Jen

Gen wins, Jen loses.

"I'll be right back," Jen said as she suddenly ran off.

"Hey! No chickening out!" Tonya yelled. "Come get this ass fucking like a man!"

"That was so funny, I forgot to laugh." Jen came back with a tube in her hand. "I was getting some lube. No way in hell am I taking any of these guys up my ass dry." She walks up to Gen. "Let's see that cock again, hun." Gen dropped his pants and boxers and then Jen applied a generous amount of lube to his cock. Then, she whispered in his ear, "You didn't get my ass last time, so it's fitting. And this time, I can't blame it on the ****." She then got on her hands and knees in the center of the floor and wiggled her heart-shaped ass at Gen. "Come get it, big boy!"

"You don't have to tell me twice!" Gen exclaimed as he knelt down behind Jen. After lubing up her asshole, he put the head of his cock against her rosebud and started to push in.

"Just--just take it slow at first, okay? But you can go all the way in." He slowly sunk his cock into her ass up to the root, causing her to give out a long, loud moan. "Give me a moment. You're--a bit bigger than the last guy who got my ass. I don't usually let a guy this big up my ass."

After giving Jen a few moments to adjust, Gen started to fuck her ass with long, slow strokes. "Your ass feels...amazing. I didn't think anything could feel better than your pussy."

"Quit with the commentary and you might get to fuck me again in the future. Fuck, this does feel great, though." Nothing was said other than moans and groans of pleasure from both of them for a few minutes. Then, Jen said, "Fuck me faster!" Gen sped up, doing shorter strokes and Jen's moans got louder. Finally, she yelled out, "Harder! Fuck my ass harder!" Gen stopped holding back and started pounding her ass. "Ah! Ah! Ah!" Jen yelled out with every thrust. Gen grabbed and pulled her hair with one hand and grabbed one of her big, bouncing breasts with other. "Cumming, cumming, FUUUUUCK!" Gen stopped balls deep in her ass as her whole body convulsed with her assgasm. "Hah...hah... Don't stop. Keep going!" Gen started thrusting in her ass again hard and fast. This felt incredible and he didn't know how much longer he could last. Just as he felt his cock about to explode, Jen yelled out, "Fuck, fuck, FUUUUUCK!" as her body was rocked with another assgasm. This sent Gen way over the edge as he groaned and blasted what felt like a gallon of cum deep in her ass.

Gen pulled his softening cock out of Jen's ass and some of his cum leaked out. Jen immediately turned around and cleaned his cock with her mouth. Tonya walked over with a smug look on her face. "You're out, Jen!"

Jen slowly got to her feet and walked wobbly back to her chair. "I know, I know." As she walked past Terry, she stopped and said in a low voice, "If you win, pick me. I'll give you at least a month." Then, she walked away without an answer.