The Sibling Diaries Pt. 04

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Emily pushes the boundaries.
5.2k words
4.65
23.5k
38

Part 4 of the 7 part series

Updated 06/11/2023
Created 10/24/2021
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Author's note: This chapter has without a doubt the most sexual content so far. More is to happen with the other characters in the series but right now it's all about Alex and Emily! Hope you enjoy!

Character Sheet

Alex (Main Character)

Emily (Sister)

Melissa (Sisters Friend)

Brian (Alex's Friend)

Rose (Alex's Crush)

Mandy (Brian's Girlfriend)

Maddison (Cheerleader)

Brad (School Bully)

Benson (Head coach)

Mrs Willaims (Teacher)

Mr Bennett (Teacher)

The next few days Emily and Alex continued their Late night antics. He would come through to her room or she would come through to his. It's was nine o'clock on an Friday night. Nancy had had finished work early that afternoon. Her day had been long like usual so she made her way up stairs to bed.

She was happy that her kids were getting on so well. She couldn't tell you what had happened, but it was as if over night, Alex and Emily became almost inseparable. She could hear them giggling in the next room and she thought she'd peak her head around the door to say goodnight.

Emily heard the door click open and immediately she pulled her top down to cover her breasts. Alex was lying in bed while Emily was sat on the edge.

"Goodnight you two. Don't be up late now, I have work early tomorrow morning." She said.

"No worries, Mom. Goodnight." Emily said.

Alex said his good-nights as well. When the door closed they immediately got back to business. Like previous nights, Emily let her Brother stare and group at her naked tits.

She scooted up towards him in the bed, so that he could get a better feel.

His hands found her curvy tits and he played with them. He enjoyed the way his Sister would shut her eyes and moan softly whenever he paid close attention to her nipples. He quickly realised that she loved it when her rolled them between his finger and thumb.

"Okay, okay. Now you."

Alex lent back in the bed and fished his cock out from under his pants. The 6 inch raging erection stuck up towards the ceiling as he held it out for her to play with.

However this time Emily had something different in mind. "Why don't you play with it."

She suggested.

"Why?" Alex felt disappointed.

"I will touch it too. I just want to see how you do it. If you know what I mean?"

Alex knew what she wanted. She wanted to watch him jerk off. Alex figured why not? He took hold of his meat and started to play with the tip gently. He gripped it around with his fist and started to stroke it. Emily watched, more turned on than ever as she was witnessing her Brother beat his meat right before ever very eyes.

She watched how he would rotate his wrist more, how he didn't use much of his arm at all. For Alex it was all in the wrist, how he moved it made sense. It didn't take much effort and it seemed to be making him feel good.

"Wait, stay there. I have an idea." She said as she stood up from the bed.

Alex watched as his Sister removed her shirt completely. These days it was easier to go braless. Emily stood before the end of the bed as she brought her own hands up to her breasts. She cupped them in her hands and grabbed at them roughly.

Alex watched in awe of what Emily was doing. She was putting on a show for him. He started to stroke faster as his eyes were never leaving her breasts. She pinched her nipples and pulled at them. He made a mental note to tug at them next time he got his hands on her.

She watched his eyes follow her every move and it was electrifying to her. Just to know that she had his full, undying attention. When Emily moved here or there, his eyes would follow her.

She smirked to herself as her hands slide down her breasts to her stomach and then then to her shorts were she hooked the waistband with her thumbs. She tugged then down a little to reveal the beginning of her red laced panties underneath.

Alex could not keep his eyes off of her. He beat his dick faster than he normally would. He couldn't help it. Eventually she turned around to wave her ass around a little. He loved her ass. He'd never let on to it but he was indeed an ass man himself.

His Sister had that Skinny white girl ass that sort of stuck out all curvy and firm. He imagined what it looked like underneath the denim. She watched as her peach shaped ass waved from side to side. Her naked back was so attractive, her slender shoulders narrow into her thin waist. She had a little indent that ran from her neck down to her hips.

Emily turned her head back to check on him. He was really going at it on his cock now. She started to wonder what it would feel like inside of her, how it would feel pumping it that fast in and out of her. She felt herself dribbling in her panties. They would usually soak a little whenever they did this sort of thing but this time it was like a gush of her juices.

As she turned her head back around she closed her eyes and done the unthinkable. She sort of leant forwards to poke her ass out more and gripped the sides of her shorts. Alex gasped as he realised what she was about to do. She tugged at them slowly and Alex watched more of her skin come into view. There was her pink laced panties again.

Then a slight curve came into view. The beginning of her crack where her panties hugged at her ass was suddenly visible. Alex thought that this was heaven, that is until she hooked the waste band of her panties this time and pulled them all the way down to her heels.

Her ass was now bare for him to see and he took it all in. It was the best ass he'd ever seen. It was so round and muscular. it stuck out quite a bit. Her crack separated at the end were she had most of her roundness. Alex swore when she bent down he could see a little darkened spot where her asshole hid itself. He couldn't really see her vagina from here. She was too low to the ground and he was too high up to see underneath.

That was until she bent over fully. There, right underneath her cheeks were her lips. Two symmetrical folds of skin that looked wet to the touch. Alex came all over himself right there and then. He hit his chest, his abs and almost his face. He felt the hot liquid spray on him as his orgasm took over.

Emily whirled around to see the explosion for herself. He didn't see her move as his eyes had been shut in ecstasy. Suddenly she was under the comforter crawling up towards him.

"I can't believe how much you came!" She gasped when she saw how much white cloudy fluid was coating his chest.

"I can't believe how much you showed me!" He tried to catch his breath.

"Your ass is out of this world." He told her.

"Some people have said it's my best feature." She smiled.

Alex watched as Emily lay next to him. It was weird to see how her breasts flattened to the sides when she lay on her back. It then struck Alex that she was completely naked when her leg brushed up against his.

Alex had slithered out the bed to go clean up. Emily admired how soft his cock would get after such a big explosion. It kept a lot of its length but not so much it's girth.

"Will you pass me my panties? I forgot to put them back on."

Alex bent over and grabbed at her pink panties. He felt wetness against his finger. His hands were wet with a goo like substance.

"Did you eh... Climax as well?" He asked as he held out two wet fingers.

"Omg, Alex! Give them to me!"

"You'll have to come get them." He waved them around in the air.

"But I'm naked." She whispered.

"I'm sorry, am I supposed to care? Not like I haven't seen you naked before."

"You haven't seen all of me." She stated.

"I guess not. Maybe if you show me, I'll give you them back." He said.

"You want me to show you my... foof?" She asked.

"Your what?" Alex laughed.

"My foof, I call it my foof. It's a lot more polite than saying my pussy."

"We'll show me your 'foof' and maybe you'll get these back." He grinned at her.

"Alex, seriously..." she couldn't help but smile.

"Yeah, seriously. Did you cum in these?" He held them out with pinched fingers.

"No! It's just my you know wetness. It happens when a girl gets excited." She snatched them from his hands when he'd gotten to close.

"So you mean to say that your just as horny as I am?" He asked.

"Maybe even more horny." She stated.

"Then let me fix that." Alex had knelt on the bed as he approached her.

"No!" Alex stopped in his tracks.

"What do you mean? Don't you want to?" He asked her.

"It's not that I don't want to. Honestly, I've been needing it for days now. It's just, it's very much l a private place for me, I don't just show anyone my Pussy."

"I thought it was your foof?" He smirked.

"Foof, pussy, whatever. I just need time to prepare for something like that." She said shyly.

"Okay, how about tomorrow night? We can do it in your room, you can teach me how to?"

Emily kept forgetting that Alex was new to all this sexual stuff. He was a virgin after all.

"Okay, but you need to promise to listen to me. It's not as easy to get a girl to orgasm as it is for a guy."

"I promise." He held his hand against his heart.

"Okay, tomorrow night then."

Alex had agreed at school that day with Rose that she would come over around 5pm. He also found out that Brian and Mandy did the deed the previous night. He couldn't believe that Brian had lost his virginity before him. He supposed he was happy for him. He'd found someone he genuinely liked and although he thought that they were taking things a little too fast, he felt like they were a good fit together.

Mr Bennett had did his best to give Alex detention during third period but Alex kept his hands clean. He didn't backchat or say anything out of turn. He didn't want to have to phone Rose and cancel due to detention. That would have been much too embarrassing.

Emily had been away from Melissa for almost a whole week. She was due back to college in a couple days so they hadn't planned anything together. Instead they chatted on the phone for a good few hours that morning about what had been happening. She told him that she'd met a boy. She didn't say that thee boy was her younger Brother, but she did tell her about what her and said 'boy' had been getting up to.

"So when can I meet this, boy." Melissa asked.

"He's from out of town. He isn't around much. It's more like a hookup kind of thing."

"So, fuck friends?" She asked.

"Yeah, fuck friends." Emily agreed.

"Weird, considering you haven't actually fucked the guy yet?"

"Well we're taking it slow. You never know he might only want to do it once. Gotta keep em in suspense." They both laughed.

"I gotta tell you, Emily. Your Brother has turned out to be a stud. I'm on the school website right now and some of these basketball photos are just yum."

"You're looking at photos of my brother? That's weird Mel."

"No it's not. I'm looking at photos of my old school, your brother just happens to feature in a lot of the photos."

"I won't let you fuck my brother."

"We'll see about that." Melissa joked.

"I'm serious, Mel. You can't."

Melissa detected the seriousness of her tone and thought better to change the subject.

"So when are you gonna fuck this guy?" She asked.

"I wasn't planning on telling him, but I think I'm gonna let him do it tonight." She giggled.

"Oh good idea. See what he's made of. He might get a fright and chicken out."

"Let's hope he doesn't." Emily couldn't help but think about what it would really be like to fuck her younger Brother.

"Hey Me?, remember the guy we both fucked that one night that party? Well I have a guy I know who's looking for a threesome. Are you in?"

"I think I'm just gonna stick to this guy for now." She didn't think she could do that to Alex. Especially after the fact he told Maddison to find a new partner.

"Okay, well maybe next time?" Melissa asked.

"Yeah, maybe next time." Emily said.

"Well I gotta go. But I'll call you tomorrow so you can fill me in on all the details."

"Okay, byeee."

Alex walked Rose back to his house that day after school. The walk took about twenty minutes which kind of broke the ice for them both. They chatted about how they'd been friends when they were younger and now funnily enough were partners for an assignment.

"What you did to Maddison was exactly what she deserved." Rose said.

"Some people will say it's an opportunity missed." He joked.

"Must have been hard saying no to her?"

"Not really, I wanted someone that would help me with the assignment. Not help me lose my..." Alex was about to say virginity, but she hadn't known that he was a virgin.

"Virginity? It's okay I'm a virgin too." She smiled.

"You are?"

"Why do people act so surprised at that?" She crossed her arms.

"I think it's cos you're pretty and hung around with other pretty girls. Most of your kind have done it down by the lake or something."

"I don't have a kind. Im just a student trying to get to college, but good to know that you think I'm pretty." She said.

"Don't get so big headed Maddison."

"I am nothing like her." She screwed up her eyes.

"I know, that's why you're my partner and she's not."

Alex led her to the front door. He let her inside and she was immediately hit with memories of when they were young. Alex's parents would have her family over all the time for barbecues and parties. That's where they had become good friends as kids.

"I've not been here in so long." She said.

"Me neither, school dragged in today." Alex hit the couch.

"What are you doing?" She asked.

"Lying down?"

"We need to study. I thought you wanted to pass?"

"I do I'm just tired is all. Come on then. I'll show you my room."

Emily heard the front door close as she sat reading a book. She figured the other voice was Rose. She left her bedroom and caught them on the landing about to enter his bedroom.

"Hey guys." She said.

"Hey." Rose Replied.

"What you guys doing?" She asked.

"Just studying." Alex surveyed the look on her face.

"Just studying eh? Well remember to keep the door open. We don't want a repeat of Maddison do we?"

Rose laughed but Alex didn't find it funny. Together they entered his room and shut the door on Emily who was now laughing to herself. Rose let her eyes wonder about his room. She thought that it was very tidy for a teenage boys room. Everything was neatly placed in piles or stacks.

She enjoyed the photos on the walls but stopped when she got to the one that was in the centre of a large photo album.

"Hey?... Is that us?" She asked.

Alex got up to come look. She pointed at the picture and sure enough it was the two of them as kids. Both with with their arms around one another after playing in the paddling pool.

"I forgot that was in the album. My mom hung them up for me."

"We were so young." Roses head were filled with memories of that day. They used to be so close.

Alex noticed how fascinated she was by the picture of the two of them. Finally she moved in from the picture and decided to set her things down on his bed.

While Rose was sitting down Alex caught sight of something under the bed. He prodded at it with his shoe. His eyes widened. It was Emily's panties. She had forgotten to take them with her last night.

"Is something wrong?" Rose asked.

"Oh nothing." He tried to kick them further underneath the bed. "Just my some laundry I forgot to take care of.

Alex bent down to pick up the panties. He made sure to hide them from her view as he left the room. He scurried downstairs to find Emily watching tv.

"You forgot these last night." He tossed them to her.

"Omg! Did she see them?"

"Relax, she didn't see. That was a close call though."

"Couldn't you have explained that it was someone else's?" She asked.

"No. She knows I'm a virgin."

"You told her that you were a virgin?"

"I told her that I didn't sleep with Maddison, you know? The most popular girl in school? It was either I told her I get freaky with my Sister on a nightly basis or that I'm loser virgin."

"Suppose I'll have to go with Virgin on that one." She smiled.

Emily thought back to her conversation with Melissa. Perhaps that his virgin status wouldn't last though to tomorrow. She started to get excited the more she thought about it.

"When you're finished studying with your girlfriend, I'll be in my room." She called to him as he return back up the stairs.

Alex shut the door to see that Rose had taken off her jacket. She wore the same black jeans as she always wore with her old school converse. Her top was black too with small white stars.

"God she's beautiful." He thought.

"So what did you have in mind?" She asked.

"I thought we could write about ancient Egypt." He pointed at the postcards that were pinned to his door.

"What is your obsession with Egypt?" She asked.

"I don't have an obsession with Egypt."

"Well I heard you talking to Brian and Mandy about it a few days ago and you have Egypt postcards." She pointed.

"You pay attention to detail don't you." He said.

"No, it's just obvious you like it."

"Well how about you come up with something then Rosie."

Rose almost hadn't noticed that he'd used her old nickname that he used to call her. It wasn't exactly short but when they were kids Alex would always call her it. She didn't know why, he just did.

"Did you just call me Rosie?" She asked.

"No?" He hadn't even noticed that he'd said it.

"Yes, you did."

"Did I?"

"You haven't called me that in years." She said.

"Sorry, I think it just slipped out."

"It's okay, I used to prefer it anyway."

"I think we can just stick to Rose now though." He blushed.

For an hour or so they studied together on the topic that Rose had chosen. She thought that musical influence was the best thing to write about. So they wrote about famous artists and their influence on people. Rose researched a little about some singers back stories, while Alex made diagrams about what makes a musician influential.

"Can you throw me the marker pen?" He asked Rose, who was busy typing on her laptop.

Rose threw the closest pen to her left. Alex hadn't been ready for the throw and it hit him in the eye.

"Ahhh Rose!"

"Oops! Sorry." She laughed.

"What kind of throw was that?"

"I didn't mean it," she kept giggling, "I just meant to toss it."

"We'll toss better next time. Please, I like my eyes, I don't want to lose them."

"I'm sorry, maybe catch it next time. Thought you were good at that Mr Basketball player."

"I catch big orange balls, not stray markers."

"Here, you try." Alex tossed the marker and she barely got her hands up to block it.

In her retaliation, she grabbed at a pillow and threw it at him. Alex caught it and threw it right back. It hit her in the face and for a second he'd thought he had really hurt her.

"I'm sorry, I didn't mean to throw it that hard."

Rose was bent over clutching her face. What Alex though to be crying was actually her laughter. She gripped the pillow by the edges and swung it like baseball bat towards him. He didn't duck in time and the blow almost took him off his feet.

"That's it, you're done for now."

The two of them scrambled for pillows as they fought above heaps of scribbled paper and loose markers. She hit him with a few good shots before he returned fire. She lost her footing on the bed and Alex tried to catch her. Instead they both fell to the floor. Alex lay on his back with his limbs sprawled out and Rose landed on top of him.

The fall shocked them out of their little giggling episode. Roses face was now right next to his. He could feel her breath on him just like he felt Emily's before she kissed him. His eyes searched hers for some kind of signal or sign. The blue depths of her ocean eyes lured him in.

She closed her them and leant closer, as did he...

Suddenly the door swung open and Emily stood above them. She had a tray of snacks in her hands as she stood frozen on the spot. Emily couldn't believe that she'd left them for a few hours and now they were rolling around his room practically kissing one another. She remembered that she couldn't get jealous and she put on a smiling face.

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