High Heels Shemale Videos » 30

JizzBunker

Big ass Latina trans babe in stockings and heels barebacked

Categories: anal, babe, barebacking, big ass, big tits, gay, high heels, latina, lingerie, stockings

KeekAss

Alisya JC going knuckle deep solo anal invasion have fun with faux-cock and plug

Categories: amateur, anal, anal fisting, anal toying, assfucking, beauty, blonde, buttplug, crossdressing, dick

PornGem

ASIANTGIRL - Da's First Striptease and Masturbation

Categories: asian, brunette, cute, hd, high heels, masturbation, softcore, solo, striptease, tgirl

TrannyOne

Horny tranny babe teases the hot guy into fucking his juicy ass deep and hard with her big Tcock

Categories: 69, anal, anus, ass, babe, ball licking, balls, beauty, bed sex, bedroom

KeekAss

Glance at my Handsome Soles While I Have fun with Myself

Categories: amateur, anal, beauty, big ass, big black cock, dildo, feet, femboy, fetish, french

JizzBunker

Brunette ladyboy with short hair in high heels jerks off solo

Categories: amateur, asian, big ass, brunette, cumshot, handjob, high heels, ladyboy, lingerie, masturbation

TrannyOne

Japanese ladyboy beauty lifted and analfucked

Categories: amateur, anal, anus, asian, ass, babe, beauty, feet, fetish, high heels

VipTube

Tattooed Asian shemale with high heel boots pumps her small

Categories: amateur, asian, big tits, boots, cumshot, hd, high heels, ladyboy, masturbation, solo

JizzBunker

Tranny bitch takes a hard cock in the ass

Categories: anal, ass, asslick, big ass, big cock, big tits, bitch, blowjob, couple, dick

TrannyOne

Tranny Surprise - All Flavor

Categories: anal, anus, ass, big tits, blowjob, brunette, close up, condom, couch, couple

aShemaleTube

Purple skirt

Categories: ass, boots, chubby, cum swallowing, cumshot, dildo, hd, high heels, masturbation, pov

XXXDan

Punk Rock Trans Anal Princess

Categories: amateur, anal, big ass, big cock, cowgirl, dildo, hardcore, high heels, huge dildo, lingerie

TrannyOne

Blonde shemale goddess seduces a guy to fuck his tight ass nice and hard

Categories: anal, ass, belly, big tits, blonde, blowjob, couple, cum, cumshot, feet

KeekAss

GROOBYGIRLS Blowage and anal invasion getting off with fuck stick

Categories: anal, anal toying, black, curly haired, cute, deep throat, dick, dildo, dress, hd

JizzBunker

Naomi Chi poses in red lingerie with black stockings and high heels with her legs spread on a sex swing while doing her

Categories: amateur, big ass, big cock, big tits, black, blonde, fetish, flashing, hardcore, high heels

TrannyOne

Transsexual Lesbian Tranny Assfucks Babe

Categories: amateur, anal, anus, ass, assfucking, babe, bdsm, beauty, blonde, blowjob

Pornstars: Melody Star

aShemaleTube

Indian Sissy hooker Pimped Out on the Streets

Categories: crossdressing, hd, high heels, indian, sissy, slut, street

TrannyOne

Innocent man gets his ass plowed by the naughty TS babe

Categories: anal, anus, ass, babe, beauty, bed sex, bedroom, belly, big tits, brunette

Pornstars: Mariana Cordoba

VideoSection

Supremacy, shemale ass

Categories: amateur, ass, bdsm, big ass, crossdressing, domination, femboy, high heels, ladyboy, latina

aShemaleTube

daylight slutwalk in cute minidress and heels

Categories: amateur, big ass, caught, crossdressing, cute, dress, femboy, fetish, hd, high heels

TrannyOne

Nerdy man gets his ass penetrated deep by the sexy Asian ladyboy

Categories: anal, anus, asian, ass, bathroom, bed sex, bedroom, bikini, condom, couch

aShemaleTube

Caucasian trap. End

Categories: european, high heels, lingerie, mature, milf, outdoor, pantyhose, sissy, stockings

KeekAss

Couple Having Some Fun In Cam 2

Categories: anal, barebacking, beauty, big cock, brunette, couple, crossdressing, cute, feet, femboy

TrannyOne

Poor guy gets his skinny ass destroyed by the nasty trans chick

Categories: anal, anus, ass, bdsm, belly, brunette, couple, cum, cumshot, dark hair

KeekAss

Wenona opens her pussy for Bianca Blakes sharp tranny dick

Categories: babe, big cock, big tits, blowjob, cumshot, curvy, dick, facial, fetish, fingering

KeekAss

CROSSDRESSER IN PANTYHOSE AND SHOES WITH a HIGH HEEL IN THE BELT OF PURITY AND NIP CLOTHESPINS

Categories: amateur, anal, blonde, boots, brunette, cage, compilation, crossdressing, hd, high heels

aShemaleTube

Elena with New Videos with High Heels Enjoy It

Categories: amateur, anal, bbw, close up, crossdressing, cum, cumshot, dirty talk, greek, high heels

JizzBunker

Mrs. Samantha and Sir Rob treat sluts Els to some great ass play!

Categories: 3some, amateur, anal, ass, bdsm, big ass, dutch, fisting, high heels, mature

TrannyOne

Princess Bunnie: Maid for Pleasure

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

aShemaleTube

Redhead ladyboy with high heels strokes her shaved cock till messy cumshot

Categories: amateur, asian, cumshot, dick, high heels, ladyboy, masturbation, messy, redhead, shaved

TrannyOne

Innocent man gets a big and hard surprise is his ass and mouth by the kinky Ts babe

Categories: anal, anus, ass, babe, beauty, big tits, brunette, couch, couple, cum

aShemaleTube

Princess Bunnie: Trans MILF Cums in her Corset and Pantyhose

Categories: corset, crossdressing, cum, cumshot, hd, high heels, lingerie, masturbation, mature, milf

aShemaleTube

Brunette 'n Horny

Categories: brunette, crossdressing, dress, hd, high heels, pantyhose, solo, sucking, toys

TrannyOne

[Trans] Porn On The 4th of July!

Categories: 3d, anal, anus, ass, blowjob, brunette, cowgirl, dark hair, feet, fetish

aShemaleTube

Sexy Crossdresser Kellycd2022 in sexy white dress and heels

Categories: amateur, big cock, big tits, crossdressing, cumshot, dress, femboy, high heels, masturbation, mature

aShemaleTube

FRANKS-TGIRLWORLD: Showtime with Arriya

Categories: asian, hd, high heels, masturbation, slim, softcore, solo, striptease, tattoo, tgirl

TrannyOne

Hot For Transsexuals #7: Aspen Brooks & Chad Diamond

Categories: anal, anus, ass, bed sex, bedroom, belly, big tits, blowjob, brunette, close up

aShemaleTube

Julia X Sweet Release

Categories: big cock, cumshot, femboy, hd, high heels, homevideo, lingerie, masturbation, pornstar, sissy

Pornstars: Sweet Julia

TrannyOne

Hot Beautiful TS Filipina Buxom Asian Shemale

Categories: asian, beauty, brunette, buxom, dark hair, feet, fetish, filipina, high heels, ladyboy

KeekAss

Redhead Brenda Von Tease plunges dildo in TS Bella Rossis rear

Categories: anal, babe, big cock, big tits, blowjob, cum, cumshot, dildo, drilling, fetish

Pornstars: Bella Rossi

aShemaleTube

Sissy pansy Andreina

Categories: barebacking, cage, crossdressing, glasses, hd, high heels, homevideo, lingerie, mature, redhead

TrannyOne

Busty TS chick dominates a hogtied submissive masked man

Categories: anal, anus, ass, bdsm, bed sex, bedroom, big tits, bondage, couple, cum

Pornstars: Jessy Dubai

KeekAss

Ginger Asian ladyboy teasing and tugging her juicy dick

Categories: anal, asian, big cock, cumshot, dick, fetish, fishnet, high heels, juicy, ladyboy

TrannyOne

Babe Pink Hair, Pink Heels, Dick Suck *messy Facial*

Categories: anal, anus, ass, babe, bdsm, beauty, blowjob, cum, cumshot, dick

aShemaleTube

Big cock crossdresser Lucy anal dildo fucking

Categories: amateur, anal, anal toying, big cock, big tits, british, crossdressing, dildo, fucking machine, high heels

XXXDan

Kellystar518 in the movie Locked Lover

Categories: bdsm, big ass, big cock, bondage, boots, cosplay, crossdressing, fishnet, hardcore, high heels

TrannyOne

Busty Rosy Pinheiro Visiting Her Friend After The Gym. (Participation Valter Andrade)

Categories: anal, anus, ass, bdsm, big tits, blowjob, brunette, condom, couch, couple

aShemaleTube

Busty Asian shemale with high heels plays with her puffy nipples

Categories: amateur, asian, big tits, high heels, ladyboy, masturbation, puffy nipples, solo, teen (18+)

JizzBunker

Mrs. Samantha in a red dress, red boots and black gloves spanks her tranny slave Marina while chained to the ceiling!

Categories: amateur, bdsm, beauty, black, blonde, boots, chained, couple, crossdressing, dress

TrannyOne

New Years Bang: Chelsea Marie Frees Butt Slut From Chastity

Categories: anal, anus, ass, bdsm, belly, big tits, close up, couch, couple, cum

aShemaleTube

Poupée Salope Travestie Esclave Sexuelle Francaise VaneSsaBiTCHx prt1

Categories: amateur, big cock, crossdressing, domination, fetish, french, hd, high heels, lingerie, masturbation

JizzBunker

Cute blonde tranny with firm tits Afrika Campos plays with her big cock in ripped pantyhose and heels, trying to get herself in order

Categories: amateur, beauty, big ass, big cock, blonde, cute, high heels, latina, lingerie, masturbation

Pornstars: Africa

TrannyOne

Diana Hx gets new clothes from delivery guy

Categories: anal, anus, ass, blowjob, bra, brunette, clothed sex, couple, dark hair, delivery guy

aShemaleTube

FULL video of ladyboy with black high heels jerks off till cumshot on belly

Categories: amateur, asian, belly, black, cumshot, high heels, ladyboy, masturbation, solo, teen (18+)

XXXDan

Latex bodysuit, anal fucking machine, anal spreading, ping pong, penis pump

Categories: amateur, anal, bdsm, big cock, bondage, crossdressing, danish, dick, dildo, european

aShemaleTube

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

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

XXXDan

Gangster loves tranny Marika Ferreira

Categories: amateur, anal, beauty, big ass, big cock, blonde, brazilian, creampie, crossdressing, cumshot

TrannyOne

Beautiful Chinese Shemale in Pantyhose get Feet Suck and Fucked

Categories: amateur, anal, anus, asian, ass, beauty, bed sex, bedroom, brunette, chinese

KeekAss

Mesmerizing ladyboy pulling her big cock and making it jizz

Categories: anal, asian, big cock, big tits, cumshot, fetish, high heels, jizz, ladyboy, masturbation

Pornstars: Venus Lux

JizzBunker

Kellystar518 - Pink Punk Teaser

Categories: amateur, big ass, big cock, cosplay, crossdressing, fetish, hardcore, high heels, hotel, italian

TrannyOne

Blonde tranny beauty fucks the horny guy's juicy ass on the bed

Categories: anal, anus, ass, assfingering, babe, beauty, bed sex, bedroom, blonde, blowjob

Pornstars: Kelly Klass

aShemaleTube

Sexy Crossdresser kellycd2022 in shiny gold dress pantyhose and heels

Categories: amateur, big tits, crossdressing, dress, fetish, high heels, ladyboy, masturbation, mature, outdoor

PornGem

TS babes have their assholes hammered with toys and cocks

Categories: 3some, anal, ass, babe, big cock, big tits, blowjob, cumshot, dick, high heels

Pornstars: Aubrey Kate

TrannyOne

Come and Swing My Way

Categories: anal, anus, ass, ball licking, balls, bed sex, bedroom, big tits, blowjob, brunette

aShemaleTube

Sissythai fucking bbc dilldo until her ahegao eye

Categories: amateur, asian, big ass, big black cock, black, crossdressing, dick, dildo, femboy, hardcore

XXXDan

Natasha Rotten: provocation with her feet

Categories: amateur, arab, bdsm, blowjob, bondage, brazilian, crossdressing, cumshot, feet, fetish

aShemaleTube

Holly's got a bulge in her skirt at the cruising area

Categories: amateur, british, crossdressing, cruising, hd, high heels, homevideo, mature, outdoor, public

XXXDan

Fucking with another big black dildo and cumming stroking my hard cock

Categories: amateur, anal, big cock, black, crossdressing, cum, cumshot, dick, dildo, european

JizzBunker

Crossdresser teases in shiny leggings and heels

Categories: amateur, crossdressing, german, high heels, latex, leggings, spanking, tease, teen (18+)

TrannyOne

Busty TS MILF plows the guy's thick ass with her huge Tcock

Categories: anal, anus, asian, ass, bdsm, bed sex, bedroom, belly, big tits, blowjob

aShemaleTube

Sissy Francis training for daddies

Categories: amateur, anal, big ass, crossdressing, daddies, fetish, hd, high heels, homevideo, mature

JizzBunker

Kellystar518 - Kellys Penthouse Show

Categories: anal, big ass, big cock, bikini, black, cosplay, crossdressing, dildo, fetish, high heels

TrannyOne

Lovely lad fulfills the TS babe's feet fetish before sucking and riding her thick cock

Categories: 69, anal, anus, ass, babe, bed sex, bedroom, blonde, couple, cum

aShemaleTube

Brunette asian ladyboy with high heels gets oral sex from her man in bed

Categories: amateur, asian, bed sex, brunette, cumshot, high heels, ladyboy, oral, teen (18+)

KeekAss

Bald stud fucks sensual brunette shemale up her lil asshole

Categories: anal, ass, big cock, big tits, blowjob, brunette, cumshot, fetish, fishnet, hairless

XXXDan

Leilani Li goes into the pool in a bikini and heels to seduce the attractive lifeguard Kenzo Alvarez - TRANS ANGELS

Categories: big cock, big tits, bikini, high heels, latina, pool, pornstar, seduce, transsexual

Pornstars: Leilani Li

KeekAss

2 SHE-CREATURES HAVING JOY TOGETHER

Categories: anal, assfucking, big ass, big cock, big tits, blonde, blowjob, brunette, cumshot, deep throat

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

JizzBunker

Nancy in pink satin transvestite milf

Categories: amateur, arab, beauty, big cock, boots, crossdressing, fetish, high heels, lingerie, masturbation

TrannyOne

Crossdresser Sissy in High heels fucked by chubby daddy

Categories: amateur, anal, anus, ass, chubby, couple, crossdressing, cum, daddies, dick

KeekAss

TranssexualNetwork.com - Cute ladyboy's BF cock rubbing with ass and hands

Categories: asian, ass, big cock, big tits, blonde, blowjob, boyfriend, cumshot, cute, dick

JizzBunker

Legs in wetlook

Categories: amateur, bdsm, big ass, crossdressing, dutch, fetish, handjob, high heels, latex, legs

aShemaleTube

Untidy Sissi Stacy Fingering and Fist Here Ass by Interesting Toy

Categories: amateur, anal, anal toying, ass, big ass, crossdressing, cute, dildo, dirty talk, fingering

JizzBunker

Black Satin Lingerie, High Heels and Sensual Cum

Categories: amateur, beauty, big ass, big cock, black, brazilian, crossdressing, cum, cumshot, cute

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

KeekAss

Erotic Asian shemale sinking buxom darling wet pussy

Categories: asian, babe, big cock, big tits, blowjob, brunette, buxom, cowgirl, cumshot, deep throat

ShemaleMovie

Crossdresser lingerie and heels, teenage

Categories: anal, asian, babe, beauty, brutal, crossdressing, cum, high heels, jizz, ladyboy

XXXDan

I eat my cum and I like to swallow it all

Categories: amateur, big cock, big tits, blonde, cum swallowing, cumshot, cute, handjob, high heels, masturbation

KeekAss

Trendy tgirl ultra-cutie milking her stiffy solo

Categories: amateur, ass, beauty, booty, brunette, close up, cute, handjob, hd, high heels

aShemaleTube

Gio trav loves black cocks

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

JizzBunker

Kellystar518 in the movie Stepmom Rides the BBC

Categories: anal, big ass, big black cock, big cock, black, crossdressing, cumshot, dildo, gay, gym

KeekAss

BORN TO BE T-MODEL COCKSLUT

Categories: big ass, big cock, blonde, blowjob, brazilian, dick, dominatrix, gay, handjob, hd

aShemaleTube

Going Out During the Day! Part Iii

Categories: amateur, beauty, big ass, big cock, big tits, compilation, crossdressing, cum, fishnet, high heels

XXXDan

TS pornstar Marika Ferreira gets fucked in sexy lingerie and heels and gets cum in her ass

Categories: amateur, anal, ass, beauty, big ass, big cock, blonde, brazilian, crossdressing, cum

aShemaleTube

👀Show off a Beautiful Little Brothel Whore in Mini-Skirt, Latex & Nylon Stockings, Black Stiletto

Categories: amateur, beauty, black, crossdressing, european, fetish, high heels, latex, miniskirt, nylon

XXXDan

Brunette ladyboy in high heels gets fucked doggy style on

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

KeekAss

Sultry TS Venus Lux pours her jizz on Charity Bangs juicy tits

Categories: babe, big cock, big tits, blowjob, cowgirl, cum, cumshot, deep throat, dick, fetish

Pornstars: Charity Bangs, Venus Lux

aShemaleTube

Small tits tranny Fabiana Abelha gets fucked with her high heels on

Categories: anal, big ass, big cock, big tits, blowjob, cumshot, high heels, latina, pornstar, pov

Pornstars: Fabiana

XXXDan

Dominatrix fucks goth transvestite

Categories: amateur, anal, bdsm, bondage, crossdressing, dominatrix, fetish, goth, hardcore, high heels

KeekAss

Trans Dancer Barbara Perez Pummels Her Customers Backside in Stocking and Stilettos

Categories: anal, big tits, black, blowjob, dancing, doggystyle, fake tits, gay, handjob, hd

aShemaleTube

high heels and big tits latina tattooed tgirl toys ass and tugs cock on cam

Categories: amateur, ass, big tits, cute, dick, high heels, homevideo, latina, masturbation, slim

XXXDan

Cute Latina in red heels sucks a big cock and gets fucked hard

Categories: amateur, anal, big ass, big clit, big cock, black, creampie, crossdressing, cumshot, cute

KeekAss

Trans Carla Brasil banging sizzling dude from Queensland.

Categories: amateur, anal, banging, big ass, blowjob, brazilian, brunette, gay, hd, high heels

JizzBunker

Latina shemale in high heels gets fucked bareback in

Categories: amateur, anal, barebacking, big ass, big cock, big tits, blowjob, brazilian, creampie, gay

KeekAss

transgender princess diamond wet rail

Categories: anal, asian, ass to mouth, big cock, blowjob, brunette, close up, gaping hole, gay, hardcore

Pornstars: Diamond Princess

aShemaleTube

Pink Best Moments of Gisa - Part 2

Categories: ass, beauty, big tits, blonde, cute, hd, high heels, mexican, outdoor, public

JizzBunker

Lumina Outdoor Bryggelen

Categories: amateur, anal, bdsm, blowjob, dutch, gangbang, gay, hardcore, high heels, lingerie

aShemaleTube

Shemale Laiza Lavier dangles that humongous cock around

Categories: ass, dick, hd, high heels, monster cock, posing, striptease, tattoo, wanking

ShemaleMovie

Joselynne Crossdresser gets drilled with my toys in the second part

Categories: amateur, anal, anal toying, bdsm, big cock, crossdressing, dildo, domination, drilling, high heels

XXXDan

Small tits ladyboy in high heels gets her small cock

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

KeekAss

Glamcore ladyboy thanks superhero with her butt

Categories: anal, ass, assfucking, big ass, big cock, big tits, bizarre, blowjob, brunette, close up

ShemaleMovie

Heelex in flip flops and latex enjoying an outdoor adventure

Categories: amateur, crossdressing, european, feet, femboy, high heels, ladyboy, latex, outdoor, sissy

KeekAss

Classy Asian tgirl cums on high heels after masturbation

Categories: asian, big cock, big tits, brunette, cum, cumshot, fetish, hd, high heels, ladyboy

aShemaleTube

Cute Blonde Teen Trap In Heels Stroking

Categories: amateur, blonde, cute, high heels, homevideo, masturbation, small tits, solo, stroking, teen (18+)

aShemaleTube

Fucking Goth Sissy Jade Madison - Compilation 1

Categories: amateur, american, anal, beauty, compilation, crossdressing, femboy, goth, high heels, lingerie

KeekAss

Adorable shemale with a sexy body sucks dick and barebacked

Categories: adorable, anal, barebacking, blowjob, brunette, cumshot, dick, hd, high heels, lingerie

KeekAss

Wonderful shemale wanks tauntingly - Stellar Softcore

Categories: amateur, asian, brunette, glamour, gorgeous, handjob, hd, high heels, ladyboy, leather

KeekAss

TranssexualNetwork.com - Brown shemale's intense orgasm from self wanking

Categories: big cock, big tits, cumshot, high heels, masturbation, orgasm, solo, tranny, transsexual, wanking

aShemaleTube

Princess Bunnie: Cumming in my Sparkly Dress

Categories: crossdressing, cum, dress, hd, high heels, masturbation, mature, model, sissy, slut

KeekAss

Enjoy to Deep-Throat and Swallow Spunk

Categories: amateur, blonde, crossdressing, cum, cum swallowing, cumshot, deep throat, dildo, ebony, handjob