Abby and Max - First Experiences

First Times

The first time my sister kissed me was basically an accident. Well, not an accident so much as just an unintended experience. Abigail, Abby for short, and I were at a college party for the first time. We made an agreement before we went that, while I visited her, nobody needed to know we were related. Why? Because nobody wants to fuck their best friends brother, and nobody wants to try pick up the girl who is hanging around with her six foot tall, security guard brother.

If I'm being honest, I'm not sure how exactly everything came to be that lead to Abby and I kissing for the first time. This is what I remember though. We got to the party late. It was a typical house party. The music was too loud with excessive bass and not a lot of anything else, and everyone was at least a bit buzzed. And by a bit, well, everyone was trashed. Really trashed!

That night was the first time I had ever looked at my sister and thought "Wow, she's stunning!" which isn't a thought people are supposed to have. She dressed up in a tight navy dress that ended just above her knees and it hugged her perfectly everywhere. Abby only stood 5 foot tall and some change, but that night her legs went on an age and only ended when they reached her perfect plump ass. She teamed her dress with white converse kicks and a backwards yankees cap. Her long blonde hair flowed down the sides of her cap like a waterfall. She was an absolute knockout.

I was far more reserved. A maroon checked button up and black jeans, black converse kicks and my long hair was slicked back and contained in a messy bun. Abby looked like an angel and i was just happy to be there. Abby introduced me to a couple girls as her friend from out of town and left to flirt with a couple guys. A brunette girl named Cassadee with deep blue serious 'fuck me' eyes and a curvy figure entertained me, telling me about the physics major she was taking.

While she talked, I watched Abby out of the corner of my eye. The way she floated from guy to guy, how she seemed to tease them and string them all along. It surprised me how much of a tease she was, it surprised me more that it turned me on. I couldn't figure out what had come over me but, for that night at least, my sister was the most drop dead gorgeous woman I'd ever seen. And boy, was she getting me excited.

"You're into her, aren't you?" Cassadee asked me, realising my attention was more on the way Abby moved her body next to the guy she was "dancing" with. Seemed more like dry humping to me, not that I was complaining.

"No, no. We're just good friends, seriously. I've just never seen her like this, it's fascinating." I laughed, hoping that it would cover my obvious attraction.

"Whatever you say, Max." She grinned back to me, her eyes locked on mine and begging for attention.

"What are you doing later?" I deflected.

"Depends..." She smiled coyly.

"On what?"

"What the best offer is!" I took that as my signal and pulled her out onto the dance floor and let our bodies move together, her tight ass shaking up against my crotch. I could feel my manhood throb to life against her, all seven inches begging to be set free, pushing against my jeans. Eventually, the crowded dance floor started to thin as people either passed out or slipped out to fuck like animals who didn't care who heard or walked in on them. That was when Abby and I got our first taste of... well, to put it bluntly, each other.

The game wasn't exactly truth or dare, and it wasn't exactly spin the bottle. It was some weird hybrid one drunk dude came up with that nobody challenged. So slowly one by one, as we stood around a kitchen island covered in drinks, we took turns taking shots, sharing our dirtiest secrets and kissing a random stranger decided by the person before. It was insane the shit that people were sharing, just so they could kiss some random girl or guy.

Ben, the party host, told a story of how during a threesome the girl he was with demanded that one guy on onto Ben's cock so she could slurp it off. He also shared, maybe a little too graphically, how the entire experience made him cum so hard he almost passed out and had been bisexual ever since. And one girl, Tay, had fucked two of her professors in her dorm room while her roommate watched. Then it got to Abby and I felt my stomach jump as she began to tell of how she had eaten her boyfriend's cum out of her best friends pussy while she got fucked by her best friend's boyfriend.

I was amazed, impressed, shocked and surprised. I had never thought my sweet, angelic sister could have done such a hot and shocking thing. The thought of her eating cum while being slammed hard from behind made my cock so hard I was surprised the whole group couldn't see it. I then watched her kiss Cassadee's friend Ashley. The way the two gorgeous blonde kissed, I could have touched my cock and it would exploded.

Finally, after Bianca's turn it was mine. I slammed back my shot and without even looking in Abby's direction, I retold my favourite story.

"So, my sister was out one night with her boyfriend, so my girl at the time came over and we started fucking like crazy. It's mental, she's being loud and wants to try every single position she can think of. And then, right as I'm about to nut all over her, she takes off across the house. I find her on her knees in my sister's bedroom in front this huge like floor to ceiling mirror and she starts begging." I look around the room, sly smile on my face but not making any eye contact with Abby. I could see her out of the corner of my eye though, jaw dropped. "And so I gave her exactly what she wanted, blasted her with so much cum. She was practically glazed. When I finally finished, she looked up at me and said 'Thanks big bro!' Absolutely crazy but the hottest fuck of my life."

The room nodded their approval and a few of the guys even clapped at my conquest. I finally gave Abby the satisfaction of looking over and she just glared at me. Not angry, just a glare of almost jealousy plastered across her face.

"Well Mr Max, after that excellent story, you need someone to kiss." Cassadee finally said breaking the silence in the room. "I'm thinking you should kiss our girl Abby, she hasn't had nearly enough fun tonight."

"Sure!" I said, not looking at Cass. I crossed the kitchen and leaned down to my pretty blonde sister, brushing her hair out of her face. She bit her lip, looking up at me with those incredible blue doe eyes but she never hesitated like I expected her to. I met halfway, with Abby up on her tippy toes and we kissed quickly. A little more than a peck but far less than the make-out sessions everyone else had participated in.

"Uh uh!" Cassadee said the second we pulled away from each other. "We need more than that!" Her words were quickly chorused by the rest of the group. And I had no problem with going back for more. Clearly Abby didn't either because the second I turned back to her, she wrapped her arms around my neck and pulled me down into a passionate and tongue heavy kiss. I lost myself in that moment with my sister, I let my hands find her ass and, with ease, I lifted her to my level. Her legs wrapped themselves tightly around my waist and as I placed her down on the kitchen counter, knocking drinks out of our way, my cock throbbed back to life against her.

We kissed for what felt like an eternity, our tongues meeting each other over and over and our hands exploring each others bodies while the rest watched on. I took what would likely be the only opportunity I would get to feel Abby's perky tits and plump ass over and over. When we finally pulled away, I could feel the shame building inside of me while the room cheered. It quickly dissipated when Abby pulled me immediately back in for a quick peck.

"Thanks, Maxi!" She grinned as she hoped down from the counter and rearranged her dress. Whatever happened during the rest of the party, I have no recollection of. All I know is that Cass and I danced and drank and somehow ended up back at Abby's apartment in the early hours of the morning. Abby, in the room right next door, also clearly had found a guy to bring home because as I sunk my thick cock deep inside Cassadee's ridiculously tight cunt, Abby moaned through the walls to be fucked harder and harder. Her moans spurred me on as I made Cass squirm and beg for her own release.

I clutched at her body, enjoying her curvy figure and surprisingly ample tits, while slamming my thickness in and out of her to a chorus of moans. I quickly brought Cassadee to orgasm and then brought her to a second while I listened to my sister beg for more through the walls. It didn't take me long until I found myself on the edge of my own release, an orgasm aching at my balls to be freed. As if by a sibling bond we had never experienced before, Abby started to beg and plead.

"Cum on my face! Make me your filthy toy!" She cried through the wall. "Glaze me!" It only made me fuck Cass faster.

"I'm gonna cum!" I moaned louder than I usually would as I pulled out of Cassadee's dripping pussy. "Fuck, I'm gonna cum!" Cassadee didn't even hesitate in obliging, dropping from Abby's spare bed and onto her knees on the floor. She pushed her tits together and looked up at me, opening her mouth wide.

"On my face, too!" She moaned softly while I rapidly stroked my manhood above her. I sunk my cock deep down her throat before pulling back and unloading several thick ropes of cum all over her face while Abby moaned her own pleasure through the wall. Covered in cum, Cassadee slurped every last drop off me as I collapsed back onto the bed, completely spent.

"Come on, big boy!" Cassadee said eventually, tugging at my hands. "You need to clean me up now!" I lead the cum glazed princess to the bathroom where, much to my surprise, Abby was doing the exact same. Her plump bare ass met us at the door, and she barely seemed to care as we stood at the bathroom counter next to her. I took every opportunity as Cassadee washed her face to admire my cum glazed sister in the mirror. Cum dripped from her chin down onto her small but impressively perky tits. Abby collected it and, without taking her eyes off me as we watched each other in the mirror, she licked it from her finger and swallowed it.

My cock lurched back to life, rising and meeting Cass's ass once again. Cassadee didn't even look up from the washcloth she wiped her face with. She just mumbled something of an 'Already?' I just laughed and teased her tits and kissed her neck, right in front of my naked sister. Abby quickly wiped her own face down and with a cheeky grin, she leaned over and gave me a quick kiss behind Cass's back.

"Goodnight, Maxi! Goodnight Cass." She smiled, biting her lip and turned to leave the room.

"Goodnight, Abby." I said, giving her ass a playful slap on her way out.

~

After a night of little sleep but another hot fuck, I woke in an empty bed and two text notifications on my phone. The first was from Cassadee and another from Abby. I opened the one from Cassadee first.

Sorry I had to leave so early, lecture this morning. Quantum theory, lucky me! :( Last night was fun, lets do it again! xx Cassie

I quickly shot back a reply, telling her anytime she wanted to have some fun I was more than ready. Those two fucks were the best I had experienced in years. It was easily the best night of the last 6 months. Being single and working nights as security at a 24 hour mall didn't exactly leave a whole lot of opportunity for fun like that. The most fun I normally had was with my right hand and a bottle of lotion. I flicked over to the text from my sister, curious what she had to send at 9:38 in the morning that she couldn't tell me later.

I'm lonely, come talk?

Those four simple words were followed by an unmistakable surprise. A selfie my sister had clearly just taken, sleepy eyes and messy bed hair, biting her lip and covered just barely above her breasts by a sheet. 'Sent 4 minutes ago' was all I needed to see to get me quickly out of bed.

I almost didn't even bother putting a shirt on, deciding at the last minute she was still my sister and I needed to remember that despite what happened just hours earlier. I threw on an old Nirvana shirt and adjusted my briefs before slipping out of my bedroom and into hers. She lay in bed, taking selfies, body just barely covered. Sun light trickled in through her partially opened curtains and lit up the room enough to make Abby look almost etherial.

She smiled and threw her phone down as soon as she noticed me, slapping the bed next to her and pulling the covers back slightly.

"Come on, get in! I do all my best talking and thinking in bed." I shook my head and smiled. That's clearly not the only thing you do best when you're in there, I thought to myself. I didn't dare to say anything but I couldn't get the memory of her tight, toned body naked and covered in cum in the bathroom out of my mind.

"What's up, sis?" I said, settling in next to her.

"You had a good time last night?" She grinned from ear to ear, clearly knowing the answer. It was a moment I took to just admire how pretty and well adjusted my sister was. She really was the best part of my life, even if she had been a major pain growing up. The fights I used to get in protecting her all seemed worth it as the perky journalism major lay there next to me.

"Best night in a long long time." I grinned back.

"Definitely sounded like it!" She said nudging me. "Twice even?"

"I don't know," I said shrugging, "I think the party was my favourite part!" We lay silently for what seemed like an eternity before Abby finally said something.

"I have to go to class soon, you gonna be alright until tonight?" She sat up, holding the sheet over her chest and exposing her back to me. Her blonde hair flowed down over her back and as I watched it, I couldn't help but let my eyes trace all the way down to the bright pink thong which barely covered her perfect ass.

"I have my camera," I shrugged again, "I'll probably go take some photos and hang around the village. I'll be fine."

"Good! Now give me your shirt, I wanna wear it today!" She dropped the sheet, exposing her perfect body to me and wrestled with my shirt. I didn't resist, my eyes firmly locked on my sister's perfect tits. The fabric came loose and soon it was over my head and off completely. Abby slipped it over her slight frame, the fabric hanging off her tight braless figure. Half a second later she was out of bed, exposing her perfect ass to me and creating the perfect outfit with my oversized shirt as the centrepiece. "You can stay there as long as you need, babe. There's some tissues in the night stand!" She winked before disappearing out the door.

I waited until I heard the front door slam shut before I found the tissues and got to work. I was edging closer to another hot orgasm when my phone buzzed and chirped. A text from Abby flashed on the screen. I didn't hesitate to open it.

Hope this helps, big brother. Love you xxx

The text was followed by a single photo of Abby, obviously from moments before I stepped into her room that morning. Her perky tits were exposed and she sucked on one of her fingers, looking straight into the camera. It spurred me on uncontrollably, thick ropes of cum firing from my almost exhausted cock, splashing all over my muscular stomach. I waited for my cock to stop twitching and pulsing before I climbed out of my sister's bed and into a steamy hot shower.

~

That formed somewhat of a routine. Every few days Cassadee would come around for a wild fuck and the next morning I'd end up in Abby's bed with her stealing my clothes and teasing me senselessly. She never crossed that line though, with all the teasing and playful nudes she sent, it never went further. She never touched my cock and apart from the occasional playful butt slap I never touched her either. My month long trip eventually ended up turning into us becoming full time roommates.

I picked up a new job working security at a nearby bank and even started taking the occasional photography class at the university. Abby became my muse every time there was a class project that required a human subject. I think she loved the attention, we'd play around with the camera for hours working on our personal projects too. I soon came to have a portfolio of only photos of my sister nude or nearly nude. And I made sure to make use of it every night I wasn't with Cass. In fact, it was that portfolio that lead to Abby and my next sexual encounter.

I hadn't seen Cassadee in about 4 days and my cock was absolutely begging for a release. So, with Abby working on her own class project, I decided I could spare a little time to finally get that release. I busted out her portfolio and lay back on my bed. I slowly flicked through the photos while stroking my eager cock. I was pumping nice and fast, edging closer to a quick release when I heard a soft knock at my bedroom door. I resisted the urge to finish as my sister walked in and tucked my cock back into my briefs and called her in as I looked for a shirt.

Abby said nothing, just pouted from the doorway. I gave up looking for a shirt the moment I saw what she was wearing. The smallest pair of short shorts I had ever seen hugged her waist and a loose crop top barely covered her body, her hair back in a ponytail. She looked stunning, even in casual wear.

"Do you think my tits are too small, Max?" She eventually said, crossing her arms tightly.

"What?" To say I was a little caught off guard would be an understatement. She crossed my bedroom and climbed onto the bed next to me. Without a second word, she climbed right into my lap, straddling me, and I knew she had to immediately feel my thick cock against her pussy. Abby wriggled around, either getting comfortable or getting my cock into just the right spot before sinking down into my lap fully. She pulled my hands onto her waist and pouted again.

"Do you think my tits are too small?" She reached to the bottom of her crop top and lifted it quickly over her head. I know that time she definitely had to feel my cock throb and pulse as the sight of her small perky tits filled my vision. They were all I could focus on and I had to fight the urge to squeeze and suck on each of her small but thick nipples.

"Abby, your body is perfect! What's wrong, little sis?" I squeezed her waist playfully, unintentionally tickling her. Her body squirmed as she giggled, her pussy teasing my cock back and forth without trying. I realised this would be the perfect way to keep edging until my sister either left or helped so I squeezed her again. This time she rocked back and forth harder, giggling more as my fingers explored her waist.

"Stop! Stop!" Abby said between fits of giggles. "Are you sure? You're not just saying that?" I stopped tickling her and watched the way she examined her breasts right before my eyes. She pushed them up, down, and then together. As she tight body presented the little cleavage she could supply, I took perfect advantage. I gripped her waist tightly and pulled her down onto my throbbing and aching cock and leaned in towards her perky mounds. I kissed her breasts repeatedly, surprised by how warm and soft Abby's skin was. My sister softly moaned, clearly enjoying the attention I was giving her.

I kissed my way over to one nipple and sucked the thick bud into my mouth, teasing her with my tongue and playfully biting. Abby's hands found the back of my head and held me close, not letting me escape from her tender tit. I reach one hand up to tweak and play with her other breast while squeezing her plump ass with the other.

"Oh, oh big brother, don't stop!" Abby moaned above me. I didn't plan on it as I began to move my body rhythmically under hers. I slowly began to grind my thick cock into my sisters barely covered snatch. She responded, slowly moving her hips with mine so my cock would meet her snatch and ride right up against her clit. Her moans grew louder as I continued to tease my way back and forth between her hard nipples, sucking, biting, and licking them eagerly.