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Growing up with a younger sister came with its perks and its annoyances. It was convenient having a younger sibling to poke fun at and manipulate into doing chores for me. I also rather enjoyed having someone other than my parents enthusiastically cheering for me at hockey games, wearing old jerseys of mine to show her support. She was my biggest fan when we were kids. Youth hockey is pretty all-consuming during the winter where we grew up. She happily followed along from town to town, hotel to hotel, as I worked my way through peewees and bantams.

I kind of took it for granted. She had her own interests, too, but I showed up to maybe one or two gymnastics meets or dance recitals of hers a year, and only because my mom forced me to. In my mind, her activities were far less important than my glorious pursuit of one day playing in the NHL. I truly believed that was my future, at least until I was about sixteen, when it became clear playing varsity for the high school team was probably as lofty a goal I could realistically achieve in the sport I love.

Alyssa is two years younger than I am, but I always thought of her and her friends as kids. Things change quickly, though. The first time it occurred to me she wasn’t that much younger than I am was junior year. Her years of cheering me on across the upper Midwest paid off when she made the varsity cheer squad as a freshman. She now stood alongside my classmates, the girls I dreamed of dating. After scoring a goal, I’d sometimes forget she was part of the squad as I celebrated in front of the student section, getting caught off guard when I saw her beaming smile as she waved the pompoms energetically.

That was when I began to feel the annoyances of having a little sister. Hearing locker room chatter about the cheerleaders was now uncomfortable, especially when guys specifically mentioned her as being one of the hot ones. She had always been a cute girl, but I’ve been part of these discussions for a couple of years, and now the immature comments about the girls took on a much different dynamic.

Of course, it soon became more normal as our friend circles started to mesh. I dated a couple of girls in her grade in high school, and we ended up hanging out together as peers through our mutual friends. My best friend, Jake, became pretty close with Alyssa, and they eventually started dating my senior year. It bugged me at first, but eventually I grew accustomed to it. The three of us, along with Alyssa’s friend, Lucia became a tight little group. Lucia and I started dating a few months later. Even though Jake was and is still my best friend, he spends more time with my little sister than he does with me.

Jake and I are in our second year of college now, and Lucia and Alyssa are seniors. They both practically live in the dorm room Jake and I share. There was always an unspoken rule of respecting boundaries, and it wasn’t as uncomfortable as it could have been having my kid sister hanging around all the time. She and Jake were careful not to make me uncomfortable with PDA. Lucia and I were having regular sex at this point, as young lovers tend to, but I was able to somehow not give too much thought to Alyssa and Jake’s romantic life.

I saw them kiss, obviously, but they never got weird in my presence, and I tried not to make things weird for them either. The whole dynamic worked pretty well actually. At least it used to. A couple of weeks ago, Lucia and Alyssa showed up with a bottle of cheap vodka on a Friday night, and the four of us got drunk and played card games in our room. Usually they would leave around midnight, but the alcohol forced us to reconsider that idea.

When it became evident around 10 PM that the girls would be in no shape to drive home, Alyssa asked if it would be okay if they stayed for the night. I was too drunk to really care, and she had no problem convincing our parents to stay the night, since I was there to watch over her. At twenty years old, Jake and I had done our fair share of binge drinking, but the eighteen-year-old girls, neither weighing more than 115 pounds, hadn’t developed much of a tolerance yet.

As we played Cards Against Humanity, everyone loosened up quite a bit, especially the girls. After we were all healthily buzzed, Jake went to his desk drawer and pulled out a bag of weed. He and I smoked somewhat regularly, but neither of the girls had done it before. I assumed the girls wouldn’t be interested, as I had offered it to Lucia a couple of times before, which she casually turned down. To my surprise, they both wanted to indulge. I rolled a spliff, and the four of us passed it around, suppressing coughs as the mixture of alcohol and THC grabbed ahold of us.

As twisted as I felt, the girls must have been on another level entirely. We laughed and laughed about nothing in particular, losing concentration on the game we were playing.

“Let’s play a different game!” Lucia said as she crawled over and kissed me on the lips, giggling the whole way.

“What do you suggest?” I asked her as I playfully grabbed her cheeks and returned her kiss with one of my own.

“Truth or dare?”

I turned towards Alyssa, surprised by her suggestion, not entirely sure if that was going to work, given the unique relationships the four of us shared. Before I could react, Jake and Lucia stated their approval, and it was decided. The game started innocently enough, but as tends to happen, the truth questions escalated rather quickly. Since both couples had pretty much only dated each other, there wasn’t a lot of talk about who everyone had slept with. Apparently, we collectively had decided without discussing that asking our best friends/ girlfriends/ boyfriends about past partners was a bit too much.

But below that line, other stuff that would probably be off-limits became fair game. We set it up so the person chose the truth and dare without knowing who they were asking, then flipped cards to find out who had to take the dare or answer the question. The moment everything escalated to clearly inappropriate was when Lucia boldly decided to be the first one to choose to take a dare, not knowing what that dare would be.

Alyssa covered her mouth with her hand as she laughed uncontrollably, flipping over the dare she had written down.

“I dare you to take off your shorts and play the game in your underwear for five minutes,” the piece of paper read.

“Oh my God, Alyssa!” Lucia was surprised, but wasted very little time sliding out of her white cotton shorts, tossing them at me as she sat back down beside me.

She was wearing purple bikini-style panties with a lace pattern around the edges. They covered her up decently, but I could feel the energy in the room shifting, as I’m sure everyone else did too. I wasn’t the jealous type or anything. I noticed Jake glance down to check out the results, and I couldn’t blame him. I trust him and Lucia, so it kind of turned me on that she was partially exposed to everyone.

My turn was next, and for my truth I asked, “How often do you masturbate?” and for my dare, “For thirty seconds, make the noises you do when you touch yourself as realistically as possible.”

It obviously crossed my mind there was a fair chance Alyssa would be the recipient of my deeply sexual requests, but I was drunk and high enough to shake off just how kinky and taboo the game had suddenly become. I thought I was, anyways. Of course, with my luck, it was my little sister who had to choose.

“Umm...truth!” she said with a flushed red face and tight-lipped grin.

She read the card out loud, hesitated for a second or two, then spilled the beans.

“Well, it depends on the day I guess, but I usually play with myself every night before bed,” she said with a giggle, then quietly added, “And probably a couple of times a week with my special helper.” She giggled and trailed off.

“Special helper?” I asked, realizing how fucked up I must sound asking my little sister this question.

“It’s a small pink dildo. I call her Lady V. Whooooo’s next?” Her words came out in double time.

“You’re up, horn ball,” I said to her, shocked to know my sister toyed her pussy. How long has she been doing this, I wondered to myself.

She wrote down her question and dare. Jake was the one on the receiving end this time, and bravely chose the dare.

“I dare you to show off your skills of seduction, if you have any,” she read.

“Easy,” Jake said as he crawled towards Alyssa. He nuzzled his face into her neck and gently sucked on her skin as his hand disappeared behind her back. After just a few seconds, Alyssa’s bra had been unclasped. His hand came to her front side and slid up her shirt and he pulled the bra off of her, tossing it aimlessly back as he continued kissing her neck.

“That is so hot, guys!” Lucia said as she watched them intently.

The bra landed on my shoulder. I pulled it off, taking a look at what my sister wears underneath up close for the first time. I couldn’t help but find the tag, and I read accidentally out loud. “34C. Never would have guessed.”

Jake had returned to his spot, and Alyssa gasped in somewhat pretend offense. “Same size as Lucia, I’ll have you know!”

I love Lucia’s firm breasts. They are the perfect size and now as I looked at my sister’s chest, the hardness of her nipples poked visibly through her white tee shirt.

“Hers are bigger. Sorry, sis. Nothing to be ashamed of!”

“Proooove it,” Jake said with a shit-eating grin.

Lucia looked up at me. “Should we?”

I shrugged. “Looks like you have to...”

She pulled her shirt over her head, unhooked her bra from the front and discarded it. We all got our first bit of nudity. Alyssa wasted little time, sliding out of her shirt one arm at a time before tossing her shirt aside. I honestly couldn’t tell you whose were larger, but it was pretty clear who has bigger nipples. Alyssa’s dark brown nipples stuck out at least an inch, and were surrounded by matching areola about an inch and a half in diameter. My cock had been on alert for quite a while, but this image of my baby sister’s tits before my face caused it to start throbbing, taken in by this kinky situation.

Lucia wrote her choices on the card, announcing this one was a boy-only option. When I was chosen, I just thought 'Fuck it.'

“Dare.”

“I dare you to demonstrate how to properly pleasure breasts with your mouth.”

“Perfect!” I leaned at my girlfriend and took the tip of her left breast in my mouth, tonguing her hard, slightly smaller point, gently pinching the other one with my fingers. I stopped after about twenty seconds but before I got back in my position, Lucia stopped me and said I was only halfway done. “And put some actual effort into it, babe.” I looked up and Alyssa just shrugged.

“Go for it, man,” I heard Jake say.

I crawled to Alyssa, and guided her back flat down on the carpet, so she lay completely on her back. With one knee between her partly spread legs I lowered myself to her rock-hard nipple and nibbled seductively at it. My left hand cupped her other breast, flicking her nipple between my fingers. Alyssa made an audible sigh, which I took to indicate my skills are legitimate.

I resumed my position. Jake wrote his options, and Alyssa was the lucky winner.

“Dare,” she said

Jake was silent for a second, then told us this was an open invite round. “Anyone else in?”

“Sure why not?” my girlfriend agreed.

“Fuck it. I’m in,” I said.

“As will I,” said Jake as Alyssa began reading.

“Twenty minutes in heaven,” she began. “After I turn the lights off, whoever accepts strips to just their bottom underwear, gets on the futon, and pretends to be complete strangers at a swinger party. Once the lights come back on, everything goes back to normal, and nothing ever happened.”

We all looked at each other questioningly, each of us looking for signs of fear, disgust, or things of those sorts. After no one made any arguments, Jake flipped off the light. Our room was pitch black due to the blackout curtains. I pulled my pants off and lay on the futon, bodies clumsily joining me. I took a knee right to my crotch as someone climbed in, grimacing in pain.

“Oh my God, sorry!” It was my sister’s voice I heard as a hand softly touched my balls and dick through my underwear. I didn’t say anything else, attempting to maintain our pretense of anonymity, even though it wouldn’t be difficult to know who is who.

Her hand cupped my sack and I reached out and pulled this mystery girl on top of me, feeling her tits mash against my chest as I pulled her head to mine and our mouths found each other’s. Lying on my back making out with her, my hands grabbed ahold of her ass cheeks, covered only by a small triangle above her crack. I felt her legs spread around mine and I rocked againstTo continue reading this story you must be a member. Join for FREE here.

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Alyssa 3 – Mom’s trap After Gary’s party I still saw Morgan at school every day, but now it was different. Now any time we crossed paths there was an obvious, almost irresistible draw to each other. I would always smile, or perhaps leer is a better word, and watch her pass by. I had to be very careful that Alyssa never saw, but I did watch her every time. I did get together with Morgan once or twice on the side when Alyssa had to go out of town for lacrosse games or some other event. We never...

3 years ago
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Alyssa Alyssa Oh my Alyssa

Chapter 1 I never asked for this! Christ, I was Philosophy major in undergrad. I only got my teaching certification because it occurred to me one night, what the fuck was I suppose to do with feeble philosophy degree. I had no idea they would put me in this position, I thought perhaps I would supervise over a study hall or teach me other bullshit class. I never imagined they would think I had the qualifications for this, and with a degree in slacking and bending the rules, what else would...

2 years ago
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SweEt fuCk to Sweety

I am going to tell you a real story which happens between me and my friend ?SWEETY?. I am working as a Manager at Mumbai. Now about me, I am a well mannered, handsome guy of good looking character. In my company there are lots of young talented girls are working. Among them the most ?Beautiful One? Is ?SWEETY?. She is 5.5? Tall, long black hair which falls below her buttock, small eyes, red lips, long nose, good neck, etc??.. She likes to wear sarees rather than any other modern dress. She tugs...

2 years ago
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Playground Sweeties

Playground Sweeties Oh how I loved those playground sweeties and I don’t mean their little daughters either. Young children have young mothers, generally. Being a single parent I took every opportunity to visit all of the parks in our town. For a small out of the way community we had four places for our children to play. The elementary school had a very nice solid wooden play gym, the high school had a nice field to run around on, and the main Community Park had a bunch of slides and...

1 year ago
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Chatting with Thomas Hassan

Chat Night Guest: Thomas Hassan On Saturday August 28, 1999 11AM PST Edited by Anne-Mal You can e-mail Thomas at: [email protected] In a change of pace, the guest is in the room first! (Thomas) Hi! *Looking around the room, waiting for the audience* (*Anne-Mal) Hello! (Thomas) Hmmm soemthing on mz kezboard here is fishz! (*Anne-Mal) For some reason everyone comes late, so don't worry! (Thomas) Arrgh! American keyboard... (*Anne-Mal) I doubt that members of the...

3 years ago
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The Seduction Of Cassidy

First story. I have always had a thing for my sister. It was a small crush that has been growing since my second year of high school. She is 19 and I am 18. This is the story of how that crush turned to love. I live in the Rock-chester home. A nice, 2-story, 3 bedroom house. I slept on the first floor, along with my sister, Cassidy, who was on the other side of the hallway that held our rooms. Our parents lived upstairs in their own room. My dad is 46 and my mom is 45. They still have a lot of...

Incest
2 years ago
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Alyssa 2 and MorganChapter 3

Alyssa I arrived at Alyssa’s house about half an hour later. At this point I really had no idea what to expect. She opened the door, dressed in just her bathrobe, threw her arms around me, and gave me the most passionate kiss I could ever remember. Then she finally pulled me into the house and closed the door behind us. After finishing a rather intense welcome kiss, Alyssa started apologizing for running out on me. “I’m so sorry, I never should have run off like that. I just couldn’t...

3 years ago
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All I Want For Christmas is My Mom8217s Sweet Ass

I never gave incest any thought, I mean sure I have had passing thoughts occasionally but I am not some kind of freak. Yes my mom is young, and I guess I always knew she was attractive from the way my friends acted around her. But until I saw her naked, I really never thought about fucking her. After that day I stopped thinking of her as my mom, and in my mind started calling her by her name Susan. If I had never found those old magazines in the attic, things might have been very different, and...

1 year ago
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Score Classics

ScoreClassics has a name that sets you up for something big. The “Classics” part lets you know you’re about to see some legendary shit, the kind of shit that has stood the test of time and is still talked about years or decades later. The “Score” part tells us we’re going to see somebody win big. It might be your favorite basketball team back in the ‘70s, but let’s be real, you’re reading this on ThePornDude. That big winning isn’t a sports thing, a video game tournament or a gambling problem;...

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2 years ago
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Reassignment

REASSIGNMENT By Ingrid Halb Reassignment Case file 2107-6306-G Subject: Candace (Ethan Kaine) Classification: FOUO/Sensitive Start Run: Yes it was possible for a tired 47-year old man to continue to be a productive member of society, but Ethan Kaine had chosen an increasingly obsolescent career path. His line of work was rapidly being automated with new AI software. But after 22 years of federal service Ethan was of the firm belief that the system worked and that the...

2 years ago
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Cassandra

I looked up and saw my 18 year old Cassandra looking at me. I didn't know what to say. I was mortified. She just stood there looking at the three of us. Felicia perked up and she said, "what does it look like we were doing? Having sex cassandra. And don't act like you don't want to. Daddy knows all about the three of us and you watching him and touching yourself..* She stood there for another moment or two and then walked out and went into her room. I jumped up and put my shorts on.I ran to her...

1 year ago
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Hubby Massage By Wife Along With Masseur

Hi ISS readers!!! Though i have been reading stories on this site for close to a decade, this is the first time trying to post my own experience. Bear with me and request to provide me with feedback to improve so that i can keep sharing my experiences in an interesting manner!!.. Little brief about me, For the purpose of reference – call me Sathish !!!.. I am 32 yrs old and work in an IT MNC domiciled in Chennai. I Love Sex and hardly i remember a day where i have spent with watching something...

1 year ago
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Alyssa

I had known Alyssa since we were probably nine or ten years old. She was one of the many girls I knew from the gym. She was also Kassidy’s best friend. They did everything together, school, camp, dating, sports, if you found one of them you probably found the other. Even though Kassidy and I had had a couple of amazing sexual encounters, she actually did have a boyfriend all this time. So a few times when they wanted to go out, and Alyssa didn’t have a date for the night, Kassidy called me to...

3 years ago
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For the Presidents Eyes Only Project Sweetpea

For the President's Eyes Only: Project Sweetpea By DEE DEE PERRI CHAPTER 1 The agent's eyes swept the crowded room once again with professional efficiency. To one untrained in his science, it would appear as a casual, almost bored, cursory examination of the restaurant, but a skilled observer would have noted the brief, almost imperceptible pause- the agent had detected something interesting. Now using the menu to partially obscure his actions, the man visually confirmed his...

1 year ago
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A sad depressed and bittersweet story

A sad, depressed and bittersweet story. Disclaimer: All though inspired by a real story, this is fiction. It is a story-taking place in a horrible society where money and money only makes the world going round. Disgusting events according to Danish standard are described and I would wish that we could save the world back from Denmark, so people did not need to go trough such a life, but we can only watch the unjust to happen. The solution has to come from the government on the Philippines....

4 years ago
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Chennai male masseur

This is preethi again. I am narrating a remarkable experience of mine with a masseur during last month. My Husband was selected as a winner in a lucky draw contest. The prize is a three days stay at a beach resort at . I was really excited to know this and we prepared for the stay and reached chennai. The first day we went for site seeing and rest of the day enjoyed in the resort. The next day we had a Spa Package. My husband was not interested in the spa treatment so he asked me to go ahead...

Incest
4 years ago
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Alyssa and her daughter my dream girls

I had fantasized for years about the two of us having a relationship but never expected anything to happen. I did not feel to be good enough being old at almost sixty , fat , disabled with back problems and just overall unattractive. It would have been like beauty and the beast. That is when fate decided to intercede. I went to a medical appointment which involved a wheelchair and medical transport there and back. I arrived at the doctors office being wheeled and the first one I saw was Alyssa...

1 year ago
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Alyssa Milano Animal Lover

Alyssa Milano came out of the bathroom, still a little wet from the shower she had just taken. She had not slung a towel around her magnificent nude body. She simply enjoyed walking around naked. She had tried to cool her off but when she was towelling down and rubbed over her large breasts and between her legs she became slightly aroused. Now she was fingering her cunt absentmindedly as she headed for her sleeping room. Suddenly her dog Digger appeared out of another room. He walked over to...

3 years ago
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A Gaggle of Lady Boys and the Deaf Masseur

Bangkok, Thailand, circa 1987: My first visit to a place I had only dreamed about for a long time. Ancient history, glittering temples, art, dance, water and an entire population of some of the most beautiful people on earth.I had experienced Thai Massage in Los Angeles, but was anxious to see what it was like in the its country of origin. Unfortunately, by that time, much of Thailand had been turned into a whore house by the American Troops having R&R during the Vietname mess. Don't...

1 year ago
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Private Classics

I bet everyone has their own Private Classics when they’re jacking off. You know the ones I’m talking about: those perfect pornos you may have found 5, 10, 20 years ago that still make you hard as a fucking rock every single time. It’s no wonder some of the long-running Internet porn sites have cashed in on the fad, offering up some of their vintage hits, oldies and goldies that put them on the map in the first place. I mean, shit, just because it’s old doesn’t mean you’re going to get bored of...

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1 year ago
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Classifieds

Every time he looked online, Drew found himself drawn to it. He wasn't sure why. Maybe because it suggested submission in such a strong way. Maybe because it emphasized the vulnerability he felt about his genitals. Not being big enough, masculine enough. Whatever it was, he couldn't deny he wanted it. But he couldn't order it online because he had no private place for it to be sent. He shared a room with someone and so a package like that was too risky. He'd driven to the only adult store...

1 year ago
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THE OVERPASS

My wife and I went to a party at some friends of ours house .Which was a treat as we have children so time alone is a cherished thing. We were having a blast drinking and laughing at all that was going on as everyone there was pretty lit.Well after a few hours of this we decided we'd better get home because it was almost an hour and a half drive. We had stopped on the way to the party at the package store and got a couple of bottles of wine on the way there. Just in case our friends didn't have...

Exhibitionism
2 years ago
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Assassin

Shadows seemed to change, seemed to move with each step. The moon, small and distant upon a velvet sky, shone little light upon the ground. The assassin needed no light to show the path, all that was needed was the candle lit windows that identified the manor. The assignment was simple, the target was easy, just getting in was the hard part. That was what she was told anyway. The hired killer reached the outermost perimeter gates. The iron bars were wide enough for the assassin to squeeze, or...

2 years ago
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Smelling Orthodox Wife From Hassan

Hi all Indian sex story readers, this is Madhan here, first of all, thanks a lot to all ISS readers for your many likes and valuable feedback for . I am a story writer with many stories published. I am writing this story after a break because there was nothing horny/wild in my life which was to be written. My dearest sex story readers, you can message me if you have come across or experienced wildest unique encounters, a real one. I will be happy to write the story in your stead and publish for...

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