A Fun Award

As the five of them walked toward the room, Jenn turned to the guys and said, “Since I won, I want as much pleasure from this as possible, so only one of you are going to fuck me at a time. Let’s start with Billy.”

The two of them walked into the room and they didn’t worry about kissing as they knew that they were holding up the game the longer this took, so they both took their own clothes off and Jenn quickly made her way over to Billy and started to stroke his cock. She dropped to her knees and sucked on him until he was rock hard and then she got to her feet and walked over to the bed and laid down on it.

“So, how do you want me?” Jenn asked.

“I want to see that nice ass of yours, so I want you on your hands and knees.” Billy said and Jenn nodded and got into position.

Billy got up on his knees behind Jenn on the bed and wasted no time at all in penetrating her tight pussy. “Oh yes! That’s it! Fuck me!” Jenn moaned and Billy did just that.

He was fucking her hard and fast because they didn’t have the most time in the world to do this. There were also three other guys waiting outside the room waiting to fuck the brunette as well. Billy always loved it when he got to fuck Jenn. She always had such good energy when she really got into things which she was doing now as she was thrusting back against him as well.

Jenn wouldn’t say that Billy was the best she had ever had, but he always tried to do his best and that was all she could ask for. For the most part in their times together, he had always made her cum and she was definitely on her way there now.

“So tight!” Billy moaned as he fucked Jenn.

“Come on baby! Give it to me!” Jenn moaned and Billy picked up his speed and both of them could feel their orgasms coming on.

“I’m so close!” Jenn moaned.

“Me too!” Billy moaned back.

The two of them were really going at it now. Jenn was thrusting back against Billy at the same speed that he was thrusting into her. Jenn was getting louder and louder as they fucked as well, which was a sign of how close she was.

“Oh fuck! I’m cumming!” Jenn moaned and she clamped down onto Billy cock as she came.

Billy pulled his cock out of the brunette and started to jerk off and he finally shot his load on Jenn’s asscheeks. Once he was done, he put his clothes on quickly and left the room and the next guy, who was Greg, walked into the room and took off his clothes.

Jenn was on her knees in front of him in a flash as she started to suck his cock to get him ready. She didn’t do it for long. Just long enough to get him hard. She then pulled back and made her way over to the bed and turned around to Greg and asked, “How do you want me?”

“On your back.” Greg said and Jenn nodded as she made her way to the bed and laid down on her back.

When Greg got between her legs, he lifted both of them up so that they were on his shoulders and he lined his cock up and pushed it into her pussy. Because of the position that Jenn was in, Greg was penetrating her very deeply and he was going at a good fast speed as well.

“Oh fuck! That’s it! Right there!” Jenn moaned.

Greg kept fucking her just like he was but he had other ideas in mind. He wanted a piece of that ass that all the guys he knew were talking about. When he pulled out of Jenn she groaned in dismay as she thought that he was going to cum already. Her concerns soon went away when she felt him put his cock head against her asshole and start to push.

The brunette smiled up at the younger man and said, “So, you like to fuck girls in the ass?”

“Never done it before, but I have heard some of the guys talk about it so I figured I would try it.” Billy said as he finally got his cock head inside of her ass and Jenn moaned.

He fucked her slowly for a minute and then once she loosened up around him, Billy started to fuck her just as hard as he was fucking her pussy earlier. Jenn still had her legs up on his shoulders, so she was getting penetrated very deeply right now. She loved the feeling of having a cock in her ass. It was so intense and she always came so hard from it.

“Yes! Fuck my ass!” Jenn moaned.

Greg picked up his speed and he could feel his end was coming really fast and he hoped that the same was true for Jenn. It turned out that it was since she soon after that let him know. “I’m so close!” Jenn said as she started to rub her clit with her right hand.

It didn’t take long at all for Jenn to fall over the edge and come hard. “Oh yes! I’m cumming!” Jenn moaned and Greg could tell by how hard her ass contracted around him.

He pulled out and moved around to Jenn’s face and the brunette leaned up onto her elbows so that she had a good angle and then she took his cock into her mouth again until she felt him shooting his load into her mouth. “Oh fuck yes!” Greg moaned as he came into her mouth and down her throat.

Once she knew he was done, she pulled away from him and laid down on the bed so that she could catch her breath. Greg got dressed and left the room and soon after, Kirk walked into the room. Jenn didn’t have the energy to meet Kirk and suck him off, so she leaned up on her elbows again and let Kirk come to her and she sucked him off like that. Jenn didn’t even have to ask who Kirk wanted it as he took the initiative and turned her over so that she was laying on her stomach now.

Kirk had always loved fucking the hot older brunette in the ass so he was going straight for what he wanted. He spread Jenn’s cheeks with his hands and lined his cock up with her slightly gaping asshole and pushed in. “Yes! You know how I like it!” Jenn moaned as Kirk started to fuck her hard in the ass using her spit as the lube.

Jenn knew how Kirk was. He thought he was a ladies man, but sometimes he pushed too hard and it grossed girls out. It was lucky for him that Jenn wasn’t that hard to get, so he didn’t have to try so hard with her. He was one of her regulars as he didn’t have to work as hard for her. She had tried to give him some lessons on how to pick up girls his age and he used them and sometimes they even worked for him, but sometimes he would still push too hard and it ended up just like it had before.

Jenn was laying down on her stomach and Kirk was fucking her hard in the ass. The position that they were in allowed for a decent amount of penetration. The only problem was, it made it hard for Jenn to get her hand under her so she could rub her clit. It didn’t seem to matter though as she was getting close to her orgasm anyway.

“Fuck! Yes! I’m getting close!” Jenn moaned and that caused Kirk to start fucking her even harder.

Jenn had no leverage to thrust back into him, so it was all on Kirk and it seemed that he was doing a good job as she knew that she only had another minute left, if that. Kirk was fucking her really hard right now and she was loving every minute of it. She loved taking cock in her ass, but she wasn’t one of those who enjoyed it more than taking it in her pussy though, so she hoped that Chad did her in the pussy as it was feeling neglected.

“Oh shit! Yessss!” Jenn moaned as she came hard from Kirk fucking her ass.

Kirk wasn’t far behind her as he pulled out of her ass and barely had any time before he was spurting his cum all over Jenn’s ass. “Fuck!” Kirk moaned as he sprayed all over her fine ass.

Kirk stood up and went and put on his clothes and walked out of the room and soon Chad walked into the room and started to take his clothes off. He could tell that Jenn was very tired and knew that she wasn’t going to be able to do much to help him here. He walked over to her on the bed and she smiled at him. He was stroking his cock so it was getting hard just by looking at her fine, toned body.

“Put me in whatever position you want me. I’m a little out of it now.” Jenn said.

Chad nodded and got on the bed and picked the brunette up a bit so that she was on her knees and her ass was poking up in the air. Chad lined up with Jenn’s pussy, which she was happy about and he pushed inside of her. Jenn moaned as he entered her and she only got louder the harder Chad fucked her.

“Yes, baby! That’s how I like it!” Jenn moaned as she moved one of her hands so that it was rubbing her clit now.

Chad always loved fucking Jenn, the only problem with fucking her now was that she didn’t have much energy left. Normally she had so much energy and would give him just as good as he was giving her. This time it was all on him, which was fine. It was just going to take less time for him this time as he was having to really work hard and fast to get her off.

“Fuck! I love fucking you!” Chad moaned as he was fucking the brunette’s pussy hard now.

“You’re one of my favorites as well!” Jenn moaned.

Chad started to fuck her even harder now. He was just going to fuck her pussy this time around. He knew that he would have time later to fuck her ass as they had sex quite often. The sound of his hips meeting her ass was loud and very fast. He looked down at Jenn’s ass and watched it ripple with every thrust that he gave her, which turned him on even more.

Jenn was loving the way that Chad was fucking her right now. The two of them always had such good chemistry and he knew how to get her off and she knew how to get him off as well. They were regulars with each other, so it made sense that it was the case since they were familiar with each other. She didn’t know why her niece, Debbie disliked Chad and Kirk so much. She guessed that it had something to do with the way that Kirk went after women and the fact that Chad thought so highly of himself. It was a shame though as both of them were good boys at heart.

“Oh fuck! I’m close!” Chad moaned and Jenn knew that she was close too.

“Me too!” Jenn moaned and just like that, Chad started shooting his load inside of her pussy.

“Fuck! I’m cumming!” Chad moaned and the feeling of his load hitting the walls of her pussy was enough to push her over the edge.

“Fuck! Me too!” Jenn moaned as she came all over Chad’s cock.

Chad soon pulled out of her and Jenn collapsed onto the bed again. When she regained some of her bearings, she realized that Chad was getting dressed and was about to leave the room. “You better get cleaned up and back out there. I think we have held up the game long enough.” Chad said.

Jenn knew he was right, so she got up and went into the bathroom and cleaned herself back up and then walked back into the room to get dressed. She then made her way out of the room and back to the group and took her seat.

“So, I think since Jenn won the dare, she should get to go now.” Debbie said and everyone nodded.

Jenn thought about it for a second and then turned to her sister and said, “Josie, truth or dare?”