Jizz

Looks like it would hurt. NSFW

pics

Looks like it's hurting her a bit

AnalPorn

Is it gonna hurt?

LGBTGoneWild

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

gonewild

I'm so hard it kinda hurts.

penis, gonewild

[F]irst post, I may not be super fit, few extra pounds, but It cant hurt to try on here right? Gaurds need love to lol

ladybonersgw

just got my nipples pierced, it really hurt! what do you think?

BBW

So big it'll hurt ;) pm me ladies

MassiveCock

Thickness and length can vary ever so slightly, but it always hurts a little at first. 30m 8.5"x5"

MassiveCock, penis

"is it gonna hurt" (f)

gonewild

Horny + Photography skills + Lightroom + Me = nice (not sure if it would hurt but ive been told its huge)

MassiveCock, RateMyNudeBody

[M/S] But who was it really hurting?

taboocaptions

Best deepthroat, so sexy. BUT it must hurt as hell

The_Best_NSFW_GIFS, amateur_milfs

You guys like it to hurt?

MassiveCock

So hard it kinda hurts

selfservice, jacking, MenGW, MassiveCock, cock, penis, ThickDick

Yes, it will hurt

ThickDick, MassiveCock, cock, penis

When it stops hurting and starts feeling good!

nsfw_gifs

I saved you a seat, but it might hurt (PM's welcome)

foreskin

So hard it fucking hurts! Have you had that?

penis

So hard it almost hurts

MassiveCock

So hard it almost hurts

ThickDick, MassiveCock

Im so hard, it almost hurts ;) kik and snapchat are same as my username, pm me too!

cock

Drinking this weekend, got super excited and accidentally slid down 6 wooden stairs on my ass cheek in my friends house. It really hurts, NSFW

drunk

So hard it almost hurts... Who wants to satisfy my big cock?

MassiveCock

Pretty large plug, have to wetten it well. Hurt my asshole while being pushed in, but damn did i my asshole feel full, as if a cock was buried deep within ? [F]

gonewild

Damn, Reddit- It Stil Hurts

ImGoingToHellForThis

So hard it actually hurts! gotta cum to relieve the tension! Anyone else get this?

penis

So hard it almost hurts... ?

cock

[33] So hard it almost hurts

DadsGoneWild

Slip in.. Just promise me it wont hurt

Sissies

My favorite toy(s). I love being so hard it almost hurts

cockrings

Step 5. And have that next layer ready for when they start to fill up! Tip for bois... copious amount of aloe/lotion in the front will keep it from hurting if u get excited!

diaperpics

Put On That Spiked Chastity Cage. I Want It To Hurt While You Watch Us Have Sex

keyholdercaptions

Topped and Trimmed, it truly hurts :(

GrowingMarijuana

I know I asked for a spanking, but I didn't know it would hurt so bad!

adorableporn, Spanking, AbsoluteObedience

Please don't fear the monster in my pants... It only hurts like maybe the first 5 times

MassiveCock, gonewild, ratemycock, penis, MONSTERCOCKS, ThickDick

So hard it's hurting

foreskin

So hot it would hurt

SoHotItHurts

[M] Concept: Predicament CBT. If I push the sound out it will hurt more!

cbtBDSM

[m] So hard it almost hurts

gonewild

Well here I am. Still in the hospital of course and I'm 29 weeks pregnant with quadruplets. I'm now completely unable to walk without assistance and it physically hurts to stand. (Continued in comments. Open to questions or RP)

bodyswap

So hard it almost hurts!

cock, ratemycock

We all work together. He took her home last week instead of me. I always take her home, so it kinda hurt.

cuckoldcaptions, bangmybully

[f] I did fall from heaven and it didnt hurt cuz of this cushy booty

asstastic

Ouch! Honestly didn't expect it to hurt as much haha.

Nipples, fetish

This pantie was so tight it almost hurt my crotch [F]

UnderwearGW

So tight it almost hurts

BikiniBodies, thickwhitegirls, Thighs, thongs, BigButts, WifeyWorthy

No, It didnt hurt when I fell from heaven....because I landed on this big soft booty!

hugeasses