Crossdressing Gay Videos » 20

XXXDan

Ella CD Anal Adventure

Categories: amateur, anal, big cock, crossdressing, hardcore, masturbation, small cock, toys

PornLib

Cum loving crossdresser sucks big black cock dry and clean

Categories: amateur, big black cock, blowjob, cleaner, crossdressing, cum, sucking

JizzBunker

Hot emo crossdresser sucks a cock

Categories: amateur, anal, bdsm, beauty, big ass, big cock, blowjob, cosplay, crossdressing, dick

HDSex

Let's be a plaything of nature

Categories: amateur, anal, ass, assfingering, beauty, big ass, boy, crossdressing, cum, cum swallowing

xHamster

Dirty sissy crossdress slut man whore squirming crazy masturbation orgasm while wearing girlfriend's bra shirt and sweater

Categories: bra, crazy, crossdressing, cumshot, dirty, domination, fetish, girlfriend, handjob, hd

xHamster

fucking boy and looking at me

Categories: barebacking, boy, brazilian, creampie, crossdressing, cumshot, deep throat, felching, handjob, hd

JizzBunker

Me being a sissy slut in a hotel

Categories: amateur, big cock, blowjob, crossdressing, hotel, interracial, sissy, slut

HDSex

Indian guy Anandraj0007 rocks a girl's dress

Categories: amateur, ass, beauty, big ass, big cock, crossdressing, dress, indian, nude, pornstar

JizzBunker

Hot crossdresser dildo toy cockcage

Categories: amateur, crossdressing, dick, dildo, hardcore, masturbation, toys, webcam

JizzBunker

Oh what a nice game with plug rings and e stimulation

Categories: anal, crossdressing, game, masturbation

XXXDan

Femboi cheerleaders fucked bareback in IR anal by black jock

Categories: anal, barebacking, black, crossdressing, fetish, interracial, jock, tattoo, uniform

xHamster

SUCKING COCK BIG GAY JOCKER'S COCK - HOT TRANS

Categories: amateur, anal, asian, beauty, big ass, big cock, black, crossdressing, cum, dick

GayBingo

Enjoying my bra outdoors for a solo moment

Categories: amateur, bra, british, crossdressing, lingerie, outdoor, small cock, solo, uncut, underwear

HDSex

Disney twink gets dominated and used by master Nathan

Categories: amateur, american, bdsm, beauty, big cock, crossdressing, cumshot, domination, facial, lingerie

XXXDan

Fuck me 2

Categories: amateur, crossdressing, fisting, gaping hole, hardcore, russian, skinny, toys

JizzBunker

TOKOROTEN with fucking machine

Categories: big cock, crossdressing, fucking machine, hardcore, masturbation, small cock, toys

xHamster

Slave Adashah locked in a tiny chastity. Fucked in the ass with a large vibrator and masturbated with small vibrators

Categories: amateur, ass, bdsm, boy, crossdressing, dick, hairy, hd, humiliation, masturbation

XXXDan

Hot blue skinned avatar fucked by machine clip 2

Categories: amateur, anal, big ass, crossdressing, dildo, hardcore, huge dildo, orgasm, pov, shemale

HClips

Sissy Crossdresser In 2113 Fetish Bareback Sex With Twink Xxl Dick

Categories: amateur, anal, assfucking, barebacking, brunette, crossdressing, deep throat, dick, fetish, hd

JizzBunker

I like to cum

Categories: amateur, anal, chubby, crossdressing, cum, cumshot, dildo, french, lingerie, masturbation

xHamster

Game Over the Mirror

Categories: amateur, crossdressing, cum, cumshot, fetish, game, jerking, masturbation, mirror, nylon

GayBingo

Doll cum, pantyhose wank, sexy crossdresser

Categories: crossdressing, cum, doll, pantyhose, wanking

TheGay

Mud Dress 67

Categories: amateur, crossdressing, dress, fetish, mud, outdoor, solo

VideoSection

Amateur crossdresser shows off with some cheeky ass wiggles

Categories: amateur, anal, ass, big ass, crossdressing, dildo, extreme, feet, riding, stockings

xHamster

Sporty young guy in his room shows huge anal prolapse and pumps him with a huge pump

Categories: amateur, anal, arab, bdsm, boy, crossdressing, cum, desi, doll, emo

XXXDan

You Fucking Me Makes Me Bilingual

Categories: amateur, anal, asian, compilation, couple, creampie, crossdressing, hardcore, korean, masturbation

TheGay

Exotic Xxx Movie Homosexual Old/young Great Show

Categories: amateur, crossdressing, exotic, latex, old, teen (18+)

GayBingo

Kinkychrisx indulges in solo fun while rocking nylon stockings

Categories: amateur, anal, crossdressing, cum, cumshot, feet, funny, jizz, masturbation, nylon

xHamster

enjoying my pussy

Categories: chubby, crossdressing, fisting, gaping hole, hd, homevideo, sissy, small cock, solo, stockings

XXXDan

Japanese CD giving head

Categories: amateur, asian, blowjob, crossdressing, giving head, japanese

XXXDan

Cute blonde tranny from Seoul in lingerie masturbates her cock on webcam

Categories: anal, bdsm, big ass, big cock, blonde, crossdressing, cute, daddies, dick, interracial

Txxx

Guy with red wig gets his tight asshole smashed by a tall dude

Categories: ass, barebacking, crossdressing, tall, tight

VideoSection

Indian crossdresser Karbi Anglong gets down in the car with some toys

Categories: car, crossdressing, indian, masturbation, tattoo, toys

JizzBunker

Twink TrapyAle plays by sucking a hard cock and then sticking it in his hot tight ass

Categories: anal, ass, big ass, big cock, blowjob, crossdressing, deep throat, dick, lingerie, masturbation

BoyFriendTV

First Session: The Reunion (it's been too long.)

Categories: amateur, bear, big cock, boy, canadian, couple, crossdressing, fetish, homevideo, kinky

xHamster

Pee Black Cock Outdoor Indian Man Fuck

Categories: amateur, anal, ass, beach, bear, black, boy, crossdressing, cum, dick

xHamster

Cosplay Keqing 01

Categories: amateur, asian, cosplay, crossdressing, handjob, hd, solo, stockings, uniform

HDSex

Asian bodybuilders team up with Czech hunter for some intense action

Categories: asian, bodybuilder, bondage, boyfriend, brazilian, chinese, creampie, crossdressing, cumshot, czech

xHamster

Wearing See-through Lingerie Impaling Myself

Categories: african, amateur, anal, ass, crossdressing, daddies, dildo, european, hd, humiliation

xHamster

Eating 10inch plug

Categories: amateur, anal, anal toying, barebacking, big cock, boy, buttplug, close up, crossdressing, dildo

xHamster

Gay Crossdresser slut sissygasm fuck big black dildo

Categories: amateur, anal, big black cock, black, boy, crossdressing, cum, cumshot, dildo, handjob

HDSex

Sassy sissy crossdresser Alberna goes wild with a big dildo

Categories: amateur, anal, crossdressing, dildo, italian, lingerie, masturbation, riding, sissy, solo

XXXDan

I am such a gorgeous crossdressing slut

Categories: amateur, big cock, crossdressing, gorgeous, masturbation, slut, spanish

XXXDan

Crossdresser fucking and sucking large toys

Categories: amateur, big ass, crossdressing, dildo, hardcore, huge dildo, lingerie, riding, solo, sucking

xHamster

Jerking Off In My Favourite Outfit - SlugsOfCumGuy

Categories: amateur, big cock, british, crossdressing, cum, cumshot, daddies, dick, edging, hairy

xHamster

Submissive Sissy Wants to Be Taken

Categories: amateur, barebacking, crossdressing, dick, european, german, hd, masturbation, sissy, solo

GayBingo

Gay dress, getting off, homosexual

Categories: amateur, crossdressing, dress, masturbation

GayBingo

Sexy boys, smooching, sexy femboys

Categories: arab, bdsm, boy, crossdressing, domination, european, humiliation, kissing, latina, party

xHamster

Smoking Anal Play

Categories: amateur, american, anal, barebacking, bisexual, crossdressing, dick, emo, glasses, hd

HotMovs

Jinx Deepthroat And Double Penetration Training

Categories: amateur, crossdressing, deep throat, double penetration, hd, pornstar, solo, toys

Pornstars: Jinx

XXXDan

Big boob crossdresser 40cm dildo fuck

Categories: amateur, anal, crossdressing, dildo, hardcore, huge dildo, masturbation, muscled, toys

xHamster

I tried masturbating

Categories: crossdressing, handjob, hd, homevideo, japanese, masturbation, voyeur

XXXDan

With my pareja haciendo because its very hot

Categories: amateur, anal, big ass, big cock, blowjob, crossdressing, handjob, hardcore, masturbation, pov

GayBingo

Amateur guy in white underwear jerks off and shoots jizz on his leg

Categories: amateur, crossdressing, jizz, masturbation, skinny, solo, spanish, underwear, white

BoyFriendTV

Climax On My High Heels and Nylons with Metal Cock Ring

Categories: american, crossdressing, cum, cumshot, dick, feet, fetish, high heels, homevideo, lingerie

VivaTube

Amateur crossdresser solo play

Categories: amateur, crossdressing, solo

JizzBunker

Two dollars well spent, penis slightly bent

Categories: amateur, big cock, crossdressing, daddies, dick, doll, gloryhole, handjob, high heels, lingerie

PornGem

Crossdresser twunk in wedding dress barebacked by groom

Categories: anal, assfucking, barebacking, blowjob, crossdressing, dress, handjob, stud, wedding

GayBingo

Swimmingpool, assbang, fishnets

Categories: anal, beauty, crossdressing, fishnet, gangbang, hunk, outdoor, stud, tattoo

GayBingo

Inexperienced anal slut forgets the cam is rolling while playing with his butt

Categories: amateur, anal, anal toying, ass, balls, crossdressing, dildo, gaping hole, huge dildo, insertion

GayBingo

Amateur twink, gay asian, young cock

Categories: amateur, asian, barebacking, big cock, blowjob, brutal, chubby, crossdressing, cum, daddies

xHamster

Young boy in white socks

Categories: amateur, anal, ass, big ass, boy, close up, crossdressing, feet, fetish, german

JizzBunker

Transvestite fucks with a 40cm dildo

Categories: amateur, anal, crossdressing, dildo, gaping hole, hardcore, muscled, toys, transvestite

XXXDan

Sissy on camera in hotel

Categories: amateur, anal, asian, crossdressing, hardcore, hotel, masturbation, sissy, toys, webcam

TheGay

Indian Young Gay - Oldest House Slowly Slowly Two Fucking Nearest A Tools Position Sex - Desi New Style Sex With College Students And Gay Boy

Categories: amateur, ass, barebacking, big cock, boy, college, crossdressing, desi, hd, indian

TheGay

Crossdresser Sasha Earth With Fucking Machine

Categories: amateur, brunette, crossdressing, fucking machine, hd, solo, toys, webcam

BoyFriendTV

my long dick loves her high heels

Categories: big cock, crossdressing, cum, cumshot, dick, feet, fetish, high heels, massage, masturbation

GayBingo

Youngster, gay men, gay cum

Categories: amateur, anal, asian, barebacking, bear, big black cock, big cock, blowjob, chubby, crossdressing

xHamster

Happy New Year, welcome 2025!

Categories: amateur, boy, close up, crossdressing, cumshot, hd, homevideo, lingerie, pov, sissy

xHamster

2024.09.21 chastity & catheter & electrostimulation cumshot

Categories: anal, anal toying, crossdressing, cum, cumshot, dildo, fetish, fucking machine, hd, masturbation

JizzBunker

Touristavista crossdresser

Categories: amateur, anal, crossdressing, dildo, hardcore, masturbation, orgasm, pantyhose, tourist, toys

BoyFriendTV

I masturbate my cock until I'm exhausted from so much jerking off - Jovenpoder

Categories: amateur, anal, barebacking, big black cock, big cock, crossdressing, cum swallowing, dick, feet, hunk

xHamster

Naughty Crossdresser gehts anal pussy pounded form sexmachine with thick dildo

Categories: anal, austrian, crossdressing, cum, dildo, extreme, gaping hole, hd, high heels, huge dildo

XXXDan

Show in brown tights

Categories: amateur, big ass, big cock, crossdressing, cumshot, cute, feet, fetish, high heels, lingerie

JizzBunker

Japanese Crossdresser Amane Beach 33

Categories: anal, beach, crossdressing, japanese

JizzBunker

I remember fucking in a red chair

Categories: amateur, anal, big cock, british, couple, cowgirl, crossdressing, cumshot, hardcore, masturbation

JizzBunker

Bisexual anal MILF fucked in threesome with tattooed guy and crossdresser

Categories: 3some, anal, bisexual, blowjob, crossdressing, double penetration, handjob, high heels, maid, pantyhose

GayBingo

Hardcore, boys, amateur gay blowjob

Categories: amateur, anal, barebacking, big cock, blowjob, boy, brutal, crossdressing, deep throat, handjob

xHamster

stepdad's lewd cock looks thick and big

Categories: amateur, asslick, barebacking, bear, beauty, big cock, boy, crossdressing, cumshot, cute

XXXDan

Jerk off in nylon panties in my wifes dress

Categories: amateur, big cock, crossdressing, dress, fetish, jerking, masturbation, nylon, panties, small cock

GayBingo

Epic rubdown with a happy ending featuring Marcus McNeil and Angel Elias

Categories: amateur, anal, barebacking, big cock, blowjob, brutal, crossdressing, daddies, deep throat, handjob

XXXDan

Slut crossdresser, long dildo, good ass, sexy dress

Categories: amateur, anal, ass, big ass, big cock, crossdressing, dildo, dress, hardcore, slut

xHamster

Fucking Machine

Categories: amateur, anal, british, crossdressing, dildo, european, fucking machine, hd, homevideo, sissy

JizzBunker

Me playing with my new toy from Amazon in fishnet stockings

Categories: amateur, anal, big cock, crossdressing, cute, dildo, feet, fetish, fishnet, high heels

xHamster

Ass hole lover fucking my step mom in night

Categories: anal, ass, asslick, barebacking, big black cock, big cock, black, boy, crossdressing, cum

HClips

Crossdresser Kellycd Masturbating Outdoor 8 Min

Categories: amateur, crossdressing, hd, masturbation, outdoor, phone, solo, webcam

PornoXO

Cum on My Crossdressing Mouth

Categories: amateur, blowjob, crossdressing, cum, handjob

VideoSection

Average body, mature

Categories: british, crossdressing, mature, outdoor, small cock, uncut, underwear

XXXDan

I have a dirty assshole for you daddy

Categories: amateur, anal, beauty, big ass, creampie, crossdressing, daddies, dirty, gaping hole, hardcore

VivaTube

Akron Crossdresser Sucks BBC After Fake Craigslist Ad

Categories: amateur, big black cock, blowjob, crossdressing, interracial, sucking

xHamster

Outdoor Scene 2025

Categories: amateur, asian, barebacking, big cock, boy, bukkake, crossdressing, cum, daddies, emo

xHamster

Green haired smoking femboy with makeup

Categories: amateur, american, boy, close up, crossdressing, cute, dick, femboy, fetish, hd

JizzBunker

MERRY SEXY CHRISTMAS

Categories: amateur, anal, big ass, big cock, crossdressing, french, high heels, lingerie, masturbation, striptease

HClips

Sissy Jerk Off In Outdoors Dining Hotel

Categories: amateur, crossdressing, hotel, jerking, outdoor, sissy, solo, webcam

xHamster

Sounding-orgasming with Metal Bead Deep Inside Urethra

Categories: amateur, american, asian, crossdressing, cum, cumshot, dick, extreme, hd, masturbation

VideoSection

Average body, underwear

Categories: british, crossdressing, outdoor, small cock, uncut, underwear

JizzBunker

Shemale takes a huge white cock

Categories: amateur, anal, beauty, big cock, blowjob, crossdressing, cumshot, dick, hardcore, shemale

XXXDan

TWINK IS ALWAYS HUNGRY FOR RAW COCK

Categories: anal, bdsm, big cock, blowjob, bukkake, crossdressing, dick, interracial, twink

XXXDan

Part 2 Candy Takes a Hard Pounding by Black Daddy Kens Huge Uncut BBC and Screams Candy Ass Sissy

Categories: amateur, anal, bdsm, big ass, big black cock, big cock, black, crossdressing, daddies, hardcore

Pornstars: Candy Ass

BoyFriendTV

Sissy crossdresser can’t playing with herself in Tan Tights.

Categories: amateur, british, crossdressing, cumshot, hd, high heels, lingerie, masturbation, nude, nylon

xHamster

Crossdresser playing around in sexy lingery

Categories: amateur, big cock, crossdressing, dutch, european, fetish, hd, high heels, homevideo, masturbation

GayBingo

Punk boys going wild at the glory hole with big cocks

Categories: amateur, anal, asian, barebacking, big black cock, big cock, black, blowjob, boy, bukkake

JizzBunker

Diana in thigh high boots

Categories: boots, crossdressing, lingerie, mature, webcam

JizzBunker

Foot licking stud anal smashed in threesome until cumshot on feet

Categories: 3some, anal, crossdressing, cumshot, feet, fetish, leather, licking, muscled, stud

JizzBunker

TWINK IS ALWAYS HUNGRY FOR RAW COCK

Categories: anal, bdsm, big cock, blowjob, bukkake, crossdressing, dick, twink

XXXDan

A good mom sitting in the pool or in the room

Categories: amateur, anal, big ass, big cock, blowjob, crossdressing, hardcore, lingerie, outdoor, pool

PornoXO

transgender travesti sounding urethral outdoor

Categories: crossdressing, hd, masturbation, outdoor, shemale, solo, stockings, urethra

XXXDan

Riku Shino Real face Sex

Categories: anal, blowjob, crossdressing, handjob, hardcore, shemale

xHamster

Masturbation

Categories: barebacking, bear, boy, bukkake, caught, crossdressing, cum, desi, dick, hd

IcePorn

Gay emo twink masturbating with fleshlight by emosexposed

Categories: crossdressing, emo, fleshlight, masturbation, twink

xHamster

Cuckold see this big and thick cock

Categories: amateur, anal, barebacking, big black cock, big cock, bondage, boy, bukkake, crossdressing, cuckold

XXXDan

ASS AND DICK PLAY WITH CUMSHOT

Categories: amateur, anal, ass, big ass, big cock, crossdressing, cumshot, dick, european, handjob

HDSex

Mature crossdresser Kind Chub sucks cock while the sissy faces humiliation, and the white twink loves BBC

Categories: american, big black cock, black, chubby, crossdressing, cum, daddies, dick, fat, humiliation

XXXDan

David Anderson Close up Gaping

Categories: amateur, anal, british, close up, crossdressing, gaping hole, hardcore, skinny, toys, webcam

GayBingo

Sensual lingerie, massive gay cock in anal action with a sex device

Categories: amateur, anal, anal toying, ass, barebacking, big ass, big cock, crossdressing, cum, cumshot

GayBingo

Mature men indulge in BDSM play with a hung stud raw

Categories: amateur, barebacking, bdsm, big black cock, big cock, black, brutal, crossdressing, cum, cumshot

XXXDan

Introducing Kate - new tranny takes big cock in anal without a condom

Categories: amateur, anal, big cock, blowjob, condom, crossdressing, hardcore, high heels, lingerie, mature

ProPorn

Big-Cock Crossdresser Rebecca Plays with Dildo

Categories: amateur, big cock, crossdressing, dildo, hd, masturbation, solo, webcam

VideoSection

I made my gay friend pound me just how I love it

Categories: amateur, barebacking, big cock, blowjob, bukkake, crossdressing, daddies, friend, hunk, indian

GayBingo

Twink Nick Lewis loves bareback anal and big cock blowjobs

Categories: amateur, anal, barebacking, big cock, blowjob, crossdressing, skinny, twink