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 against whoever this person was as our mouths explored each other’s.
To my right I could hear the other two getting hot and heavy, too. I reached a hand out to them and felt another girl’s ass, tugging her panties down her bum. She wriggled and I managed to pull them down to her knees then completely off. With my left hand, I pulled the skimpy thong of my girl away and to the side, allowing free access to her ass and as I slid my fingers down her crack I felt soft trimmed pubic hair as I reached her wetness. My finger slid inside her pussy partway as she bit my lip. I grabbed her aggressively and flipped her over so I was on top of her. Her legs were spread apart, and I felt her completely soaked gash below her mound of soft downy pubic hair. Her panties were still on, but provided no obstacle, and I found that even more sexy. My face found her sex, and I licked her slit up and down, stopping to nibble at her sensitive prominent hood. I lifted her legs up as I spread them further apart, and my tongue slid further down, and she gasped as I made contact with her little ass hole.
“Oh my God. Oh my God,” she exclaimed repeatedly. I took my boxer briefs off and positioned myself accordingly. I rubbed some of the lubrication from her soaked cunt against her ass hole and slipped my thumb slowly inside her sensitive hole as my cock drove home in her open pussy. After a couple of minutes, I guided her onto her knees, bending her over in front of me as I pounded from behind. The other two in the bed were playing around, but didn’t seem to be fucking Ike this. I didn’t care at the moment. My penis was enveloped by this mystery girl's pussy, and that was all that mattered.
I felt a gush of warm fluid escape as she had an orgasm around my dick. My thumb was now penetrating her tight rear end as I removed my cock from her pussy. I applied more of her natural lube to her ass as I liked my dick against her rosebud and pushed inside, inch by inch, until she was taking my entire length in her ass.
“Oh my God. Fuck my ass, Dan! Yeah, big brother!”
I guess all pretenses were out the door. I kept going at her, completely oblivious to the fact my girlfriend and best friend were now just sitting on the edge of the bed watching me destroy my little sister. I had never fucked Lucia in the ass, and I’m fairly certain Jake had never done this to Alyssa, but here we were, lost in the pleasure of this forbidden kink as the lights flipped on.
Jake and Lucia were looking at us in horror. I didn’t stop. They started this crazy plan, but I was going to finish it. At some point, they both walked out of the room, my sister screaming as I neared climax before cumming inside her virgin ass and collapsing on top of her.
I heard her whisper underneath my sweaty body. “What the fuck just happened?”
My dick was still in her ass, and I very carefully removed it, rolling her onto her back and kissing her deeply.
“Not exactly sure,” I replied. “I don’t think those two expected us to go that far.”
“Why did they leave, though?”
“Well, Jake realized he couldn’t compete with that, and there’s just no way I could take Lucia seriously after taking your sweet ass, Alyssa. You’re the best sister ever.”
