High Heels Shemale Videos » 16

Sex3

Beautiful shemale in high heels, solo pleasure.

Categories: anal toying, assfingering, beauty, brunette, cameltoe, high heels, masturbation, model, orgasm, pussy

KeekAss

Outdoor Pop-Shot Of A Rock Hard Slapped Sissy

Categories: amateur, crossdressing, cum, cumshot, high heels, lingerie, masturbation, mature, nylon, outdoor

xHamster

Dark haired ladyboy with high heels gets fucked doggystyle

Categories: amateur, anal, asian, barebacking, couple, cum, cumshot, dark hair, doggystyle, hd

KeekAss

COUGAR she-creature flashing off and groping in black softcore undergarments and high stilettos

Categories: amateur, black, blonde, cougar, crossdressing, fetish, flashing, groping, high heels, homevideo

xHamster

BBC Fetish Foot Queen

Categories: amateur, asian, beauty, big black cock, crossdressing, feet, femboy, fetish, footjob, hd

XXXDan

Crossdresser Kellycd2022 on vacation, amateur tranny milf masturbates with big cum in sexy pantyhose with heels

Categories: amateur, beauty, big cock, british, crossdressing, cum, cumshot, handjob, high heels, lingerie

its.PORN

Shemale boss Eva Maxim facefucks employee for spreading rumors

Categories: anal, big tits, blowjob, boss, brunette, dick, face fucking, fake tits, high heels, oral

AnalDin

Transsexual Hispanic nailed from behind before cowgirl

Categories: anal, ass, assfucking, big tits, cowgirl, from behind, high heels, latina, tease, tranny

XXXDan

Young French transvestite in fishnet stockings has solo fun. Do you want to join me?

Categories: amateur, anal, big ass, crossdressing, dildo, european, fishnet, french, gay, hardcore

KeekAss

Welcome to the Candy Store2

Categories: anal, asian, assfucking, big cock, big tits, blowjob, brunette, dick, fake tits, fishnet

KeekAss

Lactating ebony TS sucks on big dildo and jerks off her BBC

Categories: anal, big black cock, big tits, cumshot, dildo, ebony, fetish, high heels, lactating, masturbation

HotMovs

Slim teen 18+ ladyboy with high heels strips and sucks her lover's cock

Categories: amateur, asian, blowjob, cumshot, dick, domination, extreme, high heels, ladyboy, slim

aShemaleTube

Getting hard at home High Heel Boots Masturbation Cum

Categories: amateur, asian, beauty, boots, compilation, crossdressing, cum, cumshot, hd, high heels

KeekAss

Pretty shemale trap screwing with her handsome man

Categories: anal, beauty, big cock, big tits, blowjob, cumshot, fetish, fishnet, high heels, latina

JizzBunker

Cute crossdresser fucks dildo in sexy dress

Categories: amateur, anal, beauty, crossdressing, cute, dildo, dress, handjob, hardcore, high heels

KeekAss

She-Male gets torn up by her neighbor in crimson underwear and high-heeled slippers

Categories: amateur, ass, asslick, beauty, big ass, blonde, brunette, crossdressing, cum, gorgeous

ShemaleMovie

Seductive shemale kellystar518 in lingerie explores sissy fantasies

Categories: american, anal, anal toying, ass, beauty, big black cock, big cock, crossdressing, cum, cumshot

XXXDan

Cervin Luxury Stocking Shiny Skirt 4K

Categories: amateur, anal, beauty, big cock, crossdressing, cumshot, dildo, feet, fetish, hardcore

KeekAss

Robed like a Doll - but just a screwable super-bitch

Categories: amateur, anal, anal toying, bitch, brunette, crossdressing, doll, fur, hd, high heels

KeekAss

Exotic shemale shows off curves in bathroom and jerking off

Categories: anal, bathroom, big cock, big tits, dildo, exotic, fetish, high heels, jerking, masturbation

XXXDan

Accessorize like a pro: enhance your outfits

Categories: amateur, beauty, big ass, big cock, big tits, compilation, cosplay, crossdressing, high heels, lingerie

KeekAss

ultra gams in fishnets (trio)

Categories: amateur, crossdressing, fishnet, high heels, legs, lingerie, mature, nipples, posing, slut

aShemaleTube

Daniela dildo insertion

Categories: amateur, dildo, hd, high heels, insertion, lingerie, stockings, toys

XXXDan

Me getting fucked in heels

Categories: anal, blowjob, hardcore, high heels, mature, norwegian, teen (18+)

xHamster

stripper shoes - public crossdressing

Categories: amateur, crossdressing, european, feet, femboy, fetish, hd, high heels, lingerie, outdoor

xHamster

In Heels, Then Collapsed Like a Queen

Categories: amateur, big cock, black, cum, cumshot, cute, hd, high heels, latina, masturbation

xHamster

latex cumwhore enjoying xxxxl Dildo

Categories: anal fisting, anal toying, bdsm, big cock, cum, danish, dick, dildo, european, extreme

XXXDan

Ts valkyria domina fucks mature milf ts meja foss

Categories: anal, big cock, big tits, clothed sex, doggystyle, dominatrix, european, hardcore, high heels, mature

KeekAss

TranssexualNetwork.com - Redhead ts trap's fat dick hard squeezing masturbation

Categories: big cock, dick, fat, high heels, lingerie, masturbation, redhead, small tits, solo, tranny

AnalDin

Darkhaired shemale strokes her big shaft after stripping

Categories: big tits, brunette, dark hair, high heels, lingerie, masturbation, solo, striptease, tattoo, tranny

TrannyOne

Muscled masculine tranny gives titjob to busty blonde MILF - Prime Suspect Pounding Eva Paradis

Categories: anal toying, ass, big ass, big tits, blonde, blowjob, booty, bus, cumshot, dick

KeekAss

Scorching sandy-haired Tv whore vinyl stocking flashing her nub and vag

Categories: amateur, crossdressing, cuckold, fetish, flashing, high heels, latex, lingerie, mature, pussy

aShemaleTube

A Slut in a Grove (june 29, 2025) Looking for Cocks. French Transvestite Exhibition Vanessabitchx

Categories: amateur, big ass, crossdressing, dick, european, exhibitionist, fishnet, french, hd, high heels

KeekAss

Latina trap fucked with big dick after playing around

Categories: anal, big cock, big tits, blowjob, fetish, high heels, kitchen, latina, masturbation, tranny

JizzBunker

Kellycd2022 video for the first time clothed urinating in panties and stockings masturbating cumshot

Categories: amateur, british, clothed sex, crossdressing, cumshot, first time, high heels, lingerie, masturbation, mature

xHamster

Joselynne Crossdreser In High Heels And Short Dress Show Ass And Legs

Categories: amateur, ass, big ass, crossdressing, dress, feminization, hd, high heels, legs, lingerie

KeekAss

Lovely trans nurture getting to anally know her patient

Categories: anal, barebacking, big cock, blowjob, brunette, costume, cum in mouth, fishnet, glasses, hd

KeekAss

Marina and Mrs Samantha drilling using a large black dual fake penis!

Categories: amateur, anal, anal toying, beauty, black, blonde, crossdressing, dick, dildo, drilling

aShemaleTube

Leather,Satin and fur on the outside,no panties and butt plug underneath

Categories: amateur, american, anal toying, beauty, buttplug, crossdressing, escort, fetish, fur, hd

ShemaleMovie

Marina gets tied up, teased, and pleased in a steamy threesome with Mirjam and Samantha

Categories: 3some, bdsm, beauty, blonde, bondage, chained, domination, high heels, lingerie, spanking

xHamster

I Enjoy Feeling My Ass and Stroking My Asshole

Categories: amateur, ass, cumshot, high heels, masturbation, small tits, solo, stockings, stroking

aShemaleTube

I'm testing out some unpretentious, but impactful, trinkets.

Categories: big clit, crossdressing, european, feet, fetish, french, hd, high heels, lingerie, masturbation

XXXDan

Kelly cd wanking outdoors in the garden in purple see thru

Categories: amateur, beauty, british, crossdressing, cumshot, garden, high heels, lingerie, masturbation, mature

PornGem

Michael and Jade fucks after the photoshoots

Categories: anal, ass to mouth, big cock, big tits, blonde, blowjob, brunette, cum, cumshot, doggystyle

KeekAss

Enjoyment in satin slide and wonderful brassiere and g-strings... with my clitty.

Categories: amateur, ass, big cock, big tits, bra, crossdressing, dick, glasses, high heels, lingerie

XXXDan

Some of my shoes, wich ones do you wanna lick?

Categories: boots, compilation, crossdressing, european, feet, fetish, french, high heels, licking, small tits

ShemaleMovie

Sissy Kelli strolls through a hotel hallway with a dildo gag

Categories: amateur, bdsm, bondage, boots, british, crossdressing, dildo, domination, european, exhibitionist

XXXDan

IR bigbutt transgender latina with high heel boots gets fucked

Categories: amateur, anal, babe, big ass, big tits, boots, handjob, high heels, interracial, latina

KeekAss

Bigboobed Mexican tgirl flashes caboose before stroking off

Categories: big ass, big cock, big tits, brunette, fake tits, flashing, handjob, hd, high heels, lingerie

KeekAss

TranssexualNetwork.com - Glam shemale's hot female three-hole fucking fest

Categories: anal, babe, big cock, big tits, blowjob, cumshot, deep throat, doggystyle, fishnet, hd

xHamster

Crossdresser and Trans Woman Using Fucking Machine - Compilation 7

Categories: amateur, american, anal, barebacking, beauty, big ass, compilation, crossdressing, femboy, fucking machine

XXXDan

Brunette ladyboy in high heels gets her big cock sucked by

Categories: amateur, anal, asian, big ass, big cock, blowjob, brunette, couple, cumshot, facial

KeekAss

Marvelous Trannys Love Humping Taut Butthole

Categories: anal, ass, blowjob, brunette, creampie, cumshot, dildo, erotic, hardcore, hd

aShemaleTube

Busty ladyboy in black dress jerks off with her high heels

Categories: amateur, amazing, asian, big tits, black, cum, cumshot, dress, high heels, ladyboy

KeekAss

Brittney and Kenzie are alone in the studio

Categories: ass, barebacking, big ass, big cock, big tits, blonde, blowjob, brunette, cum, dark hair

KeekAss

Mrs Samantha and marionette Tgirl Marina in a long dual-fake penis humping sesh

Categories: amateur, anal, anal toying, beauty, black, blonde, crossdressing, dick, dildo, fetish

aShemaleTube

Trixy Giving Perfect Service

Categories: amateur, anal, barebacking, big cock, blowjob, crossdressing, cumshot, hd, high heels, mature

JizzBunker

Highheels tgirl assravaged bareaback

Categories: amateur, anal, big tits, fetish, gay, handjob, high heels, masturbation, redhead, tgirl

aShemaleTube

Fucking my ass while caged and wearing heels

Categories: amateur, anal, ass, ass to mouth, big ass, big tits, blonde, hd, high heels, homevideo

JizzBunker

Jen: Disco Kitchen

Categories: anal, big cock, disco, high heels, kitchen, panties

XXXDan

Whores FanTasme. CAM in the Forest of Brunoy91 June CuMSLuT in search of Sperm offerings in VaneSsaBiTCHx

Categories: amateur, beauty, crossdressing, european, fantasy, fishnet, forest, high heels, lingerie, nude

xHamster

The Lady Wanks In Three-Four Time

Categories: amateur, crossdressing, cumshot, german, hd, high heels, lingerie, masturbation, mature, pantyhose

JizzBunker

Redhead ladyboy with high heels loves to get fucked

Categories: amateur, anal, asian, big ass, blowjob, couple, cumshot, facial, gay, handjob

TrannyOne

Princess Bunnie: Pink Sequin Prom Dress Masturbation

Categories: crossdressing, dress, high heels, masturbation, solo, tranny

aShemaleTube

Blonde shemale with high heels and latex dress fucks a dude till facial

Categories: anal, big ass, big cock, big tits, blonde, blowjob, cumshot, domination, dress, facial

CrocoTube

Dashing shemale slut craves anal more than anything

Categories: anal, bed sex, bedroom, blowjob, fake tits, hd, high heels, legs, nipples, pantyhose

KeekAss

high heel breezy in fishnets

Categories: crossdressing, fishnet, high heels, legs, lingerie, masturbation, mature, moaning, nipples, posing

aShemaleTube

Big dick ladyboy with high heels masturbates solo in bed

Categories: amateur, amazing, asian, bed sex, big cock, cum, cumshot, high heels, ladyboy, lingerie

aShemaleTube

Tattooed Asian shemale with high heel boots pumps her small dick

Categories: amateur, asian, boots, high heels, ladyboy, masturbation, small cock, solo, tattoo, teen (18+)

aShemaleTube

Brunette ladyboy with high heels jerks off solo on the couch

Categories: amateur, asian, brunette, couch, high heels, ladyboy, masturbation, solo, teen (18+)

KeekAss

Jacking Office Gurl - popshot like a thunderclap

Categories: amateur, ass, blonde, crossdressing, cum, cumshot, high heels, lingerie, masturbation, mature

ShemaleZ

Hot Shemale Rides A Big Hard Cock On The Sofa

Categories: anal, assfucking, barebacking, big cock, brunette, deep throat, dick, hd, high heels, small tits

xHamster

Steph in white

Categories: amateur, flashing, hd, high heels, lingerie, solo, stockings, white

CrocoTube

The greatest costume party with April O'Neil and Lena Kelly, the hottest guests.

Categories: blonde, blowjob, costume, fake tits, from behind, high heels, moaning, party, redhead, stockings

KeekAss

Ass fucking getting off makes this tranny jizz sploog

Categories: anal, ass, assfucking, beauty, big ass, booty, brunette, cum, cumshot, dick

XXXDan

Satin Temptress 2

Categories: amateur, crossdressing, dildo, fetish, high heels, lingerie, masturbation, mature, pornstar, satin

Pornstars: Temptress

aShemaleTube

cute skinny milf in white floral dress and white lingerie red high heels cum intense

Categories: amateur, big cock, cum, cumshot, cute, dress, hd, high heels, homevideo, lingerie

ShemaleMovie

Guy fucks shemale, shemale reverse cowgirl

Categories: blowjob, cowgirl, cumshot, fishnet, high heels, teen (18+)

CrocoTube

Insolent tranny lets black stud smash her muff in crazy rounds

Categories: anal, black, blonde, blowjob, crazy, doggystyle, fake tits, from behind, hd, high heels

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

KeekAss

Draining In The Rain - in miniskirts and nylon tights

Categories: amateur, brunette, crossdressing, cum, cumshot, high heels, lingerie, masturbation, mature, milf

aShemaleTube

Blonde skinny ladyboy with high heels jerks off her long dick

Categories: amateur, asian, blonde, dick, high heels, ladyboy, masturbation, skinny, solo, teen (18+)

xHamster

crossdresser with amazing feet on a night walk in the park

Categories: amazing, crossdressing, european, feet, hd, high heels, outdoor, park, polish, pov

XXXDan

Slim tranny in white fishnet stockings face fucked on the couch

Categories: anal, asian, couch, face fucking, fishnet, high heels, lingerie, slim, stockings, tranny

KeekAss

wondrous butt in black pantyhose (two)

Categories: amateur, ass, big ass, black, crossdressing, high heels, legs, masturbation, mature, moaning

xHamster

Busty MILF Nadia seduces lucky Christian

Categories: anal, barebacking, big tits, cumshot, hd, high heels, ladyboy, mature, milf, seduce

xHamster

Big Booty Tease in Bodysuit lace leotard

Categories: amateur, big ass, big cock, booty, british, crossdressing, dick, femboy, hd, high heels

KeekAss

Selfbondage plowed by machine gone wrong

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

xHamster

Laci furthers her training in new fishnets and heels

Categories: amateur, american, anal, ass, big ass, crossdressing, dildo, femboy, feminization, fishnet

KeekAss

GROOBY ARCHIVES Holly Masturbates Perceives Insane To Jerks

Categories: big ass, big tits, black, blonde, handjob, hd, high heels, masturbation, miniskirt, solo

ShemaleMovie

Agatha indulges in anal pleasure with a fancy dildo

Categories: anal, anal toying, big cock, dildo, fishnet, high heels, masturbation, toys

KeekAss

Nady and Sofy live cam demonstrate 2 tiny dame sissy broads are nasty like 2 lil' dame dogs in fever

Categories: amateur, blonde, blowjob, crossdressing, fetish, handjob, hd, high heels, lesbian, lingerie

aShemaleTube

Gio trav loves black cocks

Categories: amateur, big ass, black, dick, dildo, european, hd, high heels, italian, mature

aShemaleTube

Slim ladyboy with high heels takes off her bikini and strokes her long cock

Categories: amateur, asian, bikini, dick, high heels, ladyboy, masturbation, slim, solo, teen (18+)

XXXDan

Tattooed Latin tranny with big ass in red heels gets anally drilled

Categories: anal, big ass, big tits, drilling, high heels, latina, milf, tattoo, tranny

ShemaleZ

Blond Trannies Fuck And Masturbate Together

Categories: anal, assfucking, big ass, big tits, blonde, booty, booty shake, deep throat, hd, high heels

xHamster

I'm a Policewoman and I Find a Very Exciting Clue

Categories: amateur, anal, cop, crossdressing, handjob, hd, high heels, lingerie, masturbation, mature

XXXDan

Dominatrix humiliates a transvestite with a small dick in womens clothing

Categories: abuse, amateur, big cock, british, brunette, cfnm, clothed sex, crossdressing, dominatrix, european

KeekAss

Cool ill Sophie Jacks in Mini Micro-Skirt, Diamond nets, Sumptuous stilettos and a Crimson vinyl Top

Categories: amateur, beauty, brunette, crossdressing, fetish, fishnet, high heels, masturbation, miniskirt, pov

xHamster

Big Booty Workout Chick Skips the Gym

Categories: anal, barebacking, big ass, big cock, blowjob, booty, gym, hd, high heels, ladyboy

XXXDan

Housewife cleans up your mess

Categories: amateur, big ass, big cock, blonde, high heels, housewife, maid, milf, pov, small cock

VipTube

Slim ladyboy with high heels shows off her hairy dick and

Categories: big tits, dick, hairy, hd, high heels, ladyboy, masturbation, slim, solo

xHamster

Slim ladyboy with high heels shows off her hairy dick and

Categories: amateur, asian, cum, cumshot, dick, hairy, hd, high heels, ladyboy, lingerie

XXXDan

Adoration queen of the damned

Categories: amateur, bdsm, big cock, crossdressing, feet, fetish, fishnet, high heels, lingerie, queen

xHamster

new TS starlet gags on a big cock

Categories: amateur, beauty, big cock, big tits, blowjob, cum in mouth, cumshot, dick, handjob, hd

JizzBunker

Me in black high heels, black fishnet tights and red painted nails

Categories: amateur, big cock, black, crossdressing, european, feet, fetish, fishnet, french, high heels

KeekAss

Humping my fuck stick two

Categories: amateur, anal, anal toying, creampie, crossdressing, dildo, doggystyle, gaping hole, hd, high heels

aShemaleTube

Sissy coming home from work

Categories: amateur, anal, anal toying, bdsm, crossdressing, cuckold, feminization, fetish, high heels, homevideo

VideoSection

Hot cop stumbles upon an arousing lead

Categories: anal, cop, crossdressing, handjob, high heels, lingerie, masturbation, stockings, toys, uniform

KeekAss

GENDERFLUXXX - MTF TRANSSEXUAL boy belt dick screws spandex stunner arse after pussylicking

Categories: anal, ass, babe, blowjob, boy, brunette, dick, fetish, gloves, hd

ShemaleZ

Busty Shemale Riding Horny Slut In The Garden

Categories: anal, assfucking, big cock, big tits, brunette, classic, dick, garden, high heels, hooters

xHamster

Classy & Elegant - White Blouse and Black Maxi Skirt

Categories: american, asian, black, crossdressing, hd, high heels, lingerie, mature, skirt, stockings

XXXDan

Cute sexy tranny in bikini and heels in public, very hot

Categories: anal, big ass, big cock, bikini, crossdressing, cute, feet, fetish, hardcore, high heels

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

aShemaleTube

Big CD Cock Rubbing on Table POV Cumshot

Categories: amateur, big cock, crossdressing, cum, cumshot, dick, hd, high heels, homevideo, lingerie

ShemaleMovie

Latina ebony shemale getting dressed behind the scenes

Categories: behind the scenes, ebony, high heels, latina, tattoo

PornGem

Busty Trans babe licks and fucks Ebony pussy in bathroom

Categories: assfingering, babe, bathroom, big tits, black, ebony, hairy, high heels, licking, pussy

KeekAss

lisa climaxes in stilettos

Categories: amateur, crossdressing, feet, fetish, high heels, legs, lingerie, masturbation, orgasm, pov

aShemaleTube

Sissy Outside and Inside BBC Dildo Play

Categories: amateur, anal, anal toying, bdsm, big black cock, crossdressing, dildo, feminization, fetish, high heels

xHamster

Cane Crop Cum - I cant get enough of it

Categories: amateur, crop whip, crossdressing, cum, german, hd, high heels, lingerie, masturbation, mature