Sometimes It Takes Two

Rachel Stratton was standing on the edge of the landing that led down to the beach leaning against the railing looking at the people passing by. She was trying to judge what type of person they were as they walked by. She saw some men and women walking by together and she thought to herself, “Those two look like they are happily married or either they have been dating for a while. One or the other.”

She looked at a group of girls around Lacey’s age who walked by and thought to herself, “I wonder what they are up to? If it is anything like the cheer squad and myself back in the day, then they are up to no good.” She couldn’t help but smile when thinking about the old days. They were so much fun.

The next group that walked by were two boys who were around Lacey’s age. One of them was wearing glasses and was really skinny and the other one was skinny but didn’t have the glasses on, so he didn’t look as geeky as his friend. “I wonder what is going through their minds. The one with the glasses has probably never had sex and the other one probably hasn’t either. Those were always the most fun back in the day. Breaking in virgin boys.” Rachel thought to herself and then an idea came to mind. “Maybe I can help them out with that.”

Rachel walked down to the beach and made her way to the boys. “Hey guys, do you think you could help an older woman out? I am just going to ask some questions and I want you to answer me honestly.” Rachel said.

“Uh sure.” The boy with the glasses said.

“Are you both 18?” Rachel asked.

“Yes, we are.” The boy without the glasses said.

“Okay. What are your names?” Rachel asked.

“My name is John and this is Greg.” John, the boy with the glasses said.

“It is nice to meet you. I’m Rachel. So, this might be a bit personal, but what is your sexual experience?” Rachel asked and both of the boys blushed heavily.

“Um, I am a virgin.” John said.

“Me too.” Greg said.

Rachel looked down and could tell that both of the boys were pitching tents in their pants and she wanted nothing more than to help the two of them out with that and it would also be fun to teach them a thing or two. She was a teacher after all, so she would be doing her job. She just needed to find a way to bring it up without freaking the boys out.

She couldn’t really come up with anything, so she just decided to throw caution to the wind and tell them what she wanted. “So, my husband is back at home and this island and its aphrodisiac quality is really getting to me and it looks like it is getting to you as well.” Rachel said as she looked down to the boys pants which made them blush. “Here is what I am offering you. Both of you get to have sex with me and in return, you get to learn a thing or two about sex that will make you ready for any other girl on this island while you are here. What do you say?” Rachel asked.

“I think I would be an idiot to turn that offer down.” Greg said with a smirk.

“I would be stupid to turn down such a hot MILF.” John said as Rachel took both of their hands and led them back up the stairs to where the pool was.

“Sit on the side of the pool boys.” Rachel said as she moved to the shallow end so that she was able to touch the ground easily and the boys sat down side by side.

Rachel reached for the waistband of John’s shorts and started to pull them down. John lifted his ass off the concrete to make things easier for the redheaded MILF and he was soon naked from the waist down and his hard on popped free. She then did the same with Greg and now both boys were setting their waiting for the MILF to teach them a thing or two.

Rachel took off her bikini top that she had been wearing and the boys were now getting a good look at her very nice and large tits. She removed her bikini bottoms and then walked up between John’s legs which were hanging into the pool and started to stroke him with her right hand as she reached out with her left hand and did the same to Greg.

The redhead smiled up at John and said, “Just relax.” and then she leaned down and took the teen in her mouth.

John’s head fell backwards and he let out a moan. “Uhh.”

Rachel could tell that the teen wasn’t going to last long. She just hoped that what they said about the island was true and that guys were able to go again rather quickly. Rachel seemed to be right on track with her thinking. It only took a minute of her bobbing her head up and down John’s cock before he was about to cum.

“I’m going to cum!” John moaned as he started to cum into Rachel’s mouth and down her throat.

She continued to suck on the teen's passable cock of six inches until she was sure that he was dry of his cum and then she pulled back and swallowed it all. She then moved over in front of Greg and wasted no time in taking him into her mouth. She bobbed her head up and down his cock making the teen feel really good. “Oh shit! This is great!” Greg moaned and Rachel then pulled his cock out of her mouth and went down to suck his balls. Greg was on cloud nine right now. He had never felt anything so good in his life.

Greg was definitely lasting longer than John had. The teen also had a bigger cock than his friend did. He was a good seven to eight inches long and had good girth as well. John was only six inches, but his girth made up for it a bit though. Greg was about to cum though. Rachel could tell because when she put his cock back into her mouth she could feel it starting to twitch.

“I’m going to cum!” Greg moaned as started to shoot his load into the redheaded MILF’s mouth.

Rachel sucked Greg clean and then pulled back from him. She could see that John was hard again, so she pulled off his glasses and shirt and pulled him into the pool with her. John was the same height as she was, so she wouldn’t have to do much to position herself for the teen to fuck her. The redhead put her back against the wall of the pool and motioned for the teen to approach her. Once he did, Rachel wrapped her arms around John’s neck and pulled him close. She reached down between them and lined his cock up with her slit as she lifted her leg up so that he had a better angle on her.

“Push it in, sweetie.” Rachel said and John did as she said and he entered his first woman ever.

“Oh God, it’s so good!” John moaned.

You are doing good, just keep going like that!” Rachel moaned.

She was enjoying herself. It wasn’t all that great, but it was turning her on how much enthusiasm John had for this. He was pumping his cock into her with a gusto that she hadn’t felt a guy have with her in a long time, meaning that he was going fast and hard. She tended to like slow and steady now days, which was what Clive gave her, but for this trip she would take getting fucked hard.

John was feeling so good right now. He couldn’t believe that his first time was with a MILF and that said MILF was doing this willingly. He seemed to be lasting longer this time. He guessed that had to do with him cumming not too long ago. He knew that he wasn’t going to last long, but he was definitely going to take advantage of this for as long as he could.

Rachel had other things planned for the two boys so even when John was done, she knew it wouldn’t be his last time with her tonight. It didn’t take long for John to hit the point of no return.

“I’m going to cum!” John moaned.

“Pull out. We don’t want Greg to have sloppy seconds do we?” Rachel asked as John pulled out and climbed back on the deck of the pool and Rachel took him in her mouth and finished him off.

She sucked him dry again and then she looked at Greg and smiled. “Your turn buddy.” Rachel said as she pulled the other teen into the pool.

Greg had watched what was going on while John had been fucking Rachel, so he walked toward her and lifted up one of her legs so that he had a better angle, but Rachel stopped him before he could push into her. “I want to do this in another position.” Rachel said as she turned around so that her back was facing Greg.

She put her arms up on the side of the pool and stuck her ass out toward him so that he would have a better angle at her pussy. “Now you can fuck me.” Rachel said and Greg walked back up to her and wasted no time in pushing his cock into her pussy.

Rachel hadn’t cum yet because John hadn’t lasted quite long enough. He had gotten her close, but still not to the point where she was gushing for him. The good thing was that she was close enough that if Greg gave her a decent fucking, she should be able to get there this time.

Greg was learning from what John had done. He wasn’t going as fast and that was going to ensure that he would last longer. While he was fucking Rachel from behind, Greg was hitting that right spot and that was going to for sure make Rachel cum this time around. Greg’s size was also helping him. He was getting deeper and stretching her out a bit more than John had.

That was when it finally hit Rachel and she fell over the edge. “Oh fuck! I’m cumming!” Rachel moaned as she came around John’s cock.

That was all she needed. She had finally gotten off and now she felt relief flow through her as she had been so horny all day. That didn’t mean that she was going to stop now though. She still had things that she wanted to do with these teens while she had them at her disposal.

Rachel looked up at John who was still sitting on the side of the pool and smiled when she saw that he was hard and ready to go again. “Are you ready to get back into the game?” Rachel asked and John nodded eagerly.

John climbed into the pool and Greg pulled out of Rachel and waited for her to tell him what she wanted. Rachel motioned for Greg to come toward her. He did so and Rachel wrapped her arms around his neck and then wrapped her legs around his waist. “Go on and fuck me.” Rachel said as Greg positioned his cock at her pussy and pushed it in and started to fuck her slowly.

Rachel took one of her arms from around Greg’s neck and motioned for him to move over. “Put your arms up under my ass so that you can help Greg support my weight. Once you have done that, I want you to fuck me in the ass. Take it slow at first. I don’t do that as often as I used to.” Rachel said and John did as he was told and put his arms under her and then positioned his cock at her tight back door and started to push in, although it took a while because she was so tight, but he finally got his head inside of her and he waited for himself and Rachel to get used to the feeling.

Soon enough, both of the guys were moving their cocks in and out of Rachel at a good rhythm. When John was pulling out, Greg was pushing in. Rachel was finally feeling the way that she was wanting to feel all day. She was feeling great with both of these teens inside of her and it made her think that she needed to get Clive to fuck her in the ass more often when she got home.

“You are doing great, boys! Keep it up!” Rachel moaned as the boys continued to double penetrate her.

“God, her ass is so tight!” John moaned as he pumped his cock into her.

“You better not cum. I want my shot at her ass.”Greg said.

“There is more than enough for everyone, boys!” Rachel moaned as she could feel another orgasm coming on. The double penetration was really helping her.

The teen felt the MILF’s hole tighten up around them and the next thing they knew, she was letting them know that she had hit her second orgasm of the night. “I’m cumming!” Rachel moaned as she came hard for the double fucking that she was getting.

John was surprised that he didn’t cum with the way that Rachel had clamped down on him, but he and Greg continued to fuck the redhead until they felt her loosen up around them. Greg was ready to switch up though and he looked at John who nodded in agreement.

They let Rachel down, who almost lost her footing as her legs were a bit wobbly after the orgasm she had just had. Once she got her leg under her, Rachel reached for both of their hands and led them out of the pool. She led John over to a lounge chair and laid him down on it and then she got on top of it and straddled him and then lined his cock up with her pussy and sank down onto it. She leaned forward so that Greg would have better access to her ass and John loved the way that Rachel’s huge tits were rubbing against him as she was riding him.

Greg stepped up behind the redhead and lined his cock up with her asshole that was not as tight as it had been earlier and pushed his head inside of her with very little work. He didn’t even have to wait to start thrusting inside of her now as she was used to having a cock in her ass now. Because of Rachel being sandwiched by both of the teens, she wasn’t able to ride John as well anymore, so he had to do most of the thrusting into her pussy.

The guys soon got a nice rhythm going again. This time they weren’t going slow though as they knew that neither of them were going to last that long. Rachel was enjoying herself just as much now as she had when the guys were fucking her earlier. It had been a long time since she had been double penetrated and she had to admit that she had forgotten how good it felt. True, she was a grown woman now and she knew that she didn’t need this to be happy, but damn did it feel good to do some of the naughty stuff that she used to do back in the day. This week was going to be full of things that she hadn’t done in a long time if she had anything to say about it and once she was back home, she would go back to normal. Hey, it was like she said earlier to Peyton, “What happens on Lover’s Island, stays on Lover’s island.”

“Oh fuck! I’m going to cum!” Rachel finally moaned out as they guys were pounding her holes hard and fast.

The redhead tightened up around the teens and she came hard. “Shit! I’m cumming!” Rachel moaned loudly as she collapsed down on top of John.

The two boys continued to fuck her until they felt their own orgasms coming on. When they started to shoot their load into the MILF, they stopped and let their load explode into the redhead’s warm holes.

“Fuck! I’m cumming!” Greg moaned as he came inside of Rachel’s ass.

“Me too!” John moaned as he came inside of her pussy.

The teens continued to thrust into the redheaded MILF until they started to go soft. Greg pulled out of Rachel’s ass and climbed off of her. Rachel finally had her energy back and got up off of John and moved to the side of the pool where she had thrown her bikini earlier and started to put it back on. The boys moved to get dressed as well and then Rachel looked at the boys and smiled her motherly smile at them.

“That was fun, boys. I have a big group of girls here with me. How about you find me again tomorrow and I can introduce you to some of them. I am sure that some of them would be up to some fun with the two of you as well.” Rachel said.

“Sounds good. Should we set up a time to meet?” Greg asked.

“How about we meet her tomorrow at lunch time?” Rachel asked.

“Sounds like a plan. Thanks for helping us loosen up on this trip. Now that is out of the way, I think that things will be much easier.” John said.

“It was a pleasure. It always helps to have someone break the ice for you.” Rachel said.

“Well, we better get going. It was nice to meet your Rachel.” Greg said and John nodded in agreement.

“It was nice to meet you two as well. I will see both of you tomorrow at lunch time.” Rachel said and the three of them went on their way, but none of them knew that someone had watched most of the show and had gotten horny themselves and was now off looking for someone to fuck as well.