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Sissy Painful Anal Porn Videos

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01:33
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111.8K views
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09:57
Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo

24.1K views
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06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku

4.6K views
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10:53
The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
alinanightsky

73.2K views
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02:20
116 min degrading of bdsm sissy pain whore Alina
alinanightsky

34.5K views
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02:05
Compilation with Weekly Episodes from the pain whore Alina
alinanightsky

24.3K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

106K views
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06:08
Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
Candy Ass Sissy

31.8K 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

13.1K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

59.2K views
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08:37
Black blow up spiked butt plug for my S&M Daddies!
Victoria Lecherri

22.4K views
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03:04
25 min of abuse and hard use for the pain whore Alina
alinanightsky

4K views
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17:38
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Derek6699

51.4K 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

19.5K views
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03:26
Kill that sweet butthole with a Dildo
Charlotte Wilde

5.4K views
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10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
TheToxicTwins

30.6K views
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11:32
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Sissy Cindy Slut

6.4K views
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01:28
First try for new plug and a bit bigger
Sanne

5.1K 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

5.2K views
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29:58
Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16
LaRicura16

5.5K views
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05:55
Ass-to-Mouth Painful Sissy Bareback Fuck in Motel

29.7K views
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08:24
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5.1K views
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10:55
Kylie's prediciment
K Kylie Lynn

10K views
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01:29
MissRose TS -Preview BBC GIANT XXXL Dildo Painal Moan Outdoors - Shemale Got Caught Anal Stretching - Big Cock Pumping M
MissRose TS

13K 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

16.3K views
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01:32
No pain no sissy gain
Kittykisses96

2.6K 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

4.3K views
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10:23
second try on triple penetration toy

1.4K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

9.3K 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

3.4K views
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05:41
Sadistic vampire Mistress
Jazebel

2.4K views
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00:57
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Sasha Earth

7.8K views
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05:24
MissRose TS - Rosanna IN pRIVATE - WILD SHEMALE pAinal MASTURBATION - Rough ASSPLAY Big SHECOCK - cumshot
MissRose TS

2.3K 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

3.2K views
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07:35
third try with triple penetration toy

2.4K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

5.8K views
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08:27
try a new triple penetration toy

1.7K views
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01:04
Up Close Painful Femboy Dildo Practice
Khatara Shikiku

2.8K 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

2.9K views
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03:41
The Pressure of Pain and Punishment
BadGod

3.3K views
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03:37
Electro Plug slips all the way in
Anyankah Renee Athanasia

4.5K views
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10:49
Rebecca's painful Orgasm
Rebeccafuxx

6.2K views
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02:02
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 2 - 4
Denise Humain

3.2K views
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23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain

4.8K views
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08:45
Beautiful sissy pleasures herself with nipple clamps, nettles and a dildo, then makes herself cum with her vibrator
MyLolaTrav

1.5K views
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05:00
Sweet Anal Pain for Solo Sissy CD
Regina Blasegern

9.1K views
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10:18
Little sluts bills punishment
Lizz_ss25

4.3K views