3d, amateur, asian, bisexual, brunette, crossdressing, dick, feminization, ladyboy, nude

KeekAss

Masturbating Contest

Categories: big cock, bondage, british, brunette, contest, crossdressing, dick, fetish, gay, hd

aShemaleTube

Tiano

Categories: amateur, anal, barebacking, big cock, blonde, blowjob, crossdressing, cumshot, femboy, hd

ShemaleMovie

Sissy crossdresser, big cock cumshot

Categories: amateur, asian, babe, beauty, big cock, crossdressing, cum, cumshot, femboy, handjob

ShemaleMovie

Mature Asian shemale sissy solo masturbation session in HD

Categories: amateur, asian, crossdressing, hd, japanese, masturbation, mature, sissy, small cock, solo

XXXDan

Big cock tranny Lucy gets a sloppy deepthroat blowjob from sissy Charlotte

Categories: amateur, bdsm, big cock, big tits, blowjob, british, couple, crossdressing, deep throat, european

KeekAss

Sandy-Haired Femboy Wifey Ass-Fuck

Categories: 18 year old, amateur, anal, anal toying, assfucking, big cock, cosplay, creampie, crossdressing, cumshot

KeekAss

Buttfuck onanism in motel #4

Categories: amateur, anal, anal toying, ass, assfucking, brunette, crossdressing, dildo, hd, huge dildo

TrannyOne

Two crossdressers and a straponed Mistress have some fun together

Categories: 3some, blowjob, crossdressing, funny, lingerie, mistress, slut, spit, strap-on

aShemaleTube

Girl Dick Lovers PMV

Categories: anal, asian, big cock, blowjob, compilation, crossdressing, dick, femboy, hd, latina

aShemaleTube

Cute Crossdresser In Thigh Highs Plays

Categories: amateur, blonde, crossdressing, cute, gay, homevideo

KeekAss

Crossdresser gasping fuck stick

Categories: amateur, bdsm, crossdressing, deep throat, dildo, gagging, hardcore, hd, sloppy, solo

aShemaleTube

wank on bed

Categories: amateur, bed sex, crossdressing, hd, lingerie, sissy, small tits, solo, stockings, wanking

KeekAss

Superhot Shemale Sucking Dildo

Categories: amateur, anal, beauty, blonde, blowjob, crossdressing, cute, dildo, hd, homevideo

Pornstars: Vixxxen

aShemaleTube

Indian Crossdresser goes to Adult Video Store Part 1

Categories: crossdressing, gloryhole, hd, indian, sissy, store, theater

KeekAss

T-Girl ejaculates thru rosy underpants, stocking POINT OF VIEW

Categories: big cock, crossdressing, cum, cumshot, homevideo, lingerie, masturbation, miniskirt, nipples, panties

aShemaleTube

BlueGirl70 Sexy Upskirts 20.02.22

Categories: amateur, crossdressing, fetish, hd, homevideo, solo, stockings, upskirt

TrannyOne

Pretty Asian ladyboy with small tits strokes hairy cock solo

Categories: asian, ass, babe, crossdressing, cum, dick, hairy, huge cock, jerking, ladyboy

ShemaleMovie

Fledgling, crossdressers

Categories: amateur, crossdressing

aShemaleTube

Rubbing Cock between legs

Categories: amateur, crossdressing, cumshot, dick, hd, legs, masturbation, mature, rubbing, solo

aShemaleTube

crossdress VID_20240322_180150

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

HClips

Crazy Sex Video Transvestite Bareback Amateur Hottest , Check It

Categories: amateur, barebacking, crazy, crossdressing, gay, transvestite, uniform

KeekAss

TGIRL THROATING JIZZ-SHOTGUN

Categories: amateur, behind the scenes, big cock, blonde, blowjob, brunette, couple, crossdressing, cumshot, domination

KeekAss

Girl Masker De-Robe Pub Compilation #2

Categories: big ass, big tits, bikini, bisexual, compilation, crossdressing, dildo, fake tits, feminization, huge dildo

TrannyOne

Crossdresserbooty Slow-Mo Twerk Compilation

Categories: amateur, black, booty shake, compilation, crossdressing, ebony, gay, hd, sissy, transvestite

TrannyOne

Freaky little trans whore has bondage sex with perverted guy

Categories: anal toying, bdsm, bondage, crossdressing, perverted, pov, russian, sissy, slut, teen (18+)

aShemaleTube

Nyk0 24

Categories: amateur, anal, asian, crossdressing, femboy, homevideo, masturbation, sissy, teen (18+)

aShemaleTube

Maid maki japanes anal slave.Anal Enema anal sex Anal Fisting

Categories: anal, anal fisting, asian, big tits, crossdressing, enema, japanese, maid, masturbation, sissy

XXXDan

Japanese crossdresser Cosplay

Categories: cosplay, crossdressing, fetish, japanese

KeekAss

Jason and the CD from the pub!

Categories: amateur, anal, big cock, blowjob, crossdressing, gay, hd, huge cock, kissing, muscled

aShemaleTube

caged gurl in a red dress

Categories: anal, black, blonde, crossdressing, dress, hd, stockings, wife

KeekAss

latina femboy ass-fuck trainer with pulverizing machine marika garcia

Categories: amateur, anal, asian, assfucking, big cock, blonde, creampie, crossdressing, daddies, femboy

KeekAss

Crossdresser POINT OF VIEW Teaching Not To Jizz (Surprise Concluding!)

Categories: amateur, anal, anal toying, assfucking, crossdressing, cum, cumshot, dildo, femboy, fur

aShemaleTube

Christina Hearts, with Candy Pants - Slut Cops - Masterbationist

Categories: amateur, big cock, blowjob, cop, creampie, crossdressing, fetish, hd, lingerie, masturbation

TrannyOne

BWC Daddy Cums Back to Breed Crossdresser's Wet Ass Bussy

Categories: amateur, american, anal, anus, ass, big cock, crossdressing, cum, daddies, dick

TrannyOne

Locker room ass fucking for the tranny that wants it bad

Categories: anal, assfucking, blowjob, crossdressing, locker room, slut, teen (18+), tranny

aShemaleTube

Geilesluderlea wichsnutte in Halterlose

Categories: crossdressing, hd, masturbation, sissy, small tits, solo, toys

aShemaleTube

Amateur crossdresser show her body

Categories: amateur, big ass, crossdressing, milf, pantyhose, solo, stockings

TrannyOne

Bodystockings femboi gets fucked in ass by athletic jock

Categories: ass, crossdressing, deep throat, femboy, fetish, gay, hd, lingerie, skinny, tattoo

XXXDan

Delicious trans anal sex

Categories: amateur, anal, beauty, big ass, crossdressing, dildo, gay, hardcore, lingerie, masturbation

aShemaleTube

LaurettaTr and Old Boy Erotic Licking & Finger Game

Categories: amateur, anal, barebacking, blowjob, boy, crossdressing, erotic, femboy, fingering, game

KeekAss

Nice nerdy trans female in fishnets and vinyl crams her booty with ample manhood

Categories: amateur, anal, assfucking, booty, crossdressing, cum, cumshot, cute, dildo, femboy

KeekAss

super-hot joy in black pantyhose (nine)

Categories: amateur, black, crossdressing, high heels, lingerie, masturbation, mature, nipples, pantyhose, posing

TrannyOne

Sissy in lingerie having outdoor anal fun

Categories: amateur, anal, anus, ass, booty, crossdressing, dildo, european, funny, gay

TrannyOne

Blonde crossdresser in stockings and heels enjoys grandpa's old boner

Categories: blonde, crossdressing, grandpa, high heels, old, stockings

aShemaleTube

Santa's sex slave part 1

Categories: big ass, big cock, big tits, crossdressing, cumshot, fetish, hd, lingerie, redhead, slave

HD21

Crossdresser Plays With Buttplug On Webcam

Categories: big ass, big cock, big tits, buttplug, crossdressing, cumshot, masturbation, solo, webcam

aShemaleTube

Black Sequin Dress and Satin Panties (enhanded)

Categories: amateur, black, blonde, crossdressing, dress, hd, homevideo, latina, lingerie, panties

aShemaleTube

Fucking in white thong

Categories: amateur, anal, crossdressing, hd, homevideo, lingerie, masturbation, thong, toys, white

aShemaleTube

BDSM Shemale nun bareback fucked by priest after whipping

Categories: ass to mouth, bdsm, crossdressing, domination, hd, nun, whip

TrannyOne

OUTDOOR ON CAR HOOD STRIP THICK LEGS FAT ASS WIDE CLOSE UP

Categories: amateur, ass, bbw, car, chubby, close up, crossdressing, fat, gay, ghetto

TrannyOne

Fishnet wearing crossdresser in boots is fucked by a tranny

Categories: bdsm, bed sex, boots, crossdressing, doggystyle, fishnet, tranny

aShemaleTube

ATM for DADDY

Categories: amateur, ass to mouth, crossdressing, daddies, hd, homevideo, mature

aShemaleTube

Rio became Ranma?

Categories: amateur, crossdressing, femboy, japanese, sissy

ShemaleMovie

Hot shemale, shemale toy

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

ShemaleMovie

Anal solo play in the FapHouse with magnum-dildo

Categories: anal, anal toying, ass, big ass, crossdressing, dildo, fishnet, fisting, gaping hole, huge dildo

JizzBunker

Crossdresser: I give a footjob with a dildo and cum on my stocking leg

Categories: amateur, compilation, crossdressing, cum, dildo, feet, fetish, footjob, handjob, high heels

aShemaleTube

dildo at the mirror

Categories: amateur, anal, ass to mouth, crossdressing, dildo, hd, lingerie, mirror, sissy, small tits

KeekAss

Alice Latexy adoring a faux-cock while on her knees in the douche

Categories: amateur, blowjob, crossdressing, dick, dildo, doll, fetish, hd, homevideo, knees

aShemaleTube

just me, the slut 4

Categories: ass, bitch, buttplug, crossdressing, sissy, slut, stockings, submissive

TrannyOne

Xtrema witch look 3

Categories: amateur, classic, crossdressing, emo, gay, transvestite, twink, vintage

TrannyOne

Fishnet and corsets make these crossdressers wanna fuck each other

Categories: corset, crossdressing, fishnet

HClips

Alina Russian Crossdresser Anal Destroy

Categories: amateur, anal, assfucking, crossdressing, dildo, fetish, fishnet, hd, jerking, masturbation

aShemaleTube

Lily

Categories: blowjob, crossdressing, cum in mouth, domination, femboy, hd, homevideo, interracial, ladyboy, lingerie

KeekAss

Streaming on Chaturbate @ gurlzdotco

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

XXXDan

Cute Slim Ladyboy Homemade Sexy Performance Short Shorts Cute Bra White Body Shemale Booty Femboy Bi

Categories: amateur, asian, beauty, big ass, big cock, big tits, bisexual, boots, booty, bra

aShemaleTube

Lilith Lovett and Mayumi Sparkles

Categories: asian, crossdressing, cumshot, glasses, hd, ladyboy, lingerie, stockings

KeekAss

Teenager Trap in high stilettos toying with a enormous fuck stick

Categories: amateur, anal, anal toying, big ass, brunette, crossdressing, hd, high heels, homevideo, huge dildo

KeekAss

2 cougars in nylon tights toying with string-on

Categories: black, blowjob, cougar, crossdressing, cum, futanari, hd, lesbian, massage, nylon

KeekAss

Blowage at the Pub turns into a excellent drill with jizm on face and guzzle.

Categories: amateur, anal, blowjob, crossdressing, cum, cum swallowing, cumshot, face fucking, facial, giving head

TrannyOne

Black beauty shoots thick load

Categories: babe, beauty, black, crossdressing, ebony, fat, gay, obese, pretty, thick

HClips

Kelly Lovely In Amateur Crossdresser Gets Fucked In Front Of A Mirror

Categories: amateur, anal, assfucking, barebacking, big cock, blonde, crossdressing, deep throat, dick, hd

XXXDan

DeeDeeSlut69 in a Hot Pink Skirt and White Top out for Training with her toy

Categories: amateur, blowjob, crossdressing, dildo, lingerie, nude, outdoor, public, skirt, solo

HDSex

Horny trans vixen moaning in pleasure as she orgasms

Categories: amateur, compilation, creampie, crossdressing, cum, cumshot, feet, femboy, handjob, homevideo

aShemaleTube

Tranny smoking and showing her panties

Categories: amateur, british, crossdressing, hd, model, panties, smoking, stockings, tranny, transsexual

KeekAss

Swimming, spraying and posing bare in the river...

Categories: amateur, beach, beauty, blonde, crossdressing, fetish, hd, nude, outdoor, posing

KeekAss

Trans Female Deep-Throats and Plows LARGE Fucktoy Before Guzzling Own Jizm

Categories: amateur, anal, anal toying, brunette, crossdressing, deep throat, fetish, hd, masturbation, own cum

TrannyOne

African boy gets fucked by a 2 big black dicks raw

Categories: african, anal, anus, ass, big black cock, big cock, black, blowjob, boy, crossdressing

aShemaleTube

Trine Larsen 2025 Hard Anal

Categories: amateur, anal, big tits, cage, crossdressing, dick, hd, homevideo, mature, sissy

aShemaleTube

Le patronne taille des pipes pour un bonus de Noël. VaneSsaBiTCHx

Categories: amateur, bimbo, blowjob, crossdressing, cumshot, facial, french, hd, sissy, slut

JizzBunker

Heatwave of Desire: Igniting Passion and Pleasure

Categories: beauty, big cock, college, compilation, cosplay, crossdressing, cumshot, masturbation, passionate, pornstar

ShemaleMovie

Young sissy, adult movie star

Categories: amateur, big cock, college, compilation, cosplay, crossdressing, cum, cumshot, jizz, ladyboy

aShemaleTube

Do you like my sexy big ass and my cute butt plug?

Categories: anal, big ass, buttplug, crossdressing, cute, hd, homevideo, masturbation, sissy, teen (18+)

KeekAss

Fuck Stick - Gaby Monserrat - The Plump Railing a Enormous Thick 33 CM Fuck Stick

Categories: amateur, anal, anal toying, bbw, brunette, crossdressing, fat, hd, masturbation, mature

TrannyOne

@Cami_fit12 - YOUR FAVORITE CLIT GIRL!!!

Categories: amateur, clit, close up, crossdressing, dick, small cock, solo, tiny dick, webcam

TrannyOne

Teens Fuck Sexy White Crossdresser TrannyCentral

Categories: amateur, anal, anus, ass, blowjob, brunette, crossdressing, dark hair, feet, fetish

VideoSection

My charming crossdresser with a sexy ass

Categories: ass, crossdressing

KeekAss

Sissy Maid Facialed with Faux Jizm and Cracks Her Fuckin' Machine Before Having a Sissygasm

Categories: amateur, anal, crossdressing, dildo, facial, feminization, fetish, hd, maid, masturbation

JizzBunker

SPH amateur domina teases small cock shemale at CFNM

Categories: amateur, big cock, british, cfnm, crossdressing, dominatrix, european, femdom, fetish, high heels

aShemaleTube

Dana Deana loves cum of T-girls and men

Categories: amateur, compilation, crossdressing, cum, dick, masturbation, mature, sissy, slut, solo

KeekAss

So Willing to Inhale Homosexual Manhood ft Trans Female Dominance

Categories: amateur, babe, big cock, bisexual, blonde, crossdressing, dick, femdom, gay, handjob

aShemaleTube

AMATEUR BODYBUILDER vs Faggyboi

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

aShemaleTube

Sharigurl Enema Milking

Categories: clit, crossdressing, enema, milk, prostate, sissy, slut

TrannyOne

MILF domme anal fists tgirl

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

KeekAss

Sasha De Sade Sissy Inspection Sizzling!

Categories: bdsm, blonde, bondage, crossdressing, dress, femdom, fetish, hd, kinky, maid