49.7K Results

Sissy Pain Porn Videos

Free Porn Videos

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

23.8K views
Not available in United States

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

14.4K 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

6.2K views
Not available in United States

01:17
Daddy Loving Sissy Pain Slut Whipping
JessicaLynn15

4.7K views
Not available in United States

01:11
Gay Fat Asian Sissy Pain Slut Dancing
JessicaLynn15

11.8K views
Not available in United States

00:27
Belted sissy pain-slut

16K views
Not available in United States

18:29
Just because I can..
Twistedrama

76.8K views
Not available in United States

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

98.7K views
Not available in United States

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

73.6K views
Not available in United States

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

54.5K views
Not available in United States

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

19.7K views
Not available in United States

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

35K 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

8.7K views
Not available in United States

03:14
Pleasure Pain Sissy

36.8K views
Not available in United States

03:23
FtM bonus Toy : 100 cunt slaps
BonusholeToy

16.1K views
Not available in United States

04:08
Balls stretched masturbation
MyLolaTrav

18.7K views
Not available in United States

09:59
How to torture a beautiful sissy cock
MyLolaTrav

18.7K views
Not available in United States

01:14
pain turns me on
boobyb0y

74.8K views
Not available in United States

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

49.3K views
Not available in United States

04:56
Caning and choking Kitsy
Kitsy Meow

47.9K views
Not available in United States

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

4.7K views
Not available in United States

08:01
Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons
Linzy19

33.4K views
Not available in United States

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

5.3K views
Not available in United States

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

29.5K views
Not available in United States

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

20K views
Not available in United States

11:32
Sissy faggot bitch
Sissy Cindy Slut

5.7K views
Not available in United States

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

8.4K views
Not available in United States

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

43.5K views
Not available in United States

14:42
Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
Denise Humain

12.7K views
Not available in United States

00:43
Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!
Allmylinks

27.7K 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

17.7K views
Not available in United States

07:35
third try with triple penetration toy

2.1K views
Not available in United States

10:22
Maso Slave Rebecca
Rebeccafuxx

5.4K views
Not available in United States

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

12.1K views
Not available in United States

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

25.5K views
Not available in United States

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

9.7K 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

28.4K views
Not available in United States

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

4.8K views
Not available in United States

10:55
Kylie's prediciment
K Kylie Lynn

9.7K views
Not available in United States

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

23.2K views
Not available in United States

10:12
Transgender Slut Lilith Eclipse Fisting Herself and Playing With Her Asshole in a tiny Chastity Cage and Dark Pantyhose

15.6K views
Not available in United States

17:40
Icy Hot Wooden Pony Self Bondage Torture
Derek6699

16.4K views
Not available in United States

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

29.3K views
Not available in United States

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

15.4K views
Not available in United States

02:46
Becca squirts in shiny pantyhose
Rebeccafuxx

2.8K views
Not available in United States

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

16K views
Not available in United States

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

2.8K views