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Kai Bailey Shemale Videos - Free to Watch Online

All shemale porn videos featuring Kai Bailey, clips and full movies together in one spot. Stream Kai Bailey free online or download in full through VipFile, no sign up at all. New Kai Bailey videos added as they drop.

Ploy and Kai - Transsexual Anal Gonzo with Kai Bailey at TSPlayground

Feb 10

Kai Bailey, Ploy B, Transsexual Gonzo Anal

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👁 11

10-02-2026, 01:18

👤 Models: Kai Bailey / Ploy B

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: FullHD 1080p

Kai Bailey and Ploy B team up for a sizzling transsexual gonzo clip from TSPlayground and EvilAngel. These two stunning shemales deliver a hardcore anal performance you can watch free and download via VipFile.

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Sasha De Sade and Kai Bailey - Bareback Gonzo Anal TS

Jan 01

Kai Bailey, Sasha De Sade, Transsexual Gonzo Anal Bareback

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👁 0

1-01-2026, 17:24

👤 Models: Kai Bailey / Sasha De Sade

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: SD

Kai Bailey and Sasha De Sade hook up in an EvilAngel TSPlayground bareback gonzo anal clip that pairs two top shemale performers for a sweaty and satisfying TS session.

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Summer Rayne and Kai Bailey Blonde Bombshell Bareback Cumshot Hardcore

Jan 01

Summer Rayne, Kai Bailey, Small Penis, Piercing, Hardcore, Male On Shemale, Bareback, Rimming, Cumshot, Short Hair

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👁 0

1-01-2026, 05:33

👤 Models: Summer Rayne / Kai Bailey

📺 Quality: FullHD 1080p

Blonde shemale Summer Rayne gets barebacked and facial-blasted by Kai Bailey in this cum-heavy hardcore clip with rimming, blowjob, and tattoo-covered action.

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Kai Bailey and Valentina Mia - Transsexual Anal Gonzo

Dec 30

Kai Bailey, Valentina Mia, Transsexual Gonzo Anal

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👁 0

30-12-2025, 11:04

👤 Models: Kai Bailey / Valentina Mia

🎬 Studio: sFilm

📺 Quality: SD

Kai Bailey and his TS girlfriend Valentina Mia skip the office for a morning of transsexual anal gonzo. Their natural chemistry makes this a standout clip.

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Kai Bailey, Jonelle Brooks, Sasha De Sade EvilAngel TS Anal

Dec 25

Kai Bailey, Jonelle Brooks, Sasha De Sade, Transsexual Gonzo Anal Hardcore

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👁 0

25-12-2025, 17:45

👤 Models: Kai Bailey / Jonelle Brooks / Sasha De Sade

🎬 Studio: EvilAngel

📺 Quality: HD 720p

TS beauties Sasha De Sade and Jonelle Brooks plus stud Kai Bailey deliver a scorching EvilAngel threesome with anal, double blowjobs, and cumshots.

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Kai Bailey and Patty - Transsexual Gonzo Anal from TSPlayground

Dec 14

Kai Bailey, Patty, Transsexual Gonzo Anal

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👁 0

14-12-2025, 00:42

👤 Models: Kai Bailey / Patty

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: SD

Kai Bailey and Patty go hard in this TSPlayground and EvilAngel transsexual gonzo anal clip. Watch free on ShemaleTop and download via VipFile.

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Kai Bailey and Marissa Minx Transsexual Gonzo Anal by TSPlayground

Dec 12

Kai Bailey, Marissa Minx, Transsexual Gonzo Anal

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👁 0

12-12-2025, 03:02

👤 Models: Kai Bailey / Marissa Minx

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: SD

Kai Bailey and Marissa Minx deliver a no-frills transsexual gonzo anal session in this TSPlayground and EvilAngel production. Two top shemale performers going hard.

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The Mostly Pics House S1E4 - Kai Bailey and Vanniall Ebony Cumshot

Dec 10

Vanniall, Kai Bailey, Interracial, Ebony, Cumshot, Shemale, Transex, Anal, Blowjob

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👁 0

10-12-2025, 05:00

👤 Models: Vanniall / Kai Bailey

🎬 Studio: ManyVids

📺 Quality: FullHD 1080p

Kai Bailey and Vanniall star in the season finale of The Mostly Pics House with interracial ebony anal and cumshot action. Download via VipFile.

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Kai Bailey and Laura Sky - Transsexual Gonzo Anal on TSPlayground

Sep 11

Kai Bailey, Transsexual Gonzo Anal

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👁 5

11-09-2025, 14:14

👤 Models: Kai Bailey / Laura Sky

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: HD 720p

Kai Bailey and Laura Sky deliver a hot transsexual gonzo anal video for TSPlayground and EvilAngel that fans have been asking for. Two top shemale performers going at it with zero restraint.

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Kai Bailey and Mickey B - Transsexual Gonzo Anal Clip

Jul 12

Kai Bailey, Transsexual Gonzo Anal

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👁 0

12-07-2025, 20:31

👤 Models: Kai Bailey / Mickey B

📺 Quality: SD

Kai Bailey and Mickey B star in a hot transsexual gonzo anal clip that gets straight to the point with no-nonsense hardcore sex between two great performers.

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Sky T and Kai Bailey - Asian Shemale Bareback Anal Open Ass

Jun 30

Anal, Bareback, Shemale, Asian, Hardcore, Open Ass

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👁 0

30-06-2025, 00:06

👤 Models: Sky T / Kai Bailey

📺 Quality: HD 720p

Sky T and Kai Bailey get into deep Asian shemale bareback anal with open ass stretching in this hardcore video. Watch free online and download via VipFile.

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Transsexual Latinas - Gonzo Anal Hardcore Full Movie

May 09

Gender X, Chanel Santini, Dante Colle, Demii D Best, Kai Bailey, Pierce Paris, Ryder Monroe, Sofia Sanders, Transsexual Gonzo Anal Hardcore

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👁 0

9-05-2025, 23:57

👤 Models: Chanel Santini / Dante Colle / Demii D Best / Kai Bailey

📺 Quality: SD

Transsexual Latinas is a hot gonzo anal hardcore movie featuring Chanel Santini, Kai Bailey, Sofia Sanders, and more top Latina shemale stars. Spicy tranny action from start to finish.

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Bailey Paris & Kai Bailey - Transsexual Gonzo Anal Duo

May 08

Transsexual Gonzo Anal

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👁 0

8-05-2025, 10:07

👤 Models: Bailey Paris / Kai Bailey

📺 Quality: SD

Bailey Paris and Kai Bailey team up for a steamy transsexual gonzo session packed with anal action. Watch these two shemale beauties go all out in this hot duo clip.

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Kai Bailey & Patty - Transsexual Gonzo Anal Shemale Duo

Apr 26

Kai Bailey, Patty, Transsexual Gonzo Anal

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👁 0

26-04-2025, 04:59

👤 Models: Kai Bailey / Patty

📺 Quality: FullHD 1080p

Kai Bailey and Patty come together for a hot transsexual gonzo anal session that delivers non-stop tranny hardcore action. Watch these two TS beauties go all the way.

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Kai Bailey and Tuitui - Transsexual Gonzo Anal Hardcore Clip

Apr 08

Kai Bailey, Transsexual Gonzo Anal

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👁 0

8-04-2025, 13:49

👤 Models: Kai Bailey / Tuitui

📺 Quality: FullHD 1080p

Kai Bailey and Tuitui deliver a hot transsexual gonzo anal hardcore clip full of deep fucking and shemale sex.

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Kai Bailey and Sasha De Sade - EvilAngel Transsexual Gonzo Anal

Feb 23

Kai Bailey, Sasha De Sade, Transsexual Gonzo Anal Hardcore

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👁 4

23-02-2025, 08:43

👤 Models: Kai Bailey / Sasha De Sade

🎬 Studio: EvilAngel

📺 Quality: HD 720p

Slim blonde tgirl Sasha De Sade from EvilAngel gives a slow and luxurious blowjob before mounting Kai Bailey for a deep anal ride that ends with a mouthful of sperm.

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Kai Bailey and Patty - Busty TS Anal Hardcore from EvilAngel

Jan 17

Kai Bailey, Patty, Transsexual, Hardcore, Anal, Gonzo

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👁 10

17-01-2025, 12:19

👤 Models: Kai Bailey / Patty

🎬 Studio: EvilAngel

📺 Quality: HD 720p

Busty TS Patty and Kai Bailey team up for a full EvilAngel gonzo anal and blowjob session. She masturbates while getting her tight ass fucked and finishes with a cock-stroking cumshot on her big tits.

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Lianna Lawson and Kai Bailey - Trans School Girls Bareback

Jan 14

Gender X, Lianna Lawson, Kai Bailey, Blowjob, Asslicking, Cum On Face, Hardcore, Male On Shemale, Bareback

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👁 3

14-01-2025, 12:54

👤 Models: Lianna Lawson / Kai Bailey

🎬 Studio: Gender X

📺 Quality: HD 720p

Lianna Lawson and Kai Bailey play naughty trans school girls in this bareback hardcore clip from Gender X. Watch free on VipFile.

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Kai Bailey and Nonny Anal Gonzo on TSPlayground and EvilAngel

Jan 06

Kai Bailey, Nonny, Gonzo, Anal, Transsexual

Kai Bailey and Nonny Anal Gonzo on TSPlayground and EvilAngel - Shemale Porn Video on ShemaleTop

👁 8

6-01-2025, 17:55

👤 Models: Kai Bailey / Nonny

🎬 Studio: TSPlayground / EvilAngel

📺 Quality: SD

Kai Bailey and Nonny team up for a hot transsexual anal gonzo video produced by TSPlayground and EvilAngel.

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