Sissy Shemale Videos Added This Month » 11

ShemaleMovie

Joselynne the crossdresser enjoys a session with her favorite toys

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

ShemaleMovie

Dazzling crossdressing princess takes on trans Kelsey Masters in a sizzling compilation

Categories: amateur, american, anal, ass, babe, barebacking, bdsm, beauty, big ass, big cock

aShemaleTube

The P song for my Sissy-ster PMV

Categories: compilation, crossdressing, hd, sissy, solo, toys

aShemaleTube

Fucking Goth Sissy Jade Madison - Compilation 1

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

aShemaleTube

sexy crossdresser kellycd2022 doing another friday evening cam session in tan seamless pantyhose

Categories: amateur, big tits, crossdressing, cumshot, fetish, hd, high heels, masturbation, mature, outdoor

Pornstars: Friday

XXXDan

Daddy and sissy JOI

Categories: amateur, big cock, cumshot, daddies, fetish, joi, masturbation, sissy, solo, tattoo

aShemaleTube

Asian femboy hand job

Categories: asian, cum, femboy, handjob, pretty, sissy

aShemaleTube

Trans in lingerie and heels cums a lot

Categories: amateur, big ass, crossdressing, cum, cumshot, fetish, hd, high heels, homevideo, ladyboy

HClips

Fucking Goth Sissy Compilation 2 With Jade Madison And Sissy Crossdresser

Categories: amateur, american, anal, assfucking, brunette, compilation, crossdressing, fishnet, goth, hd

VideoSection

Wild girl in high heels gets naked

Categories: european, high heels, nude, sissy, small tits, wild

ShemaleMovie

Supersizecd indulges in chubby shemale fun with toys

Categories: american, ass, bbw, big ass, chubby, cumshot, fat, funny, masturbation, sissy

xHamster

Dirty Feet Soft Posing 2

Categories: amateur, blonde, crossdressing, cute, dirty, european, feet, german, hd, lingerie

xHamster

Slutty Tranny Shoplifter Fucked by Police

Categories: 3some, amateur, anal, barebacking, british, cop, crossdressing, cum in mouth, deep throat, face fucking

aShemaleTube

White Dress, Pink Cami and Boots (enhanced)

Categories: amateur, blonde, boots, crossdressing, dress, hd, homevideo, latina, lingerie, sissy

aShemaleTube

Blonde in leopard print bodystocking

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

VideoSection

I crave a pipe to fill me up and make me squirt in my sundress

Categories: anal, bbw, close up, crossdressing, cum, cumshot, jizz, masturbation, oiled, orgasm

ShemaleZ

Blonde Sissy Gets Fucked In Her Onesie

Categories: anal, assfucking, barebacking, blonde, deep throat, hd, nylon, pov, sissy, stockings

ShemaleMovie

Amateur sissy Kimbilly gets dominated by a nasty shemale

Categories: amateur, american, anal, babe, bdsm, beauty, big black cock, big cock, black, brutal

aShemaleTube

SissyCDMish - Compilation of all my slutwalking this year

Categories: amateur, anal, compilation, crossdressing, femboy, fetish, fishnet, hd, high heels, homevideo

aShemaleTube

Dildo fuck part 2

Categories: amateur, anal, anal toying, crossdressing, cumshot, dildo, hd, homevideo, mature, sissy

aShemaleTube

Femboy freya_goddes strokes her cock and fingers ass

Categories: ass, big cock, dick, femboy, fingering, masturbation, sissy, solo, wanking

ShemaleMovie

Trixy Bunny’s sexy Easter fantasies in stunning lingerie

Categories: amateur, babe, beauty, big cock, bunny, crossdressing, fantasy, femboy, high heels, huge cock

xHamster

Hot Trans Bailey Wilde Fucked Doggystyle While in Chastity

Categories: amateur, american, anal, barebacking, big ass, crossdressing, cum, doggystyle, femboy, feminization

xHamster

Beautiful Sissy Slut Anal Orgasm

Categories: anal, beauty, big black cock, compilation, cumshot, hd, masturbation, orgasm, pretty, sissy

aShemaleTube

British tranny gets a MASSIVE facial

Categories: amateur, blowjob, british, crossdressing, cum, cumshot, dick, facial, pov, sissy

aShemaleTube

Best Shemale Sissy Cum Compilation

Categories: amateur, anal, compilation, cum, cumshot, femboy, hd, homevideo, sissy, strap-on

xHamster

You Want See More?

Categories: amateur, crossdressing, european, femboy, german, hd, outdoor, public, sissy, solo

xHamster

I feel great wearing my sexy dress and playing with my pussy. I want a fucking orgasm inside me. Is that bad?

Categories: anal, bbw, big tits, close up, crossdressing, cum, cumshot, dirty, dirty talk, dress

aShemaleTube

Strawberry blonde in pink costume and bra

Categories: amateur, blonde, bra, costume, crossdressing, femboy, hd, ladyboy, lingerie, pantyhose

aShemaleTube

Indian sissy getting ready for all the dicks in the neighborhood

Categories: cum, dick, femboy, hd, indian, sissy, slut, small cock

HDSex

Femboy gets pegged good

Categories: amateur, american, anal, anal toying, babe, bdsm, beauty, blowjob, crossdressing, cum

aShemaleTube

Deadly Finish 😂💦

Categories: amateur, blonde, hd, masturbation, sissy, small cock, small tits, solo, teen (18+), webcam

aShemaleTube

Bigdaddy8inchz and Sissy Erika Blow and Jerk Each Other off

Categories: amateur, american, big black cock, blowjob, couple, crossdressing, face fucking, homevideo, interracial, mature

aShemaleTube

Sissy Rides Big Toy Until Cum

Categories: anal, crossdressing, cum, cumshot, hd, latex, sissy, solo, toys

aShemaleTube

Brunette in black pantyhose and tight red dress

Categories: amateur, black, brunette, crossdressing, dress, femboy, hd, ladyboy, lingerie, mature

aShemaleTube

massive cock destroys my ass and creampie

Categories: amateur, anal, ass, barebacking, big ass, big cock, creampie, crossdressing, cumshot, doggystyle

VideoSection

Trap tits, trap bareback

Categories: amateur, american, anal, barebacking, bbw, creampie, cum, jizz, missionary, riding

aShemaleTube

Stepmom Rileydix and her yummy ass is all you need

Categories: amateur, anal, ass, big ass, crossdressing, granny, hd, lingerie, masturbation, mature

aShemaleTube

Alone in Camera

Categories: amateur, anal, crossdressing, femboy, hardcore, ladyboy, lingerie, sissy, solo, teen (18+)

aShemaleTube

Latest Live Sex Show, 02.06.2025 Ep3

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

aShemaleTube

Latest Live Sex Show 02.06.2025 Ep4

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

HClips

Perfect Sissy Brunette Hard Anal Destroyed By Actorfab

Categories: amateur, anal, assfucking, brunette, deep throat, french, hd, sissy, throat

xHamster

Huge 12in Dildo Fuck Ass Compilation Xxiii-v

Categories: anal, assfucking, big ass, compilation, dildo, fucking machine, hd, huge dildo, masturbation, milf

aShemaleTube

Bikini Sissy CD getting ass fucked and gaped

Categories: amateur, anal, assfucking, big ass, bikini, crossdressing, extreme, femboy, fucking machine, gaping hole

aShemaleTube

So Pretty! And cum too!

Categories: amateur, cum, femboy, fetish, lingerie, pretty, sissy

aShemaleTube

Nikki Loves Sex (pov)

Categories: amateur, barebacking, blowjob, british, crossdressing, homevideo, ladyboy, pissing, pornstar, pov

Pornstars: Nikki Sexx

xHamster

Huge Black Futa Dominates Sissy male - Anais57

Categories: anal, anime, big cock, black, croatian, domination, futanari, hd, huge cock, ladyboy

xHamster

He fucks me in every room before breeding me

Categories: amateur, anal, barebacking, big black cock, big cock, blowjob, creampie, crossdressing, cum, femboy

VideoSection

Sissy crossdresser fucked bbc, deep anal bbc gangbang

Categories: anal, ass, big black cock, big cock, blowjob, crossdressing, deep throat, gangbang, ladyboy, sissy

xHamster

Skinny Blonde Femboy Riding Cock

Categories: amateur, anal, beauty, big cock, blonde, crossdressing, cum, dick, dildo, femboy

xHamster

Amateur Crossdresser Teen Riding Cock in Bathtub

Categories: amateur, anal, bathroom, beauty, big cock, blonde, crossdressing, cum, dick, dildo

xHamster

Hot Crossdresser Fucked with HUGE Strapon

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

xHamster

Bubble Butt Fishnets Femboy Faggot Inflatable Knotted Dildo Part II

Categories: american, anal, anal toying, ass, big ass, big cock, bitch, crossdressing, cum, cumshot

xHamster

Fem (boy) in Women's Clothing Rips His Ass

Categories: amateur, anal, ass, boy, crossdressing, cumshot, dildo, femboy, hd, ladyboy

xHamster

sissy cum collection

Categories: amateur, big cock, compilation, crossdressing, cum, cum in mouth, cumshot, dick, feminization, hd

xHamster

Trans Bailey Wilde Fucking Trans Kelsey Masters

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

xHamster

Hot Crossdresser in Crotch Ripped Yoga Pants Fucks TS Kelsey Masters

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

XXXDan

Older Matured sissy CD out on the balcony Trying to not get caught

Categories: amateur, anal, balcony, big ass, caught, crossdressing, high heels, lingerie, masturbation, mature

aShemaleTube

Sissy Jacqueline Vorstellung

Categories: blowjob, crossdressing, cum in mouth, pantyhose, sissy

xHamster

Trixy in Red Shows How to Use Her Tool

Categories: amateur, anal, crossdressing, cum, dick, femboy, hd, jerking, masturbation, mature

XXXDan

Sissy Maid Rides Her Doll in Chastity and Has a Sissygasm

Categories: amateur, anal, big cock, cosplay, crossdressing, dildo, doll, hardcore, lingerie, maid

aShemaleTube

Michelli cdzinha sissy crossdresser and bbc

Categories: amateur, anal, big ass, big black cock, big cock, crossdressing, ebony, femboy, hd, interracial

HDSex

Sfw, trans gender, outdoor

Categories: amateur, crossdressing, european, feet, high heels, lingerie, outdoor, pov, sissy, stockings

JizzBunker

Pink Sissy in Self Bondage Gets Locked to Her Doll and Fucked Hard by Machine

Categories: amateur, anal, bdsm, big cock, blowjob, bondage, crossdressing, dildo, doll, hardcore

xHamster

Pissind and masturbating in my bathroom

Categories: amateur, anal, bathroom, blowjob, cumshot, dildo, german, hd, lingerie, masturbation

xHamster

Swimsuit Mermaid Bondage Outdoor

Categories: asian, bdsm, bondage, crossdressing, cum, fetish, gagging, hd, hijab, indonesian

xHamster

Nylon Sissy Slut Michelle Wake up at the Hotel After a Date on Vacation in Turkey

Categories: anal, bathroom, beauty, crossdressing, cum, cumshot, femboy, hd, hotel, lingerie

HDSex

Get fucked, see, amateur bareback

Categories: amateur, anal, barebacking, big black cock, big cock, blowjob, condom, crossdressing, femboy, gaping hole

xHamster

Sissy chastity dildo

Categories: anal, crossdressing, dildo, fetish, french, hd, high heels, latex, sissy, solo

xHamster

Crossdresser Bailey Wilde Fucked by Sex Machine

Categories: amateur, american, anal, big ass, crossdressing, femboy, hd, lingerie, sissy, teen (18+)

xHamster

Blonde Crossdresser Fucked Missionary

Categories: amateur, american, anal, beauty, big ass, blonde, crossdressing, femboy, fetish, hd

VideoSection

Femboy fucked, beautiful transgender

Categories: amateur, american, anal, babe, barebacking, bdsm, beauty, blowjob, crossdressing, domination

xHamster

She knows how to hold my big black cock like a good girl

Categories: amateur, anal, barebacking, big black cock, big cock, colombian, creampie, crossdressing, femboy, hardcore

VideoSection

Assfuck, colombian shemale webcam

Categories: anal, anal toying, ass, assfucking, asslick, blowjob, brutal, colombian, couple, cum

xHamster

CD in Sissy Mode and Home Alone Playing for Fun

Categories: amateur, anal, beauty, big ass, big cock, black, canadian, crossdressing, funny, hd

xHamster

I play with trans teen slutty ass and then I fuck her

Categories: amateur, anal, ass, big ass, big black cock, big cock, crossdressing, domination, femboy, hd

HDSex

Amateur bareback, throat fucked, 4k porn

Categories: amateur, american, anal, barebacking, blowjob, creampie, cum, daddies, femboy, jizz

xHamster

Ada Paints Lara's Asshole with Her Tasty Cum

Categories: 3d, anal, ass, barebacking, beauty, creampie, cum, cumshot, femboy, futanari

aShemaleTube

Hot and sexy indian house wife sissy

Categories: anal, housewife, indian, lingerie, rough, sissy

xHamster

Useless sissy cock tied to pussy! Piss and cum like a girl!

Categories: abuse, bathroom, bdsm, cum, cute, dick, femboy, german, hd, humiliation

aShemaleTube

Cumming with dildo in ass

Categories: anal, ass, crossdressing, cum, dildo, femboy, hd, homevideo, masturbation, sissy

xHamster

Feminized and Pegged after Girls Night Out

Categories: amateur, american, anal, bdsm, beauty, big cock, cum, domination, femboy, femdom

aShemaleTube

Posing

Categories: gay, hd, posing, sissy, slut, striptease, tease, thong

aShemaleTube

Emilly Weickert - The Destroyer

Categories: anal, barebacking, big ass, big cock, big tits, creampie, domination, ebony, hd, homevideo

xHamster

Allure Caught in Fishnet Stockings

Categories: amateur, big cock, blowjob, caught, couple, crossdressing, dick, feet, fetish, fishnet

xHamster

Patricia Wolford - Self Anal fisting

Categories: amateur, anal, anal fisting, crossdressing, feet, femboy, feminization, fetish, german, hd

HDSex

Sissy crossdresser, crossdress, crossdresser bondage

Categories: anal, big cock, blowjob, bondage, crossdressing, cumshot, dildo, high heels, sissy, stockings

ShemaleMovie

Venezuelan, shemale fucks shemale

Categories: amateur, anal, ass, asslick, big cock, blowjob, brutal, couple, cum, homevideo

xHamster

Goth Crossdresser Jade Madison Sucking Cock - Compilation 2

Categories: amateur, american, anal, barebacking, big ass, big cock, blowjob, compilation, crossdressing, cute

HDSex

My tiny dick made me turn into a sissy

Categories: anal, ass, asslick, blowjob, bukkake, creampie, cum, cum in mouth, cumshot, double penetration

aShemaleTube

Fucked by a big dildo

Categories: amateur, anal, crossdressing, dildo, hd, mature, sissy, solo, stockings, toys

HClips

Big Tits Asian American Sissy Tranny Trap Played With By Her Stepdaddy Dominant Of 3

Categories: amateur, american, anal, asian, assfucking, big ass, big tits, booty, booty shake, deep throat

xHamster

BIG COCK blonde big tits shemale in lingerie Tiffany Kitten fucks fleshlight and spurts a huge cumshot on her high heels shoes C

Categories: amateur, big cock, big tits, blonde, crossdressing, cum, cumshot, feet, fleshlight, hd

xHamster

Chubby Crossdresser fucked by two big dildos

Categories: anal, anal toying, bbw, chubby, crossdressing, dildo, fishnet, hd, high heels, latina

xHamster

Our First Meeting Me and Karl

Categories: amateur, anal, asian, big cock, couple, crossdressing, cum, dick, hd, ladyboy

HClips

Disney Princess Twink: Owned And Used By Dom Nathan With Sissy Crossdresser

Categories: amateur, big cock, colombian, crossdressing, dick, domination, facial, hd, lace, ladyboy

xHamster

Dreamz

Categories: amateur, beauty, big cock, crossdressing, fantasy, hd, high heels, ladyboy, lingerie, nylon

xHamster

I Love to Fuck Hard...

Categories: anal toying, crossdressing, dick, dildo, greek, hd, high heels, huge dildo, pantyhose, riding

aShemaleTube

outdoor public slutwalk bottomless flashing tits

Categories: amateur, anal, ass, barebacking, big ass, big cock, cumshot, doggystyle, fetish, flashing

xHamster

Melanie Bee Sissy slut alone at home

Categories: amateur, anal, anal toying, crossdressing, german, hd, homevideo, masturbation, sissy, slut

HDSex

Underwear, gothic, anal masturbation

Categories: anal, dildo, goth, lingerie, masturbation, pantyhose, sissy, toys, underwear

xHamster

Huge 12in Dildo Fuck Ass Compilation Xxiii-xiii

Categories: anal, assfucking, big ass, compilation, cumshot, dildo, fucking machine, hd, huge dildo, masturbation

xHamster

Trans Sissy SAMUS Cosplay gets Double Penetration in her Fat Ass Until she gets Gaped

Categories: amateur, anal, anal toying, ass, beauty, big ass, blonde, cosplay, crossdressing, dildo

xHamster

Desi Gand Ki Garmi, kumuk Jawani

Categories: amateur, anal, anal toying, barebacking, big ass, boy, close up, desi, femboy, gay

aShemaleTube

Joselynne Crossdresser Change Outfit In 2013 Part Two Another Angle Cam

Categories: amateur, big ass, big cock, crossdressing, feminization, high heels, latina, lingerie, mature, mexican

ShemaleMovie

Trans shemale, fellatio

Categories: amateur, anal, babe, barebacking, beauty, blowjob, british, couple, cum, girlfriend

xHamster

A is for Apple, B is for Bottle...

Categories: amateur, anal, ass, austrian, big ass, big cock, crossdressing, cute, femboy, fetish

xHamster

I Turn My Sissy on so She Fucks Me

Categories: amateur, beauty, couple, crossdressing, french, hd, lingerie, milf, sissy, slut

aShemaleTube

Second Blowjob Video

Categories: amateur, blowjob, crossdressing, cum in mouth, hd, homevideo, interracial, lingerie, sissy

xHamster

Plugged and Chained

Categories: beauty, chained, fishnet, hd, mature, pissing, sissy, solo, transsexual

aShemaleTube

In fishnets anal plug caged up just being a good sissy

Categories: amateur, anal, cage, crossdressing, cum, femboy, fishnet, gaping hole, hd, lingerie

aShemaleTube

Teasing, Stroking, Sucking, Fucking, & Cumming Compilation

Categories: anal, blowjob, compilation, cum, cum in mouth, cumshot, hd, lingerie, masturbation, pantyhose

HClips

He Fucked My Hole Hard And Filled It With Cum

Categories: amateur, anal, assfucking, barebacking, crossdressing, cum, hd, lace, lingerie, sissy

aShemaleTube

full naked public slutwalk truckstop chastity heels

Categories: amateur, big ass, caught, crossdressing, exhibitionist, fetish, flashing, hd, high heels, nude

aShemaleTube

I Bring a Man over

Categories: amateur, big ass, crossdressing, hd, interracial, lingerie, sissy, small cock

xHamster

Fucking Goth Sissy Jade Madison - Compilation 1

Categories: amateur, american, anal, barebacking, big ass, compilation, crossdressing, cute, femboy, goth

xHamster

Big Anal Pounding for a Sissy on the Couch

Categories: anal, barebacking, big black cock, blowjob, couch, creampie, crossdressing, cumshot, femboy, hd

HClips

Sissy Lara White Crossdresser Lingerie Heels Femboy Shemale Trans Tranny Tgirl Trap 29

Categories: amateur, crossdressing, femboy, hd, high heels, jerking, lace, lingerie, masturbation, sissy

ShemaleMovie

Transgender, goth sissy

Categories: american, anal, big cock, goth, lingerie, sissy

xHamster

Crossdresser Fernanda Gomez in Vintage Style Lingery Like a Slut

Categories: amateur, chilean, crossdressing, hd, lingerie, mature, sissy, slut, solo, stockings