Sissy Gay Videos Added This Month

xHamster

Anal Relaxation and Gaping for a Boypussy

Categories: amateur, anal, cumshot, dick, dildo, femboy, gaping hole, handjob, hd, masturbation

BoyFriendTV

Got lost in the ruins and fucked bareback in the ass to hot cum .

Categories: amateur, anal, ass, barebacking, big cock, compilation, cum, cum in mouth, daddies, face fucking

VideoSection

Adorable skinny sissy is having fun for some tasty cum

Categories: adorable, amateur, anal, anal toying, beauty, crossdressing, cum, dildo, funny, jizz

BoyFriendTV

Cute Femboy in Skirt Fucks His Ass

Categories: amateur, anal, ass, crossdressing, cumshot, cute, dildo, femboy, hd, masturbation

BoyFriendTV

He Invited Me to an Hotel for a Good Time

Categories: amateur, asian, barebacking, big black cock, big cock, black, blowjob, boy, crossdressing, daddies

BoyFriendTV

Teen CD Tries Out His New Toys Till He Cums

Categories: amateur, anal, anal toying, big ass, crossdressing, cum, cumshot, dildo, hairy, hd

BoyFriendTV

I Held My Piss Until You Said I Could Let Go

Categories: amateur, canadian, close up, college, crossdressing, first time, hardcore, humiliation, lingerie, pissing

BoyFriendTV

Sissy Sub Fag Perry Pupo

Categories: amateur, boy, crossdressing, femboy, hd, sissy, solo

BoyFriendTV

Sissy lingerie

Categories: amateur, hd, high heels, italian, lingerie, sissy, stockings

xHamster

This is a creampie

Categories: anal, ass, barebacking, big black cock, big cock, black, creampie, deep throat, dick, feet

TheGay

Gareth Feminised And Seeded Sissy Loser

Categories: amateur, anal, assfucking, brunette, crossdressing, deep throat, sissy, stockings, throat

BoyFriendTV

Can Dispenser!!

Categories: american, anal toying, bdsm, chubby, dildo, extreme, fat, femboy, gaping hole, hardcore

BoyFriendTV

Leather Crossdresser Sissy trains his hole to the max

Categories: amateur, anal, anal toying, austrian, crossdressing, dildo, gaping hole, leather, lingerie, prolapse

xHamster

Sissy Rozebell - Tranny Love Black Dick Part1

Categories: amateur, black, close up, compilation, dick, hd, homevideo, sissy, tranny

HD21

Sissy Crossdresser Plays with Sex Toy

Categories: amateur, blowjob, crossdressing, cumshot, masturbation, sissy, toys

BoyFriendTV

Sexy bikini love series! Part 1, Part 2

Categories: amateur, asian, couple, crossdressing, fetish, handjob, hd, homevideo, japanese, lingerie

BoyFriendTV

His Royal Majesty with Vicfairy.

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

HDSex

Piss and cum-loving sissy slave indulges in tasty treats

Categories: amateur, anal toying, ass, boots, crossdressing, cum, jizz, nylon, pantyhose, pissing

BoyFriendTV

Good Vibrations!!

Categories: american, anal, ass, chubby, crossdressing, cumshot, femboy, grandpa, high heels, lingerie

HDSex

Bobbie in prissy sissy playtime

Categories: masturbation, sissy, small cock, stockings, toys, webcam

BoyFriendTV

Ai Hot Anime Gay Sex 2025

Categories: amateur, anime, asian, bear, big cock, blowjob, boy, crossdressing, cum, daddies

BoyFriendTV

Daddy Giving Me the Way I Wanted It

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

DrTuber

Tne sissy slut is horny

Categories: amateur, fetish, masturbation, muscled, sissy, slut, webcam

VideoSection

Check out me stretching my holes in sissy gear during a long session

Categories: amateur, anal, anal toying, asian, ass, crossdressing, dildo, german, lingerie, sissy

xHamster

Wanding my Inner Sphincter !!

Categories: american, anal, big cock, bra, chubby, crossdressing, cum, cumshot, fat, masturbation

VideoSection

Cute 18-year-old latina sissy crossdresser embraces her femboy side

Categories: 18 year old, amateur, anal, ass, beauty, big ass, creampie, crossdressing, cute, femboy

BoyFriendTV

shaking ass and twerking in various pairs of underwear, panties, thongs & jockstraps FULL VIDEO

Categories: amateur, asian, ass, british, close up, compilation, crossdressing, femboy, friend, lingerie

BoyFriendTV

Sissy Perry Pupo subfagperry Dildo Fuck 2025

Categories: amateur, crossdressing, dildo, femboy, hd, sissy, solo

GayBingo

Sissy enjoys dildo while girlfriend watches TV

Categories: anal, crossdressing, dildo, feet, girlfriend, masturbation, nylon, sissy, toys

HClips

Bae And I Made Love With Sissy Crossdresser

Categories: amateur, anal, assfucking, big black cock, big cock, black, brunette, crossdressing, deep throat, dick

VipTube

Sissy Crossdresser Cums Hands-Free

Categories: amateur, crossdressing, cum, masturbation, sissy, solo, toys

HClips

Femdom Pov: Sissification Instructions

Categories: amateur, big ass, blonde, booty, fetish, hd, knockers, pov, sissy, solo

HClips

Gay Porn - Thick Cock Blowjob

Categories: amateur, big cock, blowjob, brunette, chubby, crossdressing, curvy, dick, feet, fetish

HDSex

Sissy explores molten beef whistle in this latest installment

Categories: amateur, anal, barebacking, big black cock, big cock, blowjob, crossdressing, cumshot, masturbation, sissy

BoyFriendTV

Give Me Daddy All of U

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

BoyFriendTV

Cone Plug

Categories: american, anal, anal toying, chubby, crossdressing, dildo, extreme, fat, femboy, gaping hole

VideoSection

Step-dad explores with his sissy femboy and finishes in his mouth

Categories: amateur, beauty, black, crossdressing, daddies, femboy, german, lingerie, old, sissy

BoyFriendTV

Two dildos vs plug

Categories: anal, anal toying, ass, big ass, daddies, dildo, greek, hd, masturbation, sissy

ProPorn

Sissy Slut Fucks His Tight Hole with a Big Plug

Categories: amateur, masturbation, sissy, slut, tight, toys, twink

BoyFriendTV

Pink panties and yellow slip!

Categories: amateur, american, boy, crossdressing, cum, cumshot, fetish, handjob, hd, lingerie

BoyFriendTV

crossdressed bottom slave online traning

Categories: amateur, anal, anal toying, boy, casting, college, crossdressing, daddies, desi, fetish

BoyFriendTV

Big Daddy Fucked Me Good

Categories: 3some, amateur, barebacking, black, blowjob, boy, crossdressing, daddies, femboy, indian

xHamster

Sissy crossdresser Anna plays with her ass

Categories: amateur, anal, anal toying, ass, croatian, crossdressing, dildo, gaping hole, hd, lingerie

GayBingo

Every fabulous sissy needs to master the art of sucking cock

Categories: bdsm, crossdressing, dick, master, pov, sissy, sucking

BoyFriendTV

Handsome Employee Fucking Femboy Pantyhouse Lingerie Sexy Yr

Categories: amateur, asian, barebacking, beauty, big ass, big cock, blowjob, crossdressing, femboy, hd

BoyFriendTV

Sissy Rozebell - Tranny Love Black Dick Part2

Categories: amateur, black, compilation, dick, hd, homevideo, sissy, tranny

TheGay

Sleazy Homo Bobbie With Sissy Crossdresser

Categories: anal, assfucking, brunette, crossdressing, deep throat, redhead, sissy, stockings, throat

HDSex

I'm daddy's little sissy toy Angeldiaz17x

Categories: 18 year old, amateur, anal, anal toying, ass, beauty, big ass, crossdressing, daddies, gaping hole

BoyFriendTV

Give Me the Drill Daddy

Categories: amateur, barebacking, big black cock, black, blowjob, boy, crossdressing, daddies, femboy, gangbang

BoyFriendTV

Daddy Never Stop Treating Me Good

Categories: amateur, anal, asian, barebacking, black, blowjob, boy, crossdressing, cum, daddies

BoyFriendTV

RITA PERUTZI'S FEET 2

Categories: amateur, bear, crossdressing, european, feet, fetish, high heels, latina, master, old

BoyFriendTV

Man fucks cute sissy boy in the mouth and tears the hole

Categories: amateur, anal, asslick, barebacking, big cock, blowjob, boy, couple, cute, daddies

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

IcePorn

Crossdressing Sissy Services BBC Daddy

Categories: amateur, big black cock, crossdressing, daddies, interracial, sissy

BoyFriendTV

Rita Perutzi's Feet 6

Categories: amateur, crossdressing, feet, fetish, latina, mature, old, old farts, portuguese, sissy

xHamster

I Couldn't Hold Back Anymore Had to Touch Myself

Categories: amateur, asian, barebacking, big cock, boy, colombian, crossdressing, cum, cumshot, daddies

BoyFriendTV

Deep and Thick Gift for the Glutton

Categories: amateur, american, anal, anal toying, gaping hole, hardcore, latina, lingerie, masturbation, mature

HClips

Sissy Crossdresser In 2113 Fetish Bareback Sex With Twink Xxl Dick

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

BoyFriendTV

Daddy fickt sein femboy und spritz sperma

Categories: amateur, anal, asian, big ass, blowjob, boy, cum, cumshot, daddies, femboy

HDSex

Amateur sissy gets absolutely pounded in the ass

Categories: amateur, anal, ass, barebacking, big black cock, black, crossdressing, cumshot, masturbation, riding

HDSex

You crave a naughty sissy that’ll do wild things to you

Categories: amateur, anal, anal toying, ass, beauty, big ass, creampie, crossdressing, gaping hole, latina

HClips

I Went To A Cruising Park But Was There

Categories: amateur, brunette, crossdressing, cruising, french, hd, nature, outdoor, park, sissy

BoyFriendTV

Giant Fake Tits Crossdresser Jon Scarecrow Driving in Drag

Categories: amateur, car, crossdressing, femboy, hd, lingerie, masturbation, mature, old, outdoor

TheGay

Japanese Crossdresser Pound Unrepining Chap With Belt On

Categories: amateur, anal, asian, assfucking, brunette, crossdressing, deep throat, japanese, oriental, pov

BoyFriendTV

Pink panties, stockings, corset and cum

Categories: amateur, american, big cock, corset, crossdressing, cum, cumshot, daddies, dick, fetish

BoyFriendTV

Fourth of July Dress Up!!

Categories: amateur, american, chubby, crossdressing, dress, fat, femboy, high heels, lingerie, mature

BoyFriendTV

White man whore self whipping punishment

Categories: amateur, anal, ass, bdsm, big cock, bondage, close up, fetish, hd, humiliation

xHamster

Unboxed and Inside Me - Omega from Hankey's Toys

Categories: american, anal, anal toying, ass, cum, cumshot, dick, dildo, extreme, gaping hole

xHamster

Bae and I Made Love

Categories: amateur, anal, barebacking, big black cock, black, boy, crossdressing, cum, cumshot, daddies

xHamster

Getting off on my bed. My facial expression says it all

Categories: amateur, american, anal toying, ass, crossdressing, facial, grandpa, hd, homevideo, lingerie

xHamster

Sissy Rozebell - Tranny Love Black Dick Part2

Categories: amateur, anal, barebacking, big black cock, black, blowjob, couple, crossdressing, cumshot, dick

BoyFriendTV

Rough Raw Fuck: He Made Me His Sissy Bitch

Categories: amateur, ass, big ass, booty, brazilian, hd, muscled, rough, sissy, stud

BoyFriendTV

Pretty Panties!!!

Categories: amateur, american, boy, close up, crossdressing, cum, cumshot, fetish, handjob, hd

xHamster

4th of July Giant fake tits crossdresser in daisy dukes and american flag body suit jacking off

Categories: amateur, american, crossdressing, cum, cumshot, dick, hd, high heels, masturbation, mature

Pornstars: Daisy Dukes

BoyFriendTV

Sissy , the cat's neighbor, came to fuck her holes with the owner

Categories: american, barebacking, big cock, bukkake, cumshot, daddies, femboy, hardcore, neighbor, sissy

BoyFriendTV

Cute Femboy with a Big Ass Fuck Himself with a Dildo and Cum

Categories: amateur, anal, assfucking, big ass, boy, crossdressing, cum, cumshot, cute, dildo

BoyFriendTV

So hot at home

Categories: amateur, anal, crossdressing, cute, femboy, french, homevideo, lingerie, mature, sissy

VideoSection

Sissy shows you how to deepthroat like a pro part two

Categories: amateur, anal, barebacking, big black cock, big cock, black, blowjob, chubby, close up, crossdressing

BoyFriendTV

Climax On My High Heels and Nylons with Metal Cock Ring

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

BoyFriendTV

Slip and panties!

Categories: amateur, american, boy, crossdressing, cum, cumshot, fetish, handjob, hd, lingerie

BoyFriendTV

The Ejaculation Cumpilation Vol.1

Categories: big ass, big cock, compilation, crossdressing, cumshot, hd, high heels, jerking, lingerie, masturbation

TheGay

Stepdaddy Feeding Princess Three

Categories: amateur, blonde, crossdressing, daddies, deep throat, hd, sissy, stockings, throat

BoyFriendTV

Best Twink Cumshot Compilation! - Huge Loads From Big Cock! Sissy Cumshot!

Categories: amateur, big cock, compilation, crossdressing, cum, cumshot, fetish, masturbation, sissy, teen (18+)

xHamster

The slaps his balls in public naked

Categories: amateur, balls, bdsm, big ass, domination, fat, french, hd, humiliation, nude

xHamster

Anal Pleasure

Categories: amateur, anal, ass, crossdressing, dildo, hd, latina, masturbation, sissy, solo

xHamster

Panties jerk off cum on lace thong

Categories: boy, bulge, canadian, crossdressing, cum, dick, hd, jerking, lace, lingerie

BoyFriendTV

She Sucked My BBC Bevor Fuck - Sexy Sissy Rozebell Fucked with Happy End Full

Categories: amateur, anal, barebacking, big black cock, blowjob, crossdressing, cute, femboy, hd, interracial

BoyFriendTV

Anal Training Night

Categories: anal, anal toying, boy, crossdressing, cum, cute, dildo, double penetration, femboy, masturbation

BoyFriendTV

Sissy Sub Fag Perry Pupo Exposure Slut

Categories: amateur, crossdressing, femboy, hd, masturbation, sissy, slut, solo

ProPorn

Sissy Crossdresser Pleasures Daddy

Categories: amateur, blowjob, crossdressing, daddies, handjob, hd, sissy

BoyFriendTV

Daddy in my panties again.

Categories: amateur, american, big cock, crossdressing, cum, cumshot, daddies, fetish, hd, lingerie

BoyFriendTV

The Site Manager Pt2

Categories: african, amateur, anal, barebacking, black, boy, couple, crossdressing, cum, daddies

BoyFriendTV

Cute Femboy Liza Fucks Herself with a Black Dildo and Cums

Categories: amateur, anal, anal toying, big cock, black, boy, crossdressing, cum, cumshot, cute

HClips

Sissy Crossdresser - My Boyfriendd Fucked Me At The Backyard

Categories: african, amateur, anal, assfucking, black, brunette, crossdressing, deep throat, ebony, garden

HDSex

Sissy enjoys an incredibly hot experience with a big black cock in a trio

Categories: amateur, barebacking, big black cock, big cock, blowjob, crossdressing, cumshot, daddies, riding, sissy

BoyFriendTV

Femboy Shows off Caged in Lingerie

Categories: amateur, boy, crossdressing, dildo, femboy, hd, homevideo, lingerie, sissy, solo

BoyFriendTV

Enjioooooyyy!!

Categories: amateur, blowjob, boy, crossdressing, cumshot, daddies, femboy, friend, homevideo, masturbation

JizzBunker

Are you ready to suck some ebony cock you little sissy slut

Categories: big cock, black, blowjob, dick, ebony, interracial, shemale, sissy, slut, sucking

BoyFriendTV

Femboy in Lingerie Bareback Grindr Fucked

Categories: amateur, barebacking, blowjob, creampie, crossdressing, femboy, hd, homevideo, hotel, lingerie

xHamster

Jose Castell Preto Show Her Feet Witch Shoes 1

Categories: amateur, crossdressing, daddies, dick, european, feet, fetish, hd, latina, old

BoyFriendTV

Huge Hollow Butt Plug!!

Categories: amateur, american, anal, buttplug, chubby, crossdressing, dildo, fat, gaping hole, lingerie

xHamster

Muscular Bottom Made Love to Me

Categories: amateur, anal, ass, barebacking, big black cock, big cock, black, blowjob, couple, dick

BoyFriendTV

Analfunner

Categories: american, anal toying, ass, big black cock, crossdressing, dildo, gaping hole, latina, lingerie, sissy

xHamster

wixxen

Categories: amateur, crossdressing, cumshot, fetish, german, hd, high heels, homevideo, lingerie, nylon

BoyFriendTV

A Brief Quickie with My Stepson.

Categories: african, amateur, anal, barebacking, bear, black, blowjob, boy, crossdressing, cum

VideoSection

Sissy femboy enjoys a steamy bath riding a big red dildo

Categories: anal, bathroom, cosplay, dildo, femboy, pov, riding, shower, sissy, soapy

HD21

Big Cock for a Sissy Crossdresser

Categories: amateur, big cock, blowjob, crossdressing, sissy

BoyFriendTV

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

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

HDSex

Sassy sissy crossdresser Alberna goes wild with a big dildo

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

BoyFriendTV

Sissy in disguise

Categories: amateur, hd, high heels, homevideo, italian, lingerie, sissy

BoyFriendTV

Hot compilations, lots of cum from femboy and daddy handsome men!

Categories: amateur, anal, barebacking, beauty, big cock, compilation, cum, cum in mouth, cumshot, daddies

BoyFriendTV

Real Amateur Crossdresser Loves to Suck and Swallow

Categories: amateur, argentinian, big cock, blowjob, couple, crossdressing, cum, cum swallowing, cumshot, facial

VivaTube

Sissy Bareback Group Blowjob

Categories: amateur, barebacking, blowjob, crossdressing, daddies, group sex, sissy

GayBingo

Japanese cross-dresser Sissy Jap Akane enjoys a thrilling session with a prostate toy

Categories: anal, asian, crossdressing, cum, fleshlight, japanese, jizz, massage, orgasm, prostate

BoyFriendTV

Sissy-Slut Takes On 2 Dads

Categories: 3some, amateur, anal, homevideo, sissy, slut

BoyFriendTV

Femboy uses vibrating buttplug and rides dildo in chastity

Categories: anal, ass, boy, buttplug, cum, cumshot, cute, dildo, femboy, hd

xHamster

He Always Want My Ass to Be Fucked

Categories: amateur, anal, ass, barebacking, big black cock, big cock, black, blowjob, boy, couple

xHamster

From brush to house

Categories: amateur, asian, barebacking, big cock, black, blowjob, boy, crossdressing, cum, daddies

BoyFriendTV

On My Back, Where I Belong

Categories: amateur, anal, anal toying, ass, black, british, femboy, fucking machine, masturbation, sissy

BoyFriendTV

Basketball Team gangbang a sissy

Categories: anal, ass, barebacking, big black cock, big cock, black, blowjob, dick, doggystyle, fat