Crossdressing Shemale Videos » 32

XXXDan

Sissy-Kuroko Huge Anal Plug

Categories: amateur, anal, asian, big ass, cosplay, crossdressing, dildo, hardcore, japanese, masturbation

KeekAss

Packing my fuckhole while dressed in my stripper stilettos

Categories: amateur, anal, assfucking, buttplug, crossdressing, cumshot, dildo, hd, homevideo, masturbation

ShemaleZ

Crossdresser Without Makeup Plays In Kitchen

Categories: amateur, crossdressing, hd, kitchen, solo, toys, webcam

aShemaleTube

Josydelicia Anal Fetiche Dildos Farting Brasil

Categories: amateur, anal, brazilian, crossdressing, dildo, farting, homevideo, masturbation, solo, toys

aShemaleTube

Sucking and fingering a latex crossdresser

Categories: amateur, blowjob, crossdressing, fingering, hd, homevideo, latex, mature, sucking

aShemaleTube

Sexy Blowjob

Categories: anal toying, beauty, blowjob, colombian, crossdressing, cumshot, hd, homevideo, ladyboy, lingerie

XXXDan

Transvestite sissy crossdresser sounding urethral lingerie a

Categories: amateur, bdsm, big cock, crossdressing, hardcore, lingerie, masturbation, mature, nude, public

aShemaleTube

HA60Sexy teacher gets fucked anal squirted in class while writing down exam content

Categories: anal, asian, big ass, chinese, crossdressing, cumshot, hd, model, sissy, squirt

XXXDan

Dominatrix fucks a sexy sissy in chastity

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

aShemaleTube

Satin & cum

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

KeekAss

TVMandySpencer buttplugs her thick bubblebutt and gets rock hard solo

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

UPornia

This Cute Crossdresser Wont Be Able To Walk

Categories: amateur, crossdressing, cute, webcam

VideoSection

Sissy training session in sexy undies and pantyhose

Categories: amateur, crossdressing, cumshot, lingerie, masturbation, pantyhose, sissy, solo, stockings, underwear

KeekAss

Emo Trans Doll Lindsey Autumn Wanks Off Humungous Knob In Super-sexy Crimson Sundress

Categories: big cock, cosplay, crossdressing, cute, doll, emo, goth, handjob, hd, huge cock

XXXDan

Blowjob and bukkake from Japanese crossdresser b06

Categories: blowjob, bukkake, crossdressing, japanese

XXXDan

Sissy maid femboy cosplay British young tranny masturbates to cum

Categories: amateur, british, cosplay, crossdressing, cum, cumshot, european, femboy, fetish, lingerie

KeekAss

Periodically a woman just needs to take care of her own knob

Categories: amateur, beauty, big cock, big tits, crossdressing, cum, cumshot, french, gay, handjob

KeekAss

Meaty insatiable booty fuckslut

Categories: amateur, anal, ass, bbw, big ass, bitch, black, booty, brazilian, chubby

aShemaleTube

spread legs mirror 1

Categories: amateur, crossdressing, hd, homevideo, ladyboy, legs, lingerie, mirror, solo, spreading

aShemaleTube

Amatuer CD Rides Her Toy

Categories: amateur, anal, asian, chinese, crossdressing, femboy, pantyhose, sissy, small tits, solo

aShemaleTube

Holly wanking in the forest

Categories: crossdressing, cum, forest, hd, mature, stockings, wanking

ShemaleMovie

German teenager Tight Tini gets pounded by crossdresser transsexual at user meetup

Categories: big cock, big tits, crossdressing, german, small cock, teen (18+), tight, transsexual

JizzBunker

Fat Crossdresser Getting pounded By hirsute guy

Categories: bbw, crossdressing, fat, hirsute

XXXDan

Amateur shemale with corset, stockings and boots masturbates, fucks a boot and cums on herself

Categories: amateur, beauty, boots, corset, crossdressing, cum, cumshot, fetish, hardcore, lingerie

aShemaleTube

Cum in my ass cum analsys big ass crossdresser heels stocking spandex amateur

Categories: amateur, ass, big ass, compilation, crossdressing, cum, cumshot, fetish, hd, high heels

KeekAss

Ciggies and getting off

Categories: amateur, big tits, cigarette, crossdressing, fetish, handjob, hd, homevideo, kinky, masturbation

KeekAss

Fat arse transgender princess tart marvelous twerk ladyboy tranny bouncy caboose

Categories: amateur, ass, big ass, booty, brunette, crossdressing, fat, hd, ladyboy, latina

HClips

Seule Au Monde

Categories: amateur, blonde, crossdressing, masturbation, solo

aShemaleTube

At the cruising area dressed up I'm my stockings and tight skirt

Categories: crossdressing, cruising, hd, mature, outdoor, skirt, stockings, tight

XXXDan

April Bee Short Hair Reveal JOI

Categories: amateur, asian, bdsm, beauty, big cock, blonde, british, crossdressing, fetish, joi

aShemaleTube

Mature tranny holly wanking her girl cock and cumming in the woods

Categories: amateur, crossdressing, cum, cumshot, dick, hd, masturbation, mature, model, outdoor

XXXDan

Big cock and big tits tranny Lucy jerks off and cums in an orange jersey dress

Categories: amateur, big cock, big tits, british, crossdressing, cum, cumshot, dress, masturbation, mature

KeekAss

@tsmollybabe rails a massive fuck stick

Categories: amateur, anal, beauty, crossdressing, hd, homevideo, huge dildo, masturbation, stockings, toys

aShemaleTube

Sitting At My Computer

Categories: amateur, crossdressing, hd, homevideo, lingerie, pantyhose, stockings, upskirt

KeekAss

Handsome Sissy Crossdresser Corset Leather Belt Tights High Stilettos Arse Nylon Pantyhose

Categories: amateur, ass, bdsm, beauty, blonde, corset, crossdressing, fetish, hd, high heels

HClips

Tranny Bimbo's Bondage and Breathplay Predicaments

Categories: amateur, bdsm, bondage, breath play, crossdressing, fetish, hd, tranny

aShemaleTube

Trans Kelsey Masters Fucking and Blowjobs - Compilation 5

Categories: amateur, american, anal, beauty, big ass, blowjob, compilation, crossdressing, femboy, hd

aShemaleTube

I couldn’t fit it into my little mouth…

Categories: amateur, blowjob, crossdressing, deep throat, glasses, hd, high heels, homevideo, nerdy, sissy

JizzBunker

Crossdresser Cosplay Party 1

Categories: cosplay, crossdressing, party

aShemaleTube

Dizzy Bound and takes Masters Cock

Categories: bdsm, blowjob, bondage, bound, crossdressing, dick, domination, hd, lingerie, sissy

KeekAss

Femboy self restrain bondage in rosy

Categories: amateur, anime, bondage, cosplay, crossdressing, cute, femboy, hd, homevideo

KeekAss

Popshot in Stretch Pants

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

TrannyOne

Walk in the woods (again)

Categories: amateur, crossdressing, cum, cumshot, forest, gay, hd, masturbation, nature, orgasm

aShemaleTube

Blonde in blue stockings and red bra

Categories: blonde, bra, crossdressing, femboy, hd, ladyboy, lingerie, masturbation, pantyhose, sissy

aShemaleTube

Sissy femboy loves blowjob and getting fucked and swallowing cum

Categories: anal, blowjob, creampie, crossdressing, cum, cum in mouth, cum swallowing, cumshot, femboy, hd

ShemaleMovie

Riding session with a sexy sissy in lingerie

Categories: beauty, blonde, braces, crossdressing, femboy, fishnet, jerking, ladyboy, lingerie, masturbation

XXXDan

CFNM straps transvestite ass with dildo while jerking off

Categories: amateur, ass, babe, big ass, cfnm, crossdressing, dildo, femdom, fetish, handjob

KeekAss

Femboi Beauty Enjoys Playing

Categories: amateur, beauty, big cock, big tits, brunette, crossdressing, feet, femboy, homevideo, huge cock

aShemaleTube

Rachelarcher - Russian Crossdresser Open Ass

Categories: amateur, anal, ass, blonde, crossdressing, femboy, glasses, hd, homevideo, lingerie

KeekAss

Plugged Sissy In Sheer Silk & Glossy Satin

Categories: amateur, anal, bdsm, blonde, crossdressing, cum, cumshot, fetish, hd, high heels

TrannyOne

Two huge cock shemales blowjob handjobs

Categories: amateur, anal, anus, ass, assfingering, bdsm, big cock, black, blowjob, crossdressing

TrannyOne

Black bodystockings femboy fucked by jock after deepthroat

Categories: amateur, black, crossdressing, deep throat, femboy, fetish, gay, hd, skinny, tattoo

aShemaleTube

Milk Machine

Categories: amateur, compilation, crossdressing, cum, cumshot, fetish, fucking machine, hd, huge cock, ladyboy

aShemaleTube

CdTina pov

Categories: amateur, big cock, crossdressing, fetish, hd, lingerie, long nails, masturbation, mature, pov

aShemaleTube

Sissy Crossdresser Annette quick motel blowjob and facial

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

XXXDan

Patty French maid

Categories: amateur, cosplay, crossdressing, european, french, lingerie, maid, masturbation, milf, solo

KeekAss

Kinky Tgirl Butt Fucking Boyfriend

Categories: amateur, asian, assfucking, beauty, blonde, blowjob, boyfriend, crossdressing, dick, dildo

Pornstars: Vixxxen

aShemaleTube

Piss lover compilation

Categories: compilation, crossdressing, fetish, hd, piss drinking, pissing

KeekAss

SISSY BEAVER. Munching tastey uber-cute candy she-creature bod, white dhemale hory PLUMPER crossdresser

Categories: amateur, beauty, beaver, big ass, big cock, couple, crossdressing, cute, fetish, hd

aShemaleTube

4 differnet tights

Categories: amateur, big cock, big tits, crossdressing, femboy, fetish, hd, outdoor, sissy, solo

aShemaleTube

kamsinkamya loves licking dirty underwear

Categories: amateur, crossdressing, dirty, hd, indian, licking, underwear

aShemaleTube

Marilyn Blows Her Cum

Categories: amateur, big ass, big cock, blonde, crossdressing, cum, cumshot, fetish, hd, latex

JizzBunker

High socks mini skirt crossdress

Categories: crossdressing, fetish, miniskirt, socks

XXXDan

Tranny Ass Milk Squirt Compilation 3

Categories: amateur, anal, ass, big ass, british, compilation, crossdressing, european, fetish, lingerie

KeekAss

Joanie - Lace Overlay Bustier two

Categories: amateur, blonde, crossdressing, cumshot, hd, lace, lingerie, masturbation, mature, stockings

KeekAss

Going Knuckle Deep Deep Buttplug Inhaling Machine

Categories: amateur, anal, anal fisting, ass, big black cock, blonde, buttplug, crossdressing, deep throat, face fucking

aShemaleTube

fucking crossdresser bitch bdsm

Categories: amateur, ass to mouth, bdsm, big tits, bitch, crossdressing, domination, ladyboy, mature

aShemaleTube

CD Cums Hands Free Prostate HFO Compilation surfboardpo

Categories: compilation, crossdressing, cum, prostate

VideoSection

Recent live orgy with Gigi and Dave - a hot shemale and couple experience

Categories: anal, blowjob, couple, crossdressing, homevideo, kissing, orgy, sensual

aShemaleTube

Two Sissys having Fun together - Part 2: Fucking

Categories: amateur, anal, crossdressing, femboy, funny, hd, homevideo, lesbian, lingerie, sissy

aShemaleTube

Butt Girl Tiffany Ciskiss Fucks Round Sissy Ass On XXL Ribbed Dildo In Bluejean Skirt

Categories: amateur, anal, ass, crossdressing, dildo, femboy, hd, model, pantyhose, sissy

JizzBunker

Hot goth trans woman fucked in missionary position

Categories: amateur, anal, beauty, big ass, crossdressing, fetish, goth, hardcore, missionary, tattoo

KeekAss

obese sissy jacking off

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

aShemaleTube

Japanese Sissy Mistress StrapOn temptaion

Categories: amateur, asian, crossdressing, fetish, hd, homevideo, japanese, latex, mistress, model

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

aShemaleTube

Serbian tranny.mp4

Categories: amateur, blowjob, crossdressing, cumshot, group sex, homevideo, mature, serbian, tranny

aShemaleTube

Aian CD Cums Riding Cock

Categories: amateur, asian, barebacking, chinese, crossdressing, cum, dick, femboy, fetish, hd

aShemaleTube

Blonde in a hot pink bodystocking

Categories: blonde, bodystocking, crossdressing, femboy, fetish, hd, ladyboy, lingerie, masturbation, pantyhose

aShemaleTube

Smoking Sissy Slut Deepthroats Her Step-daddy

Categories: blowjob, crossdressing, cum in mouth, cumshot, daddies, deep throat, femboy, hd, lingerie, masturbation

Pornstars: Viper

aShemaleTube

Anna The Temptress

Categories: big cock, big tits, crossdressing, hd, lingerie, masturbation, pantyhose, pornstar, solo, stockings

Pornstars: Temptress

JizzBunker

Goth tranny fucked in missionary position

Categories: amateur, anal, beauty, big ass, big cock, crossdressing, fetish, goth, hardcore, lingerie

aShemaleTube

Japanese Sissy slave solo cum (non cut Ver)

Categories: amateur, asian, crossdressing, cum, cumshot, fetish, hd, homevideo, japanese, latex

aShemaleTube

Unboxing our huge new dildo's from John Thomas Toys

Categories: amateur, big tits, crossdressing, dildo, dirty talk, hd, homevideo, mature, model, redhead

aShemaleTube

Japanese CD Musterbation at Balcony KaoruAsahina p

Categories: balcony, crossdressing, hd, japanese

aShemaleTube

Crossdresser Sissy in High heels fucked by daddy

Categories: amateur, anal, asian, blowjob, crossdressing, daddies, femboy, fetish, hd, high heels

aShemaleTube

A Slut in a Grove (june 29, 2025) Looking for Cocks. French Transvestite Exhibition Vanessabitchx

Categories: amateur, big ass, crossdressing, dick, european, exhibitionist, fishnet, french, hd, high heels

KeekAss

Horny Hot Tranny Faps Her Dick

Categories: amateur, beauty, crossdressing, cute, dick, girlfriend, homevideo, kissing, masturbation, redhead

aShemaleTube

Crossdressers group sex in hotel room

Categories: blowjob, crossdressing, group sex, hd, homevideo, hotel

KeekAss

Lean CD fuckslut in underwear smashes fucktoys and ejaculates

Categories: amateur, anal, assfucking, crossdressing, cumshot, fishnet, handjob, hd, huge dildo, kinky

aShemaleTube

Natacha Mancinelli with her fuck machine

Categories: amateur, crossdressing, dildo, fucking machine, hd, lingerie, model, sissy, slut, solo

aShemaleTube

crossdress VID_20250213_212634

Categories: amateur, asian, big ass, chinese, crossdressing, fetish, hd, homevideo, lingerie, masturbation

aShemaleTube

A friend’s wishes

Categories: anal, crossdressing, friend, hd, huge dildo, toys, tranny

aShemaleTube

Sissy's Public Restroom Anal Encounter

Categories: amateur, anal, asian, crossdressing, hd, homevideo, model, public, sissy, taiwanese

aShemaleTube

Lostwind Comp1

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

JizzBunker

Smoking in black lingerie

Categories: amateur, black, british, crossdressing, fetish, handjob, high heels, lingerie, masturbation, mature

KeekAss

HEADPHONE WARNING Instructing backside to take XL Atlas Mr Hanky Fucktoy deeper, painal gape

Categories: amateur, anal, anal toying, assfucking, crossdressing, dildo, extreme, gaping hole, hd, homevideo

KeekAss

Joanie - Lace Overlay Bustier

Categories: amateur, blonde, crossdressing, cumshot, hd, lace, lingerie, masturbation, mature, stockings

KeekAss

Symmetric bombshell all-natural neat tranny knob and cool gentle gams clapping onanism

Categories: amateur, asian, ass, beauty, big cock, bombshell, couple, crossdressing, fetish, hd

aShemaleTube

Big Cock TGirl and MILF face fucking and bareback anal fun

Categories: amateur, anal, barebacking, big cock, big tits, blowjob, crossdressing, face fucking, funny, hd

ShemaleMovie

Shemale riding dildo, sissy crossdresser

Categories: anal, anal toying, ass, bathroom, crossdressing, dildo, fishnet, fisting, gaping hole, huge dildo

TrannyOne

Handjob for femboy's hard and big cock - Horny POV

Categories: amateur, big cock, blonde, close up, couple, crossdressing, cum, cumshot, dick, femboy

JizzBunker

Straight guy likes to feel like a transvestite

Categories: amateur, anal, big cock, crossdressing, dildo, erotic, handjob, hardcore, high heels, lingerie

aShemaleTube

Cat Walk

Categories: buttplug, crossdressing, feet, hd, high heels, sissy, stockings, upskirt

aShemaleTube

My pig open my anal pussy

Categories: anal, assfingering, crossdressing, hd, pussy

TrannyOne

Blonde shemale self sucks cock & balls - dailyTS.com webcams

Categories: 18 year old, adorable, amateur, anal, anus, ass, babe, balls, beauty, big cock

aShemaleTube

Super Shy Femboy Fucked By Daddy

Categories: amateur, anal, big ass, blowjob, crossdressing, daddies, femboy, fetish, hd, homevideo

aShemaleTube

joanna bitch slave 2

Categories: anal, ass to mouth, barebacking, big cock, bitch, crossdressing, cum in mouth, domination, hd, mature

XXXDan

Chatty crossdresser tries out new depth - 2023-02-23 - part 1 - known territory

Categories: amateur, anal, caught, crossdressing, french, hardcore, lingerie, solo, toys

KeekAss

Amazing Hot Shemale Show Off

Categories: amateur, amazing, american, beauty, crossdressing, ebony, glasses, hd, homevideo, jizz

XXXDan

We need more and more toys. Till Godzilla

Categories: anal, crossdressing, dildo, german, hardcore, huge dildo, lingerie, piercing, solo, teen (18+)

aShemaleTube

[R18+] Pink Bunny Solo Cum and Drink Sperm

Categories: amateur, asian, bunny, crossdressing, cum, cumshot, fetish, hd, homevideo, latex

KeekAss

Female Domination Faux-Cock Encouragement Inhale my Stiffy Sissy POINT OF VIEW Rollplay

Categories: amateur, anal, blonde, cei, crossdressing, cum, cumshot, dick, dildo, domination

aShemaleTube

Big Cock TGirl Lucy POV masturbation in the bathroom

Categories: amateur, bathroom, big cock, big tits, crossdressing, cumshot, dick, hd, homevideo, masturbation

aShemaleTube

Midnight Solo (Crossdresser) (2025)

Categories: amateur, anal, asian, crossdressing, hd, homevideo, masturbation, small cock, solo, toys

ShemaleMovie

Tgirl Riley enjoys raw fucking in meeting #6 PartII

Categories: amateur, anal, barebacking, big cock, crossdressing, dick, european, femboy, gaping hole, lingerie

aShemaleTube

Beauty Great Body Jerking

Categories: amateur, beauty, crossdressing, cute, daddies, homevideo, jerking, leather, masturbation, solo

aShemaleTube

Outdoor piss in mouth

Categories: amateur, crossdressing, hd, mature, outdoor, piss drinking, pissing

KeekAss

【Bocchi the Rock】

Categories: amateur, anal, anime, asian, chinese, cosplay, crossdressing, femboy, handjob, hd

KeekAss

Sissy Lucy POINT OF VIEW Urinate and jacking in the douche

Categories: amateur, big cock, big tits, brunette, crossdressing, dick, homevideo, huge cock, masturbation, mature

aShemaleTube

Big Tits Smoking Fetish Mistress

Categories: amateur, big tits, crossdressing, fetish, gloves, hd, latex, mature, mistress, smoking