Crossdressing Shemale Videos » 24

KeekAss

2 obese ladyboys havign a threeway with a damsel

Categories: 3some, amateur, bbw, big ass, big cock, big tits, blonde, blowjob, brunette, chubby

aShemaleTube

Blair Being Herself

Categories: amateur, crossdressing, cumshot, femboy, hd, lingerie, sissy, small tits, solo

aShemaleTube

👑Sissie Soubrette Soumise & Pute Dominante. Coffee, Tea or Me Vanessabitchx

Categories: amateur, bimbo, blowjob, crossdressing, cum in mouth, facial, french, hd, sissy, slut

XXXDan

Misr4 - cumshot on stockings

Categories: big cock, close up, crossdressing, cumshot, fetish, lingerie, masturbation, mature, panties, polish

KeekAss

White ASH-BLONDE Orbs MASSIVE Guy CUPCAKES Steamy HOMOSEXUAL Crossdresser SISSY Femboy Model

Categories: amateur, babe, big ass, blonde, booty, brunette, college, crossdressing, cum, cute

aShemaleTube

HollyEmidscd in black bodystocking and sexy heels playing with herself...

Categories: amateur, black, bodystocking, crossdressing, hd, high heels, lingerie, masturbation

aShemaleTube

Handsfree cum in chastity

Categories: amateur, buttplug, crossdressing, cum, cumshot, hd, homevideo, sissy, solo

aShemaleTube

crossdresser punishment

Categories: ass, bdsm, crossdressing, domination, fetish, pain, punishment, spanking

aShemaleTube

Denim Dress on the Bed

Categories: amateur, bed sex, compilation, crossdressing, dress, homevideo, jeans, webcam

aShemaleTube

Horny Dazzling TGirl Fucking her Cute Crossdressing BF

Categories: amateur, anal, babe, barebacking, beauty, boyfriend, crossdressing, cute, hd, homevideo

aShemaleTube

Simin

Categories: amateur, asian, big cock, blowjob, crossdressing, cum in mouth, femboy, hd, homevideo, interracial

aShemaleTube

Crossdresser in fur cums strong

Categories: amateur, big cock, crossdressing, cum, cumshot, fur, hd, masturbation, mature, pov

aShemaleTube

Cute slut cums on cam

Categories: amateur, crossdressing, cum, cumshot, cute, femboy, hd, masturbation, sissy, slut

aShemaleTube

Tranny smoking and showing her panties

Categories: amateur, boots, british, crossdressing, hd, model, panties, smoking, solo, stockings

KeekAss

Alternative transgirl being smacked my dommy doll

Categories: amateur, ass, big cock, brazilian, crossdressing, doll, domination, dominatrix, dyed hair, femboy

aShemaleTube

Sexy thick Turkish crossdresser fucked in her big ass

Categories: amateur, anal, assfucking, big ass, crossdressing, hardcore, hd, thick, tranny, turkish

KeekAss

Sissy has SissyGasm arched over like a Supreme Chick

Categories: amateur, anal, ass, bbw, crossdressing, dick, hd, mature, orgasm, sissy

aShemaleTube

Christmas greetings from secret santa bunny Harin! Got dildos as a present and gave you a deep

Categories: amateur, anal, anal toying, asian, big tits, blowjob, bunny, cosplay, crossdressing, dildo

FetishPapa

Vicious very matures shemales use a slave guy

Categories: 3some, amateur, anal, crossdressing, domination, hd, humiliation, mature, pissing, punishment

JizzBunker

Getting fucking deep in my ass by my huge dildos

Categories: amateur, anal, ass, big ass, crossdressing, dildo, dutch, fetish, hardcore, huge dildo

XXXDan

Dilation and lots of hot, wet cum came out of my friend intent on a transex

Categories: big cock, compilation, crossdressing, cum, cumshot, friend, gay, german, masturbation, nude

TrannyOne

Innocent trans passionately rides and sucks cock

Categories: amateur, anal, barebacking, beauty, big cock, blowjob, couple, crossdressing, dick, femboy

KeekAss

Motel Ass-Fuck Faux-Cock Venture

Categories: amateur, anal, assfucking, blonde, british, crossdressing, cum, cumshot, dick, dildo

KeekAss

Kellystar518 in LOVE your GODDESS

Categories: amateur, amazing, beauty, bondage, boots, brunette, cosplay, crossdressing, fantasy, girlfriend

KeekAss

Getting my bum nailed by a seamonster

Categories: amateur, anal, boots, crossdressing, dildo, fantasy, gaping hole, hd, high heels, huge dildo

KeekAss

Awesome shemale monster beefstick meaty cum shot - TScamdolls.com

Categories: amateur, big cock, big tits, brunette, crossdressing, cumshot, dick, gay, handjob, hd

aShemaleTube

Crossdresser riding dildo with denim skirt and heels

Categories: amateur, anal, anal toying, crossdressing, dildo, fetish, hd, high heels, homevideo, jeans

ShemaleZ

Sissy Gets Grindr Bareback Fucked

Categories: amateur, anal, barebacking, blonde, blowjob, crossdressing, curly haired, lingerie, sissy, stockings

VideoSection

Beautiful Colombian transgender Missangell_ ready to dominate

Categories: amateur, anal, ass, babe, barebacking, bdsm, beauty, big ass, big black cock, big cock

XXXDan

Hot Scarfy Dress Mini Sexy Amateur Model Femboy Crossdresser

Categories: amateur, bbw, beauty, big ass, college, cosplay, crossdressing, dress, femboy, mature

JizzBunker

Sissy slut rides in Chastity

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

KeekAss

Christmas elf spunking using only viber

Categories: amateur, beauty, cosplay, crossdressing, cum, cute, dick, handjob, hd, ladyboy

KeekAss

HIM: Can you Gargle a Thick Meatpipe? Me: My hatch luvs them

Categories: amateur, big black cock, bitch, blowjob, crossdressing, cumshot, ebony, fetish, handjob, hardcore

KeekAss

SexGodENT Introduces HTX T-Model Transsexual Ashlynn & Pal

Categories: 3some, amateur, anal, big cock, black, blowjob, brunette, crossdressing, cum, cumshot

Pornstars: Houston

aShemaleTube

in white heels and black stockings doing anal things

Categories: anal, big ass, black, crossdressing, hd, high heels, masturbation, sissy, stockings, webcam

aShemaleTube

Mrs Samantha and Marina give each other blowjobs and fuck in Cowgirl style

Categories: amateur, anal, blonde, blowjob, couple, cowgirl, crossdressing, dutch, high heels, lingerie

XXXDan

Cum fetish PT. 7 of 8 - A very horny close up load

Categories: amateur, big cock, close up, crossdressing, cum, fetish, lingerie, masturbation, small tits, solo

aShemaleTube

Black Femboy Ezra_Kyle25 in Halloween bunny stocking pt 1

Categories: amateur, big ass, black, bunny, crossdressing, ebony, femboy, halloween, hd, homevideo

aShemaleTube

Sissy crossdresser Annette interracial motel suck and fuck

Categories: amateur, anal, blowjob, crossdressing, hd, homevideo, interracial, motel, sissy, sucking

KeekAss

TRANSSEXUAL-damsel Pubic Hair Getting Off

Categories: amateur, ass, big ass, blonde, crossdressing, cum, cumshot, feet, femboy, handjob

aShemaleTube

Vera Strumpf - Im Park

Categories: amateur, blonde, crossdressing, cumshot, lingerie, masturbation, outdoor, pantyhose, park, stockings

aShemaleTube

I feel like a slut today

Categories: amateur, bra, crossdressing, cumshot, hd, high heels, homevideo, slut, solo

TrannyOne

Crossdresser in Latex Double Anal Fisted and Pegged by

Categories: anal, anal fisting, anus, ass, crossdressing, double penetration, extreme, fisting, hardcore, hd

aShemaleTube

Tina Poses in Pink Skirt and Sexy One-piece Swimsuit

Categories: amateur, big ass, crossdressing, mature, sissy, skirt, small cock, small tits, swimsuit

aShemaleTube

Skinny femboy maxmilian

Categories: crossdressing, femboy, sissy, skinny, small tits

ShemaleMovie

Nasty Azu in Misa cosplay expresses her love and desire

Categories: amateur, anal, asian, ass, babe, beauty, big ass, brutal, chinese, cosplay

KeekAss

Sissy drained with an “buttfuck butt-plug in my backside” while dressed in a college uniform costume play.

Categories: anal, asian, assfucking, buttplug, college, costume, crossdressing, cute, femboy, handjob

aShemaleTube

Be like Her - by BerlinaFilms

Categories: compilation, crossdressing, hd, lingerie, music, pov, sissy

KeekAss

V-Card sissy Raine frolicking with XXL FAKE PENIS

Categories: amateur, anal, anal toying, big ass, cage, crossdressing, cute, dick, dildo, femboy

KeekAss

This lovely sissy gives a feet wank with a speculum in her lil' bum

Categories: amateur, anal, anal toying, big cock, crossdressing, cum, dildo, doggystyle, feet, fetish

HDSex

Adorable femboy with an amazing butt gets fucked hard

Categories: 18 year old, adorable, amazing, anal, ass, beauty, big ass, crossdressing, femboy, hardcore

KeekAss

Impressive Sissy Superslut BIG BLACK COCK Three-way With Ria Bentley and Lola Crystals

Categories: 3some, anal, barebacking, big black cock, creampie, crossdressing, cumshot, femboy, fetish, hd

KeekAss

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

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

aShemaleTube

Older Mexican CD sucks me off

Categories: amateur, big cock, blowjob, crossdressing, ebony, hd, latina, mature, mexican, old

KeekAss

Xxl Trans Man Rod Compilation

Categories: amateur, anal, big cock, blowjob, brunette, compilation, crossdressing, cum, cumshot, domination

KeekAss

trans damsel rails FAT Goliath from Hankey's Fucktoys

Categories: amateur, anal, anal toying, crossdressing, dildo, fat, hd, homevideo, huge dildo, ladyboy

aShemaleTube

Crossdresser BLOW s on the backseat

Categories: amateur, backseat, crossdressing

KeekAss

White Sissy Muslimah dressed in Hijab plays with Fuck Stick

Categories: amateur, anal, arab, crossdressing, dildo, hijab, masturbation, sissy, small tits, toys

aShemaleTube

De sentones me di en el dildo

Categories: crossdressing, dildo, fetish, lingerie, pantyhose

aShemaleTube

crossdress VID_20250207_165557

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

aShemaleTube

Pink Satin Corset Black Skirt (enhanced)

Categories: amateur, black, corset, crossdressing, cute, dildo, hd, homevideo, latina, lingerie

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

XXXDan

A young dirty little transvestite cums all over her face!

Categories: big ass, big cock, crossdressing, cum, dirty, lingerie, masturbation, small cock, small tits, solo

KeekAss

Sissy has ended everything

Categories: amateur, anal, assfucking, boy, crossdressing, cum, cumshot, cute, hd, homevideo

KeekAss

Sohimi Plaything - Pushing Masturbator Review Jessica Bloom

Categories: amateur, big cock, blonde, crossdressing, cum, cumshot, fleshlight, fucking machine, hd, huge cock

aShemaleTube

sexcretary 1

Categories: amateur, asian, crossdressing, homevideo, lingerie, masturbation, pantyhose, solo, stockings, uniform

aShemaleTube

👑ExhiB🚙P U B L I C en Pute sur un Parking en Foret, à La Faisanderie 91. Collant Fantaisy, String

Categories: amateur, big ass, crossdressing, fetish, forest, french, hd, outdoor, pantyhose, sissy

aShemaleTube

Holy fuck! (...the juicy way she sucks!)

Categories: amateur, big cock, blowjob, crossdressing, cum in mouth, cumshot, hd, homevideo, juicy, sucking

JizzBunker

Mrs Samantha has Blonde Tgirl Daphne fuck and ride her in Cowgirl style!

Categories: amateur, anal, blonde, couple, cowgirl, crossdressing, dutch, gay, hardcore, high heels

aShemaleTube

FEMBOY JERKING ON CAM AND CUM - Gay Porn - WebCam Gay Porn

Categories: big cock, crossdressing, cum, cumshot, femboy, gay, handjob, jerking, masturbation, pantyhose

TrannyOne

Hilomi Crossdresser Gay Love Sex Creampie 04

Categories: amateur, anal, anus, asian, ass, couple, creampie, crossdressing, cum, gay

KeekAss

Asian Crossdresser costume play Onanism 20151031 sample

Categories: amateur, anal, asian, big ass, costume, crossdressing, handjob, japanese, ladyboy, masturbation

aShemaleTube

Bois🌳de🗼Boulogne [9juil23] VaneSsaBiTCHx & Aline

Categories: club, crossdressing, hd

aShemaleTube

slim italian shemale in black lingerie jerks off her cock

Categories: amateur, black, crossdressing, dick, feet, homevideo, italian, jerking, legs, lingerie

KeekAss

Dirty Little Tranny Slut Smokes Meth

Categories: big cock, crossdressing, dirty, lingerie, masturbation, slut, small cock, stockings, tranny, transsexual

KeekAss

Ms 300 Sarazia Exotic Trickling Internal cumshot & Popshot

Categories: anal toying, beauty, big black cock, big cock, black, crossdressing, cum, cumshot, dick, exotic

XXXDan

Hot guy is a damn cool transvestite

Categories: amateur, big cock, crossdressing, cumshot, gay, hairy, handjob, masturbation, skinny, solo

KeekAss

ANIME ANGEL SHE-CREATURE NEURAL WORK DANCE

Categories: amateur, anime, blonde, cosplay, crossdressing, hd, lingerie, masturbation, music, webcam

KeekAss

Raw & Insane Bride - pissing and pop-shot in the douche

Categories: amateur, bdsm, blonde, bride, crossdressing, cum, cumshot, hd, high heels, homevideo

aShemaleTube

Crossdresser cumming compilation orgasmic wanking colle

Categories: amateur, compilation, crossdressing, cum, orgasm, wanking

aShemaleTube

Teen TS Shooting Big Loads

Categories: amateur, big cock, compilation, crossdressing, cumshot, homevideo, lingerie, pornstar, pov, solo

Pornstars: Rose Marie

KeekAss

Dance and slow rosy undies undress-off for my EBONY INSTRUCTOS.

Categories: amateur, ass, black, crossdressing, ebony, gay, homevideo, solo, stockings, striptease

aShemaleTube

Sissy Faye ass-fucked with legs in the air, red heels and stockings

Categories: assfucking, big black cock, crossdressing, fetish, hd, high heels, latex, legs, sissy, stockings

aShemaleTube

Riding and dripping little cock

Categories: anal, clit, crossdressing, dick, dildo, femboy, hd, ladyboy, lingerie, riding

aShemaleTube

Pearl1 big cock, redhead, corset, stockings , high heels, long nails

Categories: amateur, big cock, corset, crossdressing, hd, high heels, homevideo, long nails, redhead, stockings

XXXDan

Game time

Categories: amateur, anal, big ass, big cock, crossdressing, game, lingerie, masturbation, orgasm, small cock

KeekAss

REAL GRINDR INTERCOURSE! Gay-For-Pay Married Fellow gets ORAL JOB from Sissy Crossdresser

Categories: amateur, arab, blowjob, brunette, crossdressing, cum in mouth, cumshot, doll, fetish, gay

aShemaleTube

Slim Shemale jerking on webcam

Categories: amateur, big cock, crossdressing, hd, jerking, ladyboy, masturbation, slim, solo, webcam

KeekAss

Analina 26 - Spandex Clyster Rectal - Gargle my Anus

Categories: amateur, anal, anus, ass, big ass, crossdressing, fetish, hd, latex, milk

KeekAss

Spycam compilation

Categories: amateur, bathroom, compilation, crossdressing, hd, hidden cam, homevideo, ladyboy, lingerie, small tits

KeekAss

Slow fantastic dance to taunt BBCs rock rigid and pulsing.

Categories: amateur, ass, big ass, black, crossdressing, fantasy, gay, hd, homevideo, interracial

aShemaleTube

Tina Posing Outdoors 2023

Categories: amateur, big ass, crossdressing, mature, outdoor, posing, sissy, small cock, small tits

aShemaleTube

Yum yum!

Categories: blowjob, crossdressing, dick, femboy, fetish, hd, sissy, sucking

VideoSection

Shemale fucks guy, small tits

Categories: blowjob, cosplay, crossdressing, japanese, small tits, uniform

KeekAss

Bathtub Towel Dotadasp

Categories: amateur, asian, barebacking, bathroom, bbw, beauty, big cock, big tits, black, compilation

JizzBunker

Sissy play outdoors. dildo riding in the forest

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

KeekAss

Anal Invasion Academy Award

Categories: amateur, anal, anal toying, ass, big cock, crossdressing, dildo, fetish, gaping hole, hd

aShemaleTube

nyc pale girl fucked by

Categories: amateur, blonde, blowjob, crossdressing, hd, homevideo, pale

TrannyOne

Pale CD brunette with blue eyes

Categories: blue eyed, brunette, crossdressing, cumshot, masturbation, pale, solo, teen (18+)

TrannyOne

famous protest song Arrabi al Arabe by Mariem Hassan

Categories: anal, anus, arab, ass, big cock, blowjob, crossdressing, dick, gay, hunk

aShemaleTube

Webcam Insertion Banana cream Ass Exstrem Anal Shemales

Categories: amateur, anal, ass, banana, compilation, creampie, crossdressing, insertion, stockings, webcam

aShemaleTube

Sissy sex

Categories: big cock, crossdressing, hd, homevideo, sissy, transsexual

aShemaleTube

🔲Lundi 1 Septembre 2025 💟Chez Moi💕 C'est JuSt Troooop SEXxx! Escorte VaneSsaBiTCHx

Categories: amateur, big cock, bimbo, crossdressing, escort, fetish, french, hd, lingerie, sissy

VideoSection

Tranny, blowage

Categories: blowjob, cosplay, crossdressing, ladyboy, tranny

ShemaleMovie

Gorgeous tranny shoots cum on the mirror

Categories: beauty, behind the scenes, big black cock, big cock, black, close up, college, crossdressing, cum, cumshot

aShemaleTube

SUMM SISSY COCK RUBBING

Categories: crossdressing, dick, hd, masturbation, rubbing, sissy

aShemaleTube

Super Dance - PMV by HoloPMV

Categories: anal, big cock, compilation, crossdressing, cum, cumshot, hd, music, sissy, toys

aShemaleTube

Pink Gurls Go Play

Categories: anal, blonde, crossdressing, dress, hd, high heels, lingerie, mature, satin, solo

aShemaleTube

Coming out as a sissy

Categories: abuse, crossdressing, femboy, hd, sissy, tranny

TrannyOne

sissy crossdresser alex fucks huge dildo

Categories: amateur, anal, anus, ass, bdsm, crossdressing, dildo, extreme, fisting, gay

HClips

Sissies Are Not Athletes

Categories: amateur, anal, asian, assfucking, barebacking, big cock, crossdressing, cum in mouth, dick, hd

aShemaleTube

Tanchou Miko Crossdresser Anal Masturbation Part 1

Categories: amateur, anal, asian, ass, bed sex, cosplay, crazy, crossdressing, cute, dick

aShemaleTube

Sissy and old man

Categories: amateur, anal, crossdressing, group sex, hd, homevideo, mature, old farts, sissy

ShemaleMovie

Crossdresser shemale in pantyhose plays with big cock outdoors

Categories: amateur, anal, anal toying, ass, big ass, big cock, crossdressing, ladyboy, masturbation, monster cock

aShemaleTube

slim shemale mature in high heels shows her body on webcam

Categories: amateur, crossdressing, high heels, homevideo, lingerie, masturbation, mature, pov, slim, small cock

KeekAss

Amateur Crossdresser Ready to Get Fucked by Your Hard Cock

Categories: amateur, bisexual, crossdressing, cum, cumshot, dick, fetish, gay, homevideo, lingerie

aShemaleTube

Red Dragon Dress

Categories: anal, blonde, crossdressing, dress, hd, high heels, mature, pantyhose, solo, wife

KeekAss

Top-Down POINT OF VIEW Rectal

Categories: amateur, anal, anal toying, ass, big clit, crossdressing, dick, ebony, lingerie, masturbation

aShemaleTube

french sissy fucked by a inexperienced egyptian in pari

Categories: amateur, crossdressing, egyptian, french, sissy

aShemaleTube

wet dream handsfree cumshot shemale

Categories: amateur, asian, crossdressing, cumshot, fetish, homevideo, japanese, ladyboy, lingerie, mature

Pornstars: Wet Dream