148.8K Results

Homemade Painful Porn Videos

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51:35
Pain and Pleasure

84.5K views
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01:28
First try for new plug and a bit bigger
Sanne

5.4K views
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07:02
Mistress Cy IPL Hair Removal Punishment
Cyanide Mistress Of Darkness

11.3K views
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01:24
electric sex and painful end.

37.4K views
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14:55
Sissy Maid - Pain & Pleasure Bondage
Derek6699

10.3K views
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10:27
Vampire Roleplay Compilation Video - Cyanide Absorbs Synnz' Aura
Cyanide Mistress Of Darkness

17.2K views
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04:08
dumb slut gets the belt for cumming without permission
Bambi Christa

7.6K 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

17K views
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00:37
TS_ScarlettRose struggles to take it!
forsakinsin

9.6K views
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01:23
Labor Pains

19.5K views
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02:13
Pain free Kitty Kaiti..mega load

84.5K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

8.1K views
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04:12
Selfuking
Papiricoo

30.3K views
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03:41
The Pressure of Pain and Punishment
BadGod

3.6K views
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11:13
pain, pleasure & cum load for T-girl Alexandra

123.6K views
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01:32
No pain no sissy gain
Kittykisses96

2.8K views
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06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku

4.8K views
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08:00
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Vulva Cock Jez

9.9K views
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05:41
Sadistic vampire Mistress
Jazebel

2.8K views
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05:37
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Jazebel

2.6K views
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10:07
Domination and pain with this 2 shemales hardcore punishment
Latina Tranny

27.7K views
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08:49
Sissy with nipple clamps ties up her cock and makes herself cum hard with the vibrator
MyLolaTrav

5.2K views
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10:23
second try on triple penetration toy

1.5K views
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05:10
FtM boy punished for being lazy
BonusholeToy

2.8K views
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05:00
Sweet Anal Pain for Solo Sissy CD
Regina Blasegern

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

3.6K views
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03:41
Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
Cyanide Mistress Of Darkness

7.6K views
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18:44
young enby does wax play and anal for a vampire
kit69lupin

252 views
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01:14
Tyche_Toxic Winces In Pain During Self CBT
Tyche Toxic

4K views
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06:36
Morning Procedures - bathing in sheer lingerie and painful anal stretching
Chantal Fouet

3.8K views
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09:18
Nipple clamped shemale tied up with ropes and chains is vibred and cums twice
MyLolaTrav

9.8K views
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06:54
Get ready for pain and submission little Sissy Slave.
Denise Humain

8.3K views
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23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain

5.1K views
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03:37
Electro Plug slips all the way in
Anyankah Renee Athanasia

4.6K views
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03:43
Femboy slut gets hard ass spanking as punishment (SissySandyy20 Solo)
Sissy Sandy

5.1K views
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11:37
Beautiful sissy gets naked, puts clamps on her nipples, jerks off her big cock with nettles and makes herself cum hard
MyLolaTrav

5.6K views
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04:02
so much pain

13.8K views
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02:03
Clamping my nipples and clit, masochism

3.9K views
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02:50
Tabasco Dildo Punishment for forgetting my butt plug today...
Sissy-Hinata

1.7K views
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30:01
(P.4-5) Athena 50 Shades of FUCKED UP TATTOO BDSM XXX 666
Cyanide Mistress Of Darkness

7.2K views
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01:31
Linda Asian Ts Champagne Cleaning And Pain With Big Dildo
Lindaasian-ts

16.2K views
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00:26
Mistress and pain slut

22.8K views
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04:15
Hot Wax On Sissy Cock

3.1K views
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02:49
sissy slut punishing herself with a paddle
Emma Huntcock

2.5K 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

3.1K views
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03:02
Fat Sissy light ball torture and wax play in chastity
Chubby Sissy Dani

3.1K views
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01:04
Up Close Painful Femboy Dildo Practice
Khatara Shikiku

2.9K views