The Sleepover Part 3

Ashley came up with her dare quickly and it made her smile on the inside because it would allow her to do what she does best. Play matchmaker. She looked at her friend Brandon and knew that this was going to work out well for him in the end.

“Brandon, I dare you to take Chloe into Zack’s room and get each other off. It doesn’t matter how you do it.” Ashley said.

Brandon was not opposed to the idea, but he could tell that Chloe was a bit nervous, but she also had a look of excitement as well. He didn’t really know how to read that, but he wasn’t going to turn down the chance to do something with the cute redhead.

“Alright. Let’s go Chloe.” Brandon said as he reached out and took her hand and led her into Zack’s room.

Once Brandon closed the door and turned around to Chloe, she was on him, pushing him back into the door and making out with him. It took Brandon a couple of seconds to respond, but he finally did. They both made their way to the bed and both sat down, while breaking the kiss for a second.

“What do you want to do Chloe? I won’t **** anything on you.” Brandon said.

“I want to have sex. I have a list of guys that I would be willing to fuck on my first time if I wasn’t in a relationship and you are on it.” Chloe said.

“Well, I am honored, but are you sure?” Brandon said.

“I am. I want to do this. Please fuck me Brandon.” Chloe said.

“How can I turn that down?” Brandon said with a smile as they both started kissing again.

It didn’t take the pair long at all to be completely naked and they were now laying down on the bed. They were still kissing and doing all of the foreplay, when Brandon pulled back and smiled down at the redhead.

“Are you ready for this?” Brandon asked.

“Yes. You don’t have to take it easy on me. I won’t break.” Chloe said.

“I will at first. It is your first time after all.” Brandon said and Chloe nodded.

Brandon pushed into the redheaded virgin with the first couple of inches of his dick and stopped so that Chloe could get used to his size. Chloe gasped as he entered her and Brandon hoped that he wasn’t going to fast for her. After feeling her relax a bit around him, Brandon decided to push further in. It went a lot smoother from here and soon he was balls deep inside of the soccer player.

“Oh God! I have never felt so full in my life!” Chloe moaned.

“Is everything okay?” Brandon asked.

“Yeah, perfect. You can move now.” Chloe said as she smiled up at Brandon.

Brandon did just that. He moved at a slow pace in and out of the redhead and he was starting to get a whole lot of excited moans from her, which made him feel better because he knew that he wasn’t hurting her.

“Fuck yes! Right there, Brandon! Fuck me!” Chloe moaned.

“You like that don’t you. Well, I have something else for you.” Brandon said as he started to thrust faster into the former virgin.

Brandon had been having sex for a while now, so he was nowhere near being done even though he was thrusting rather hard and fast into Chloe. He wanted to make Chloe feel as good as she could on her first time, so he continued to thrust into her while kissing her down her neck and he soon made it to her tits and started to kiss and suck the left on first and then he moved to the right one making sure that they both got the same treatment.

“Oh God, Brandon! That feels so good!” Chloe said after Brandon had been sucking on her tits while still fucking her.

“Chloe, you are so tight.” Brandon said.

Brandon continued to sucking and kiss her tits and he was amazed at how they jiggled with the way that he was thrusting into her. He never would have thought that Chloe had such a nice body with the way that she dressed, but he knew now and he wouldn’t mind at all if he got to see it more often in the future if things went right here, tonight.

Chloe had similar thoughts. She had already thought that Brandon was hot and wouldn’t have minded dating him, but with him having fucked her, what was stopping them from dating. She hoped that the guy would ask her out by the end of the night. That would be like putting a cherry on top of this amazing night for her.

“This is so good. I never thought that it could be so good!” Chloe said to the dark haired guy who was fucking her right now.

“I am glad you are enjoying your first time. Anything else you want to do?” Brandon asked.

“NO! Keep fucking me! I want to cum and I am so close!” Chloe moaned, at first being afraid that he was going to stop what he was doing.

“Don’t worry. I will make sure you get off.” Brandon said as he continued his good work.

“Thank God!” Chloe moaned even louder.

Brandon knew that Chloe was getting close, so he picked up the pace a bit and went on sucking her tits while rubbing her clit as well. This sent Chloe over the edge and she had her first orgasm from penetration from a real dick. Over course he had used her dildo plenty of times.

“Oh Fuck! I’m cumming on your dick!” Chloe moaned as she came.

Brandon slowed down because he knew that if he continued at the pace he was going while she was tight because of her orgasm, he would cum fast and he wasn’t ready for this to end yet. Once he could tell that Chloe was relaxed again and not so tense from the orgasm, he started to pump into her fast again.

It didn’t take Chloe long to get some of her stamina back as well and she wanted to be in control this time around. Brandon was surprised when he found himself on the bottom all of a sudden. He wasn’t one who was normally on the bottom during sex, but he wasn’t going to turn down the chance to watch Chloe ride him, while her tits were bouncing up and down.

“Oh fuck! This is even better!” Chloe said and Brandon couldn’t help but laugh at her enthusiasm.

Brandon reached up and took a bouncing tit in both of his hands and lightly squeezed them so that Chloe would experience even more pleasure. Chloe picked up the pace and soon both of them were feeling the pressure and they knew that they would both be cumming soon.

“You are doing so good Chloe! Keep it up!” Brandon moaned.

“This is so good! I love sex! I want you to cum in my mouth!” Chloe said.

She continued to ride Brandon for a bit longer and then she could feel the sign of her orgasm coming along, so she just let it happen.

“Oh God! I’m cumming again!” Chloe moaned as she fell over on top of Brandon, completely worn out.

Brandon pulled out of her and then turned her over to lay her on her back. He then straddled her chest and began to stroke his cock. It didn’t take long for him to feel the signs that he was about to cum.

“Chloe, open your mouth. I am about to cum.” Brandon said and Chloe did just that.

Brandon continued to stroke himself until he knew he was going to cum. He then leaned forward and placed the head of his cock in the redhead’s mouth and then he came hard.

“Oh fuck yes! I’m cumming!” Brandon moaned as he continued to shoot all of his cum into her mouth and down her throat.

Once Brandon was done, he pulled away and Chloe smiled up at him and opened her mouth to show him all of the cum. She then shut her mouth and swallowed, taking it all down her throat.

“That was fun. Thanks for taking care of me tonight.” Chloe said.

“It was no problem at all. I enjoyed it too. I was wondering if you would like to go out for dinner or a movie sometime though?” Brandon asked.

“I would love that. Let’s set it up tomorrow before we leave.” Chloe said happy that this had happened.

“Sounds good to me. Let’s head back out there and get this game going again.” Brandon said as the two of them got their clothes back on and made their way back out to their friends.

. . .

Soon the new couple was back out in the room with the rest of their friends and ready to resume the game. It was now Brandon’s turn to dare someone to do something. He thought about it for a minute and he knew what he wanted to do because he always got a rise out of doing something like this.

“Sharon, I dare you to take Gavin into Zack’s room and get him off. To prove that you actually did it though, you have to show us his cum.” Brandon said as he started to laugh because Sharon quickly had a disgruntled look on his face.

“Come on, Brandon. Seriously. Why would you do this to me?” Sharon bitched as she looked at the guy who she thought was her friend.

At this, Everyone started laughing to the point of them all about to cry they were laughing so hard.

“Fuck this shit! Fuck all of you!” Sharon yelled at all of them, causing them to laugh even harder.

Soon things calmed down though and Brandon looked at Sharon and said, “You can always take the consequences if you don’t want to do that.”

“What would that be?” Sharon asked.

“You take Zack and Gavin in the room and they spit roast you.” Brandon said with a smile.

“UHHHH! Fine! Come on Gavin, let’s get this over with.” Sharon said as she walked toward the bedroom with Gavin following her with a big smile on his face.

Once they were both in the room and Sharon shut the door and locked it and then turned around to the loser. “Take your pants off loser. Let’s get this bullshit dare over with.

Gavin wasted no time pulling his pants down. Sharon had to admit that for a loser he didn’t have a bad dick, but she wasn’t going to let him know that. She walked over to him and grabbed his cock in her hand and started to stroke it slowly. It didn’t take Gavin long to get as hard as a rock, so Sharon thought this was going to end quickly.

Gavin started to moan and this made Sharon think that this was going to be over quickly. Unfortunately, Gavin was used to hands beating him off since he jerked himself off all the time. Sure it felt better with it being someone else who was doing this for him, but he still wasn’t close to his orgasm yet.

Sharon was starting to get pissed that this wasn’t going as quickly as she had hoped that it would.

“Fucking loser! Would you cum already!” Sharon pretty much screamed at Gavin.

“Sorry to disappoint, but I am used to handjobs. Of course your’s feels better than mine, but it is still a handjob, so this could last a while.” Gavin said while laughing slightly at the mean redhead.

“Fuck this! I will finish you off quick enough!” Sharon said angrily.

Gavin didn’t know what that meant, but he was looking forward to finding out. The next thing he knew, Sharon brought her other hand up to her mouth and wet one of her fingers. Gavin was really curious now.

To Gavin’s surprise, Sharon put her hand on his ass cheek and moved it to his ass crack. She continued to move her hand until her wet finger was over his asshole and then she pushed it in.

“What the hell are you doing?” Gavin asked, not liking where this was going.

“This is going to get you off, loser.” Sharon said as she went deeper and deeper with her finger until it was all the way into the loser’s ass.

She then went to work on finding his prostate and massaging it. Gavin was still weirded out about what was going on.

“Stop that! I just want you to beat me off!” Gavin said, but as he said it, he had to admit that it was starting to feel pretty good, which was weird.

Sharon kept on with her plan. She even stopped beating his dick for him and she was happy when she heard him start to moan. Sharon knew that this loser would end up liking this, so she smiled and kept doing what she was doing.

Soon Gavin was moaning so much. Sharon waited for Gavin to voice his opinion again but nothing came but moan.

“So, do you like that, loser?” Sharon asked.

“Yeah. It actually feels good!” Gavin moaned.

“Good. Go over to the bed and get on your hands and knees with your ass in the air.” Sharon said as Gavin did what he was told with her finger still in him the whole way.

Once he was in position, Sharon started to pump her finger in and out of his ass so that she was still massaging his prostate. Gavin was really enjoying himself now, if his loud moaning meant anything. “What a fucking loser.” Sharon thought to herself as she continued what she was doing.

“Are you getting close to cumming?” Sharon asked.

“I think so. It just feels so different, so I don’t really know.” Gavin said.

“Good. I want you to start beating your cock from this position. I will keep fingering your ass.” Sharon said and Gavin did as he was told.

Gavin’s moaning got even louder if that was possible. Sharon knew that he had to be getting close. Gavin’s next statement let her know how true that was.

“I’m going to cum!” Gavin moaned.

Sharon kept her finger plunging into his ass while Gavin kept beating his cock. Sharon reached up under him until his dick head was just about touching her hand and she soon felt his cum shooting out of his dick and into her hand.

“Oh fuck! I’m cumming!” Gavin said as his load was shot into Sharon’s hand.

Once he was done, Gavin collapsed onto the bed. Sharon just shook her head and waited for the loser to regain his wits.

“Pull your pants up loser. We have to go out there and finish this dare.” Sharon said meanly to Gavin.

Gavin did as he was told and they both exited the room.

“We all know that Gavin got off. How do we know that you did it though? Heather asked.

“I think this will answer your question.” Sharon said as she walked over to Heather and smeared the cum all over Heather’s face.

Sharon was wondering what would happen next. She was waiting for the cheer captain to go off on her, but to her surprise, Heather started guiding all of the cum to her mouth and taking it inside. Once she had gotten it all in her mouth, she started to gurgle it and then she swallowed it with a smile.

Sharon stomped her foot on the floor and made her way back over to her seat, not liking the way that her friend had just shown her up. She was expecting to have the upper hand after this, but it didn’t turn out that way, so she just sat there fuming for the time being.

Once she looked like she had calmed down a bit, Ashley looked at her and said, “It’s your turn to dare someone to do something, Sharon.”

Sharon got a devious look on her face since she knew that this would be the perfect time to get Heather back for showing her up. She smiled at the plan that she came up with. There was no way that Heather would be happy about this.