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07:53
Sissy Maids Punishment
Derek6699

16.6K views
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23:29
Sissy Maid Icy Hot Wooden Pony Punishment 2
Derek6699

26.4K views
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28:23
A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
Denise Humain

1.9K views
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25:04
Sissy Maid Collared to Bedpost in Spiked Chastity Cage and Handcuffed Harness Gagged
Derek6699

9.5K views
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02:06
Sissy Nipple Cow Chastity Nipple Pump Electro Pain
Titten-Sau

16.1K views
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51:35
Pain and pleasure, chastity and lust, Part 1

105.9K views
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51:35
Pain and Pleasure

83.9K 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

19.1K views
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17:02
Thick Anal Viring Gets Her 1st Time Very PAinful & Begging

43K views
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11:32
Sissy faggot bitch
Sissy Cindy Slut

6.3K views
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10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
TheToxicTwins

30.4K views
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03:26
Kill that sweet butthole with a Dildo
Charlotte Wilde

5.3K views
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04:02
Finishing up with pain on my balls
Naomi Perv

2.7K 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

10.6K 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

18.5K views
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17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.9K views
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01:17
Daddy Loving Sissy Pain Slut Whipping
JessicaLynn15

5K views
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00:20
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iFetFuc

28.4K views
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01:28
First try for new plug and a bit bigger
Sanne

5K views
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09:09
3 dildos, a crop, clothspins and a horny girl on a bed
Bambi Christa

9.2K views
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01:11
Gay Fat Asian Sissy Pain Slut Dancing
JessicaLynn15

12.2K 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

5.3K 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

5K views
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05:55
Ass-to-Mouth Painful Sissy Bareback Fuck in Motel

29.6K views
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08:24
got a new toy with electro shock and vibrating function

5.1K views
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10:27
Vampire Roleplay Compilation Video - Cyanide Absorbs Synnz' Aura
Cyanide Mistress Of Darkness

16.4K views
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09:57
Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo

23.9K views
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00:27
Belted sissy pain-slut

19.5K views
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04:12
Selfuking
Papiricoo

29.6K views
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08:09
Urethral sounding and vibration of a caged and bound shemale
MyLolaTrav

16.4K views
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04:08
Balls stretched masturbation
MyLolaTrav

19.2K views
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04:08
dumb slut gets the belt for cumming without permission
Bambi Christa

7.1K views
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10:55
Kylie's prediciment
K Kylie Lynn

9.9K views
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18:35
Kisses and pain in intimity

19K 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

12.9K views
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14:55
Sissy Maid - Pain & Pleasure Bondage
Derek6699

9.6K views
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00:46
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35.3K views
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01:18
Sissy slut in pain
SissyPropertyUk

8.7K 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

16.1K views
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01:32
No pain no sissy gain
Kittykisses96

2.6K views
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05:46
Nipple Play Found Object FTM Hairy Tit Smacking
Lyla Switch

3.3K views
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02:13
Pain free Kitty Kaiti..mega load

84.4K views
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07:05
Candle Wax & Chastity Go Together like PB & Jelly
MJ

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

3.3K 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

4.2K 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

3.1K views
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30:28
I need the pain in my ass

260.3K views

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