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Kendall Penny Trans Videos - Free to Watch Online

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

Kendall Penny: A Louboutin Goddess and Her Sissy Maid

Aug 18

blowjob, shemale on male, Domination

Kendall Penny: A Louboutin Goddess and Her Sissy Maid - Trans Porn Video on TranyVIP

👁 35

18-08-2026, 18:49

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👤 Models: Kendall Penny

📺 Quality: UltraHD 4K

Femdom sissy training in luxurious 4K, all heels, worship and total command

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Will Havoc & Kendall Penny - Transsexual Gonzo Anal

Dec 28

Will Havoc, Kendall Penny, Transsexual Gonzo Anal

Will Havoc & Kendall Penny - Transsexual Gonzo Anal - Trans Porn Video on TranyVIP

👁 2

28-12-2025, 19:39

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👤 Models: Will Havoc / Kendall Penny

🎬 Studio: sFilm

📺 Quality: SD

Kendall Penny and Will Havoc pair up for a gonzo transsexual anal clip from sFilm. Kendall's oiled-up body and Will's stamina make for a memorable pairing across this hardcore set. A classically structured trans gonzo clip with a strong cumshot finish.

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Kendall Penny Submits for Pierce Paris - Kink BDSM

Dec 20

Pierce Paris, Kendall Penny, Anal, Flogging, Ball Gag, Blowjob, Shemale, Cumshots, BDSM, Caning

Kendall Penny Submits for Pierce Paris - Kink BDSM - Trans Porn Video on TranyVIP

👁 3

20-12-2025, 21:51

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👤 Models: Pierce Paris / Kendall Penny

🎬 Studio: Kink

📺 Quality: SD

Kink pairs Kendall Penny with Pierce Paris for a Southern Sass BDSM video where Kendall submits to flogging, bondage, caning, and bareback anal. This fiery Southern trans woman pushes back until Pierce Paris breaks through her defences with a thorough and rough fucking. A full Kink production with real BDSM content.

↓ Free download »

Kendall Penny TGirl Bisexual Shemale on Male

Dec 19

Kendall Penny, bisexual threesome, Shemale on male

Kendall Penny TGirl Bisexual Shemale on Male - Trans Porn Video on TranyVIP

👁 3

19-12-2025, 19:59

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👤 Models: Kendall Penny

📺 Quality: FullHD 1080p

Kendall Penny stars in this bisexual shemale-on-male clip under the TgirlOneGuy banner, putting a submissive male through his paces across state lines. Dominant trans performer, obedient male partner.

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Kendall Penny - Cum Eating Instructions Trans Solo Domination

Nov 20

Kendall Penny, Average Dick, Solo, Thong, Male to Female, Masturbation, Medium Ass, Medium Tits, Cum Shot, Athletic

Kendall Penny - Cum Eating Instructions Trans Solo Domination - Trans Porn Video on TranyVIP

👁 3

20-11-2025, 14:43

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👤 Models: Kendall Penny

🎬 Studio: TransAngels

📺 Quality: FullHD 1080p

TransAngels' Kendall Penny delivers a solo domination video where she instructs the viewer through a cum eating instructions format. Athletic trans performer, pink lingerie, and a self-facial payoff. Genuinely captivating shemale solo content.

↓ Free download »

Kendall Penny - Bareback Anal Hardcore from TGirls

Oct 14

Kendall Penny, Shemale, Anal, Hardcore, Bareback

Kendall Penny - Bareback Anal Hardcore from TGirls - Trans Porn Video on TranyVIP

👁 3

14-10-2025, 00:14

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👤 Models: Kendall Penny

🎬 Studio: TGirls

📺 Quality: HD 720p

TGirls presents Kendall Penny in a bareback shemale anal and hardcore clip running 23 minutes, with no-condom anal action and a confident trans performance.

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Kendall Penny Creampied Short Stack - Shemale Blowjob

Aug 23

Kendall Penny Creampied Short Stack - Shemale Blowjob - Trans Porn Video on TranyVIP

👁 6

23-08-2025, 22:15

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👤 Models: Kendall Penny

📺 Quality: 2K UHD

Kendall Penny takes a devoted partner through blowjob worship and shemale-on-male action before delivering a creampie and making him cum on her cock. She's firmly in charge throughout this dominant shemale clip. A confident performance from a trans performer who knows how to run a scene.

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Michael Del Ray and Kendall Penny Transsexual Hardcore

Jul 30

Michael Del Ray, Kendall Penny, Transsexual Gonzo Hardcore

Michael Del Ray and Kendall Penny Transsexual Hardcore - Trans Porn Video on TranyVIP

👁 6

30-07-2025, 21:00

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👤 Models: Michael Del Ray / Kendall Penny

🎬 Studio: Transsensual

📺 Quality: HD 720p

Kendall Penny catches her husband cheating and invites delivery man Michael Del Ray in for revenge sex in this Transsensual gonzo transsexual hardcore video. She deepthroats his massive cock before riding him hard in this role-driven shemale clip. A well-acted and well-shot Transsensual release.

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Kendall Penny - TgirlOneGuy Shemale on Male Interracial

Jun 29

Kendall Penny, Interracial

Kendall Penny - TgirlOneGuy Shemale on Male Interracial - Trans Porn Video on TranyVIP

👁 13

29-06-2025, 22:31

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👤 Models: Kendall Penny

📺 Quality: FullHD 1080p

Kendall Penny tops a black male partner in this TgirlOneGuy interracial shemale on male clip. The video covers an interracial trans topping scenario that is the central selling point of the TgirlOneGuy format.

↓ Free download »

Kendall Penny - Shemale Solo Strokers Exclusive

Feb 20

Kendall Penny, Shemale, Solo

Kendall Penny - Shemale Solo Strokers Exclusive - Trans Porn Video on TranyVIP

👁 7

20-02-2025, 20:18

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👤 Models: Kendall Penny

📺 Quality: FullHD 1080p

Kendall Penny takes solo center stage in this Shemale Strokers and Transational Fantasies release, showing off her body and stroking through an extended solo shemale performance.

↓ Free download »

Kendall Penny TGirls Solo Shemale Showcase

Dec 15

Kendall Penny, Shemale, Solo

Kendall Penny TGirls Solo Shemale Showcase - Trans Porn Video on TranyVIP

👁 3

15-12-2024, 04:01

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👤 Models: Kendall Penny

🎬 Studio: TGirls

📺 Quality: HD 720p

Kendall Penny delivers a solo shemale clip for TGirls, putting her look and personality on display in a self-pleasure showcase. The performer takes her time in a relaxed, well-shot solo clip from one of the dedicated TS studios. Good for fans of the performer.

↓ Free download »

Kendall Penny Strokes and Cums Solo Shemale Masturbation

Dec 07

Kendall Penny, Masturbation, Shemale, Solo

Kendall Penny Strokes and Cums Solo Shemale Masturbation - Trans Porn Video on TranyVIP

👁 12

7-12-2024, 05:20

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👤 Models: Kendall Penny

📺 Quality: HD 720p

Kendall Penny returns for her second solo of 2020, stripping down and masturbating to a hands-on cumshot in this shemale solo clip packed with her trademark enthusiasm.

↓ Free download »

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