The Weekend I Fucked My Sister - Cover

The Weekend I Fucked My Sister

by Highlander90

Copyright© 2026 by Highlander90

Incest Sex Story: This is a story about a guy who loses his virginity then fucks his step sister.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Consensual   Heterosexual   Fiction   Incest   Brother   Sister   Cream Pie   First   Oral Sex   Safe Sex   .

My hand trembled slightly as I reached forward towards the green bottle sat on the floor in the middle of our makeshift circle. I looked around at the faces seated around me, it was finally my turn and I knew whom I wanted to land on, Jordynn Hart. She was the girl of any eighteen year old boy’s dreams, her body very much developed ahead of our classmates, the ideal image of the girl next door. Eighteen like the rest of us. Blonde braided hair, blue eyes, sun kissed skin, beautiful smile. A slim body, nice full chest and a small firm ass. What I would do for it to land in her.

I took hold of the bottle and spun it. It seemed to spin at such a rate at first but then as it slowed it seemed to slow down time. I watched as it passed Jordynn, then again, then as it slowed it was turning towards her. My palms were sweaty and my heart was racing, I held my breath as the bottle came to a stop.

“Oh Jamie you got Jordynn” Demi announced. Demi was a pretty hot eighteen year old girl and one of my sister’s besties. She normally had brown hair but for this party she had dyed it burgundy. It was working for her, it gave her a completely new look.

My cock stirred in my pants as I involuntarily licked my lips at the prospect of kissing Jordynn Hart. Jordynn smiled briefly as she leaned forward onto her hands and knees. I did the same as we met in the middle. I had no idea what I was doing as this was very new territory to me. I’ve never kissed a girl before.

It lasted less than five seconds. Her lips very lightly touched mine before they were gone again. Even with this brief encounter my lips were on fire.

“What the hell was that?” Riley burst out.

“What?” Jordynn shrugged, “I kissed him.”

“Aww come on, that wasn’t a kiss. I know he’s my brother but geez.” She went on.

Yeah Riley was my sister, well technically step sister. My dad was a single father and her mother was a single mother. They met through a friend and quickly developed feelings. Well that’s the gushy story they’ve told Riley and I. They got married and we all moved into one house. So Riley and I went all through school together. Since we were so young when our parents got married, we basically grew up as actual siblings. Siblings that got on with each other as well.

Riley was actually the reason why I was here at Demi’s party. Well this was now the after party, the main party had already ended and a lot of people were sent home. We had a good relationship and she definitely helped with my social standing. She was pretty hot in her own right. A geeks wet dream. She was real book smart and often did cosplay. She nailed Lara Croft. She had the body for it and hair mind you. Dark brown hair, brown eyes, olive skin, long slender body with ample chest and round hips with a plump ass. Yes I’ve perved on my sister. I’m an eighteen year old boy, we think with our cock.

“Ugh fine” Jordynn rolled her eyes and moved back to me. I felt the palm of her hand on my burning cheeks as her lips met mine again. This time it wasn’t brief. Her lips pressed against mine as they opened and I felt her tongue brush against me. I parted my lips as her tongue ever so quickly swirled against mine before it retreated. Her lips smacked against mine several more times before she pulled away. It lasted under a minute but fuck it was epic.

“Better?” She shot at my sister.

“Knew you had it in you” my sister said to her before she flashed me a wink.

We played on. I didn’t get any luck as the bottle didn’t land on me with any of the girls, it had just missed me when my buddy Tyler had spun the bottle. It landed on Demi who was sat next to me. The other guys Brody and Spencer were a bit more lucky. I wasn’t sure if the girls would make the guys kiss as a couple of times the girls have kissed. Including Jordynn kissing her friend Natalia. Natalia was an eighteen year old Hispanic girl with black hair and dark makeup. Not going to lie, she was a bit intimidating and also super hot. Biggest tits here as well. Her cleavage was bursting out of the outfit she wore.

By this point it was fair to say pre cum was coating my boxers. The next one to go was my sister Riley, she spun the bottle and we all watched as it slowed right down at the girl next to me, Olivia. It didn’t stop at her.

“Ooooooo Riley you got Jamie!!”

“No way” I breathed.

“I’m not kissing my brother” Riley announced.

“Why you scared?” Jordynn teased her.

“Pfft hardly” Riley rolled her eyes. “Maybe the fact he’s my brother?”

“Yeah but aren’t you guys like step siblings or something, so it doesn’t really count.” Jordynn went on.

“Eh still not really the point” Riley argued back.

“It’s ok if you are chicken...” Jordynn goaded her.

Riley gave what sounded like a growl as she scowled at Jordynn before leaning over towards me.

“Surely not?” I whispered to her.

“Don’t make me look like a fool!”

As much as Jordynn was the girl of my dreams, her and Riley didn’t get on great. I couldn’t let her down.

“Fine” I sighed as I leaned forward towards her.

“Just close your eyes and pretend I’m someone else!” She said to me.

That was the first time I had kissed my sister and holy hell it did something to me. I tried to imagine it was Jordynn again but something deep inside me liked the fact it was Riley. Our lips smacked together and her tongue brushed against my lips but wasn’t as adventurous as Jordynn’s. I don’t know how long it exactly lasted but it was amazing.

“That was kinda hot” Demi muttered.

“It was ok” Jordynn mumbled.

“Damn dude” Tyler whispered.

“Right let’s not make this awkward” Riley said as she sat back down and I did the same. “Who’s next?”

“Leia is” Demi announced. Leia being Riley’s bestie. She was a petite eighteen year old redheaded girl. She might not have been the hottest to me but she was still a really good looking girl. I wouldn’t deny her a kiss anyway.

She spun the bottle and sure enough it landed on me.

“Two in a row.” Demi chuckled. “Lucky guy!”

Leia half glanced at my sister, who gave no reaction as Leia and I moved closer to kiss. Her lips were soft as we kissed. There was no motion from her tongue as she gently kissed me. There was something in the tenderness that made my cock twitch more.

I was on cloud nine. I’ve gone from never kissing a girl to now kissing three different ones. It was a weird feeling though since one of the girls was my sister. I was super happy with getting to kiss Jordynn and kissing Leia was nice but there was something inside me that enjoyed kissing Riley just as much. Maybe even more.

It came to my shot and with more confidence I took hold of the bottle and spun it. I watched as it spun and spun and spun and then slowed. At first I thought it was going to land on myself which would mean a re spin but it edged passed me and ended on Demi.

“You’ve got the star of the show” she grinned as she twisted towards me. I did the same and we kissed. It was quite sloppy as her tongue instantly forced its way into my mouth but I wasn’t complaining. It was my longest kiss yet but not my favourite.

We broke the kiss and returned our attention to the group.

“I need a drink” Jordynn announced as she got up and headed for bar. We were in Demi’s family basement which her dad had converted into a proper party place. It had a flat screen TV, music system, home made bar and sofas. It was great for hosting.

“Me too” Olivia added as she scurried after her bestie.

“I need the toilet” I said as I got up. I tried to quickly adjust the bulge in my pants when I stood and tried to hide it which was hard as Demi was right next to me at eye level.

I excused myself and headed up the stairs. I made my way to the guest bathroom which was on the ground floor of the two story house. I got in and shut the door, I quickly unfastened my jeans and pulled my cock out. I sighed in relief at the freedom gained. My cock was hard and rigid, the head glistened with pre cum.

I needed to get rid of this before I rejoined the others. I tried to pee but the tank was empty. I closed my eyes and tried to concentrate on anything non sexual. I couldn’t help myself and took hold of it and began to stroke. The last hour coming back to me and the feeling of their lips on mine flooded my mind. I groaned in delight as I worked my shaft.

I was completely lost in the moment when the door opened and Demi slipped in closing the door behind her.

“Demi what the fuck?” I tried to pulled my jeans and boxers back up.

“Holy shit, who knew you were hiding such a weapon.” Her eyes glued to my crotch.

“Demi I...”

“Sshhh” she hushed me. “I saw the bulge in your pants but didn’t imagine it being this big.” She stepped forward and with ease moved my hands away and took hold of my cock. I groaned in pleasure at her touch.

Demi grinned as her hand began to move up and down with my cock.

“I won’t last long” I breathed.

“Turn around” she told me and guided me to face towards the toilet. “Let me” she said as she now pressed her body against mine. Her hand working faster.

“Fuck” I groaned as her hand moved with purpose.

“God I can feel it pulsing in my hand” she whispered.

Moments later my body tensed as rope after rope of cum spurted out of my cock. Some of it made it into the toilet but a lot sprayed across the back.

“Oh wow what a load, all from kissing me.”

I didn’t want to correct her but this was hot as fuck.

She slowed her movements before pulling her hands away.

“We should totally do that again! I’m going to head back, you get cleaned up and I’ll see you back down there.” She gave me a tender kiss on the cheek before slipping back out.

“Holy fuck” I gasped as I composed myself. I quickly cleaned up, got redressed and headed back to the party.

“Great idea coming here dude” Tyler said to me.

“Would have been even better without Brody and Spencer being here.” He added.

“I know right. Spencer has been all over Jordynn.” I eyed up the dark haired flashy prep guy standing talking to Jordynn.

“Don’t worry man, he’s not got a chance” he patted my shoulder.

“Ok guys I’ve got an idea.” Demi announced. “We are going to change the game a little.”

“To what?” Natalia asked.

“Seven minutes in heaven.”

“Really Demi?” Natalia said.

“What? Ups the ante from just a quick kiss.” Demi said her gaze flashing at me.

“Sounds like fun” Riley said winking at her friend.

“Yeah why not” Leia agreed.

“There’s a catch though” Demi added. “It’s not just seven minutes in the closet. You get a room to yourself for thirty minutes.”

“One spin each until everyone has a partner.”

“So we only get one partner for thirty minutes and that’s it?” Jordynn said.

“Not scared are you?” My sister teased her.

“No!” she replied bluntly.

“Goody shall we start? Unless anyone else objects?”

“Dude, this could be your chance to get thirty minutes alone with Jordynn!” He nudged me.

I couldn’t hide my smile as we all sat back down again.

“Anyone want to go first?” Demi asked.

“I will” Riley said.

My sister leaned forward and spun the bottle. We all watched as it landed on my sisters friend Leia.

“Oh hey girl” Leia smirked as she and my sister got up and went to sit on one of the sofas.

“Next?” Demi asked.

“I’ll go” Brody spoke up.

Brody took his turn and it landed on Olivia, who blushed. Brody jumped up and helped Olivia up as they went over to an other sofa awaiting the end of the game.

“Right” Natalia said as she jumped in and took her turn. It ended up on Tyler. I could see her disappointment but he couldn’t hide his grin.

“Well may as well keep the order, boy next?” Demi said.

Before I had the chance to speak Spencer reached forward and spun the bottle. I took a slow breath in and held it as I watched the bottle spin. It was going to be either down to Jordynn or Demi. This was my best chance to make a move on Jordynn and ask her out. Again as the bottle slowed down, it felt like slow motion was kicking in again. I stared on as the bottle came to a stop at...

“Spencer you get Jordynn, which means I get Jamie.” Demi said with glee.

The smug look on his face made me want to punch him.

“Ok guys have fun” Demi stood up and took my hand. “Follow me.” She told me as I was dragged behind her. She took me through her house until we ended up in her bedroom. It was pink and very girly. She pushed me in and closed the door behind her, locking it.

“Wouldn’t want anyone walking in on us” she grinned.

“Well the last time it worked in my favour” I smirked.

“Aren’t you the funny one and a big one” she raised an eyebrow as she eyed up my crotch. “Think you’ve got another one in the tank?”

“Oh I’m sure I’ll be fine.”

“Good” Demi said as she closed the gap between us. Her body quickly pressing against mine as we kissed for the second time that night.

Again it was sloppy like before, it was hurried. It still managed to get me going though. My cock quickly grew in my pants as it strained against my boxers.

Demi’s tongue swirled around mine as her hand found my crotch. She moaned in our kiss as she grabbed my bulge. I groaned with pleasure at her touch.

“Mmmm you certainly feel ready.”

She lunged back into kiss as her hand gripped my cock harder. I let my hands roam down her body and went straight to her round ass. There was certainly enough for a handful each. It was her turn to groan into the kiss as I squeezed her ass checks.

We kissed for a little bit longer before she guided me over to her bed.

“Let’s see that cock again” she said as she basically pushed me back onto her bed. She fell to her knees before me and went straight to fishing out my cock. Moments later for the second time my hard cock was back in Demi’s hands.

“God it’s just as hard as before.”

I remained silent as Demi began to stroke up and down my length. It wasn’t as pleasurable as earlier as she tugged quite hard. She did this for several minutes before I felt her warm wet mouth cover the head of my cock. Her head quickly bobbed back and forth as she noisily slurped away.

“Fuck” I breathed as she took most of my length inside her mouth.

I gathered up her burgundy dyed hair as I watched on. Not that I was an expert myself in this area but I’m not sure Demi has given many blowjobs. I could feel her teeth now and again scratch down my shaft as she sucked me. Don’t get me wrong I was still loving it and wasn’t going to tell her to stop.

Her mouth continued to move up and down my shaft as it became slicker with her saliva. She went on for several more minutes before she stood up.

She had on a one shoulder pink dress which she slipped off her shoulder and then proceeded to pull the dress down her body. She bent down to take it completely off and as she straightened back up I was greeted with the full sight of her. Demi was now only wearing a matching pink floral bra and panties combo. My cock involuntary twitched at the sight which gained a giggle from her.

“Like what you see?” She posed in front of me.

“Who wouldn’t?” I told her truthfully. She had a decent sized chest which was squeezed together in her bra. She had an hourglass figure as her hips widened back out and showed off her round ass.

“Let’s get you out of those clothes too.” She reached forward and tugged my jeans and boxers off. She struggled to get them off as I still had my shoes on which she forcibly took off as well. I simply watched on, happy to let Demi to take the lead. Demi then pulled my t shirt off leaving me naked on her bed.

“Not bad Jamie” she said, eyeing me up and down.

“Not bad yourself” I replied lamely.

She blushed a little before reaching up behind her and unclasping her bra. I’ve seen tits before but never been this close. Demi caught me staring.

“You can touch them!”

I didn’t reply but reached forward and squeezed her soft mounds in my hands. Demi groaned at my touch as her eyes closed and mouth fell open with a gasp.

“I love it when I play with my tits.”

I played with them a little more before I looped my arm around her back and pulled her into me, immediately sucking her nipple into my mouth. My cock was absolutely rock hard, I’ve never gone this far with a girl before. I could feel the pre cum oozing out and leaking down my sleek cock.

“Mmm you know how to make a girl feel good” Demi groaned as I sucked her tit further into my mouth. My tongue lashing against her hard little nub.

Demi’s hand held my head firmly as I saw her play with her free tit with her own hand. I make a move with my hand on her back and slide it down to her ass. It’s soft to the touch and I squeeze it firmly with my hand.

“Uh god Jamie” Demi moaned as her body pressed more against me.

I was loving the feeling and experience of exploring my first female body but my cock was starting to strain in pain for release. As much as I felt Demi was up for anything, I was too nervous to make the move and felt more confident letting her dictate things.

My wishes were granted minutes later.

“Do you have protection?” She almost whispered.

I pulled away from her in an almost fear-like state, “shit no I don’t!!”

My heart began to race, I knew I was coming to Demi’s party tonight but I never imagined getting this lucky. My chances of having sex for the first time are quickly flying away.

“I have some” she breathed.

“Thank fuck” I whispered inwardly.

Demi pulled away and I reluctantly let her go. I was very much enjoying touching her and getting reactions from her but I was ready to lose my virginity.

Demi walked over to her bedside table and opened the small top drawer. She turned back to me with the small square packet in her hand.

“My ex boyfriend was a little smaller than you but it should still fit. Have you used one before?”

I could feel my cheeks flush bright red and I averted my gaze, “no” I simply replied.

“Jamie? Are you a virgin?” There wasn’t malice in her voice.

“Don’t laugh...”

“Why would I laugh?” She chuckled. “I’m surprised more than anything, I mean if the other girls knew what you had between your legs then you wouldn’t be one.”

“You aren’t bothered?”

“Oh baby no, it’s ok, we are going to change that anyway. Stand up for me.”

I did as I was told and stood up next to her bed. Demi came over and kneeled down before me. She tore the silver packet open and took the condom out. With a little effort she got the condom on and as she said it was a little smaller for me.

“Now I’m going to lie down, you get on top and get between my legs.”

Demi stood up and took off her panties before she climbed on the bed. Nervously I followed.

We got ourselves into position as I held myself up by my arms above her.

“Now I will guide you in but then it’s onto you!”

I nodded as I looked down as she took hold of my cock and pulled and guided me towards her. I lowered my hips as I felt my covered cock touch her. Moments later I felt the head of my cock enter her warmth.

“Fuck” she gasped as she let go. “Ok sink down now.”

I did as I was told and sank my hips towards her.

“Holy shit” she breathed as I felt her hot pussy for the first time. I pushed my cock as far as I could and held myself there. I tried to hold back a grin as I waved goodbye to my virginity.

“God you are big Jamie, give me a second then I want you to fuck me as hard as you can!”

“Ok” I simply said and awaited her signal. When it came I started to pump my hips.

Holy fuck this was easily one of the best feelings of my life. Masturbating is great but this is fucking amazing.

I looked down at the sexy body of Demi, whose mouth was wide open as she moaned in pleasure. I’m spurred on and fuck her with all my might.

“Fuck yes Jamie, fuck fuck fuck” she cried.

I grunt in effort as I slide in and out. Her legs are hooked around me as her hands hold her bouncing tits.

I wished this could last forever but there was no chance of that. I pushed on harder and moments later I sank into her as I came hard into the condom.

I groaned loudly as Demi screamed out as I filled the condom.

Guilt began to rush through me, followed by embarrassment. It must have only been a few minutes. I slowly pulled out of her and sank back onto the bed.

“Sorry” I murmured as I looked down at the condom that was hanging low from my cock, the end overfilled with cum.

“Huh?” She panted.

“Sorry it was so quick.”

“Oh honey, we aren’t finished!” She sat up and kissed me deeply on the lips, her tongue exploring my mouth.

“We’ve got the first one of the way.”

She looked down at my cock and almost as expertly as she had put it on, she took off the condom without spilling anything. She tied it up and tossed it in a bin.

“Unless you don’t want to go again?” She cocked her eyebrow at me, with a wry smile.

“Definitely” I said lamely to which she giggled.

We kissed again for a while as she coaxed my cock back to full strength. She wrapped it again in another condom but this time I lay on my back and she got on top of me.

What an experience to watch this beauty riding me. She was no Virgin and knew how to ride a cock. I lasted a lot longer this time and after she rode me I fucked her on all fours before I came just as hard. This time Demi came too, it was only confirmed to me by her vocal shouting.

“Oh fuck I’m cumming” she cried which was what really sent me over the edge.

Again I sank back onto the bed but this time in a much happier mood and a grin on my face.

Demi was now laying on her back as I watched her breasts slowly rise and fall with her breathing.

“Not bad at all Jamie” she said.

“Glad I came to your party.”

“Me too!”

We sat for several more minutes before this time I removed the condom doing the same as Demi. We both stood up and got dressed.

She didn’t say anything as she kissed me again. This one was just as passionate and hungry as before but a little more tender.

“Let’s go back downstairs, that’s surely been about thirty minutes” She took my hand and led me back down to the basement.

When we get back down there’s only three people there. My sister, Leia and Tyler. My sister and Leia cozy on one sofa and Tyler on another chatting away with them. The chatting stoped as we entered their eyeline.

“Welcome back you two” Riley said with a grin. “I can see you two had fun!”

My cheeks burned red again as Demi replied “Where is everyone else?”

I caught eyes with Tyler who had a massive grin on his face and winked at me.

“They all left after the thirty minutes.” My sister replied.

“It’s only been thirty minutes though?” Demi stated a little shocked.

The three of them began to laugh as Leia now spoke up “it’s been over an hour!”

“No way” Demi replied.

“My man” Tyler burst out.

“Time flies when you are having fun” Riley said to Demi but winked at me.

Demi and I both blushed as she joined the girls on their sofa and I sat next to Tyler.

“You lucky bastard” he nudged me as soon as I sat down.

“What can I say” I smugly replied with a shrug.

“How did it go with Natalia?” I quickly asked, hopefully shifting the focus away from me.

“To be honest it was awesome until you came back” he laughed.

“What happened like?” I asked.

“Well she wasn’t too keen to begin with but with a little charm we made out and then she gave me a handjob with her tits out. Was pretty fantastic. Would have loved to fuck her though.” He grinned.

“Bet you would” I nudged him back.

“So what happened between you and Demi?”

 
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