Top-Rated

Pain: 108 Videos, grouped by Popularity

Shemale tranny cumshots
01:31:03

Shemale tranny cumshots

Brazilian TS Takes Painful Anal From Giant Cock

Beautiful tranny double cumshot
01:50

Beautiful tranny double cumshot

Stunning Ladyboy Hooker Episode 21
11:14

Stunning Ladyboy Hooker Episode 21

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

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

Hot trap blows and gets painfully fucked on webcam

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

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

Emo twinks have anal fun
23:44

Emo twinks have anal fun

Stunning Ladyboy Hooker Episode 39
12:34

Stunning Ladyboy Hooker Episode 39

Tranny has painful anal with a married guy at her place

Stunning Ladyboy Hooker Episode 43
14:06

Stunning Ladyboy Hooker Episode 43

More Amateur Girls on TubEvent lusty ad
13:04

More Amateur Girls on TubEvent lusty ad

Stunning Ladyboy Hooker Episode 40
13:07

Stunning Ladyboy Hooker Episode 40

pain, pleasure & cum load for T-girl Alexandra
11:13

pain, pleasure & cum load for T-girl Alexandra

Teen Girls Get Naked on Chaturbute lust
14:05

Teen Girls Get Naked on Chaturbute lust

Teen guy cumsucker gets fucked painful by big ebony tranny

Stunning Ladyboy Hooker Episode 48
15:35

Stunning Ladyboy Hooker Episode 48

Pain free Kitty Kaiti..mega load
02:13

Pain free Kitty Kaiti..mega load

Stunning Ladyboy Hooker Episode 30
12:04

Stunning Ladyboy Hooker Episode 30

Tranny Soothing Guy Pain With Fuck
21:05

Tranny Soothing Guy Pain With Fuck

Stunning Ladyboy Hooker Episode 36
12:05

Stunning Ladyboy Hooker Episode 36

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

Painful, hard crying, very painful crying anal

Transvestite Taking Huge Dildo
13:45

Transvestite Taking Huge Dildo

Stunning Ladyboy Pounded Episode 8
09:30

Stunning Ladyboy Pounded Episode 8

Ladyboy Meen Painful Bareback
06:00

Ladyboy Meen Painful Bareback

Pain for my big tits shooting members h
09:55

Pain for my big tits shooting members h

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

White ts, pretty ladyboy sex, rough painful anal

Seducing Him lusty addison insane painf
15:16

Seducing Him lusty addison insane painf

Stunning Ladyboy Hooker Episode 23
11:29

Stunning Ladyboy Hooker Episode 23

shemale painfully anal fucked
17:54

shemale painfully anal fucked

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

Young shemale painfully fucked in her mouth and ass

Hot crossdresser get fuck hard by wife with strap on dildo in the ass
04:10

Hot crossdresser get fuck hard by wife with strap on dildo in the ass

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

Stunning Ladyboy Hooker Episode 31
11:45

Stunning Ladyboy Hooker Episode 31

Stunning Ladyboy Hooker Episode 1
04:51

Stunning Ladyboy Hooker Episode 1

Virgin Cara taking BBC dildo and gaping for camera
21:29

Virgin Cara taking BBC dildo and gaping for camera

Stunning Ladyboy Hooker Episode 61
14:11

Stunning Ladyboy Hooker Episode 61

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 44
14:12

Stunning Ladyboy Hooker Episode 44

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

Crossdresser enjoys a very painful flogging session in the d

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

Petite teen ladyboy gets fucked hard and painful

Shemale Korra Del Rio Painful Anal
05:23

Shemale Korra Del Rio Painful Anal

Stunning Ladyboy Hooker Episode 32
11:56

Stunning Ladyboy Hooker Episode 32

debbie heart tv whipping myself for my mistress
04:05

debbie heart tv whipping myself for my mistress

GREEN HIGH HEELS PAIN IN THEE ASS widely opened homo EXTREM wide ASS

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

Loud Asian Ladyboy Screaming with Pain from a Big Cock

Young shemale painfully anal fucked
11:26

Young shemale painfully anal fucked

Stunning Ladyboy Hooker Episode 14
10:21

Stunning Ladyboy Hooker Episode 14

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

Young shemale painfully anal fucked
11:52

Young shemale painfully anal fucked

Stunning Ladyboy Hooker Episode 22
11:10

Stunning Ladyboy Hooker Episode 22

Crossdresser enjoys a very painful flogging session
08:17

Crossdresser enjoys a very painful flogging session

Stunning Ladyboy Hooker Episode 20
11:24

Stunning Ladyboy Hooker Episode 20

Stunning Ladyboy Pounded Episode 10
09:38

Stunning Ladyboy Pounded Episode 10

Ebony assaultive banger rapes hard and painful blonde busty tran

Shemale Korra Del Rio Painful Anal
05:23

Shemale Korra Del Rio Painful Anal

Stunning Ladyboy Hooker Episode 26
11:23

Stunning Ladyboy Hooker Episode 26

Stunning Ladyboy Hooker Episode 16
10:57

Stunning Ladyboy Hooker Episode 16

Stunning Ladyboy Hooker Episode 60
10:49

Stunning Ladyboy Hooker Episode 60

CBT with Needles and Sounding
05:01

CBT with Needles and Sounding

Stunning Ladyboy Hooker Episode 4
08:32

Stunning Ladyboy Hooker Episode 4

Nipple torture pain for Tgirl
05:00

Nipple torture pain for Tgirl

Crossdresser Enjoys a very Painful Flogging Session in

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

Amateur tranny blowjob and danidaniels blowjob Karel is pain

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

Crossdresser enjoys a very painful flogging session in the dungeon

Stunning Ladyboy Hooker Episode 29
11:22

Stunning Ladyboy Hooker Episode 29

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

Emily tied up to ceiling on tiptoes and tortured by Erika

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

Stunning Ladyboy Hooker Episode 41
13:27

Stunning Ladyboy Hooker Episode 41

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

Hentai overwatch, halloween tranny anime, pain compilation

Stunning Ladyboy Hooker Episode 28
11:21

Stunning Ladyboy Hooker Episode 28

Stunning Ladyboy Hooker Episode 38
12:39

Stunning Ladyboy Hooker Episode 38

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

The Mistresses of pain are hungry for fresh meat. They

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 34
11:52

Stunning Ladyboy Hooker Episode 34

Stunning Ladyboy Hooker Episode 25
11:27

Stunning Ladyboy Hooker Episode 25

Shemale anal, shemale crying, shemale painful anal crying
26:42

Shemale anal, shemale crying, shemale painful anal crying

Ignore the shemale reaching out and screaming in pain and continue to fuck until she screams

Stunning Ladyboy Pounded Episode 9
09:51

Stunning Ladyboy Pounded Episode 9

Stunning Ladyboy Hooker Episode 19
11:03

Stunning Ladyboy Hooker Episode 19

Stunning Ladyboy Hooker Episode 62
15:29

Stunning Ladyboy Hooker Episode 62

Stunning Ladyboy Hooker Episode 6
09:50

Stunning Ladyboy Hooker Episode 6

Stunning Ladyboy Pounded Episode 7
09:48

Stunning Ladyboy Pounded Episode 7

Stunning Ladyboy Hooker Episode 15
10:29

Stunning Ladyboy Hooker Episode 15

Stunning Ladyboy Pounded Episode 12
09:51

Stunning Ladyboy Pounded Episode 12

Stunning Ladyboy Hooker Episode 24
11:34

Stunning Ladyboy Hooker Episode 24

Stunning Ladyboy Hooker Episode 13
10:37

Stunning Ladyboy Hooker Episode 13

Stunning Ladyboy Hooker Episode 46
14:54

Stunning Ladyboy Hooker Episode 46

Homemade anal fucking with argentinian girlfriend
28:46

Homemade anal fucking with argentinian girlfriend

Stunning Ladyboy Hooker Episode 64
04:00

Stunning Ladyboy Hooker Episode 64

Stunning Ladyboy Hooker Episode 47
15:19

Stunning Ladyboy Hooker Episode 47

Skinny Blonde Tranny Loves Pain and Pleasure
09:07

Skinny Blonde Tranny Loves Pain and Pleasure

Young shemale painfully anal fucked
21:47

Young shemale painfully anal fucked

Stunning Ladyboy Hooker Episode 45
14:36

Stunning Ladyboy Hooker Episode 45