The next day when we woke up, Rocky and I got to work cleaning our dorm room and clearing a space for our beer pong table. Once we finished cleaning I made a quick call to a friend that I knew could snag us some beer for our little get together with Jill later that evening.
“Man I can’t believe this is really going to happen,” Rocky said while trying to hide just how truly excited he was.
“So you decided to bet on beating her in a round of beer pong? You know she’s really good, right?”
“I’m not worried. You saw the text messages that she sent last night, she’s into this thing too.”
“Well just remember that she takes her bets very seriously, so don’t hold back, even for one second.”
After a few hours, Jill was knocking on our door and Rocky shot up to open it. “Hey Jill,” Rocky said in a slightly shaky voice as he answered the door. Jill rolled her eyes as she walked passed him. She was dressed in a white crop top, a pair of short jean shorts, her wavy light brown hair was put into a loose messy bun, and she was wearing a pair of plain white flip-flops.
Rocky’s eyes stayed on her ass as she walked straight towards me and gave me a kiss. “So,” she said as she turned to face Rocky, “did you enjoy the free show you got yesterday you little perv?” He attempted to stutter out an answer before she put a hand up to stop him. “Look, you got lucky with that freebie, but that’s the only one you’re going to get.”
“I’m sorry about yesterday. I didn’t mean to catch you guys, but I also know you can’t resist a good bet.”
“Go on,” she said.
Rocky took a few steps closer and looked her dead in the eyes, “I’d like to place a series of bets. We’ll play beer pong and the person who gets to three wins first wins the right to choose the final punishment, but for each win that we get along the way we’ll be able to make up smaller punishments. Sound like a deal?”
Jill looked at me for a second before giving me a smirk. She shook Rocky’s hand and announced that they had a deal.
I sat back and drank a few beers as I watched them play the first game. It ended fairly quickly with Jill coming out victorious. “Hmm,” she said as she tapped playfully on her chin as if she was thinking hard about what the first punishment should be. “Ditch the clothes Rocky!”
“All of them?” he stammered.
“All of them,” she mused.
Rocky slowly started removing article after article of clothing until he stood completely naked. He looked a little embarrassed until he noticed Jill staring at his soft cock. Suddenly his dick twitched as it started to stiffen.
“Are you going to keep staring at his dick or are you going to keep playing?” I teased her.
She shot me an exasperated look before she declared that they start the next round.
About halfway through round two it became extremely obvious that Jill was struggling to keep her eyes off of Rocky’s cock. Everytime he would shoot his junk would flop around and she’d bite her lip. It didn’t take long for Rocky to gain victory and enact his vengeance.
“Strip it all off Jill,” he said maybe just a little bit to excitedly.
Jill began to walk towards me and turned her back to Rocky. She gave me one of her wicked little winks before she slowly began to remove her clothes. She gripped the bottom of her crop top and slowly began to lift it over her head exposing the black lace bra she wore underneath. She casually tossed it over her should towards Rocky. Next she began to undo the front of her shorts. She bent over and as she wiggled them down her long tan legs she give Rocky a perfect view of the G string that did nothing to cover her perfect ass.
She finally turned to face him as she reached behind her and unfastened her bra letting her big tits bounce free. Her pink nipples stood erect from the excitement that she felt from the strip tease that she was giving both of us. At last, she hooked her fingers through the strings of her thong before she slid it down to the floor. As her thong fell around her ankles, a long string from her soaked pussy stuck to the fabric and broke as her underwear passed her knees.
While Rocky stood dumbfounded by the nakedness of the beautiful girl right in front of him, Jill inserted two fingers into the wet lips between her legs. She pumped them in and out a few times before she brought her fingers to her mouth so she could lick them clean. With her tongue still running over her fingers, she asked him, “So, you ready for the third round?”
Source: reddit.com/r/sexystories/comments/rj2lht/mfm_highschool_teammate_turned_fwb_in_college