Waking Up Pt. 05

All characters in this story are 18 or older. The names have been changed to keep their secrets.

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Part 5 - The Rules of Boating

The next weeks were amazing. Jack and Kate had made the most of the time that they had together. They would kiss in the morning in the bathroom sometimes until both of them were so turned on that they forgot the time, and would sometimes be interrupted by Amanda calling up the stairs for them. One morning, Kate had dropped to her knees and completely sucked Jack off before going to school. She still couldn't swallow a whole load, so she spit into the bathroom sink, but Jack didn't care. Sending his little sister off to school with a wet pussy after sucking him off was good enough.

At night, Kate would often sneak into Jack's room, wearing next to nothing, and start a long make out session. Jack loved kissing Kate and touching her all over her body. Kate was ok with Jack taking off her underwear now, if he was going down on her. But she had announced her rules to him about not poking at her so hard with his thingie. It was against the rules for him to be naked and get on top of her while she was naked too. One of them should always have their bottoms on. She was a good girl after all. Jack didn't mind Kate's rules. He was still cumming a lot and getting to explore her body.

In the shower, Jack would sometimes put his hard cock between his sisters legs and move back and forth, while he rubbed a soapy finger around her butthole. Kate loved this more than almost anything. And somehow this wasn't against her rules. Kate would feel the sensations building in her body, but she still hadn't had an orgasm yet. Jack asked her about it, and she had explained that it was harder for girls sometimes. They talked some about the whole "letting go" thing some more, since Jack was wondering if that was it. Then there was the issue of never really being alone, because they were always worried about who would come home.

This didn't stop Jack from trying to get Kate to orgasm. One day he walked in on Kate changing in her big closet. He pulled her panties down, and she bent down with her hands on the hamper in her closet. Jack got down on his knees and put his hands on Kate's beautiful bare ass. He kissed all around it as Kate giggled. Then he gently pushed her cheeks apart and his tongue darted for her tight little hole. Kate would gasp, as she still couldn't believe how he wanted to lick her there. Jack would rock back and take in this view. He would use his fingers to open up his little sister's pussy lips and then dive back in. Kate was becoming a big fan of oral, as it brought her closer to what she thought sex was supposed to be all about. The intimacy of a boy between your legs and the trust there.

And Kate knew something that Jack didn't know. Amanda had taken Kate to her gynecologist after Kate had complained about some irregular periods. Kate was surprised when the doctor put her on the pill, saying that it would help to regulate her cycle. Amanda was actually relieved, because she remembered what she was doing when she was Kate's age. Amanda started talking to Kate about sex on the drive home and reminding her that the pill didn't protect her from diseases, only from getting pregnant.

"Jeez, mom! Can you drop me off at the school gym? I'm supposed to bang the whole football team today" Kate said with a wicked smile on her face.

"Katherine!" Amanda objected.

"You don't have to worry about me, mom. You raised me right", Kate said, rubbing Amanda on her shoulder.

"Well, if you ever want to talk" Amanda didn't even finish her whole thought. She wouldn't have told her mother about when she gave a guy a blow job or anything. "I'm here for you, Kate. And I love you."

"Thanks, mom."

As summer approached, Kevin asked Jack over breakfast to go to the boat dock and get the boat ready for the season. Kevin was always at the restaurant, and getting everything working for the season on the boat was a big job. Jack said he would do it, but that he needed some help. Amanda was at the table and asked Jack which of his friends he wanted to take along. Jack thought for a moment, "I'll get Kate to help me" he said.

"Good luck with that" Amanda said with a snort.

Jack thought he could talk her into it.

Later Jack pulled out his phone.

J: I know what we're doing 2 days from now.

K: You do?

J: We're going to get the boat out. You and me.

K: Oh shit.

J: Come on. It will be fun. We'll get it uncovered and set up. Go for a short cruise and a swim. No one around to bother us.

Kate thought about it. She would need a new bikini. Now that she was waxed down there, she could wear just about anything. She also thought about the bikini that she would be willing to wear around just Jack. This called for some immediate shopping.

K: Ok. I'm in.

Two days later they were driving out to the dock with a cooler packed with lunch and some beers that Jack had got his hands on somehow. The boat was a 40 footer. It was mostly open in the back and had a cabin down below in towards the bow. There was a galley area with a table, a tiny bathroom, and a stateroom with a bed in the bow.

Jack was already thinking about what could happen when he saw Kate in her short shorts, and a loose tank top that gave a preview of her white bikini underneath. After the initial hard labor of removing the cover, stowing it, getting the engine started, getting fueled up, filling the water tanks, and checking all of the major systems, it was finally time to head out.

The dock was close to the outer parts of the bay, so it wasn't long until they were out in the gulf and moving at full power. Kate went down below, and when she emerged, Jack's jaw dropped. She was wearing a tiny white bikini, that had little ties around her neck and back, and also two at her hips that held on her bottoms. Kate's cleavage was something to die for, and her little ass was barely covered by the low cut bottoms.

"Amanda was not with you when you bought that" Jack said with a smile.

"What she doesn't know won't hurt her. And I thought you would like it."

"You thought right." Jack said, as he took off his shirt and got ready for a day of fun in the sun.

Jack took the boat out along the sand keys that lined the coast. There would normally be some guys fishing in along this path, but it was maybe too late for prime time, or an off day, but they were completely alone. He guided the boat into a little cove that was lined with palm trees. The water was fairly shallow, and Jack jumped out to secure the anchor. Kate blew up one of the floating loungers with the air pump, and tossed it in the water. She followed right behind it.

They both grabbed onto the float. Jack gave Kate a kiss and ran his hand over her bare back.

"I told you that this would be fun" he said. Then he swam underneath the float and came up on the other side.

Kate had both of her arms up on the float and gently kicked her feet in the water. "Thanks for talking me into this. It's a lot different doing it with you than it is with dad. You only ordered me around a little" Kate said with a slight smile.

"You are an excellent first mate" Jack said, as his legs touched hers under the water. "Besides, this is something we've never had - our own place."

Kate looked around and nodded. She looked back at Jack. He was looking at her so intensely, she said "What?"

"Kate, you know that I love you. I will always love you. And I don't mean that like I love you like some random family member either."

Kate looked at him. He had never said that to her before. No guy had ever said it to her before. "I'm glad you told me. I was hoping you did."

"You knew I loved you" Jack said.

"Guys are so dumb. You have to say it. You can't just leave a girl guessing. Plus, it's nice to hear you say it" Kate said while looking him with a smile. Then she went under water and came back up on Jack's side of the float. She put an arm around him and gave him a long kiss. When she broke it off, she put her mouth right by his ear and whispered, "I love you too. And I always will."

There was real intimacy there as they floated in the water together. They laughed and talked about what they wanted to happen this summer. Jack talked about what he wanted to do when he moved out. He got the beers out of the cooler and they both had a few. Kate made fun of Jack's playlist that he had going over the boat's speakers. She said that her playlists were much better and swam back towards the stern to get out of the water. Jack followed closely behind.

Once standing on the swim deck, Jack pulled out the shower attachment at the stern used to wash off the salt water. It was a short bit of hose with a spray nozzle like a shower. He held it above Kate's head and pulled the trigger, releasing the fresh water over her. Kate's eyes were closed and Jack took in her whole body as he rinsed her off. The cool fresh water had her nipples pointing through the thin bikini material of her top. Her smooth, flat stomach looked amazing, as he instructed her to turn around so he could get the rest of the salt water off. Jack looked at his sister's perfect teen ass as she slowly turned.

Kate stepped up into the boat and grabbed a towel, and Jack quickly sprayed himself off.

"I think I could use a nap" Kate said, looking at the little door that lead to down below. "The good music is down there too."

Jack didn't say a word. He just watched as Kate disappeared inside the cabin. She was still rubbing her hair with the towel as she went down the narrow stairs. Maybe he still didn't understand much about girls, but he understood this much. He was on the stairs in seconds. He heard music playing as he closed the door behind him.

"Now that is better" Kate said. "A normal person could even dance to this."

"I know you like my music" Jack said. "I see you smiling and singing along to it all the time."

"It's ok" Kate said smiling. "Sometimes you need something different though." Kate turned towards the stateroom and pulled on the string on her back that held her top on. She pulled the top over her head and turned around to face Jack. Her hands were by her side. She wanted him to look at her and to touch her. She wanted to make him hard.

Jack stared at his sister. Her nipples were at full attention, and so was his cock. He took her in his arms and kissed her. Kate melted in his arms. Both of them loving the feeling of their bare chests touching. Jack's hands moved to Kate's almost bare ass and squeezed her perfect little ass cheeks. Kate raise her arms above her head and turned slowly, as Jack ran his hands all over her body. She continued this slow dance for a while, looking Jack in the eyes when facing him. Then she turned her back to him and leaned back into him. Feeling his hard dick, she grinded has ass against it. Jack's hands moved up to her tits and he gave them a firm squeeze. Kate let out a little cry when he tweaked both of her nipples between his fingers.

"No one is going to bother us here. There's no one coming home" Jack whispered in Kate's ear.

"I know. I like that" Kate replied, as she continued dancing slowly against Jack's body. "And I love you" she said again. She wanted to say it over and over again.

"I love you too, Kate. I should have told you a long time ago. I've loved you for so long" Jack said holding her by her waist.

"Is it bad that I wish we'd started kissing and stuff years ago? I feel like we've wasted so much time, when the feelings were always there."

"No, that's sweet." Jack said, thinking about watching Kate's body develop over the years.

Kate turned back around in Jack's arms so that she was facing him. She moved her hand down and gently rubbed his cock through his suit. "So you like my new bikini?"

"Yes. Can't you tell?" he said laughing.

Kate rubbed his cock some more. "I'll kiss it, ya know."

Jack moved his hand down between his sister's legs and gently pressed against her mound. "I'll kiss you too."

Jack walked her back slowly towards the bed and laid her down on it. He was still standing by the bed, and he rolled her over onto her stomach. "Remember how you came into the room on that Saturday and asked me to scratch your back?" Jack asked as he moved his hands over her bare back.

"Of course. But I didn't know what was going to happen."

"Me either. That's part of what makes it so exciting being with you." Jack ran his hand down Kate's back, over her ass, and down her leg. On his way back up he pressed lightly between her legs. Kate let out a little moan.

She moved up onto her side and pulled down the top of his swimsuit, freeing his hard cock. She smiled up at him and gave his cock a kiss. Jack pushed the suit the rest of the way down and watched as Kate took him into her warm mouth. Jack had now shaved his balls and he found that meant that they would get a lot more attention from Kate. She popped his dick out of her mouth and kissed and licked his balls before licking the sensitive underside of his cock and putting it back in her mouth.

Jack wanted more. He slid his hand down Kate's body and inside her bikini bottoms. Kate opened her legs to him. Soon he was circling her clit as she blew him. Kate would look up at him while sucking him and that turned him on even more. Watching his mostly naked sister sucking his cock while he fingered her pussy was amazing. Kate was getting much better at this. Jack could feel his orgasm building and soon shot into Kate's mouth. Kate did her best to swallow his load, but his cock popped out and he shot the last bit on her chin. Kate gulped and laid back onto the bed with a smile. She loved making Jack cum. She used her towel to wipe the rest cum off of her face.

"That was so hot" Jack said, as he laid down beside her to give her a kiss.

"I'm glad you liked it. I think I need something to drink real quick though."

"I just gave you something to drink" Jack joked.

"Yeah, that's why I need this" Kate said reaching for the beer by the bed. She took a sip and laid back down. Jack's hand moved over her body. He cupped her tits and lightly sucked her nipples.

"I think I should show you how much I liked that blow job" he said, as he kissed his way down her body. Chill bumps covered Kate's small body as Jack's kisses moved below her ribs and down to her stomach.

Kate's favorite Peter Gabriel cover, The Book of Love, played in the background as Jack's kisses reached the top of her bikini bottoms. Jack continued moving down, kissing her through her bikini. He pushed her legs apart and moved between her legs. Jack kissed her sensitive inner thighs. He knew that this made her wild. Jack reached up with one hand and pulled at the string on one side of her bottoms, then he pulled on the other. He pushed her bikini down and away, revealing his sister's beautiful pussy. Kate could feel Jack's hot breath on her.

Jack licked Kate's wet slit. He kissed and then tongued her clit, causing Kate to put her hands over her face, then she reached out to grip the covers at her sides, as she took in the feelings.

"Baby, that feels so good" Kate said, as she pushed her hips up to meet Jack's tongue.

Jack was in his own world. He loved having Kate naked and horny. He tasted her wetness and listened to her moan as he felt her squirm under his tongue work. His hands roamed freely all over her naked form, and he remember back to when this was all just a dream of his that he jerked off to. Now he was living his fantasy.

He pushed her legs up higher so he could lick her ass. Kate held her legs up, not wanting any of it to end. She was moaning loudly now. He move back to her clit and pushed a finger gently into her pussy, opening her up with her own wetness.

"Oh, Jack. Stay right there. I love it!" She cried. Jack kept Kate happy with his tongue for a while. Jack had different plans though. His cock had grown hard again and he wanted to try something new. He began slowly kissing his way back up Kate's body. He stayed between her legs on the way up. He was up on his hands and knees as he kissed her on the lips. Kate could taste herself on his mouth.

Jack reached down with one of his hands and pressed the head of his cock against Kate's swollen and slippery clit. He rubbed is up and down in a slow motion that made Kate squirm even more, but she wasn't trying to get away. This was definitely against the rules.

Jack leaned down closer, putting more of his weight on her and continued rubbing his cock all over Kate's pussy, but staying focused on her clit. Kate was breathing hard. Jack broke the kiss and began kissing Kate's neck and worked his way up to her ear and whispered "I want to be inside you so bad."

Jack's words turned her on even more. She thought about living in the now. She thought about what she really wanted. She felt the amazing feeling of Jack's hot cock pressed against her pussy.

"I don't see anyone stopping you" she whispered back.

Jack pulled his face back a little and looked Kate right in the eyes. "What about your rules?"

"Different rules when at sea" she said, as she moved his hand away from his cock and opened her legs that much wider for him. Jack kissed her and smiled. He laid down onto Kate and slid his cock up and down her wet slit. He pulled back and let it line up with her little opening, then he pushed forward slowly. Kate's pussy opened to him. He made tiny little moves back and forth as the tip went inside her. Then he pushed in. Kate gasped as Jack entered her for the first time. There was a little pain. This was no finger.

"You ok?" Jack asked.

"Yes. Just go slow for a bit."

So he did. He moved in and out. He could feel Kate's wetness and warmth all around his cock. Kate loved the feeling of having Jack inside. They kissed and looked at each other, knowing that this was right. Jack sped up his movements and Kate lifted her legs into the air. They were making all kinds of noises together now. Jack reached around and held Kate's ass firmly as he pushed into her. He could feel her squeezing his dick as he moved inside her.

Jack was sucking Kate's tits again and he looked down between his legs to see his cock moving in and out of his sister for the first time. He could see some reddish coloring on his skin that marked the end of Kate's virginity. He looked back up at Kate, her head was back and her eyes were closed. She looked so beautiful. He kissed her neck and pumped harder, going deeper and deeper into his new lover.

"Oh, my God you're big!" Kate let out as she scratched at his back.

"You feel amazing inside" Jack managed to get out, as he was feeling another orgasm coming closer. He didn't want this to end too soon. He slowed back down and they stayed locked in a kiss for the longest time, losing themselves.

Kate put her lips to Jack's ear and whispered, "Go a little faster, baby." Jack did and this new rhythm sent them both to new heights.

"I'm going to cum, Kate."

Kate cried out "Cum inside me, Jack! I want to feel it inside me!"

Hearing those words pushed Jack over the edge. His body stiffened and he let out grunt as he filled his sister's pussy with his load.

Jack collapsed onto her and stayed deep inside her as they both tried to catch their breath.

"Wow. We really did that."

"It was amazing" Kate said, moving her hands up and down Jack's back. They stayed like that for several minutes. Jack finally pulled back out of Kate's warm hole. Kate made a funny face and said "Oh, my God" as he moved out of her. Jack rolled off to the side and Kate saw his cock was a reddish brown color. "Oh, my God." She looked between her legs.

"It's ok" Jack said, kissing her lightly on the cheek. "We're not virgins anymore."