Sissy Shemale Videos Added This Month » 5

TrannyOne

Sammi Smith - Sissy Caption Sotry

Categories: gay, homevideo, sissy

AlphaPorno

Shemales share ripe pussy in restless threesome

Categories: 3some, anal, big tits, blowjob, doggystyle, face sitting, fake tits, hairy, hd, kissing

aShemaleTube

Compilation bbc taking dick after eating dick real sissy shi

Categories: big black cock, compilation, dick, hd, sissy, slut

xHamster

Sissy femboy loves blowjob and getting fucked and swallowing cum

Categories: amateur, big ass, big black cock, blowjob, crossdressing, cum, cum swallowing, domination, escort, femboy

aShemaleTube

Young femboy cumshot compliation

Categories: amateur, big cock, compilation, cumshot, femboy, hd, homevideo, lingerie, masturbation, sissy

xHamster

Trans Girlfriend Made Into Dominatrix

Categories: amateur, crossdressing, domination, dominatrix, fetish, girlfriend, hd, latex, sissy, solo

xHamster

Mtf Big Tit Asian Redhead Impregnablelexa and Wolfdaddy901 Fuck at a Fans House

Categories: amateur, american, anal, asian, barebacking, bbw, big tits, creampie, femboy, hd

aShemaleTube

CD Bride With Throbbing Butt Plug Masturbates to Sexy CD

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

aShemaleTube

Sissy slut fucks her dildo

Categories: amateur, anal, ass, blonde, crossdressing, dildo, femboy, hd, lingerie, masturbation

aShemaleTube

White lace bodystocking and red high heels

Categories: blonde, bodystocking, crossdressing, femboy, fetish, hd, high heels, lace, ladyboy, lingerie

aShemaleTube

Playing in my leopard print bodystocking

Categories: big cock, bodystocking, crossdressing, femboy, fetish, hd, ladyboy, lingerie, masturbation, pov

xHamster

Latest Live Sex Show Online Recordings, Gigi and Dave, Shemale and Man Couple, POV, Behind the Scene, Webcam Sex, 2025-06-16 3

Categories: blowjob, british, couple, girlfriend, hd, mature, pov, sissy, webcam

aShemaleTube

Mommy Making Her Sissy Cum

Categories: amateur, anal, cum, lingerie, masturbation, mom, sissy, small cock, stockings, toys

HClips

Mistress Sucks Off Bloom And Spits Cum Into Her Own Mouth 7 Min - Sissy Jessica

Categories: amateur, blonde, blowjob, brunette, close up, cum, cum swallowing, cumshot, deep throat, facial

aShemaleTube

Lubricated up buttfuck have fun — myLanaSky

Categories: amateur, anal, assfucking, crossdressing, cumshot, femboy, funny, homevideo, masturbation, sissy

aShemaleTube

Goth Transgirl Sucks Her Cock and Moans in Close-Up Cam Session

Categories: amateur, anal, big cock, close up, dick, femboy, goth, masturbation, moaning, sissy

aShemaleTube

Think I still need a lot of training

Categories: bitch, crossdressing, hd, sissy

xHamster

Huge 12in Dildo Fuck Ass Compilation Xxiii-v

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

aShemaleTube

Sissy In Pink Lingerie Sucking

Categories: amateur, blonde, blowjob, crossdressing, hd, homevideo, lingerie, pov, sissy, stockings

xHamster

Fuck Machine Anal Slut

Categories: anal, ass, big ass, fucking machine, hd, masturbation, sissy, slut, small cock

xHamster

Pantyhose Faggot

Categories: amateur, crossdressing, dildo, german, hd, lingerie, masturbation, mature, pantyhose, sissy

aShemaleTube

Lush Latina tgirl flaunting her enormous cock with seductive moves on cam

Categories: amateur, big cock, dick, homevideo, latina, masturbation, pov, sissy, small tits, solo

xHamster

Shana Webcamfun

Categories: amateur, belgian, crossdressing, dildo, fucking machine, hd, lingerie, masturbation, sissy, solo

xHamster

Sissy on Cam

Categories: amateur, anal, belgian, crossdressing, fucking machine, hd, lingerie, masturbation, sissy, solo

aShemaleTube

Dildo makes little dick leak under skirt

Categories: anal, crossdressing, cum, dick, dildo, hd, lingerie, sissy, skirt, small cock

aShemaleTube

BNWO: This is what YT Defeat looks like

Categories: amateur, compilation, crossdressing, ebony, hd, interracial, lingerie, sissy, small cock, teen (18+)

aShemaleTube

Hardcore gaping and assfucking video that unfortunately had no sound captured

Categories: amateur, anal, assfucking, big ass, crossdressing, femboy, gaping hole, hardcore, hd, prolapse

aShemaleTube

Creamy anal adventure ft Sissy Kenzie Star

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

aShemaleTube

Spit Slave Cleaning Duties Part 1 of 2 Clean Jessicas Spit And Heels

Categories: amateur, anal, blonde, cleaner, domination, feet, femboy, femdom, fetish, high heels

aShemaleTube

Mature CD Janis Wylde fresh out of the shower

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

aShemaleTube

Jenny fucked by client

Categories: amateur, big black cock, big cock, crossdressing, femboy, hd, homevideo, interracial, sissy, stockings

aShemaleTube

Anal sex is Gender-neutral by BerlinaFilms

Categories: anal, hd, music, sissy, slut

xHamster

Dreaming of a pretty girl to fuck

Categories: amateur, anal, ass, barebacking, blonde, blowjob, cum in mouth, cumshot, fantasy, handjob

aShemaleTube

Sashas New Mistress

Categories: blonde, domination, femboy, lingerie, masturbation, mistress, sissy, toys

xHamster

Teen Sissy Already Knows Her Place

Categories: anal, barebacking, big cock, blonde, blowjob, cumshot, hd, lingerie, old, sissy

aShemaleTube

Goth Sissy Jade Madison Deepthroating Dick - Compilation 5

Categories: amateur, american, anal, beauty, big ass, big cock, blowjob, compilation, crossdressing, deep throat

aShemaleTube

Sissy coming home from work

Categories: amateur, anal, anal toying, bdsm, crossdressing, cuckold, feminization, fetish, high heels, homevideo

xHamster

BIG BOOTY Femboy AMATEUR Model Sissy Kitty Cross Hot Outfit Big Yummy Ass Smooth Skin Shiny Feminiz

Categories: amateur, ass, big cock, booty, compilation, cum, cum in mouth, cumshot, dancing, femboy

xHamster

Cdzinha masturbating hot

Categories: anal, anal toying, brazilian, dildo, femboy, hd, huge dildo, lingerie, masturbation, sissy

xHamster

Trans Cosplayer Rides and Cums

Categories: amateur, beauty, cosplay, crossdressing, cum, cumshot, dildo, hd, masturbation, riding

aShemaleTube

I am only allowed to cum while caged

Categories: amateur, blonde, crossdressing, cum, femboy, hd, lingerie, sissy, solo

aShemaleTube

Rafaelita Sissy (JUGANDO RICO CON MI DILDO LARGO)

Categories: crossdressing, dildo, hd, sissy

aShemaleTube

Goth Crossdresser Jade Madison Sucking Cock - Compilation 4

Categories: amateur, american, big cock, blowjob, compilation, crossdressing, dick, goth, hd, lingerie

aShemaleTube

Cam Crest is a Sissy Whore for Sindy Memo’s Huge Dick

Categories: anal, asian, babe, bdsm, big cock, crossdressing, cum, cumshot, hd, huge cock

aShemaleTube

Ella Lets Mommy Masturbate Her

Categories: blowjob, cumshot, hd, masturbation, mom, sissy

aShemaleTube

Joi humiliation fag

Categories: humiliation, joi, sissy

aShemaleTube

Wow, how delicious is it when it's wet?

Categories: amateur, brazilian, dildo, femboy, fingering, hd, high heels, latina, pussy, sissy

aShemaleTube

Indian Sissy Turned Out by Pimp into Street Hooker Motel Hooker

Categories: amateur, asian, crossdressing, desi, hd, indian, motel, sissy, slut, street

aShemaleTube

Aubrey

Categories: anal, barebacking, big cock, big tits, blonde, blowjob, cum in mouth, femboy, hd, lingerie

Pornstars: Aubrey Kate

xHamster

SissyCDMish - Compilation of all my slutwalking this year

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

xHamster

fellate

Categories: blowjob, cum in mouth, dutch, hd, homevideo, ladyboy, lingerie, sissy, stockings

aShemaleTube

In chastity fucking the sissy worthless cum from clitty

Categories: amateur, anal, cage, cum, dildo, femboy, fishnet, hd, lingerie, sissy

aShemaleTube

Cumpilation of hot femboys, shemales & trans with bonus final video

Categories: amateur, big cock, compilation, cumshot, femboy, hd, latina, sissy, small tits, teen (18+)

aShemaleTube

Jerking and Face Sitting Her Sissy

Categories: amateur, crossdressing, cumshot, domination, face sitting, femboy, jerking, lingerie, masturbation, sissy

KeekAss

Sissy Jessica Bloom vs Funzze Prodding Cork And Electro-hitachi in Man meat Box V-card

Categories: amateur, anal, ass to mouth, beauty, blonde, buttplug, cage, cumshot, cute, dick

aShemaleTube

Sexy Crossdresser kellycd2022 in sexy lace nightie and fishnets fucking my dildo

Categories: amateur, anal, anal toying, big tits, crossdressing, dildo, fetish, fishnet, hd, high heels

aShemaleTube

Two hot Futanari's stroking and teasing on cam

Categories: big cock, couple, futanari, hd, latina, masturbation, sissy, skirt, stroking, tease

aShemaleTube

Terrant

Categories: amateur, anal, blowjob, crossdressing, cumshot, femboy, hd, homevideo, ladyboy, sissy

xHamster

BBC Sissy Fucks a Pillow

Categories: amateur, big ass, big black cock, big cock, crossdressing, femboy, feminization, fetish, hd, ladyboy

HClips

Very Hot Goth Femboy Fucked - Compilation 1 With Jade Madison And Sissy Crossdresser

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

xHamster

sexy shana

Categories: amateur, belgian, fucking machine, hd, homevideo, masturbation, pornstar, sissy, toys, webcam

TrannyOne

Sissy anal homemade

Categories: amateur, anal, big cock, blowjob, brunette, cumshot, gay, hardcore, hd, homevideo

JizzBunker

Know your place sissy

Categories: anal, blowjob, compilation, cumshot, doggystyle, fetish, hardcore, sissy

xHamster

I came with your hard cock fucking me daddy 🥰

Categories: american, anal, anal toying, cum, cumshot, daddies, dick, dildo, femboy, hardcore

aShemaleTube

Relax and take a shower with the femboys

Categories: asian, big cock, compilation, femboy, hd, ladyboy, latina, shower, sissy, webcam

KeekAss

Marina Rosa Feminization Sissy

Categories: amateur, crossdressing, feminization, homevideo, lingerie, sissy

xHamster

Spank and Cumshot Book Show

Categories: amateur, anal, bbw, cumshot, desi, handjob, hd, indian, sissy, spanking

aShemaleTube

Riding dildo in stockings and chucks

Categories: anal, ass, dick, dildo, hd, riding, sissy, stockings

aShemaleTube

Little🦋Whore of Maison Close. CAM[¹¹June²] VaneSsaBiTCHx in Mini-Skirt, Latex & Nylon Stockings,

Categories: amateur, beauty, big cock, crossdressing, escort, european, gaping hole, high heels, latex, lingerie

aShemaleTube

Black PVC

Categories: amateur, anal, ass to mouth, barebacking, black, blonde, blowjob, crossdressing, fetish, hd

aShemaleTube

Nel culo ti farà male

Categories: big cock, sissy

aShemaleTube

Rachael Belle Exposed Chastity Sissy Slut Humiliation 1

Categories: crossdressing, hd, humiliation, lingerie, masturbation, sissy, slut, solo

aShemaleTube

Rachael Belle Exposed Sissy Slut Humiliation 3

Categories: crossdressing, hd, humiliation, masturbation, sissy, slut, small cock, solo, stockings

aShemaleTube

Thrusting anal plug in chastity having analgasms & sissygasms

Categories: amateur, anal, cage, crossdressing, femboy, hd, homevideo, pantyhose, sissy, slut

aShemaleTube

Enchanting Femboy Fantasy: Embracing Elegance with Attitude

Categories: beauty, college, compilation, cosplay, crossdressing, cum, cumshot, fantasy, femboy, ladyboy

aShemaleTube

Shemale Gets a Quickie Anal Creampie After Sucking Dick

Categories: amateur, american, anal, barebacking, big tits, blowjob, creampie, cum, cumshot, dick

aShemaleTube

Dp in chasty and glass anal plug

Categories: amateur, anal, cage, crossdressing, dildo, double penetration, femboy, hd, homevideo, sissy

aShemaleTube

Sissy Kenzie Star fucks her horny little ass

Categories: anal, ass, dildo, gaping hole, hd, sissy

aShemaleTube

Sissy Clitty Handjob

Categories: cage, clit, dick, goddess, handjob, hd, humiliation, pussy, sissy, slut

aShemaleTube

The Bad Girl cam

Categories: amateur, anal, ass to mouth, big cock, big tits, crossdressing, fetish, hd, homevideo, sissy

ShemaleMovie

Joselynne Crossdresser gets drilled with my toys in the second part

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

xHamster

Making a Custom Video for a Fan.mp4

Categories: amateur, american, barebacking, big ass, blowjob, creampie, cum, hd, interracial, masturbation

aShemaleTube

Two incredible cute TGirls couple give blowjob handjob and fuck camshow

Categories: amateur, anal, blowjob, couple, cute, handjob, homevideo, sissy, teen (18+), tgirl

ShemaleMovie

Amateur crossdresser Patty shows off in sexy lingerie and gets off

Categories: amateur, anal, anal toying, crossdressing, dildo, european, lingerie, masturbation, sissy, stockings

xHamster

She just wants to please her daddy by giving him her dirty asshole

Categories: amateur, anal, ass, barebacking, big cock, colombian, creampie, crossdressing, daddies, dirty

ShemaleMovie

Big cock t-girl Lucy goes bareback with MILF Lisa in intense anal action

Categories: amateur, anal, barebacking, big cock, blowjob, british, crossdressing, huge cock, milf, sissy

XXXDan

Streaching My Sissy Ass to Be Ready for Real Cocks - Sissygasm

Categories: amateur, anal, ass, big ass, big cock, dick, dildo, hardcore, masturbation, mature

XXXDan

Big Tits Asian American Sissy Tranny Trap Used by Her Daddy Dominant Part 3 of 3

Categories: amateur, american, anal, asian, bdsm, big tits, creampie, daddies, gay, interracial

aShemaleTube

Sissy in red chastity, rides dildo

Categories: anal, dildo, goth, homevideo, lingerie, masturbation, mexican, pantyhose, sissy, transsexual

ShemaleMovie

Double the fun with two dildos in my pussy, taking them deep

Categories: amateur, anal, anal toying, asian, crossdressing, dildo, femboy, funny, ladyboy, masturbation

aShemaleTube

Sissy clit cum

Categories: clit, cum, cumshot, femboy, fetish, hd, pantyhose, sissy, solo

aShemaleTube

Guiding light

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

ShemaleZ

Trans Fucks Asian Tgirl Into A Dick-down Stupor With Ria Bentley

Categories: american, anal, asian, assfucking, barebacking, brunette, crossdressing, dick, hd, lace

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

xHamster

My Name Is Pai-chan, a Japanese Femboi Stripper

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

xHamster

Naughty Wife wears stockings and full cut panties

Categories: amateur, bra, british, crossdressing, hd, high heels, lingerie, masturbation, mature, naughty

JizzBunker

Crossdresser sissy femboy trans shemale college teen

Categories: babe, blonde, college, crossdressing, femboy, masturbation, sissy, teen (18+), transsexual

VideoSection

Intense anal experience with a sexy amateur crossdresser and extreme pleasures

Categories: amateur, anal, anal toying, babe, bdsm, beauty, cosplay, crossdressing, european, extreme

aShemaleTube

Annemieke in red lingery outdoor in public giving blowjob

Categories: blowjob, caught, cute, dick, hd, outdoor, public, sissy

xHamster

my fucker is opening my pussy like a woman. My pussy is burning from the fluids that come out. I squirt from

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

XXXDan

Sissy Slut Michelle in a New Lingerie Preparing Before a Date in a Hotel of Turkish Bodrum

Categories: anal, crossdressing, cumshot, fetish, handjob, hotel, lingerie, masturbation, pantyhose, shower

xHamster

Hard Hole Pegging

Categories: amateur, anal, couple, cum, domination, hd, pegging, pissing, sissy

aShemaleTube

night walk - public crossdressing

Categories: amateur, crossdressing, european, fetish, high heels, latex, outdoor, polish, pov, public

xHamster

Noisy Creampies in Ts Milf

Categories: amateur, american, anal, beauty, big cock, black, creampie, crossdressing, cum, ebony

aShemaleTube

Black top stockings and hot little black dress

Categories: black, blonde, crossdressing, dress, femboy, fetish, hd, ladyboy, lingerie, masturbation