Jizz

Forget Kari Byron. This redheaded lass right here was the subject of my teenage fantasies and acted in my favorite TV show. Nerdy redhead + alien conspiracies. What could go wrong? (possibly NSFW)

pics

What could go wrong?

funny

What could go wrong?

mylittlepony

Modelling for Wikianswers? -sure, what could go wrong...

NSFWFunny

What Could Go Wrong? NSFL

dadscoke

Thigh highs and ass, what could go wrong? (f)

gonewild

I'll just answer the door in a towel. What could go wrong?

Whatcouldgowrong, HappyEmbarrassedGirls

"I think I'll let this black guy fuck me, what could go wrong?"

HugeDickTinyChick

Well I'll just run the installer for this seemingly innocuous "Powerpoint Image Extractor" software at work, what could go wrong? [NSFW]

softwaregore

One pickup truck, a dozen dumb kids, fifty miles an hour. What could go wrong?

Whatcouldgowrong

Someone sat down and thought "this is a good idea, what could go wrong?"

ABDL

Pushing over this brick wall, what could go wrong? [nsfl]

Whatcouldgowrong

Pink thong and short shorts. What could go wrong?

GoneWildCD, Sissies, traps

Fishnets and Tits. What could go wrong?

BigBoobsGW

Bucket elevator. What could go wrong?

OSHA

Two little cups, what could go wrong?

tiny_saggers

Rope, cuffs, and a Hitachi. What could go wrong?

Deenasaur

"What could go wrong?"

ImGoingToHellForThis

A Floating Sentient Dagger, what could go wrong?

TBoIRule34

What could go wrong

ImGoingToHellForThis

Youve been rebelling against me pretty hard son, staying out late and drinking. Lets wrestle, if I win you go back to being my sweet obedient son, if you win, well ill be pinned underneath you... im 4'9" and 85pds what could go wrong.

gonewild

Practice Burning Out in the Garage: What Could Go Wrong?

Whatcouldgowrong, nononono, motorcycles

Goth camp counselors are a thing, right? Just having sexy times on Friday the 13th, alone, in a cabin, with the windows open...what could go wrong?

traps

Bad women's anatomy + Racism. What could go wrong?

badwomensanatomy

Loose fitting Tshirt Dress, no panties, what could go wrong?! (F20)

gonewild

What could go wrong? (Not sure if NSFL)

WhyWereTheyFilming

What could go wrong :X

bowsette

Let's jump in a high pressure water jet, what could go wrong? (NSFW) | Jacking off in full leather attire (NSFW)

gaypornornotgayporn

What could go wrong...

u_SissyQuin

What could go wrong?

hentai_irl

Hot drink. Hot girl. What could go wrong?

keyholdercaptions

A whiskey bottle, a pair of glorious ass cheeks and a fat pussy. What could go wrong?

phatpussy, BBW

Their sex life had gotten a little stale recently, so she thought she'd surprise him. What could go wrong? [surprise] [embarrassed] [naked] [wife]

xxxcaptions

(F)lying horny, what could go wrong?

gonewild

what could go wrong if i ......

u_nassime26

Quarantined and depressed I've decided to start a new hobby! What could go wrong, right?

BoJackHorseman

Playing in the fountain ~ what could go wrong?

WhyEvenWearAnything, iluvnakedchicks

What could go wrong if i drive my car in a high speed to the parking lot

u_kayotic123

Dr. martens boots & some cotton rope. What could go wrong? ❤ I love this look.

bdsm

Blue hair and Tiddies! What could go wrong here? ?

GirlswithNeonHair

I guess Starbucks couldn't be expected to hire ALL of the sociology and underwater basket weaving majors! Camwhore Career--What could go wrong?

WhereAreAllTheGoodMen

What could go wrong engaging in a little bondage with a stranger...

u_xxxSissyCaps, sissycaptions, u_SouthernError0, sissyplace, StraightToSissy, sissydressing, u_nimblybimbly436

What could go wrong trying to join a gang when you're a white boi with a weak feminine figure...

u_xxxSissyCaps, sissycaptions

What could go wrong using your wife as a wager in a bet?

u_xxxCaps, cuckoldcaptions, u_nimblybimbly436

What could go wrong dressing as a sexy ballerina for Halloween...

u_xxxSissyCaps, sissycaptions, u_str8btcurious, u_Blooming-Sissy-Sam

Two cat girls and two black cocks, what could go wrong?

Hentai_Interracial, 3113LIONHEART

What could go wrong?

NSFWFunny

Eating only steaks : WHAT COULD GO WRONG?

vegancirclejerk

what could go wrong

u_Longjumping-Ninja-71

What could go wrong

u_vitrioleater

A bottle of Moscato and an iPhone...what could go wrong?? ;)

BigTitsLovers, BustyNaturals