Waking Up Pt. 01-02
Tem 20, 2022 // By:analsex // No Comment
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All characters in this story are 18 or older. The names have been changed to keep their secrets.
Part 1 – Growing Curiosity
Jack’s mom died when he was 13, and his dad was already in prison after being convicted of embezzlement. Jack never really knew him and didn’t really want to, but Jack did love his mom. Jack was lucky that his mom’s best friend loved her too, so she took him in. It was a no questions asked thing. Jack pretty much went straight from his mom’s funeral to his new home in a new small suburb. That’s when Jack first met Katherine, or Kate, as he would start calling her immediately.
Kate couldn’t come to the funeral, but she knew what had happened. When Jack first arrived she walked over to him and said “Everything is going to be alright. Let me save you from the grown-ups and show you your new room.” Jack was ready to get away from Kate’s mom after the long trip. Kate was like a new bit of hope in Jack’s destroyed world. She held his hand as they walked up the stairs. The upstairs had two bedrooms, a bathroom, and a large rec room over the garage.
“Here’s your bedroom” she said, waving her arm around. “And here’s the bathroom”, she said as she pulled him along further. It had two sinks on a single counter with a separate room with the toilet, a shower, and a bath tub inside. They kept going through the door at the other end of the bathroom. “And this is my room. So we’re connected, so you have nothing to worry about.” Kate really did have a way of making Jack feel at ease from the very beginning.
It didn’t take long for Jack to realize what a shared bathroom meant. On the very first night, he got up to pee, and when he was done he turned to see Kate standing by her sink in her pajamas. Jack had a somewhat shocked look on his face and she said, “Don’t worry. I already knew that guys peed too.” And that was how Jack started sharing a bathroom with Kate.
Kate’s parents started treating Jack like a member of the family right away, and by extension, that meant that they thought of Kate and Jack as brother and sister. Jack and Kate really never put that much thought into it, but they did like being around each other. They didn’t fight, and Kate helped Jack to fit in to his new surroundings. Those first years were hard sometimes, but Kate made things better for Jack and they continued to grow close. With the shared bathroom, there was some innocent walking in on each other, and a little curious catching peeks of each other in the shower. But the shower door and walls were made of a material that obscured everything inside anyway, so there wasn’t much to be seen there. Kate would take bubble baths sometimes, but it was hard to see much there either.
When Jack got older he started receiving money from a trust that his mom had set up for his education. She had also instructed in her will that he should at least try a boarding school that she thought was the best. So when that school year started Jack moved away. He missed Kate terribly. He missed her morning smiles in the bathroom. He missed seeing her in her thrown together bedtime outfits. He missed their watching tv on the couch upstairs alone together on Saturday. He missed the way she moved and the ease at which she could make him smile.
They talked on the phone some, but emailed even more. This is the way that the two of them really grew to know each other. Sometimes a person finds it easier to write stuff that they couldn’t ever say face to face. And as the emails continued, they became more and more personal. They talked about their future dreams, what they really thought of their parents, teachers, school, crushes, and pretty much anything that was going on.
When that school year was finally over, Jack planned on coming back and not leaving Kate again. At least for as long as he could manage. Jack feelings had grown for Kate during their time apart. He set the whole plan in motion by sending all of his info to a local school and asked to be enrolled. Jack slowly got Kate’s parents on board by making up some stuff about where he currently was. It wasn’t long before things were looking like they would go his way and he was ready to head back to living in the room next to his biggest crush ever.
Jack had only been home for a few hours and was still unpacking in his room when Kate came bursting in to give him a hug. It was the best welcome Jack could imagine. When they broke their embrace, she stepped back and he saw how she had grown up since he’d been gone. She had new curves and it was hard not to look, but he did his best. Kate began talking about how she had been at yoga and how great it was. That explained the leotard she was wearing that showed off her amazing body. Even though she had shorts on, the fact that she had a cute little butt was obvious.
Kate was very happy to have her best friend home. She wanted to tell Jack so much and show him so much. While a lot of stuff was the same, some things had definitely change. Kate pulled Jack into her room to show him her most recent decorating efforts. Her whole room was much less little girly now.
It wasn’t long until they had settled back into their old rhythms around the house. Kate would have normally pinbahis güvenilirmi been too shy around a cute guy to wear the things she wore in the bathroom around Jack, but since it was him, and this was how it had always been, she would wear stuff that would drive Jack crazy. Tops so thin that he was always glancing at Kate’s tits. Tiny shorts that seem to show more of her ass than they covered. And sometimes just big t-shirts and it was left to his imagination what else she was or wasn’t wearing underneath. For his part, Jack was almost always in his boxers when getting ready in the morning and when getting ready for bed. He didn’t even think about this being sexy to anyone, least of all Kate. Kate saw it far differently. To her, Jack’s body had changed and he had muscles and body hair that he didn’t have before. She even liked his butt, even if she didn’t know what all her feelings meant.
The first problem arose one night when Kate came bursting into Jack’s room one night with no warning. Jack was on his bed, but he wasn’t asleep. As she came in he closed his laptop really fast and turned quickly away from Kate, pulling the covers over him.
“Kate, you can’t just bust in here!” Jack said angrily.
“Why not? I always used to. What’s the big deal?” Kate said, wondering what she had done.
“Well, things are different now. I need some privacy sometimes, ya know.” Jack said trying to sound less angry so he didn’t have to explain anymore.
“Well, I just wanted to tell you…”
“Kate! Tell me later.” Jack said, losing his hidden erection as his embarrassment grew.
“Ok. Whatever.” Kate said as she retreated out of his room.
Kate wondered what big secrets Jack had that demanded so much privacy all of a sudden. She was wondering why he didn’t get up and push her out of his room. Then it hit her. Would he talk to her about stuff like that? They had emailed so many personal thoughts and she felt closer to him than to anyone else. And she knew that she could trust him and that they could keep each others’ secrets. This wasn’t going to be easy though. She couldn’t just walk up to him and say “So what’s jacking off all about?”. Kate knew about sex, but she had lived a very sheltered life going to a religious private school since elementary school. It’s not like her friends at schooled talked a lot about masturbation. Kate dozed off thinking about all of her questions and trying to come up with a plan to broach the subject of sex in general.
The next evening while both Kate and Jack were getting ready for bed Kate was dying to get Jack talking, but she still didn’t know how. Jack was trying to pretend that he didn’t care that his crush was right next to him in a tiny tank top and little pajama shorts that were cute as hell. He normally had pretty good control of things, but while he was brushing his teeth, he started thinking about what was under that top. His hard on popped up so fast, there was nothing he could do. Kate looked over to ask him something and saw the thing pointing straight out inside his boxers. Her eyes widened and she forgot her question, even though it was related to that. Jack’s face reddened.
“Sorry. It just happens sometimes” he said as he rushed out of the bathroom.
Kate wanted to say something, but she wasn’t fast enough. She guessed that he wanted some of his privacy now, so she went into her own room. But she really wanted to know a couple of things.
Jack couldn’t take it any more. The stuff that Kate walked around in when they were alone sent his mind racing. His hand was on his cock almost immediately as his head hit the pillow. Thoughts of Kate filled his head. Her tits pushing against the material of her top. Wondering what her nipples looked like, what it would be like to squeeze them while sucking on her nipples. Would she like it? Would she freak out?
He hadn’t been at it long when the door that connected his room to the bathroom opened and he heard a very quiet whisper, “Jack?”. It was Kate, of course. He could barely make her out as his eyes hadn’t adjusted to the darkness yet.
“Kate, we talked about this. You have to give me some privacy sometimes.” At least this was better than the last time, because it was completely dark in his room.
“I know. I’m sorry.” she whispered as she entered his room and gently closed the door behind her. “I just wanted to ask you something.”
Jack’s hard on wasn’t going anywhere. In fact, it was stiffer than ever with Kate in his bedroom now. Jack whispered back, “Ok, what was it?”
“Um, I um..” Kate stammered. Then she got it all out fast as if she couldn’t keep it in anymore. “I saw your thingie poking out in your boxers when we were in the bathroom. Was that because of me or something else?”
Jack didn’t respond right away. He was pretty shocked by the question. She had come in his room and kinda gone for it, so he decided to go with total honesty at this moment. “Yes. It was because of you. I couldn’t help it.”
There was total silence in the room. Kate had an answer to her question, but it was like she didn’t know what to do with the answer. Jack whispered, “Come over here so we can be quieter.” He made room on the bed for pinbahis yeni giriş her and Kate laid down next to him.
Once she was settled in she whispered, “So what’s it like?”
“What’s what like?”
“When it gets all pointy like that?”
“I don’t know. Why are you asking me this?”
“Because you’re the person that knows me best and I want to be the person that knows you best” Kate paused, then added, “And I want to know everything.”
“Yeah. I hear so much stuff at school and a lot of it doesn’t make any sense.”
Jack’s hard on was still going strong with this curious girl sorta in his bed, with him naked right beside her. He decided to find out just how curious she really was.
“I don’t know how to explain it. It just happens. I’m not always even sure what makes it happen.”
“Do you really want to know more?” Jack asked quietly.
Kate gave a soft, one word answer, “Yes” and moved even closer to him on the bed.
Jack reached down for Kate’s hand. She was lying on her side facing Jack, who was still on his back. He put his hand on the outside of hers and barely interlocked their fingers. He moved both their hands under the blanket, and towards his hard dick. He placed Kate’s hand right on it and slowly moved his fingers to get her to wrap her fingers around his dick.
Kate was amazed at how hot it was and how hard it was and how soft it still was. “Oh my God!” was all she managed. Jack moved his hand away to see what she would do. Kate used her finger tips to explore Jack’s cock. She went to the tip and then back down again. After doing that a few times, she went even lower to touch his balls. Kate was definitely learning something tonight.
Jack was in heaven with Kate touching him. He didn’t know how to make the most of it at this point though. “Well, what do you think?”
“It’s so warm” Kate replied. Jack decided that “It’s so big” may not always be a girl’s first reaction in real life.
“That feels really good…what you’re doing.” Jack encouraged her.
“It does? Show me how to do something.” Kate whispered as she gripped his shaft.
“Do like that and move it up and down a little.”
Kate did so. Jack let out a big exhale. It was the loudest sound they had made since she came into his room. Kate didn’t stop. She kept moving her hand up and down.
Kate’s lips were right up against Jack’s ear as they lay next to each other. Kate could feel a tingling between her own legs as she played with a cock for the first time. She let out a little involuntary sound of pleasure right into Jack’s ear. It was just a couple of “Ahs”, but it made Jack harder than ever.
“That’s it. Just keep the same pace…or change it…or…” Jack’s voice trailed off. He’d never been this far with a girl before. He didn’t know he would be getting a handjob from Kate tonight either. He looked over at her tits as they jiggled while her arm moved in rhythm. If she could touch his dick, then he should be able to look at her tits, right? His eyes had adjusted to the dark and he could now see the beautiful girl jacking him off.
Kate looked up at Jack and smiled. “It this ok?”
“It’s better than ok.” Jack’s breathing was harder now. He could feel the orgasm building up inside him. This one came without much warning and he began to shoot cum all over the blanket. He reached down and stopped Kate’s hand.
“Did I mess up?” she asked.
“That was amazing. You were amazing. I just came.”
Kate could feel some of the gooey stuff under the blanket. She pulled her hand out and tried to look at it in the darkness. She couldn’t see much of anything, but she smelled cum for the first time, and she could feel it slippery on her hand.
Jack caught his breath and smiled at Kate. “So it’s kinda like that.”
Kate giggled. “Yeah, why tell me when you can show me.”
“Something like that.” Jack whispered while trying to get himself back together. Kate push her face up towards him and kissed him softly on the cheek. “I’m gonna go before we get caught. I liked it.”
“What did you like?” Jack really wanted to know so he would be sure to do it again.
“All of it.”
And just like that, Kate quickly and quietly got off the bed and slipped back into the bathroom towards her room. She stopped off to wash the goo off her hand and for a quick pee. She pushed down the shorts and underwear she was wearing. After she sat down, she reached down to where she was tingling. She was wet and she hadn’t started peeing yet. She moved a finger quickly around and then pulled it away. “That’s new”, was her thought as she started to pee. As she got into her own bed she thought about what had just happened. “That was a handjob” she thought. She had given Jack a handjob. And he really liked it.
She kept going over it again in her head. She wished she had asked to see it. She tried to picture it in her head based on what it felt like, but she couldn’t. She would ask to see it the next time. “Oh my God” she whispered. She was already thinking about doing it again. And she wanted to kiss. Kiss a lot. Kate went to sleep that night with a tingly feeling between her legs.
The next morning pinbahis giriş everything was back to normal. There were a few extra smiles exchanged in the bathroom, but nothing was said. Jack liked it that way. Both wondered if anything like that would happen again, but neither knew how to make sure it would.
Part 2 – Trust
A few days passed quickly, as both Jack and Kate’s schedules were full and they didn’t always both stay at home because they both traveled for sports these days. What had happened in Jack’s room seemed more like an agreed upon experiment now, instead of some kind of hook-up. Jack wasn’t thinking about Kate as his girlfriend or anything like that. Kate was a little more full of emotion about this new thing that had happened, and she also wanted to play it cool because Jack was. Her “play it cool” plan was to look good for Jack, so that maybe she would make him hard again. But the truth was that she didn’t know what he liked.
One day she got lucky and sneaked onto Jack’s laptop when it was already open. Jack was big into passwords, so she didn’t have any idea what was on his computer even after living with him all this time. One of the items reduced down on the toolbar was a group of pictures. And not just any pics either. It was girls in bikinis and sometimes naked. She had found a little porn stash. “Naughty Jack” she thought as she smiled to herself and looked through the pics. Kate’s boobs were at least as big as most of the girls in the pictures, but how she was different was that none of them had any pubic hair. None at all. “So that’s what you like. I can do that” she thought. Kate tried to put the laptop back just as she found it and went back to her room. She had a full length mirror in there and she pushed her shorts and underwear down, revealing her patch of hair. She ran her fingers across it making a plan that she could get away with. Her mom probably wouldn’t need to know about this, but it wouldn’t be the end of the world if she found out either. “Bikini waxes are common, right?” Kate mused preparing her story if she got busted for some reason, but she really wasn’t sure how that would play out. It’s not like anyone was checking up on her pubic hair. She thought about the girls in the pictures. They were all beautiful and perfect and sexy. And they definitely weren’t virgins. So that’s what she’d really get in trouble for, if anything, is not looking like a virgin anymore.
The next day Kate had a friend drop her off at a day spa where she had made an appointment. The girl there was really cool and made Kate feel comfortable. She wasn’t surprised at all when Kate told her she wanted it all off. But, oh God, did it hurt. Once Kate was waiting back outside for her friend to come pick her up she was still feeling it. She wondered if she was crazy for doing this for a guy that might not ever even know about it. He was her brother! Well, not really. Not really even a step-brother. What was he? What was he to her in her heart? He must be something because she was making schemes to get naked in front of him or something. And she wasn’t doing that for anyone else. Kate was shaking her head as Liz pulled up.
“What’s wrong?” Liz asked.
“It’s nothing” Kate said with a smile. “I think I might be a little bit crazy” Kate said as they pulled off.
When the weekend finally arrived it meant that Jack and Kate would have the house to themselves as usual. They still hadn’t said anything about the night in Jack’s room. Jack was lying on the sofa in the upstairs tv room in his boxers and a t-shirt. This was what he’d done pretty much every Saturday that he could remember when he lived there. Kate looked in and saw him there, her mind working overtime. She couldn’t just go in there and start kissing him. That didn’t even make sense. But she was dying to. She wanted to know more. She wanted to see his thing. She would give him another handjob if he would only ask her for one.
Kate moped back into her room. Then she finally had a thought. Jack had already told her that just seeing her in the bathroom made his dick hard sometimes. So maybe all she needed to do was give him something to look at, and then he would want to kiss her. She quickly looked at herself in the mirror. She was wearing baggy pajama bottoms and a t-shirt with a couple of stains on it. That wasn’t going to do. She looked around the floor of her room for something to change into, since that’s where most of her clothes were, and she began to strip. Bra or no bra? She was trying to look like she just got out of bed and didn’t do anything special, so she went with no bra. She found a gray t-shirt that was the right length she wanted. It would come down to just the bottoms of the yoga shorts she was thinking about wearing. What if she didn’t wear yoga shorts? Her mind was racing now. She could feel the tingle between her legs coming back as she thought about wearing underwear only. After all, she just got up. She went over and looked through a drawer in her dresser. She quickly put on a pair of light blue panties with bands of pink lace. She stood in front of her mirror, holding up the t-shirt, trying to decide if this was a good or bad idea. She turned around and looked at her butt in the mirror. The panties weren’t see through or anything, but they were small and tight. In the front they were outlining every little detail. “That’s giving him something to look at”, she murmured softly. She had a plan. After brushing her teeth she headed back towards Jack.
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