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Retro Shemale Porn - Free Sex Videos Online

Every retro shemale porn video in one place, quick clips and full movies side by side. Watch online for free or download in full through VipFile, no sign up needed. New retro shemale videos are added daily.

GangBang with Lisa Lawrence - Retro Shemale Interracial Orgy Anal

Jan 03

Retro, Transsex, Anal, Interracial, Orgy, Shemale, Gay, Group, Oral

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👁 0

3-01-2026, 19:41

Lisa Lawrence is a mulatto shemale who takes on a retro interracial gangbang in this orgy clip full of anal, oral, and group tranny action.

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TVS Bound In Rubber - Classic Tranny Bondage and Group Sex

Jan 02

London Enterprises Video, Brit Morgan, Dutchuss Von Stern, Julie Bond, Elizabeth Sexton, Transsexual, Classic, Retro, All Sex

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👁 0

2-01-2026, 04:32

👤 Models: Brit Morgan / Dutchuss Von Stern / Julie Bond (TVTS) / Elizabeth Sexton

📺 Quality: SD

A tranny gets dressed in rubber, bound and gagged by Mistress Dutchuss Von Stern while Julie Bond and Elizabeth Sexton enjoy all the action around her. A classic retro transsexual film.

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Transsexual Prostitutes 5 - Classic TS Streetwalker Hardcore

Dec 28

Devil's Films, Brandy, Leah, Miss T, Marilyn Mansfield, Anthony Gallo, Tim Love, Joe Carbona, Drew Andrews, Steve Aaron

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👁 0

28-12-2025, 01:20

👤 Models: Brandy / Leah / Miss T / Marilyn Mansfield

📺 Quality: SD

Transsexual Prostitutes 5 is a classic shemale movie featuring TS streetwalkers and escorts who give and take cock like only a chick with a dick can.

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Retro Black Shemale and Pool Boy - Vintage Tranny Anal Classic

Dec 26

Shemale, Anal, Black, Retro, Twink, Transexual, Vintage, Classic

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👁 0

26-12-2025, 10:12

A vintage 1970s Black shemale seduces a young blonde pool boy in this retro classic tranny anal clip. Short, sharp and packed with old-school charm.

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She-Male Affairs Classic Retro Hardcore Transsexual Movie

Dec 19

Metropolis, Saki St. Jermaine, Chance Caldwell, Sweet Williams, Lisa Lawrence, Brandy Scott, All Sex, Hardcore, Transsexual, Retro

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👁 0

19-12-2025, 18:07

👤 Models: Saki St. Jermaine / Chance Caldwell / Sweet Williams / Lisa Lawrence (TVTS)

📺 Quality: SD

She-Male Affairs is a classic retro transsexual film featuring Saki St. Jermaine and other voluptuous she-males with surprises between their legs. Hot chicks with dicks in non-stop hardcore gonzo action.

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Blonde Girls With Big Dicks - Classic Retro Shemale Movie

Dec 19

All Sex, Retro, Shemale, Transsexual, Classic

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👁 0

19-12-2025, 00:29

A classic retro shemale compilation featuring blonde trannies with big cocks. This all-sex compilation delivers vintage transsexual action from a golden era.

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Sulka's Wedding - Classic Shemale Retro Feature Film

Dec 17

Caballero Video, Sharon Mitchell, Tigr, Ron Jeremy, Paul Barresi, Craig Roberts, Misty Williams, Jennifer Thomas, Sulka, Mischievous

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👁 0

17-12-2025, 13:35

👤 Models: Sharon Mitchell / Tigr / Ron Jeremy / Paul Barresi

📺 Quality: SD

Sulka's Wedding is a legendary retro transsexual feature film starring Sulka alongside Sharon Mitchell, Ron Jeremy, and a full cast. This classic shemale film includes group sex, she-males, and a bizarre wedding finale.

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I Can't Believe It's A She Male - Classic Retro Shemale Movie

Dec 15

Digital Productions, Jerry Springer, Beautiful Shemale Girl, Oral, Gonzo, All Sex, Classic, Retro, Teen, Shemale

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👁 0

15-12-2025, 12:10

👤 Models: Jerry Springer / Beautiful Shemale Girl

📺 Quality: SD

A classic retro shemale feature with over ninety minutes of teen tranny oral and hardcore action. Hot club girls hide a surprise in their panties in this gonzo shemale anthology.

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Sulka's She Male Encounters - Classic Retro Shemale Movie

Dec 09

Alpha Blue Archives, Sulka, Sylvia, Toni, Lynn, Janie, Hardcore, All Sex, Oral, Shemale

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👁 0

9-12-2025, 12:40

👤 Models: Sulka / Sylvia / Toni / Lynn

📺 Quality: DVDRip

Sulka's She Male Encounters is a rare 1970s classic shemale movie featuring Sulka, Sylvia, Toni, Lynn, and Janie in retro gonzo hardcore action.

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Peepshow Loops 332 Classic Retro Shemale Transsexual Hardcore

Nov 30

Blue Vanities, Loni Sanders, Gypsy Rose, Larry Shipps, Jennifer Thomas, Naughty Niko, Transsexual, Retro, Hardcore, Gonzo

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👁 0

30-11-2025, 04:47

👤 Models: Loni Sanders / Gypsy Rose / Larry Shipps / Jennifer Thomas (Trans)

📺 Quality: DVDRip

Peepshow Loops 332 is a classic retro transsexual hardcore film featuring group sex and shemale fucking action. Watch free or download via VipFile.

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Girls aber bitte mit Schwanz - Retro Shemale Bareback Group

Sep 26

Blowjob, Cumshot, Shemale, Hardcore, Bareback, Transsexual, Retro

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👁 0

26-09-2025, 09:12

👤 Models: Blondy / Lulu Paul / Ronne

📺 Quality: SD

Classic retro shemale movie Girls aber bitte mit Schwanz features Blondy, Lulu Paul and Ronne in bareback hardcore action. Blowjobs and cumshots fill this vintage transsexual feature.

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Girly Boyz - Shemale Vintage Fetish with Nikki Steele and Cast

Jul 25

Fetish, Retro, Blonde, Milf, Big Tits, Vintage

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👁 0

25-07-2025, 17:12

👤 Models: Nikki Steele / Metti Tigore / Olivia Love (TVTS)

📺 Quality: SD

Nikki Steele, Metti Tigore, and Olivia Love (TVTS) star in Girly Boyz, a retro shemale fetish clip full of big tits, blonde curves, and vintage lingerie charm.

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She-Male Sperm Whores 2 - Classic Transsexual Retro Full Movie

Jul 22

All Sex, Classic, Transsexual, Retro

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👁 0

22-07-2025, 02:04

She-Male Sperm Whores 2 is a classic retro transsexual movie with men, women, and shemales all sharing and swallowing loads of cum. A vintage all-sex TS full-length video.

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Mother Nature's Bulging Bellies - Classic Transsexual Group

Apr 17

Ashley, Crystal, Hardcore, Oral, All Sex, Lesbian, Transsexual, Gonzo, Classic, Retro

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👁 0

17-04-2025, 09:16

👤 Models: Sabrina Gelata / Ashley / Crystal / Cumisha Amado

📺 Quality: SD

Mother Nature's Bulging Bellies is a classic retro transsexual group title featuring Sabrina Gelata, Cumisha Amado and a cast of gorgeous T-girls. An all-sex orgy of oral, hardcore, and lesbian action.

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Sexually Dominant Transvestite - Keri Vermont Fetish Dungeon Video

Mar 03

Rick Drexel, All Sex, Fetish, Transvestite, Retro

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👁 0

3-03-2025, 18:03

👤 Models: Rick Drexel / Keri Vermont / John Hawk / Allenina W. (TVTS)

📺 Quality: SD

Dominant transvestite Keri Vermont keeps both male slave Rick Drexel and submissive transvestite Allenina in check inside a real dungeon. Watch this retro fetish clip free on ShemaleTop.

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Malibu She-males - Aja Devore Karen Dior Classic Retro

Feb 21

Rick Rogue, Transsexual, Oral, All Sex, Shemale, Gonzo, Hardcore, Classic, Retro

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👁 10

21-02-2025, 13:57

👤 Models: Rick Rogue / Aja Devore (TVTS) / Karen Dior (TVTS) / Monique De Chambers (TVTS)

🎬 Studio: Metro Interactive

📺 Quality: SD

Aja Devore, Karen Dior, Monique De Chambers and Chloe star in Malibu She-males, a classic retro transsexual hardcore film from Metro Interactive.

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Red Riding She Male Classic Retro Transsexual Feature Film

Feb 17

Pleasure Productions, Rick Rogue, Classic, All Sex, Transsexual, Retro

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👁 7

17-02-2025, 19:59

👤 Models: Rick Rogue / Chloe (TVTS) / Travis Kidd / Robert Sanford

🎬 Studio: Pleasure Productions

📺 Quality: SD

Red Riding She Male is a classic retro shemale feature film from Pleasure Productions directed by Karen Dior. A bedtime story turned wild transsexual all-sex adventure.

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She-Male Seduction - Classic Retro Transsexual All Sex Movie

Dec 21

Sharon Kane, All Sex, Retro, Transsexual, Classic

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👁 6

21-12-2024, 12:54

👤 Models: Amanda / Jason Pride / Karen Dior (TVTS) / Sharon Kane

📺 Quality: SD

She-Male Seduction is a classic retro shemale film featuring Amanda, Karen Dior, Sharon Kane, and more in an unforgettable all-sex transsexual production.

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Viper 7 TV Torment - Shemale Hardcore BDSM Retro Feature

Dec 02

Jennifer, Gonzo, Transsexual, Classic, Retro, Hardcore, Oral, Shemale, All Sex

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👁 3

2-12-2024, 01:28

👤 Models: Jennifer / Reagan / Tony / Allenina (TVTS)

🎬 Studio: L.B.O. Entertainment Group

📺 Quality: SD

Jennifer, Reagan, Tony, and Allenina star in Viper 7 - TV Torment from L.B.O. Entertainment Group. This retro shemale BDSM and oral hardcore feature delivers classic transsexual fetish content.

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