Jizz

Don't you think that had to hurt?

ass

That had to hurt

AnythingGoesUltimate

G(f) said it was hurting so I had to pull out and cum.

gonewild

Anyone ever seen a tattoo like the girl on the left? That had to hurt!

Hotchickswithtattoos

Some of those had to hurt

Hotchickswithtattoos

You really hurt my (f)eelings last time I posted.. Had to delete. Hopefully this post will be better..

gonewild

You asked for it Grant (This hurt to make but I had to fulfill my duty, I'm so sorry.)

gamegrumps

Was watching some porn when....that had to hurt!

funny

I hurt myself on Friday, so all I had to do this weekend was take naked (f)otos in the bath.

gonewild

[NSFW] Anon account. First time poster, long time lurker. Say what you want. I deserve it. I'm fat and gross. I have a cyst I can't even bend over to see. I had to take a picture to find out why it hurt so much. Ugh...

popping

This seriously had to have hurt [NSFW]

cringepics

That had to hurt

funny

That had to have hurt that mango a little bit

mylittlemango

Had a MFM last night, one of my friends played really hard with my nipples and they still hurt. Kiss and make them better? Feel free to PM me your pain relief suggestions...

gonewildcurvy

Hurt my knee and had to go get an X-ray

funny

Alexa used every opportunity to hurt me when her older sister wasn't around, she had every right to as the sister of my owner

Femdom

Finally received my new internally spiked chastity cage, had to put it on ASAP. Gosh it hurts but I love it.

chastity

This had to hurt

ImGoingToHellForThis, gifs

Can anyone tell me what this thing is? Sorry if wrong Sub, I'm just at a loss, I thought maybe a fissure? Doesn't seem to be a hemorrhoid, but I've never had either, it just hurts when I poop, had it for like 2 days and it's hurting less, yesterday was fi

shittingadvice

(M)new HERE but been lurking trust me I didn't forget about you beautiful ladies it's just I'm going through it right now??????????? I had to leave and be with my mom I so fucking hurt right now

gonewild

This had to hurt

WTF

that HAD to hurt

noisygifs, instant_regret, yesyesyesyesno, gifsthatendtoosoon

I was bad. Hubby had to punish me. He says it hurts him more than it hurts me, but I'm not so sure...

RoxyG_MVP, 40plusGoneWild, u_Bolshoibear, 50plusGW

Sel[f] latex shoot in stocks, my feet hurt so much from the pony wedges I had to take them off!

ShinyPorn

Sel[f] post, my feet hurt so much from the pony heels I had to take them off!

bdsm

Had to plug and spank myself. It hurts, but I guess it's necessary for becoming a better sissy. Make me your bitch?

FemdomHumiliation

[38F] My legs hurt. May I take a seat? (Sorry, I had to repost)

gonewild30plus, gonewild

As requested!....not one but two! I saw another girl do this and had to try it!!... and yes my ass hurt :)) xx!!![?][t]

AnalGW

I had to catch a flight a day or so after receiving this beating and my poor butt hurt the whole way ? [TW]

BDSMGW

I had to get ingrown nail surgery yesterday and it hurts...

WTF

"I beat up the last guy so badly, he had to be carried out on a stretcher and begged me to stop hurting him."

SkylarSnow, chubby, SlimandStacked, AmazingCurves, PornstarsHD

"I beat him up so badly, he had to be carried out on a stretcher and begged me to stop hurting him."

EmilyAddison

"I beat up the last guy so badly, he had to be carried out on a stretcher and begged me to stop hurting him."

MiaMalkova

"I beat him up so badly, he had to be carried out on a stretcher and begged me to stop hurting him."

SkyeBlue

"I beat him up so badly, he had to be carried out on a stretcher and begged me to stop hurting him."

Desiree_Dulce

"I beat him up so badly he had to be carried out on a stretcher and begged me to stop hurting him."

AlettaOcean

It's been a while since I had a pain slave, I want you to pay me to hurt you. The more extreme the better. Kik me Sellingmysoul2u

findomfinder

Dayumn that had to hurt

u_htoadjc

That had to hurt NSFW

WTF

NSFW - Friend of a friend was cutting flooring with a stanley knife and slipped. This is the definition of had to hurt. And yes he's alright.

HadToHurt

Well that had to hurt.

Memes_Of_The_Dank

I have been so horny since my daddy with benefits had to quarantine and my gf rejected me 3x this week saying Im “too sexual”. So i neds attention who would fuck and hurt me ???

Slut

It's still super cold here in Texas, but it had been too long since I'd been naked and my clothes were starting to hurt.

GaybrosGoneWild

Rant I had to throw out. I've heard numerous people say this and it's always white straight dudes. Yes, I agree that there are plenty dark jokes with no hurtful intentions, where there is no point in getting upset. But pretending like it's always the targ

u_MustacheOfGold

First attempt at guro content- that had to hurt

guro

The gravel on the side of the road would have hurt my feet after a while so I had to make a decision

Bbwcaptions