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Bailey Jay Trans Videos - Free to Watch Online

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

Bailey Jay and Bee Armitage Teen Shemale Hardcore

Jan 30

Bailey Jay, Bee Armitage, Teens, Hardcore, Shemale

Bailey Jay and Bee Armitage Teen Shemale Hardcore - Trans Porn Video on TranyVIP

👁 21

30-01-2026, 17:15

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👤 Models: Bailey Jay / Bee Armitage

🎬 Studio: Ts-BaileyJay

📺 Quality: HD 720p

Bailey Jay and Bee Armitage pair up in this teen shemale hardcore clip from Ts-BaileyJay. The two performers bring genuine chemistry and real energy to this collaboration.

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Bailey Jay Hard Rock Feet - Shemale Teen Self Facial

Jan 04

Bailey Jay, Teen, Self Facial, Shemale

Bailey Jay Hard Rock Feet - Shemale Teen Self Facial - Trans Porn Video on TranyVIP

👁 18

4-01-2026, 07:38

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👤 Models: Bailey Jay

🎬 Studio: Ts-BaileyJay

📺 Quality: SD

Bailey Jay from Ts-BaileyJay stars in Hard Rock Feet, a solo shemale clip where the teen trans performer delivers a memorable self-facial cumshot finish. Bailey is one of the genre's most recognizable faces, and this solo performance shows why she became such a popular trans performer early in her career.

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Bailey Jay Uses a New Toy - Shemale Masturbation

Jan 03

Bailey Jay, Masturbation, Shemale

Bailey Jay Uses a New Toy - Shemale Masturbation - Trans Porn Video on TranyVIP

👁 24

3-01-2026, 13:37

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👤 Models: Bailey Jay

📺 Quality: HD 720p

Fan-favorite Bailey Jay gets acquainted with her newest toy in this shemale masturbation clip. Her signature warmth and confidence make even a solo toy session genuinely entertaining.

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Bailey Jay 3 - Glamour Shemale Solo ShemaleYum

Jan 02

Bailey Jay, Tenn, Transsexual, Solo

Bailey Jay 3 - Glamour Shemale Solo ShemaleYum - Trans Porn Video on TranyVIP

👁 10

2-01-2026, 23:05

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👤 Models: Bailey Jay

🎬 Studio: ShemaleYum

📺 Quality: HD 720p

ShemaleYum shoots Bailey Jay in a dramatic glamour-lighting solo that shows off her versatility as a trans model. Her famous cumshot closes a short but visually striking clip that doubles as a portfolio piece for one of trans adult content's most recognized performers.

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Bailey Jay and Kylie Maria We Love To Suck Dick - Shemale BJ

Jan 01

Bailey Jay, Kylie Maria, Cumshot, Shemale, Blowjob, Masturbation, Handjob, Tranny

Bailey Jay and Kylie Maria We Love To Suck Dick - Shemale BJ - Trans Porn Video on TranyVIP

👁 10

1-01-2026, 04:40

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👤 Models: Bailey Jay / Kylie Maria

📺 Quality: HD 720p

Bailey Jay and Kylie Maria team up for We Love To Suck Dick - a shemale blowjob, masturbation, and handjob clip from two transsexual performers who make oral action look effortless. Cumshot and handjob action cap off a short and focused BJ-centered clip. Two shemale performers doing what they do best.

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Bailey Jay and Sarina Valentina - Double Trouble

Dec 30

Shemale, Anal, Hardcore, Line Trap, Blowjob

Bailey Jay and Sarina Valentina - Double Trouble - Trans Porn Video on TranyVIP

👁 5

30-12-2025, 15:31

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👤 Models: Bailey Jay / Sarina Valentina

🎬 Studio: TS-BaileyJay

📺 Quality: HD 720p

Two of the biggest names in shemale content - Bailey Jay and Sarina Valentina - team up in this TS-BaileyJay release. Anal, blowjob, and hardcore action fill this video as both performers bring their best. Double trouble is right.

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Bailey Jay - Welcome to New York Solo Anal Toy Fun

Dec 22

anal orgasm, multiple orgasm, white, 720p, fake tits, shemale, masturbation, anal toys, solo

Bailey Jay - Welcome to New York Solo Anal Toy Fun - Trans Porn Video on TranyVIP

👁 2

22-12-2025, 17:42

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👤 Models: Bailey Jay

📺 Quality: HD 720p

Bailey Jay explores New York in this solo clip packed with masturbation, anal toys, and multiple orgasms. The shemale performer with fake tits works herself through anal toy play and delivers an anal orgasm in 12 minutes. A personal and focused solo from a well-known name.

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Bailey Jay and TS Foxxy in Schoolgirls Hardcore

Dec 21

Bailey Jay, TS Foxxy, Shemale, Hardcore, Uniform, Teen

Bailey Jay and TS Foxxy in Schoolgirls Hardcore - Trans Porn Video on TranyVIP

👁 23

21-12-2025, 13:37

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👤 Models: Bailey Jay / TS Foxxy

🎬 Studio: Ts-BaileyJay

📺 Quality: HD 720p

Bailey Jay and TS Foxxy team up for a naughty schoolgirl-themed hardcore video from Ts-BaileyJay. Two of the biggest names in trans porn go at it in uniform for a wild, high-energy pairing.

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Bailey Jay - Heat of the Moment Anal and Blowjob Solo

Dec 19

Bailey Jay, Masturbation, Anal, Blowjob, Tranny, Shemale, Handjob, Cumshot

Bailey Jay - Heat of the Moment Anal and Blowjob Solo - Trans Porn Video on TranyVIP

👁 19

19-12-2025, 00:35

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👤 Models: Bailey Jay

📺 Quality: HD 720p

Bailey Jay stars in Heat of the Moment, a solo-to-hardcore shemale clip featuring masturbation, blowjob, anal and a cumshot handjob finish. One of the genre's most recognized performers in a direct and energetic format.

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Bailey Jay - Hotel Rendezvous Part 1 Shemale Blowjob

Dec 17

Bailey Jay, Shemale BlowJob

Bailey Jay - Hotel Rendezvous Part 1 Shemale Blowjob - Trans Porn Video on TranyVIP

👁 43

17-12-2025, 18:55

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👤 Models: Bailey Jay

🎬 Studio: TS-BaileyJay

📺 Quality: HD 720p

Bailey Jay sets up a hotel rendezvous scenario in part one of this TS-BaileyJay release. The blowjob-focused clip gives Bailey room to showcase her oral skills in a hotel setting. Classic Bailey Jay content from her own paysite production.

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Bailey Jay Dirty Motel Handy J - Shemale Solo Masturbation

Dec 17

Bailey Jay, Masturbation, Shemale, Solo

Bailey Jay Dirty Motel Handy J - Shemale Solo Masturbation - Trans Porn Video on TranyVIP

👁 24

17-12-2025, 13:29

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👤 Models: Bailey Jay

📺 Quality: HD 720p

Iconic shemale performer Bailey Jay takes a solo turn in this motel-set masturbation clip. Just eight minutes of one of the trans world's most celebrated performers stroking herself in a bare-bones and very genuine setting.

↓ Free download »

Bailey Jay Gonzo Blowjob in My Bed - TS-BaileyJay

Dec 10

Bailey Jay, Shemale, Blowjob

Bailey Jay Gonzo Blowjob in My Bed - TS-BaileyJay - Trans Porn Video on TranyVIP

👁 18

10-12-2025, 23:41

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👤 Models: Bailey Jay

🎬 Studio: TS-BaileyJay

📺 Quality: HD 720p

Bailey Jay delivers a gonzo-style POV blowjob in this intimate bedroom clip from TS-BaileyJay. One of the most recognized shemale performers takes charge and gives an unforgettable oral performance. A must-have clip for fans of Bailey Jay's natural charm and technique.

↓ Free download »

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