Sissy Shemale Videos » 23

aShemaleTube

Indian sissy porn star slut Manusha with a stranger in the hotel room

Categories: amateur, asian, ass to mouth, big ass, big cock, crossdressing, cum in mouth, cumshot, hd, homevideo

KeekAss

HOTPLAY SILKS

Categories: amateur, crossdressing, fetish, hd, homevideo, lingerie, masturbation, satin, sissy, small tits

KeekAss

Boy Fucks Shemale

Categories: amateur, ass to mouth, blowjob, boy, brunette, dildo, fantasy, handjob, homevideo, masturbation

TrannyOne

TRANS NYLON EROTICA V3

Categories: anal, anus, ass, big cock, compilation, dick, erotic, lingerie, masturbation, mature

aShemaleTube

Sissy anal sex

Categories: anal, anal toying, blonde, hd, sissy, transsexual

aShemaleTube

Milk Machine

Categories: amateur, compilation, crossdressing, cum, cumshot, fetish, fucking machine, hd, huge cock, ladyboy

aShemaleTube

Hot Mamá Trans Se Folla a un Femboy

Categories: asian, femboy, femdom, feminization, hd, sissy, slave, teen (18+), tgirl, transsexual

KeekAss

Elegant Looking Shemale Show Her Body Bare

Categories: amateur, ass, beauty, handjob, homevideo, jerking, lingerie, masturbation, nurse, redhead

HDSex

Stretching and expanding cornhole with a tunnel speculum - Part 2

Categories: anal toying, sissy, speculum

KeekAss

domme roleplay i poke u rock-hard like my tiny sissy plaything and jism deep inwards you

Categories: amateur, big cock, close up, cum, cumshot, dick, dirty talk, domination, huge cock, joi

TrannyOne

Good-looking golden-haired maried transsexual Sasha deSade in stockings

Categories: ass, bdsm, bimbo, blonde, booty, bride, cosplay, costume, crossdressing, hd

aShemaleTube

Spidewoman in sheer bikini jerking off

Categories: amateur, anal, big ass, big cock, big tits, bikini, creampie, homevideo, jerking, masturbation

aShemaleTube

Princess Pea JOI GOON with Mummy

Categories: big cock, british, dick, domination, fetish, hd, humiliation, joi, mature, model

aShemaleTube

Sissy boy feminization with hard daddy suck and fuck

Categories: amateur, anal, asian, big cock, big tits, boy, crossdressing, cumshot, daddies, femboy

Pornstars: Viper

aShemaleTube

trap Bea

Categories: ass, barebacking, brunette, buttplug, cage, femboy, fingering, homevideo, lingerie, sissy

KeekAss

ABDL Nappy Sissy Tugging Off in a Cushion

Categories: amateur, crossdressing, cum, diaper, femboy, high heels, humping, jerking, ladyboy, lingerie

aShemaleTube

Arabic Tranny Mikah Hotel Blowjob

Categories: amateur, arab, blowjob, crossdressing, doll, hd, homevideo, hotel, interracial, pov

KeekAss

Addicted To Sissies - Mental Domination PMV

Categories: anal, brunette, compilation, domination, girlfriend, hd, joi, sissy, stockings

ShemaleMovie

Unprotected fun after the soccer match with stunning Veronica Sanders

Categories: anal, asian, babe, beauty, big cock, cowgirl, funny, ladyboy, riding, sissy

aShemaleTube

Two Sissys having Fun together - Part 2: Fucking

Categories: amateur, anal, crossdressing, femboy, funny, hd, homevideo, lesbian, lingerie, sissy

aShemaleTube

Taiwan sissy yahui anal fuck in public toilet

Categories: anal, hd, model, public, sissy, taiwanese, toilet, transsexual

KeekAss

Busty Shemale Strokes Her Big Cock On Cam

Categories: amateur, beauty, big cock, big tits, boyfriend, crossdressing, femboy, homevideo, lingerie, masturbation

aShemaleTube

Sissy cartoon

Categories: cartoon, hd, sissy

KeekAss

trans dame gets rode by even LARGER Hankey's Playthings XXXCALIBUR with poke machine

Categories: amateur, anal, anal toying, ass, crossdressing, dildo, femboy, hd, huge dildo, ladyboy

aShemaleTube

Pink haired ts impales her sissy date

Categories: amateur, anal, big ass, domination, hardcore, hd, homevideo, sissy, tranny, transsexual

aShemaleTube

Blonde in a hot pink bodystocking

Categories: blonde, bodystocking, crossdressing, femboy, fetish, hd, ladyboy, lingerie, masturbation, pantyhose

ShemaleMovie

Tgirl Riley enjoys raw fucking in meeting #6 PartII

Categories: amateur, anal, barebacking, big cock, crossdressing, dick, european, femboy, gaping hole, lingerie

KeekAss

Latina Tgirl Deepthroats Dildo

Categories: amateur, blowjob, crossdressing, deep throat, dildo, homevideo, jerking, latina, masturbation, old

KeekAss

Ginormous meatpipe crossdresser Lucy jacking and nutting in the shower

Categories: amateur, bathroom, big cock, big tits, crossdressing, cumshot, dick, fake tits, fetish, hd

aShemaleTube

Slave bitch used by two CD mistresses

Categories: anal, bitch, crossdressing, domination, hd, mature, mistress, nipples, sissy, slave

aShemaleTube

Sissy Haylee's Cum Walking and Flashing Huge Boobs in Public part 1

Categories: amateur, asian, big tits, crossdressing, cum, cum in mouth, flashing, hd, huge tits, outdoor

aShemaleTube

Femboy Tease

Categories: amateur, cumshot, femboy, fetish, hd, masturbation, sissy, tease, webcam

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

aShemaleTube

Pantyluvn sissy pov love at first sight

Categories: amateur, crossdressing, cumshot, femboy, homevideo, lingerie, masturbation, mature, pov, sissy

KeekAss

Pretty Hot Shemale Strips

Categories: amateur, anal, beauty, big cock, femboy, homevideo, interracial, jail, japanese, ladyboy

KeekAss

Crossdresser juvia jolie offers her monstrous Booty for a from the rear screw

Categories: amateur, anal, ass, bbw, big ass, big cock, bitch, booty, crossdressing, doggystyle

ShemaleZ

Nely Sissy Culona Big Balls Bitch Self Cum Tranny Shemale

Categories: amateur, balls, big ass, bitch, cum, hd, ladyboy, latina, lingerie, sissy

KeekAss

She-male in Banana Pajamas Being Ravaged by a Black Boy Sans a Protection

Categories: amateur, anal, ass, ball busting, banana, barebacking, big ass, big black cock, big cock, black

aShemaleTube

Pantyluvn sissy a gurl like that

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

JizzBunker

Big Ass Booty House Femboy Lovely Cute Amateur Sexy Slut Model Crossdresser Sissy Kitty With Her Handmade Raw Videos

Categories: amateur, bbw, beauty, big ass, big cock, booty, college, crossdressing, cute, femboy

aShemaleTube

Femdom Mistress fucks Sissy slut ass, Chastity Punishment 🔐 @Sasha_de_Sade & Saskia_de_Sade

Categories: ass, femdom, feminization, hd, homevideo, mistress, model, punishment, sissy, slut

KeekAss

Sissy Smashed Lovemaking Machine

Categories: amateur, anal, ass, big ass, big tits, booty, crossdressing, cum, dildo, hd

aShemaleTube

Sissy Crossdresser locking up her clitty

Categories: amateur, buttplug, cage, corset, crossdressing, hd, high heels, homevideo, sissy, stockings

aShemaleTube

🔥Sexy Blonde babe🔥 Tiffany Kitten fucks her ass with BBC dildo

Categories: amateur, anal, ass, babe, big black cock, big cock, blonde, crossdressing, dildo, femboy

aShemaleTube

Sissy Anna playing with Dildo and stroking her Sissyclit

Categories: amateur, anal, ass, clit, crossdressing, dick, dildo, femboy, hd, lingerie

KeekAss

Jism While Showcasing my soles - Veronica Sanders

Categories: anal, crossdressing, cum, cumshot, dildo, feet, femboy, handjob, hd, jerking

JizzBunker

Fat Sissy cums in inverted cage after 3 weeks of chastity

Categories: bbw, cage, cum, fat, milf, sissy

KeekAss

Scorching Ash-Blonde She-Creature In Public Marvelous Clothed Super-Cute Femboy

Categories: amateur, babe, big ass, big cock, blonde, booty, clothed sex, college, cosplay, crossdressing

KeekAss

Leather Micro-Skirt & leopard print for whorish Sarah

Categories: amateur, big tits, british, crossdressing, dick, handjob, hd, homevideo, leather, lingerie

TrannyOne

Sissy slave guy luvs sucking that black dick

Categories: amateur, bdsm, black, blowjob, dick, domination, ebony, fetish, hd, homevideo

aShemaleTube

Gorgeous Femboy FapGirl Pounding Her Hard Dick

Categories: dick, femboy, gorgeous, hd, jerking, lace, lingerie, moaning, sissy, stroking

aShemaleTube

Sissy Anna getting fucked by Daddy

Categories: amateur, anal, cage, daddies, femboy, hd, homevideo, hotel, sissy

aShemaleTube

Stay Healthy

Categories: barebacking, crossdressing, cucumber, femboy, hd, homevideo, lingerie, sissy, small cock, stockings

aShemaleTube

Sexy Nurse Sandy a BBC balls deep

Categories: amateur, ass to mouth, balls, big black cock, big cock, blonde, crossdressing, hd, homevideo, lingerie

KeekAss

Onlyfans Daralux POINT OF VIEW boink sissy crossdresser

Categories: asian, assfucking, blowjob, cosplay, crossdressing, femboy, handjob, hd, ladyboy, maid

aShemaleTube

dany_monster_cock

Categories: big cock, brunette, dick, hd, homevideo, latina, lingerie, long hair, masturbation, sissy

aShemaleTube

Ms. Pink Prolapse Model

Categories: amateur, anal, asian, chinese, crossdressing, femboy, model, prolapse, sissy, small tits

aShemaleTube

Syd the Witch Compilation

Categories: amateur, big ass, big cock, compilation, crossdressing, cumshot, femboy, fetish, hd, masturbation

ShemaleMovie

Dominance and submission with anal action featuring Pixie Catgurl

Categories: american, anal, bdsm, beauty, compilation, crossdressing, domination, indian, ladyboy, lingerie

KeekAss

Hot Tgirl Grasps Her Dick To Masturbate

Categories: amateur, anal, beauty, chubby, condom, cute, dick, femboy, homevideo, innocent

KeekAss

She-Creature getting mischievous in the douche Railing that Pink Cigar

Categories: amateur, anal, beauty, big black cock, big cock, boy, cigarette, femboy, homevideo, old

aShemaleTube

on my high heels ride huge pink dildo and get so much precum

Categories: amateur, big cock, cumshot, dildo, hd, high heels, huge dildo, lingerie, model, sissy

aShemaleTube

ts solo cumming

Categories: amateur, big cock, blonde, creampie, cum, cumshot, homevideo, masturbation, sissy, solo

aShemaleTube

Mirror Kisses And Dildo Play - S019.1

Categories: amateur, asian, blowjob, crossdressing, dildo, femboy, fetish, hd, homevideo, kissing

KeekAss

MF CHEW THIS BUM

Categories: amateur, anal, ass, asslick, ball licking, big ass, big black cock, black, booty, dick

XXXDan

Sissy training - Dildo and electric chastity cum

Categories: cum, dildo, electrified, sissy

KeekAss

Spidergirl Gwen Stacy's Immense Internal Cumshot, Spunking Her Web of Jizm Everywhere

Categories: amateur, anal, big cock, blonde, cosplay, creampie, crossdressing, cum, cumshot, feminization

aShemaleTube

Sissy Limp Clit fills it's Cunt Hole

Categories: clit, crossdressing, cunt, fetish, hd, latex, masturbation, mature, sissy, solo

ShemaleMovie

Ash-blonde transgender princess Yourprettykate rides a dildo until she cums

Categories: beauty, blonde, cum, dildo, femboy, jizz, riding, sissy, stockings, toys

aShemaleTube

Sizzling POV Cum Session.

Categories: bbw, black, crossdressing, cum, cumshot, ebony, fat, ladyboy, lingerie, masturbation

XXXDan

Amazing sissy anal ride on BBC

Categories: amateur, amazing, anal, big black cock, big cock, black, dildo, european, french, hardcore

aShemaleTube

Cali Colombia

Categories: barebacking, brunette, colombian, cumshot, dildo, glasses, hd, homevideo, latina, lingerie

HDSex

Punished guy transformed into a gorgeous babe gives an arousing footjob

Categories: babe, feet, footjob, gorgeous, punishment, sissy

KeekAss

Outstanding rump cougar she-creature

Categories: amateur, anal, assfucking, big ass, bimbo, cougar, dildo, hd, mature, milf

VideoSection

Trans princess Gigi From La transforms you into an ass-eating, cock-sucking super goddess

Categories: ass, black, cum, dick, goddess, jizz, pantyhose, sissy, transsexual

aShemaleTube

Vanniall Self Facial Full Cam Show - Trans Jerk off in Lingerie, Cum on Glasses, Panty Bulge Cock

Categories: big ass, big black cock, black, cum, cumshot, dick, facial, glasses, hd, jerking

aShemaleTube

Ezra_Kyle25 shows new pink thong in a sexy video

Categories: amateur, big ass, big cock, crossdressing, ebony, femboy, fetish, hd, homevideo, ladyboy

ShemaleZ

Cammy White In Sissy Edges While Chained

Categories: amateur, american, bdsm, blonde, chained, hd, sissy, solo, teen (18+), webcam

KeekAss

Ass-Fuck Hike and Abjection for TRANSSEXUAL Marionette Loren Aprile

Categories: abuse, amateur, anal, anal toying, assfucking, bdsm, crossdressing, dick, domination, femdom

aShemaleTube

A Touch Of Femboy - TS PMV

Categories: 3some, amateur, anal, big cock, blowjob, compilation, femboy, hd, sissy, teen (18+)

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

KeekAss

Finger-banging And Poking Her Lil Fuckhole Makes Her Jizz RIGID 4K

Categories: amateur, cage, cum, cumshot, fingering, handjob, hd, jizz, masturbation, orgasm

aShemaleTube

Teasing Blonde Sissy in Fishnet Bodysuit

Categories: amateur, blonde, fishnet, homevideo, masturbation, pornstar, sissy, solo, tease, teen (18+)

Pornstars: Domino

KeekAss

Glorious mature she-male with a caboose speculum so stunning

Categories: amateur, anal, ass, big ass, crossdressing, cumshot, dildo, hd, masturbation, mature

aShemaleTube

Hot Load of Semen Just for You Step Daddy

Categories: amateur, asian, cum in mouth, cumshot, daddies, femboy, fetish, hd, lingerie, model

Pornstars: Viper

aShemaleTube

Blue minidress and black stockings

Categories: black, blonde, crossdressing, dress, femboy, hd, ladyboy, lingerie, pantyhose, pov

aShemaleTube

Emma

Categories: anal, big cock, big tits, blonde, blowjob, cum in mouth, femboy, hd, homevideo, ladyboy

aShemaleTube

Tgirl Sucks Juicy Cock

Categories: blonde, blowjob, cum in mouth, dick, femboy, hd, homevideo, juicy, sissy, stockings

aShemaleTube

BBC dildos give her caged sissygasms

Categories: anal, big ass, big black cock, cumshot, dildo, femboy, hd, orgasm, prostate, sissy

KeekAss

Punk Sissy Frolicking & Sissygasm Dual Fuck Stick

Categories: amateur, anal, blonde, crossdressing, cumshot, cute, dildo, emo, femboy, goth

aShemaleTube

Nude

Categories: amateur, anal, big cock, creampie, hd, japanese, masturbation, nude, sissy, solo

aShemaleTube

The Slut-O-Lympic Games

Categories: anal, bdsm, dildo, fetish, game, hd, model, riding, sissy, slut

aShemaleTube

How To Train A White Sissy

Categories: blonde, crossdressing, domination, femboy, ladyboy, sissy, teen (18+), train, white

aShemaleTube

Razor Burnt Ass

Categories: amateur, anal, ass, blowjob, crossdressing, cumshot, femboy, hd, homevideo, interracial

KeekAss

Fat fake penis plow machine raunchy ass fucking sesh

Categories: amateur, anal, assfucking, crossdressing, dick, fat, femboy, hardcore, hd, raunchy

aShemaleTube

Birthday Sex

Categories: barebacking, birthday, blonde, blowjob, crossdressing, cum in mouth, hd, homevideo, lingerie, mature

PornoXO

Sissy in shiny bodystocking Using Fuck Machine - R..a..c..h..a..e..l B..e..l..l..e

Categories: bodystocking, cage, fetish, hd, humiliation, masturbation, pantyhose, sissy, solo, squirt

aShemaleTube

CD Bride With Throbbing Butt Plug Masturbates to Sexy CD

Categories: big cock, big tits, bride, buttplug, crossdressing, cumshot, hd, lingerie, masturbation, sissy

KeekAss

Domme sfonda il ass e la sissy ha orgasmi multipli, gode come una vera vacca troia

Categories: amateur, anal, ass, creampie, crossdressing, cumshot, domination, femboy, femdom, fetish

aShemaleTube

Ebony Sissy Cumming on Toes

Categories: crossdressing, cum, ebony, feet, femboy, hd, lingerie, pretty, sissy, toes

KeekAss

UBER-SEXY INEXPERIENCED SUNTANNED FLESH T-MODEL AND HER SISSY!

Categories: amateur, asian, ass, babe, big ass, big tits, blowjob, cumshot, fetish, filipina

KeekAss

So sizzling in crimson

Categories: amateur, beauty, big ass, big cock, crossdressing, cum, cumshot, cute, feet, german

aShemaleTube

Femboy Lexi Faith sexy pantyhose, footjob, cumshot

Categories: anal, asian, chinese, cumshot, femboy, footjob, hd, ladyboy, masturbation, pantyhose

Pornstars: Sexy Faith

aShemaleTube

Summer dress, black pantyhose and high heels

Categories: amateur, black, blonde, crossdressing, dress, femboy, hd, high heels, homevideo, ladyboy

KeekAss

5 of My Most Super-naughty, Bad, Girly TOMBOY Nymph with a Pipe MEATY Cum-shots in Latex NYLON

Categories: amateur, bikini, bukkake, compilation, cosplay, crossdressing, cumshot, cute, dick, femboy

KeekAss

Big Dick Crossdresser Jerking

Categories: amateur, beauty, big cock, crossdressing, cute, friend, homevideo, irish, jerking, masturbation

KeekAss

Sissy Alexas makes butt twat spreading exercises in purity 1 of two

Categories: amateur, anal, anal toying, ass, big tits, bimbo, blonde, crossdressing, cunt, fetish

aShemaleTube

Vacation Fun

Categories: crossdressing, cute, funny, hd, sissy, skinny, solo, tease, vacation

KeekAss

NASTY STUDS CUCKOLD ON THEIR WIVES WITH SISSY LIGHT-HAIRED ALEXIA ST JAMES

Categories: amateur, anal, ass, blonde, blowjob, creampie, crossdressing, cuckold, cum, daddies

aShemaleTube

Tattoo daddy fucks CD Melisa Doll

Categories: amateur, anal, daddies, doll, femboy, homevideo, ladyboy, sissy, small tits, tattoo

aShemaleTube

sofieanálková

Categories: crossdressing, femboy, futanari, ladyboy, sissy, solo, tranny

FetishPapa

Red dress gown crossdresser feminization

Categories: big tits, crossdressing, doll, dress, fake tits, feminization, hd, mask, mature, queen

aShemaleTube

dizzy bound and disciplined by Mistress

Categories: bdsm, bondage, bound, femdom, hd, mistress, sissy, submissive, tranny

aShemaleTube

The Dancing (SHEMALE) Queens (Part II)

Categories: asian, big cock, compilation, dancing, hd, homevideo, ladyboy, latina, masturbation, sissy

aShemaleTube

Cum Whore

Categories: amateur, crossdressing, cum, hd, pantyhose, sissy, slut, solo

aShemaleTube

Huge Dildo Stretch My Anal to Cumshot

Categories: anal, asian, chinese, cumshot, femboy, hd, huge dildo, ladyboy, lingerie, masturbation

JizzBunker

Leather Sissy Boots

Categories: boots, leather, sissy

aShemaleTube

CD Becky and her mistress

Categories: big tits, cumshot, glasses, handjob, hd, high heels, homevideo, lingerie, masturbation, mistress

KeekAss

Transvestiten, Transe, Electro-Hitachi, Restrain Bondage

Categories: amateur, bdsm, big cock, blonde, bondage, bound, crossdressing, domination, feminization, fetish

aShemaleTube

sissy feet 9

Categories: amateur, big cock, cumshot, feet, femboy, hd, homevideo, ladyboy, pov, sissy