Vintage Shemale Videos

TrannyOne

Men want be girls

Categories: amateur, anal, ass, big cock, fetish, lingerie, masturbation, oral, queen, stockings

PornHub

There's Port in Every Girl

Categories: bathroom, behind the scenes, cosplay, gay, ladyboy, party, public, reality, smoking, solo

aShemaleTube

Marquis De Sissy 2002

Categories: crossdressing, sissy, slut, vintage

KeekAss

Blond shemale with pantyhose arches over to take it

Categories: anal, big cock, big tits, blonde, blowjob, cumshot, lingerie, masturbation, mature, stockings

PornHub

This is TGirl Gold!

Categories: amateur, anal, assfucking, classic, hardcore, retro, solo, tgirl, transsexual, vintage

KeekAss

antique crossdressing ep7 pt1

Categories: brunette, crossdressing, domination, hd, lingerie, retro, stockings, vintage

TrannyOne

Mature Anal cougars with young boys full video

Categories: amateur, anal, anus, ass, big cock, big tits, black, dick, ebony, vintage

KeekAss

She-Creature Antique Brief Vid six

Categories: big ass, blonde, blowjob, ebony, handjob, hd, lingerie, masturbation, stockings, sucking

TrannyOne

Vintage, Complicates time, sick patient go to the TS Doctor

Categories: anal, anus, ass, big cock, blowjob, cum, cumshot, dick, ladyboy, latina

xHamster

BELLA - scene #02

Categories: amateur, european, german, hardcore, hd, homevideo, pornstar, retro, vintage

KeekAss

Mature German She-Creature screw dude

Categories: amateur, anal, blonde, blowjob, german, lingerie, mature, milf, tranny, vintage

Txxx

French Vintage TG Orgy

Categories: blowjob, creampie, cumshot, french, group sex, orgy, vintage

aShemaleTube

Shemale and girl hot vintage meeting

Categories: vintage

aShemaleTube

Vintage interracial threeway fuck

Categories: interracial, vintage

TubePornClassic

G spot Girl - Scene 4

Categories: big tits, classic, retro, tgirl, vintage

ShemaleZ

Brazillian Shemale Group Sex

Categories: brazilian, group sex, lingerie, vintage

TrannyOne

Dr. Shemale

Categories: 3some, classic, medical, nurse, pornstar, uniform, vintage

Pornstars: Lilienne Li

TubePornClassic

Retro Vintage BDSM Film - Prima Symphony - Trans Europ Express (1966) (NP)

Categories: bdsm, brunette, classic, french, kinky, old and young, retro, tranny, transsexual, vintage

TubePornClassic

Escort Girl

Categories: classic, escort, retro, tgirl, vintage

aShemaleTube

Lisa Lawrence and a lucky guy (Vintage)

Categories: barebacking, big cock, big tits, blowjob, crossdressing, cumshot, hd, homevideo, interracial, lingerie

MyLust

Stunning busty classic ladyboy loves 69 style position with a man

Categories: 69, big tits, classic, ladyboy, retro, vintage

ShemaleZ

Andrea Nobili In Puts His Big Cock In The Ass Of The Rich Trans

Categories: ass, big cock, big tits, brunette, hd, mature, rich, stockings, transsexual, vintage

ShemaleZ

Mia Isabella Fickt Sklavin.wmv

Categories: bdsm, big ass, hd, pornstar, vintage

Pornstars: Mia Isabella

ShemaleMovie

curvaceous retro russian trans sensually jerksoff

Categories: amateur, masturbation, retro, russian, solo, transsexual, vintage

ShemaleZ

Granny tranny pokeers

Categories: blowjob, compilation, granny, mature, tranny, vintage

TrannyOne

Trained and Dominated TV & TS

Categories: bdsm, bondage, classic, compilation, crossdressing, domination, hd, transsexual, transvestite, vintage

xHamster

MIA MOGLIE E' UN TRANS - (Full Movie - Original Version)

Categories: hardcore, hd, italian, pornstar, retro, transsexual, vintage

TrannyOne

These Boots Are Made for Walking - Sexy crossdress version

Categories: anal, anus, ass, blonde, crossdressing, fetish, hd, high heels, mature, milf

KeekAss

Antique She-Male

Categories: anal, blonde, blowjob, brunette, compilation, gay, handjob, masturbation, retro, vintage

TubePornClassic

Best of Beverly Hills

Categories: big tits, contest, homevideo, lingerie, masturbation, rich, tgirl, vintage, wet, wild

Pornstars: Beverly Hills

TrannyOne

Retro Trans Girl treats her Lover

Categories: anal, anus, ass, bdsm, big cock, classic, couple, dick, domination, transsexual

aShemaleTube

Big tits blonde TS hot

Categories: amateur, big ass, big cock, big tits, blonde, masturbation, solo, transsexual, vintage, webcam

TrannyOne

MD-0165 Young Abing EP3-P

Categories: asian, blowjob, chinese, crossdressing, hd, jerking, masturbation, oral, teen (18+), vintage

TrannyOne

80's hairstyle Cuteypi with a standing cumshot

Categories: classic, cum, cumshot, hd, masturbation, mature, retro, solo, standing, vintage

aShemaleTube

Hot vintage fuck on a table

Categories: table, vintage

aShemaleTube

Vintage mature tranny eats huge cock

Categories: huge cock, mature, pornstar, tranny, vintage

Pornstars: Tina Linaves

TrannyOne

Hottie Vintage Shemale Fucking Bitch Men -SiNNE-

Categories: amateur, anal, ass, big tits, bitch, blowjob, lingerie, oral, retro, titty fuck

aShemaleTube

Hot vintage trio fucking

Categories: vintage

aShemaleTube

VintAgE ShEmAlE Film

Categories: amateur, vintage

ShemaleZ

Transen Xhmroxa

Categories: big tits, blonde, vintage

TubePornClassic

BUSTY HERMAPHRODITE PETEE & BOYFRIEND

Categories: big tits, boyfriend, classic, friend, hermaphrodite, knockers, redhead, retro, strap-on, vintage

aShemaleTube

Hot vintage movie for all comers

Categories: vintage

xHamster

Vintage Vibes: Nailing Retro Looks

Categories: amateur, american, beauty, big ass, big cock, big tits, blonde, compilation, crossdressing, cum

JizzBunker

Cute femboy cums all over and licks it

Categories: amateur, big cock, crossdressing, cum, cumshot, cute, femboy, fetish, licking, masturbation

TubePornClassic

Vizi Trans Di Moana (1990) (720)

Categories: anal, big cock, blonde, brunette, classic, deep throat, moaning, stockings, transsexual, vintage

TubePornClassic

Blonde German Hermaphrodite Fucks Her Maid

Categories: big ass, big tits, blonde, classic, german, hermaphrodite, maid, retro, vintage

TubePornClassic

Shemale Vintage Short Film 3

Categories: anal, brunette, classic, retro, vintage

TrannyOne

Mesmerizing you to go Become the girl thats on her knees SUC

Categories: amateur, blowjob, classic, crossdressing, dick, hd, jerking, masturbation, oral, teen (18+)

TubePornClassic

Tranny Preacher

Categories: blowjob, classic, retro, tranny, vintage

ShemaleMovie

classical vintage trannies

Categories: big cock, blowjob, classic, tranny, vintage

TubePornClassic

Hermaphrodite Sunset Thomas Plays With Ron Jeremy & Susan Nichols

Categories: classic, hermaphrodite, pornstar, retro, vintage

Pornstars: Ron Jeremy, Sunset Thomas, Susan Nichols

aShemaleTube

Busty milf doggied hard by a busty shemale

Categories: amateur, big tits, doggystyle, homevideo, milf, vintage

MyLust

Mesmerizing and lean busty tranny fucks young and submissive man

Categories: big tits, classic, retro, submissive, teen (18+), tranny, vintage

xHamster

Soft and curvy redheaded granny tranny

Categories: beauty, curvy, hd, lingerie, old, pantyhose, redhead, small cock, solo, stockings

ShemaleZ

Sissy dong Humiliation

Categories: amateur, bdsm, domination, fetish, humiliation, sissy, toys, vintage

MyLust

Blonde shemale and brunette girl share one man for threesome

Categories: 3some, blonde, brunette, classic, retro, share, vintage

TrannyOne

sexy Delhi Escorts

Categories: anal, asian, ass, big cock, big tits, blowjob, cum, dick, ebony, fetish

TubePornClassic

Shemale Vintage Short Film 5

Categories: classic, hardcore, retro, vintage

aShemaleTube

Retro threesome with two shemales

Categories: 3some, milf, pornstar, retro, sucking, vintage

Pornstars: Gina Ryder

JizzBunker

Beautiful transexual with big tits!

Categories: amateur, anal, beauty, big tits, blowjob, chubby, handjob, hardcore, interracial, latex

HotMovs

Vintage Beach Movie With Females And One Transgender

Categories: amateur, beach, blonde, stockings, vintage

KeekAss

Wifey Instructs Ideal Slut for her Spouse. Me, A Sissy.

Categories: bimbo, hd, pornstar, retro, sissy, slut, vintage, wife

Pornstars: Anita Blue

KeekAss

Luxurious Antique Transgender Princess pummeled

Categories: anal, blonde, blowjob, cumshot, retro, vintage

KeekAss

She-Male Antique

Categories: 3some, anal, blowjob, hd, interracial, mature, retro, vintage

TubePornClassic

BBW sHEMALE GODESS

Categories: bbw, classic, goddess, plumper, public, retro, vintage

ShemaleZ

Classic Meghan three

Categories: classic, vintage

ShemaleZ

Vintage TS Doctor copulates With ebony Patient

Categories: amateur, blowjob, doctor, ebony, interracial, transsexual, uniform, vintage

TrannyOne

The American Adventures of Surelick Holmes (1971) Complete M

Categories: anal, anus, ass, bdsm, blowjob, classic, couple, crossdressing, dick, hd

aShemaleTube

Fuckind a vintage blonde crossdresser

Categories: anal, blonde, crossdressing, queen, sissy, vintage

JizzBunker

Vintage vampire dominatrix

Categories: amateur, big ass, big cock, chubby, compilation, dominatrix, masturbation, small cock, small tits, smoking

ShemaleZ

Hot Ladyboy Big Cock Threesome

Categories: 3some, big cock, big tits, ladyboy, vintage

ShemaleZ

ladyboy On A Boat - Third World Media

Categories: amateur, blonde, blowjob, boat, ladyboy, outdoor, vintage

TubePornClassic

Hidden Persuasion Vintage She Male VHS Full

Categories: anal, classic, fetish, hidden cam, retro, toys, vintage, webcam

ShemaleZ

Excellent Xxx Clip Tranny Big Tits Hot Only Here

Categories: amateur, big tits, redhead, solo, toys, tranny, vintage

ShemaleZ

Two russian sluts picked up in the street and blowed for cash

Categories: 3some, blowjob, money, pick up, russian, slut, stockings, street, vintage

aShemaleTube

To Spiti Tis Mantam Aloma Greek Porn Vintage

Categories: blonde, blowjob, crossdressing, cumshot, greek, mature, spit, vintage

Txxx

Interesting Italian Vintage

Categories: italian, vintage

xHamster

Vintage Nancy tranny

Categories: anal, blowjob, couple, tranny, vintage

aShemaleTube

Lilienne Li Fucked Deep

Categories: asian, big cock, big tits, blowjob, cumshot, hd, ladyboy, lingerie, stockings, uniform

Pornstars: Lilienne Li

TubePornClassic

Shemale Mom Sleepover

Categories: 3some, anal, big tits, blowjob, classic, handjob, mom, retro, vintage

KeekAss

Fabulous Ladyboy outdoor!

Categories: anal, blowjob, brunette, cumshot, hd, ladyboy, masturbation, milf, outdoor, public

XXXDan

2 horny blondes found each other and fucked so hard

Categories: amateur, bdsm, blonde, college, couple, european, german, hardcore, lingerie, milf

XXXDan

A horny guy gets a trannys dick stuffed into his mouth and sucks it deep - Vintage video

Categories: anal, big cock, blowjob, cumshot, dick, handjob, sucking, vintage

PornoXO

Sex with vintage shemale

Categories: sucking, tranny, vintage

ShemaleMovie

G-BANGS

Categories: big cock, vintage

JizzBunker

ANAL ORGASM Transsexual - vol 09

Categories: anal, big cock, orgasm, transsexual, vintage

PornHub

Orgy with anal trannies and clients sucked off

Categories: amateur, anal, assfucking, black, blowjob, brunette, ebony, orgy, sucking, tranny

xHamster

More Vintage Wife Tina

Categories: amateur, crossdressing, cumshot, hd, lingerie, mature, retro, solo, stockings, vintage

xHamster

Trans with Lady Rox! (Scene 02)

Categories: anal, big cock, blowjob, couple, hd, italian, masturbation, milf, transsexual, vintage

TubePornClassic

Deborah Wells and another hot girl

Categories: brunette, classic, pornstar, retro, tgirl, vintage

Pornstars: Deborah Wells

KeekAss

Transen Report six - Sequence four

Categories: big tits, blowjob, brunette, erotic, european, german, hardcore, romantic, sensual, small tits

TrannyOne

Michael Stefano's Nasty Tales - EPISODE #521

Categories: american, anal, anus, ass, classic, hardcore, pornstar, retro, vintage

Pornstars: Katin

ShemaleZ

Brazilian She Males: Gabrielly - The Cock Princess (2001) With Cristina Bianchini, Carla Fael And Isabelli Branco

Categories: 3some, big cock, big tits, blonde, brazilian, brunette, dick, group sex, latina, outdoor

aShemaleTube

Vintage shemales top guy

Categories: vintage

TrannyOne

I love your Mom

Categories: big cock, classic, dick, european, german, huge cock, jerking, milf, old, vintage

KeekAss

Brown Shemale Threeway

Categories: anal, blowjob, brunette, ebony, hd, interracial, ladyboy, outdoor, rimjob, small tits

xHamster

greek tranny (vintage)

Categories: greek, tranny, vintage

TubePornClassic

Just Girls

Categories: classic, retro, tgirl, vintage

ShemaleZ

ＦＴＭ Bus

Categories: amateur, blowjob, bus, fetish, hd, tattoo, vintage

xHamster

Ol' Skool Black Tranny & White Dude

Categories: black, blowjob, interracial, tranny, vintage, white

ShemaleZ

Luciana Evans sexy blonde argentine aux yeux vert magnifique

Categories: argentinian, ass to mouth, big cock, big tits, blonde, blowjob, latina, vintage

ShemaleZ

sissy Dagmar321 plugged chastity cage whore

Categories: amateur, big ass, cage, hd, mature, sissy, slut, solo, stockings, toys

ShemaleMovie

grannie even going fatter!

Categories: amateur, anal, big tits, granny, lingerie, solo, toys, vintage

KeekAss

India Bewitched T-Model and a str8 guy turns into gay

Categories: anal, blowjob, brunette, cum, cumshot, dick, gay, handjob, masturbation, sucking

XXXDan

Italian Transexual Love Story vol. 04

Categories: anal, big cock, brazilian, hardcore, italian, milf, story, transsexual, vintage

TubePornClassic

trans1

Categories: bondage, classic, japanese, retro, transsexual, vintage

TrannyOne

Old man hairy teen vintage xxx Mirta gets a sensual massage

Categories: classic, erotic, grandpa, hairy, massage, old, old farts, sensual, teen (18+), unshaved

TubePornClassic

vintage threesome: trans, girl, man

Categories: 3some, big cock, brazilian, classic, retro, tranny, transsexual, vintage

TubePornClassic

Bi & Beyond 1 Hermaphrodite Deliah & Jeanna Fine

Categories: bisexual, classic, hermaphrodite, pornstar, retro, vintage

Pornstars: Jeanna Fine

aShemaleTube

Doing laundry can be fun xxx

Categories: amateur, blonde, crossdressing, fetish, funny, homevideo, lingerie, mature, sissy, small cock

aShemaleTube

Lana Luster fucks a guy. Special participation of Crystal Crawford

Categories: big cock, blonde, blowjob, crossdressing, lingerie, masturbation, queen, sissy, stockings, vintage

aShemaleTube

Resourceful vintage tranny with her skilful lover

Categories: tranny, vintage

TrannyOne

Transex Choice

Categories: anal, anus, ass, classic, cum, cumshot, hairy, orgasm, retro, vintage

TrannyOne

Vintage - Limousine

Categories: blowjob, car, classic, limousine, lingerie, oral, underwear, vintage

TrannyOne

Shemale Fetish Threesome

Categories: 3some, american, classic, cum, cumshot, fetish, lingerie, orgy, retro, vintage

TrannyOne

Aunty V's Panty Boy

Categories: bdsm, classic, crossdressing, gay, humiliation, orgy, panties, sissy, teen (18+), transvestite

KeekAss

Guy wants T-Model's manhood!

Categories: amateur, anal, blowjob, brunette, cumshot, dick, ebony, interracial, model, outdoor

TrannyOne

Granny Is A Tranny 01

Categories: anal, ass, big cock, blonde, blowjob, cum, cumshot, dick, extreme, feet

aShemaleTube

Vintage love story for all comers

Categories: story, vintage

TrannyOne

Lady Boy Lovers s1

Categories: anal, anus, asian, ass, blowjob, cum, cumshot, deep throat, facial, hardcore