With a whimper and a bang

Penelope let out a humiliated squeak and a whimper as she felt the mans finger poking at her rear end, and occasionally his thumb teasingly rubbing up and down her shamefully slick slit. "C-come on! L-let's talk abou-!" She tried to protest before squeaking and tensing in pain as he gave a punishing slap to her ass cheek for daring to speak, leaving a red handprint behind. She blinked and tried to glance over her shoulder in confusion as she felt something cold and wet on her asshole. "W-what are yo-!?" She tried to ask, earning another smack. He massaged what she assumed was lubricant into her rearend with his finger, causing her to cringe slightly and let out an awkward groan from the confusing sensation of his finger pushing inside of her. She wondered to herself if this counted as losing the challenge, not that it really mattered, what he was likely to do before he was done with her would almost certainly count as losing. She thought about trying to reason with him again, but she didn't see a point, he simply continued methodically preparing her ass for his personal use. Then a fearful shiver rolled down her spine as he lined himself up behind her, his tip prodding at her backdoor intent on bursting inside. "S-stop! Th-that thing will never fit!" Penelope protested in panic, clenching with all her might trying to repel his entry.