Premium - all 44 sites in HD, from \$0.27/day See all sites

Shemale On Male Extreme Porn - Brutal Fetish Videos

All the shemale on male extreme videos on XXXExtreme, pushed past normal. Watch online or grab off VipFile.cc, free.

WinterxxDoll's Solo Transsexual Bout - Shemale - Ladyboy

Jun 09

Male On Shemale / Shemale On Male / Rimjob / Sex Toys / Blowjob

WinterxxDoll's Solo Transsexual Bout - Shemale - Ladyboy - Extreme Porn Video on XXXExtreme

👁 59

9-06-2026, 10:37

0
1
2
3
4
5

See the out-of-control WinterxxDoll in a torrid solo transsexual blowout filled with male on shemale action.

↓ Free download »

Kourtney Dash TS Slayer - A Fetish Fan's Dream! - Trans

Jun 08

Shemale On Male / Ebony / Blowjob / Big Cock

Kourtney Dash TS Slayer - A Fetish Fan's Dream! - Trans - Extreme Porn Video on XXXExtreme

👁 16

8-06-2026, 16:58

0
1
2
3
4
5

Kourtney Dash drops a crazy and dominating show that will have you on the edge of your seat.

↓ Free download »

Transsexual Action: Kelly Melo & Maira Dimov Double Team Peter Rocket

May 30

Bareback / Cum On Mouth / Hardcore / Cumshot / Shemale On Male / Threesome

Transsexual Action: Kelly Melo & Maira Dimov Double Team Peter Rocket - Extreme Porn Video on XXXExtreme

👁 3

30-05-2026, 14:15

0
1
2
3
4
5

Check it out for a wicked ride as Kelly Melo and Maira Dimov take turns double-teaming Peter Rocket in this skanky Shemale On Male threesome!

↓ Free download »

Jonelle Brooks' Trans Clip | Shemale Dominates in Oral

May 29

Shemale Dominate / Oral / Transsexuals / Shemale On Male / Hardcore / Cumshot / Shemale / Anal

Jonelle Brooks' Trans Clip | Shemale Dominates in Oral - Extreme Porn Video on XXXExtreme

👁 11

29-05-2026, 19:03

0
1
2
3
4
5

Transsexual goddess Jonelle Brooks dominates with her oral mastery in this downright skanky shemale raunchy video.

↓ Free download »

Briggite Berluscconi - Transsexual Sensation - Shemale

May 25

Cumshot / Male On Shemale / Shemale / Oral / Transsexuals / Anal / Shemale On Male / BDSM

Briggite Berluscconi - Transsexual Sensation - Shemale - Extreme Porn Video on XXXExtreme

👁 13

25-05-2026, 19:40

0
1
2
3
4
5

👤 Models: Briggite Berluscconi

📺 Quality: FullHD 1080p

Smoldering rowdy XXX starring trans superstar Briggite Berluscconi! Watch now.

↓ Free download »

Jacquelin Braxton - A Flip-Flop Shemale Show - Trans

Apr 23

Anal / FlipFlop / Hardcore / Shemale On Male

Jacquelin Braxton - A Flip-Flop Shemale Show - Trans - Extreme Porn Video on XXXExtreme

👁 7

23-04-2026, 09:10

0
1
2
3
4
5

👤 Models: Jacquelin Braxton

🎬 Studio: DeviantHardcore.com

📺 Quality: HD 720p

Look at a untamed ride as Jacquelin Braxton drops her versatile skills in this rough flip-flop sordid clip.

↓ Free download »

Leticia Freitas - Nasty, Full Transsexual - Shemale

Apr 22

FlipFlop / Shemale On Male / Hardcore / Anal

Leticia Freitas - Nasty, Full Transsexual - Shemale - Extreme Porn Video on XXXExtreme

👁 2

22-04-2026, 21:40

0
1
2
3
4
5

👤 Models: Leticia Freitas

🎬 Studio: SheMalesFromHell.com

📺 Quality: HD 720p

Show the heat as Leticia Freitas peels off her clothes and brings a sleazy, full transsexual clip that will leave you breathless!

↓ Free download »

Jenna Gargles & Spencer Fox - Filthy Transsexual Action - Shemale

Apr 20

FlipFlop / Shemale On Male / Anal / Hardcore / Bareback

Jenna Gargles & Spencer Fox - Filthy Transsexual Action - Shemale - Extreme Porn Video on XXXExtreme

👁 4

20-04-2026, 18:12

0
1
2
3
4
5

👤 Models: Jenna Gargles

📺 Quality: HD 720p

Watch a filthy and explicit flip flop savage show as Jenna Gargles and Spencer Fox deliver a memorable shemale on male romp!

↓ Free download »

Transsexual Domination: Kitty Doll's Firm Spanking - Shemale

Apr 20

Plug / Oral / Toys / Shemale On Male / Fingering / Domination / Spanking / Dildo

Transsexual Domination: Kitty Doll's Firm Spanking - Shemale - Extreme Porn Video on XXXExtreme

👁 16

20-04-2026, 08:43

0
1
2
3
4
5

Kitty Doll's powerful reign leaves no room for mercy in this spicy transsexual video.

↓ Free download »

Mia Maffia & Estelle Mounty: Fiery Shemale Bareback Action

Apr 17

Bareback / Ass Licking / Hardcore / Shemale On Male

Mia Maffia & Estelle Mounty: Fiery Shemale Bareback Action - Extreme Porn Video on XXXExtreme

👁 1

17-04-2026, 22:54

0
1
2
3
4
5

Red-hot bareback encounter showing off two gorgeous shemales, Mia Maffia and Estelle Mounty.

↓ Free download »

Grazy Cinturinha's Nasty Transsexual Vibe - Shemale - Ladyboy

Apr 14

Shemale On Male / Anal / Hardcore

Grazy Cinturinha's Nasty Transsexual Vibe - Shemale - Ladyboy - Extreme Porn Video on XXXExtreme

👁 3

14-04-2026, 16:42

0
1
2
3
4
5

👤 Models: Grazy Cinturinha

🎬 Studio: BrazilTGirls.xxx

📺 Quality: HD 720p

Grazy Cinturinha brings her torrid charm to a rough shemale on male kink from BrazilTGirls.xxx. Catch the atmosphere heat up!

↓ Free download »

Jazzy Thick Dick Topping with Uninhibited Anal Action - Trans

Apr 10

POV / Asian / Anal / Shemale On Male / Ladyboy / Hardcore

Jazzy Thick Dick Topping with Uninhibited Anal Action - Trans - Extreme Porn Video on XXXExtreme

👁 7

10-04-2026, 21:43

0
1
2
3
4
5

👤 Models: Jazzy

📺 Quality: FullHD 1080p

Jazzy Thick Dick Topping with Sinful Anal Thrills - Watch Now!

↓ Free download »

Michelly Araujo and Vinny's Trans Showdown - Shemale

Apr 07

Shemale On Male / Male On Shemale / Oral / Anal

Michelly Araujo and Vinny's Trans Showdown - Shemale - Extreme Porn Video on XXXExtreme

👁 6

7-04-2026, 15:15

0
1
2
3
4
5

👤 Models: Michelly Araujo

📺 Quality: HD 720p

Atmosphere meets desire in this sweaty transsexual video featuring Michelly Araujo and Vinny.

↓ Free download »

Bondage Captive Sasha de Sade's Flip Flop Nasty Action

Apr 02

Sissy / Role Play / FlipFlop / Anal / Hardcore / Bondage / Shemale On Male

Bondage Captive Sasha de Sade's Flip Flop Nasty Action - Extreme Porn Video on XXXExtreme

👁 5

2-04-2026, 13:30

0
1
2
3
4
5

👤 Models: Sasha de Sade

🎬 Studio: SashaDeSade.xxx

📺 Quality: HD 720p

Bondage Captive Sasha de Sade: Balls-out Transgression!

↓ Free download »

Atmospheric Trans with Miss Isa LaCrux - Shemale

Apr 02

Hardcore / Anal / Shemale On Male / FlipFlop

Atmospheric Trans with Miss Isa LaCrux - Shemale - Extreme Porn Video on XXXExtreme

👁 8

2-04-2026, 09:05

0
1
2
3
4
5

👤 Models: Miss Isa LaCrux

🎬 Studio: Femout.xxx

📺 Quality: HD 720p

Atmospheric trans hard with the enchanting Miss Isa LaCrux in this sordid shemale on male and flip-flop video.

↓ Free download »

Mikky Fucks Gabe B's Ass Hard - Trans - Shemale - Ladyboy

Apr 01

Anal / Shemale On Male / Asian / Bareback / Hardcore

Mikky Fucks Gabe B's Ass Hard - Trans - Shemale - Ladyboy - Extreme Porn Video on XXXExtreme

👁 7

1-04-2026, 09:23

0
1
2
3
4
5

👤 Models: Mikky

📺 Quality: HD 720p

Mikky and Gabe B give Mike the top hard shemale show.

↓ Free download »

Jhoanny Wilker Trans Showdown | Shemale On Male

Mar 30

Hardcore / Shemale On Male / Anal

Jhoanny Wilker Trans Showdown | Shemale On Male - Extreme Porn Video on XXXExtreme

👁 25

30-03-2026, 09:32

0
1
2
3
4
5

👤 Models: Jhoanny Wilker

🎬 Studio: SheMalesFromHell.com

📺 Quality: HD 720p

Jhoanny Wilker stars in this hot transsexual encounter, leaving no pleasure untapped as she takes power in a sordid Twisted showdown.

↓ Free download »

Milky's Relentless Flip-Flop with Gabe | Shemale On Male, Asian

Mar 29

Shemale On Male / Anal Beads / Anal / Asian / Hardcore / FlipFlop / Bareback

Milky's Relentless Flip-Flop with Gabe | Shemale On Male, Asian - Extreme Porn Video on XXXExtreme

👁 9

29-03-2026, 15:59

0
1
2
3
4
5

👤 Models: Milky

📺 Quality: HD 720p

Milky and Gabe deliver a husky flip-flop savage video that is sure to leave you hot and bothered - don't miss the naughty hijinks!

↓ Free download »

Noi - Shemale Porn Star - Trans - Ladyboy - Tgirl - Trans Girl

Mar 29

Shemale On Male / Anal / Hardcore

Noi - Shemale Porn Star - Trans - Ladyboy - Tgirl - Trans Girl - Extreme Porn Video on XXXExtreme

👁 3

29-03-2026, 11:24

0
1
2
3
4
5

👤 Models: Noi

🎬 Studio: LadyBoyPlay.com

📺 Quality: HD 720p

Peep the flirty world Noi, a grubby shemale star dominating her male counterpart in this sinful clip.

↓ Free download »

Numing Swallower In Red: A Teasing Stockings Fetish Video!

Feb 05

Stroking / Big Cock / Anal / Shemale On Male / Shemale / Short Hair / Panties / Blowjob / Ladyboy / Bareback / POV / Natural Tits / Handjob / Frottage / Transsexuals / Rimming / Cumshots / Blonde / Asian / Closeups / Pantie Aside / Swallowing / Stockings / Oil / Facial

Numing Swallower In Red: A Teasing Stockings Fetish Video! - Extreme Porn Video on XXXExtreme

👁 3

5-02-2026, 11:20

0
1
2
3
4
5

👤 Models: Numing

🎬 Studio: LadyboyGold.com

📺 Quality: HD 720p

The no-holds-barred Numing teases you with her come-hither stockings and big cock in this drool-worthy shameless video! Watch now!

↓ Free download »

Most searched on XXXExtreme:

🔥 Popular Extreme Categories

BDSM Femdom Pissing Fisting Scat Shemale & Ladyboy Pregnant