Having a younger sister had both advantages and disadvantages. Having a younger sibling to make fun of and coerce into doing my chores was convenient. In addition, it was a pleasant surprise to have someone other than my parents enthusiastically support me at hockey games by putting on my old jerseys. When we were kids, she was my favorite person. Where we grew up, youth hockey is pretty much all-consuming in the winter. While I worked my way through bantams and peewees, she happily accompanied me from hotel to hotel and town to town.
It kind of came naturally to me. She also had interests of her own, but I only went to her gymnastics meets or dance recitals once or twice a year because my mom forced me to. My glorious pursuit of one day playing in the NHL was more important to me than her activities. At least until around the age of 16, when it became clear that playing varsity for the high school team was probably as lofty a goal I could realistically achieve in the sport I love, I truly believed that was my future.
Even though Alyssa and her friends are two years older than I am, I’ve always thought of them as children. However, things move quickly. It wasn’t until my junior year that I realized how close she was to me. Her efforts to support me throughout the upper Midwest paid off when she made the freshman varsity cheer squad. She was now standing alongside the girls I aspired to date, my classmates. When I celebrated in front of the student section after scoring a goal, I would occasionally forget she was a member of the team and be taken aback by her beaming smile as she enthusiastically waved the pompoms.
That was the point at which I started to feel the disturbances of having a younger sibling. It was now uncomfortable to hear the cheerleaders being talked about in the locker room, especially when guys specifically mentioned that she was one of the hot ones. I’ve been a part of these discussions for a few years, and now the immature remarks about the girls took on a much different dynamic. She had always been a cute girl.
Obviously, as our friendship networks began to work together, it soon became more normal. In high school, I dated a few girls in her grade, and we ended up hanging out as peers through our shared friends. Jake, my best friend, became pretty close to Alyssa, and during my senior year, they started dating. At first, it bothered me, but eventually I got used to it. A small group of just the three of us and Alyssa’s friend Lucia formed. A few months later, Lucia and I started dating. Jake is still my closest friend, but he spends more time with my younger sister than with me.
Lucia and Alyssa are both seniors, and Jake and I are currently in our second year of college. The dorm room Jake and I share is where they practically live. Being around my young sister all the time wasn’t as uncomfortable as it might have been because there was always an unspoken rule about respecting boundaries. She and Jake took care not to make me feel uneasy with their PDA. As young lovers do, Lucia and I were having regular sex at this point, but I didn’t think much about Alyssa and Jake’s relationship.
They kissed, of course, but they never behaved strangely in my presence, and I tried not to do the same for them. Actually, the dynamic as a whole performed fairly well. Certainly, it used to. Lucia and Alyssa showed up on a Friday night with a bottle of cheap vodka, and the four of us got drunk and played card games in our room. We were forced to reconsider their usual departure time due to the alcohol, which was around midnight.
Alyssa asked if it would be okay if the girls stayed for the night when it became clear that they were in no shape to drive home around 10 p.m. She was able to persuade our parents to stay the night because I was there to watch over her, and I was too drunk to really care. Jake and I had a fair amount of binge drinking when we were twenty, but the 18-year-old girls, neither of whom weighed more than 115 pounds, had not yet developed much of a tolerance.
Everyone, especially the girls, became significantly more relaxed while we played Cards Against Humanity. Jake went to his desk drawer and pulled out a bag of weed after we were all healthy buzzed. Despite the fact that neither of the girls had ever smoked before, we both smoked occasionally. Since I had offered it to Lucia a few times before, which she casually declined, I assumed the girls wouldn’t be interested. They both wanted to indulge, surprising me. As the combination of alcohol and THC took hold of us, I rolled a spliff, and the four of us passed it around, coughing to keep from getting worse.
The girls must have been on a completely different level, no matter how twisted I felt. We lost focus on the game we were playing as we laughed incessantly over nothing in particular.
“Let’s try something new!” As she crawled over and gave me a kiss on the lips, Lucia said, giggling throughout.
“What advice do you have?” As I playful grabbed her cheeks and gave her a kiss back, I asked her.
“Decency or truth?”
Surprised by her suggestion, I turned toward Alyssa because I wasn’t sure if it would work given the unique relationships we all had. Jake and Lucia gave their approval before I could respond, and it was decided. The game started off fairly innocently, but the truth questions quickly escalated, as is typical. There wasn’t much discussion about who everyone had slept with because the two couples had essentially only dated one another. It appears that without discussing it, we had decided that asking our best friends, girlfriends, and boyfriends about previous relationships was a little excessive.
However, below that point, other things that would normally be prohibited became accessible. We set up the game so that the person could choose the truth or the dare without knowing who they were asking, and then we flipped cards to see who had to take the dare or answer the question. When Lucia boldly chose to be the first to choose to take a dare, she was unaware of what that dare would be, and that was the moment when everything escalated to clearly inappropriate levels.
Alyssa covered her mouth with her hand as she giggled wildly, flipping over the challenge she had down on paper.
The paper read, “I dare you to take off your shorts and play the game in your underwear for five minutes.”
Alyssa, “Oh, my God!” Surprised, Lucia quickly slipped out of her white cotton shorts and threw them at me as she sat back down next to me.
She was wearing purple pantyhose that looked like bikinis and had a pattern of lace around the edges. They did a good job covering her up, but I and I’m sure everyone else felt the shift in the energy in the room. I did not show any signs of being envious. I couldn’t blame Jake for looking down at the results when I saw him. Because I have faith in both him and Lucia, the fact that she was only partially exposed to everyone surprised me.
When it came time for me to speak, I asked, “How frequently do you masturbate?” “For thirty seconds, make the sounds you do when you touch yourself as realistically as possible,” I said as a challenge.
I was intoxicated and high enough to be able to shake off just how shady and taboo the game had suddenly become, but it was obvious that I had considered the possibility that Alyssa would be the recipient of my deeply sexual requests. Anyway, I thought I was. Naturally, by chance, my younger sister had to make the decision.
“Umm…truth!” She said it with a grin on her lips and a red face that was flushed.
She read the card aloud, paused for a moment or two, and then revealed the truth.
She laughed, adding, “Well, it depends on the day, I guess, but I usually play with myself every night before bed” and “Probably a couple of times a week with my special helper.” She let out a chuckle and left.
“Special aid?” Realizing how ridiculous it must sound to ask my younger sister this question, I asked.
“It is a tiny pink dildo. I refer to her as Lady V. Who’s next?” Her words were spoken twice as fast.
I told her in shock, “You’re up, horn ball,” that my sister had played with her pussy. I asked myself how long she has been doing this.
She recorded her dare and question in writing. This time, Jake was the one who was hit, but he bravely took the risk.
She read, “I dare you to demonstrate your skills of seduction, if you have any.”
As he crept toward Alyssa, Jake said, “Easy.” As his hand vanished behind her back, he gently sucked on her skin and pressed his face into her neck. Alyssa’s bra had been unclasped in a short time. His hand came to her front side and slid up her shirt and he removed the bra from her, throwing it capriciously back as he kept kissing her neck.
“You guys, that is so hot!” As she paid close attention to them, Lucia said.
I was hit on the shoulder by the bra. I managed it and got a close-up look at what my sister was wearing underneath for the first time. I read the tag out loud by accident because I couldn’t help but find it. 34C. Never thought of that.”
Alyssa gasped as Jake returned to his spot, appearing to be offended. I’ll let you know, same size as Lucia!”
Lucia’s firm breasts are my favorite. They are just the right size, and as I was looking at my sister’s chest, I could see the hardness of her nipples poking through her white t-shirt.
Hers are much larger. Sorry, sister. Nothing to be embarrassed about!
Jake said with a shit eating grin, “Proooove it.”
Lucia turned to look at me. Shall we?”
I just shrugged. She pulled her shirt over her head, unhooked her bra from the front, and tossed it. “Looks like you have to…” We all experienced our first nudity. Alyssa quickly slipped one arm out of her shirt at a time before throwing her shirt to the side. Although it was pretty obvious which had larger nipples, I honestly couldn’t tell you which were larger. A matching areola about an inch and a half in diameter surrounded Alyssa’s dark brown nipples, which protruded at least an inch. My cock had been on high alert for some time, but the thought of my baby sister’s tits in front of my face made it start throbbing, taken in by this awkward situation.
On the card, Lucia wrote her choices and stated that one was only for boys. When I was selected, all I could think was, “Fuck it.”
“Dare.”
“I dare you to demonstrate how to properly pleasure breasts with your mouth,” the challenge reads.
“Perfect!” Leaning over to my girlfriend, I took the left breast tip in my mouth and thumbed it hard at the smaller point before gently pinching the other one with my fingers. After about 20 seconds, I came to a stop, but Lucia stopped me and informed me that I was only halfway done before I could get back to my position.
“Alyssa can’t be left out!” She stated
I overheard Jake say, “Go for it, man.”
Up to her face, I looked at my sister’s tits. With the new twist, she seemed fine. I felt like my cock was going to burst.
I crawled over to Alyssa and helped her lay flat on her back on the carpet as I guided her there. I lowered myself to her hard nipple and nibbled seductively with one knee between her partially spread legs. Flicking her nipple between my fingers, I cupped her other breast with my left hand. I interpreted Alyssa’s audible sigh as evidence that my abilities are legitimate.
I took over the position. For a brief moment, Alyssa and I locked eyes. Was she as captivated by this forbidden game as I was? Alyssa was the lucky winner of Jake’s options, which he wrote down.
She said, “Dare,” and Jake remained silent for a moment before announcing that this round was open to invitations. Is anyone else interested?
“If so, why not?” My partner agreed.
“Stop it. I said, “I’m in.”
As Alyssa began her reading, Jake replied, “As will I.”
She began, “20 minutes in heaven.” After I turn off the lights, whoever accepts strips that only cover their bottoms gets on the futon and pretends to be strangers at a swinger party. Everything returns to normal when the lights are turned back on, and nothing has changed.
We all looked at each other with curiosity, looking for signs of fear, disgust, or other similar emotions. Jake turned off the light after everyone had settled their differences. The curtains that blocked out light made our room completely dark. As bodies awkwardly joined me as I laid on the futon, I took off my pants. As someone grimaced in pain climbed in, I knelt down to my crotch.
“Sorry!” “Oh my God!” As a hand gently touched my dick and balls through my underwear, I heard my sister’s voice. Despite the fact that it would not be difficult to identify who was who, I did not say anything else in an effort to maintain our appearance of anonymity.
I reached out and pulled this unknown girl up onto me, feeling her tits smash against my chest as I pulled her head to mine and our mouths met. Her hand was cupped over my sack. My hands held her cheeks, which were only partially covered by a small triangle above her crack, as I slept on my back and had an intimate relationship with her. I rocked against whoever it was as our mouths explored each other’s. I felt her legs wrap around mine.
I could hear the other two getting hot and heavy to my right as well. I reached out and felt another girl’s ass as she pulled her pants down her bum as I did so. I was able to get them off her completely after pulling them down to her knees as she wriggled. I slid my fingers down her crack and felt the soft, trimmed pubic hair as I reached my mystery girl’s wetness as I pulled the skimpy thong off to the side with my left hand. She bit my lip as my finger slipped slightly inside her pussy. I violently grabbed her and flipped her over so that I was on top of her. I felt her completely soaked gash beneath her mound of soft, downy pubic hair, which was spread out between her legs. I found that even more sexy because her pants were still on, but they didn’t stand in the way. I licked her slit up and down, stopping to nibble at her sensitive prominent hood, until my face found her sex. She gasped as I made contact with her tiny ass hole as I lifted her legs and spread them further apart. My tongue slid further down.
Oh, my God! She repeatedly exclaimed, “Oh my God.” I adjusted my posture after removing my boxer briefs. As my cock drove home in her open pussy, I slipped my thumb slowly into her sensitive hole and rubbed some of the lubrication from her soaked cunt against it. After a few minutes, I helped her get down on her knees and pounded her from behind by bending her over in front of me. The remaining two people in the bed were having fun, but they didn’t seem to be bothering Ike with this. At this time, I had no concern. All that mattered was that the mystery girl’s pussy covered my penis.
She was having an orgasm all over my dick, and as she did so, I felt a rush of warm fluid come out of her. As I removed my cock from her pussy, my thumb was now penetrating her tight rear end. I pushed inside, inch by inch, until she was taking my entire length in her ass. I applied more of her natural lube to her as I liked my dick against her rosebud.
Oh, my God! Dan, fuck my a**! Thanks, big brother!
I suppose that all pretenses were dropped. My girlfriend and best friend were now just sitting on the edge of the bed watching me destroy my little sister as I kept going at her. Even though Jake had never done this to Alyssa and I had never fucked Lucia in the ass, here we were, lost in the pleasure of this forbidden kink as the lights came on.
Jake and Lucia looked horrified at us. I did not halt. I was going to finish this crazy plan that they started. They both left the room at some point, and my sister screamed as I was getting close to the end before clogging her virgin ass and falling over on top of her.
Under my sweaty body, I heard her whisper. What the hell just took place?”
After carefully rolling her onto her back and giving her a passionate kiss, I carefully removed my dick, which was still in her arse.
I said, “Not exactly sure.” Those two probably didn’t think we would go that far.
“But why did they leave?”
“Well, Jake realized that he couldn’t compete with that, and there’s no way I could take Lucia seriously after taking your lovely sex, Alyssa. You have the most amazing sister.