126.1K Results

Painful Anal Sex Porn Videos

Free Porn Videos

Not available in United States

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

23.7K views
Not available in United States

01:33
fucking my femboy slave sissy slut painful anal

110.6K views
Not available in United States

06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku

4.4K views
Not available in United States

04:04
Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass
HatanoMiwa

59.2K views
Not available in United States

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

54.6K views
Not available in United States

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

557.6K views
Not available in United States

51:35
Pain and Pleasure

83.7K views
Not available in United States

18:18
Anal fist fuck faggot love to feel the pain in the ass
Nicole Montero

111.3K views
Not available in United States

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

79.9K views
Not available in United States

07:10
Redhead Asian shemale all covered in pain gets fucked
Extreme Ladyboys

41.6K views
Not available in United States

02:46
Daddy domination over his sissy sex slave and to taught her that my place is under his balls
alinanightsky

22.5K views
Not available in United States

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

21.4K views
Not available in United States

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

26.6K views
Not available in United States

06:06
My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
Nathalia Fontes

67.2K views
Not available in United States

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

18.3K views
Not available in United States

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

5.6K views
Not available in United States

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

30K views
Not available in United States

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

18.7K views
Not available in United States

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

19.4K views
Not available in United States

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

30.2K views
Not available in United States

10:55
Kylie's prediciment
K Kylie Lynn

9.8K views
Not available in United States

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

123.1K views
Not available in United States

02:17
Boss tranny show him his painful role
XXL4XXL

28.2K views
Not available in United States

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

27.3K views
Not available in United States

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

29.5K views
Not available in United States

10:15
Linday Purple Pain

9.1K views
Not available in United States

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

10.3K views
Not available in United States

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

7.4K views
Not available in United States

22:12
Rebeccas Maso Perversions
Rebeccafuxx

8.9K views
Not available in United States

03:30
Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
HatanoMiwa

288.4K views
Not available in United States

00:37
TS_ScarlettRose struggles to take it!
forsakinsin

9.1K views
Not available in United States

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

42.7K views
Not available in United States

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

12.8K views
Not available in United States

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

4.8K views
Not available in United States

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

5.1K views
Not available in United States

10:18
Little sluts bills punishment
Lizz_ss25

4.1K views
Not available in United States

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

4.6K views
Not available in United States

05:23
Bdsm tranny heavy impact play ftm Flogging
Keeno666

3K views
Not available in United States

05:11
Masochistic tranny whips himself with flogger
Keeno666

1.3K views
Not available in United States

08:19
Linday Loves Pain

5.4K views
Not available in United States

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

3.1K views
Not available in United States

03:41
The Pressure of Pain and Punishment
BadGod

3.2K views
Not available in United States

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

3.2K views
Not available in United States

05:41
Sadistic vampire Mistress
Jazebel

2.2K views
Not available in United States

10:24
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 4 - 4
Denise Humain

3.5K views
Not available in United States

17:28
Denise Humain Scene Mix (Anal, Nipple, Blowjob)
Denise Humain

1.9K views
Not available in United States

02:16
Alone and Horny nipple pain and anal stretching sexy Sissy Whore - Part 1 - 4
Denise Humain

1.9K views