Sissy Shemale Videos » 31

xHamster

My dream has always been to ride your hard cock daddy

Categories: amateur, anal, big ass, colombian, creampie, crossdressing, daddies, dick, fantasy, femboy

xHamster

Sitting on my chair in my pink top stockings and butterfly chain with my vibrating cock ring squirting cum

Categories: amateur, australian, big ass, big cock, crossdressing, cum, cumshot, dick, femboy, hd

xHamster

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

Categories: amateur, bdsm, beauty, blowjob, croatian, crossdressing, fetish, hardcore, hd, homevideo

xHamster

Leatransteen in a Pink Satin Skirt Cum in Own Mouth

Categories: amateur, cum, cum in mouth, german, hd, lingerie, masturbation, own cum, satin, sissy

KeekAss

Wide Open then cuming from rectal only using fuck stick on stool

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

KeekAss

Popshot in Stretch Pants

Categories: amateur, anal, compilation, crossdressing, cum, cumshot, dick, fetish, high heels, joi

KeekAss

TRANSSEXUAL Sissy Doofy Marionette Lady Harsh Restrain Bondage

Categories: bdsm, big tits, bimbo, blonde, bondage, fetish, hd, kinky, lingerie, masturbation

Pornstars: Enza

xHamster

Beautiful shemale anal orgasms small cock beautiful face and big ass in thong (trans ejaculation)

Categories: amateur, anal, ass, beauty, big ass, booty, colombian, feminization, hd, ladyboy

xHamster

It's a Transwoman Thing

Categories: amateur, crossdressing, hd, lingerie, mature, redhead, sissy, smoking, solo

aShemaleTube

Multi orgasmic queen Lily 💦💦💦

Categories: big cock, big tits, cumshot, femboy, hd, masturbation, orgasm, queen, sissy, toys

JizzBunker

ALLISON LACE BAREBACK SISSY SLUT

Categories: barebacking, gay, lace, sissy, slut

aShemaleTube

Mikaela Lilyskin dirty talk in Swedish, swallows piss and cum

Categories: anal, chubby, cum, cum swallowing, cumshot, dirty talk, hd, long hair, masturbation, mature

KeekAss

Tranny Wanking Off Her Long Dick

Categories: amateur, american, beauty, cute, dick, dildo, hd, homevideo, kissing, ladyboy

xHamster

Fucking My Ass with a Fuckmachine - Sissy, Slut, Big Ass, Small Dick

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

KeekAss

Gundam Miorine Cosplayer Gives Hand Job And Gets Plumbed, Asian Anime Costume Play Part.six

Categories: amateur, anal, anime, asian, blowjob, chinese, cosplay, costume, crossdressing, femboy

aShemaleTube

COWBOY JAMIR Makes Long Trek to Fuck Faggyboi

Categories: big black cock, crossdressing, ebony, fake tits, femboy, gay, hd, lingerie, sissy

aShemaleTube

Wanking spanking and fucking my sissy till we both cum together 5th May 2025

Categories: anal, barebacking, cum, hd, masturbation, mature, sissy, spanking, transsexual, wanking

xHamster

Taboo Toy Delights Pixelated

Categories: amateur, anal, british, crossdressing, dick, dildo, feet, hd, masturbation, sissy

ShemaleMovie

Young sissy, young ladyboy

Categories: amateur, bdsm, beauty, crossdressing, domination, european, ladyboy, lingerie, sissy, slave

KeekAss

Shemale Cock Up Close

Categories: amateur, anal, asian, ass, beauty, big cock, crossdressing, cute, dick, femboy

aShemaleTube

Sissy Crossdresser Annette quick motel blowjob and facial

Categories: amateur, blowjob, crossdressing, cumshot, facial, hd, motel, sissy

xHamster

Sissy In Chastity and Panties

Categories: amateur, dildo, hd, high heels, homevideo, huge dildo, lingerie, masturbation, panties, sissy

KeekAss

Stunning Shemale In Stockings Masturbating On Cam

Categories: amateur, beauty, brunette, crossdressing, cute, dick, homevideo, masturbation, queen, sissy

KeekAss

Santa Bangs Super-Hot COUGAR

Categories: amateur, anal, bbw, beauty, big ass, big black cock, big cock, cougar, crossdressing, hd

AlphaPorno

Two redheads, Rachael Belle and Roxxie Moth, in hot lesbian action

Categories: anal, blowjob, bra, cowgirl, cumshot, doggystyle, facial, fake tits, hd, lesbian

TrannyOne

sissy wants misstress dick

Categories: big ass, big cock, big tits, blowjob, cumshot, dick, gay, hd, homevideo, sissy

xHamster

horny Latex bessy ass walk with wellingtons .fetish art by linda gumlin

Categories: anal, anal toying, ass, big ass, compilation, crossdressing, dildo, fetish, gay, german

xHamster

Sissy college slut is fucked by professor

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

aShemaleTube

Sissy crossdresser in mini skirt and glossy pantyhose gives you a lot of cum!

Categories: big cock, crossdressing, cum, cumshot, fetish, hd, homevideo, lingerie, masturbation, miniskirt

JizzBunker

Bimbo life of a sissy smoker

Categories: amateur, big cock, bimbo, black, blowjob, crossdressing, dutch, hardcore, latex, latina

xHamster

Connie hot white

Categories: big ass, brunette, feminization, ladyboy, latina, masturbation, mature, pantyhose, pretty, sissy

aShemaleTube

Cumswapping_Older_Cross_Dressers

Categories: blonde, blowjob, brunette, crossdressing, cum in mouth, cum swapping, cumshot, hd, homevideo, lingerie

xHamster

a sissy slut a 47 year old mature woman fucks like two female dogs in heat

Categories: amateur, anal, anal toying, couple, crossdressing, cum, dildo, femboy, french, hd

aShemaleTube

COCK SLAP MY FACE IN SLOW MO

Categories: big cock, big tits, dick, femboy, lingerie, pantyhose, pov, sissy, slap, solo

xHamster

Please Don't Tell Countess!

Categories: bdsm, bondage, domination, fetish, gagging, hardcore, hd, pornstar, punishment, sissy

Pornstars: Countess

aShemaleTube

Japanese sissy public toilet adventure 1(with subtitles)

Categories: amateur, asian, crossdressing, japanese, masturbation, model, public, sissy, toilet, transsexual

xHamster

Trans Girl Fucks Her Ass With A Huge Cucumber - Maddy Diamond

Categories: amateur, anal, anal toying, ass, bitch, blonde, cucumber, dildo, feminization, fetish

aShemaleTube

Asian Sissy Femboy

Categories: asian, blonde, chinese, compilation, cumshot, femboy, homevideo, lingerie, pantyhose, sissy

KeekAss

Adorable crossdresser in rosy tears up silicone beaver

Categories: adorable, amateur, beaver, big ass, crossdressing, cute, dick, fake tits, hd, homevideo

aShemaleTube

TS 422

Categories: amateur, anal, femboy, hd, homevideo, sissy, teen (18+), transsexual

ShemaleMovie

Stunning Colombian shemale Missangell_ gets it on with Mrnastyxavier

Categories: amateur, anal, babe, barebacking, beauty, big black cock, big cock, black, colombian, creampie

xHamster

Deep Inside Ms. Grinch's Tight grooty' Hole

Categories: amateur, american, ass, big ass, big cock, cum, cumshot, doll, fleshlight, hd

aShemaleTube

Caught reading naughty magazines by Mistress

Categories: bdsm, bondage, caught, crossdressing, hd, lingerie, mistress, naughty, sissy, stockings

xHamster

Crossdresser Emika shows off sexy legs in high heels and strokes cock

Categories: amateur, big cock, canadian, crossdressing, dick, feminization, hd, high heels, legs, lingerie

aShemaleTube

Hot Australian sissy plays with her Hole

Categories: australian, sissy

xHamster

Cute Femboy Playing with Her Sexy Feet

Categories: amateur, arab, cute, feet, femboy, fetish, hd, high heels, lingerie, masturbation

xHamster

sissy masturbates cock in dressing room

Categories: amateur, big tits, crossdressing, dick, dress, dressing room, french, hd, ladyboy, lingerie

aShemaleTube

Sissy Vein shake her clitty while get fucked [retro]

Categories: amateur, anal, asian, chinese, crossdressing, femboy, futanari, hd, homevideo, lingerie

aShemaleTube

I got bred by a Black Alpha

Categories: anal, big ass, big black cock, big cock, black, cage, femboy, hd, interracial, sissy

aShemaleTube

Sissy Slut Margo

Categories: boots, crossdressing, hd, sissy, slut, solo

xHamster

Huge Cum Out of My Sissy Ass After Fucking My Big Ass with Big Toys

Categories: anal, ass, big ass, cum, cumshot, dildo, fucking machine, hd, masturbation, mature

aShemaleTube

Lostwind Comp1

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

xHamster

Fashion Hacks: Tips and Tricks for Style Success

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

xHamster

Merry Xmas from sissy Emma Huntcock

Categories: amateur, big tits, british, crossdressing, dirty talk, hd, high heels, mature, sissy, slut

aShemaleTube

Sloppy Jessica SelfSuck

Categories: big cock, blonde, cumshot, femboy, homevideo, lingerie, masturbation, pantyhose, sissy, sloppy

KeekAss

Chinese maid frolicking solo part2

Categories: amateur, anal, asian, assfucking, big ass, brunette, cage, chinese, costume, crossdressing

aShemaleTube

Arabic TGIRL Mikah Hotel Blowjob

Categories: amateur, arab, blowjob, crossdressing, fetish, hd, hotel, sissy, slut, tgirl

aShemaleTube

Sissy cojida por un empleado del hotel

Categories: anal, barebacking, blonde, crossdressing, hd, hotel, lingerie, sissy, small cock

aShemaleTube

My Video 369: Desi Punjabi Boy Cums On Mona Khan's Oily Asscheeks

Categories: amateur, asian, boy, cum, cumshot, desi, gay, hd, homevideo, interracial

aShemaleTube

Xmas (Old Remastered)

Categories: amateur, blonde, crossdressing, hd, homevideo, latina, lingerie, old, santa, sissy

xHamster

Jessica Bloom Plapping - Ball Busting Chastity Orgasm Sissy Cumslut

Categories: amateur, ball busting, blonde, british, crossdressing, cum, cumshot, fetish, hd, orgasm

xHamster

Outdoor Fisting. Lola Spais

Categories: amateur, anal, anal fisting, couple, fisting, hd, masturbation, outdoor, public, sissy

aShemaleTube

Sissy fucking herself Ryley

Categories: dildo, hd, huge cock, lingerie, sissy, skinny, skirt, solo

KeekAss

Insatiable Superslut Wide Open Bootie After Cucumber Pummel

Categories: amateur, anal, ass, beauty, cucumber, cum, cumshot, masturbation, sissy, solo

xHamster

Petra's porno marathon part 1-3

Categories: amateur, anal, barebacking, big cock, blowjob, crossdressing, cute, dildo, dutch, femboy

aShemaleTube

Wuliuzzz Comp3

Categories: anal, asian, chinese, compilation, femboy, hd, homevideo, sissy, small cock, small tits

xHamster

Thick 33 cm dildo for my phat sissy ass

Categories: anal, anal toying, ass, bbw, dildo, fetish, hd, latina, masturbation, mature

KeekAss

Amazing Amateur Shemale Video

Categories: amateur, amazing, anal, beauty, crossdressing, cute, dick, femboy, homevideo, japanese

xHamster

Fucking My Ass with a BBC Dildo. Tranny MILF, Sissy Slut

Categories: amateur, anal, ass, big ass, big black cock, dildo, fucking machine, hd, mature, milf

ShemaleZ

Sissy Dancing is back! - Watch the Tempo

Categories: amateur, big ass, crossdressing, dancing, sissy, solo

TrannyOne

Faggot cocksucker giving sloppy head to straight alpha, earning a fat nut in return

Categories: amateur, american, bdsm, big cock, blowjob, couple, creampie, crossdressing, cum, cum in mouth

KeekAss

Crossdressing Maid Needs Raw Bareback Dick

Categories: anal, barebacking, crossdressing, dick, femboy, hardcore, hd, maid, sissy

aShemaleTube

leather coat mistress dominate her sissy

Categories: amateur, anal, asian, big cock, blowjob, domination, hd, ladyboy, leather, mistress

xHamster

Birthday present Solo

Categories: amateur, american, beauty, big cock, birthday, blonde, cum, cumshot, hd, masturbation

aShemaleTube

Assfucked in Armbinders

Categories: anal, assfucking, bondage, cage, femdom, hd, huge dildo, model, pegging, sissy

aShemaleTube

Muscle TS Daphne Halloween cosplay anal show🍑

Categories: anal, big ass, big cock, cosplay, femboy, halloween, hd, latina, masturbation, muscled

aShemaleTube

Milena's streaptease

Categories: amateur, hd, high heels, homevideo, sissy, small cock, small tits

XXXDan

Sissy enjoys her dildo

Categories: amateur, anal, big ass, big cock, black, crossdressing, dildo, hardcore, hungarian, lingerie

KeekAss

Damsel On Tranny Assfuck Pegging & Dt Jessica Bloom And Polieana

Categories: amateur, anal, ass, assfucking, beauty, big cock, blowjob, cum, cumshot, dick

aShemaleTube

Queen of the Sissy University

Categories: amateur, anal, barebacking, blonde, blowjob, cumshot, handjob, hardcore, hd, lingerie

IcePorn

Horny sissy trap stroking her big cock

Categories: big ass, big cock, big tits, hd, masturbation, sissy, solo, stroking

aShemaleTube

I wish they were my soccer team

Categories: amateur, big ass, big cock, ebony, femboy, ladyboy, latina, lingerie, masturbation, sissy

aShemaleTube

CdTina sucking 1

Categories: amateur, big cock, blonde, blowjob, crossdressing, fetish, hd, long nails, mature, sissy

aShemaleTube

Sissy Bride Alexa Degrades Herself

Categories: bride, sissy

TrannyOne

We Both Got Caught (pmv)

Categories: caught, compilation, crossdressing, cumshot, domination, homevideo, sissy, small cock, stockings

xHamster

Hardcore Fisting and Squirt

Categories: anal, dildo, domination, extreme, fisting, fucking machine, gaping hole, hardcore, hd, high heels

KeekAss

Enormous caboose round sissy tart

Categories: amateur, ass, big ass, blonde, chubby, crossdressing, fat, femboy, game, hd

KeekAss

First-Timer crossdresser jism with king wood faux-cock

Categories: amateur, anal, anal toying, blonde, crossdressing, cum, cumshot, dick, dildo, femboy

aShemaleTube

Transvestite Tingxuan takes a bath in the bathtub wearing clothes

Categories: bathroom, clothed sex, hd, ladyboy, masturbation, sissy, skirt, transvestite

ShemaleMovie

Nurse costumed crossdresser Apersonwholikesboobs milks a hard cock in style

Categories: amateur, british, costume, crossdressing, dick, lingerie, masturbation, nurse, sissy, stockings

xHamster

Big ass blonde bitch

Categories: amateur, anal, asslick, bbw, big ass, big black cock, bitch, blonde, cum, hd

xHamster

Crossdresser penelopene fuck hardcore XXL dildo

Categories: anal, bdsm, crossdressing, dildo, hardcore, hd, ladyboy, sissy, slave, spanish

aShemaleTube

chastity cage cum on fishnet

Categories: cage, cum, cumshot, fishnet, hd, homevideo, lingerie, pantyhose, sissy, toys

JizzBunker

Sissy Dildo cum with swimsuit

Categories: bikini, cum, dildo, sissy, swimsuit

xHamster

Accessorize Like a Pro: Elevating Your Outfits

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

xHamster

Hanging klitt

Categories: amateur, bdsm, big clit, bondage, danish, dick, european, hd, ladyboy, latex

KeekAss

Transgender Princess Riley's Sugary-Sweet Donk in Hooter-Sling and Undies Taunting!

Categories: amateur, ass, beauty, big ass, blonde, bra, crossdressing, cute, dirty talk, fat

aShemaleTube

Mature Sissy Maid

Categories: anal, big cock, blowjob, brunette, gay, hd, maid, mature, sissy

ShemaleMovie

Joyful in nylons and covered in cum shots

Categories: amateur, babe, beauty, big cock, crossdressing, cum, cumshot, german, handjob, jizz

xHamster

my sissy pussy likes to eat eggplant

Categories: amateur, anal, ass, beauty, crossdressing, femboy, feminization, hd, homevideo, ladyboy

xHamster

Joselynne Cd In Sexy Stockings And Heels Show Ass And Sissy Pussy

Categories: amateur, ass, big ass, big cock, crossdressing, feminization, hd, high heels, ladyboy, mature

xHamster

Serge3dx Delicious Hot Asses Thirsty to Swallow Cum Sweet Pleasure Tasty Hot Ass Open

Categories: amateur, asian, ass, big ass, big cock, crossdressing, cum, cum swallowing, hd, huge cock

TrannyOne

Happy Christmas Sissy Slut

Categories: asian, cumshot, fishnet, hd, high heels, masturbation, public, sissy, slut, stockings

xHamster

Marzia slut fucks and sucks dildo

Categories: amateur, anal, crossdressing, cum, dildo, fetish, hardcore, hd, high heels, italian

xHamster

Hot Crossdresser in Female Body Suit Rubs Pussy with Dildo

Categories: amateur, american, anal, blowjob, boy, crossdressing, dildo, extreme, gay, hd

aShemaleTube

Huge bat in my ass followed with magic wand to cum

Categories: anal, ass, big ass, close up, cum, cumshot, hd, panties, sissy, solo

aShemaleTube

Alice Wonderland (enhanced)

Categories: amateur, blonde, crossdressing, hd, homevideo, latina, lingerie, sissy, stockings, uniform

aShemaleTube

teen femboy solo

Categories: amateur, dick, femboy, hd, homevideo, pov, sissy, small cock, solo, teen (18+)

KeekAss

Alt tgirl jacks for you

Categories: amateur, anal, anal toying, beads, cum, cumshot, deep throat, femboy, hd, huge dildo

xHamster

Sissyfication for Girls Night Out

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

JizzBunker

Sissification 32 Animation

Categories: animation, sissy

xHamster

Slutty stepmom Andreina

Categories: big tits, crossdressing, cute, feet, fetish, glasses, hd, italian, mature, mom

xHamster

Sissy Maid Testing Buttplugs and Outfits

Categories: amateur, anal, anal toying, hd, latex, maid, masturbation, sissy, solo

aShemaleTube

OPS you GAY !!! beautiful blonde trans cumshot

Categories: amateur, beauty, big ass, big cock, big tits, blonde, crossdressing, cumshot, domination, gay

KeekAss

Sissy Victim Abjection for Domme

Categories: amateur, anal, ass, booty, crossdressing, sissy, slut, stockings, torture, toys

xHamster

Ladyboy Sex in Pantyhose Ass Broken

Categories: amateur, ass, bbw, beauty, big ass, big cock, black, compilation, creampie, crossdressing

xHamster

How to clean the asshole? sissy handbook

Categories: anal, ass, asslick, bukkake, cleaner, cum in mouth, cumshot, double penetration, gaping hole, german

aShemaleTube

tall skinny shemale with pink shiny leggings and huge cock cumshot

Categories: amateur, big cock, cumshot, hd, homevideo, huge cock, leggings, masturbation, model, sissy

KeekAss

Tranny amateur fucks her emo girlfriend

Categories: amateur, beauty, big ass, bimbo, blowjob, emo, girlfriend, hd, homevideo, lesbian

xHamster

Stroking my cock well talking about you riding my cock

Categories: amateur, dick, fetish, hd, homevideo, ladyboy, masturbation, mature, pov, riding