Sissy Shemale Videos » 46

aShemaleTube

Just a dumb sissy who took it too far and still hasn't kissed all the boys...

Categories: bikini, bra, hd, kissing, panties, sissy, skirt, striptease, tranny, transsexual

TrannyOne

SOS Sissy Faggot PMV Classic

Categories: big cock, classic, gay, hd, homevideo, sissy

xHamster

Gorgeous Femboy Goddess Fucking Trans Kelsey Masters - Compilation 6

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

xHamster

Sexy Crossdresser Kellycd2022 outdoors in tan seamless pantyhose and leopard print backless dress

Categories: amateur, big cock, british, crossdressing, dress, hd, ladyboy, masturbation, mature, outdoor

aShemaleTube

gropes

Categories: amateur, crossdressing, femboy, groping, hd, homevideo, ladyboy, lingerie, mature, sissy

KeekAss

Sexy Tranny Jerks Cock Online

Categories: amateur, beauty, big ass, boyfriend, dick, girlfriend, homevideo, jerking, masturbation, nylon

aShemaleTube

Dizzys dildo oral training in the mirror

Categories: crossdressing, dildo, hd, mirror, oral, sissy, tgirl, tranny

aShemaleTube

dany_monster_cock

Categories: big cock, brunette, dick, hd, homevideo, latina, lingerie, long hair, masturbation, sissy

aShemaleTube

Sissy humiliation

Categories: bimbo, humiliation, sissy

aShemaleTube

Donna Rhinestone loves getting fucked by BBC

Categories: big black cock, sissy, slut

aShemaleTube

Jamie Jardon crossdresser masturbation compilation with JOI and cumshots

Categories: big cock, big tits, compilation, crossdressing, cumshot, hd, joi, masturbation, sissy, stroking

xHamster

I fool my stepcousin's when he is visiting the house

Categories: amateur, anal, asslick, blowjob, colombian, crossdressing, cum, doggystyle, femboy, hardcore

aShemaleTube

Sissy Quiz Test (2 Question) by BerlinaFilms

Categories: ass, compilation, fingering, hd, music, sissy

ShemaleMovie

Sissy rides gear stick with love until cumshot to show car appreciation

Categories: anal, ass, brutal, car, cum, cumshot, femboy, fishnet, fisting, homevideo

ShemaleMovie

Intimate POV anal session behind the scenes with Cassandra Lovit

Categories: amateur, anal, ass, behind the scenes, couple, crossdressing, lingerie, pornstar, pov, sissy

Pornstars: Cassandra

xHamster

PVC Leotard Magical girl Breathplay Trial: Shower cap

Categories: amateur, bondage, breath play, canadian, cosplay, fetish, hd, homevideo, latex, masturbation

xHamster

Only a locked sissy slut! Fucked with a penis cage and cummed on!

Categories: anal, blonde, blowjob, cage, cumshot, deep throat, dick, doggystyle, german, hd

xHamster

Dominatrix Puts Corset on Sissy Maid and Fucks Her

Categories: amateur, american, bdsm, beauty, big cock, corset, crossdressing, cum, domination, dominatrix

KeekAss

More dancing, dirty dancing and frolicking at being a stripper

Categories: amateur, anal toying, big ass, booty, crossdressing, dancing, dirty, hd, lingerie, milf

aShemaleTube

Man and Woman Putting on Mascara and Fake Lashes

Categories: amateur, american, behind the scenes, cosplay, crossdressing, homevideo, milf, pretty, sissy, teen (18+)

xHamster

Vanessabitchx with Sebastien Rencontre Sur Divinea

Categories: anal, ass, barebacking, beauty, bitch, couple, crossdressing, cute, french, hd

xHamster

Anal training for Sissy Blaire_18. Dominatrix Nika inserts anal beads into her Sissy's little ass.

Categories: anal, beads, dominatrix, fetish, hd, homevideo, sissy, tattoo

aShemaleTube

Sissy Slut fucks ass with huge dildo

Categories: ass, femboy, gay, hd, huge dildo, sissy, slut, transsexual

xHamster

Trans maid serves a huge load

Categories: amateur, beauty, big cock, british, cosplay, cum, cumshot, femboy, hd, maid

KeekAss

Wantabee Sissies getting Dicked down

Categories: amateur, anal, asian, blonde, brunette, compilation, crossdressing, dick, ebony, gay

aShemaleTube

TS 461

Categories: amateur, compilation, crossdressing, cumshot, femboy, homevideo, masturbation, sissy, solo, teen (18+)

xHamster

Sissy pees on her sneakers

Categories: amateur, bathroom, crossdressing, fetish, french, hd, homevideo, pissing, sissy, small cock

ShemaleMovie

Amateur femboy, blonde shemale solo

Categories: amateur, anal, ass, beauty, big ass, big cock, bikini, blonde, british, compilation

xHamster

My First Video of the Year 2019

Categories: beauty, colombian, crossdressing, cum, cumshot, dick, hd, homevideo, ladyboy, latina

xHamster

VERY SEXY Redhead Trans in Lingerie Fucked

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

xHamster

caged sissy trying to get some pleasure

Categories: anal, anal toying, big black cock, black, dick, fishnet, hd, masturbation, sissy, small cock

KeekAss

Transgirl Stroking her Pecker in the Douche

Categories: amateur, anal, beauty, big black cock, big cock, boy, cum, dick, femboy, homevideo

KeekAss

Pulverize Stud Demolishes my Make-Up and Fave Hoodie with Dirty Mouth Pound

Categories: amateur, blonde, blowjob, daddies, dick, dirty, handjob, hd, oral, sissy

aShemaleTube

Sissy slut whore

Categories: hd, oiled, sissy, slut

aShemaleTube

BTS interview with Jennifer Lunden

Categories: amateur, crossdressing, hd, interview, lingerie, sissy, small tits

xHamster

Alison the dirty wet and messy nurse , sploshing

Categories: big tits, boots, british, crossdressing, cum, cumshot, dirty, dirty talk, fetish, hd

ShemaleMovie

Couples enjoying wild encounter with Thai shemale beauty

Categories: amateur, anal, asian, ass, barebacking, bbw, beauty, big ass, big black cock, big cock

xHamster

Cosplay Cutie: Fuckable Fairy Trailer

Categories: amateur, american, bbw, big cock, big tits, chubby, cosplay, cum, cumshot, cute

ShemaleMovie

Anal masturbation, get fucked

Categories: amateur, anal, asian, cosplay, crossdressing, femboy, hardcore, japanese, ladyboy, masturbation

xHamster

Succubus unmask

Categories: american, big tits, bondage, cosplay, crossdressing, domination, european, fetish, lingerie, mask

aShemaleTube

Shirley Early Morning Chat, Wank & Spunk

Categories: brunette, crossdressing, cumshot, fake tits, homevideo, lingerie, masturbation, mature, sissy, stockings

xHamster

Dominatrix Makes Man Dress as Hot Maid and Fucks Her

Categories: amateur, american, anal, bdsm, crossdressing, domination, dominatrix, dress, feminization, fetish

KeekAss

Naughty Ts Chick Masturbates Rigorously

Categories: amateur, anal, beauty, brunette, cute, dick, ebony, homevideo, lingerie, masturbation

KeekAss

My Greedy Rump is Gobbling Cucumber!

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

TrannyOne

Androgynous sissy twink pleasuring a stepdaddys cock again WTF !

Categories: amateur, blowjob, crossdressing, dick, emo, gay, grandpa, hairy, hd, old

aShemaleTube

Hayley Is A Sissy Slut

Categories: amateur, blowjob, cumshot, hd, homevideo, masturbation, sissy, slut

aShemaleTube

Sissy bimbo in lingerie plays with herself

Categories: amateur, big ass, bimbo, crossdressing, dildo, femboy, hd, lingerie, masturbation, sissy

aShemaleTube

Maid costume, using a vibrator on my chastity cage until I squirt

Categories: cage, costume, cumshot, hd, homevideo, maid, redhead, sissy, solo, squirt

KeekAss

Encaged Sissy attempt get gusto by assfuck faux-cock have fun

Categories: amateur, anal, assfucking, crossdressing, dick, dildo, femboy, feminization, funny, hd

ShemaleMovie

Sissy maid gets drenched in imitation cum, dominates her fuck machine, and experiences a sissygasm

Categories: american, anal, blowjob, crossdressing, cum, dildo, jizz, maid, masturbation, sissy

xHamster

Im A BBC Slutttt♠️

Categories: anal, big ass, big black cock, european, homevideo, masturbation, sissy, slut, small cock, teen (18+)

xHamster

Stiletto Heels and Cum After Playing with You

Categories: big cock, crossdressing, cum, cumshot, fetish, handjob, hd, high heels, ladyboy, lingerie

XXXDan

Sissy Lucy in chastity gets ass fucked with huge dildo

Categories: amateur, anal, assfucking, big ass, british, dildo, hardcore, huge dildo, mature, redhead

KeekAss

nude she-male rail immense fuck stick stiff precum close-up mighty jizz flow

Categories: amateur, anal, ass, brunette, close up, cum, cumshot, dildo, hd, homevideo

aShemaleTube

the best femboy booty🌈👄💄👠💖

Categories: big ass, booty, crossdressing, cumshot, femboy, lingerie, masturbation, sissy, solo, toys

ShemaleMovie

Cute sissy Kit69lupin gets tied up and desperately humps a cushion to climax

Categories: amateur, american, anal, anal toying, babe, bdsm, beauty, cum, cute, dildo

xHamster

X-mas night with huge toys and fucking machine

Categories: amateur, anal, anal toying, dildo, fucking machine, hd, huge dildo, masturbation, orgasm, rough

xHamster

SEXIEST Redhead Femboy Fucked Doggystyle

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

HDSex

Sissy slave gets his ass fucked hard in hot lingerie

Categories: amateur, anal, ass, beauty, big ass, big cock, dildo, hardcore, ladyboy, lingerie

xHamster

Slimmie Break

Categories: amateur, beauty, fetish, hd, sissy, smoking, solo

KeekAss

Young Trap Fingering Herself During Solo

Categories: amateur, beauty, dick, femboy, fingering, futanari, hd, homevideo, jerking, lingerie

xHamster

Dominatrix Feminized Roommate Sucks Her Strap On

Categories: amateur, american, anal toying, bdsm, blowjob, cum, dick, domination, dominatrix, fetish

TrannyOne

Amateur Hot Redhead Shemale Deepthroat A Big White Cock And Get Cum In Her Mouth POV

Categories: amateur, anal, ass, blowjob, cum, cum in mouth, cum swallowing, cumshot, deep throat, dick

aShemaleTube

My best asset

Categories: amateur, big ass, big tits, crossdressing, hd, lingerie, redhead, sissy, small cock, stockings

HClips

Feet Slave - Trampling Cumshot Sissy Licks Cum Of Mistresss Feet

Categories: amateur, blonde, cum, cumshot, feet, fetish, hd, licking, sissy, slave

aShemaleTube

Tranny Tgurl smoking slut Sarah Millward

Categories: blonde, crossdressing, fetish, hd, homevideo, lingerie, model, sissy, slut, smoking

xHamster

Rigid3d Intense Sex Hardcore Hot Big Tasty Ass Swallows Huge Monster Cock Hardcore Sex

Categories: amateur, american, asian, ass, big cock, compilation, crossdressing, cum, cum swallowing, cumshot

aShemaleTube

Pute Gay

Categories: amateur, anal, cumshot, gay, hd, mature, sissy, toys

xHamster

Crossdressing Delight: Embrace the Freedom to Express Your Unique Style and Celebrate Individuality, as You Break Boundaries, Ch

Categories: amateur, american, beauty, big ass, blonde, celebrity, crossdressing, fat, hd, homevideo

aShemaleTube

Full body femboy shower expierence with shaving and cumshot

Categories: asian, big ass, cumshot, femboy, fetish, hd, homevideo, masturbation, model, pornstar

Pornstars: Viper

aShemaleTube

Carla x Suzie

Categories: big cock, big tits, blonde, blowjob, crossdressing, sissy

aShemaleTube

Holly smoking and lets you look up her skirt

Categories: amateur, crossdressing, hd, homevideo, lingerie, mature, panties, sissy, skirt, smoking

aShemaleTube

Natural beauty Lizzy teases & cums 💦

Categories: beauty, big tits, cum, cumshot, european, femboy, hd, masturbation, natural tits, sissy

xHamster

Small Dick Sissy Playing with a Fuck Machine - Sissy Captions

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

xHamster

Double Cumshot After Cucumber Ass Fuck

Categories: anal, anal toying, assfucking, beauty, big cock, creampie, cucumber, cum, cumshot, hd

KeekAss

anime joy in rosy delicate stockings

Categories: amateur, anal, anime, ass, big ass, crossdressing, feet, fetish, fishnet, footjob

xHamster

Hot MILF Deep Throating Tan Sissy

Categories: amateur, american, bbw, big clit, big cock, big tits, bisexual, blonde, blowjob, close up

aShemaleTube

Arabic Tranny Mikah Hotel Blowjob

Categories: amateur, arab, blowjob, crossdressing, doll, hd, homevideo, hotel, interracial, pov

TrannyOne

Cute Asian Crossdresser Triss Goth 2

Categories: adorable, asian, crossdressing, cute, goth, hd, lipstick, oriental, sissy, transvestite

aShemaleTube

Joselynne Crossdresser With Dress In Big Ass To Fuck

Categories: amateur, big ass, crossdressing, dress, escort, feminization, high heels, latina, mature, mexican

xHamster

Trixy Maid Fucked Hard - Short

Categories: anal, blowjob, boss, hardcore, hd, maid, masturbation, sissy

xHamster

Beautiful sexy transgender smoking and changing nipple piercing

Categories: bdsm, beauty, big ass, hd, homevideo, indian, nipples, piercing, pornstar, pov

ShemaleMovie

Festive femboy pleasures himself with a massive toy and cums up close

Categories: amateur, anal, ass, big ass, big cock, cosplay, crossdressing, cum, cumshot, dildo

aShemaleTube

Sissy slutSarah in latex dress, smokes, masturbates to cum shot and drinks it

Categories: amateur, big cock, blonde, crossdressing, cumshot, dress, femboy, hd, latex, masturbation

ShemaleMovie

Complete guide to sissy training, feminization, and sissy support

Categories: anal, big black cock, cumshot, feminization, humiliation, pov, sissy

KeekAss

Tasted my jism on web cam Witnessing Porno ! Maddie Styles CB

Categories: amateur, ass, big cock, brunette, crossdressing, cum, cumshot, dick, fetish, handjob

aShemaleTube

White minidress, stockings and pink panties

Categories: amateur, big cock, blonde, crossdressing, dress, femboy, hd, ladyboy, lingerie, masturbation

JizzBunker

Sissy Slut Michelle Relaxes After a Business Day at the Turkish Hotel in Dalaman

Categories: amateur, business woman, crossdressing, cumshot, dildo, hotel, lingerie, masturbation, sissy, slut

HDSex

Converting my straight roommate into my submissive wife

Categories: amateur, anal, asian, babe, beauty, big cock, brutal, crossdressing, femboy, ladyboy

XXXDan

EmmaaaTV German Sissy HOT Dress

Categories: amateur, cosplay, crossdressing, dress, fetish, gay, german, handjob, masturbation, sissy

aShemaleTube

MY LOVE 034

Categories: big tits, chinese, crossdressing, cumshot, hd, ladyboy, lingerie, masturbation, sissy, solo

xHamster

Nuttytouch Delicious Intense Masturbation Tasty Sex Sweet Intense Pleasure Hot Big Ass Fucking Hard

Categories: amateur, american, asian, assfucking, beauty, big cock, crossdressing, cum, hd, homevideo

xHamster

Express Yourself: Crossdresser Kitty's Guide to Authenticity!

Categories: amateur, american, beauty, big cock, big tits, crossdressing, femboy, feminization, first time, hd

JizzBunker

Destroying my sissy pussy

Categories: anal, big ass, big clit, close up, creampie, dildo, hardcore, high heels, masturbation, pussy

xHamster

Sissy uncages and jerks tiny dick

Categories: amateur, american, cumshot, fetish, hd, ladyboy, masturbation, piercing, sissy, small tits

TrannyOne

pink shemale sissy ride huge bbc dildo on mirror sissygasm

Categories: anal, anal toying, anus, ass, big black cock, big cock, black, cum, dick, dildo

aShemaleTube

Little Kitten Femboi in Anal Training

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

xHamster

TS Masturbating and Cum

Categories: asian, beauty, cum, hd, jerking, korean, masturbation, sissy, solo, transsexual

xHamster

Sissy Whore

Categories: amateur, anal, anal toying, crossdressing, dildo, fishnet, hd, homevideo, lingerie, masturbation

xHamster

Cute Clit Sissygasm in Panties & Tights

Categories: amateur, clit, crossdressing, cum, cumshot, cute, dildo, hd, lingerie, masturbation

xHamster

Sexy Girl Stephanie James - the sizzler

Categories: amateur, anal, big ass, canadian, crossdressing, gay, hd, homevideo, outdoor, pornstar

xHamster

Tavern Wenches Make Do!

Categories: anal, dutch, fantasy, glasses, hd, masturbation, sissy, small tits, toys, tranny

KeekAss

Horny Tranny Masturbates Her Hard Shaft

Categories: amateur, anal, ass, beauty, cartoon, cute, dick, femboy, girlfriend, handjob

ShemaleZ

Nely Sissy Culona Big Balls Bitch Self Cum Tranny Shemale

Categories: amateur, balls, big ass, bitch, cum, hd, ladyboy, latina, lingerie, sissy

aShemaleTube

k3ira

Categories: amateur, asian, sissy

ShemaleMovie

Crossdresser in sexy high heels, trans woman rides dildo

Categories: amateur, anal, big cock, crossdressing, cum, cumshot, dildo, feet, high heels, italian

xHamster

Julia Cool wearing Pantyhose under Denim and walking around

Categories: amateur, ass, blonde, crossdressing, european, femboy, high heels, jeans, nylon, pantyhose

xHamster

SISSY LOVELASKA

Categories: domination, fetish, hd, oiled, sissy, solo, teen (18+), transsexual, ukrainian

KeekAss

Cute Slim Tranny Playing With Her Dick

Categories: amateur, anal, beauty, big cock, brunette, cute, dick, handjob, high heels, homevideo

XXXDan

Riley has a sweet sissy ass! Will you be able to make it?

Categories: amateur, anal, ass, bbw, big ass, big clit, crossdressing, gay, girlfriend, lingerie

KeekAss

Smoking love and juggling arse doggy-style

Categories: amateur, ass, cosplay, crossdressing, cute, dick, doggystyle, femboy, hd, ladyboy

aShemaleTube

Sissy Crossdresser locking up her clitty

Categories: amateur, buttplug, cage, corset, crossdressing, hd, high heels, homevideo, sissy, stockings

KeekAss

Kimber's BIG BLACK COCK Sissy Trainer

Categories: anal, big ass, big black cock, big cock, big tits, black, blowjob, compilation, ebony, hd

aShemaleTube

Bitch Training By Her Sports Coach. Hard Facefucking. Cum Shot. Vanessabitchx

Categories: amateur, beauty, big cock, bitch, blowjob, coach, compilation, crossdressing, cumshot, european

xHamster

Sissy Jerking off

Categories: amateur, bbw, black, cum, cute, ebony, edging, hd, jerking, lingerie

KeekAss

Sissy Tramp Michelle Late Evening Dinner and WEB display

Categories: amateur, bisexual, clothed sex, cum, cum swapping, dick, european, feminization, fetish, glamour

ShemaleMovie

10-inch massive strapon pounded deep into femboy's asshole

Categories: anal, ass, brutal, dildo, fisting, hardcore, homevideo, huge dildo, pantyhose, sissy

JizzBunker

Sissy maid rides cock

Categories: amateur, anal, big cock, dick, german, lingerie, maid, masturbation, riding, sissy

XXXDan

Sissy Ass to Mouth Deep Throat Fuck Machine Sloppy

Categories: amateur, anal, ass to mouth, big ass, blowjob, crossdressing, deep throat, dildo, fetish, gagging

xHamster

Sissy Alexas makes ass pussy stretching exercises in chastity 1 of 2

Categories: amateur, anal, anal toying, ass, big tits, bisexual, blonde, fetish, fucking machine, gaping hole