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Pain: 110 Videos, grouped by Popularity

Stunning Ladyboy Hooker Episode 21
11:14

Stunning Ladyboy Hooker Episode 21

Shemale tranny cumshots
01:31:03

Shemale tranny cumshots

Hot trap blows and gets painfully fucked on webcam
04:30

Hot trap blows and gets painfully fucked on webcam

I need the pain in my ass
30:28

I need the pain in my ass

The girls begin this guys journey into pain by smacking his uncut cock with their crops and making fun of his small penis. He can't say anything being tied up and gagged. They humiliate him with spit, make him suck on their boots and of course they wrec
02:59

The girls begin this guys journey into pain by smacking his uncut cock with their crops and making fun of his small penis. He can't say anything being tied up and gagged. They humiliate him with spit, make him suck on their boots and of course they wrec

Brazilian TS Takes Painful Anal From Giant Cock
18:06

Brazilian TS Takes Painful Anal From Giant Cock

Once again the ladies of pain are at it again. Dany,
03:02

Once again the ladies of pain are at it again. Dany,

Beautiful tranny double cumshot
01:50

Beautiful tranny double cumshot

Kiss, pain, and intimate moments
18:34

Kiss, pain, and intimate moments

Pleasure and pain 2
26:26

Pleasure and pain 2

Nipple torture pain for Tgirl
05:00

Nipple torture pain for Tgirl

Stunning Ladyboy Hooker Episode 33
11:46

Stunning Ladyboy Hooker Episode 33

Pain free Kitty Kaiti..mega load
02:13

Pain free Kitty Kaiti..mega load

Super cute teen Ladyboy getting fucked in the ass wit no pain, only pleasure
20:30

Super cute teen Ladyboy getting fucked in the ass wit no pain, only pleasure

Stunning Ladyboy Hooker Episode 32
11:56

Stunning Ladyboy Hooker Episode 32

shemale painfully anal fucked
17:54

shemale painfully anal fucked

Tranny has painful anal with a married guy at her place
10:17

Tranny has painful anal with a married guy at her place

Pain ladyboy, piladyboy
13:42

Pain ladyboy, piladyboy

Stunning Ladyboy Hooker Episode 16
10:57

Stunning Ladyboy Hooker Episode 16

Stunning Ladyboy Pounded Episode 10
09:38

Stunning Ladyboy Pounded Episode 10

Stunning Ladyboy Hooker Episode 20
11:24

Stunning Ladyboy Hooker Episode 20

Stunning Ladyboy Hooker Episode 28
11:21

Stunning Ladyboy Hooker Episode 28

Stunning Ladyboy Hooker Episode 34
11:52

Stunning Ladyboy Hooker Episode 34

Seducing Him lusty addison insane painf
15:16

Seducing Him lusty addison insane painf

Young shemale painfully anal fucked
21:47

Young shemale painfully anal fucked

Emily tied up to ceiling on tiptoes and tortured by Erika
02:51

Emily tied up to ceiling on tiptoes and tortured by Erika

Shemale with leather cloth likes cruel sex with pain in her apartment
19:49

Shemale with leather cloth likes cruel sex with pain in her apartment

Stunning Ladyboy Hooker Episode 36
12:05

Stunning Ladyboy Hooker Episode 36

crossdresser punishment
19:30

crossdresser punishment

Stunning Ladyboy Hooker Episode 45
14:36

Stunning Ladyboy Hooker Episode 45

Crossdresser enjoys a very painful flogging session in the dungeon
14:59

Crossdresser enjoys a very painful flogging session in the dungeon

Lover with big cock fucks painful small tits shemale
04:59

Lover with big cock fucks painful small tits shemale

Stunning Ladyboy Hooker Episode 47
15:19

Stunning Ladyboy Hooker Episode 47

Stunning Ladyboy Hooker Episode 24
11:34

Stunning Ladyboy Hooker Episode 24

Anal fist fuck faggot love to feel the pain in the ass
18:18

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

Crossdreseer fuck men, amateur threesome
24:36

Crossdreseer fuck men, amateur threesome

Pleasure and pain
21:12

Pleasure and pain

Stunning Ladyboy Hooker Episode 37
12:22

Stunning Ladyboy Hooker Episode 37

Foot worship, feet worship, painful crossdressing bbc
11:07

Foot worship, feet worship, painful crossdressing bbc

Gold Predator BBC Brutally Destroys White Sluts Hole & Makes Me Scream
10:28

Gold Predator BBC Brutally Destroys White Sluts Hole & Makes Me Scream

Stunning Ladyboy Hooker Episode 29
11:22

Stunning Ladyboy Hooker Episode 29

Sylvia & Drew
18:37

Sylvia & Drew

Skinny Blonde Tranny Loves Pain and Pleasure
09:07

Skinny Blonde Tranny Loves Pain and Pleasure

CBT with Needles and Sounding
05:01

CBT with Needles and Sounding

Loud Asian Ladyboy Screaming with Pain from a Big Cock
19:23

Loud Asian Ladyboy Screaming with Pain from a Big Cock

Stunning Ladyboy Hooker Episode 23
11:29

Stunning Ladyboy Hooker Episode 23

Girl loves pain and cum
10:00

Girl loves pain and cum

Stunning Ladyboy Hooker Episode 60
10:49

Stunning Ladyboy Hooker Episode 60

Shemales first time painful anal sex with 8 inch dick
07:55

Shemales first time painful anal sex with 8 inch dick

Web teen 32 lusty addison insane painfu
27:29

Web teen 32 lusty addison insane painfu

Stunning Ladyboy Hooker Episode 19
11:03

Stunning Ladyboy Hooker Episode 19

Stunning Ladyboy Pounded Episode 7
09:48

Stunning Ladyboy Pounded Episode 7

Pain Is Her Pleasure
14:58

Pain Is Her Pleasure

Stunning Ladyboy Pounded Episode 9
09:51

Stunning Ladyboy Pounded Episode 9

Stunning Ladyboy Hooker Episode 15
10:29

Stunning Ladyboy Hooker Episode 15

Predominance, trans
14:53

Predominance, trans

debbie heart tv whipping myself for my mistress
04:05

debbie heart tv whipping myself for my mistress

Young shemale painfully fucked in her mouth and ass
27:27

Young shemale painfully fucked in her mouth and ass

The Mistresses of pain are hungry for fresh meat. They
02:59

The Mistresses of pain are hungry for fresh meat. They

Petite teen ladyboy gets fucked hard and painful
04:00

Petite teen ladyboy gets fucked hard and painful

Stunning Ladyboy Pounded Episode 8
09:30

Stunning Ladyboy Pounded Episode 8

Amateur, ballbusting, bizarre, punishment, pain, Humiliation
15:26

Amateur, ballbusting, bizarre, punishment, pain, Humiliation

Amateur tranny blowjob and danidaniels blowjob Karel is pain
05:56

Amateur tranny blowjob and danidaniels blowjob Karel is pain

Homemade anal fucking with argentinian girlfriend
28:46

Homemade anal fucking with argentinian girlfriend

Emo twinks have anal fun
23:44

Emo twinks have anal fun

White ts, pretty ladyboy sex, rough painful anal
11:27

White ts, pretty ladyboy sex, rough painful anal

Shemale Korra Del Rio Painful Anal
05:23

Shemale Korra Del Rio Painful Anal

Painful, hard crying, very painful crying anal
29:33

Painful, hard crying, very painful crying anal

Stunning Ladyboy Hooker Episode 41
13:27

Stunning Ladyboy Hooker Episode 41

Danni screaming on pain and pleasure
36:55

Danni screaming on pain and pleasure

Shemale Korra Del Rio Painful Anal
05:23

Shemale Korra Del Rio Painful Anal

Crossdresser enjoys a very painful flogging session
08:17

Crossdresser enjoys a very painful flogging session

Stunning Ladyboy Hooker Episode 44
14:12

Stunning Ladyboy Hooker Episode 44

Dirty Ladyboy gets painful fucking
04:00

Dirty Ladyboy gets painful fucking

Pain for my big tits shooting members h
09:55

Pain for my big tits shooting members h

More Amateur Girls on TubEvent lusty ad
13:04

More Amateur Girls on TubEvent lusty ad

Transvestite Taking Huge Dildo
13:45

Transvestite Taking Huge Dildo

Stunning Ladyboy Hooker Episode 26
11:23

Stunning Ladyboy Hooker Episode 26

ANAL with PAIN
01:18

ANAL with PAIN

Stunning Ladyboy Hooker Episode 4
08:32

Stunning Ladyboy Hooker Episode 4

Binded shemale gets pain
59:42

Binded shemale gets pain

Stunning Ladyboy Hooker Episode 1
04:51

Stunning Ladyboy Hooker Episode 1

Stunning Ladyboy Hooker Episode 31
11:45

Stunning Ladyboy Hooker Episode 31

Young shemale painfully anal fucked
11:52

Young shemale painfully anal fucked

Shemale Korra Del Rio Painful Anal
05:23

Shemale Korra Del Rio Painful Anal

Ladyboy Meen Painful Bareback
06:00

Ladyboy Meen Painful Bareback

First time painal
16:17

First time painal

submissive tgirl hottie is painfully humiliated and learns how to be a pretty lil sex slave
17:35

submissive tgirl hottie is painfully humiliated and learns how to be a pretty lil sex slave

Stunning Ladyboy Hooker Episode 6
09:50

Stunning Ladyboy Hooker Episode 6

Stunning Ladyboy Hooker Episode 64
04:00

Stunning Ladyboy Hooker Episode 64

Tranny Soothing Guy Pain With Fuck
21:05

Tranny Soothing Guy Pain With Fuck

Stunning Ladyboy Hooker Episode 25
11:27

Stunning Ladyboy Hooker Episode 25

Stunning Ladyboy Hooker Episode 43
14:06

Stunning Ladyboy Hooker Episode 43

Stunning Ladyboy Hooker Episode 62
15:29

Stunning Ladyboy Hooker Episode 62

Stunning Ladyboy Hooker Episode 48
15:35

Stunning Ladyboy Hooker Episode 48

Stunning Ladyboy Hooker Episode 46
14:54

Stunning Ladyboy Hooker Episode 46

Painful day
20:28

Painful day

Crossdresser enjoys a very painful flogging session in the d
21:10

Crossdresser enjoys a very painful flogging session in the d

Teen Girls Get Naked on Chaturbute lust
14:05

Teen Girls Get Naked on Chaturbute lust

Skinny Ladyboy Pink Painful Bareback
05:51

Skinny Ladyboy Pink Painful Bareback

Stunning Ladyboy Hooker Episode 22
11:10

Stunning Ladyboy Hooker Episode 22

Stunning Ladyboy Hooker Episode 18
11:07

Stunning Ladyboy Hooker Episode 18

Submissive Slave gets painful ass frigging
19:28

Submissive Slave gets painful ass frigging

Stunning Ladyboy Pounded Episode 12
09:51

Stunning Ladyboy Pounded Episode 12

Stunning Ladyboy Hooker Episode 13
10:37

Stunning Ladyboy Hooker Episode 13

Hentai overwatch, halloween tranny anime, pain compilation
10:35

Hentai overwatch, halloween tranny anime, pain compilation

Painful Fisting For Big Tranny Bum
18:29

Painful Fisting For Big Tranny Bum