Sissy Shemale Videos » 49

aShemaleTube

Orgasmic Lily intense edging & cuming💦

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xHamster

Secretdreamsfuta Delicious Intense Anal Riding Sweet Tasty Big Ass Swallowing Huge Monster Cock in Her Tight Anus Hardcore Sex

Categories: amateur, american, anal, anus, asian, big ass, big cock, crossdressing, cum, cum swallowing

xHamster

Ladyboy Love: Celebrating Beauty and Diversity

Categories: amateur, american, beauty, big ass, big cock, celebrity, crossdressing, femdom, feminization, first time

aShemaleTube

dizzy the secretary gets tied up

Categories: bondage, crossdressing, gagging, hd, lingerie, secretary, sissy, stockings, tied up, tranny

KeekAss

Femboy with meaty rump get drilled

Categories: amateur, anal, big ass, big cock, creampie, crossdressing, cum, drilling, femboy, hd

aShemaleTube

Book Show

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xHamster

This Queen Is Very Sexy and Hot in the Whole World

Categories: anal, asian, ass, beauty, big ass, blonde, crossdressing, cum, cute, dick

xHamster

Machine fucking my sissy hole open

Categories: amateur, fucking machine, hd, sissy, webcam

HotMovs

Fucking Sissy With Strap On Pegging His Ass With Big Dildo

Categories: ass, big cock, big tits, cumshot, dildo, hd, lingerie, pegging, pov, sissy

KeekAss

Two Horny Tranny Masturbate On Webcam

Categories: amateur, beauty, big ass, big tits, brunette, glasses, hd, homevideo, interracial, masturbation

aShemaleTube

Naughty Sissy Petticoated Milked and Spanked

Categories: amateur, crossdressing, cumshot, domination, lingerie, masturbation, naughty, sissy, spanking

xHamster

Teasing You and Wearing My Lingerie and Pantes.

Categories: ass, bbw, big ass, black, chubby, crossdressing, cute, fat, hairy, hd

xHamster

Baby Isn't This Too Much for You?

Categories: amateur, anal, babe, dildo, hd, ladyboy, masturbation, reality, sissy, stockings

aShemaleTube

teen nerdy shemale anal play on cam

Categories: amateur, anal, hd, homevideo, lingerie, masturbation, nerdy, sissy, small tits, solo

xHamster

Sissy Orgasm with Deep Dildo Penetration in Shiny Panties and Bra

Categories: amateur, bra, dildo, hd, lingerie, masturbation, orgasm, panties, sissy, solo

XXXDan

Sissy Loren is desperate to be fucked

Categories: amateur, big cock, desperate, hardcore, masturbation, mature, sissy, small tits, solo, spanish

aShemaleTube

j4n3uk red heels catsuit piss and cucumber fuck

Categories: catsuit, crossdressing, cucumber, hd, high heels, homevideo, latex, pissing, sissy, solo

KeekAss

Oild up good-sized rump sissyboi femboi dirty dancing black underwear

Categories: amateur, anal, ass, beauty, big ass, big black cock, bimbo, black, booty, crossdressing

TrannyOne

Sissy Chloe Playing With A Fleshlight

Categories: amateur, fleshlight, masturbation, sissy

aShemaleTube

Little slut fucks her ass

Categories: ass, crossdressing, hd, ladyboy, sissy, slut, tgirl, tranny, transsexual

aShemaleTube

Shemale doll gives painal to her sissy partner

Categories: amateur, anal, doll, homevideo, lingerie, sissy, stockings, tranny

VideoSection

Hd videos, tiny dick shemale

Categories: asian, cosplay, hd, ladyboy, pantyhose, sissy, small cock, stockings, teen (18+), tiny dick

aShemaleTube

Amateur CD Rides In Thigh Highs

Categories: amateur, asian, chinese, crossdressing, femboy, pantyhose, sissy, small tits, solo, stockings

xHamster

Celine in the shower getting ready for a big sex filled weekend.

Categories: amateur, american, anal, behind the scenes, compilation, crossdressing, hd, masturbation, mature, shower

KeekAss

Shemale Love Masturbation Show

Categories: amateur, beauty, doggystyle, futanari, homevideo, masturbation, orgy, public, sissy, solo

KeekAss

Anal Invasion screwing this Sissy with a BIGG fuck stick

Categories: amateur, anal, assfucking, bdsm, dildo, femboy, femdom, fetish, hd, kinky

KeekAss

Mask Chick, Luna Cosplayer Gargle My Meatpipe, Manga Porn Ultra-Kinky Asian Costume Play part.nine

Categories: amateur, asian, beauty, blowjob, chinese, cosplay, costume, crossdressing, femboy, handjob

TrannyOne

Sissy crossdresser in chastity gets pounded hard by a fucking machine

Categories: amateur, crossdressing, fishnet, fucking machine, kinky, masturbation, sissy, stockings

aShemaleTube

I want to spunk but if I hold myself back — myLanaSky

Categories: amateur, crossdressing, cumshot, homevideo, ladyboy, masturbation, sissy, solo, teen (18+), toys

ShemaleMovie

Sexy transgender sissy crossdresser Vanessa Bitchx in high heels and lingerie

Categories: amateur, ass, babe, bdsm, beauty, big ass, big cock, crossdressing, european, french

Pornstars: Sexy Vanessa

XXXDan

Sissy cd anal solo fucking machine

Categories: amateur, anal, crossdressing, dildo, european, fetish, fucking machine, hardcore, russian, sissy

KeekAss

Japanese femboy milks in a JK costume play clothing. part1

Categories: asian, cosplay, costume, crossdressing, cute, femboy, hd, japanese, masturbation, sissy

xHamster

Sissy Slut Showing off Her Filthy Long Legs and Perfect Ass

Categories: amateur, anal toying, ass, beauty, crossdressing, feminization, hd, high heels, legs, lingerie

xHamster

Home made fashion with ZZ hehe I took my scissors and redesigned my metallic blue dress to make it more revealing

Categories: ass, australian, beauty, crossdressing, dress, hd, high heels, homevideo, lingerie, mature

xHamster

Breathplay latex red doll

Categories: bondage, breath play, doll, european, hd, homevideo, latex, sissy, solo, teen (18+)

xHamster

Dildo deep inside me making me cum so hard

Categories: amateur, anal, ass, beauty, crossdressing, cum, dildo, femboy, hd, masturbation

KeekAss

Spank the jizm out of it dame

Categories: amateur, big ass, big cock, big tits, crossdressing, cum, cumshot, dick, hd, homevideo

aShemaleTube

Ts Stroka talking to a sloppy bussy with her hard Big Black Cock

Categories: anal, barebacking, big ass, big black cock, big cock, big tits, creampie, ebony, femboy, homevideo

ShemaleMovie

Fishnet sissy takes on a massive anal plug with her forearm

Categories: anal, anal toying, ass, dildo, fishnet, fisting, gaping hole, huge dildo, japanese, masturbation

ShemaleMovie

Wild hotel hookup leads to intense orgasm and loud moans

Categories: anal, bbw, close up, creampie, crossdressing, cum, cumshot, dildo, greek, handjob

HClips

Fat Cd Sissy Blowjob With Nice Cumshot With Fiona Fortune

Categories: amateur, american, anal, assfucking, big ass, blonde, blowjob, booty, booty shake, cum in mouth

xHamster

Alisa Crossdresser Solo

Categories: amateur, beauty, crossdressing, cute, european, finnish, hd, pantyhose, sissy, small tits

KeekAss

Finger-Banging Myself at a Public Park!

Categories: amateur, ass, bbw, big ass, crossdressing, cum, fingering, hd, masturbation, orgasm

aShemaleTube

Linday the Fucking Slut

Categories: amateur, anal, crossdressing, exhibitionist, hd, masturbation, sissy, slut, solo, stockings

TrannyOne

Femboy riding a blue silicone dildo

Categories: amateur, anal, anus, ass, booty, crossdressing, czech, dildo, european, fake tits

aShemaleTube

Me Sissy Samana(CB:showlover12) cum again

Categories: anal, crossdressing, cum, cumshot, hd, lingerie, masturbation, pantyhose, sissy, stockings

aShemaleTube

Axel Reigns _TS-Bride-Spitroasted-amp-Creampied.mov

Categories: big black cock, bride, hd, sissy, spit

xHamster

Fuck my ass with a dildo

Categories: amateur, anal, anal toying, ass, big ass, big cock, dildo, hd, homevideo, masturbation

xHamster

Sissy Femboi in Red Fishnet Stockings P1

Categories: amateur, beauty, big cock, canadian, compilation, crossdressing, dick, edging, femboy, fishnet

ShemaleZ

Horny Femboy Big Ass Takes Bbc Cum Eating With Sissy Crossdresser

Categories: anal, big ass, big black cock, big cock, blowjob, colombian, crossdressing, cum, femboy, hd

xHamster

Secretdreamsfuta Hard Anal Sex Delicious Intense Sexual Threesome Dolce Tasty Big Ass Swallowing Huge Cock Tasty Hard Sex

Categories: 3some, amateur, american, anal, asian, big ass, big cock, black, compilation, crossdressing

xHamster

Sexy Model Secrets: Embrace Your Confidence and Style!

Categories: amateur, american, asian, couple, crossdressing, cum, femboy, first time, hd, ladyboy

xHamster

Blondes and Psychedelic Sex (part 6) Remastered - Futa Animation

Categories: amateur, animation, barebacking, beauty, big ass, big cock, blonde, blowjob, creampie, cum

KeekAss

sissy Crossdresser Selenahot humped by Machine two

Categories: amateur, anal, anal toying, big ass, crossdressing, dildo, fucking machine, hd, masturbation, pov

aShemaleTube

Sissy waitress dildo fuck and anal orgasm

Categories: anal, ass, assfucking, dildo, hd, orgasm, sissy, small tits, solo, toys

aShemaleTube

TS 449

Categories: amateur, asian, big cock, femboy, sissy, solo, teen (18+), transsexual, webcam

aShemaleTube

Helga Smoking, Wanking, Cumming In Nice Lingerie - [2025-05-12]

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

HDSex

Korean femboy amateur gets anally pounded by a sexy amateur shemale

Categories: amateur, anal, asian, beauty, blowjob, brutal, cosplay, crossdressing, femboy, handjob

KeekAss

Sissy trans mega-bitch inserts her rump on camera

Categories: anal, bitch, dildo, femboy, hd, masturbation, sissy, small tits, tgirl, toys

aShemaleTube

Anal adventures of a whore in a motel room part 2 *** tgirl floozyJezebelle

Categories: amateur, anal, anal toying, big ass, femboy, hd, huge dildo, ladyboy, motel, pantyhose

xHamster

Fucking my ass with huge dildos - tranny milf

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

KeekAss

Shemale Stroking Her Massive Dick

Categories: amateur, beauty, big cock, domination, ebony, feet, femboy, homevideo, jerking, masturbation

KeekAss

Uber-Sexy Sissy High High-Heeled Shoes and Dancing

Categories: amateur, crossdressing, cumshot, dancing, fetish, handjob, hd, high heels, homevideo, masturbation

TrannyOne

Mature sissy couple loves blowjob, fist and double fist

Categories: anal fisting, assfucking, blonde, blowjob, couple, dick, fisting, mature, old, oral

aShemaleTube

nerdy sissy slut faggot cd gets fucked by Chubby daddy

Categories: chubby, crossdressing, daddies, nerdy, sissy, slut

aShemaleTube

Mature Sissy Tranny Shows Off Her Huge Cock and Fucks Herself Live on Cam

Categories: amateur, anal, asian, big cock, crossdressing, homevideo, huge cock, masturbation, mature, sissy

xHamster

Murphy cleans him...

Categories: amateur, anal, anal toying, dildo, fishnet, german, hd, lingerie, masturbation, sissy

xHamster

Shemale in thong pounding gaping ass with octopus dildo and jerking big cock to cumshot

Categories: amateur, anal, anal toying, asian, ass, big cock, cum, cumshot, dildo, femboy

xHamster

Hard Fucked by Dutch

Categories: anal, barebacking, beauty, big ass, couple, crossdressing, cute, doggystyle, dutch, femboy

KeekAss

How to put a Fufu pinch on and how to pis with a Fufu clamp

Categories: amateur, boy, clamp, crossdressing, femboy, feminization, fetish, gay, golden shower, handjob

xHamster

Burning Passion: Fueling the Flames of Desire

Categories: amateur, american, bbw, beauty, big ass, big cock, big tits, crossdressing, cum, femboy

aShemaleTube

Ass dance black dress 2

Categories: amateur, ass, big ass, black, dress, hd, homevideo, ladyboy, lingerie, sissy

aShemaleTube

Japanese Sissy Dildo Solo Cum with Purple Swimsuit, Tan Pantyhose, Boots

Categories: amateur, asian, boots, crossdressing, cum, cumshot, dildo, fetish, hd, homevideo

xHamster

Hot Femboy Fucks Trans Kelsey Masters

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

xHamster

Use Huge Toys to Fuck Your Ass - Sissy Training 018 - the Tranny MILF

Categories: anal, ass, big ass, cumshot, fucking machine, hd, huge dildo, masturbation, milf, pussy

KeekAss

Sissy Ass Twerk

Categories: amateur, ass, booty, crossdressing, hd, mistress, pawg, sissy, solo, twerk

xHamster

Super Sexy Blonde Femboy Bailey Wilde Photoshoot

Categories: amateur, american, anal, bdsm, beauty, blonde, crossdressing, cum, femboy, feminization

aShemaleTube

Thailand femboy satisfy herself

Categories: asian, barebacking, cumshot, femboy, hd, homevideo, ladyboy, masturbation, sissy, small tits

xHamster

my hot, tight and juicy ass for you clip 1

Categories: anal, ass, barebacking, big ass, homevideo, juicy, ladyboy, sissy, tight, transsexual

xHamster

Red head sissy fun

Categories: amateur, big tits, fetish, funny, hd, ladyboy, lingerie, mature, redhead, sissy

KeekAss

sissy sounding joy

Categories: amateur, brunette, crossdressing, fetish, hd, masturbation, sissy, small tits, solo, toys

aShemaleTube

Amazing Ass Cheeks Slutty Booty Shorts cars driving by Sissy

Categories: amazing, ass, booty, first time, hd, mature, pov, shorts, sissy, slut

HClips

Sissy Kanisa Crossdresser Play With Anal Bead Vibrator On Her Creampie Anal With Sissy Crossdresser

Categories: amateur, anal, asian, assfucking, big ass, booty, booty shake, brunette, creampie, crossdressing

aShemaleTube

Obsessed - PMV by HoloPMV

Categories: amateur, anal, big cock, blowjob, compilation, crossdressing, domination, hd, ladyboy, sissy

xHamster

Exercise in pantyhose and masturbate

Categories: crossdressing, fetish, hd, masturbation, orgasm, pantyhose, prostate, sissy, solo, stockings

aShemaleTube

Facefucking Session with Daddy and His Sissy Boi

Categories: amateur, anal, asian, big ass, big cock, big tits, daddies, face fucking, hd, ladyboy

Pornstars: Viper

xHamster

Blondes and Psychedelic Sex (part 9) Remastered - Futa Animation

Categories: amateur, animation, barebacking, beauty, big cock, blonde, blowjob, cartoon, creampie, cum

KeekAss

insane step-mom roleplay she masturbates off you and her milk in the coffee

Categories: amateur, big cock, brunette, cum, cumshot, dick, dirty, dirty talk, domination, handjob

aShemaleTube

BG70 Sexy Upskirted Reader

Categories: amateur, exhibitionist, flashing, lingerie, panties, sissy, stockings, tease, tranny, upskirt

aShemaleTube

Everything in the mouth 💦

Categories: amateur, anal, cum, cum in mouth, cumshot, facial, french, ladyboy, masturbation, sissy

MyLust

Redheaded femboy gets that asshole fucked by a kinky machine

Categories: anal, ass, big cock, boy, cum, cumshot, doggystyle, femboy, insertion, kinky

ShemaleMovie

Cum-filled condom on hotel balcony - Sissy sequel with stocking-clad hottie!

Categories: anal, ass, balcony, bathroom, condom, cum, cumshot, handjob, hotel, jerking

aShemaleTube

Crossdresser wants your cock in her ass

Categories: amateur, ass, buttplug, crossdressing, dick, hd, homevideo, mature, model, sissy

aShemaleTube

Lots Of Precum & Big Double Cumshot

Categories: big cock, cum, cumshot, edging, femboy, garter belts, hd, lingerie, milf, model

JizzBunker

Sissification 22 Animation

Categories: animation, sissy

aShemaleTube

Young sissy cums while riding huge dildo

Categories: barebacking, big cock, cum, cumshot, femboy, homevideo, huge dildo, lingerie, masturbation, pantyhose

KeekAss

Salivating sissy plays with her hatch and nips

Categories: amateur, bathroom, bdsm, brunette, crossdressing, fetish, gagging, hd, homevideo, masturbation

TrannyOne

Gorgeous tranny gets plowed by two dicks in a bar

Categories: 3some, amateur, bar, blonde, crossdressing, dick, femboy, gorgeous, group sex, ladyboy

aShemaleTube

Sissy latex maid Lucy getting pegged in the kitchen

Categories: amateur, assfucking, hd, kitchen, latex, maid, mature, sissy, spandex, toys

aShemaleTube

Sissy Workout Compilation 32

Categories: amateur, anal, compilation, fetish, fisting, hardcore, homevideo, latina, masturbation, sissy

aShemaleTube

Sissy JOI

Categories: crossdressing, domination, joi, lingerie, masturbation, sissy, small cock

XXXDan

Big Tits Asian American sissy tranny trap used as a cum dump throat fuck riding cowgirl on fuck seat doggie bareback creampie p2

Categories: amateur, american, anal, asian, barebacking, big tits, cowgirl, creampie, crossdressing, cum

xHamster

Enjoying myself in a beautiful pink lingerie

Categories: amateur, beauty, blonde, crossdressing, femboy, hd, lingerie, masturbation, sissy, skinny

xHamster

misr4 - Anal ride in pantyhose

Categories: anal, anal toying, crossdressing, cum, cumshot, dick, dildo, handjob, hd, huge dildo

KeekAss

Big Tits Big Ass Big Dick

Categories: amateur, beauty, big ass, big cock, big tits, cute, domination, femboy, hd, homevideo

xHamster

DIY Couture: Creating Your Own Fashion Pieces

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

aShemaleTube

night public walk and cum

Categories: amateur, big cock, chinese, crossdressing, cum, cumshot, lingerie, masturbation, mature, outdoor

KeekAss

Sissy Breezy Lola gets handcuffed and pounded by BIG BLACK COCK

Categories: amateur, anal, ass, assfucking, bdsm, big black cock, big cock, blonde, crossdressing, femboy

KeekAss

Shoeplay with Nylon Soles in White Ballerina Boots

Categories: amateur, ballerina, beauty, boots, crossdressing, feet, fetish, hd, lingerie, nylon

TrannyOne

Inked blonde TS Aubrey Kate barebacks bald cock sucker's ass

Categories: anal, ass, babe, blonde, dick, femboy, hairless, ladyboy, pornstar, sissy

Pornstars: Aubrey Kate

KeekAss

Talk Sissy DUAL CUM-SHOT Arms Free-For-All Climax

Categories: amateur, anal, asian, assfucking, crossdressing, cum, cumshot, handjob, hd, licking

aShemaleTube

TS 444

Categories: amateur, anal, asian, big cock, cumshot, femboy, homevideo, masturbation, sissy, solo

aShemaleTube

Emo Janeth Ridmoon masturbate

Categories: amateur, anal, crossdressing, emo, homevideo, ladyboy, latex, latina, lingerie, masturbation

KeekAss

Sissy super-bitch screwed rigid by a cop homie

Categories: amateur, anal, big cock, bitch, blowjob, cop, crossdressing, cute, femboy, hd

ShemaleMovie

Femboy vibrator, vibrator cumshot

Categories: ass, bbw, beauty, big ass, black, crossdressing, cum, cumshot, fat, femboy

aShemaleTube

Lostwind Comp5

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

xHamster

Cute tran in bikini strips naked in public wearing heels anal plug and hot tight ass

Categories: american, anal, ass, big ass, bikini, crossdressing, cute, dress, feet, fetish

aShemaleTube

Fuck my Swedish ass and cum deep inside

Categories: ass, barebacking, blonde, creampie, crossdressing, cum, cumshot, homevideo, lingerie, mature

aShemaleTube

Tranny Cassidy Quinn wears diapers after spanking

Categories: 3some, diaper, fetish, hd, pornstar, sissy, spanking, tgirl, tranny, transsexual

aShemaleTube

Slut Sissy Samana (CB:showlover12) edging and cumming

Categories: crossdressing, cum, cumshot, edging, hd, homevideo, lingerie, masturbation, pantyhose, sissy