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10 months ago
26:03

aShemaleTube

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4 months ago
8:34

aShemaleTube

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1 year ago
51:35

XXXDan

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Sadistic TS Domme Takes Special Care Of Her Slaves
6 years ago
36:42

aShemaleTube

Sadistic TS Domme Takes Special Care Of Her Slaves

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7 years ago
4:10

aShemaleTube

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7 years ago
6:15

FetishPapa

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1 year ago
9:20

aShemaleTube

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4 years ago
16:17

aShemaleTube

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7 years ago
6:15

FetishPapa

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3 months ago
26:32

aShemaleTube

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1 year ago
30:10

XXXDan

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3 years ago
10:27

KeekAss

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3 years ago
7:27

aShemaleTube

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2 years ago
8:22

ShemaleTaxi

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10 months ago
17:57

aShemaleTube

Bbc Shemale fucks boy and cum inside ass

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1 year ago
9:51

KeekAss

Goddess Fucks a Slut Painfull on Fetish.

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2 years ago
1:12

aShemaleTube

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Latina TS Iza Mendez Roughly Barebacked
9 years ago
5:46

aShemaleTube

Latina TS Iza Mendez Roughly Barebacked

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1 year ago
4:11

aShemaleTube

Rayray Sugarbutt puts her cock and balls inside her bitch's asshole

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4 years ago
4:58

aShemaleTube

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5 years ago
1:41

aShemaleTube

1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR

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Smallish Trans Artemis Asteria Taunts Her Roomy
2 years ago
11:39

KeekAss

Smallish Trans Artemis Asteria Taunts Her Roomy

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4 years ago
3:21

TrannyOne

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Obedient Training - Ache Tolerance (Nipp Play)
7 months ago
12:33

ShemaleSin

Obedient Training - Ache Tolerance (Nipp Play)

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2 years ago
3:11

ShemaleSin

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8 years ago
14:11

aShemaleTube

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1 year ago
2:05

aShemaleTube

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2 years ago
5:08

KeekAss

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3 years ago
20:07

ShemaleSin

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3 years ago
2:09

TrannyOne

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Tranny Spanked By The Sadistic Sex Fiends!
9 months ago
15:00

ABTranny

Tranny Spanked By The Sadistic Sex Fiends!

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30 days ago
5:18

XXXVogue

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1 year ago
2:14

aShemaleTube

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2 years ago
20:53

KeekAss

Painful Lesson Taught By The Big Dick Tranny

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5 years ago
9:45

ShemaleSin

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4 years ago
4:11

TrannyOne

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5 years ago
6:25

ShemaleMovie

she-creature Pang 19 years aged ass fucking

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2 months ago
3:19

ShemaleSin

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1 year ago
6:39

ShemaleSin

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2 years ago
6:47

XXXDan

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2 years ago
7:37

aShemaleTube

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1 year ago
5:17

ShemaleMovie

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5 months ago
6:56

FapCat

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1 year ago
7:54

ShemaleTaxi

Transgender princess Daisy Taylor getting painted

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Muscular Trans beauties ditch protection after hitting the gym
1 year ago
11:44

ShemaleMovie

Muscular Trans beauties ditch protection after hitting the gym

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2 years ago
36:56

TrannyOne

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Stacy Sadistic Fuck Girl
3 months ago
38:09

aShemaleTube

Stacy Sadistic Fuck Girl

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14 years ago
19:07

aShemaleTube

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3 months ago
11:03

ShemaleTaxi

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4 years ago
6:51

aShemaleTube

Shemale Painful Anal Fuck 30x6 cm + 2 Cumshots

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4 years ago
7:20

TrannyOne

Shemale gives painful fuck to white guy

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4 years ago
5:58

aShemaleTube

girls sadistic Shemale Live Cum Show

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Colleen TS Self Paddling - at least 100 strokes
6 years ago
1:21

aShemaleTube

Colleen TS Self Paddling - at least 100 strokes

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14 years ago
19:28

aShemaleTube

Submissive Slave gets painful ass frigging

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5 years ago
1:49

aShemaleTube

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10 years ago
6:43

aShemaleTube

Anal Pain

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3 years ago
7:50

aShemaleTube

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2 years ago
10:17

aShemaleTube

Tranny has painful anal with a married guy at her place

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2 years ago
6:27

aShemaleTube

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1 year ago
11:29

ShemaleSin

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1 year ago
4:54

aShemaleTube

shemale breaks her bf's ass with her huge cock

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14 years ago
7:04

aShemaleTube

Tattoo muscle-boy drills hard and painful sexy t-girl to her cum

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11 years ago
5:29

aShemaleTube

Busty transsexual gives straight guy some painful delight

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Lesbians dominate and ass-fuck the plump pizza delivery girl Lily Labeau
7 months ago
5:34

ShemaleMovie

Lesbians dominate and ass-fuck the plump pizza delivery girl Lily Labeau

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Spanked by the Sadistic Sex Fiends!
4 years ago
7:37

aShemaleTube

Spanked by the Sadistic Sex Fiends!

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Ladyboy Meen Painful Bareback
9 years ago
6:15

aShemaleTube

Ladyboy Meen Painful Bareback

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Sadistic Interracial Black Tgirls Fuck Live Webcam
6 years ago
3:41

aShemaleTube

Sadistic Interracial Black Tgirls Fuck Live Webcam

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1 year ago
5:10

HDSex

Unexpected shemale

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4 years ago
6:15

aShemaleTube

Skinny trans nanny takes care of the parent's needs too

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6 years ago
2:11

aShemaleTube

CD nipples pain and cum out

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Shy Ladyboy Pang Fucked Bareback
10 years ago
6:57

aShemaleTube

Shy Ladyboy Pang Fucked Bareback

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10 years ago
7:09

aShemaleTube

Shemale brunette screaming in pain of pleasure

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Pain and pleasure chastity and lust Part
4 years ago
8:48

aShemaleTube

Pain and pleasure chastity and lust Part

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2 years ago
6:23

aShemaleTube

Ladyboy feels pain in ass after giving nice blowjob

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1 year ago
3:08

ShemaleSin

Pang makes the honey indeed concupiscent

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1 year ago
5:17

ShemaleMovie

Atm, porn-vido

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Painful Bareback Anal For Hung Ladyboy Jasmine
4 years ago
6:01

aShemaleTube

Painful Bareback Anal For Hung Ladyboy Jasmine

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GAY BRAZIL AND SHEMALE ANAL PAIN GANG
3 years ago
4:48

aShemaleTube

GAY BRAZIL AND SHEMALE ANAL PAIN GANG

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Shemale Korra Del Rio Painful Anal
9 years ago
5:24

aShemaleTube

Shemale Korra Del Rio Painful Anal

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3 years ago
16:17

aShemaleTube

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Ladyboy May Tight Hairy Ass
11 years ago
6:15

aShemaleTube

Ladyboy May Tight Hairy Ass

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4 years ago
8:54

aShemaleTube

girls sadistic Shemale Live Cum Show

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Crossdresser Enjoys a very Painful Flogging Session in
5 years ago
11:29

aShemaleTube

Crossdresser Enjoys a very Painful Flogging Session in

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8 years ago
6:21

aShemaleTube

Pain and pleasure

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Ladyboy Pink Painful Bareback
9 years ago
6:19

aShemaleTube

Ladyboy Pink Painful Bareback

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Stacy Sadistic Has Her Way With Moist Snatch
1 year ago
13:08

ShemaleSin

Stacy Sadistic Has Her Way With Moist Snatch

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2 years ago
17:06

ShemaleTaxi

Predominance, slit

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Kiss, pain, and intimate moments
2 years ago
18:34

aShemaleTube

Kiss, pain, and intimate moments

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Amateur Ladyboy Darly Barebacked
4 years ago
6:17

ShemaleSin

Amateur Ladyboy Darly Barebacked

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Pain PMV by Blitz
8 years ago
6:18

aShemaleTube

Pain PMV by Blitz

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11 years ago
17:20

aShemaleTube

Painful insertions into chaps ass

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ANDY-STAR BANGS TRANSGENDER ANAL HARDCORE SEMEN TRANSSEXUAL FROM SPAIN
7 months ago
7:07

ShemaleSin

ANDY-STAR BANGS TRANSGENDER ANAL HARDCORE SEMEN TRANSSEXUAL FROM SPAIN

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19 years old Anal Ladyboy Gets Cock
11 years ago
6:14

aShemaleTube

19 years old Anal Ladyboy Gets Cock

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Super cute Ladyboy getting drilled in the butt wit no ache, merely fun
1 year ago
20:30

ShemaleSin

Super cute Ladyboy getting drilled in the butt wit no ache, merely fun

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Insane huge dildo - Part 5 (painful fart)
2 years ago
0:54

aShemaleTube

Insane huge dildo - Part 5 (painful fart)

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Eurasian Persuasion, Punishing Loser
4 years ago
8:03

TrannyOne

Eurasian Persuasion, Punishing Loser

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Super Cute Teen Ladyboy Getting Fucked In The Ass Wit No Pain, Only Pleasure.
4 years ago
20:18

TrannyOne

Super Cute Teen Ladyboy Getting Fucked In The Ass Wit No Pain, Only Pleasure.

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Blonde, nerdy porn star wearing glasses After a painful urethra insertion, Lianna Lawson jerks off her wood-hard dick and sprays warm cum.
1 year ago
8:55

FapCat

Blonde, nerdy porn star wearing glasses After a painful urethra insertion, Lianna Lawson jerks off her wood-hard dick and sprays warm cum.

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Big tits tranny Pang sucked dick before hard ass fucking by a white client
4 years ago
6:00

aShemaleTube

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14 years ago
4:59

aShemaleTube

Lover with big cock fucks painful small tits shemale

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2 years ago
5:07

KeekAss

Bootie screw for t-girl untill climax

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Maya Lafayette Destroys Bottom With Pain And Pleasure
5 months ago
32:30

ABTranny

Maya Lafayette Destroys Bottom With Pain And Pleasure

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Stranger Caught Forest Girl bound her to tree and Fucked rough hardcore.
1 year ago
3:39

FapCat

Stranger Caught Forest Girl bound her to tree and Fucked rough hardcore.

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Feb 2nd 2023
3 years ago
20:07

ShemaleSin

Feb 2nd 2023

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Cy's Palace of Pleasure and Pain: 50 Shades of Hardcore Shemale Domination
2 years ago
23:10

ShemaleTaxi

Cy's Palace of Pleasure and Pain: 50 Shades of Hardcore Shemale Domination

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Free-tranny-videos, anal-pain-porn
4 years ago
5:17

ShemaleMovie

Free-tranny-videos, anal-pain-porn

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1 year ago
15:36

ShemaleMovie

Intense pleasure, pain play & submission

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1 year ago
5:18

ShemaleTaxi

Everythingbutt, rimjob

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Mastix Mercer Disciplinary Rod and Ball Anguish for Wicked Chastity Sissy Erica
5 months ago
1:40

ShemaleSin

Mastix Mercer Disciplinary Rod and Ball Anguish for Wicked Chastity Sissy Erica

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Sadistictranskitty KdamaGrey
4 years ago
1:32

aShemaleTube

Sadistictranskitty KdamaGrey

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Ladyboy painful assfuck with huge knob
11 months ago
6:27

AnalDin

Ladyboy painful assfuck with huge knob

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Shy Submissive Brunette Shemale Spanked By The Sadistic Sex Friend! - Sgt Miles
2 years ago
15:00

XHand

Shy Submissive Brunette Shemale Spanked By The Sadistic Sex Friend! - Sgt Miles

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Shemale Pang Gets Herself Off
5 years ago
5:00

aShemaleTube

Shemale Pang Gets Herself Off

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Big-breasted furry dominatrix anally pounds submissive man
1 year ago
5:21

ShemaleMovie

Big-breasted furry dominatrix anally pounds submissive man

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Redhead Oriental ladyboy all overspread in ache gets banged doggy position untill facial
1 year ago
7:05

ShemaleSin

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Zelda's Pang & Fun - Futanari Comics Anal JOI W/ Metronome
4 years ago
11:49

ShemaleSin

Zelda's Pang & Fun - Futanari Comics Anal JOI W/ Metronome

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Ladyboy painful anal with huge dick
1 year ago
6:27

aShemaleTube

Ladyboy painful anal with huge dick

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1 year ago
9:44

JizzBunker

Kinky iris very painful lifting 4,2 kilo on nipples

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5 months ago
8:52

ShemaleSin

Close up ejaculation and teat ache

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2 years ago
12:31

ShemaleTaxi

Craiglist, breeding

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Ladyboys In PAIN: Volume 5
4 years ago
8:05

TrannyOne

Ladyboys In PAIN: Volume 5

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TrannyBanger inserts a giant veggie in the booty of a trans beauty so unfathomable that that babe is gasping from the ache and enjoyment as it fills h
4 years ago
5:32

ShemaleSin

TrannyBanger inserts a giant veggie in the booty of a trans beauty so unfathomable that that babe is gasping from the ache and enjoyment as it fills h

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1 year ago
6:00

ShemaleSin

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TRANS DOMINADORA BANGED ME OUT OF ACHE
2 years ago
5:00

ShemaleSin

TRANS DOMINADORA BANGED ME OUT OF ACHE

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Sissy BBC Painful Anal Training
5 years ago
10:56

PornoXO

Sissy BBC Painful Anal Training

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Muscular Hunk Is Restrained For Bondage Pleasure
3 years ago
4:00

FlyFlv

Muscular Hunk Is Restrained For Bondage Pleasure

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Sadistic experimentation
1 year ago
0:43

ShemaleSin

Sadistic experimentation

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Kinky Forest Girl tied to tree and fucked by Hunter. Stranger caught forest girl bound her to tree in middle of the forest and fucked her.
1 year ago
3:13

FapCat

Kinky Forest Girl tied to tree and fucked by Hunter. Stranger caught forest girl bound her to tree in middle of the forest and fucked her.

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Rollenspiel, marionette
1 year ago
10:29

ShemaleMovie

Rollenspiel, marionette

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Painful nice big cock
4 years ago
1:51

aShemaleTube

Painful nice big cock

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Transgender princess, lean
3 years ago
18:11

ShemaleMovie

Transgender princess, lean

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Pang Is Her Fun
5 years ago
14:58

ShemaleSin

Pang Is Her Fun

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Ticklish t-girl gets Pedicure from Sadist Aunt TEASER
3 years ago
0:33

ShemaleSin

Ticklish t-girl gets Pedicure from Sadist Aunt TEASER

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Blondes Sexmonster bekommt es Double Penetration
3 years ago
21:16

TrannyOne

Blondes Sexmonster bekommt es Double Penetration

Tags: 18 year old, amateur, anal, blonde, blowjob, brutal, double penetration

Painslut Instructing with Sir James & Princess Kyaa in the Sensuous Agony Basement *directors Cut*
5 years ago
14:46

KeekAss

Painslut Instructing with Sir James & Princess Kyaa in the Sensuous Agony Basement *directors Cut*

Tags: anal, basement, bdsm, blonde, bondage, cage, domination

Massage Session Goes Wild As Trannies Get Out Of Control
2 years ago
6:13

FlyFlv

Massage Session Goes Wild As Trannies Get Out Of Control

Tags: anal, assfingering, big cock, blonde, blowjob, brunette, lesbian

Anal fist fuck faggot love to feel the pain in the ass
4 years ago
18:02

TrannyOne

Anal fist fuck faggot love to feel the pain in the ass

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Ass licking, anal-pain-porn
4 years ago
5:14

ShemaleTaxi

Ass licking, anal-pain-porn

Tags: anal, asslick, ladyboy, pain, shemale

Twink Ladyboy in pain when banged by a huge Shemale Cock
6 years ago
6:58

ShemaleZ

Twink Ladyboy in pain when banged by a huge Shemale Cock

Tags: big cock, huge cock, ladyboy, pain, shemale, small tits, twink

Fucking The Pain Away With Miss Nikita
9 months ago
5:22

aShemaleTube

Fucking The Pain Away With Miss Nikita

Tags: amateur, anal, barebacking, big cock, blonde, blowjob, cumshot

Pang1 - Doggiestyle - HelloLadyboy
5 years ago
4:04

HClips

Pang1 - Doggiestyle - HelloLadyboy

Tags: blowjob, doggystyle, ladyboy, pain, pov, shemale, teen (18+)

Asian Ladyboy Pang Fucks Herself
6 years ago
6:06

TrannyOne

Asian Ladyboy Pang Fucks Herself

Tags: hd, ladyboy, masturbation, pain, shemale

Insane huge dildo - Part 41 (moaning in pain)
1 year ago
0:40

aShemaleTube

Insane huge dildo - Part 41 (moaning in pain)

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Ts Leona paints nails before masturbation
15 years ago
10:43

aShemaleTube

Ts Leona paints nails before masturbation

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X-vidos, anal-pain-porn
5 years ago
5:14

ShemaleTaxi

X-vidos, anal-pain-porn

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Busty mummy domme jerking gimp slave in harsh femdom session
1 year ago
5:19

ShemaleMovie

Busty mummy domme jerking gimp slave in harsh femdom session

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MissRose TS - Rosanna IN PRIVATE - WILD SHEMALE, painful MASTURBATION - Rough ass, big SHAKE - cumshot
1 year ago
5:24

JizzBunker

MissRose TS - Rosanna IN PRIVATE - WILD SHEMALE, painful MASTURBATION - Rough ass, big SHAKE - cumshot

Tags: anal, ass, beauty, big ass, big cock, blonde, creampie

girls sadistic Chaturbate Webcamshow
5 years ago
1:43:01

aShemaleTube

girls sadistic Chaturbate Webcamshow

Tags: pain, shemale, webcam

Anal-fucking, xvidioes
8 months ago
5:22

ShemaleMovie

Anal-fucking, xvidioes

Tags: anal, ass, asslick, big ass, blowjob, hardcore, licking

Girl-on-girl action with some wild kink fun
8 months ago
5:36

ShemaleMovie

Girl-on-girl action with some wild kink fun

Tags: anal, ass, bdsm, bondage, fisting, funny, gaping hole

Submissive ginger Sabina Steele craves domination from transgender partner
1 year ago
8:14

ShemaleTaxi

Submissive ginger Sabina Steele craves domination from transgender partner

Tags: bdsm, boots, domination, latex, pain, shemale, submissive

Randomizer Ache Game - Birthday Spanks
3 years ago
6:40

ShemaleSin

Randomizer Ache Game - Birthday Spanks

Tags: amateur, big clit, birthday, caning, fetish, game, homevideo

A large booty shemale is offering her lover her ass to bang in this really sensual performance! It will really hurt your cock when she grunts loudly a
1 year ago
10:33

FapCat

A large booty shemale is offering her lover her ass to bang in this really sensual performance! It will really hurt your cock when she grunts loudly a

Tags: anal, ass, babe, banging, big ass, blonde, blowjob

Painful, painful anal
5 years ago
6:10

ShemaleMovie

Painful, painful anal

Tags: anal, beauty, big cock, big tits, blowjob, masturbation, pain

2 gorgeous shemales discover the painful pleasure
5 years ago
5:03

TrannyOne

2 gorgeous shemales discover the painful pleasure

Tags: dick, gorgeous, juicy, pain, shemale, tgirl, tranny

Stringing up Wedgie Fetish - Frontal Wedgie puts strain on my poon - Rips My Undies to Shreds!
2 years ago
19:03

KeekAss

Stringing up Wedgie Fetish - Frontal Wedgie puts strain on my poon - Rips My Undies to Shreds!

Tags: amateur, boy, clit, dirty, fetish, hd, masturbation

Trans Sissy Cross Crossdresser Boobs Lycra Taut Top Titties
4 years ago
0:36

ShemaleSin

Trans Sissy Cross Crossdresser Boobs Lycra Taut Top Titties

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Hot quickie with ladyboy Pang
1 year ago
5:06

aShemaleTube

Hot quickie with ladyboy Pang

Tags: amateur, anal, asian, assfucking, blowjob, dick, hd

Domination & submission, backside
8 months ago
5:34

ShemaleMovie

Domination & submission, backside

Tags: anal, ass, bdsm, bondage, domination, hardcore, pain

BBW trans dominatrix Stacy Sadistic pleases her submissive roommate with big cock
1 year ago
11:49

ShemaleTaxi

BBW trans dominatrix Stacy Sadistic pleases her submissive roommate with big cock

Tags: bbw, big cock, dominatrix, pain, shemale, submissive, transsexual

Stacy sadistic Big Cock
7 months ago
7:22

aShemaleTube

Stacy sadistic Big Cock

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Kinkysmut, gagging
10 months ago
5:28

VideoSection

Kinkysmut, gagging

Tags: anal, ass, bdsm, bondage, domination, gagging, pain

stacy sadomasochistic smacks wild kitten^utter on crimson^
1 year ago
7:00

KeekAss

stacy sadomasochistic smacks wild kitten^utter on crimson^

Tags: amateur, bbw, bdsm, big ass, crossdressing, goddess, hardcore

Tranny Spanked By The Sadistic Sex Fiends!
1 year ago
8:00

getTranny

Tranny Spanked By The Sadistic Sex Fiends!

Tags: hd, pain, spanking, stockings, tattoo, toys, tranny

Girly girl restrained in bondage for anal pleasure and domination
8 months ago
5:35

ShemaleMovie

Girly girl restrained in bondage for anal pleasure and domination

Tags: anal, ass, bdsm, bondage, domination, hardcore, pain

Ladyboy Pang Jerking Off
10 years ago
6:25

aShemaleTube

Ladyboy Pang Jerking Off

Tags: asian, hd, jerking, ladyboy, masturbation, pain, shemale

Trans Prostitute Juliette Stray Getting Assfucked Painfully But She Loves It!
5 years ago
6:13

aShemaleTube

Trans Prostitute Juliette Stray Getting Assfucked Painfully But She Loves It!

Tags: anal, assfucking, big cock, hd, lingerie, pain, shemale

Shemale Eva Enjoys Anal Sex In Honeymoon
5 years ago
6:15

aShemaleTube

Shemale Eva Enjoys Anal Sex In Honeymoon

Tags: anal, assfucking, big cock, big tits, bride, hd, pain

Stacy Sadistic Has Her Way With Moist Twat
4 months ago
11:02

ShemaleSin

Stacy Sadistic Has Her Way With Moist Twat

Tags: anal, big cock, big tits, cunt, pain, pornstar, transsexual

Wow that enormous paddle was so severe,so painful it felt like punishment,I ended up very bruised. Got despairing for him to cum near the end,I just c
3 years ago
16:47

ShemaleSin

Wow that enormous paddle was so severe,so painful it felt like punishment,I ended up very bruised. Got despairing for him to cum near the end,I just c

Tags: abuse, amateur, anal, bdsm, bondage, caning, cum

Asian TS Girl Pang A Loves Toyfucking Her Butt
4 years ago
6:05

aShemaleTube

Asian TS Girl Pang A Loves Toyfucking Her Butt

Tags: ass, big ass, brunette, hd, masturbation, pain, shemale

Curvy Therapist Treats Trans Pair With 3some
8 months ago
13:07

ShemaleSin

Curvy Therapist Treats Trans Pair With 3some

Tags: 3some, barebacking, bbw, curvy, feminization, pain, tranny

Spanked by the Sadistic Sex Fiends!.
4 years ago
7:48

aShemaleTube

Spanked by the Sadistic Sex Fiends!.

Tags: barebacking, big tits, cumshot, hd, pain, shemale, spanking

Trans Asian Pang A gets her ass fucked by a huge toy
7 years ago
5:40

aShemaleTube

Trans Asian Pang A gets her ass fucked by a huge toy

Tags: asian, assfucking, big cock, big tits, cumshot, handjob, hd

super sexy tranny getting fucked in a anus wit no pain
3 years ago
8:35

aShemaleTube

super sexy tranny getting fucked in a anus wit no pain

Tags: amateur, anus, pain, shemale, tranny

Extreme submission and female authority in BDSM scene featuring Maitresse Madeline
1 year ago
5:19

ShemaleMovie

Extreme submission and female authority in BDSM scene featuring Maitresse Madeline

Tags: bdsm, bizarre, bondage, dildo, domination, extreme, gagging

Wealthy entrepreneur dominated and pegged by a fierce female dominatrix
1 year ago
5:20

ShemaleMovie

Wealthy entrepreneur dominated and pegged by a fierce female dominatrix

Tags: anal, bdsm, bizarre, bondage, dildo, domination, dominatrix

Pain loving solo TS jerks her cock with toy in her urethra
1 year ago
5:00

XXXDan

Pain loving solo TS jerks her cock with toy in her urethra

Tags: amateur, babe, bdsm, big cock, dick, lingerie, masturbation

Pain-Getting hard fucked
4 years ago
0:59

aShemaleTube

Pain-Getting hard fucked

Tags: 3some, anal, barebacking, big cock, crossdressing, cum in mouth, domination

Curly haired ladyboy strips down and masturbates her shecock
9 years ago
7:24

aShemaleTube

Curly haired ladyboy strips down and masturbates her shecock

Tags: big tits, curly haired, ladyboy, lingerie, masturbation, pain, shemale