8 XXX : the pain

Mondays are such a pain in the ass [M+F] (xpost from gw)

imgur.com category @HotCPL88

Her legs just keep spreading, it's painful to watch (fixed)

imgur.com category @nomise

Fishnets and then pain

imgur.com category @Addicted_to_reddit69

She feels an extremely sharp pain in her anus

imgur.com category @shitwinker77

Fishnets and Pain [x-post from /r/MasterOfAnal]

imgur.com category @HobbyDaily

A pain in her ass

imgur.com category @gcinv

Looks Painful

imgur.com category @Kinda_Crazay

This seems to be painful

imgur.com category @gcinv

Nice, tight and painful.

tumblr.com category @Kalamity_

Packing to see my kinky girlfriend who loves painful anal as much as I do. We are celebrating Easter OUR way.

imgur.com category @naughty_girl

Closed eyes, pained expression, Butt plug in the mouth, all it needs is a source. Could you find it?

gfycat.com category @SauerkrautGod

A little pain never hurt

imgur.com category @ItsAnotherOP

Girl with striped socks is pain

tumblr.com category @Kalamity_

That Sweet Pain

imgur.com category @calbertson81

Another night shift presentation....(f)eaturing.....your nurse with pain med and this...

imgur.com category @Tatted_up_A1

BF wanted me smooth. Gosh, that was painful. But I love the result. Do you?

imgur.com category @derpyFnatic

Bring me pain, bring me pleasure

tumblr.com category @[deleted]

Giving my little sister pain in the ass

imgur.com category @NastyPlace

Not sure if she's screaming from pleasure or pain (r/NSFW_GIF)

imgur.com category @Eekthekat

Enjoyable Pain

imgur.com category @sooflyy

Is she in pain or pleasure?

imgur.com category @SeaFun2

Sasha Pain

imgur.com category @NOT_MEEHAN

It's Worth a Little Pain

gfycat.com category @Kinda_Crazay

That actually looks painful.

imgur.com category @skyrimsmut

Detention can be a real pain in the ass!

imgur.com category @sothisshit

It's Worth a Little Pain

gfycat.com category @Kinda_Crazay

I love the good pain!

gfycat.com category @felicialovesponch

A Little Painful

gfycat.com category @Kinda_Crazay

The most painful fun I have ever experienced. PM's are welcomed ;)

imgur.com category @chastitybitch

No Pain No Gain by Powfoo [MM] (Tay arc part 3)

imgur.com category @AThinker2

Pain for nipples, pleasure for the pussy

tumblr.com category @Myphoneacco

Kim, Loving Pain

gfycat.com category @Soundwalk

A Little Painful

gfycat.com category @Kinda_Crazay

The Bitter, Sweet and Painful Thorn - By: Gentsuki

imgur.com category @TheGamingGeneral

The good kind of pain

imgur.com category @iBXxPwninxX

Pain and pleasure. Happy to return the favor- up her ass!

imgur.com category @Motomonkey16

The Thin Line Between Pain and Pleasure

imgur.com category @Bobs_porn_alt

Pain for the pussy

tumblr.com category @Myphoneacco

Pain for the pussy

tumblr.com category @Myphoneacco

The Feminist prisoner falsely believed that after a long hard day of continuous painful abuse, she could finally sink into a nice hot bath, and soothe her sore bruised body. But her cruel Master insists on another spanking before release.

tumblr.com category @antifemz

The first step to becoming her sissy bitch is through pain.

imgur.com category @PornMaker2048

"Painful anal and cream" was actually "regular sex and cream". Found the image and put on imgur for anyone who actually wanted to see it

imgur.com category @Capitan_Hammer

Sirswantslittle pain is always good

tumblr.com category @havoc_bot

After many months of painful strict training and sleeping in small dirty pen cell, i feel the fear and trembling upon...

tumblr.com category @havoc_bot

"Overwhelming Tryouts" - [Ashley Adams vs. Brett Savage] (Scene: Ashley Persuades The Coach / Site: The Real Workout)

gfycat.com category @shawnyshawnyNoMi

The face of pleasure and pain

tumblr.com category @wake_winkle_wupmole

No Pain No GPA Gain - Makayla Cox - Vienna Black

gfycat.com category @delman74

Vina Sky "Pain and Gain"

gfycat.com category @Jade____

The difference is painfully clear, sissy

gfycat.com category @MistressStella

'The Lady in Red' in Pain

imgur.com category @Saweb1234