Most Favourited Videos Tagged with painful anal

doggie style anal

anal slut

bubble butt anal

anal creampie

18 anal

bareback anal

teen anal

hard anal

blonde anal

amateur anal

anal

extreme anal gape

analgape

anal sex

analsex

analingus

chubby anal

rough anal

brunette anal

anal orgasm

first time anal

milf anal

anala

anal riding

real anal

1:09

First Time Putting my Bull’s Huge Cock in my Slutty Ass while Husband Films - PAIN...

126.5k views
mits

12:11

Skinny blonde Jenny get painful anal and first time anal riding

383.8k views
Ziploc

14:00

First time painful anal | painal

91.1k views
kungjew77

17:16

Painful Ass to Mouth | Painal | Anal Destruction

797.1k views
mits

1:21

MILF Takes a Hard Ass Fucking for being Bad PAINAL

4.7m views
mits

12:41

Painal "it Hurts! please Cum, i'll do Anything!"

1.4m views
mits

12:49

Hooker Screaming in Pain but still allow to Fuck her Ass. Painful Anal.

2.3m views
mits

32:03

Painal "it Hurts so Bad! please Cum i'll do Anything, PLEASE!"

227.6k views
mits

7:54

"IT HURTS! PLEASE CUM!"

83.1k views
mits

1:55

Pain all 11" Dildo up in her Ass, Screams and Cry a Lot

548.9k views
mits

10:05

My first Time Anal

2.0m views
mits

1:56

NO MERCY PAINAL | Extremely Tight Ass Hole Gets Fucked while she Cries

235.4k views
mits

10:47

Innocent Girl Gets her Tight Ass - Painal

568.7k views
mits

5:22

First anal crying in pain

664.3k views
stooka

1:31

WTF... please Stop Fucking my Ass it Hurts!

62.8k views
mits

1:26

Painful Anal (I Cried Lol) it's my Fault I was on my Period.

278.1k views
mits

37:30

Lina- Natural.Big Titis - First Time Anal With Fat Dick

3.5k views
shadow666

7:53

EXTREMELY PAINFUL ANAL SEX - ANAL ORGASM & CREAMPIE

1.9m views
mits

8:52

Latina Brunette with Big Ass does her first ANAL! Amatér (POV Creampie)

570.3k views
Stylus

10:10

Painal Creampie - she Hates Anal but yet here we are

548.2k views
mits

12:34

AMAZING First Time ANAL With Brazilian Babe

670.2k views
SasquatchHunter

10:41

ANAL HAMMER TIME! She Struggles While He Pounds Her Jiggling Ass Faster CIM

4.0m views
Stylus

0:55

Tight Ass Amateur girlfriends gets painful anal. She screams and kicks boyfriend

4k views
shadow666

1:16

What what Cumming in her Butt

47.6k views
mits

4:06

Anal Slave PAWG Begs for Cum inside her little Teen Asshole

17.7k views
mits

5:19

Tied up Flogged Fucked and Finally PAINAL

73.9k views
mits

8:21

Страстный анальный секс

1.0m views
mits

4:03

Ebony Babe Wicked Sadie’s first Anal Video PAINAL

980k views
Stylus

8:26

Elle Est Accro à ANAL SEXE

589.1k views
mits

10:18

Casting Couch Painal for Amateur Desiree

800.3k views
mits

8:56

Fucking my ASS - third Time ANAL still not a Charm

703.8k views
mits

1:59

Fucked in the Ass with my Thongs Slid to the Side

197.8k views
mits

Back
First
1
2
3
Last
Next

Best Free painful anal Porn on Shooshtime

Love painful anal porn? You have come to the right place. We feature 77 of the best painful anal videos you will ever see on the internet. All our porn videos are free to watch, with no registration required, however we always suggest registering as you will be able to take advantage of all the cool features Shooshtime has to offer! Have some of your own painful anal videos you would love to share? Feel free to upload them and tag this page!