Family is for Fun Ch. 01: Jim

Thank you Chitranna for editing this writing.

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Life moves in ways you would never thought it would and sometimes a bad situation turns out to be a really good one. I guess it really all depends on what you make of it and when it happens. You learn and see new things every day and if you do things right, you experience things you never thought you would.

Let me tell you about the misfortune I had that turned into something that was a great experience for me, and experience that made me rethink so many things and opened up a whole new world for me to explore.

Last fall I went on a long road trip to go see some old friends and my sister, Gwyn, insisted she come with me as she had friends back home she wanted to see as well. I agreed, reluctantly at first, but I came to enjoy her company on the long trip as she was more fun with car games than I thought she would be. And we stopped in the night to grab a hotel, each paying for our own rooms giving us time apart throughout the ride.

That one night changed though. We had the misfortune of rolling into a town that had a convention going on and hotel after hotel had no rooms or only one room available to be used. Eventually we said fuck it, it isn't like we couldn't stay in the same room, just give us each a bed for some shut eye.

After putting our bags in the room we decided to head to the little bar in the hotel to grab a couple of drinks before we settled down for the night. It was a little crowded and a bit noisy, but we kept to ourselves and enjoyed a few whiskeys then headed up to the room.

When we went in the room Gwyn looked over to me and said, "Okay, I'm going to go shower and when I come out I need you to turn around. I didn't pack any pajamas so I will only be in my t-shirt and underwear and I don't want you to see me."

Fuck! Seriously? Like I would want to look anyway, but who doesn't pack pajamas on a road trip? I shook my head and laughed, "You got it Gwyn, you really don't have to worry about me looking, that's gross."

She threw a pillow at me and laughed, "Hey, I'm a sexy young woman dammit."

I caught the pillow and laughed, "Maybe for someone else little sis, not me. Go shower and warn me when you are coming out."

She skipped off to the shower singing she was too sexy for her shirt and soon I could hear the water running and I nestled up against the backboard of my bed and flicked through my messages.

It wasn't long before Gwyn called out for me to close my eyes and turn around and I did so quickly for her to jump into her bed. Once she seemed settled I excused myself so I could take a shower and change before I to headed into bed.

When I stepped out of the shower room I could hear Gwyn adjusting in her bed and I went to my own as quietly as possible. Sitting down against the headboard and pulling my phone back out I heard her moan and I looked over to her. Fuck! She was laying there with the covers off of her body, her shirt was lifted and only the thin fabric of her thong covered her ass. It may have been the whiskey putting the thought in my head, but all I could think of was what a nice ass was in the bed beside mine. It was crazy, I couldn't move my eyes from my sister's nice ass. I knew it was wrong to look, and even more wrong for my cock to lift as I viewed her, but, fuck! She was sexy, very sexy.

I fought myself to move my eyes from her beautiful ass, a far harder thing to do than it should have been, and looked down at the bulge in my pants. How could I possibly get an erection for her? How? She was my sister for god's sake. I flicked my phone to a site I liked to look at and started viewing other women, I had to convince myself she did not give me the hard-on, these other photos did, I had to.

Gwyn shifted again and then spoke, "What the fuck? Did you really uncover me?"

My eyes widened and I looked over to her, still uncovered but now propped up as she looked at me with amazement.

I stumbled on my words, for a few reasons, "Fuck no! I wouldn't uncover you. That's gross."

She shifted, which lifted her ass more for my eyes, I couldn't believe I was still focused on her ass, then pulled the covers over her legs and sat up, "How fucking drunk are you? Are you stroking yourself looking at me?"

I realized then that my hand had fallen into my PJ bottoms and it was very clear that I had been stroking myself. Slowly I removed my hand from my manhood and set the phone down so she could not see what was on my screen, "That's fucked up sis, there is no way I would stroke myself to you. No fucking way. I may be a bit drunk, but I would never take your covers off or stroke myself looking at you"

She looked at me quizzically and her eyes moved down to my crotch, my hard shaft clearly visible, "Then why the fuck do you have a hard on? Is that what you do with your friends, talk about me and have a circle jerk? Are you really thinking about fucking me Jim? How often have you made yourself cum thinking of me? Is this the first time you undressed me?"

Holy shit this was so wrong. The more she spoke the more my mind swirled with the thoughts she was putting in my head. I couldn't take my eyes off her sitting there like that, just the thin sheet covering her bottom half and a t-shirt covering her top. I wanted my cock to soften, but it got harder, "Holy fuck Gwyn, I wasn't doing anything and I didn't uncover you. I have never masturbated thinking about you, NEVER!"

She shook her head and pointed at my cock, "Really, than what the fuck is that?"

I shook my head and tried to remain calm. Why? Why the fuck would my cock not soften? "You have the wrong idea, it's not about you. I wasn't looking at you or anything. It was the porn I was watching."

Her eyes went wide, "The fucking porn? You were watching porn with me having my ass exposed right next to you. Fuck it! Pull it out."

I backed away, seeking the shelter the distance would give me, "What? No fucking way. I am not showing my sister my cock!"

She stood up, the sheets falling off her body and stared at me, fuck she was sexy! My eyes explored her body even with me trying to look away. There she stood, a tiny thong and a t-shirt covering her fit body, the light glow of a lamp illuminating her before me. She glared at me from her stance, "You got to see me, fucking let me see, prove you are not hard as a rock! Pull it the fuck out!"

I couldn't stop looking at her, she was sexy as hell. It had to be the whiskey. I screamed for my cock to soften, but it would not, it stood stiff as I looked at the forbidden woman in front of me, "Really Gwyn, I didn't look. How drunk are you? You really want me to pull my cock out?"

She nodded then pulled her shirt off exposing her tits and her hard nipples. Fuck! Was this really happening? She put her hands on her hips and kept her stern gaze on me, "There, I fucking gave you the full view that you wanted. Now, stand the fuck up and drop your pants, prove to me you are not hard as a fucking rock."

My mind swirled from the whiskey and the view was intoxicating. She was so sexy, but I was never supposed to see her like this. Her tiny thong the only thing covering her body before me. I moved forward and slowly stood up, "You really want me to drop my pants?"

She nodded and kept her lips tight before she spoke, "Fair is fair you fucking pervert. Shirt then pants, just like me."

I took a deep breath then pulled my shirt off and looked at her, "Good enough right?"

Her eyes widened, "Fuck you! Drop the pants, prove it to me, prove you were not stroking your cock."

I hooked my thumbs into my waistband and carefully slid them down my legs exposing my stiff shaft to the air between us. I couldn't believe this. I was standing before my sister, who was wearing just a thong, and I was naked with a full-fledged hard on coated with pre cum. How the fuck did this happen?

She licked her lips and let out a quick gasp, "Holy shit Jim! You're big! And look at it glisten. How long were you watching me?"

"I wasn't looking at you. Fuck! I wasn't doing anything like that." I tried to cover myself and she slapped my hand away.

She reached out and took a hold of my cock. I gasped and when I tried to pull away she squeezed it holding me in my spot, "You have a gorgeous cock, Jim. Listen, it's simple, you were jacking off over me, its okay, most boys think about their sisters, I know. I'm going to help you."

She slid to her knees and slowly stroked my cock, milking more pre cum from it. I was frozen stiff, my sister was stroking my hard cock and I loved the way it felt, loved having her hands on me. Was I wrong? Was this wrong? How many people really do this? How many guys enjoy the touch of their sister?

She slowly licked around the head of my cock and looked up to me, "You taste great. Don't worry, its oral sex and it doesn't count." She opened her mouth and slid my cock deep inside her. Fuck! The way she moved her tongue was amazing, I didn't care if she was my sister anymore. I wanted her to keep sucking on my cock, to keep licking and caressing me.

Her head moved fast as she sucked on me and when her fingers began to caress my balls I could feel myself edging closer to an orgasm, I placed a hand on her chin to remove my cock from her mouth and she smiled up at me, "Real women swallow." Then she was back on my cock, sucking and bobbing rapidly, her fingers lightly squeezing then caressing my balls. I let my hand fall on the back of her head as my orgasm built. Fuck, I was about to cum in my sister's mouth! And I did. I tried to keep my knees from buckling as my balls pumped thick stream after thick stream of my seed in to her throat. Fuck! I came hard!

She stroked and sucked me until no more came from the tip of my cock then removed me from her mouth and kissed the tip a few times. "Fuck I am so wet right now." She moved back and slid herself up onto the bed, her eyes locked on mine. Slowly she slid her thong to the side and pressed her fingers against her shaved pussy, "Lick me Jim, fucking make me cum like I made you, I need to cum."

I moved quickly, far more quickly than I should have, given who's pussy I was about to lick, but I had to, she was right, it was oral and that doesn't count. She moved her fingers and my mouth closed on her pussy, slowly I swirled my tongue over her clit then flicked down her folds and back up. I began to suck on her clit as I slid a finger deep inside her pussy, fuck she was wet!

Gwyn's body began to move, lifting her hips up to press harder against my mouth as I tongue fucked her, "I'm going to cum Jim, fuck I'm cumming!" Her pussy clamped and released my finger several times as I continued to finger her and suck on her clit. Her orgasm flowed from her, dripping down her ass crack and soaking the sheet. I wanted to keep sucking her forever when she lifted my face to look up at her, "Slide you cock against me, fuck I want to feel your shaft against me!"

I shook my head, I had to resist, oral sex is one thing but putting my cock against her pussy was completely different.

She pulled on the back of my head so I could look into her eyes, "Fuck Jim, please, please slide it against me, I love feeling a hard cock after I orgasm."

I stood up sliding myself between her legs and took my stiffened cock in my hand. I looked down to her as I began to run the tip of my manhood against her folds, slowly caressing her pussy with it, "Press the shaft against my pussy Jim, I want to feel it against me,"

I did as she wished, releasing my cock from my hand I pressed it against her and slowly moved my hips so my shaft slid against her folds and my cockhead teased her clit. Her legs wrapped around me and her arms held on to my sides, "Fuck yes, just like that big brother, holy fuck yes, I'm going to cum again, I'm going to cum on your shaft!"

I moved my hips faster, pressing my cock harder against her as her body heaved against me. Her hips moved with me, matching my pace when she grabbed the back of my hair and cried out, "Fuck me! Oh my fucking god fuck me hard!"

I didn't even think about it, I just pulled back far enough and slid myself deep inside her tight pussy and began to pump her fast and hard. She squeezed her legs around me tighter and lifted her ass to give me more access to her and I pumped faster, harder, my balls slapping against her and her moans began to echo in the room.

It was the most erotic and passionate sex I had ever had and when she cried out, "I'm cumming, I'm fucking cumming, cum in me, cum in me now!" I couldn't hold back. I filled my little sister with my seed as she came and I kept pumping it inside her like I had never done before. I pumped myself with her pussy until I lost my breath and collapsed on top of her.

We laid like that for some time, our breathing heavy, wrapped around one another. I gave her a small kiss and rolled off her then settled on my bed. What the fuck did I just do? I couldn't believe it. Why couldn't I stop myself from fucking her?

She crawled up beside me, kissed my cheek and whispered, "Now you can do more than jack off to me." She laid her head on my chest and we fell asleep quickly.

We got a few looks when we left the hotel in the morning, I guess we got pretty loud. With wry smiles we left as quickly as possible. Our road trip ended up being a great one and we shared a room every night after that.

I always look forward to our road trips now.