My Stepsister Kylie Pt. 01

The following is MY story from elsewhere transferred here to literotica. This was actually my first story.

My name is Jacob. I'm 18 years old, I just graduated high school a month ago, and the summer is as boring as it'll ever be with my mom and stepsister. Little did I know, this was about to change.

We live in a middle class home in northern Georgia. My dad left my mom when I was five, and she married my stepdad four years later. I hadn't seen my dad ever since- not that that's a bad thing anyways. My stepdad is a 39 year old flight attendant so he wasn't home very often.

My mom, 38, had gone through several different jobs since dating my biological father. They were two dumb, washed up and horny young adults that winded up having me when they just simply weren't ready. She currently works at a bakery, making just enough for her and my stepdad to support us.

My stepsister Kylie and I got along pretty well. We were close growing up and then relationship just seemed to never die out until she went to college. She was one year ahead of me, and was back for summer break now finally getting to see me.

The first few weeks were pretty normal and as I said, pretty boring. It was a hot and quiet summer with nothing much to do around the house except to watch movies or play video games. The three of us tried to entertain ourselves with several activities but most of the time it just wasn't working. The story begins on a day where my mom is at work and my stepsister and I are watching a movie in the living room.

Kylie is lying on her belly on the sofa wearing a pair of leggings and an oversized t shirt- something comfy. Being honest with myself, she had gotten pretty hot since going off to college. Kylie has curly brunette hair that went down to below her shoulders, with a circular adorable pudgy face. She was about 5'7 with green eyes and a beautiful complexion. What was especially attractive about her, however, was her sort of slutty personality. College gave her the biggest confidence boost I came to realize in the days that she was now home. Kylie had been to plenty of parties doing who knows what. She had b cup breasts, so she wasn't particularly gifted there, but her ass is where this was completely different. I would catch myself staring at her cheeks jiggling as she walks about the house sometimes. Staring at her ass whilst thinking about this got myself admittedly pretty excited, and my gym shorts weren't hiding very much.

"You got any ideas?" She suddenly spoke up. I jumped up, taking my glance from her ass and back up to the tv. Luckily she still had her eyes on the screen and hadn't noticed anything.

"We could leave the house and go find something to do," I suggested.

"Like what? What the hell is there to do around here?" She said with a giggle.

"We could go get something to eat, we could go to the park, I don't know."

"You want to go shopping?"

I was hesitant because of my bank account but agreed. That's when she jumped up, turned off the movie, and nudged for me to follow her.

"You can help me pick out my outfit," she sort of demanded.

I sat there, a little confused at the sudden invitation, but curious. I stood up and followed her to her room, blessed by my no-longer-present boner.

I now lied on her bed as she changed outfits in the closet. After two minutes of waiting she emerged wearing a crop top with jeans and high heels. She stood there for a second before speaking up.

"Well? Thoughts?"

"It's honestly not the best, you could do better."

Kylie sighed, but nevertheless agreed. She returned back into the closet, but then opened the door again a few seconds later after she had changed her shirt.

"Still could be better. The jeans are kinda killing it for me, and you know you could change the shoes," I said.

Now a little irritated, she spun around and looked at herself in the mirror for a few seconds. She turned back to me and said "I'm just going to change out here. It'll save time and I don't think you care."

My heart skipped a beat at this, but agreed after a swallow. Admittedly it wasn't that big a deal, but she began to tease me a bit, knowing the situation she put me in.

Kylie turned away from me, to her closet, and slid her pants off to look for a different pear to wear. There in front of me stood her ass I found myself attracted to for the past several weeks, only covered by black lace panties.

I couldn't help it. Blood swelled to my cock as I watched her just stand there and look at the various options in her closet before her. She found a pair she wanted to try on and gave me a pretty frisky view as she jumped to help ride the next pair of jeans up her thighs. Her cheeks jumped up and jiggled slightly as they became swallowed up by the pair that was riding up her legs. Without realizing it, my cock was pitching a pretty noticeable tent in my shorts as the turned around to get my opinion. I looked up at her, and stuttered, "L-looking much better, just like I said, try a different pair of shoes!"

"Haha, okay," she said before looking at my bulging erection. "Looks like someone enjoyed the show," she said, smirking before turning away to look for shoes.

My face went as red as a tomato as I stood up to leave the room. "Sorry, that was stupid, I have to go," I said, panicking as anxiety filled my head. She laughed at me as I left the room and finished getting ready.

I retreated back into my bedroom with my raging hard-on. I tried to piece together what just happened as I pulled my shorts off, seeing my boxers littered with pre cum. "You're so fucking stupid," I said to myself. I was angry. I felt dumb. I was horny, sure, but this was an innocent crush I had on my stepsister that practically any guy would have.

I couldn't help but admit to myself, however, that I did enjoy what I just saw. As I thought about her black lace panties and the way she purposefully jumped to fit on her pair of jeans, I began to reach into my boxers and tug at my cock. Needless to say, I jerked myself off quickly seeing as we were leaving in a few minutes.

The shopping trip lasted for a few hours and we didn't say anything about what happened for several days. It was obviously a much bigger deal to me as it was her- considering she just thought it was a funny moment. I found myself fantasizing about her more often and catching peeks more around the house. It began to feel as if she might be teasing me sometimes as she would wear a t shirt with booty shorts as her leisure wear. The big event happened the day after my mom bought us some vodka to keep us entertained.

"So we're say drinkers now?" Kylie said to me as we took shots in the living room, again watching a movie.

"Rock bottom will take you to many different places," I assured her.

We weren't seriously even watching the movie. We made jokes and told stories. Our laughing grew more hysterical after we eventually downed seven shots after two hours. Mom was luckily working a full shift today so we didn't have anything to worry about there. The mood changed suddenly when Kylie stood up and asked me a bold question.

"Did you like my panties the other day?"

My heart stopped as I turned to her, my face flushing red. I took several seconds to answer, but the alcohol ended up speaking for me.

"They were unexpected, but nice either way."

She grinned and her eyes grew wide, obviously not expecting the response. She took another shot and turned to further the conversation.

"What's your favorite type of panties?"

Seeing as this question was more tame, I was able to answer a lot more comfortably, but of course with the added alcohol.

"Well I am a guy, so the less the better? I love a g string, but a thong would suffice."

"I agree with you completely," she said. After this, we just sat and watched the movie for a few minutes before she got up to pour one last shot before putting the vodka away, we obviously had too much- especially for day drinking. She was taking a few minutes more than anticipated and I began to wonder before she returned. Kylie did not sit down, but instead walked up to me.

"I have a surprise for you," she said, obviously sloshed.

"What could you possibly have now?" I asked, giggly.

To my shock, Kylie turned around and peeled her leggings off right before me revealing her ass yet again. This time, she was wearing a white thong.

My heart sped up as she stood, revealed to me just a few feet away from me. I hesitantly spoke up, "What are you doing? Don't you know this is fucked?"

"It's not a big deal dude," she said, turning only her head to me. She gave me an evil smirk as I lie there, again panicking staring at the sight before me.

"Are you nuts? Of course it is! Pull your leggings back up-"

"I know you like it, you shit head," she said, gesturing towards my erection growing in my shorts.

"Wether it excites me or not isn't the question-"

She interrupted me by jumping to sit on my lap, laughing too loud for me to calmly let anything out. She was wasted. I was getting there, but sober enough to tell how crazy this was. Still, it was making me kind of horny. I shoved her off me a few times, but she kept jumping back on to me, her leggings now have fallen to her ankles. After my sixth attempt, I finally just gave up and tilted my head back, ashamed.

Kylie calmed down and turned her head to mine, "stop being so lame," she said. "Let me be drunk and stupid- we'll just ignore this later anyways."

I didn't respond, keeping my gaze at the ceiling.

"Just be honest with me, am I hot to you? I don't care. It's cute."

I waited a moment before I finally looked at her and sighed. "Yes. Fine. But stop being a slut."

She grinned at me before slightly wiggling herself left and right.

"I can feel how hard you are," she said. "If you really wanted me to stop being a slut you would've stopped me by now."

I couldn't respond or say anything as I felt her ass rub against my shorts, my erection sliding against her cheeks. The situation was too much for me to handle.

That's when she finally stopped and got up, coming to the side of the chair on her knees to speak to me directly.

"You don't need to freak out so much," she said. "I'm only teasing you. Do you really want me to stop?"

I looked at her, flustered with emotions. I was going to tell her to never do it again, by I closed my mouth again, contemplating the situation. I was horny. She was throwing herself at me, drunk. I would regret this for the rest of my life if I weren't to take advantage of the situation. I froze a few more seconds before finally speaking.

"Stand up and turn around again," I told her.

She changed her endearing tone, to an evil, grinning one yet again. "I knew you'd cave," she said.

Kylie stood up, kicked her leggings off, and turned around, just several feet from where I was sitting.

"I'm not gonna let you rape me, just so you know." She said. "I'm only teasing you like this because I'm drunk."

I didn't care what she was saying, let alone pay attention. I kept my gaze fixated on her fat ass. Her cheeks swallowed the thong whole, giving me the illusion I was getting the full deal. I couldn't believe what I was allowing to happen, let alone the mental battle going on in my head. After half a minute of her just awkwardly standing there, she asked "you want me to do anything else? I'm not touching you."

Again, my heart sank just thinking of the possibilities. My mind clouded itself with so many fantasies I had to bite my lip so I wouldn't speak of. I wasn't sane anymore.

"Come closer to me. Lean against the side of the sofa."

"Okay, weirdo," she said, giggling as she backed up closer to me.

Her ass was now about a foot away from me. It seemed like time was unreal as I got lost in a trance. Her cheeks were luscious, I wanted to dive right in. I began to notice upon closer inspection that she was wet. The area coving her jewels was a slightly darker patch of white compared to the rest of the fabric. Turned on by this even more, I couldn't help but reach a hand into my shorts and grab my dick. I squeezed tightly, taking the strength I have left to not grab her ass and pull her back onto the chair with me.

She had been standing there for a few seconds more before speaking up.

"I can feel your breath yknow. You doing okay?" She hadn't noticed I was chocking my cock. She laughed by me not responding before giving her right cheek a playful smack.

This did it for me. I lost any sense of reality in this moment. She had gotten me so horny by that movement that I pulled my rock hard cock out of my shorts, completely out in the open, and started slowly stroking it. Obviously noticing something different she turned around, shocked for the first time. Kylie apparently didn't see the situation getting this far. She was going to say something, stopped, stuttered, then just stared at my dick. The very sight of it was so panic inducing yet so sexy at the same time, I just kept going. She scoffed, and turned to me, her face now red.

"So you're just gonna beat off to me now?" She exploded.

"What did you think was going to happen?" I said, now too far into the moment. She was now nervous, doubting I would've had the guts to do it.

"Are you sure about this?" She said, focusing back on my dick.

"I'm doing it aren't I? If you want me to stop just say so."

She was going to say something but caught her tongue again. She instead just watched me pump my seven inch dick for several seconds more before calming down.

"I just didn't think you'd be so open."

"Well you fucked me up and now I can't stop," I said.

She began to slowly fall into the heat of the moment as well, watching my hand rub up and down my shaft.

"Well you have a nice cock," she said, licking her lips. "And I can't believe I just said that."

"Well how far do you want to take this?" I said, hopeful the alcohol would seduce her more.

"I don't think I should touch it," she said, having a sense of sober ness. She now kneeled against the chair, watching my cock leak of pre cum.

I spent a minute or two letting her watch more before I spoke up.

"What if I just beat off to you then? Like you got back up and let me watch you more?"

She turned to me, as equally horny as I was now.

"I don't see much harm in that," she said. "I'll even lose the thong if you want me to."

The very thought of it took me to somewhere I never thought I would go to. I slid my shorts off completely, raising my cock just inches in front of her face. She pulled herself back, surprised.

"Pull then off. Let your stepbrother masturbate to your fat ass."

The words barely stumbled out of my mouth, but she slid off her thong, very much heated. This time, however, she positioned herself to stand directly in front of the chair, both legs positioned to the left and right of it. I lied back, stroking my cock slowly so not to cum too quickly. I was going to sulk up every second of this.

"I can't believe this is happening, but if you want me to do anything tell me or I'll do it myself."

I watched her before I replied, "spank yourself. Even squeeze your cheeks if you want to. You can finger yourself if you see fit."

In response, she slapped and grabbed her right cheek with the corresponding hand, user her left index finger to toy with her clit. "Glad I have your permission Jacob," she smirked.

I caught small glimpses of her pussy between her legs amidst her playing with herself. I spat on my hand, lubricating myself for the enjoyment. She began to moan as she played with herself, and the very sound of it only made me leak even more pre cum. I couldn't believe the situation I had gotten myself into. We couldn't stop now, it would be too awkward, so I just kept stroking myself. I eventually asked if I could grab her ass myself.

"No," she replied roughly, still playing with herself. "I don't think we should take this too far. You can smack it once, but that's all you get. Fuck this is so hot-"

I quickly obeyed her, letting go of my cock to swing my right palm against her. She squealed in response, making it even more hot. "You're a perverted little fucker," she said, "if we weren't siblings I'd want to eat your dick so badly right now."

"You CAN want to, you just won't allow yourself to," I said, hand now back on my cock.

"You're right," she moaned back. "I want to suck your dick so badly right now."

"Fuuuuck," I moaned, gripping my cock too hard. She turned her head to me, a hopeless expression on her face. I made a desperate request.

"We could 69," I said. "Nothing more, like you said. You could eat my dick while I eat your ass. Please let me eat your ass-"

"I want to hear you say that again," she interrupted, looking at me with hungry eyes.

"What do you want to do with my booty?" She giggled, giving it another smack.

"I want to eat it. Please let me." I let go of my dick, leaving her to make a decision. She stared at me for several seconds, having stopped fingering herself.

"You sure? There's no going back. We have got to keep this between ourselves, and never talk about it again. Fuck, I'm gonna have to distance myself from you."

Without giving her the chance to consent, I grabbed her waist, and thrust her onto my lap. Her pussy crashed above my cock, which was leaking a seemingly endless stream of pre cum.

"Fine," she replied.

Kylie used a finger to steal some pre cum from my cock, and gave the finger one good lick. She then pulled herself up so that she could position herself correctly. Kylie rest her knees on the arms of the chair, thrusting her ass against my face. I took a deep breath and grabbed her cheeks, spreading them apart. There I saw Kylie's dripping pussy and above it, her precious asshole. I stared for several seconds.

In the front, Kylie had rested her chest on my stomach (her shirt was still on) and grabbed the base of my cock. I could feel her teasing the head with her breath. The whole thing was too fucking hot for me to pay attention to my morals anymore.

"Are you gonna drive your tongue against your step-sisters asshole? Eat her pussy out?"

"Only if you're gonna swallow my dick right now," I demanded.

In response, she giggled over my cock. I couldn't help myself. I let one hand free and shoved her head down, her mouth engulfing my dick. I lied back, taken aback by the feeling and the wave of emotions. Kylie let out a muffled moan and she began to bob up and down, using her other hands to grab my balls or stroke my shaft. After a moment, she pulled my dick out of her cheeks, "you gotta follow suit with your promise too," she said. I hadn't even realized. "Whatever, just keep sucking my dick you whore," I said. "Eat your brother's dick like you wanted to."

Kylie licked the shaft of my cock before taking all seven inches back into her throat. I finally followed suit with my end of the deal by spreading her ass cheeks and guiding my tongue in circles around her asshole, kissing her cheeks slightly. Her asshole quenched in response, knowing how much I was teasing her. My dick felt it was in heaven as kylie's mouth suctioned every inch of it there was with her hot tongue and saliva. After toying with it for a few more moments, I finally thrust my tongue against her asshole, following suit by thrusting it inside. Kylie moaned it pleasure, swelling my cock seemingly further and shoving her ass against my face even more. I was now tongue fucking my stepsister's ass while she was taking every inch of my dick in her mouth.

We enjoyed this position for about twenty minutes, never stopping to say anything. Her butthole tasted so good to me, and she moaned endlessly- her mouth stuffed with cock. After realizing her pussy needed the attention, I pulled my tongue out completely, and changed my target to her that instead. In response to the sudden change, Kylie pulled my dick out of her mouth again to speak.