Sissy Shemale Videos » 50

xHamster

Sex Show Gigi and Dave, Webcam POV, Shemale and Man 2025-04-27 P9

Categories: amateur, anal, ass, barebacking, beach, big ass, blowjob, british, couple, creampie

aShemaleTube

Dizzy sucks another cock under Mistress's instruction

Categories: blowjob, crossdressing, dick, femdom, hd, lingerie, mistress, oral, sissy, stockings

xHamster

She likes my big cock in her ass very much

Categories: amateur, ass, big cock, compilation, cosplay, desi, hd, homevideo, ladyboy, sissy

xHamster

Sissy Sperma trinken

Categories: bdsm, compilation, creampie, cum, cum in mouth, cum swallowing, facial, fat, feminization, fetish

xHamster

Transgender on sexy Puma one piece swimsuit

Categories: blonde, crossdressing, cum, feminization, fetish, hd, latex, lingerie, sissy, stockings

HDSex

Self fisting, sissy gape, shemale anal fisting

Categories: anal fisting, anal toying, fisting, gaping hole, sissy

KeekAss

Denise Humain Random Compilation One

Categories: amateur, anal, anal toying, bdsm, blowjob, brunette, compilation, crossdressing, cum, deep throat

KeekAss

Sexy Young Crossdresser

Categories: beauty, black, brunette, crossdressing, cute, denial, homevideo, interracial, masturbation, sissy

aShemaleTube

TS 425

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

KeekAss

Drain Your Sack

Categories: anal, cum, cumshot, edging, femboy, fetish, hd, joi, masturbation, sissy

xHamster

Sissi Stacy Plays with Cristal Clear Three Inches Diameter Dildo

Categories: amateur, anal, ass, big ass, big cock, crossdressing, cute, dick, dildo, doggystyle

xHamster

Argentinian guy humiliating Colombian Slut

Categories: abuse, amateur, argentinian, balls, beauty, blowjob, brunette, colombian, cum, cumshot

xHamster

Glam dildo bitch

Categories: bitch, canadian, crossdressing, dildo, fetish, gay, lingerie, riding, sissy, spandex

KeekAss

Sissy railing fake penis

Categories: amateur, anal, beauty, crossdressing, dick, dildo, fishnet, hd, homevideo, ladyboy

aShemaleTube

Sissy Whore Anal Adore

Categories: anal, ass, extreme, gaping hole, hd, insertion, sissy, slut, toys

ShemaleMovie

Ria Bentley's tgirl roommates tear it up in a messy extravaganza

Categories: 3some, american, anal, ass, babe, barebacking, beauty, big cock, creampie, cum

xHamster

Love to Pose

Categories: amateur, crossdressing, feet, fetish, glasses, hd, high heels, ladyboy, pretty, redhead

KeekAss

Pound my muddy culo in this stockings undergarments

Categories: amateur, anal, big ass, creampie, crossdressing, cute, femboy, hd, latina, mud

aShemaleTube

Dirty talking fem top Ella fucks toy & cums🍆💦

Categories: amateur, big cock, cum, cumshot, dirty talk, femboy, hd, masturbation, sissy, small tits

xHamster

Intriguing Intimacy: A Closer Look into My World

Categories: amateur, american, beauty, big ass, big cock, big tits, crossdressing, femdom, feminization, hd

aShemaleTube

sissy cock whore hypno

Categories: crossdressing, dick, feminization, gangbang, sissy, slut

KeekAss

Mischievous Sissy Assistant in Tights

Categories: amateur, crossdressing, fetish, hd, lingerie, pantyhose, pov, secretary, sissy

aShemaleTube

Beautiful young tgirl fucks her date in a hotel room

Categories: amateur, anal, asian, barebacking, beauty, big ass, big cock, big tits, domination, femboy

xHamster

Hot Sexy Party Dress Yummy Ladyboy Model Cosplayer

Categories: amateur, beauty, big tits, dancing, dress, femboy, first time, hd, ladyboy, massage

xHamster

I Want a Pizza Macho and a Big Sausage in My Room

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

aShemaleTube

MayaTsarina Dumb Bimbo Fuck Doll presents asshole and serves guys

Categories: ass, big ass, bimbo, doll, escort, femboy, hd, sissy, small cock, submissive

JizzBunker

Pretty sissy 69s Daddys face and takes his cock raw

Categories: 69, anal, black, blowjob, couple, daddies, dick, gay, hardcore, interracial

xHamster

Trans Jessica Moon Sucks Bailey Wilde's Cock

Categories: amateur, american, anal, big cock, blowjob, crossdressing, cum, dick, femboy, feminization

aShemaleTube

Cum in black and white

Categories: big cock, black, crossdressing, cum, cumshot, emo, femboy, futanari, hd, ladyboy

aShemaleTube

voluptuous american translady with tattoos tugs her cock

Categories: amateur, american, blonde, dick, feet, homevideo, jerking, legs, masturbation, sissy

xHamster

Sissy Rozebell - Tranny Love Black Dick Part2

Categories: amateur, black, compilation, dick, gay, hd, homevideo, sissy, tranny

aShemaleTube

Semen from the Asshole

Categories: ass, barebacking, cumshot, hd, homevideo, lingerie, sissy, sperm, toys

XXXDan

Sissy Onyx - Maid Play

Categories: amateur, anal, hardcore, lingerie, maid, masturbation, sissy, solo, teen (18+), toys

AlphaPorno

Shemale and her bitch play dirty games in very intense oral positions

Categories: bitch, bondage, brunette, dirty, fake tits, game, hd, legs, licking, milf

XXXDan

Fucking My Sissy Ass and Cumming Like a Sissy Bitch

Categories: anal, ass, big ass, big cock, bitch, cum, cumshot, dildo, hardcore, masturbation

xHamster

The Guy Pushes His Dick Deep Into Sisi's Tight Ass

Categories: amateur, anal, ass, dick, european, hd, polish, sissy, tight

xHamster

Jakol muna ang inuuna ni reyna kay daddy og unya sex hard na pud kami

Categories: amateur, asian, beauty, big cock, cum, cumshot, daddies, filipina, hardcore, hd

KeekAss

Sissylucylove edging inwards fleshlight

Categories: amateur, crossdressing, edging, femboy, feminization, fleshlight, handjob, hd, homevideo, masturbation

aShemaleTube

Extreme sissy training

Categories: big cock, extreme, fetish, homevideo, huge dildo, latex, prolapse, sissy, toys

xHamster

Cute Asian Sissy Masturbate and Cum in 4k

Categories: amateur, asian, cum, cute, hd, ladyboy, masturbation, sissy, solo, stockings

aShemaleTube

Obey, Serve, Repeat - My Sissy Maid’s New Routine POV Now Hiring!!!

Categories: big cock, big tits, crossdressing, domination, fetish, hd, latex, lingerie, maid, pornstar

Pornstars: Viper

xHamster

Latina submissive tranny with slutty ears.

Categories: amateur, cute, femboy, fetish, hd, ladyboy, latina, lingerie, masturbation, mexican

xHamster

Trans Christmas Sissy Elf Milked by Fucking Machine With Huge Dildo! - Jessica Bloom

Categories: amateur, anal, beauty, blonde, british, cosplay, crossdressing, femboy, fucking machine, hd

aShemaleTube

Really Cute CD & Her Fleshlight

Categories: crossdressing, cute, femboy, fleshlight, hd, lingerie, sissy, small tits, solo, stockings

xHamster

public crossdressing - sexy platform thongs and latex leggings

Categories: amateur, crossdressing, european, hd, high heels, latex, leggings, lingerie, outdoor, polish

xHamster

Love for Webcam Modeling: Expressing Confidence and Sensuality

Categories: 3some, amateur, american, beauty, big ass, big cock, crossdressing, femdom, feminization, hd

xHamster

Camelia Fucking machine Dildo session with anal gape

Categories: amateur, anal, ass, beauty, big ass, blonde, dildo, feet, fetish, french

Pornstars: Camelia

KeekAss

The superslut bellows from a rock-hard fuck stick in the bootie three

Categories: amateur, anal, ass, assfucking, big ass, big black cock, crossdressing, dildo, feet, femboy

aShemaleTube

(1)The🎀pink maid takes a break while her employer is away. Encager & Plugger. CAM VanessaBarBie Van

Categories: amateur, anal toying, babysitter, beauty, big cock, cosplay, crossdressing, escort, fishnet, french

xHamster

Trixy and the worker short version

Categories: amateur, anal, barebacking, bdsm, beauty, big cock, blowjob, crossdressing, cum, cumshot

xHamster

Jenna cums in your face in high heels

Categories: british, cum, dick, hd, high heels, ladyboy, lingerie, long nails, masturbation, pov

JizzBunker

Sissy crossdresser Amber blowjob at bus party

Categories: blowjob, bus, crossdressing, party, sissy

xHamster

The Only Way Sissys Must Cum, Try

Categories: amateur, anal, big ass, cum, dildo, fucking machine, hd, masturbation, mature, pussy

xHamster

Hot Crossdresser from Polnad

Categories: amateur, crossdressing, escort, hd, homevideo, ladyboy, masturbation, polish, sissy, solo

xHamster

Forged3DX intense hard sex hot ganbang sweet big ass thirsty for cock swallowing double cum intense sex tasty thirsty buttocks

Categories: american, anal, ass, barebacking, big ass, bukkake, creampie, cum, cum swallowing, cumshot

ShemaleZ

Sissy Cd In Chastity Deep Fuck Huge Dildos Epic Handsfree Sissygasms Cleanup

Categories: amateur, blonde, hd, huge dildo, sissy, solo, toys

aShemaleTube

Dahlia Bloom @DahliaInBloom1

Categories: amateur, american, balls, big cock, blonde, booty, gorgeous, hd, pov, pretty

HClips

Huge 9in Dildo Fucking Compilation Vol.6 3 Min

Categories: amateur, anal, ass, assfucking, big ass, booty, booty shake, compilation, crossdressing, dildo

xHamster

sissy gape asshole

Categories: anal, anal toying, ass, big ass, gaping hole, hd, lingerie, masturbation, sissy, solo

VideoSection

Naughty crossdresser in lingerie performs on cam in a hot session

Categories: amateur, babe, beauty, big cock, compilation, crossdressing, cum, cumshot, fishnet, french

xHamster

On the noose without a rubber skirt

Categories: bdsm, european, fetish, german, hd, mature, rubber, sissy, skirt, small tits

xHamster

Chiara and her tail hole

Categories: anal, ass, barebacking, bbw, beauty, big ass, chubby, dick, fat, feet

aShemaleTube

Ezra_Kyle25 shows new pink thong in a sexy video

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

aShemaleTube

TS Mariaqt chastity fuck machine cum

Categories: amateur, anal, cage, compilation, cum, cumshot, fucking machine, hd, orgasm, sissy

KeekAss

Gorgeous Crossdresser Sissy Femboy

Categories: amateur, asian, beauty, blonde, crossdressing, cute, daddies, emo, femboy, gorgeous

KeekAss

Kitsy. Ankle and wrist suspension restrain bondage and rectal fuckfest. Seized bunny.

Categories: amateur, anal, ass, bdsm, beauty, bondage, bunny, crossdressing, cute, feet

aShemaleTube

Who can f... me pregnant?

Categories: amateur, crossdressing, femboy, hd, homevideo, sissy, solo, webcam

aShemaleTube

Blonde Crossdresser twerking in slow Motion

Categories: anal, ass, big tits, blonde, crossdressing, fishnet, hd, high heels, lingerie, sissy

xHamster

Marilyn Bad Gurl Smoking Fetish Cock Tease

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

ShemaleMovie

Amateur crossdresser, anal toy

Categories: amateur, anal, anal toying, bdsm, big black cock, big cock, compilation, crossdressing, dick, dildo

xHamster

Cumming in latex lingerie

Categories: amateur, compilation, crossdressing, cum, cumshot, femboy, fetish, hd, hungarian, latex

aShemaleTube

Teasing Blonde Sissy in Fishnet Bodysuit

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

Pornstars: Domino

xHamster

I am a streamer, This is CUM in PVT.

Categories: amateur, asian, bathroom, beauty, big cock, cosplay, crossdressing, cum, dancing, dildo

aShemaleTube

Butt Girl Has A Perfectly Round Peach Ass

Categories: ass, femboy, hd, huge dildo, model, pretty, sissy, thin, transsexual, white

aShemaleTube

[no porn] Japanese Pink Bunny Sissy image clips

Categories: amateur, asian, bunny, crossdressing, femboy, fetish, hd, homevideo, japanese, latex

aShemaleTube

Sissy Pussy gets Knotted

Categories: anal, ass, extreme, gaping hole, hd, insertion, pussy, sissy, toys

aShemaleTube

Indian Sissy Get Jerked

Categories: amateur, anal, crossdressing, cumshot, femboy, hd, indian, lingerie, sissy, small cock

xHamster

Compilation bottle fisting anal prolapse

Categories: amateur, anal, bdsm, bottle, boy, compilation, crossdressing, cum, fisting, gaping hole

aShemaleTube

HA69 Female doctors also have big cocks! Fuck the doctor like crazy!

Categories: anal, asian, big ass, big cock, chinese, crazy, crossdressing, cumshot, dildo, doctor

XXXDan

Fat juicy sissy slut

Categories: bbw, fat, juicy, sissy, slut

aShemaleTube

BBW TS Stokes Tiny Cock

Categories: bbw, big tits, blonde, masturbation, sissy, small cock, tiny dick, transsexual

xHamster

SISSY CUMSHOTS COMPILATION

Categories: amateur, compilation, couple, cum, cumshot, domination, english, hardcore, hd, homevideo

ShemaleZ

Sissy Bimbo Quinn Stone Plays Her Favorite Anal Trainer

Categories: amateur, anal, big ass, bimbo, hd, milf, redhead, sissy, solo, stockings

aShemaleTube

I am a faggot Hannah

Categories: amateur, crossdressing, hd, homevideo, sissy, small cock

xHamster

Best Student Crossdresser Show

Categories: amateur, anal, big cock, blowjob, couple, crossdressing, cumshot, dick, femboy, gay

xHamster

Shemale Bimbo Blonde Dumb Twerks With Her Fat Female Ass And Penetrates Her Anus With Her Dildo

Categories: amateur, anal, anal toying, anus, ass, beauty, big ass, bimbo, blonde, crossdressing

aShemaleTube

Lostwind Comp4

Categories: anal, asian, chinese, compilation, crossdressing, cumshot, femboy, hd, masturbation, sissy

aShemaleTube

Dizzy Miss Sizzy Christmas Video

Categories: hd, lingerie, sissy, stockings, xmas

KeekAss

Pastel

Categories: amateur, anal, crossdressing, dildo, feet, fetish, futanari, hd, homevideo, masturbation

KeekAss

Trans Sow Loren Aprile Assfuck Dehumanization

Categories: anal, anal toying, ass, assfucking, dildo, domination, femboy, femdom, fetish, hd

aShemaleTube

sissy rubber maid

Categories: amateur, asian, big tits, hd, latex, maid, mature, rubber, sissy, solo

aShemaleTube

Beautiful Butt Plugs in My Ass Compilation

Categories: anal, ass, beauty, big ass, compilation, dildo, hd, masturbation, mature, pussy

xHamster

A fucking African ebony curvy ass slut transgender strip and twerk tease

Categories: african, ass, beauty, big cock, creampie, crossdressing, curvy, ebony, hairy, hd

xHamster

Pink Seethrough D Cup Bra

Categories: amateur, bra, crossdressing, hd, lingerie, mature, sissy, solo

aShemaleTube

Watch Me Cum

Categories: amateur, crossdressing, cum, cumshot, hd, lingerie, masturbation, mature, sissy, small cock

xHamster

SEXIEST Pink Haired Femboy Fucked

Categories: amateur, american, anal, beauty, big ass, big cock, crossdressing, cum, femboy, feminization

aShemaleTube

Cute crossdresser shemale in public train station

Categories: booty, crossdressing, cute, dress, hd, high heels, lingerie, public, sissy, train

xHamster

Fashionable Footwear: Stepping Up Your Shoe Game

Categories: amateur, american, beauty, big ass, big cock, big tits, crossdressing, cum, game, hd

aShemaleTube

Asian sissy CD practices BJ and gags

Categories: asian, blowjob, chinese, crossdressing, deep throat, gagging, hd, model, oral, sissy

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

aShemaleTube

Sissy Camelia fuck machine training - 12Jan2021

Categories: assfucking, belgian, hd, mature, pornstar, sissy, small tits, solo, toys

Pornstars: Camelia

aShemaleTube

Leopard print bra and fishnet stockings

Categories: big ass, blonde, bra, crossdressing, femboy, fishnet, hd, ladyboy, lingerie, pantyhose

aShemaleTube

Rainbow sissy

Categories: anal, ebony, femboy, gay, hd, masturbation, sissy, solo

KeekAss

Cd tramp waiting for parent

Categories: amateur, anal, big ass, big tits, blonde, crossdressing, femboy, femdom, feminization, fetish

xHamster

This little slut wants to be pregnant

Categories: amateur, anal, big ass, colombian, crossdressing, femboy, gorgeous, hd, ladyboy, latina

xHamster

TINY DICK SISSY

Categories: amateur, british, crossdressing, feminization, ladyboy, lingerie, mature, pantyhose, sissy, small cock

aShemaleTube

Cute brunette Camelia

Categories: barebacking, brunette, bush, cute, dick, homevideo, lingerie, masturbation, pornstar, sissy

Pornstars: Camelia

xHamster

Small sissy cock tormented with wax

Categories: bdsm, bitch, clothed sex, dick, domination, feminization, fetish, fishnet, german, hardcore

aShemaleTube

All She wants fir Christmas is a big, fat Cock

Categories: amateur, big ass, big cock, big tits, blonde, dick, fat, hd, milf, model

KeekAss

Tiffany Ciskiss Bangs Her Sissy Lady Culo On Humungous Ribbed Fake Penis In Tub

Categories: amateur, anal, anal toying, ass, bathroom, crossdressing, dick, dildo, extreme, femboy

KeekAss

SISSY BIOTCH CAM COMPETE

Categories: amateur, anal, blonde, competition, crossdressing, cumshot, handjob, masturbation, sissy, solo

aShemaleTube

hot sissy latina trap toying her ass with dildo

Categories: ass, dildo, hd, latina, sissy, toys, webcam

aShemaleTube

TS Jessica riding on a bottle

Categories: anal, big cock, blonde, bottle, cumshot, hd, ladyboy, masturbation, riding, sissy

aShemaleTube

PVC outfit

Categories: amateur, big tits, blonde, crossdressing, hd, homevideo, sissy, small cock, webcam

xHamster

Huge Toys in My Siss Ass - the Tranny MILF

Categories: amateur, anal, ass, fishnet, hd, huge dildo, masturbation, mature, milf, pussy

TrannyOne

I can't hold sissygasm

Categories: amateur, anal, anal toying, crossdressing, cum, cumshot, dildo, femboy, hd, ladyboy

xHamster

Fashion Faves: Showcasing Your Wardrobe Staples

Categories: amateur, american, beauty, big ass, big cock, big tits, crossdressing, feminization, hd, ladyboy

aShemaleTube

Sissy cum from between crossed legs

Categories: amateur, crossdressing, cum, cumshot, femboy, fishnet, gloves, hd, high heels, homevideo

KeekAss

Mask Female, Luna Cosplayer Deep-Throat My Schlong, Get torn up Anime Porn Mischievous Asian Costume Play

Categories: amateur, anal, anime, asian, beauty, blowjob, chinese, cosplay, costume, crossdressing

aShemaleTube

Tgirl with long dildo

Categories: assfucking, dildo, hd, sissy, teen (18+), tgirl, toys, ukrainian, underwear, webcam