Sissy Shemale Videos » 25

aShemaleTube

She Dominates The Teach

Categories: blowjob, cumshot, hd, pantyhose, sissy

xHamster

Hot Trans Blonde Fucked Doggystyle

Categories: amateur, american, anal, anal toying, big ass, blonde, crossdressing, doggystyle, femboy, feminization

xHamster

German Femboy Huge Anal Gape and Prolapse

Categories: anal, crossdressing, feet, femboy, gaping hole, german, hd, prolapse, redhead, sissy

ShemaleMovie

Shemale prison, cougar

Categories: amateur, american, anal, anal toying, bbw, cage, cougar, crossdressing, cumshot, fishnet

xHamster

crossdressing sissy slut jerking off

Categories: amateur, big cock, big tits, british, crossdressing, cum, cumshot, hd, high heels, jerking

xHamster

Sissy CD in catsuit boots cock worship dirty talk huge cum

Categories: amateur, big cock, boots, catsuit, crossdressing, cum, cumshot, dick, dirty talk, domination

XXXDan

Chastised sissy bimbo slut driving a scooter

Categories: bimbo, mature, sissy, slut

aShemaleTube

gay sissy japanese Sarina In stocking

Categories: asian, crossdressing, gay, hd, japanese, masturbation, sissy, stockings

KeekAss

trans lady plunged by bang machine (Dual POINT OF VIEW) with yam-sized Hankey's Fucktoys XXXCALIBUR

Categories: amateur, anal, anal toying, crossdressing, dildo, fucking machine, hd, huge dildo, ladyboy, lingerie

KeekAss

PLUMPER Witch Halloween She-Male Ask to Idolize Her Thick Manmeat

Categories: amateur, bbw, big cock, chubby, close up, cum, cumshot, cute, fat, halloween

aShemaleTube

TS and boyfriend fucking (Shailo Shana)

Categories: amateur, anal, big cock, blowjob, boyfriend, cumshot, hd, homevideo, lingerie, pov

xHamster

Sissykanisa's Lingerie Collection Ep20 Part2: Red Shiny Stocking with Pantyhose on Top

Categories: amateur, asian, crossdressing, cum, cumshot, cute, handjob, hd, ladyboy, legs

ShemaleMovie

Sissy guidance - Emasculation

Categories: femboy, maid, sissy

xHamster

I'll Always Love You Even Without My Daddy Inside I Wish I Was With You

Categories: amateur, asian, beauty, big cock, cum, cute, daddies, dick, filipina, hd

KeekAss

Masturbating In Lingerie

Categories: amateur, asian, beauty, brunette, femboy, hd, homevideo, italian, latina, lingerie

xHamster

Sissy Accidentally cums while rubbing her clit in the little chastity cage

Categories: amateur, cage, clit, cum, cumshot, hd, ladyboy, masturbation, rubbing, sissy

KeekAss

witness me have fun in all sorts of ways hehe;) money-shot at the end!

Categories: amateur, anal, crossdressing, cumshot, femboy, funny, hd, homevideo, ladyboy, masturbation

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

Kellie cums in panties

Categories: crossdressing, cum, fetish, lingerie, masturbation, panties, sissy, solo, stockings

ShemaleMovie

The domina and the witch in a wild crossdressing adventure

Categories: amateur, anal, babe, beauty, big cock, blowjob, couple, crossdressing, cum, cumshot

xHamster

Tranny girl loves to touch herself

Categories: amateur, american, ass, big cock, cosplay, cute, hd, high heels, lingerie, masturbation

ShemaleMovie

Young sissy shemale beauty dominated in various ways.

Categories: amateur, bdsm, beauty, big cock, compilation, crossdressing, domination, femboy, homevideo, ladyboy

KeekAss

Large Arse Sissy Fuckslut Tag Teamed By Faux-cocks for Torrid Rectal Summer

Categories: amateur, anal, anal toying, ass, assfucking, big ass, cage, crossdressing, cum, curvy

xHamster

Sexy Lingerie, High Heels and Sissy Cumshot

Categories: amateur, ass, beauty, big ass, brazilian, crossdressing, cum, cumshot, cute, feet

xHamster

Closeup Camera - My Uncaged Clitty Shoots Cum Vertically as Ken Fucks My Big Jiggly Asspussy - Candy Ass Sissy

Categories: amateur, anal, big black cock, close up, crossdressing, cum, cumshot, dirty talk, domination, hd

Pornstars: Candy Ass

XXXDan

Sissy Milking Jessica Bloom MULTIPLE Orgasms Riding a Dildo

Categories: amateur, anal, beauty, big ass, big cock, british, cumshot, dildo, hardcore, masturbation

KeekAss

Sissy Glovecum 009 - humungous cumload of a wild leather transgender princess

Categories: amateur, big cock, boots, crossdressing, cumshot, dress, fetish, gloves, hd, latex

aShemaleTube

Fucking my toy and dripping sissy precum

Categories: crossdressing, edging, femdom, hd, sissy, toys

aShemaleTube

Vania Ray Enjoy Small Dildo

Categories: amateur, anal, asian, big ass, big tits, crossdressing, dildo, hd, homevideo, masturbation

aShemaleTube

Nyxi penetrated from behind

Categories: amateur, anal, big cock, big tits, blonde, from behind, hd, sissy

XXXDan

Busty sissy CD gives a stright guy a 48 min sloppy BJ

Categories: amateur, big tits, blonde, blowjob, british, pov, sissy, sloppy

xHamster

Sperm fountain in thong and hold-ups

Categories: amateur, cumshot, fetish, handjob, hd, homevideo, masturbation, mature, sissy, solo

ShemaleMovie

Festive anal pounding featuring juicy sounds

Categories: amateur, anal, anal toying, ass, beauty, big ass, big cock, cum, cumshot, european

ShemaleMovie

Compilation of sexy femboy Jade Madison getting it on with crossdresser Bailey Wilde

Categories: amateur, american, anal, ass, big ass, compilation, crossdressing, cum, femboy, jizz

Pornstars: Sexy Jade

ShemaleZ

Heather Riggs Triple Sissy Birthday Present With Khloe Cox And Krystal Vegas

Categories: amateur, big cock, birthday, gangbang, group sex, pornstar, pov, sissy, tattoo

Pornstars: Krystal Steal

aShemaleTube

Masked sissy stroking and slapping to cumming

Categories: crossdressing, cum, hd, masturbation, sissy, stroking

xHamster

Dominatrix Makes Feminized Roommate Wear Maid Dress

Categories: amateur, american, bdsm, beauty, big cock, crossdressing, cum, domination, dominatrix, dress

KeekAss

Hot shemale amateur self sucking

Categories: amateur, beauty, big cock, bimbo, blowjob, brunette, hd, homevideo, latina, masturbation

KeekAss

When I was ambling nude, a police camper handed by.

Categories: amateur, collar, cop, crossdressing, fetish, hd, japanese, nude, outdoor, piercing

aShemaleTube

My Video 387: Pathan Truck Driver Fucks Mona Khan and Cums 2 Times

Categories: amateur, asian, cum, desi, gay, hd, homevideo, interracial, pakistani, sissy

xHamster

Trans with a Gorgeous Body Dressed up and Horny for Her Dildo

Categories: amateur, anal toying, ass, big ass, big cock, booty, cum, cumshot, dildo, farting

aShemaleTube

Sissy Crossdresser Annette Motel Gangbang Quick Cut

Categories: crossdressing, gangbang, hd, motel, sissy

aShemaleTube

SweetandHot anal & (pre)cumshow🍆💦

Categories: anal, big ass, big cock, cum, femboy, hd, latina, masturbation, milk, orgasm

TrannyOne

Sissy courtyard

Categories: amateur, crossdressing, maid, sissy

xHamster

Do you get horny watching me slide into my silky FFs?

Categories: amateur, hd, latex, masturbation, shy, sissy, solo, stockings, watching

xHamster

Witchy Woman

Categories: amateur, american, crossdressing, cum, dildo, fetish, hd, high heels, juicy, legs

KeekAss

SLIT gobbler. Transgender Princess super-fucking-hot clean-shaven beaver and lil man rod

Categories: amateur, beauty, beaver, big cock, cleaner, couple, crossdressing, cum, dick, fetish

TrannyOne

Milking the sissy & post-cum polishing

Categories: amateur, bdsm, crossdressing, cum, edging, european, gay, handjob, hd, latina

aShemaleTube

SabClip

Categories: amateur, crossdressing, femboy, hd, sissy

ShemaleMovie

Trans woman, transgender

Categories: amateur, anal, ass, babe, beauty, big ass, latina, lingerie, sissy, spanish

xHamster

Ghostface fuck hard a nerdy femboy

Categories: amateur, anal, big ass, big cock, blowjob, crossdressing, domination, femboy, hardcore, hd

xHamster

I'm getting obsessed with chastity play

Categories: amateur, american, clit, crossdressing, dildo, hd, homevideo, sissy, solo

XXXDan

Sissy with a small clit fucked from behind

Categories: anal, bdsm, big clit, clit, from behind, hardcore, sissy

xHamster

Cleaning babe finds two dildos and plays with them with her uli and mouth

Categories: amateur, anal, babe, blowjob, crossdressing, dildo, dress, femboy, fetish, handjob

KeekAss

SANDY CD PLAYS WITH THE PLUMBER AND JERKS HIS MILK

Categories: amateur, anal, blowjob, boy, brunette, crossdressing, cumshot, hd, latina, lingerie

KeekAss

Black Obese sissy XXL backside

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

aShemaleTube

Straight Trinidadian Guy Fucks Latina CD

Categories: amateur, dick, domination, homevideo, latina, sissy, worship

xHamster

Tuck Omanko Stripper Pai-chan

Categories: amateur, asian, crossdressing, femboy, hd, japanese, mature, sissy, small cock, small tits

aShemaleTube

TS angel cums on a mirror

Categories: big cock, cum, cumshot, femboy, hd, homevideo, lingerie, masturbation, mirror, sissy

ShemaleMovie

Aniya the sissy – naughty housewife shemale gets kinky with a dildo

Categories: amateur, anal, beauty, brazilian, crossdressing, dildo, housewife, kinky, ladyboy, maid

xHamster

misr4 - Tranny cums on white lingerie

Categories: crossdressing, cum, cumshot, dick, hd, lingerie, masturbation, mature, panties, polish

KeekAss

Sissy Elvi Lynx Fuck-Fest Machine Analfuck - Preview

Categories: amateur, anal, anal toying, assfucking, blonde, boy, crossdressing, femboy, feminization, fetish

KeekAss

Jizzing All Over My Lovely Undies! - Glorious Sissy Climax!

Categories: amateur, crossdressing, cum, cute, handjob, hd, ladyboy, lingerie, masturbation, orgasm

Pornstars: Anita Blue

TrannyOne

Big Boobs in Pantyhose Fucking a Chubby Hairy Pussy Milf

Categories: amateur, big tits, bisexual, bush, chubby, couple, dick, femdom, hairy, husband

TrannyOne

Breezy sucks off Dolf the hung pizza delivery guy - 360cam

Categories: adorable, amateur, american, big cock, blonde, blowjob, delivery guy, dick, food, hd

aShemaleTube

CD Jamie Jardon corset and denim shorts

Categories: big tits, corset, crossdressing, hd, high heels, jeans, shorts, sissy, slut, tease

xHamster

Sissy Faggot Mini Skirt

Categories: amateur, anal, crossdressing, danish, dildo, extreme, femboy, feminization, hd, lingerie

xHamster

Spandex lover

Categories: amateur, cosplay, crossdressing, european, fetish, handjob, hd, polish, pornstar, sissy

ShemaleMovie

Naughty Brazilian Faphouse with Shemale Dominance and Sissy Submission

Categories: amateur, ass, bdsm, beauty, big ass, bondage, brazilian, domination, femboy, glasses

xHamster

Public Exhibition in Nature Full Version

Categories: amateur, crossdressing, cum, exhibitionist, feminization, french, hd, lingerie, masturbation, nature

JizzBunker

SISSY ANALFISTING - FEMDOM GAPE - DIRTY GARDENBOY

Categories: anal, dirty, femdom, fisting, gaping hole, garden, sissy

xHamster

Do you want to help me have a sissygasm?

Categories: anal, anal toying, big ass, big black cock, black, cum, cumshot, dick, hd, ladyboy

aShemaleTube

Slave bitch used by two CD mistresses

Categories: anal, bitch, crossdressing, domination, hd, mature, mistress, nipples, sissy, slave

KeekAss

a crossdresser in high ram platform footwear and spandex stretch pants is ambling the streets at night

Categories: amateur, black, crossdressing, fetish, hd, high heels, ladyboy, latex, lingerie, outdoor

TrannyOne

Sissy Boy Gets Desperate For His Diaper

Categories: boy, crossdressing, cum, desperate, diaper, dick, gay, hd, masturbation, sissy

aShemaleTube

New Content Elena Andreou Play with Pink High Heels and Anal Orgasm

Categories: amateur, anal, close up, crossdressing, cum, cumshot, dildo, dirty talk, greek, high heels

xHamster

Your slut hurts, but she loves it.. she's going crazy with pleasure with this huge one in her ass!!

Categories: amateur, anal, anal toying, ass, crazy, crossdressing, dildo, femboy, greek, hd

xHamster

I Was Fucked by Two Guys and I Feel Like an Abnormal Female Whore Who Wants Cum Every Day

Categories: amateur, anal, anal toying, big ass, crossdressing, cum, double penetration, fishnet, greek, hd

xHamster

Femboy ts rozebell gets ass full bbc big cock part2

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

xHamster

Kellystar518 is FUCKING GORGEOUS

Categories: amateur, american, anal, beauty, big ass, crossdressing, cum, cumshot, girlfriend, gorgeous

XXXDan

Amazing sexy outdoor slut nudity skirt wearing Sissy Cd Ts

Categories: amazing, anal, mature, nude, outdoor, sissy, skirt, slut, transsexual

aShemaleTube

Hot ts blonde cosplay Harley Quinn in solo

Categories: big cock, blonde, cosplay, cumshot, femboy, hd, homevideo, masturbation, pantyhose, sissy

TrannyOne

Dominatrix Mistress April, transformation into a whore

Categories: 3some, amateur, crossdressing, doctor, dominatrix, femdom, fetish, medical, mistress, nurse

TrannyOne

COCK CRAVING WHORE - SISSY TRAINER

Categories: big cock, blowjob, compilation, cum, cumshot, deep throat, dick, hd, oral, orgasm

aShemaleTube

Sissy Alyssa Lacy Dress

Categories: amateur, chinese, dress, hd, sissy

ShemaleMovie

Sissy sluts, canadian

Categories: amateur, anal, ass, bdsm, big ass, big cock, canadian, compilation, cosplay, crossdressing

xHamster

Little Slut in Heat

Categories: amateur, anal, canadian, crossdressing, dildo, handjob, masturbation, mature, sissy, skinny

aShemaleTube

Naughty Halloween 2024

Categories: cartoon, cum in mouth, futanari, halloween, hd, naughty, redhead, sissy

xHamster

Rigid3d D3d Hard Anal Sex Hot Big Ass Doggy Style Swallow Huge Monster Cock Sweet Tasty Pleasure Rough Sex Cum Thirsty Ass

Categories: amateur, american, anal, asian, ass, big ass, big cock, black, cum, cum swallowing

aShemaleTube

Mexican Crossdresser slut side thong and bareback anal (soy travesti mexicana)

Categories: amateur, anal, ass to mouth, barebacking, crossdressing, femboy, hd, homevideo, ladyboy, latina

aShemaleTube

[no porn] Japanese Sissy wearing Catsuit and tease moving

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

KeekAss

femboy maid drains with bad dragon

Categories: amateur, blonde, dildo, dress, femboy, fetish, hd, high heels, kinky, lingerie

KeekAss

Stocking, Stilettos, Soles and Pecker Fetish Magnificent Transsexual

Categories: amateur, beauty, big cock, brunette, crossdressing, dick, feet, fetish, hd, high heels

aShemaleTube

Asian sissy cum a lot after daddy masturbating her girl cock

Categories: amateur, asian, crossdressing, cum, cumshot, daddies, dick, femboy, futanari, hd

xHamster

same sissy

Categories: anal, anal toying, canadian, game, hd, sissy

aShemaleTube

Pervert sissy femboy night dildo show

Categories: asian, crossdressing, cumshot, dildo, femboy, hd, homevideo, lingerie, masturbation, model

Pornstars: Viper

xHamster

One of the Best Close Ups of Me Coming to Orgasm with My Ass Dripping with Cock

Categories: amateur, anal, ass, close up, crossdressing, cum, dick, greek, hd, lingerie

aShemaleTube

Spider-Girl beauty oral+anal show💋

Categories: anal, ass to mouth, beauty, big ass, big tits, blowjob, cosplay, edging, femboy, halloween

ShemaleMovie

Lovelaska's steamy anal play with a hot dildo

Categories: amateur, anal, anal toying, ass, bdsm, beauty, big ass, dildo, domination, game

XXXDan

Just everyday Cindie, Sissy Slut, Making the Bed, Buttplug, SPH

Categories: amateur, anal, bed sex, big ass, big tits, buttplug, masturbation, sissy, slut, small tits

KeekAss

Yam-Sized Fuck-Stick POINT OF VIEW Suck Off from Mind-Blowing TGirl Pauline

Categories: amateur, blonde, blowjob, british, crossdressing, deep throat, gagging, hd, homevideo, huge cock

TrannyOne

5 women gang bang the cuckold CD bbw strap-on bound sally d'angelo production

Categories: ass, bbw, bdsm, bondage, booty, bound, chained, crossdressing, cuckold, domination

aShemaleTube

Spandexfemboy - Anal Big Dildo Pantyhose Session Compilation

Categories: amateur, anal, anal toying, big ass, compilation, dildo, femboy, fetish, fucking machine, lingerie

xHamster

Pegging in cowgirl position. Amazing Sissy Blaire_18 jumps on Dominatrix Nika's strapon with her anal hole.

Categories: amazing, anal, cowgirl, dominatrix, hd, homevideo, pegging, sissy, strap-on, tattoo

xHamster

I pee like a girl in the women's restroom

Categories: amateur, asian, bathroom, chinese, crossdressing, hd, high heels, pissing, sissy, teen (18+)

xHamster

Crossdresser Sucks Crossdresser's Big Dick

Categories: amateur, american, anal, big cock, blowjob, crossdressing, cum, femboy, feminization, fetish

xHamster

Secretdreamsfuta Hard Anal Sex Hot Big Ass Tasty Fucked Hard Buttocks Thirsty for Pleasure Tasty Ass Gaped Intense Hard Sex

Categories: amateur, american, anal, asian, ass, big ass, big cock, black, compilation, crossdressing

xHamster

Sexy muslim femboy is vry girly

Categories: amateur, asian, cosplay, crossdressing, femboy, ladyboy, lingerie, sissy, slim, solo

KeekAss

39

Categories: amateur, anal, asian, boy, brazilian, creampie, crossdressing, femboy, hd, italian

aShemaleTube

big tits ebony latina shemale toys ass and strokes dick on webcam

Categories: amateur, ass, big ass, big tits, black, dick, ebony, homevideo, latina, masturbation

aShemaleTube

Ghetto tgirls 2 - pmv

Categories: amateur, anal, barebacking, big ass, big cock, big tits, blonde, femboy, gangbang, ghetto

aShemaleTube

Skinny black shemale fucked by white dude

Categories: amateur, black, crossdressing, hd, homevideo, interracial, sissy, skinny, small cock, white

aShemaleTube

MY LOVE 042

Categories: asian, big ass, big tits, chinese, crossdressing, hd, ladyboy, lingerie, masturbation, outdoor

xHamster

Amateur fem sissy , finally starting to discover herself

Categories: amateur, canadian, hd, homevideo, pretty, sissy, slut, transsexual

aShemaleTube

Mexican Crossdresser slut oral sex (soy travesti mexicana)

Categories: amateur, blowjob, crossdressing, femboy, hd, ladyboy, latina, mexican, oral, pov

xHamster

My Hot black boots part 1

Categories: amateur, black, boots, crossdressing, domination, european, fetish, german, hd, homevideo

aShemaleTube

Horny Younger Guy Fucks Trans In Motel Room

Categories: amateur, anal, barebacking, blonde, blowjob, creampie, crossdressing, hd, homevideo, lingerie

KeekAss

Taunting away in her taut black satin sundress

Categories: amateur, black, crossdressing, fetish, hd, high heels, joi, latex, lingerie, masturbation

TrannyOne

Carl bangs cross dresser in audition

Categories: amateur, audition, casting, crossdressing, sissy, transvestite

xHamster

Crossdresser and Woman Putting on Lipliner and Lipstick

Categories: amateur, american, anal, bdsm, beauty, big cock, crossdressing, cum, domination, hd