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Bondage Anal Pain Porn Videos

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36:28
Pain Slut Kira
Twistedrama

20.6K views
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16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow

83.1K views
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18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699

45K views
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08:09
Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
Kitsy Meow

55K views
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17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699

44.5K views
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01:29:00
Synnz & Mistress Cy "50 Shades of Fucked Up" Shemale Tattoo BDSM Kink Fuck Session (FULL RELEASE)
Cyanide Mistress Of Darkness

15.7K views
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44:19
Denise Humain works on her Asshole for 45 Minutes straight and to the limit.
Denise Humain

4.5K views
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03:41
Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
Cyanide Mistress Of Darkness

6.7K views
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17:02
Thick Anal Viring Gets Her 1st Time Very PAinful & Begging

40.1K 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

3.1K views
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08:03
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 3 - 4
Denise Humain

1.6K views
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18:29
Just because I can..
Twistedrama

61K views
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11:41
How to Give Pain and Pleasure to a Big Sissy Cock
MyLolaTrav

31.2K views
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09:59
How to torture a beautiful sissy cock
MyLolaTrav

16.2K views
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01:14
pain turns me on
boobyb0y

66.7K views
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10:29
How a Tgirl severely punishs her big cock.
MyLolaTrav

16.7K views
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25:04
Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
Derek6699

5.7K views
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10:01
Working on Sissy Slave Denise Humain Nipples for hours Part 1
Denise Humain

38.5K views
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13:59
Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
Denise Humain

6.7K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

23.5K views
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17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

15K views
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08:09
Urethral sounding and vibration of a caged and bound shemale
MyLolaTrav

15.1K views
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07:53
Sissy Maids Punishment
Derek6699

13.4K views
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16:11
A beautiful transgender with nipples clamped has his big cock electro-stimulated until it drips long
MyLolaTrav

8.1K views
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01:36
Ronni Endures Breast + Nipple Pain by PA Bondage 1-25-2019

22.2K views
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09:18
Nipple clamped shemale tied up with ropes and chains is vibred and cums twice
MyLolaTrav

8.7K views
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08:49
Sissy with nipple clamps ties up her cock and makes herself cum hard with the vibrator
MyLolaTrav

4.2K views
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02:03
Clamping my nipples and clit, masochism
Keeno666

3.5K views
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14:55
Sissy Maid - Pain & Pleasure Bondage
Derek6699

7.9K views
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05:57
DRIPPING HOT WAX ON MY COCK
Kenzie Star

2.6K views
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05:23
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Keeno666

2.3K views
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05:37
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Jazebel

1.5K views
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08:15
A sexy Sissy ties her big cock with a rope and gives her pain with nettles before cuming
MyLolaTrav

2.7K views
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01:19
Dizzy Miss Sizzy In Painful Bondage

5.7K views
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17:10
Deepthroat Blowjob Training and Wax on Tits and Nipples
Denise Humain

3.5K views
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00:29
Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
iFetFuc

1.6K views
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00:20
Sissy training Extreme CBT electric shock cock pain bdsm
iFetFuc

6.7K views
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00:20
CD in pain...

2.5K views
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05:00
Sweet Anal Pain for Solo Sissy CD
Regina Blasegern

8.5K views
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00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth

6.5K 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

1K views
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07:53
Painting tranny

341.3K views
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01:15:03
Pain and Pleasure Part 2

175K views
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02:37
DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM

140.8K views
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51:35
Pain and Pleasure

79.9K views
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31:02
HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-

62K views
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01:48
1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR

518.6K views