The Heiress and Her Friends

After dinner, Skylar Wayne and Dana Holland decided to take a walk on the beach together. They had been friends for a long time now, so it wasn’t a surprise to see them together. As they were walking, Skylar couldn’t help but check out all of the hot guys and women that they were passing. Her horniness was finally getting to her and she knew that if she didn’t get fucked soon, she would go crazy.

Dana was a virgin, but because of the way that the island was making her, she knew that she would be losing her virginity soon enough. She would feel better if it was someone that she knew. As luck would have it, two of their friends that were guys were approaching them now.

“I think it is time that we both get fucked. What do you say, Dana? Here come two of our friends now.” Skylar said.

“I’m up for it. Who do you want?” Dana asked.

“Great! I think I will take Sean. You can have Patrick. We can even switch up at some point.” Skylar said.

“Sounds good to me.” Dana said as the two guys were now right in front of them.

“You guys are coming with us. The two of us are in need of a good fucking.” Skylar said as she grabbed Sean’s hand and started to lead him away.

Dana turned to Patrick and smiled and then said, “I am not going to drag you around like that, but we should follow them.”

“Yep. It definitely looks like Sean is in for some fun.” Patrick said.

“Don’t worry, so are you.” Dana said with a smile as the two of them followed Skylar to her suite and to her bedroom inside of it.

As Dana and Patrick made it into the room, they could see that Skylar and Sean had started without them. Skylar was kissing Sean and he was returning the kiss. They were also losing their clothes faster than the viewers thought was possible and soon enough they were both completely naked.

Patrick turned toward Dana who turned to look at him at the same time. Patrick moved his hand to her face and then back into her hair and pulled the petite blonde into a kiss. Dana returned it right away and the two of them lost their clothes just as quickly as the other two in the room had.

Skylar had already dropped to her knees in front of Sean and was stroking his cock as it got harder in her hand. Skylar gave Sean a wink as she leaned in and licked his cock from base to tip.

“Oh Fuck!” Sean said as Skylar finally took him into her mouth.

The blonde took half of his length in the first go and seemed to be taking more and more of it every time she bobbed her head up and down his cock. Soon enough, Skylar had all of his length in her mouth and down her throat as she moved at a slow but steady pace up and down his cock.

It didn’t take Dana long to get on her knees in front of Patrick as well. She wasn’t the most experienced at giving a blowjob, but she did have some practice as she stroked him and then took half of his cock into her mouth. That was all that she was able to take due to gagging, which was fine with Patrick, since she was using her hand to stroke the rest of him.

“So good!” Patrick moaned as Dana continued to blow him.

Both of the guys were enjoying the blowjobs that the two blondes were giving them, but they were more interested in fucking the girls right now. The girls gave them blowjobs for another couple of minutes until they both pulled away from their guys and stood up and the two couples started kissing again.

Patrick took control of things with Dana as he walked her over to the bed and laid her down and then got on his knees on the floor in front of her and got between her legs and used his tongue to lick up her already wet slit. Dana moaned at the contact, but she moaned even more when Patrick started to focus on her clit with his tongue.

“Oh God! So good!” Dana moaned.

Skylar decided to take charge of what was going on with her and Sean. She led him over to the bed and laid him down so that he was comfortable and then Skylar straddled him. She leaned down to kiss Sean, but pulled away quickly and said, “I am about to give you the best fuck you have ever had.”

Sean just nodded as Skylar reached down and lined his cock up with her pussy and sank down onto it. They both moaned as the blonde girl continued to sink down on his sizable cock until he was balls deep inside of her.

Patrick had added a finger inside of Dana’s pussy and that was pushing her even closer to the edge. Patrick knew that Dana would be cumming soon so he doubled his efforts on her clit as well moving his finger in and out of her pussy faster.

“I’m going to cum!” Dana moaned quietly as Patrick was finally pushing her to that point.

It only took Patrick another minute to finally push Dana over that edge and the petite blonde was soon cumming all over his face and hand. “Yesss!” Dana moaned as she came.

Once she was done cumming, Patrick stood up and helped Dana to lay down on the bed comfortably with a pillow under her head and he then crawled up on the bed and moved to get in between her legs. He knew that Dana was a virgin, so he knew that he would have to take his time with her. She gave him a nod and said, “Just go slow, and that was all he needed from her as he started to push his cock inside of her. He went slow, so that Dana could get used to his size. He finally got to her hymen and looked down at her and she gave him another nod and he pushed through.

Dana moaned in slight pain as Patrick pushed through the barrier and she was glad that he stopped right after he broke through. Soon enough the pain was gone and the blonde gave Patrick a nod letting him know that she was okay to go and that was when Patrick started to thrust slowly in and out of Dana.

Skylar was still riding Sean as he was now reaching up and squeezing her tits and tweaking her nipples with his fingers. This was getting Skylar going even more than she already was. When Sean wasn’t doing that though, the blonde would lean forward and kiss him every now and then.

“Yes! Just like that!” Skylar moaned as Sean started to thrust up into her as he was now meeting every one of her thrust.

“So tight!” Sean moaned.

Skylar was surprised when Sean flipped them both over and started to fuck her hard. She didn’t know that Sean had it in him, but it turned her on to know that there was another side to the soft-spoken guy that not many people knew about.

“Oh yes!” Skylar moaned as Sean was fucking her hard and fast now and she was getting closer and closer to cumming.

Dana was really enjoying herself now that the pain had turned itself into pleasure. She never knew that sex could be so good. She was happy that she let someone like Patrick be her first time. Someone that she trusted and knew would never hurt her. She was really getting into things now as she was meeting each of his thrusts with her own. Dana wrapped her legs around Patrick’s waist to help her get some leverage so that she could meet each of his thrust.

“So good! I’m going to cum soon!” Dana moaned and Patrick continued his current pace since it seemed to be working well for both of them as he was getting Dana close to the edge and he still had plenty of stamina left.

Skylar was finally at the point of no return and she knew that she was going to be cumming soon as her pussy tightened up around Sean’s cock. About a minute later with the way that both of them were thrusting against each other, Skylar finally fell over the edge and came all over Sean’s cock.

“Yes! Yes! Yesss!” Skylar moaned as she came hard.

Sean continued to thrust into her as he still had plenty of time left. He looked over to where Patrick was still fucking Dana and the way that Dana was moaning now, he knew that Patrick would have her cumming soon enough.

About a minute after Skylar came, Dana came as well. “Yes! I’m cumming!” Dana moaned as she came hard around Patrick’s cock.

The two guys continued to fuck their current girl for another minute or so, until they finally pulled out of the girls, who moaned in disappointment that they were not getting fucked anymore. Patrick looked over at Sean and asked, “You want to switch?”

“Yeah. Let’s switch.” Sean said as he moved over to Dana and Patrick moved over to Skylar.

Both of the guys lined themselves up with the new girl in front of them and then pushed in slowly. Skylar didn’t need much work as Patrick pushed into her within two thrusts. Dana was a bit of a different story. It took Sean about five or six thrusts to finally get all the way inside of her.

“Fuck me hard, Pat!” Skylar moaned and Patrick was not one to let what was probably the most popular girls in school be disappointed as he started to fuck her hard and fast.

Sean took his time with Dana. There was no hurry and plus she seemed to be enjoying what he was doing, so why change things up yet. Dana had her legs and arms wrapped around him as she was slowly thrusting up into him while she was kissing him at the same time. Dana was loving everything that both Patrick and Sean had been doing for her and she was glad that the two guys were her first two times having sex. They were both sweet and they were good friends who she trusted.

Skylar had enough of being on the bottom, so she pulled Patrick down into a kiss and when he was leaning in, the blonde turned them both over so that she was now on top. Things really ramped up then. Skylar was riding Patrick hard and fast right now and Patrick was in a trance when Skylar finally sat straight up and her tits were bouncing with every one of her motions. He reached up with both of his hands and started to grope the blonde’s large tits.

“You like them don’t you, baby!?” Skylar asked and Patrick nodded as the blonde continued to ride him.

Because of the pace at which Skylar was going, she was getting very close to cumming again and she was hoping that the same was true for Patrick. She didn’t have to worry for long about that though.

“I’m so close!’ Skylar moaned.

“Me too!” Patrick moaned back to her.

Dana was getting close as well and Sean could tell it when her pussy started to quiver around him. He picked up his speed now as he wanted to give Dana all the pleasure that he could until she came. He knew that once he sped up that he would become closer to his orgasm as well. Not that that really mattered to him. He just wanted Dana to have a good time and it looked like she was.

“So close!” Dana moaned.

“Me too!” Sean moaned as well.

As the four of them were all getting close. Dana was the first one to hit her orgasm. She came hard around Sean’s cock as she gushed all over him.

“Cumming!” Dana moaned as she came.

Sean continued to fuck her as she rode out her orgasm. Sean was really close, but he still had some time, so he wasn’t going to stop yet.

“Fuck! I’m cumming!” Skylar moaned not long after Dana had cum, as the thought of her friend cumming pushed her over the edge.

Patrick was really close now and he asked, “Where do you want it, Sky?”

“In my mouth.” Skylar said as she got off of Sean’s cock so that she could move and suck him off until he came.

Skylar gave Patrick her best blowjob until she felt his balls tighten up in her hand and felt his cum hit her mouth and started to go down her throat. “Fuck! I’m cumming!” Patrick moaned as he shot his load in Skylar’s mouth.

Skylar sucked him clean and then crawled up and laid beside him as they both caught their breath.

While Skylar and Patrick were done, Sean was still fucking Dana, but he wouldn’t be for long as he felt he was so close that he probably didn’t have much time left. “Where do you want it, Dana?” Sean asked as he was so close now.

“Inside of me!” Dana moaned and Sean started to thrust even harder until he was shooting his load into her tight pussy.

“Oh fuck! Cumming!” Sean moaned as he came inside of the petite blonde.

Sean continued to fuck her until he knew that he had cleaned himself out and then he pulled out of her and moved his way up the bed so that he and Dana could relax for a little bit. Once the four of them had caught their breath, they all decided it was time to get dressed and get back out there to tour more of the resort.

“Well, that was fun.” Skylar said as she smirked at the two guys.

“Yeah, it was a lot of fun. Never though I would ever fuck either of you.” Sean said.

“The best you have ever had, right?” Skylar asked, but it wasn’t meant as a question and more of a statement.

“Damn right. You were both great.” Patrick said.

Dana was blushing a bit at the praise that she had just received from Patrick. “I don’t know about that, but I am glad that my first time was with you and my second time was with Sean.” Dana said and Patrick and Sean both nodded.

“I am glad that you had a good first time, Dana. Now I need to teach you some tricks to use on guys that will have them eating out of your hand.” Skylar said.

“I look forward to that.” Dana said.

“Great! Now let’s get back out there and see what else this resort has to offer.” Skylar said and all of the other’s nodded as they made their way out of the room and then the suite and started to make their way back outside to do some more touring so that they knew what to expect for the rest of the trip.