Sissy Shemale Videos » 44

KeekAss

She-Male COUGAR Cracks Love Glove With Her Gigantic Man Rod & Pearly Jizm

Categories: amateur, big cock, blonde, condom, cougar, crossdressing, cum, cumshot, fetish, handjob

xHamster

TS Camelia dancing and teasing

Categories: amateur, ass, beauty, big ass, dancing, escort, french, hd, homevideo, lingerie

Pornstars: Camelia

aShemaleTube

slutty CATWOMAN deepthroat JOKER's giant cock

Categories: amateur, barebacking, big cock, blowjob, cartoon, cosplay, crossdressing, cum in mouth, deep throat, dick

xHamster

Bnwo - Your Whiteboy Future

Categories: 3d, anal, barebacking, big black cock, big cock, bondage, british, cuckold, domination, femboy

xHamster

Crossdresser in lingerie with toy

Categories: amateur, beauty, big cock, crossdressing, cum, cumshot, dildo, hd, lingerie, pantyhose

ShemaleMovie

Goth cum, onanism

Categories: anal, british, cum, cumshot, european, fishnet, goth, jerking, jizz, masturbation

KeekAss

I’m gonna make you the superslut tonight, whore.

Categories: big ass, big cock, compilation, crossdressing, cum, dick, domination, femboy, femdom, handjob

aShemaleTube

Good anal pounding

Categories: amateur, anal, crossdressing, cumshot, dress, hd, homevideo, lingerie, masturbation, mature

xHamster

Swimming, splashing and posing naked in the sea...

Categories: amateur, beach, beauty, blonde, european, hd, milf, nude, outdoor, posing

KeekAss

Sissy Ditzy Dirty Dancing with buttfuck cork

Categories: amateur, anal, ass, assfucking, bimbo, buttplug, crossdressing, dancing, dirty, fetish

TrannyOne

Paulina's Summer of 69 (Anal)

Categories: 69, anal, anus, ass, big cock, booty, compilation, crossdressing, cum, dick

aShemaleTube

The Tiniest Dick - Sissy

Categories: anal, big ass, dick, dildo, fucking machine, masturbation, mature, pussy, sissy, slut

aShemaleTube

adorable slim sissy strokes her massive dick

Categories: adorable, big cock, hd, sissy, slim, webcam

xHamster

Nasty Hatsune Miku🤍Vocaloid: Miku, which toy is the best? Skin-colored, maybe?

Categories: amateur, anal, asian, beauty, big ass, big cock, crossdressing, femboy, hd, japanese

aShemaleTube

MY LOVE 35

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

xHamster

Lara Sukkuba Episode 57 - Chatting & Edging - Huge Cock Shemale in Nylon Pantyhose Encasement Feet Fetish with Buttplug

Categories: amateur, beauty, big cock, buttplug, crossdressing, dick, edging, feet, fetish, german

aShemaleTube

Dizzy is bound and gagged in front of the mirror

Categories: bondage, bound, chained, crossdressing, gagging, hd, lingerie, mirror, sissy, stockings

XXXDan

Sissy ashtray

Categories: amateur, bdsm, lingerie, sissy, slut, solo, swiss

aShemaleTube

Sexy slim transgirl jerks off her big wet cock on webcam

Categories: amateur, big cock, dick, homevideo, jerking, latina, masturbation, pretty, sissy, slim

KeekAss

Alice Latexy adoring a faux-cock while on her knees in the douche

Categories: amateur, blowjob, crossdressing, dick, dildo, doll, fetish, hd, homevideo, knees

aShemaleTube

Pantyluvn sissy jerking in her bikini

Categories: amateur, bikini, chubby, crossdressing, cumshot, hd, homevideo, jerking, masturbation, mature

aShemaleTube

trans cum outdoors

Categories: cum, outdoor, sissy, solo, teen (18+), transsexual

ShemaleMovie

Trans goddess Jaymie Jameson takes it deep and gets filled by BBC

Categories: american, anal, babe, barebacking, beauty, big black cock, big cock, black, blowjob, creampie

xHamster

you're making me more and more bitch

Categories: bbw, bitch, dildo, french, hd, high heels, ladyboy, lingerie, sissy, solo

xHamster

Secretdreamsfuta Hard Anal Sex Delicious Tasty Big Ass Swallowing a Huge Monster Cock in Her Tight Ass Thirsty for Cum Rough Sex

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

xHamster

Sissymindy Cosplay chastity cage Foxy Forest walk

Categories: amateur, big ass, cage, cosplay, crossdressing, femboy, feminization, fetish, forest, hd

XXXDan

Rubber Sissy Slave

Categories: bdsm, rubber, sissy, slave

xHamster

Blonde Elf Smoking While Dance

Categories: amateur, asian, beauty, blonde, cute, hd, homevideo, joi, ladyboy, lingerie

KeekAss

Pretty sissy sixty nines Daddys face and takes his pink cigar wet

Categories: 69, amateur, anal, blowjob, cigarette, crossdressing, daddies, interracial, lingerie, pretty

aShemaleTube

Its Fucking Awesome - PMV by HoloPMV

Categories: amateur, anal, asian, big cock, cum, dancing, femboy, hd, sissy, small cock

aShemaleTube

Blonde girl with small dick in red lingerie

Categories: amateur, blonde, crossdressing, femboy, gorgeous, hd, lingerie, masturbation, pretty, sissy

aShemaleTube

sissy fucked by huge machine

Categories: amateur, anal, huge dildo, sissy, solo

xHamster

Sexy Blonde Sissy Puts Redhead Trans Woman in Bondage

Categories: amateur, american, bdsm, beauty, blonde, bondage, crossdressing, domination, feminization, hd

TrannyOne

A cute ladyboy from China publicly enjoys masturbation right in the park.

Categories: chinese, crossdressing, cum, cute, ladyboy, masturbation, outdoor, public, sissy

XXXDan

Dominatrix fucks a sexy sissy in chastity

Categories: amateur, anal, bdsm, bondage, crossdressing, dominatrix, fetish, hardcore, lingerie, sissy

KeekAss

Jism to Mummy hotty!

Categories: amateur, big cock, crossdressing, cum, cumshot, dick, feet, femboy, fetish, handjob

KeekAss

Dizzy In Urine Predominance!

Categories: amateur, bdsm, bondage, bound, crossdressing, domination, fetish, gagging, hd, mature

KeekAss

MY SISSY PUMMELS MY VULVA AND BUM ON THE TABLE ENTIRELY BARE AND JIZZ ON MY VAGINA

Categories: amateur, anal, blonde, crossdressing, cum, cumshot, cunt, hd, jizz, lesbian

aShemaleTube

Sissy workout PMV

Categories: compilation, crossdressing, hd, music, pov, sissy, solo, workout

ShemaleMovie

Sissy pantyhose, latex sissy

Categories: boots, crossdressing, cum, high heels, jizz, latex, lingerie, nylon, outdoor, pantyhose

xHamster

Nude Vintage Nylon Bra From Srs Catalog

Categories: bra, hd, lingerie, mature, nude, nylon, sissy, solo, vintage

aShemaleTube

Sexy bitch cum for you

Categories: bitch, blonde, boots, crossdressing, cum, cumshot, hd, homevideo, lingerie, masturbation

JizzBunker

Sissy drowned in fake sperm

Categories: amateur, british, facial, hardcore, sissy, solo, sperm

xHamster

Sissy Trainnig at Home

Categories: amateur, anal, big clit, big tits, boy, clit, domination, fetish, hd, homevideo

aShemaleTube

crossofia sfina anal

Categories: amateur, anal, big ass, crossdressing, fetish, ladyboy, lingerie, mature, pantyhose, sissy

xHamster

Kinky Alice wanking big cock and cum on beautiful feet

Categories: balls, beauty, big cock, cum, dick, feet, fetish, hd, kinky, ladyboy

aShemaleTube

BDSM style double dildo anal fuck

Categories: anal, asian, bdsm, chinese, cumshot, dildo, femboy, fetish, hd, ladyboy

xHamster

Sissy anal table joi

Categories: amateur, anal, anal toying, crossdressing, cum, dildo, feminization, fetish, hd, joi

aShemaleTube

POV Blowjob, Anal Dildo in Boots, Dirty Talk and Huge Facial

Categories: anal, anal toying, asian, big ass, blowjob, boots, crossdressing, cum in mouth, cumshot, dirty talk

Pornstars: Viper

xHamster

Sissy-Kuroko fan art costume Anal Dildo

Categories: amateur, anal, anal toying, costume, crossdressing, dildo, femboy, hd, huge dildo, japanese

JizzBunker

Sissy Lara White Big dildo Anal Masturbation Self fuck Big cumshot Big ass Crossdresser Shemale Tranny Tranny

Categories: amateur, anal, beauty, big ass, compilation, crossdressing, cumshot, deep throat, dildo, hardcore

KeekAss

The greatest trunk rating on PH with monstrous jizz shot

Categories: amateur, big cock, crossdressing, cum, cumshot, dick, feet, femboy, handjob, hardcore

Pornstars: Viper

KeekAss

Taylor Nicole: She Never Let Me Have Joy

Categories: anal, blowjob, creampie, funny, futanari, goth, hd, indian, lesbian, masturbation

KeekAss

Adorable sissy Sonia plays with her playthings

Categories: adorable, amateur, anal, anal toying, blonde, blowjob, buttplug, crossdressing, cute, hd

TrannyOne

BWC Daddy Cums Back to Breed Crossdresser's Wet Ass Bussy

Categories: amateur, american, anal, anus, ass, big cock, crossdressing, cum, daddies, dick

aShemaleTube

Riding and leaking 1

Categories: anal, dick, dildo, femboy, hd, lingerie, pov, riding, sissy, small cock

aShemaleTube

CdTina gagging on guest 1

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

KeekAss

Businessman made into a Sissy Tart

Categories: amateur, crossdressing, femboy, femdom, feminization, fetish, hd, joi, mistress, pov

aShemaleTube

you will love this sissy buttplug anal video

Categories: amateur, anal, big ass, big cock, blonde, buttplug, crossdressing, hd, lingerie, masturbation

xHamster

Sissy training from Katy Koroleva

Categories: amateur, anal, beauty, big cock, blowjob, compilation, crossdressing, cum, cumshot, femboy

XXXDan

DOUBLE ANAL, Vibrating Buttplug, Sexy Pink Dildo! Sissy Ts

Categories: amateur, anal, big ass, buttplug, dildo, double penetration, hardcore, mature, pov, sissy

xHamster

Leather BDSM tease

Categories: bdsm, bondage, british, crossdressing, dominatrix, fetish, hd, leather, leggings, mistress

aShemaleTube

AMATEUR BODYBUILDER vs Faggyboi

Categories: amateur, anal, big black cock, blowjob, bodybuilder, crossdressing, ebony, femboy, hd, sissy

KeekAss

I liked that good-sized Plaything so much i had to come

Categories: amateur, anal, anal toying, crossdressing, cum, cumshot, hd, huge dildo, masturbation, sissy

xHamster

Lucia's Chocolate Cake Video 2

Categories: ass, big cock, big tits, blonde, british, chocolate, cum, cumshot, dirty, fat

xHamster

I ripped my asshole!!

Categories: amateur, anal, anal toying, ass, beauty, crossdressing, cum, dildo, greek, hd

KeekAss

Femboy costume play self facial cumshot mega-bitch urinating

Categories: big cock, bitch, boy, cosplay, costume, cumshot, facial, femboy, fetish, hd

ShemaleMovie

Chastity cage, sissy femboy

Categories: amateur, beauty, big black cock, cage, cuckold, dildo, femboy, homevideo, sissy, toys

ShemaleMovie

Sissy crossdresser in anal play with sex toy

Categories: anal, anal toying, crossdressing, dildo, fishnet, gaping hole, masturbation, sissy, toys

XXXDan

Prissie Sissy Cock Punishment

Categories: bdsm, big cock, bondage, dick, german, hardcore, latex, mature, punishment, sissy

XXXDan

Part 2 Sexy Mexican Japanese stud fucks my pussy Candy Ass Sissy

Categories: amateur, anal, asian, bbw, big ass, blonde, crossdressing, fishnet, gay, hardcore

Pornstars: Candy Ass

xHamster

Sissy gaping ass and self fisting. #2

Categories: anal, anal fisting, anal toying, asian, ass, fisting, gaping hole, hd, masturbation, milf

KeekAss

Cute Redhead Shemale Jacking Off In Front Of Webcam

Categories: amateur, beauty, crossdressing, cute, hd, high heels, homevideo, jerking, ladyboy, lingerie

aShemaleTube

Sissy Snow Bunny Sucks daddys Fat Black Dick

Categories: big cock, black, blowjob, bunny, crossdressing, daddies, dick, fat, fetish, hd

TrannyOne

Sissy receive In The Hood For A yummy 3some

Categories: 3some, gangbang, ghetto, orgy, sissy

aShemaleTube

Sissy Joanna Burke 'bateing for all eyes

Categories: amateur, crossdressing, femboy, homevideo, masturbation, sissy

Txxx

Holiday Sissy Cumbucket

Categories: asian, holiday, pornstar, sissy

Pornstars: Venus Lux

JizzBunker

Punished sissy Kenzie Star fucks her pussy

Categories: amateur, anal, dildo, punishment, pussy, sissy, solo, teen (18+)

KeekAss

Pretty She-Creature In Stomach Dancer Sundress Homemade Steamy Platinum-Blonde Model

Categories: amateur, asian, beauty, big ass, blonde, brunette, crossdressing, dancing, femboy, fetish

KeekAss

Otokonokob Plaything Fuckview - Vanniall

Categories: amateur, anal toying, beauty, big cock, black, cum, dick, dildo, doll, facial

TrannyOne

Hottest Mistress Norma Dominating Her trans Slave on Webcam 8

Categories: bdsm, domination, feet, femdom, fetish, footjob, hd, latex, lingerie, mistress

aShemaleTube

yui_kitano Summer Anal masturbation 2025

Categories: amateur, anal, anal toying, bbw, hardcore, japanese, masturbation, sissy, solo

xHamster

Slut Tranny MILF Fucking Her Ass

Categories: anal, ass, big ass, dildo, hd, masturbation, mature, milf, pussy, sissy

xHamster

Sissy and Obedient and Sucks It with Pleasure 2

Categories: amateur, barebacking, bbw, big cock, black, blowjob, crossdressing, handjob, hd, interracial

xHamster

Chubby Sissy Cum on Chocolate

Categories: amateur, bbw, big ass, black, chocolate, chubby, crossdressing, cum, cumshot, ebony

JizzBunker

2 sissy sluts gangbang for Halloween

Categories: anal, gangbang, halloween, sissy, slut

JizzBunker

Kellystar518 - The Sultans New Sissy

Categories: arab, bdsm, big ass, big cock, bondage, cosplay, crossdressing, fetish, hardcore, high heels

KeekAss

Yankee Cutie Crimson B-ten + Tearing Up Machines + Vacuum Pump = Good Pound trio

Categories: amateur, anal, anal toying, ass, assfucking, crossdressing, cumshot, cute, femboy, fucking machine

aShemaleTube

Dildo deepthroat traning

Categories: amateur, blowjob, crossdressing, deep throat, dildo, homevideo, hungarian, lingerie, sissy, small tits

xHamster

Magic tricks...

Categories: amateur, anal, anal toying, crossdressing, dildo, femboy, greek, hd, lingerie, riding

aShemaleTube

Nasty Lara tribute

Categories: ass, boots, cum swallowing, cumshot, dildo, high heels, masturbation, model, nun, sissy

aShemaleTube

Orgasmic Queen Lily self-facial cum show 💦

Categories: anal, big ass, big cock, big tits, cum, cumshot, facial, femboy, hd, masturbation

XXXDan

Sissy Bitch Trainer gifs 3

Categories: big cock, bitch, hardcore, milf, sissy

xHamster

Cute sissy gives blowjob and gets fucked by daddy

Categories: amateur, anal, beauty, big cock, blowjob, crossdressing, cute, daddies, femboy, feminization

KeekAss

Red-Hot sissygasm,ass fucking ejaculation

Categories: amateur, anal, assfucking, big ass, cumshot, femboy, hd, ladyboy, masturbation, orgasm

KeekAss

Sissy Sadee Gives Super-Naughty Wifey Surprise Ass-Fuck Lovemaking Packing Her Bootie With Jizz

Categories: amateur, anal, assfucking, bbw, big ass, big cock, couple, creampie, crossdressing, cum

TrannyOne

She's a Squirter

Categories: anal, anal toying, anus, asian, ass, compilation, dildo, female ejaculation, female orgasm, hd

aShemaleTube

I am Elena Andreou, in erotic moments alone, I cum and fuck my pussy with orgasm

Categories: anal, anal toying, close up, compilation, crossdressing, cum, cumshot, dick, dirty talk, erotic

ShemaleMovie

Lauryl Canyon tears it up with the fucking machine in sexy stockings and high heels

Categories: anal, crossdressing, dildo, european, fucking machine, high heels, huge dildo, ladyboy, masturbation, orgasm

Pornstars: Lauryl Canyon

aShemaleTube

gorgeous sissy rides sex machine

Categories: anal, crossdressing, femboy, gorgeous, hd, homevideo, ladyboy, sissy, small cock, solo

xHamster

Amyts Suck Erika Oak

Categories: amateur, asian, blonde, blowjob, handjob, hd, korean, ladyboy, sissy, solo

KeekAss

A doll who can't stand her dad's stringent discipline and finishes up blubbering and urinating herself

Categories: amateur, anal, asian, crossdressing, cumshot, dildo, doll, femboy, hd, ladyboy

xHamster

Cute trans slut in miniskirt and heels walks naked in public very hot

Categories: american, barebacking, big ass, crossdressing, cum, cute, hd, high heels, ladyboy, masturbation

XXXDan

Sissy crossdresser XL gets fucked in anal machine by big cock Tiffany Ciskiss

Categories: amateur, anal, big ass, big cock, crossdressing, dildo, european, fetish, fishnet, fisting

KeekAss

Your tgirl gf demonstrates you how to have fun with a shaft pump

Categories: amateur, big ass, big cock, brunette, canadian, crossdressing, cute, dick, feet, femboy

xHamster

the sissy walks in a public park

Categories: amateur, big tits, crossdressing, french, ladyboy, lingerie, mature, outdoor, park, public

KeekAss

Juicy Jizz climax with urethra injection have fun

Categories: blonde, crossdressing, cum, cumshot, fetish, funny, handjob, hd, insertion, jizz

KeekAss

Sissy Maid Self Restrain Bondage Armbinder, Anklecuffs in Balletboots

Categories: amateur, bdsm, bondage, crossdressing, hd, homevideo, latex, maid, sissy, stockings

aShemaleTube

castrated_julie

Categories: amateur, american, anal, anal toying, big tits, blonde, blowjob, mature, piercing, sissy

xHamster

Sissification Transformation by Roommate

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

ShemaleMovie

Crossdressing sissy in high heels plays teasingly and enjoys solo play

Categories: anal, ass, assfingering, crossdressing, dildo, femboy, high heels, sissy, solo, stockings

xHamster

Liza Femb Enjoys Anal Masturbation Until Sperm Starts Leaking Out of Her Ass

Categories: amateur, anal, anal toying, ass, big ass, crossdressing, dildo, european, femboy, hd

xHamster

ZiziBrindacier

Categories: amateur, anal, beauty, canadian, dildo, fetish, hd, masturbation, milf, pretty

XXXDan

Sissy in blue dress fucked

Categories: anal, blowjob, couple, creampie, dress, gay, hardcore, sissy, teen (18+)

aShemaleTube

Hot Sissy Futa Salivate While Sucking Her Dildo

Categories: blowjob, dildo, futanari, hd, masturbation, sissy, solo, sucking, webcam

KeekAss

Attractive Cum Shot

Categories: amateur, beauty, big ass, crossdressing, cum, cumshot, german, homevideo, jerking, lingerie

aShemaleTube

Encounter with the Sissy Demon (Crossdresser)

Categories: amateur, asian, crossdressing, dirty talk, fetish, halloween, hd, homevideo, lingerie, mask

aShemaleTube

AndyLynn

Categories: anal, barebacking, big cock, big tits, blowjob, cumshot, femboy, hd, homevideo, ladyboy

aShemaleTube

Sissy crossdresser, sucking big cock while he films

Categories: amateur, big ass, big cock, bimbo, blonde, blowjob, crossdressing, femboy, hd, homevideo

xHamster

Having fun

Categories: funny, hd, italian, ladyboy, masturbation, sissy, skinny