Some Time with Jackie Ch. 01

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"Hello!" I called out through the house as I got home.

"Hello John." My mom said stepping out from the kitchen, a ham sandwich with a bite out of it in one hand and her phone in the other. "You're home early."

"Half day at school today." I said dropping my backpack next to the door. That sandwich looked really good, so I decided to make one myself. "Why are you home?"

"Playing hooky. The office can survive for a day without their manager." A smile on her lips. "I hope." She added a moment later. "Maybe I should call Cheryl to make sure everything is okay."

"I wouldn't worry. Cheryl knows what she's doing and can keep everything going for at least a day."

"I know, but..."

"Don't worry, the office won't burn down before Monday. Any plans tonight?"

"I know it won't and yes. I'm going out tonight."

"Anywhere fun?"

"Nope. What about you?"

"I'm hanging out with Jon tonight. It's supposed to be a game night." I said finishing my sandwich. "Where's Jacklyn?"

"Out with a friend, I think."

"Awesome." I said. My mom shifted from foot to foot like she had something to say, but couldn't think of how to say it. "What's going on mom?"

"Huh? Oh nothing."

"Something's bugging you, so you might as well tell me."

"I-l'm going out on a date tonight." She said like she was nervous that I would flip out. My dad had left us when I was eight and she had been single for the last decade. I think she was afraid a man might do something to us if she started dating sooner. "You're not mad are you?"

"Not at all mom." I said smiling. She was a beautiful woman. About five and a half foot tall with long black hair, almond eyes and a fit body. She was as all my friends called her, a milf. "I'm just glad that you're finally getting back out there."

"Thank you. I was worried you'd be upset." She said.

"Nope. Now go and get ready for your date. I know you must be excited." I said as I took the last bite of my sandwich.

At that she left the room to go try on some outfits. Jacklyn came storming in the front door a few minutes later, slamming and locking it as soon it closed. "Everything okay Jacky?"

I must have shocked her because she stopped mid storm and stared at me like I was a bear that snuck up and said boo. She was wearing a black jacket and t-shirt with a pair of cut up jeans. "Why're you home?" she asked walking into the living room and glaring at me. She had graduated a year ahead of me and was waiting a year before she went to college.

"Half day. Why're you home? Mom said you were hanging out with a friend."

She scowled. "I was hanging out with Katie, and she was acting weird. So I asked her what her problem was and she said that she slept with Brad." Her anger was causing tears to well up in her eyes.

"Oh, I'm sorry. Are you okay? Do you need to talk about it?" I chose my words carefully. Saying need was important, instead of want. No one wants to talk about a bad relationship, but they do sometimes NEED to talk about it.

"No and yes." She said cuddling up with me on the couch. "I don't know what to do. Katie was my best friend. And Brad was my first serious boyfriend." She was openly crying now. "I thought he loved me." She said and put her head into my shoulder. "I had a surprise for him for being together for a year next month, but it's pointless now."

I held her close and stroked her hair that came halfway down her back. It was black like my mothers with a dark red streak in it. "When did it happen? I know it's probably not important but..."

"Last week." She interrupted. "And he just acted like nothing happened. Katie said she got drunk at a party and the next morning she woke up and he gave her his number saying "If you ever want to go again, give me a call." I could tell she was scowling by her tone.

"I don't think Katie is to blame. She obviously feels terrible about sleeping with him. Brad on the other hand can go to hell." I said holding her close. Her hair smelled of green apples. She hugged me a little tighter. I could feel her small chest through my shirt.

"I don't know what to do." She said wiping tears from her eyes.

"Dump Brad, he doesn't deserve you. He never did." I said giving her my honest opinion. "I think you should forgive Katie. I don't think she meant to do it and she told you as soon as she could." I said pushing her hair behind her ear. Jacklyn and I had been close when we were kids. She was two years older than me. By the time I turned ten, I was just a hindrance on her social life. It felt strange for her to open up to me. She was cuddling so close to me and it felt so good.

"I just need to nap." She said pushing off of me. "Thanks John, I really needed that." She gave me a sad smile as she walked off to her room. I don't know why I did it, but I was watching her ass as she left the room. I shook my head.

A couple hours later I was getting ready to head over to Jon's when my mom called up to us that she was leaving. I came down stairs and she was wearing a black dress that showed off her curves spectacularly. The hem ran from her left thigh down to her right knee and she had a V-neck that showed off her cleavage. "You'll knock him dead in that mom."

"Thank you, dear. Don't stay up too late." With that she walked out and drove off.

A few minutes later I was walking out and I ran into Jacklyn again.

"You heading out too?" she asked. She was wearing a pair of tight black leggings that showed off her body in intense detail. I could see the way her muscles moved as she rocked back and forth from foot to foot. A thin strapped red top hugged her body showing off her curves, her breasts were an A or a B cup, but I couldn't be sure. She had a sad smile on her face like she was begging me not to go, but it was her eyes that got my attention. Her grey stormy eyes looked like they were on the verge of tears. Why was I feeling this way towards my sister. Love I can understand. Wanting to keep her safe and protect her as well, but this was in a different way. I had a stirring in my jeans that made me thank the lord I was wearing baggy jeans at the moment.

"I was going to head over to Jon's. He wanted to hang and he just got a new game I wanted to try out." I said, damning myself for feeling this way towards my sister.

"Oh, okay." She said giving me another smile.

"I'm really not in the mood to go though." I said nonchalantly. What was I freaking doing? "I could go pick us up something to eat if you want to hang out instead."

"But what about Jon?"

"I'll text him and tell him something came up. We can hang out next week."

"Okay." She said. "What about some Chinese?"

"You got it."

As I drove to the closest Chinese place all I could think of was how sexy Jacklyn looked in that outfit. I don't know why I was thinking of her in such a sexy way. She has always been my older sister that was just there, no attraction at all, but now it seemed like all I could think of was how perky her breasts were. I could clearly see her panties in those tight black leggings, white with little butterflies on them. I don't think she was wearing a bra because her nipples had stuck out like they wanted my attention. I shook my head. I have to stop thinking about her or I'll end up driving off the road.

I personally have never been very good looking. I'm a little under six foot with brown hair, hazel/green eyes and a runners body. But I never really had any luck with woman. I could talk to them, laugh and joke, but when it came to romance and relationships I kind of dropped the ball at every turn.

I was lucky enough to make it to the Chinese place and home without causing an accident. I readied myself before I went into the house. The last thing I needed was for my sister to notice and start questioning why I had an erection. "Foods here." I called out.

"Okay, I'll be up in just a minute." She said. Why was she in my room? We lived in a two story house with three bedrooms, three bathrooms and a basement. When I was about thirteen I declared I wanted the basement since it was just an empty space where we used to have a giant play room. I got half of it cornered off with a brand new wall and door so that I could have my privacy and I made the other half a gaming area so that I could play with my friends online. She hadn't been down there unless she absolutely needed something from me before.

"What were you doing down there?" I asked as I set out our food on the table. She had changed into a black button down blouse with the top two unbuttoned and a blood red skirt with black leggings underneath them.

"I wanted to see if we had any of the games from when we were kids down there. I found them and I thought we could play games and watch movies tonight." She said her eyes pleading.

"Like the sleepovers we used to have?" I asked skeptically.

"Exactly. It'll be so much fun. Please John?"

"Okay." I said a little too quickly I think. The thought of spending the night with her and the thought of being able to check her out throughout the night was getting me excited. It was about seven already so it would be quite a few hours before she would go to bed. Just before I got to thinking about anything worse my phone rang. It was mom. "Hey Mom, what's up?"

A few minutes I came back into the kitchen and sat with my sister who had eaten half of her chicken already. "Mom says that she is going to be out for the rest of the night." Her eyes seemed to perk up.

"Wow, that's awesome. We can play all night!" She said giddily.

"Well the thing is mom said the rest of the night, but the guy she's with asked her to spend the weekend with him. She sounded nervous, but I told her that if she did want to stay the weekend that we wouldn't mind."

"Mom deserves some happiness." She said a little sad.

"I agree, but so do you." I said finishing up my last piece of sweet and sour chicken. "So what do you want to do first?"

She brightened up again. "Well I figured we could play goldfish and war. Then we could watch a movie." Her eyes bright and focused on my face. Her chest was pushed against her top and it was hard to keep my eyes focused on her face.

"Let's play war first." I cleared the table and she ran down stairs. I stayed up there for a few moments to calm my thoughts and erection down. She looked so sexy, but she was my sister and I couldn't be thinking about her in that way. I really needed to relieve myself of this uncomfortable pressure that was building. I walked downstairs and headed straight for my bathroom. "I'll be out in a minute."

"Hurry up. I wanna play." She said in a teasing whine from when we were kids. She had lit the fire next to the table where she was setting up.

I waved her off as I closed the door. As soon as it was closed I dropped my pants and boxers and sat on the toilet. I started stroking my cock slowly, I knew it wouldn't take long for me to cum. I couldn't stop thinking of my sister. Her tits pushing against her shirt, her nipples hard as ice. I wondered if she was shaved, but I figured she would be sporting a bush. She just seemed like the kind of person who kept it untamed for the hell of it. Her pussy lips would be poking out just a bit, so wet and kissable.

Just as I was about to shoot off my sister knocked on the door, scaring me. "Hurry up John, I'm bored." Well the good news is she scared me enough to go from the brink of climax to flaccid.

"I'm all done, I'll be out in a few seconds." I said as I redressed and washed my hands. "Okay, let's play." Knowing my sister, she set up the deck to play to her advantage so that she could win on the first round. She split the deck even and handed me the bottom half. I sat on the ground in front of the coffee table across from her.

"Want to make a wager?" She asked.

"What kind of wager?" I asked skeptically.

"If I win, you have to watch whatever movie I choose with me. If you win, you can make me do one thing for you."

"Sounds sketchy. What movie is it?" I asked.

"No clue, I'm going to go on Hulu and see what they have if I win." She said smiling.

"Interesting, but what would I make you do?" I said, pondering.

"Anything you want." She said pushing her chest forward giving me a better view down her shirt. I don't think she was even aware that she was doing it.

"Deal." I said even though I knew that winning was impossible. Five minutes later she was taking my last card from my hand and smiling from ear to ear.

"Yay!" she cheered. "I want to watch a scary movie." She stretched out her back by throwing her hands up in the air and leaning back, thrusting out her breasts towards me. Her hair was tied back in a pony tail. I sat on the couch and handed her the controller to choose a movie. She chose an older movie that was good but cheesy. So not too scary. Then she sat next to me and laid down with her head on my lap. I could see down her shirt a bit and I saw that she was wearing a blue bra with lace. Controlling myself was getting hard. I focused on the movie after a moment of staring because I felt myself getting hard. I hoped that she wouldn't notice my half erect cock.

About twenty minutes into the movie I was starting to nod off and she noticed my eyes starting to droop and popped up and paused the movie. "Wanna play another game?" she asked.

I yawned. "Sure. What game do you want to play?"

"Well I want to finish the movie. So I figured we could play the quarter game." She said taking a quarter off the coffee table.

"What's that?"

"Well, you're going to wait here and I'll be back in a minute."

"Okay." I said as she walked off to the bathroom. I stretched out a little bit in an effort to wake up.

She came back in and laid down on her stomach with her head back on my lap. "Okay, so I hid the quarter on myself and you have to find it. I don't think you'll find it though." I stared at her and she turned her head to the tv and continued the movie. It felt awkward that I had to feel up my sister to find a quarter in a game. I definitely wouldn't be able to control myself if I started to feel her up. I didn't know where to start.

I started on her arm and felt my way up to her shoulder and accidently tickled her in her armpit. I did the same with her other arm with the same result. It was a small target to find, so I was moving slowly and massaging every inch looking for it. I started moving down her back from her neck and shoulders, passing over her bra straps, down her spine then her sides. I felt it on her hip right at the edge of her skirt. "Found it." I declared

"I don't believe you. Prove it." She said without taking her eyes off the movie.

I stared at the back of her head with a shocked stare. I knew there were two ways I could get to it. One, have her roll over and unbutton her blouse to grab it. Or two, pull her blouse from out of her skirt to retrieve it that way. I controlled my lust and I went with option two. I gently tugged on her shirt and she wiggled a little to let it be pulled out. I grabbed it and showed it to her. "Got it."

"Okay." She stuck her tongue out at me. "Your turn." She said as she sat up and I walked into the bathroom.

Where could I put this thing, I thought to myself and I wasn't talking about the quarter. My erection was harder than a rock. I couldn't go back out with it standing like a flag pole. She would see it immediately and I didn't have time to deal with it. I stuck it in my waist band to hopefully let it die down without being seen. I decided to put the quarter in my right sock, hoping she would find it quickly.

I came back out and laid down on my stomach. She straddled my back and started feeling up my head, rubbing my hair, massaging my ears and neck. I was wearing a T-shirt so she ignored my arms and started rubbing my shoulders and back. She ran her hands along my sides and down my hips up to where she was sitting. The pressure was building beneath me as my cock got harder and harder with each passing second. When she decided it wasn't on my back she turned around and started feeling up my ass, slowly and attentively since I was wearing jeans. I hadn't expected her to feel me up so thoroughly. She put her hands around my left leg and started massaging there. She brushed against my testicles a few times before moving further down. I couldn't even pretend to focus on the movie. I was as hard as I had ever been in my life. I wanted to flip over and fuck her on the couch so hard and for so long that she wouldn't be able to walk the rest of the weekend. She got to my ankle and after a moment switched to the other leg, thankfully starting at the ankle first.

"Got it." She declared as she laid on my back and held the quarter in front of my face.

"Damn, I thought you would never find it." I said sincerely. She hopped off my back and ran to the bathroom to hide it again. I sat up convinced that if she laid on my lap again that I'd cum so fast and hard that she'd feel it through my jeans. She came out all fixed up again and laid on my lap. Her head pressed against my crotch and almost made me cum from the feeling of her warmth on it.

You'll never find it this time." She said teasingly. Her arms once again were without the quarter as I massaged them all the way up to her shoulders. I wondered to myself how far she would go to hide the quarter, and how far would she let me go in exploration in search for this quarter. Feeling her up in clothes was one thing but if she hid it on her ass or her tits, would she let me retrieve it from her.

I doubt she would hide it somewhere so perverse, but she had felt up my ass a great deal in her search for the quarter.

I shook my head and started moving my hands through her pony tail. I massaged her ears and neck in search of it and she let out a small moan once I got to her shoulders. I moved along her back as I carefully searched and massaged her. I felt along her bra strap to see if it was hidden beneath the band and down her sides. Once I got to her hips I took a few moments to massage them and she started to wiggle underneath the touch. I sighed. She stuck her tongue out at me. "Knew you wouldn't find it."

"I'll find it, you just have to move up a bit to I can continue my search." I said defiantly. She moved up and laid down again in an even worse position. Her ass was across my lap with my erection poking into her hip. She had to be feeling it right now. She didn't mention it.

I started feeling her feet and in between her toes in search for it. I massaged her left foot up along her ankle and slowly up her calf, caressing every inch of the way. She let out a small sigh as I worked my way up. I felt up her left knee and right above it laying gently on her thigh was the quarter. Now the problem was I had to get the quarter. Again I had two options. I could either lift her skirt up to her waist and stick my hand down her tights. Along her ass, feeling how firm it is and how hot she may be or I can pull down her tights and take the quarter by undressing her.

I couldn't do it. It wasn't right, but I was already moving my hands towards her waist. I decided undressing her might be less sexual for my sake and I started to pull her tights down. She wiggled her ass and rubbed against my erection by accident so I quickly pulled them further down her legs. I had accidentally pulled her panties down along with the tights. Purple butterflies on white cotton sat right below her skirt, obscuring any view that would've been revealed. I quickly pushed her panties back under her skirt averting my gaze. Kind of. I took a quick peek but her skirt was covering her again. I pulled the leggings down far enough to grab the quarter. "Got it." I said.