Can't chicken out now Ollie

Oliver stuck the dildo lower down on the wall and Tori handed him a stashed bottle of lube from the shelf. “Get your ass ready Ollie- hope you’re excited to eat some cum” Tori challenged as she stripped out of her clothes. Dropping them in a pile on the floor, Tori stood under the shower end of the tub, teasing gentle circles on her clit, watching with eager interest as Oliver lubed up the dildo, and his own virgin hole. “Ollie have you ever had anything up your ass before?” Tori asked, with a hint of concern as she stared at the nine-inch-long silicon cock. Oliver shook his head “One girl I fucked in junior year stuck a finger up there during a blowjob, but nothing like this” trying to relax his muscles, Oliver leaned back, aiming the tip into his well lubed ass.

Oliver gasped at the penetration; thankful he’d gone so heavy on the lubricant. He kept pushing, getting maybe a third of the way down before he had to pause. He looked up at Tori, drenched in the steamy water, oozing raw sex, she was an otherworldly vision. An arm covered in a sleeve of flowing vines and flowers lifted, gripping a breast the other, a patchwork sleeve lowered as she slid a finger between her lower lips. Tori watched Oliver, rapt with attention as her roommate began rocking back and forth. Oliver let out a slutty moan, his inexperienced prostate delighting in the stimulus. Every couple of thrusts he went deeper and deeper- still nowhere near the base of the behemoth shaft, but enough to start falling into a comfortable rhythm. Oliver steadied himself with one hand and brought the other to his aching cock. He quickly realized his chances of winning were slim, the avalanche of pleasure washing over his body from his first ass fucking was almost too much to bear. Oliver’s competitive nature kicked in, a Hail Mary to push Tori into defeat.

“You like watching me ride this cock, Tori? Watching me take this dick up my virgin ass?” Oliver moaned to emphasize his pleasure. Tori’s eyes widened, not expecting Oliver’s dirty talk, Oliver continued “it feels so fucking good Tor, I never- ohhhh fuck – never imagined how good it would feel to be stuffed full of cock.” His words had the desired effect, Tori’s fingers plunged into her dripping sex, rolling a pinched barbell pierced nipple between her fingers. Tori’s pale face was flushed, her breathing becoming ragged as she watched Oliver’s lean frame bounce back and forth on her dildo. In the interest of fairness, Tori increased her own pace, fucking herself just as hard as her unexpectedly slutty roommate fucked against the wall.

Despite all this, Oliver knew he was fighting a losing battle, he grit his teeth, staving off the orgasm building in his core. A flash of inspiration and he burst out “bend over and turn around NOW.” Shocked into submission, Tori obeyed, offering her ass to Oliver, continuing to fuck herself with her fingers. Oliver buried his face in her ass, licking her puckered asshole with wild abandon “Oh my godddd Ollie holy fuck yes lick my ass you fucking slut” Tori moaned. All pretenses of keeping quiet enough to conceal the tryst from Alex abandoned, Tori felt Oliver’s tongue plunge into her ass “OH FUCK FUCK FUCK FUCK MY ASS WITH YOUR TONGUE.”

Both Tori and Oliver danced on a razors edge of pleasure, the bet a distant memory drowned out in the urgency of the incoming orgasms. But one had to be the first to fail.