Jizz

"I'm so sexy...it hurts!" - Yeah, I bet it does.

NSFW_GIF

And with a gentle push, the tip of his penis entered her vagina. He was so big it hurt, but it felt incredible at the same time. She wanted all of him inside of her. She wanted to feel him cum inside of her.

incest

Surprisingly this didn't hurt nearly as bad as it looks like it should. Possibly NSFW

pics

I woke up with my asshole hurting and this dark thing on it!! Am I going to die? (NSFL my hairy butthole with painful thing on it)

Health

I've had this for a long time, it doesn't hurt or anything, but what is it?

STD

{F}uck me 'till it hurts. c:

gonewild, AmateurArchives

He pulled it out when I was awake. It hurt a little.

pics

I hurt my finger a little today, it was a little numb but I didn't think anything of it, about 20 minutes later I found this.

ClopClop

Am I doing it right? It kind of hurts.

CheeseGraterBalls

Bump on my penis, I am a virgin and I have no idea what it is? It hurts like a pimple sort of. NSFW

STD

Her legs just keep spreading, it hurts to watch.

gifs, flexi, ConfusedBoners, randomsexygifs

Do you guys like my custom [M]ade chastity belt? It's going to hurt like hell to take it off

chastity

"Be thorough son, it's going to hurt if you don't get it wet enough"

hentai, traphentai

Ladies it's throbbing so much it hurts. 26[m]

gonewild

Reality hurts, doesn't it?

ImGoingToHellForThis

I made this in a game called Rust. It's probably knot as sexy as it is funny to look at, but, eh more content never hurts.

GayPokePorn

"I want it hard and deep", she says," (M)ake it hurt she says".. challenge accepted.

gonewild, MassiveCock, ThickDick

His cock is so fucking huge it hurts! But it's my job to please him!! Hes my king :)

AmazingCurves

SO HOT IT HURTS

JustHotWomen, u_PNWExplorer86, fortyfivefiftyfive, RetrousseTits, u_subndom191, u_MileHighScrub, u_majickstick, u_Sayon121, u_isomalware, u_greengiant87, u_incognitobiscotto, NaughtyFunthings, iWantToFuckHer, SoHotItHurts, Babes

This wouldn't hurt if it didn't hit to close to home

hentaimemes

I have this dark spot on my nip. It doesn't really hurt, but it is kinda sensitive. Should I be worried?

medical

Where does it hurt?

AraAra, ConfidentHentai

(18) it hurt a bit but I hope my pain and whimpers can help you cum <3 (don't worry I used lube)

anal, Slut, u_dereck8821, u_vpvids, NSFWtime, u_CapNo2425, u_ladykillar_29, AnalGW, u_Ioriindustrial, DegradingHoles, u_gumballzw, GoonRoom, u_robins_yupper, u_cumphession, u_Drookan, u_Bf109Emil, u_ehmokiguess, fuckdoll

I want to try anal. but I've never done it before. does it hurt?

AmazingCurves, hotclub, whooties, NaughtyNerdGirls, TheUnderbun, knockmeup, onlynudechicks, FatPussyLovers, 1819club, youngporn, Slutsofonlyfans, AdorableOnlyfans, OnlyfansAmateurs, SluttyOnlyfans, onlyfanschicks, FreeOnlyFansPage, onlyfanshottest, OnlyfansXXX

I want to try anal. but I've never done it before. does it hurt?

shavedpussies, Wife, CollegeAmateurs, EdibleButtholes, FatPussyLovers, 1819club, naughtychicks, GolemSexy, DirtySocialMedia, AmateurSlutWives, amateur_milfs, PussyAssTitsLover, pussyrating, TheUnderbun, PacksLatinas, PerfectPussies, Naked, fuckmywife, OnlyfansXXX

I want to try anal. but I've never done it before. does it hurt?

PornSelected, naughtychicks, GolemSexy, PussyAssTitsLover, pussyrating, Slut, AmateurWhores, PacksLatinas, BabesNSFW, PerfectPussies, AmateurSlutWives, amateur_milfs, DirtySocialMedia, CollegeAmateurs, EdibleButtholes, petite, PetiteGirls, shavedpussies, Wife

That if it hurts someone it might just bring snap~drunkboal?

Lela_Star

That if it hurts someone it might just bring s.n.a\p<filthynox

NSFW_Porn_101

POV Miss Kitty is so talented at sucking my cock..It must be the genuine enthusiasm behind it . Plus she's super sexy so that doesn't hurt

POV, BlowjobGirls, BlowJob