Sissy Shemale Videos » 14

aShemaleTube

Sensual Bella erotic tease queen💋

Categories: anal, big cock, brazilian, erotic, femboy, hd, latina, masturbation, music, queen

aShemaleTube

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

Categories: amateur, anal, barebacking, crossdressing, femboy, hd, ladyboy, latina, mexican, sissy

KeekAss

Hattabi4ik sizzling gigantic bum femboy costume play rezero self facial cumshot spraying and XXL climax

Categories: amateur, anal fisting, anime, big ass, cosplay, costume, crossdressing, cumshot, facial, femboy

aShemaleTube

Thigh high boots crossdresser sissy dildo fuck, ass worship and cum

Categories: amateur, anal, asian, ass, boots, creampie, crossdressing, cum, cumshot, dildo

Pornstars: Viper

aShemaleTube

Maid maki japanes anal slave

Categories: amateur, anal, asian, big tits, crossdressing, gangbang, japanese, maid, masturbation, sissy

aShemaleTube

Newly Transitioned Tranny Training For Big Dicks

Categories: anal, crossdressing, dick, femboy, fetish, hd, homevideo, ladyboy, sissy, small cock

ShemaleMovie

Gorgeous trans woman enjoys anal play with toys

Categories: amateur, anal, anal toying, big cock, brutal, cage, cum, german, gorgeous, jizz

JizzBunker

SISSY ANALFISTING - FEMDOM GAPE - DIRTY GARDENBOY

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

aShemaleTube

This CLIT is long as a FINGERNAIL @ BeautizOnCam

Categories: amateur, beauty, clit, close up, crossdressing, dick, fingering, hd, sissy, solo

aShemaleTube

Cum On My Cute Sissy Toes

Categories: amateur, cum, cute, homevideo, masturbation, sissy, solo, stockings, toes, webcam

aShemaleTube

Studsfun 1 gay 2 crossdressers

Categories: crossdressing, gay, queen, sissy

aShemaleTube

Trans in Lingerie loves jerking off

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

aShemaleTube

Nude strip in pink bra, panties and latex boots

Categories: big cock, blonde, boots, bra, crossdressing, femboy, hd, ladyboy, latex, lingerie

aShemaleTube

Helga Smoking, Wanking, Cumming In Nice Lingerie - [2025-05-12]

Categories: amateur, big cock, blonde, crossdressing, cum, cumshot, femboy, hd, homevideo, ladyboy

aShemaleTube

SISSY TRAINING PART 1: Ass-to-mouth butt plug Colbietgirl

Categories: ass to mouth, babe, booty, brunette, buttplug, hd, ladyboy, sissy, slut, toys

TrannyOne

Shemale Daniela Chanel starts passionate anal with 69 pose foreplay

Categories: 69, amateur, anal, big ass, big cock, cowgirl, creampie, cumshot, doggystyle, femboy

KeekAss

EP22 Live web cam Rainbow elf stroking off

Categories: amateur, beauty, big cock, crossdressing, cum, cumshot, femboy, huge cock, jerking, ladyboy

aShemaleTube

Amateur Crossdresser Kellycd2022 in Tan Seamless Pantyhose

Categories: amateur, british, crossdressing, cum, cumshot, english, fetish, hd, homevideo, masturbation

KeekAss

Rebecca Farron - 2025.06.27 web cam sesh part trio - fake penis butt sex and analgasm

Categories: amateur, anal, ass, cum, cumshot, dick, dildo, hd, high heels, latex

KeekAss

FROM OUTDOOR TO COUCH!! KINKY HOOKUP OF NYMPHOS!

Categories: anal, beauty, blonde, blowjob, couch, dick, domination, dominatrix, femdom, funny

KeekAss

Giant Pony Fuck-stick fucktoy Deep in my Bootie

Categories: anal, assfucking, big ass, cumshot, dildo, extreme, femboy, feminization, fetish, hd

aShemaleTube

LOVE CUM FOR UGLY SISSY

Categories: amateur, crossdressing, cum, cum in mouth, cumshot, hd, lingerie, masturbation, mature, sissy

aShemaleTube

Black and latina trannies humping intensely

Categories: barebacking, big cock, big tits, black, ebony, femboy, hd, homevideo, humping, latina

aShemaleTube

slim American trans cutie in black stockings masturbates on webcam

Categories: amateur, american, ass, black, cute, homevideo, jerking, masturbation, sissy, slim

aShemaleTube

Mature man fucks young femboy

Categories: amateur, big ass, big cock, crossdressing, cumshot, domination, femboy, hd, homevideo, mature

HDSex

Nikki Jade Taylor, the ultimate she-creature, gets down to "exercise" with a well-endowed babe

Categories: anal, ass, ass to mouth, assfingering, babe, blowjob, fingering, masturbation, orgasm, sissy

aShemaleTube

Dirty Hotel pt 1 vixen in red

Categories: amateur, anal, big tits, crossdressing, dirty, hd, homevideo, hotel, lingerie, mature

ShemaleMovie

Mature Asian crossdresser masturbates outdoors in various languages

Categories: amateur, asian, crossdressing, japanese, masturbation, mature, outdoor, sissy, small cock, small tits

aShemaleTube

Mexican Crossdresser slut oral sex (soy travesti mexicana)

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

KeekAss

Femboy Manmeat sounding compilation

Categories: amateur, compilation, crossdressing, dick, femboy, fetish, hardcore, hd, insertion, lingerie

TrannyOne

Tiny cock cumshot in pantyhose bondage

Categories: amateur, bondage, cum, cumshot, dick, feet, fetish, lingerie, masturbation, orgasm

TrannyOne

Wife insert BBC dildo in my gape sissy ass

Categories: anal, anus, ass, big black cock, big cock, black, booty, couple, crossdressing, dick

aShemaleTube

ASMR with EngSub. Bossy master in black nylons gives a sticky footjob and humiliates. Now it's your

Categories: abuse, anal, anal toying, asian, big tits, black, crossdressing, fetish, footjob, hd

TrannyOne

Trans in Chastity Fucked Raw - Compilation 4

Categories: amateur, american, anal, barebacking, beauty, big ass, big cock, blowjob, compilation, crossdressing

aShemaleTube

Sissy Roxy Jeje baisée par Marc

Categories: anal, creampie, fat, gay, hd, sissy, slave

aShemaleTube

SweetnHot anal cumshow💦

Categories: anal, balls, big cock, cumshot, edging, femboy, hd, latina, masturbation, prostate

aShemaleTube

Beta boy sissy hypno

Categories: barebacking, blonde, blowjob, boy, compilation, domination, hd, interracial, latina, pornstar

Pornstars: Aubrey Kate, Domino

aShemaleTube

[no porn] Humping Exercise with Teddy

Categories: amateur, asian, crossdressing, fetish, hd, humping, model, pantyhose, sissy, small cock

aShemaleTube

A sissy in a skirt and white fishnet stockings fucks dildos and cums

Categories: amateur, asian, big cock, creampie, crossdressing, cum, cumshot, dildo, fetish, fishnet

Pornstars: Viper

TrannyOne

Karen Dior, shemales and CDs

Categories: anal, ass, big cock, blowjob, classic, crossdressing, dick, hardcore, jerking, lingerie

aShemaleTube

A country cross dresser sucks a nice CL dick part 1

Categories: amateur, country, crossdressing, dick, sissy, sucking

aShemaleTube

Toypleasurexxx free ass 5

Categories: amateur, anal, ass, dildo, femboy, fetish, nylon, panties, sissy, slut

aShemaleTube

He fucked me with his Jordan's on

Categories: amateur, anal, big ass, big cock, hd, homevideo, latina, sissy

aShemaleTube

Slutty Annemieke quick stop next to the road

Categories: caught, cute, dick, hd, pissing, public, sissy, slut, street

ShemaleMovie

Latex domina plays with herself and anally penetrates sub

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

KeekAss

Hot Shemale With Creamy BBC

Categories: amateur, beauty, big black cock, big cock, brunette, creampie, ebony, femboy, glasses, homevideo

KeekAss

T-damsel Alexandra Braces is SO damn crazy in this promo vid - noisy squealing and many cum shots

Categories: amateur, anal, big tits, blonde, braces, compilation, crazy, crossdressing, cum, cumshot

aShemaleTube

Sissy femboy in sexy outfit tries on different shoes and masturbates

Categories: amateur, asian, big cock, creampie, crossdressing, femboy, hd, ladyboy, lingerie, masturbation

Pornstars: Viper

aShemaleTube

Old housewife Serge Lusin. 2025vb

Categories: amateur, american, big ass, crossdressing, european, housewife, ladyboy, milf, old, sissy

aShemaleTube

Cdangie pretty lil dick sucker for a new daddy

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

aShemaleTube

Sissy Amber Alexis - JOI Sucking a Dildo with Dominatrix

Categories: amateur, crossdressing, dildo, dirty talk, domination, dominatrix, femboy, fetish, hd, humiliation

Pornstars: Amber Alexis

KeekAss

The Dotadasp Muniky Busy Novinha Gives a Deal in the Caboose of the Liabilities

Categories: amateur, anal fisting, asian, barebacking, big cock, big tits, black, blowjob, compilation, crossdressing

aShemaleTube

Pute Gay

Categories: amateur, anal, cumshot, gay, hd, mature, sissy, toys

KeekAss

Sissy femboy jerking in stockings

Categories: amateur, crossdressing, femboy, fetish, handjob, hd, high heels, homevideo, jerking, legs

aShemaleTube

Annarios Street sissy whore cums for you xhT2rap

Categories: amateur, cum, sissy, slut, street

TrannyOne

Sissy maid boy doing his chores

Categories: boy, crossdressing, gay, hd, maid, sissy, transvestite, uniform

aShemaleTube

Big breast trans babe Jerking and showing off her big tits

Categories: amateur, babe, big ass, big cock, big tits, blonde, creampie, homevideo, jerking, masturbation

aShemaleTube

Princesa Alexa (Doncella Rosa I)

Categories: cute, hd, latina, masturbation, sissy, skirt, small tits, solo, teen (18+), webcam

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

TrannyOne

making love to a boy dressed like my wife

Categories: amateur, anal, asian, beauty, boy, crossdressing, domination, femboy, feminization, hd

aShemaleTube

dildo ride and footjob training

Categories: amateur, anal, crossdressing, dildo, femboy, footjob, hd, sissy

KeekAss

Fabulous She-Creature plays with Herself in Black Stockings

Categories: amateur, beauty, big tits, black, chubby, clit, crossdressing, feet, fetish, homevideo

TrannyOne

Risky outdoor exhibition midnight 19-May-2021

Categories: amateur, ass, big cock, dick, exhibitionist, hd, lingerie, mature, outdoor, pissing

IcePorn

Melissa Masters - Sissy Panties and Dildo Humiliation

Categories: asian, dildo, humiliation, ladyboy, masturbation, panties, sissy, solo

aShemaleTube

Fucking Super Sexy Sissy - Compilation 6

Categories: amateur, american, anal, beauty, big ass, blowjob, compilation, crossdressing, domination, femboy

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

TrannyOne

Nothing Better Than a Deepthroat Blowjob While Smoking

Categories: amateur, beauty, big cock, blowjob, couple, crossdressing, cum, deep throat, facial, fishnet

aShemaleTube

Sexy Blue Eyes Sheboy in Black Lingerie in a Live Cam Show Part 4

Categories: big cock, black, blue eyed, crossdressing, fetish, hd, lingerie, masturbation, sissy, webcam

KeekAss

My Sundress-Up Darling, Rizu-kyun cosplayer get pulverized with bang-out plaything, anime costume play

Categories: amateur, anal, anime, asian, beauty, chinese, cosplay, costume, couple, crossdressing

TrannyOne

Butt Plug Dildo Gives me Multiple Prostate Sissygasms

Categories: amateur, anal, anal toying, anus, ass, big cock, british, buttplug, compilation, crossdressing

aShemaleTube

Housewife Sveta Lusin. 2025m

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

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

XXXDan

Latina sissy uses a big plug

Categories: amateur, anal, beauty, big ass, fetish, hardcore, latina, sissy, solo, spanish

KeekAss

60 electrified shock climax

Categories: amateur, anal, asian, crossdressing, electrified, femboy, hd, ladyboy, sissy, toys

KeekAss

4K. TRANSSEXUAL Katie Fox gets pummeled by TRANSSEXUAL Valkyria dominatrix

Categories: beauty, big cock, cum, cumshot, dominatrix, huge cock, ladyboy, mature, orgasm, pantyhose

aShemaleTube

Asian Sissygasm While Fucked

Categories: amateur, asian, creampie, crossdressing, cumshot, hd, homevideo, lingerie, sissy, stockings

aShemaleTube

Smoking and showing my pantie bulge

Categories: amateur, crossdressing, hd, homevideo, lingerie, mature, panties, sissy, smoking, solo

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

JizzBunker

Sissy crossdresser big white ass ladyboy in purple dress

Categories: amateur, bdsm, beauty, big ass, big cock, big tits, college, compilation, cosplay, crossdressing

HDSex

Seductive sissy crossdresser Rileydix teases and dirty talks while flaunting her amazing booty

Categories: amateur, amazing, american, anal, beauty, booty, crossdressing, dirty talk, lingerie, masturbation

TrannyOne

Crossdresser masturbates and cum in sheer white lingerie

Categories: amateur, crossdressing, cum, danish, european, gay, hd, lingerie, masturbation, nylon

aShemaleTube

Amazing shemales 04

Categories: amazing, big ass, big cock, big tits, compilation, cumshot, hd, homevideo, lingerie, masturbation

aShemaleTube

Party in the USA PMV

Categories: american, anal, barebacking, big cock, blowjob, compilation, cum in mouth, femboy, hd, latina

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

lovely Ukrainian tgirl with tattoos shows her sexy ass

Categories: amateur, ass, big ass, femboy, homevideo, masturbation, sissy, slim, small tits, tattoo

KeekAss

AJ180 Chats Muddy, Groans & Dumps three Immense Cum Shots in "3 She Blows"

Categories: balls, big ass, big black cock, big cock, big tits, black, cum, cumshot, dick, dirty

TrannyOne

Plump horny redheaded Vicki!

Categories: amateur, american, ass, bbw, big tits, booty, chubby, classic, dick, dirty

aShemaleTube

Footjob for your Dick

Categories: dick, feet, femboy, fetish, footjob, hd, sissy, slut, solo, twink

aShemaleTube

cute sissyboy cam!!🌈👄💄👠💖

Categories: big ass, cumshot, cute, femboy, hd, latina, lingerie, masturbation, sissy, solo

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

TrannyOne

At first, I scream so hard from a big dick in my ass and from a strong buzz! A powerful orgy of student guys

Categories: amateur, anal, ass, barebacking, big cock, boy, close up, compilation, crossdressing, cum

JizzBunker

BBW slut pegging a sissy deep

Categories: amateur, anal, bbw, hardcore, pegging, sissy, slut, strap-on

aShemaleTube

Muy Especial

Categories: amateur, crossdressing, hd, homevideo, interracial, ladyboy, mature, sissy, solo

aShemaleTube

Kinky alt femboy kate murano sissy crossdresser gets dominated and fucked with strapon

Categories: anal, blowjob, crossdressing, domination, femboy, hd, kinky, lingerie, sissy, stockings

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

KeekAss

Ac/dc sexual sissy tarts and Domina Tirza

Categories: 3some, amateur, anal, bisexual, blowjob, crossdressing, dick, dildo, domination, dominatrix

KeekAss

Solo Tgirl Whips Her Hard Cock Out

Categories: amateur, beauty, brunette, cute, dick, femboy, girlfriend, hardcore, high heels, homevideo

Pornstars: Natasha Sweet

ShemaleMovie

Sissy in jail loves deepthroating big cocks and that BBC is massive

Categories: animation, anime, big black cock, big cock, deep throat, jail, sissy

HDSex

24-year-old trans doll gives a blow job to a curious straight guy

Categories: amateur, ass, babe, beauty, big ass, big cock, blowjob, creampie, crossdressing, cum

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

KeekAss

Finger-Banging Myself at a Public Park!

Categories: amateur, ass, bbw, big ass, crossdressing, cum, fingering, hd, masturbation, orgasm

TrannyOne

Crossdress Sissy Humiliated

Categories: abuse, bdsm, crossdressing, gay, humiliation, sissy, transvestite

aShemaleTube

Sissy Slut

Categories: anal, blowjob, brunette, cumshot, gay, lingerie, sissy, slut, vintage

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

TrannyOne

Astra cums 9 times! Tgirl cum compilation

Categories: amateur, blowjob, clit, compilation, cum, cum in mouth, cumshot, cute, hd, homevideo

ShemaleZ

Thin Sissy In Leggings Wanks On Cam

Categories: amateur, leggings, sissy, solo, stockings, thin, webcam

KeekAss

Waking up with Insane Pinkish Man Meat Chick Edging before Spunking

Categories: amateur, beauty, booty, crossdressing, cum, cumshot, dick, edging, handjob, hd

TrannyOne

You Want Big Black Cocks

Categories: amateur, big cock, black, dildo, hd, lingerie, sissy, solo

aShemaleTube

Putting on my black stockings with white bra and panties

Categories: big cock, black, blonde, bra, crossdressing, femboy, hd, ladyboy, lingerie, masturbation

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

JizzBunker

Anal Cream and Sissy Orgasms

Categories: amateur, anal, big ass, creampie, crossdressing, cumshot, dildo, gaping hole, gay, masturbation

KeekAss

Hard Core Amateur Asian Tranny

Categories: amateur, anal, asian, beauty, cute, dick, femboy, fetish, hardcore, homevideo