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Painful Toying Anal Porn Videos

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02:20
116 min degrading of bdsm sissy pain whore Alina
alinanightsky

47.7K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

114.6K views
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02:05
Compilation with Weekly Episodes from the pain whore Alina
alinanightsky

31.4K views
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16:17
some fun kitty playtime
Kittykisses96

4.2K views
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01:34
A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
alinanightsky

18.6K views
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08:37
Black blow up spiked butt plug for my S&M Daddies!
Victoria Lecherri

25.5K views
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14:26
Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
Denise Humain

21.9K views

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14:21
Another weekend - Same result, nipples hurt, asshole is destroyed, still i wish i dont had to do it by myself.
Denise Humain

6.4K views
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10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
TheToxicTwins

31.9K views
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51:35
Pain and Pleasure

85K views
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09:57
Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo

25.2K views
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10:55
Kylie's prediciment
Kylie Lynn

10.4K views
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01:29
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MissRose TS

13.7K views
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08:24
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5.6K views
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10:12
Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose
Lilith_Eclipse

17.3K views
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01:28
First try for new plug and a bit bigger
Sanne

5.5K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

8.4K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

9.8K views
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05:41
Sadistic vampire Mistress
Jazebel

3.1K views
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07:34
BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
Denise Humain

700 views
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06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku

5K views
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06:31
last week some long awaited toys finally arrive and i was eager to test them out part II

3.7K views
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18:03
A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator
MyLolaTrav

4.8K views
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02:33
Hot Crossdresser fucks herself with a massive homemade toy!!
Dope Slut

1.4K views
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10:49
Rebecca's painful Orgasm
Rebeccafuxx

6.6K views
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06:36
Morning Procedures - bathing in sheer lingerie and painful anal stretching
Chantal Fouet

3.9K views
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02:47
Preview Video for Maledoms wanna see my Sissy Skills. Sexy Deepthroat Blowjob and extreme Ass gaping pussy.
Denise Humain

3.4K views
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02:50
Tabasco Dildo Punishment for forgetting my butt plug today...
Sissy-Hinata

1.8K views
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08:00
BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
Denise Humain

500 views
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10:23
second try on triple penetration toy

1.6K views
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03:37
Electro Plug slips all the way in
Anyankah Renee Athanasia

4.7K views
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22:12
Rebeccas Maso Perversions
Rebeccafuxx

9.4K views
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23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain

5.2K views
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10:18
Little sluts bills punishment
Lizz_ss25

4.7K views
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06:08
Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro
MyLolaTrav

3.3K views
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08:27
try a new triple penetration toy

1.8K views
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07:35
third try with triple penetration toy

2.8K views
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05:23
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3.5K views
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02:16
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
Denise Humain

2K views
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35:14
Transsexual
MIMEROMOLE

1.8K views
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06:57
Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
Dope Slut

1.3K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

6.2K views
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01:37
CdTina painful anal

2.6K views
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00:40
Tight Ass Shemale Reign Swallow 12 Inch BBC Deep Up Her Ass
Soloregin

2.4K views
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08:03
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
Denise Humain

2.3K views
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05:11
Masochistic tranny whips himself with flogger

1.5K views
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02:33
Spanking myself a bit!
Bambi Christa

2.9K views