Jizz

The Lovely Scarlett Pain

Great_Cumshot_Pics

The less-painful version of having your tongue frozen to a flagpole. Much more delightful for all concerned.

Bondage

The instant of pain

PerfectTiming

The good kind of pain

nsfwhardcore, anal, O_Faces

Paine, from Final Fantasy X-2 (anyone know the source?)

rule34

The girls are being reluctant to come out and play today. Just had surgery on my mouth and in a lotta pain due to complications so I won't be on too much... have [F]un

gonewildcurvy

The only painful thing to a woman is having to marry an inferior man.

maledom

The almighty Fuck [pain x ino]

Naruto_Hentai

Pain in the ass(hole)

IntenseBDSM

The PJ's Match (Sasha Pain)

UnrealGirls, gtsim

The lesser female brain can't get porn industry isn't about Male misogyny but female hypergamy. This porn scene isn't meaning Men are misogynous and mistreat women; it means women are hypergamous and need superior Men. Female watchers enjoy this painful a

maledom

Pain in the ass!

fuckellenpao

The good pain

bdsm

The long slow thuds sounded painful

cuckoldcaptions

The most painful torture known to mankind.

ecchi

The point where pleasure turns into pain

guro

The good kinda pain

BlackIsBetter

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

chastity

The good kind of pain

keyholdercaptions

Pain in the ear

nsfwoutfits

Pain in the news

PantiesToTheSide

The gut pain will pass, child

FearMe

the aswer correct is: yes Sir ...trust, pain and pleasure (f)

gonewild

The smiles look painful, and she got a smirk going

BreastEnvy, Bigtitssmalltits

the good kind of pain

GoneWildTrans

The Thin Line Between Pain and Pleasure

BDSM_Artwork

Pain in the Ashe Part 2 (RaunchyNinja)

Overwatch_Porn, Rule34Overwatch, OverwatchNSFW

the very worst of my hands during contamination ocd, a painful memory

OCD

Pain in the ass.

Tgirls, sloppyGW

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

broslikeus, u_jebac995

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

broslikeus

The Kingpin of Pain

Stoyaxxx

The fine line between pleasure and pain

broslikeus

The fine line between pleasure and pain

TotallyStraight, u_tannernsfw0842

The second one doesn't look like it was very painful for him...

goingtohellforthis

The fine line between pleasure and pain

broslikeus, TotallyStraight, gaynsfw

Pain and pleasure at the same time

forcedorgasms

The Queen of Pain in control [Dota 2] (BlindWildcat)

rule34

The back pain!

nobra

the sexiest way to develop chronic back pain...

HugeHangers, OnlyFansBrunette, u_Necropath6969

The bitch yearning for pain

guro

The pleasure and pain

Ladyboys

The crotchrope had gone from stimulating to painful and there was no end in sight

Bondage

The Face of Pain # 512

FaceofPain

Pain in the Back [Original]

animeshorts, animetanktops

Pain in the ass to put on, but worth it

tightsqueeze, VerticalGifs, bigasses, iwanttobeagirl, cuteassesinjeans, tightdresses

Pain is the best teacher...

femdomcaptions