Sissy Shemale Videos » 44

TrannyOne

Feminization 3 (Animation)

Categories: anal, animation, anime, anus, ass, bdsm, big cock, blowjob, dick, domination

aShemaleTube

My Christmas Special you been naughty this year

Categories: amateur, big cock, cumshot, hd, homevideo, latina, lingerie, naughty, pov, sissy

aShemaleTube

Lux

Categories: asian, big cock, big tits, blowjob, chinese, cumshot, femboy, hd, homevideo, interracial

Pornstars: Venus Lux

aShemaleTube

Bbc fucks Sissy Stacy doggy style

Categories: anal, big black cock, bimbo, crossdressing, doggystyle, hd, sissy, tranny

aShemaleTube

Slim trap with pink hair fucked hard with own cum lubrifiant

Categories: anal, ass, big cock, crossdressing, dildo, femboy, hardcore, hd, high heels, lingerie

KeekAss

Small Femboy Attempts To Twerk And Their Super-Cute Bootie Claps So Lovely

Categories: amateur, ass, bisexual, compilation, crossdressing, cute, dick, femboy, hd, ladyboy

TrannyOne

Sissy Charlotte gets flogged and Electro stim on her cock

Categories: amateur, bdsm, british, crossdressing, dick, domination, english, european, hd, homevideo

ShemaleMovie

POV: flexible femboy Liza Femb riding your dick hard

Categories: amateur, anal, ass, beauty, big ass, close up, crossdressing, cum, dick, dildo

aShemaleTube

playing

Categories: crossdressing, domination, hd, homevideo, lingerie, mature, sissy, small cock, stockings

aShemaleTube

High on Shemale Mushrooms 🍄

Categories: amateur, big ass, big cock, blowjob, compilation, cumshot, dick, femboy, fetish, hd

aShemaleTube

Sissy trap with big dildo

Categories: dildo, hd, high heels, lingerie, own cum, sissy, stockings

KeekAss

Sissy in innocence is railing a faux-cock and getting an heavy sissygasm while dressed in a lip gag

Categories: amateur, anal, assfucking, blonde, cage, crossdressing, cumshot, dick, dildo, fetish

KeekAss

Sissy Expect, the nasty whore & her fresh web cam

Categories: amateur, anal, buttplug, ladyboy, latina, lingerie, masturbation, mature, mexican, piercing

aShemaleTube

Wrecking her hot mexican ass

Categories: amateur, anal, ass, hd, homevideo, latina, mexican, sissy

ShemaleMovie

Playing with my small sissy dick while savoring all my cum

Categories: amateur, british, crossdressing, cum, cum in mouth, cumshot, dick, jizz, lingerie, masturbation

JizzBunker

Cum Like a Sissy Slut - Sissy Captions

Categories: anal, big ass, big cock, cum, cumshot, hardcore, masturbation, mature, sissy, slut

JizzBunker

Sissy slut rides in Chastity

Categories: amateur, anal, crossdressing, dildo, european, hardcore, hungarian, latex, lingerie, masturbation

aShemaleTube

SissySlut craves BBC

Categories: big black cock, crossdressing, femboy, fetish, hd, homevideo, joi, mature, model, pov

aShemaleTube

Trans girl sucks a dildo and masturbates

Categories: amateur, big ass, big cock, big tits, creampie, dildo, homevideo, masturbation, sissy, solo

aShemaleTube

Elise Banging Me Hard in My Big Beautiful Ass & Creampied Anal Deep

Categories: anal, asian, banging, beauty, big ass, big cock, creampie, domination, indian, ladyboy

ShemaleMovie

Chunky sissy Shenhunk gets festive in a Halloween outfit

Categories: anal, ass, bbw, big ass, chubby, chunky, crossdressing, dildo, ebony, fat

aShemaleTube

Orgasmic Queen Lily self-facial cum show 💦

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

aShemaleTube

Japanese crossdresser suck stranger dick in public toilet

Categories: asian, blowjob, crossdressing, dick, japanese, public, sissy, stranger, sucking, toilet

KeekAss

Rigid moaning shag - big culo white shemale CD gets a deep porking from fapped black mucle wolf

Categories: amateur, anal, ass, big ass, black, blonde, creampie, crossdressing, ebony, hd

Pornstars: Candy Ass

TrannyOne

Sharigurl Sissy Clit Cums Riding Dildo

Categories: amateur, clit, crossdressing, cum, cumshot, dick, dildo, hd, homevideo, lingerie

TrannyOne

Extreme Anal Young Shemale Gaped Anus and Big Dildo Party

Categories: american, anal, anal toying, anus, ass, big ass, big cock, booty, crossdressing, cum

aShemaleTube

Selffuck in the Forrest nearby Street

Categories: amateur, anal, crossdressing, hd, lingerie, outdoor, sissy, solo, stockings, street

ShemaleMovie

Admiring stepmom's big ass in sexy lingerie

Categories: anal, ass, bbw, big ass, blowjob, crossdressing, dildo, italian, lingerie, masturbation

ShemaleMovie

Tgirl Janelle Fennec enjoys anal play with a dildo until she reaches orgasm!

Categories: anal, ass, assfingering, babe, beauty, blonde, dildo, handjob, masturbation, monster cock

KeekAss

Adorable Tgirl Jerks Her Cock In Closeup

Categories: adorable, amateur, beauty, brunette, close up, dick, femboy, hd, homevideo, kissing

KeekAss

Tranny Gets Her Hole Fucked

Categories: amateur, anal, beauty, crossdressing, cute, homevideo, jerking, kitchen, lesbian, masturbation

KeekAss

My super-hot donk for you.spunk. Pin two

Categories: amateur, anal, ass, big ass, crossdressing, doggystyle, hd, joi, lingerie, pov

aShemaleTube

CD Friends Have Sex

Categories: amateur, anal, asian, chinese, crossdressing, friend, pantyhose, sissy

aShemaleTube

Chinese sissy Alicexiao nurse outfit

Categories: amateur, anal, asian, chinese, hd, nurse, sissy, stockings, toys

aShemaleTube

19yo skinny glasses tgirl gets machine fucking on webcam

Categories: amateur, anal, dildo, fucking machine, glasses, homevideo, masturbation, sissy, skinny, teen (18+)

aShemaleTube

Sissy Maid Dildo And Chastity

Categories: asian, crossdressing, dildo, lingerie, maid, sissy, toys, uniform

aShemaleTube

Sissy Rachel is desperate for cocks.

Categories: amateur, crossdressing, desperate, dick, homevideo, lingerie, masturbation, sissy, solo, stockings

TrannyOne

Hot Babe In Bikini Fucks Thick Girl With Tans Lines Creampie

Categories: anal, ass, babe, beauty, big tits, bikini, blowjob, booty, creampie, cum

KeekAss

CRIMSON SIGNAL PART 1 - CROSSDRESSING BY SISSY SHRUTEE

Categories: amateur, anal, asian, ass, big ass, big tits, crossdressing, handjob, hardcore, hd

aShemaleTube

FEMBOY SUCKS FEMBOY 11MIN

Categories: amateur, big cock, cumshot, femboy, fetish, pov, sissy, sucking

ShemaleMovie

Stunning shemale Crystal Phoenix with a pink asshole ready to heat things up

Categories: amateur, anal, ass, babe, beauty, big ass, blonde, crossdressing, dildo, femboy

aShemaleTube

Trans Doll Produces a Lot of Cum

Categories: blonde, cum, cumshot, doll, femboy, homevideo, lingerie, masturbation, sissy, small tits

aShemaleTube

Sexy whore playing

Categories: barebacking, blonde, cumshot, glasses, hd, homevideo, lingerie, masturbation, mature, sissy

KeekAss

Adorable femboy gets porked by thick faux-cock

Categories: adorable, amateur, anal, big ass, brunette, creampie, crossdressing, dick, dildo, femboy

TrannyOne

SISSY SMOKING BIMBO HYPNO

Categories: bimbo, hardcore, sissy, smoking

aShemaleTube

FEMBOY ANAL TUTORIAL

Categories: anal, big cock, cumshot, femboy, fetish, hd, sissy, solo, toys

aShemaleTube

Ancelina Sexy Blonde Girl FishnEt Lingerie

Categories: amateur, big ass, blonde, crossdressing, femboy, fetish, fishnet, hd, lingerie, outdoor

KeekAss

Outdoor walk in semi-transparent watch thru mini sundress

Categories: amateur, anal, ass, dress, femboy, fetish, hd, masturbation, outdoor, panties

ShemaleMovie

Kellystar518 reigns as the ultimate cum queen!

Categories: american, anal, anal toying, beauty, big black cock, cum, cumshot, dildo, high heels, huge dildo

KeekAss

TRANSGIRL LIKING PARK HILL THUG GETS MOUTH SERVICED

Categories: amateur, blonde, blowjob, crossdressing, cum in mouth, cumshot, facial, femboy, hd, homevideo

TrannyOne

Sperma Trainer

Categories: big cock, blowjob, compilation, creampie, cum in mouth, cum swallowing, cumshot, german, pov, sissy

aShemaleTube

Princess Peaches 🍑

Categories: big tits, crossdressing, hd, lingerie, mature, pornstar, sissy, stockings

Pornstars: Peaches

HDSex

Sissy toys and latex magic for the ultimate sissy experience

Categories: crossdressing, deep throat, dildo, latex, riding, sissy, toys

aShemaleTube

Boy squirts Cum and Piss while Riding Cock like a Sissy Femboy Prostate Sperm Milking in Lingerie

Categories: anal, bisexual, boy, cum, dick, extreme, femboy, indian, lingerie, milk

aShemaleTube

RUFUS Cheats on Girlfriend with Faggyboi

Categories: blowjob, crossdressing, ebony, femboy, gay, girlfriend, hd, sissy

KeekAss

XXL booty lil lollipop t-model cougar ravaging her bootie with ginormous touy and a pound machine

Categories: anal, ass, ass to mouth, assfingering, big ass, booty, cougar, fat, feminization, gaping hole

JizzBunker

Sissy play outdoors. dildo riding in the forest

Categories: amateur, anal, crossdressing, dildo, forest, hardcore, huge dildo, lingerie, masturbation, nude

KeekAss

faux-cock rail before going to couch

Categories: amateur, anal, anal toying, assfucking, couch, creampie, crossdressing, dick, hd, homevideo

KeekAss

sissy crossdresser converses to her staff

Categories: amateur, big tits, blonde, british, crossdressing, dirty talk, fetish, hd, high heels, homevideo

aShemaleTube

Cute White Femboy Wedgie Punished and Anal Fucked

Categories: anal, big ass, crossdressing, cute, dildo, femboy, fetish, gaping hole, hd, masturbation

VideoSection

Role play, pantyhose

Categories: british, crossdressing, high heels, lingerie, masturbation, panties, pantyhose, sissy, stockings, underwear

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

aShemaleTube

BALD SEXY vs Faggyboi

Categories: big tits, blowjob, crossdressing, ebony, fake tits, femboy, hairless, hd, lingerie, pov

aShemaleTube

College Boy Meets Sissy At Bar And Then Fucks

Categories: amateur, anal, bar, big cock, blonde, boy, college, creampie, crossdressing, hd

HClips

Sissy 4 Min

Categories: amateur, big cock, hd, latina, phone, sissy, small tits, solo, stockings, webcam

aShemaleTube

Yuppish Whispers Lick My Candy Heart

Categories: beauty, college, compilation, cosplay, crossdressing, cumshot, femboy, licking, masturbation, pretty

aShemaleTube

Total Slut For Raw Cock Jackie

Categories: barebacking, big ass, blowjob, crossdressing, dick, sissy, slut, small cock

TrannyOne

Mistress Her Sissy Gurl Cum

Categories: cum, gay, mistress, sissy

aShemaleTube

CD Sarah, in blue velvet, smokes, drinks own piss, masturbates to cumshot

Categories: blonde, crossdressing, cumshot, femboy, fetish, hd, masturbation, mature, model, piss drinking

JizzBunker

Grindr Sissy SissyWave Brainwash Sissy Captions Feminization

Categories: amateur, anal, big cock, compilation, creampie, feminization, gay, hardcore, sissy, solo

KeekAss

Transsexual Bunny Romps Sissy femboy

Categories: amateur, anal, big ass, brunette, bunny, creampie, crossdressing, femboy, femdom, hardcore

KeekAss

crossdresser prays chief to let her wear a different clothing

Categories: amateur, big tits, british, crossdressing, fetish, hd, high heels, homevideo, lingerie, mature

TrannyOne

Paulina's night of Quickies

Categories: amateur, anal, anus, ass, big cock, crossdressing, cum, dick, gay, hd

aShemaleTube

Playing at home

Categories: amateur, anal, crossdressing, dildo, homevideo, ladyboy, latina, lingerie, mature, milf

aShemaleTube

Nina's cumshots compilation (updated!)

Categories: big cock, compilation, crossdressing, cumshot, hd, lingerie, masturbation, pantyhose, pov, sissy

ShemaleMovie

Tiffany Ciskiss as Tigra gets wild with massive toys in femboy cosplay

Categories: american, anal, anal toying, ass, cosplay, crossdressing, dildo, european, extreme, femboy

aShemaleTube

MangoK cums handsfree anal then jerks & cums again 🍆💦💦

Categories: anal, big cock, cum, cumshot, hd, masturbation, orgasm, prostate, sissy, small tits

XXXDan

Big cock tranny Lucy gets a sloppy deepthroat blowjob from sissy Charlotte

Categories: amateur, bdsm, big cock, big tits, blowjob, british, couple, crossdressing, deep throat, european

aShemaleTube

Sexy Shemale Is Dancing On a 11-inch BBC Dildo

Categories: amateur, big black cock, dancing, dildo, hd, homevideo, model, sissy, tgirl, tranny

aShemaleTube

Sissy slut fucks anal with her fingers and cums handsfree

Categories: amateur, anal, compilation, crossdressing, cum, cumshot, fingering, hd, lingerie, masturbation

aShemaleTube

Full Sissy Play - G041.1

Categories: amateur, anal, asian, crossdressing, femboy, hd, homevideo, interracial, model, sissy

KeekAss

Crossdresser Maid Taylor Needs Raw Hotel Guest Cock

Categories: blonde, blowjob, crossdressing, dick, femboy, hd, hotel, maid, pov, sissy

ShemaleMovie

Sissy in tiny bikini swallows a beer while getting ass-fucked outdoors, then struts around to flaunt herself

Categories: amateur, anal, assfucking, bikini, crossdressing, cum swallowing, enema, homevideo, humiliation, ladyboy

aShemaleTube

horny secretary milf on couch self facial big cumshot

Categories: amateur, couch, cumshot, facial, hd, homevideo, lingerie, lipstick, milf, model

aShemaleTube

Upskirts to flash my sissy ass in 9" BBC SLUT platform stiletto heels to tease BB12"NCs

Categories: ass, big ass, big black cock, blonde, crossdressing, femboy, fetish, flashing, hd, high heels

KeekAss

sissy sarah cushion humper

Categories: abuse, amateur, bdsm, crossdressing, fetish, high heels, humiliation, humping, ladyboy, lingerie

ShemaleMovie

Olivia locks up my pecker in a chastity cage

Categories: ass, babe, beauty, big ass, big cock, cage, femboy, sissy, small cock, small tits

aShemaleTube

BBC fuck pasivo en tanga PT1

Categories: amateur, anal, big black cock, big cock, crossdressing, femboy, hd, interracial, ladyboy, latina

KeekAss

Noiseless Assfuck Getting off and protracted Mitts Free-for-all Jizm in a motel on a biz journey.

Categories: anal, asian, assfucking, crossdressing, cum, cumshot, dildo, femboy, hd, japanese

aShemaleTube

TS Cares Saxo 2

Categories: sissy, small cock, solo, transsexual

JizzBunker

Sissy anal dildo and papieros

Categories: amateur, anal, anal toying, dildo, european, masturbation, polish, sissy, smoking, solo

KeekAss

Tiffany Ciskiss Has A Lovely Booty Dressed In Xl Glass Culo Ass-Plug

Categories: amateur, anal, anal toying, ass, bathroom, booty, crossdressing, femboy, hd, homevideo

aShemaleTube

Nail painting

Categories: feet, hd, mistress, polish, sissy, submissive, toes

ShemaleMovie

Hot guy takes my young femboy ass hard and deep

Categories: anal, ass, big ass, blowjob, creampie, cum, cumshot, femboy, gaping hole, jizz

aShemaleTube

Femboy Camsluts 3

Categories: anal, blonde, femboy, sissy, webcam

KeekAss

Trav and nymph

Categories: amateur, cosplay, crossdressing, dick, girlfriend, hd, lingerie, pussy, sissy, solo

ShemaleMovie

Hidden camera captures sissy crossdresser embracing girly clothing in a feminine way – part 2

Categories: amateur, british, crossdressing, hidden cam, high heels, lingerie, pantyhose, sissy, stockings, teen (18+)

aShemaleTube

skinny and tall teen shemale cutie tugs her small dick on webcam

Categories: amateur, cute, femboy, homevideo, jerking, masturbation, sissy, skinny, small cock, small tits

aShemaleTube

BTS POV sex with Aliza Breeze

Categories: amateur, anal, crossdressing, ebony, femboy, hd, interracial, pornstar, pov, sissy

Pornstars: Aliza

aShemaleTube

Latex mature shemale fuck a slutty tranny

Categories: domination, dominatrix, fetish, hd, latex, mature, sissy, slut, submissive, tranny

aShemaleTube

Cute blonde in lace dress and hold-up stockings

Categories: big cock, blonde, crossdressing, cute, dress, femboy, hd, lace, ladyboy, lingerie

aShemaleTube

Gothic Sissy Tranny Walking In Public with Dick Exposed Under Skirt and Butt Plug

Categories: amateur, buttplug, crossdressing, dick, femboy, fetish, goth, hd, outdoor, public

KeekAss

BEHIND THE SCENES POINT OF VIEW hookup with Ash Steele

Categories: amateur, anal, assfucking, behind the scenes, blowjob, brunette, crossdressing, femboy, feminization, handjob

ShemaleMovie

Naughty shemale Eva Joi's tight asshole destroyed by huge cock of tranny slut Hatler Gurius

Categories: anal, ass, ass to mouth, assfingering, big cock, huge cock, joi, masturbation, naughty, orgasm

aShemaleTube

TsOmaina hot blonde transgirl fucking the neighbor

Categories: amateur, anal, barebacking, big ass, big cock, blonde, femboy, fetish, hd, ladyboy

KeekAss

男の娘オナニ－ Chinese crossdresser taunting

Categories: amateur, asian, brunette, chinese, cosplay, crossdressing, femboy, handjob, hd, japanese

aShemaleTube

Pantyluvn sissy white wood

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

aShemaleTube

Jenna Bella

Categories: ass, big cock, crossdressing, femboy, hd, high heels, lingerie, masturbation, pussy, shaved

aShemaleTube

Cute femboy showing off lace gloves playfully

Categories: beauty, college, cosplay, crossdressing, cum, cumshot, cute, femboy, gloves, lace

KeekAss

Sean Carey sissy faggot shemale

Categories: crossdressing, dick, fetish, gay, ladyboy, sissy, solo

aShemaleTube

Freckled femboy edging with big dildo 🍆

Categories: big cock, dildo, edging, femboy, freckled, hd, homevideo, masturbation, sissy, small tits

aShemaleTube

Sissy TS stretching in sexy yoga pants xhrk98o

Categories: amateur, asian, hd, sissy, solo, transsexual, yoga

aShemaleTube

Mature couple tease tattoo sissy Charlotte with a dildo and magic wand vibrator

Categories: 3some, amateur, blonde, british, couple, crossdressing, dildo, english, hd, mature

aShemaleTube

Wanking and cumming with a big dildo in my ass

Categories: amateur, anal, ass, crossdressing, cum, cumshot, dildo, hd, homevideo, masturbation

KeekAss

Rigid Man meat Makes Satin Undies Sloppy

Categories: balls, cute, dick, femboy, fetish, handjob, hd, legs, lingerie, masturbation

aShemaleTube

Deana transformed herself in a bisexual girl part 1

Categories: amateur, bisexual, crossdressing, masturbation, mature, sissy, slut, solo, transvestite, vibrator

KeekAss

Feminization Sissification SISSY TASK - Going to a fuck-a-thon shop_2

Categories: amateur, crossdressing, femdom, feminization, fetish, hd, joi, lingerie, pov, sissy

HDSex

Transgender boy girl, fuck hard crying girl, ladi boy and girl

Categories: babe, big cock, boy, creampie, crying, hardcore, sissy

KeekAss

CDSimone in Catsuit is Mastrubating and Playing her Butt

Categories: amateur, anal, anal toying, ass, catsuit, crossdressing, hd, lingerie, masturbation, redhead

aShemaleTube

Kellycd2022 in Pink Seamless Pantyhose

Categories: big cock, big tits, british, crossdressing, cumshot, english, hd, lingerie, masturbation, mature