Sissy Shemale Videos » 34

xHamster

Love for Sports: Staying Active and Fit

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xHamster

Sissy Magic Bomb Chastity Cage Challenge

Categories: american, beauty, cage, cosplay, crossdressing, fetish, hd, ladyboy, lingerie, sissy

aShemaleTube

slender blonde transgirl in stockings and mask strokes her cock

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KeekAss

Jizz sans fapping, Clad Rubbin' Jerk Off Instructions

Categories: amateur, asian, brunette, crossdressing, cumshot, dirty talk, domination, femdom, fetish, hd

KeekAss

Game Hermaphroditism Intrusion Gang-Fuck

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TrannyOne

Large Titties Oriental American sissy t-girl trap cum dump gets mouth banged and used bareback with creampie doggie and riding on the bang seat POV Pr

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aShemaleTube

Trixy devil fucked hard by her guy

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xHamster

Sexyfilomena Puts It Deep in Her Little Bitch Ass

Categories: amateur, anal, anal toying, ass, bitch, blowjob, canadian, crossdressing, cum, dildo

xHamster

Rubberdoll Sophia in full silicone dollsuit fucks herself with dildos

Categories: big tits, cumshot, dildo, doll, fake tits, german, hd, homevideo, ladyboy, masturbation

Pornstars: Rubberdoll

aShemaleTube

Femboyhami 2

Categories: anal, crossdressing, femboy, hd, masturbation, sissy, small cock, small tits, teen (18+), uniform

aShemaleTube

Good girl love vagetable!!!

Categories: anal, asian, chinese, femboy, fetish, hd, ladyboy, lingerie, model, sissy

xHamster

Destroying My Big Sissy Ass - MILF

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

aShemaleTube

Hard Clit Between Sexy Spread Legs - Evelina Trojan

Categories: amateur, big cock, clit, crossdressing, cumshot, femboy, hd, high heels, homevideo, legs

xHamster

Big shemale cumshot on webcam

Categories: amateur, crossdressing, cum, cumshot, dress, femboy, hd, lingerie, masturbation, orgasm

KeekAss

Paying your debt to sandy-haired fat knob collegue

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KeekAss

Bi-Atch super-bitch crossdresser rectal deep humungous dark-hued faux-cock

Categories: amateur, anal, anal toying, ass, big ass, big cock, bisexual, bitch, booty, crossdressing

aShemaleTube

Mature Tgirl Janis Wylde will you play with me

Categories: amateur, blonde, crossdressing, femboy, hd, mature, sissy, small tits, tgirl

aShemaleTube

Latest Live Sex Show 02.06.2025 Ep4

Categories: amateur, anal, barebacking, blowjob, british, couple, creampie, hd, ladyboy, mature

xHamster

riding in my pink heels

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xHamster

Pig Sucking Her Feet for Sir Lando

Categories: amateur, british, cum, feet, fetish, hd, masturbation, sissy, solo, sucking

xHamster

Reyna Wants Her Daddy to Fuck Hard

Categories: anal, asian, beauty, big ass, cute, daddies, filipina, handjob, hardcore, hd

xHamster

cutie shows legs and toes

Categories: bbw, cute, hd, homevideo, legs, pov, sissy, solo, teen (18+), toes

KeekAss

Just Another Sunday Cowboy Breakfast with @KAROLDIESEL, OnlyFans Flick Domina

Categories: amateur, anal, ass, assfucking, big cock, big tits, crossdressing, dominatrix, hd, homevideo

KeekAss

Two Hot Naughty Shemales Live On Cam

Categories: amateur, anal, beauty, brunette, crossdressing, dildo, homevideo, japanese, lingerie, maid

KeekAss

Tatted giant parent hunk tonguing femboys boipussy, bj and sole fetish in fishnets

Categories: amateur, anal, asian, beauty, big cock, black, couple, crossdressing, cum, cumshot

KeekAss

Game infinite: Isabela and [FUTA]

Categories: 69, big ass, big cock, big tits, femdom, futanari, game, hd, lesbian, lezdom

KeekAss

My Spunk Compilation Movies Part ten

Categories: amateur, chubby, compilation, crossdressing, cum, cumshot, ebony, fat, hd, masturbation

aShemaleTube

Two Sissys having Fun together - Part 2: Fucking

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

xHamster

The Maid Is Cleaning the Hotel Room While Fucked Her Hard

Categories: amateur, anal, barebacking, blowjob, hardcore, hd, hotel, maid, mature, sissy

xHamster

🔶CAM⁴ La Pétasse [¹fev²⁵] (2) VBx PcTrvProd91

Categories: amateur, bitch, crossdressing, french, hd, high heels, lingerie, sissy, skinny, slut

aShemaleTube

Holly smoking while waiting on some cock

Categories: crossdressing, cum, dick, hd, mature, model, panties, sissy, smoking, stockings

xHamster

Sissy Maid Struggling in new Armbinder and Steel Chastity Belt with 7" Dildo Locked inside

Categories: amateur, anal toying, bdsm, beauty, bondage, canadian, crossdressing, dildo, fetish, hd

KeekAss

Crossdressing Rileydix and her Delicious Sissy Donk!

Categories: amateur, ass, big ass, blonde, clit, crossdressing, dick, dirty talk, hd, homevideo

xHamster

POV GoPro Cam - Amateur BBC fucks big blond shemale's white ass pussy - with 2 slow-motion sections - Candy Ass Sissy

Categories: amateur, american, anal, bbw, big ass, big black cock, blonde, crossdressing, fat, hd

Pornstars: Candy Ass

aShemaleTube

Kinky sissy in shiny latex bodysuit and high boots plays with cock and cums in her mouth

Categories: amateur, asian, big cock, boots, creampie, crossdressing, cum, dick, domination, fetish

Pornstars: Viper

aShemaleTube

Kinky alt femboy kate murano sissy crossdresser gets dominated and fucked with strapon

Categories: anal, blowjob, crossdressing, domination, femboy, hd, kinky, lingerie, sissy, stockings

aShemaleTube

High on Shemale Mushrooms 🍄

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xHamster

Tuck Omanko Stripper Pai-chan

Categories: amateur, asian, crossdressing, femboy, hd, japanese, mature, sissy, small cock, small tits

xHamster

Chubby red and greeen apple anal insertion

Categories: anal, anal toying, bbw, chubby, fetish, gaping hole, hd, insertion, masturbation, mature

xHamster

Secretdreamsfuta Delicious Hot Ass Dripping Cum Intense Pleasure Cum Thirsty Slut Hot Ass

Categories: amateur, american, asian, ass, barebacking, big ass, big cock, crossdressing, cum, hd

aShemaleTube

MY LOVE 025

Categories: asian, chinese, crossdressing, cumshot, ladyboy, lingerie, masturbation, sissy, solo, stockings

aShemaleTube

Dana Deana .. cumgirl in white lingerie

Categories: amateur, compilation, crossdressing, lingerie, masturbation, mature, sissy, slut, small cock, solo

xHamster

Hot Booty Femboy On Live Cam Show Flowerfull Dress My Best Lovely One

Categories: amateur, american, beauty, big ass, big tits, blonde, booty, crossdressing, dress, femboy

aShemaleTube

Cd opening legs for master

Categories: amateur, blowjob, crossdressing, homevideo, interracial, legs, lingerie, master, sissy, stockings

KeekAss

Jacking In Pinkish Silk & Satin

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

aShemaleTube

Sissy Crossdresser riding Daddy's thick cock

Categories: amateur, crossdressing, daddies, dick, homevideo, lingerie, riding, sissy, slut, street

aShemaleTube

Tranny mistress dominates a sissy

Categories: amateur, anal, homevideo, lingerie, mistress, sissy, tranny

aShemaleTube

Blonde in a hot pink bodystocking

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

aShemaleTube

Cute teen edging girl cock 💗

Categories: amateur, blonde, cute, dick, edging, femboy, hd, homevideo, masturbation, sissy

xHamster

Warming up on My Xl Tail Whip Trainer

Categories: amateur, anal, anal toying, british, crossdressing, dildo, femboy, hardcore, hd, huge dildo

xHamster

Adelina cumming

Categories: cum, cumshot, european, hd, ladyboy, masturbation, mature, romanian, sissy, solo

KeekAss

Big schlong getting into my lil' arse

Categories: amateur, anal, anal toying, ass, beauty, big ass, big cock, crossdressing, dildo, hd

KeekAss

nylondelux in ellen amber tights

Categories: amateur, anal, ass, crossdressing, cum, dress, feet, fetish, hd, high heels

aShemaleTube

👑Jupe🍑🖤Cuire & Mise en Laisse. Une putain de Pouffiasse à Enculer sur sa Chaise. CAM4 VBX

Categories: amateur, bimbo, bitch, crossdressing, escort, french, hd, sissy, skinny, slut

xHamster

Fucked Doggy in a Cute Little Outfit

Categories: amateur, american, anal, creampie, cute, doggystyle, hd, interracial, sissy, stockings

xHamster

Sissy Whore Training - Sissyfication 1

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

xHamster

Sissy shaving - feminization

Categories: amateur, bdsm, bondage, crossdressing, feminization, handjob, hd, homevideo, ladyboy, masturbation

KeekAss

Taiwanese sissy have fun with machine fuck stick

Categories: amateur, anal, anal toying, asian, big ass, crossdressing, dildo, femboy, funny, hd

aShemaleTube

Blonde sissy jerking her cock with cock sleeve

Categories: blonde, dick, futanari, handjob, hd, jerking, masturbation, sissy, solo, toys

TrannyOne

Sexy Italian Pennymilano cums at 8:23

Categories: amateur, crossdressing, cum, cumshot, italian, lingerie, masturbation, sissy, small cock, small tits

aShemaleTube

sissy fucked deep with a strap on

Categories: bdsm, femdom, humiliation, lingerie, mistress, sissy, stockings, strap-on

xHamster

36V Tan Pantyhose and Blue Toenails

Categories: amateur, australian, big cock, boy, creampie, crossdressing, cumshot, cute, dick, femboy

KeekAss

4K. Valkyria Domme creep in her massive man meat to dual cootchie tear up and dual internal ejaculation

Categories: amateur, beauty, big cock, couple, cum, dick, dominatrix, femdom, huge cock, ladyboy

TrannyOne

These shemales will show you the way of sissy training

Categories: ball licking, big cock, blonde, brunette, compilation, crossdressing, cumshot, dick, humiliation, sissy

aShemaleTube

18yo skinny femboy with small boobs webcams solo

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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

AlphaPorno

MILF with amazing curves tries tranny cock in surreal positions

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aShemaleTube

Indulge in Asian Femboy's WET BUSSY PART 2

Categories: amateur, anal, asian, big cock, chinese, compilation, crossdressing, cumshot, hd, sissy

KeekAss

Bootylicious Femboy Snowbunny Blows Her Back Out

Categories: amateur, anal, big black cock, booty, cage, crossdressing, dildo, dress, femboy, fetish

KeekAss

Doofy movies compilation of a trans doll with animation sounds

Categories: amateur, animation, brunette, cartoon, compilation, curly haired, cute, doll, femboy, fetish

xHamster

Sugardaddy Suck my Sissy Hard Cock

Categories: amateur, big cock, blowjob, crossdressing, dick, domination, hd, italian, ladyboy, latina

KeekAss

Nailing Steamy Latin Crossdresser Luna Sol Rock-Hard

Categories: amateur, anal, beauty, crossdressing, femboy, hd, homevideo, latina, mature, mexican

KeekAss

My Sundress-Up Darling, Rizu-kyun cosplayer get pulverized with bang-out plaything, anime costume play

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

aShemaleTube

TS 720

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

aShemaleTube

Fucking Trans Kelsey Masters Raw Hardcore - Compilation 1

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aShemaleTube

sissy machine fuck 03

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xHamster

Mistress Completely Destroys Her Obedient Cumdump

Categories: amateur, anal, big tits, blowjob, cumshot, cute, hd, mistress, sissy, sloppy

xHamster

Your Sissy Destiny - Sissification Encouragement Affirmation

Categories: amateur, american, blonde, cum, dirty talk, femboy, feminization, fetish, hd, joi

KeekAss

Railing an meaty fake penis with my cock-squeezing bum made me jizm

Categories: anal, big ass, big cock, boy, cum, cumshot, dick, dildo, femboy, gay

xHamster

Horny shemale home alone in chastity cage

Categories: anal, asian, big ass, big tits, cage, compilation, dick, femboy, handjob, hd

xHamster

I fuck a sexdoll with my big cock

Categories: amateur, big ass, big cock, big tits, blonde, cute, domination, femdom, hd, italian

ShemaleZ

Cammy White In Sissy Edges While Chained

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

KeekAss

Encaged PHAT ASS WHITE GIRL Sissy plays with pink hole!

Categories: amateur, anal, anal toying, ass, big ass, buttplug, cage, clit, crossdressing, cumshot

KeekAss

4K. TRANSSEXUAL Katie Fox gets pummeled by TRANSSEXUAL Valkyria dominatrix

Categories: beauty, big cock, cum, cumshot, dominatrix, huge cock, ladyboy, mature, orgasm, pantyhose

TrannyOne

Vintage blonde shemale takes a smoke and sucks a cock

Categories: blonde, blowjob, classic, dick, femboy, ladyboy, sissy, smoking, sucking, tgirl

aShemaleTube

Mini Basketball Anal Insertion Compilation Ft Sissy Kenzie Star

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

xHamster

Sissykanisa's Lingerie Collection Ep19 Part2: Sexy Purple Stocking Handjob

Categories: amateur, anal, asian, crossdressing, cum, cumshot, handjob, hd, ladyboy, legs

xHamster

White nails

Categories: amateur, american, bathroom, hd, homevideo, masturbation, mature, pov, sissy, small cock

xHamster

Double Penetration with Big Vibrators

Categories: amateur, anal, anal toying, crossdressing, dildo, double penetration, european, hd, huge dildo, masturbation

xHamster

Teen Sissy Twerking Ass For BBC in Chastity Cage

Categories: amateur, american, anal, ass, big ass, big black cock, cage, compilation, cute, hd

xHamster

My Sexy Skirt, My Dildo and I Enjoying Myself Here

Categories: amateur, anal, dildo, high heels, homevideo, masturbation, mature, sissy, skirt, solo

KeekAss

Alissa Crossdresser corrida en fuck stick y lo chupo

Categories: amateur, anal, anal toying, crossdressing, cumshot, dildo, feet, femboy, fetish, footjob

TrannyOne

Cute Asian tranny can turn any man into a sissy

Categories: asian, close up, cute, dick, handjob, high heels, juicy, ladyboy, natural tits, sissy

aShemaleTube

Self-masturbation and pussy stretching

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aShemaleTube

ava_adora pmv

Categories: amateur, anal, blonde, hd, sissy, solo

xHamster

Late night Thug BBC masturbating big black cock

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xHamster

Cute sissy in chastity sounding until squirting all over the place!

Categories: american, cum, cute, dick, fetish, pantyhose, pissing, sissy, skirt, slave

xHamster

Straight Married Neighbor Fucks Naughty Trans Girl and Fills Her Ass with Cum

Categories: amateur, anal, ass, barebacking, blowjob, cum, hd, naughty, neighbor, sissy

aShemaleTube

Mireya Rinaldi Her Big Balls Licked and Sucked

Categories: balls, big cock, domination, fetish, interracial, latina, licking, sissy, sucking

xHamster

Sissy Girl have Fun

Categories: amateur, anal, anal toying, crossdressing, cum, danish, dildo, funny, hd, homevideo

xHamster

Crossdresser cumming tutorial

Categories: amateur, crossdressing, cum, cumshot, hd, ladyboy, latina, lingerie, masturbation, mexican

xHamster

Bound sissy slut - fuck her somebody

Categories: amateur, big tits, bondage, bound, crossdressing, european, german, hd, lingerie, sissy

KeekAss

AJ180 Chats Muddy, Groans & Dumps three Immense Cum Shots in "3 She Blows"

Categories: balls, big ass, big black cock, big cock, big tits, black, cum, cumshot, dick, dirty

KeekAss

MUDDY GARDENBOY FASHION GUZZLE CRIMSON LIPPSTICK SISSY YOUTHFULL

Categories: blowjob, garden, hd, lingerie, mud, sissy, stockings, webcam

aShemaleTube

BBC-Fantasy Vol.1

Categories: amateur, big black cock, big cock, fantasy, futanari, hd, homevideo, lingerie, sissy, solo

VideoSection

Amateurs femboy Jezabelle420 clumsily plays with cock for a massive cumshot

Categories: amateur, beauty, big cock, blonde, crossdressing, cum, cumshot, dick, femboy, handjob

ShemaleMovie

Teasing you in my sexy undergarments and panties

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aShemaleTube

HOT EXTENDED TRAILER SISSY STEPH GETS PUNISHED! Takes a nasty facial cumshot

Categories: anal, big black cock, blowjob, cowgirl, cumshot, doggystyle, facial, hd, punishment, sissy

xHamster

Transvestite lyonnais anal.

Categories: anal, belgian, european, hd, homevideo, sissy, solo, stockings, transsexual, transvestite

xHamster

I Need Your Cum in My Ass Daddy Please!!!

Categories: anal, ass, big ass, cum, daddies, dildo, fucking machine, hd, masturbation, milf

xHamster

Princess Bunnie: Leggy CD Cums with Tits Out

Categories: amateur, american, crossdressing, cum, cumshot, glasses, hd, high heels, legs, lingerie

xHamster

Pretty Shemale smoking fetish

Categories: amateur, american, beauty, big ass, big cock, blonde, booty, crossdressing, fetish, hd

KeekAss

Sissy plaything throatfucks herself on the satans hour

Categories: amateur, big black cock, crossdressing, deep throat, femboy, hd, homevideo, masturbation, pov, sissy

JizzBunker

BBW slut pegging a sissy deep

Categories: amateur, anal, bbw, hardcore, pegging, sissy, slut, strap-on

aShemaleTube

Sexy Turkish Slim Sissy

Categories: amateur, crossdressing, ladyboy, sissy, slim, teen (18+), turkish

aShemaleTube

Teasing nylon sissy milf tranny

Categories: amateur, crossdressing, hd, mature, milf, nylon, pantyhose, sissy, tease, tranny

ShemaleMovie

Joselynne Crossdresser gets playful in the bathroom with a big dildo

Categories: amateur, anal, anal toying, ass, bathroom, big ass, crossdressing, dildo, femboy, high heels

xHamster

Sissykanisa's Lingerie Collection Ep20 Part1: Red Shiny Stocking with Panties

Categories: amateur, asian, crossdressing, handjob, hd, ladyboy, legs, lingerie, panties, pantyhose

KeekAss

Sissy OClock tears up CD bum with backside ass-plugs Crossdresser ASS-FUCK Femboy

Categories: amateur, anal, ass, assfucking, babe, bisexual, buttplug, crossdressing, femboy, feminization

aShemaleTube

Adidas Swimsuit Cumshot

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