Waking Up Pt. 03-04

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

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Part 3 - When Flirting Turns Fun

Kate made it through shopping and most of lunch with her mom, Amanda, and her friend, Sasha. They wanted to stay in the restaurant and keep drinking wine, so Kate made her way back into the mall. She was thinking about what she could buy that Jack would like. She needed to think about some things that she never had before. She was thinking about Jack non-stop now. She now finally understood what some of her friends were going through when they just kept talking about some boy.

She got out her phone and started texting.

K: So did everything calm down there after I left?

J: Everything is down now. I had to stop thinking about this morning though.

K: So you've already forgotten all about me?

J: I wouldn't go that far.

Kate was in a dressing room now. She stripped down to her bra and panties to try on what she had picked out. She stopped and looked at herself in the mirror. She was wearing a nice matching set that were mostly white and had little pink flowers all over them. She picked up her phone and did something she never thought she'd do - she took some pictures. It took a few tries for her to get one she liked. She loaded it up, held her breath, and hit send.

K: Everything still down?

J: No.

J: You're amazing.

To Jack, this did seem like something a girlfriend would do. At least, he had always wanted a girlfriend that would do something like this.

Kate took off her bra and put on a small, tight, pink tank top with thin little straps. It was designed to leave the mid-drift exposed. She took another pic and sent it to Jack.

K: Should I buy this?

J: Yes!

J: You can only wear it like that around me though.

That made Kate laugh. She thought more about kissing Jack earlier and how gentle he'd been with her. She wasn't afraid to do things for him that she would never do with another guy. Kate looked at the time and got dressed. She needed to hit one more place, but it was a long walk from where she was.

K: If you could do anything to me, what would you do?

Jack stared at his phone. Looking at the pics was easy. This one was a little more tricky. He decided to stall for time.

J: You mean like while we were kissing?

K: Yes, silly.

Jack decided to go small, because he didn't want to freak Kate out. He couldn't really just tell her everything he had thought about doing to her.

J: I would pull that pink top off of you and kiss your boobs until you couldn't take it anymore.

Kate read the words. Then she read them again. She had a huge smile on her face as she continued to walk. Was this what it was like to be crazy about someone? No one had ever kissed her boobs before, but now it made perfect sense to her for Jack to try it. Then she realized that she was leaving Jack hanging.

K: That sounds nice.

J: Ok, same question to you.

Oddly, this wasn't even difficult for Kate. She had been thinking about it for a while. She was feeling bold now too.

K: I want to see your thing while I'm giving you a handjob.

J: That's big talk from such a little girl.

K: Hey!

J: I think I can make that happen. Can you make mine happen?

K: I'll see you soon and we'll find out who means what they say! xoxoxo

J: I'll be around.

K: I've got to go find the 2 buzzed women I'm with. cya.

Kate pocketed her phone and headed back towards the restaurant. So how was this going to happen tonight? Her heart beat a little faster just thinking about it.

Kate's parents names' were Kevin and Amanda. Jack had always called them by those names, and Kate did sometimes too, but she also used mom and dad. Kevin owned a restaurant that Jack had worked in the kitchen of on and off over the years. Jack was good at it and now quite the cook as a result. Kevin was a hands on restaurant owner, so that meant he was almost always there. Weekends and holidays only meant more time spent at work to him. Amanda worked for a health care company and her work often involved entertaining doctors and their wives at night. This left a lot of time where Jack and Kate were home alone.

That night was no different from many others. Kevin would be out until after midnight, and Amanda would be gone for at least four hours for her work. Kate had briefly popped her head into the rec room where Jack was on his computer when she got back to the house and said "Hey". There was no talk about the texting earlier. Kate headed off for the shower. Jack made them both some dinner later and they were eating it upstairs while watching tv together when Amanda called up to say she was leaving.

"You two be good tonight. I expect the tv to be off and lights out when I get back", Amanda called.

"Okay, mom" Kate replied.

Jack was really hoping that the lights would be off for a long time before Amanda got back. He wished he could read Kate's mind.

After the show they were watching was over, Kate got up and headed for her room. "I'm going to get ready for bed", she stated as if there was nothing special going on tonight at all.

Jack took their plates and glasses back downstairs, but rushed back up to also "get ready for bed". Whatever that meant tonight. He decided that he should act like it meant the same thin as any other night.

Kate was in her room with both doors closed. She was standing naked inside her big closet. She pulled out her new pink top and matching pink underwear. "I hope I know what I'm doing" she said softly, as she slipped on the new purchases. She stood briefly in front of the full length mirror in her room. The top was made of thin stretchy material and clung tightly to her body. Her mid drift was completely exposed. Her pink underwear had white lace borders and a tiny bow in the middle of the lace. She brushed her hair a few times and heard Jack enter their bathroom. It was time to brush her teeth.

"If this doesn't get him pointing out in his shorts, then nothing will" she said to herself and she opened up the bathroom door. Jack was already brushing his teeth. He was in his boxers only, as always, and his head turned to look at Kate when she came in. Jack stopped brushing and mouthed the word "Wow" and then came back to his senses.

Kate started brushing her teeth. Jack watched as her tits jiggled with her motions. It was the same top from the picture she had sent him from the dressing room. He kept looking at the impossibly thin material of her panties. That was all that was between him and what he really wanted. It wasn't lost on Jack that Kate was wearing this ensemble for him. That may not have been true every night of their growing up together, but it was true tonight.

Kate turned off the sink and looked over at Jack staring at her. "Is there something I can help you with?" she said with a devious smile on her face. She was also looking him up and down and taking him all in.

Jack took the two steps that separated them quickly and asked "Yes. Do you think I need to brush my teeth some more or is my breath ok?" He kissed her full on the mouth and wrapped his arms loosely around her waist. Kate stood frozen, but she definitely was kissing him back. When the kiss finally broke off Kate said, "I think you're fine. No more brushing."

"You look amazing. Live is much better than the picture" Jack said smiling at his little sister.

"I was hoping you'd like it" Kate said as she stood up on her tippy toes for another long kiss. Jack's hands moved down to her ass and she wrapped her arms around his neck. It wasn't long before Kate got the big reaction she wanted, and she could feel Jack's hardness pressed against her. She couldn't believe how turned on she was already.

Jack broke off the kiss and took Kate's hand, leading her into his room. She moved ahead of him and jumped onto his bed. She bounced on her knees as she turned towards him. Jack watched as his hard on continued to grow. He wasn't even trying to hide it now, like he had so many other times before. Kate smiled and her tits bounced as she kept bouncing on the bed. Jack reached for the light switch and killed the overhead light.

"Hey! Now I can't see anything" exclaimed Kate with some disappointment in her voice.

"Don't worry. I'm a man of my word" Jack said smiling as he turned on the lamp on his nightstand to the lowest setting. Now there was a bubble of soft light surrounding the two of them as Jack joined her on the bed on his knees.

They interlocked their fingers and leaned in for another kiss. Kate was nervous, but was trying not to show it. She'd never done anything like this before. The only thing that made her feel better was that she trusted Jack. He wouldn't try to go too far with her.

Jack wasn't nervous at all. All he felt was happy. Happy to have his beautiful crush in his bed. Happy that she dressed so sexy for him. Happy that his little sis wasn't upset that her older brother wanted her in this way.

Jack pulled Kate down in a playful wrestling move. She laughed and engaged in some mock struggle before he began kissing her again. Then the struggling stopped and Jack could feel the softness of her chest pressed against his body as their tongues danced in each others' mouths. He moved his hands up and down her body as they kissed. He pushed his hand under her top to stroke her bare back, and then would head back down over her ass and to her thighs. Kate's breathing became irregular with his exploring. She was feeling very naked, even though she wasn't.

It wasn't long until Kate made her own move. She ran her hand down Jack's side and on the way back up she lightly rub over his cock through his boxers. "So, is it my turn?" she said, trying to feel like she was gaining some control back over the situation.

"Ladies first, huh?" Jack smiled at her.

"Of course!" Kate laughed as she continued to feel his cock with the tips of her fingers.

"I guess you should take my boxers off if you want to see everything" Jack said as he rolled over onto his back.

Kate looked down at the tent in Jack's underwear and began scooting her body down the bed to get the right angle to pull off his boxers. She ended up sitting up so that she was hovering over Jack's waist. Kate gently lifted up the elastic waistband and tried to get it over Jack's hard cock.

"Grab it and move it down some" Jack suggested.

Kate put her hand inside and gripped Jack's warm cock, as big smile appeared across her face. She quickly cleared the tip and used both hands to then pull the boxers free. Kate looked at what she had freed for a few seconds before she took hold of it again. She gently tugged it up and down and she looked at Jack's balls.

Jack didn't mind Kate inspecting him at all. He had planned for it and trimmed up his pubic hair with his electric clippers just for the occasion. He hadn't gone all the way and shaved his balls though. That sounded too risky to him. Jack loved Kate looking at his hard cock, then back up at his face, then back to his cock. She was all smiles and giggles and full of wonder as she stroked him. She was sitting up with her legs crossed out of the way indian style and started to use both hands. Her fingers on one hand would feel around his balls while the other hand kept jacking him off.

"I like it" Kate announced.

"That feels really good."

"Tell me what I should do" Kate said looking up at Jack again. "I want to be doing it right."

"Hold it up a little straighter and don't pull too hard on the down stroke" Jack instructed. Kate looked back at what she was doing and tried to make it perfect. The tingling between her legs had been growing for a while now. Giving her brother a handjob in the warm light was definitely having an effect on her body.

"Give it a kiss" Jack said softly.

Kate obediently bent down and lightly kissed the top of Jack's cock.

"Give it a French kiss" Jack pushed.

Again, Kate bent down. This time her tongue came out and swirled around the entire head of Jack's cock, as she continued her jacking motions. She was beyond turned on by this new turn of Jack giving instructions.

"Put the top in your mouth" came another command.

Kate knew what a blow job was. She may have been inexperienced, but she wasn't stupid. She was about to give her first blow job.

Kate unfolded her legs and laid her head down on Jack stomach. She let his cock go from her hand and moved her mouth over it. Jack moaned from the new sensation.

"I can't see" Jack whispered after a few minutes.

Kate looked back up at him and moved her body around so that Jack could watch. She took his cock back in her hand, pulled it up straight and put it right back in her mouth.

Jack watched closely as his little sis moved up and down on his erection. The pleasure intensified with her jacking it again and with him watching. Jack's heart was beating fast and his breathing was hard. His hips pushed up towards Kate's mouth almost involuntarily.

Kate was really getting into it now. She moved around more between Jack's legs and pushed all of her hair to one side. One second she would be sucking away, then she would look up at Jack. The tingling between her legs had increased to something she had never felt before in her entire life. She tried to focus on holding her mouth just right.

She didn't have to focus for too long. Jack's body tensed and he gave her head a gentle push to the side. The second Kate released his cock from her mouth, cum shot all over Jack's body.

"Holy shit!" exclaimed Jack. He was out of breath.

Kate was breathing hard too. "How'd I do?"

"You were amazing! I didn't know it was going to feel that good." Jack tried to prop himself up on his elbows. He reached underneath the pillow next to him and produce a towel.

"Planning ahead?" Kate laughed.

"Well you did give me a heads up." Jack laughed as he cleaned himself up.

Kate crawled back up towards Jack's face. "Thanks for not doing that in my mouth. I don't think I'm ready for that."

"I wouldn't do that to you, sis. That wouldn't be fair on your first time." Jack said as he pulled her down towards him for a kiss. "I wouldn't do anything to mess this up."

"You made a pretty good mess!" Kate said, as she moved her hand across and down Jack's body.

"You helped" Jack said as he squeezed her tight and kissed her neck. "So ladies first, then it's the gentleman's pleasure."

"Ok, but I have to go pee first."

Jack reluctantly let Kate get up from the bed. She took a drink from the water bottle on his nightstand and disappeared into the bathroom.

Kate pulled down her underwear and couldn't help notice the wet spot that had formed. She rubbed her thumb over the slippery spot in her underwear and then move up to touch her pussy. She was soaked. She lightly rubbed her clit, and took in a deep breath, feeling its heightened sensitivity. "Oh my God." she said under her breath. She wondered if she was in over her head. She had loved giving the blow job though. She would never again think of another girl as a slut just for giving head. Kate peed, used a ton a toilet paper, and pulled her underwear back up. She got up her nerve again and went back in Jack's room.

"I'm glad you came back" Jack said smiling at her.

"You worried that I would kiss and run? I always mean what I text" Kate said. Then she crossed her arms, reached down, and pulled her top off in one smooth motion. Jack loved it. He was finally looking at the pair of tits that he had desired for years. Kate put her hands over her boobs and slid back into bed.

Jack got up on his side and slowly moved one of Kate's hands away and then the other. Kate relented and looked up innocently at her brother. He kissed her deeply as he touched her. This was different from earlier in the day. Now Kate was topless and he had full access. Jack slowly kissed his way down to Kate's left breast and kissed all the way around her hard left nipple as he gently squeezed her right breast. Kate inhaled sharply as Jack took her nipple into his mouth and began to suck it. She ran one of her hands into his hair and moaned softly at this new feeling.

"That's nice" Kate said dreamily.

Jack looked up at her as he moved from left to right and continued his kissing, sucking, and squeezing. Kate didn't want it to end. Her nervousness was gone and she loved the feel of her brother kissing her body freely.

Jack pulled her close and pulled her on top of him. They kissed again and Kate pushed her upper body up away from Jack to break the kiss. Then she slowly began to lower herself back down, but when she did, she put one of her nipples right on Jack's lips for him to suck. Kate slid her body down Jack's body and was soon being poked through her panties by his hard again dick. As Jack sucked her tits, she straddled him and began rubbing up and down. Kate was having all kinds of thoughts now. Jack pulled her back down again for more kissing and he grabbed her ass. He pushed his dick hard against Kate's panties, wishing he could push through them.

Kate was breathing hard. She suddenly thought that this was all getting out of hand. She moved off of Jack, but he followed. His hand moved between her legs. His fingers on the wet spot on her panties, and he pressed there gently. He kissed her again, and put his hand inside her panties. Jack loved feeling his sister's wetness from being with him. Kate opened her legs for her brother. She needed to be touched there - right now.

Jack did still sense some nervousness from Kate about him touching her pussy, so he moved slowly and gently. When he began making little circles around Kate's clit, she wasn't quiet anymore. She gripped the covers with one hand and held his head tightly to her chest with the other.

"Oh, Jack..." she cried. This only encouraged Jack further. He was pleased to be giving her this pleasure after what she had done for him.

Jack moved back up to kiss Kate again, but didn't let up his little circles around her swollen clit. He slid his arm under her neck and pulled her close to him. All the time maintaining the same motion inside her panties. Kate's body quivered as she made louder noises now. She wrapped her arm around Jack's neck and squeezed. She could feel Jack's hard cock pressed against her leg as her hips began to move with the motion of his fingers. This was way further than either of them had ever gone. This was further than she had planned going tonight, but her body was vibrating with new pleasures.

Jack move his hand around in a motion the take Kate's panties down. She grabbed his hand.

"I'd better keep those" she whispered.

"Why? I want you naked like me" Jack pleaded.

"I can't. It's just something...don't be mad", Kate said as she gently kissed him on the lips.

"I'm not mad. Not even close" Jack moved his hand back to Kate's wet slit. Her legs were more together now. He was sensing that he had blown it somehow. "Are you still, ok?"

"Yeah, it's just...will you hold me for a little while?" Kate whispered into his neck.

Jack moved his hand up her body and wrapped both arms around her. The feel of her warm soft tits pressing against him was amazing. He ran his hand through her hair and kissed her cheek.

"Thanks for today. This has been the best day of my entire life" Jack admitted.

Kate nuzzled in even closer to him and agreed with a soft moan. It was like she was coming down a little. Regaining something that she had briefly lost earlier. Finally, she spoke, "That was a lot of firsts today" then she giggled.

They laid there for a while. Kate was comfortable with Jack's cock pressing against her stomach, as he stroked her hair and bare back as they embraced. It wasn't much longer before they both heard the sounds of Amanda returning home. There was an audible sigh from both of them.