Sissy Shemale Videos » 29

aShemaleTube

Trans Girl in Latex stockings and High Dominatrix Heels fucks her Tight Asshole Begging For

Categories: amateur, ass, dominatrix, hd, high heels, homevideo, latex, model, sissy, stockings

TrannyOne

Huge 120 diameter black rubber inflatable anal plug

Categories: amateur, anal, anus, ass, black, crossdressing, ebony, european, extreme, first time

aShemaleTube

Machine fucked by 'The German' dildo, 9 inches long, 7 inch girth & solid

Categories: amateur, anal, australian, crossdressing, dildo, german, hardcore, homevideo, orgasm, sissy

VideoSection

Jessicaxd as a latex doll getting off solo

Categories: amateur, anal, crossdressing, cum, dildo, doll, gloves, jizz, ladyboy, latex

aShemaleTube

Obey, Serve, Repeat - My Sissy Maid’s New Routine POV Now Hiring!!!

Categories: big cock, big tits, crossdressing, domination, fetish, hd, latex, lingerie, maid, pornstar

Pornstars: Viper

ShemaleMovie

Encouraging climax for sissy slut in chastity getting ass fucked - Jessica Bloom

Categories: amateur, anal, assfucking, beauty, cum, dildo, femboy, huge dildo, jizz, orgasm

KeekAss

Latina Smiling Big Cock Transgirl

Categories: amateur, beauty, big cock, boy, brunette, crossdressing, cute, doggystyle, femboy, hd

aShemaleTube

Greasy goth Transsexual covered in oil twerks with toy in her asshole

Categories: ass, big ass, big tits, booty, goth, masturbation, oiled, sissy, solo, spanking

aShemaleTube

Ahegao sissy femboy with dirty feet fucks pumpkin with great sound and huge cumshot

Categories: amateur, asian, crossdressing, cumshot, dirty, feet, femboy, fetish, hd, homevideo

Pornstars: Viper

TrannyOne

More bouncing tiny limp sissy cock

Categories: amateur, crossdressing, dick, gay, hd, sissy, small cock, tiny dick, transvestite

aShemaleTube

Hot trans with a huge cock takes it in the ass

Categories: amateur, ass, big ass, big cock, big tits, creampie, homevideo, huge cock, masturbation, sissy

KeekAss

Trans lady flashes off her cock-squeezing arse and diminutive boobs in black yoga trousers

Categories: ass, babe, bed sex, black, brunette, crossdressing, dick, flashing, gym, hd

aShemaleTube

Shemale takes BBC balls deep

Categories: amateur, anal, balls, barebacking, big ass, big black cock, big cock, fetish, hd, sissy

aShemaleTube

Smoking Hot CD Rides Dildo & Cums

Categories: blonde, crossdressing, cum, cumshot, dildo, hd, lingerie, masturbation, sissy, small tits

aShemaleTube

Asian sissy machine fuck

Categories: anal, asian, crossdressing, hd, masturbation, model, sissy, taiwanese, transsexual

KeekAss

Large Neotori Carrot Fuck Stick Vs Jessica Bloom Extraordinary Assfucking Have Fun

Categories: amateur, anal, anal toying, assfucking, beauty, crossdressing, cum, cum swallowing, cumshot, dildo

TrannyOne

SISSY IN HIGH HEELS HUGE STRAPON IN THE ASS Pegging Extreme Anal Stretching FEMDOM ASS FISTING

Categories: anal, anal fisting, anus, ass, bdsm, bondage, crossdressing, domination, double penetration, extreme

aShemaleTube

pretty trans cutie teases on webcam

Categories: amateur, cute, feet, femboy, homevideo, legs, masturbation, pretty, russian, sissy

aShemaleTube

Vaniana receives cum from daddy

Categories: blowjob, crossdressing, cum, cum in mouth, cumshot, daddies, hd, homevideo, mature, sissy

aShemaleTube

Wanking spanking and fucking my sissy till we both cum together 5th May 2025

Categories: anal, barebacking, cum, hd, masturbation, mature, sissy, spanking, transsexual, wanking

aShemaleTube

Embrace feminisation

Categories: compilation, crossdressing, feminization, hd, sissy

KeekAss

Thin blonde femboy pound and jizz on fuck stick

Categories: amateur, anal, anal toying, blonde, crossdressing, cum, cumshot, cute, dildo, femboy

TrannyOne

Crossdresser Sissy Gina - Black Widow

Categories: anal toying, ass, big black cock, big cock, black, booty, buttplug, crossdressing, dick, ebony

HClips

Appeared Wearing A Japanese Yukata...though Inside Was A Perverted Costume With Sissy Crossdresser

Categories: amateur, anal, asian, assfucking, cosplay, costume, crossdressing, dildo, hd, japanese

aShemaleTube

Pantie show while smoking

Categories: amateur, crossdressing, hd, homevideo, mature, sissy, smoking, solo, stockings, tranny

HDSex

Sissy gets wrecked with an anal toy in hot femboy session

Categories: anal, anal toying, crossdressing, cum, cumshot, femboy, jizz, ladyboy, masturbation, sissy

VideoSection

Dominatrix takes control of a guy in latex trans encounter

Categories: anal, ass, bdsm, big black cock, big cock, blowjob, brutal, creampie, cum, cumshot

KeekAss

Marinatvfem Lingerie Sissy Crossdresser

Categories: amateur, crossdressing, feminization, homevideo, lingerie, mature, sissy

KeekAss

Sissy Masturbating Off Her Yam-Sized Weenie Dressed In Spandex Mittens and a Tutu Sundress

Categories: amateur, ass, big cock, crossdressing, dress, femboy, feminization, fetish, gloves, hd

KeekAss

Rebecca luvs nothing more than a meaty fuck stick up her taut transgirl arse

Categories: amateur, anal, ass, big ass, big cock, crossdressing, dick, dildo, hd, huge cock

HDSex

Fuzzy sock sissy gets pegged by domme Mercer with a bad dragon toy

Categories: anal, gagging, sissy, socks, strap-on, toys

aShemaleTube

Buss yn her mouth

Categories: amateur, big cock, blowjob, crossdressing, cum in mouth, cum swallowing, cumshot, ebony, hd, sissy

ShemaleMovie

Stunning Colombian shemale Missangell_ gets it on with Mrnastyxavier

Categories: amateur, anal, babe, barebacking, beauty, big black cock, big cock, black, colombian, creampie

aShemaleTube

Smanun@ anal cumshow💋

Categories: anal, big ass, cumshot, femboy, hd, masturbation, orgasm, prostate, sissy, small cock

aShemaleTube

Blonde sissy in dress used in missionary and first time rimming ass(close up) - LaylacrossFR

Categories: ass, blonde, close up, condom, crossdressing, cum, doggystyle, dress, first time, french

KeekAss

Crimson Rubberdoll Anal Invasion Drill with Fucktoys Prodding & Farting Out Lashed Splooge to slurp & Gulp

Categories: amateur, anal, anal toying, crossdressing, dildo, farting, fetish, hd, latex, pornstar

Pornstars: Rubberdoll

ShemaleMovie

Sissy in prison Snipgame gets an unexpected poke in the rear

Categories: animation, anime, prison, sissy

aShemaleTube

👑CHiPieBiTCH💜👒 Allez mets Toi à 4 Pattes et Pompe, Ptite Salope à Viol*r en Violet. VaneSsaBiTCHx

Categories: bimbo, blowjob, crossdressing, escort, french, high heels, nylon, sissy, skirt, slut

KeekAss

Sissy Tramp Takes a tub in White Glamour Nymphs Underwear and then Pops in Nylons

Categories: amateur, bathroom, bedroom, bisexual, clothed sex, cute, dick, european, exhibitionist, fetish

HDSex

White sissy with small tits uses dildo for solo play

Categories: anal, anal toying, ass, big ass, corset, dildo, femboy, humiliation, ladyboy, pornstar

aShemaleTube

HA46Insert prostate vibrator, pass by people in a crowded building, and almost be discovered

Categories: anal, asian, big ass, chinese, crossdressing, cumshot, flashing, hd, masturbation, outdoor

KeekAss

Sexy Hot Shemale Jerking Hard On Cam

Categories: amateur, beauty, blonde, brunette, cartoon, cute, homevideo, jerking, kissing, lingerie

aShemaleTube

Daddy Destroys Her Sissy Ass

Categories: amateur, anal, ass, ass to mouth, barebacking, creampie, crossdressing, daddies, hd, homevideo

aShemaleTube

riding

Categories: amateur, anal, crossdressing, femboy, hd, outdoor, riding, sissy, small tits, solo

ShemaleMovie

Getting rear ended by my neighbor Emmainktrans

Categories: amateur, anal, babe, beauty, big black cock, crossdressing, femboy, high heels, ladyboy, lingerie

KeekAss

Greperiodically porking my culo in my uber-cute crimson mini-skirt

Categories: amateur, anal, cute, dick, femboy, hd, masturbation, miniskirt, sissy, solo

ShemaleZ

Sissy Having Fun On Her Knees

Categories: amateur, big ass, funny, hd, knees, sissy, solo, stockings, toys

aShemaleTube

Maid sucks dick

Categories: blonde, blowjob, crossdressing, cum in mouth, cumshot, dick, femboy, fetish, ladyboy, maid

KeekAss

On My Knees For You - Dee Angels

Categories: amateur, anal, beauty, big cock, compilation, crossdressing, cum, cumshot, deep throat, fetish

aShemaleTube

Miss April stretched me out

Categories: amateur, anal, big cock, crossdressing, femboy, hd, homevideo, sissy, small cock

aShemaleTube

Latex tranny has huge cock

Categories: amateur, anal, blonde, british, cumshot, english, escort, huge cock, latex, sissy

aShemaleTube

cock play sucking and gagging

Categories: amateur, big cock, blowjob, dick, femboy, gagging, hd, homevideo, ladyboy, mature

aShemaleTube

san diego hotel flash

Categories: anal, barebacking, big ass, big tits, creampie, crossdressing, femboy, flashing, hotel, outdoor

KeekAss

Bootie Woman Tiffany Ciskiss As Ultra-Kinky Velma Dinkly Nailing Sissy Bootie On 4xl Goblin Fake Penis

Categories: amateur, anal, ass, assfucking, balls, cosplay, crossdressing, dick, extreme, feet

aShemaleTube

Fat sub with her mistress

Categories: abuse, domination, fat, hd, humiliation, mistress, sissy

aShemaleTube

Whipped, Ass Fucked ,and Masturbated

Categories: anal, assfucking, domination, fetish, hd, masturbation, sissy

aShemaleTube

Cd Angie bj new cock yum

Categories: amateur, blowjob, crossdressing, daddies, dick, hd, homevideo, sissy

aShemaleTube

big tits and fat ass glasses tgirl in stockings jerks off big cock on cam

Categories: amateur, ass, big ass, big cock, big tits, fat, glasses, homevideo, jerking, masturbation

aShemaleTube

Niki on back vibing

Categories: barebacking, brunette, crossdressing, cumshot, fucking machine, glasses, hd, homevideo, lingerie, masturbation

KeekAss

Play And Solo Masturbation

Categories: amateur, beauty, brunette, crossdressing, dick, futanari, homevideo, jerking, lingerie, masturbation

TrannyOne

Femboy crossdresser cums in black bodystocking and bra !

Categories: amateur, big cock, black, bodystocking, bra, crossdressing, cum, cumshot, dick, ebony

aShemaleTube

Daniela Santos Makes a Sensual Video and Enjoys Italy a Lot.

Categories: amateur, big cock, big tits, brazilian, italian, milf, sensual, sissy, solo, transsexual

ShemaleMovie

The maid Trixy Sissy Babe cleans the hotel room while getting pounded hard

Categories: anal, babe, blowjob, hotel, maid, sissy

aShemaleTube

Blonde femboy cum

Categories: barebacking, blonde, cum, cumshot, femboy, fucking machine, hd, homevideo, lingerie, sissy

KeekAss

What you looking for? Sissy Victoria India

Categories: brunette, crossdressing, feminization, hd, indian, joi, lingerie, masturbation, music, sissy

TrannyOne

Crossdresser gets an oil penis massage in sexy white nylons

Categories: amateur, crossdressing, cum, cumshot, dick, gay, handjob, happy ending, hd, lingerie

aShemaleTube

Joselynne Crossdresser In Tight Dress And Heels No Panties Do You See My Cock Part One

Categories: amateur, behind the scenes, big ass, crossdressing, dick, dress, escort, fetish, high heels, latina

aShemaleTube

Teasing nylon sissy milf tranny

Categories: amateur, crossdressing, hd, mature, milf, nylon, pantyhose, sissy, stockings, tease

aShemaleTube

cumming twice

Categories: crossdressing, cum, femboy, hd, homevideo, masturbation, sissy, small cock

ShemaleMovie

Amateur shemale enjoys solo play

Categories: amateur, anal, barebacking, brutal, crossdressing, cum, cumshot, homevideo, jizz, ladyboy

aShemaleTube

Lemon Dress

Categories: crossdressing, dress, hd, ladyboy, outdoor, sissy, solo

KeekAss

Ladyboy ravages her fuckhole in the crimson rays

Categories: amateur, anal, anal toying, brunette, cage, crossdressing, cum, cumshot, cute, femboy

aShemaleTube

My Second Video 2020

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

aShemaleTube

BBC Fantasy Vol.2

Categories: barebacking, big black cock, big cock, fantasy, futanari, hd, sissy, sucking, toys

KeekAss

BEHIND-THE-SCENES POINT OF VIEW fucky-fucky with Natty

Categories: amateur, anal, assfucking, behind the scenes, blonde, blowjob, crossdressing, feminization, handjob, hd

HDSex

Transgender milf Jenniferstarts rides a huge dildo like a submissive sissy

Categories: anal, ass, big ass, blowjob, dildo, fishnet, huge dildo, masturbation, milf, sissy

aShemaleTube

blackcock daemon loki breeds sissy trap nun in chastity

Categories: amateur, black, hd, nun, sissy

KeekAss

green fashion she-creature with enormous hard-on popshot in your face

Categories: amateur, big cock, brunette, crossdressing, cumshot, domination, dress, hd, homevideo, huge cock

TrannyOne

Thin Str8 Ginger Sucked and Fucks Thiccc Crossdresser Sissy

Categories: amateur, anal, anus, ass, blowjob, booty, couple, crossdressing, gay, hd

aShemaleTube

Amateur Crossdresser Kellycd2022 Sexy MILF in White Tights

Categories: amateur, blonde, british, crossdressing, cumshot, english, hd, lingerie, masturbation, mature

aShemaleTube

Teasing nylon sissy milf tranny

Categories: amateur, hd, mature, milf, nylon, pantyhose, sissy, tease, tranny

VideoSection

Two trans beauties having a wild time with nylon foot play

Categories: arab, beauty, big cock, crossdressing, cum, cumshot, feet, jizz, kissing, ladyboy

KeekAss

Ladyboy rails fellates and rails my hard-on till she finishes off

Categories: amateur, anal, barebacking, beauty, big cock, blowjob, cowgirl, cum, cumshot, feminization

TrannyOne

Feminized for Girls Night Out (Full Movie)

Categories: amateur, anal, bdsm, beauty, big cock, crossdressing, cum, domination, escort, femboy

aShemaleTube

Sissy CD Fucks Ass with Cucumber

Categories: ass, barebacking, big cock, cucumber, cumshot, femboy, hd, homevideo, lingerie, masturbation

KeekAss

Dual anal invasion intrusion big money-shot

Categories: amateur, anal, anal toying, crossdressing, cum, cumshot, dildo, double penetration, femboy, handjob

aShemaleTube

The sissy story of Autumn Brie

Categories: amateur, anal, big ass, hd, latina, masturbation, sissy, story, toys

aShemaleTube

Your trans girlfriend cucks you (trailer)

Categories: amateur, anal, big ass, blowjob, crossdressing, femboy, girlfriend, hd, interracial, sissy

aShemaleTube

Lime green dress, fishnets and latex boots

Categories: big cock, boots, crossdressing, dress, femboy, fishnet, hd, ladyboy, latex, lingerie

aShemaleTube

slim shemale in pantyhose tugs her big dick on webcam

Categories: amateur, big cock, brunette, femboy, homevideo, jerking, masturbation, pantyhose, sissy, slim

aShemaleTube

Blond skonhed kommer pa en unik made (Samantha sissy world)

Categories: amateur, blonde, dick, femboy, hairless, hd, homevideo, masturbation, shaved, sissy

KeekAss

Outdoor Pop-Shot Of A Rock Hard Slapped Sissy

Categories: amateur, crossdressing, cum, cumshot, high heels, lingerie, masturbation, mature, nylon, outdoor

aShemaleTube

Caged sissy riding dildo

Categories: amateur, anal, blonde, dildo, hd, homevideo, lingerie, riding, sissy, solo

aShemaleTube

Housewife Sveta Lusin. 2025k

Categories: amateur, crossdressing, hd, housewife, mature, sissy, small cock, solo

aShemaleTube

Sissy reams her boipussy with a fuck machine until she spurts

Categories: crossdressing, cum, cumshot, femboy, glasses, hd, sissy, webcam

aShemaleTube

Straight Asian Muscle Hunk Stretches out Black Femboy Ezra_Kyle25

Categories: asian, black, chinese, crossdressing, ebony, femboy, hd, homevideo, hunk, interracial

aShemaleTube

Teen Sissy CD Cock and Balls Worship with Huge Cumshot

Categories: amateur, balls, big cock, crossdressing, cumshot, dick, fetish, hd, homevideo, ladyboy

Pornstars: Viper

aShemaleTube

Sissy NivesH-Fuck Through The Mirror

Categories: amateur, hd, mirror, pantyhose, sissy

aShemaleTube

Sissy twerks

Categories: anal, ass, big ass, crossdressing, dildo, fishnet, french, hd, sissy, solo

aShemaleTube

Minja se igra

Categories: amateur, anal, big cock, crossdressing, femboy, hd, ladyboy, lingerie, pantyhose, sissy

JizzBunker

Crossdreeesr sissy takes her car and goes to the supermarket

Categories: amateur, anal, big cock, car, lingerie, masturbation, mature, nude, outdoor, public

aShemaleTube

She Fucked Me with a Plug in her Ass

Categories: anal, ass, big ass, buttplug, cage, femdom, french, model, pegging, redhead

KeekAss

Ugly and pathetic loser

Categories: amateur, crossdressing, cumshot, fetish, hd, homevideo, jerking, lingerie, masturbation, mature

ShemaleZ

Sissy Maid Deepthroat Training And Vibrator Cum

Categories: cum, deep throat, hd, maid, pov, sissy, solo, stockings, toys, vibrator

KeekAss

Ultra-Kinky Bride - the camera operator got HIGHLY aroused

Categories: amateur, bride, crossdressing, fetish, hd, high heels, kinky, ladyboy, lingerie, masturbation

HClips

Fucking My Sissy Ass Witha Bbc Dildo - Sissy Captions

Categories: amateur, anal, ass, assfucking, big black cock, dildo, hd, mature, redhead, sissy

aShemaleTube

Well feminized asian femboy bj and cum

Categories: amateur, anal, asian, big ass, big tits, cum, cum in mouth, cumshot, femboy, hd

aShemaleTube

sexual evolution 03.

Categories: asian, ebony, futanari, gangbang, ladyboy, latina, sissy

aShemaleTube

Condom cumshot

Categories: ass, chubby, condom, cum swallowing, cumshot, dildo, fingering, glasses, hd, model

KeekAss

Horny Tranny Deepthroat For Hot Tgirl Cock

Categories: amateur, big cock, blowjob, brunette, deep throat, dick, hd, interracial, jerking, kinky

aShemaleTube

full naked slutwalk between trucks

Categories: amateur, crossdressing, domination, femboy, fetish, hd, ladyboy, latex, nude, outdoor

KeekAss

Sissy Oksana railing a monster fake penis

Categories: amateur, anal, anal toying, cage, crossdressing, dick, dildo, lingerie, masturbation, mature

ShemaleMovie

Random guy busts a load on a tranny's glasses and glamorous face in a mini dress

Categories: big tits, blowjob, cum, cumshot, dress, glasses, high heels, jizz, sissy, sucking

aShemaleTube

Holly wanking her cock in the woods

Categories: amateur, crossdressing, cumshot, dick, hd, homevideo, mature, outdoor, sissy, slut

aShemaleTube

Taking a shower in black stockings and orange bikini

Categories: amateur, bikini, black, blonde, crossdressing, femboy, fetish, hd, ladyboy, lingerie

XXXDan

Sissy Johanne gets fucked 2 times

Categories: amateur, anal, big ass, big cock, blonde, blowjob, close up, couple, crossdressing, cute

KeekAss

Femboy Twink Takes Tourist Cock

Categories: anal, blowjob, brunette, crossdressing, dick, femboy, hd, pov, sissy, tourist

aShemaleTube

Upskirt and inserting a huge dildo in her ass

Categories: ass, barebacking, crossdressing, homevideo, huge dildo, lingerie, mature, sissy, stockings, toys

KeekAss

mariaputa molten yellow view bottle

Categories: amateur, anal, anal toying, ass, big ass, bottle, crossdressing, dancing, doggystyle, femboy

TrannyOne

(3dxChat) BDSM room

Categories: 3d, animation, anime, bdsm, bondage, crossdressing, domination, fetish, game, hd