Late Night Truth or Dare – Sarah

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Author’s Note: This tells the same tale as Late Night Truth or Dare but from the perspective of Bobby’s sister Sarah. This story fills in much of the context missing from Bobby’s perspective, but in turn, misses much of the action in Bobby’s room. These companion pieces can be read in either order, and the other is not required to enjoy this one. If you feel something is missing or simply desire the complete story, please check out Late Night Truth or Dare.

The summer hadn’t gone as planned. After I graduated high school, I’d expected to spend my final months at home partying and being spoiled by my soon-to-be empty-nester parents. My brother, who graduated several years prior, had lived it up, having free rein to do as he pleased. My parents, who’d been strict until he graduated, had said he would be unsupervised at college, so he might as well get used to it before leaving. They didn’t extend me the same leniency. With me, their preexisting overprotective behavior continued. They claimed it was dangerous for a young girl to be so free. When I argued I’d been eighteen for several months, they countered that I should cherish my innocence while it lasted. It was easier for them to let my brother grow up. Maybe because he was a boy, or perhaps because I would always be the baby of the family.

There’d been no wild parties, only sleepovers with my friend’s parents asleep down the hall. I hadn’t been drunk or stoned all summer, with our hookup having gone on vacation with his folks. Worst of all, there’d been no boys to fool around with, meaning I couldn’t gain experience before college as desired. My group of friends was dorky, and not even their recently developed bodies could pull them from the dredges of the social hierarchy. Our social fates were sealed long before our senior year rolled around, with only a few brave nerds testing the waters with date requests. It took more than a nice set of boobs to make people forget years of public humiliation. Not that I even had the boobs.

Two of my friends, Ashley and Dee, had been able to break through and hook up with guys. This came from their willingness to do whatever the boys wanted, and never included party invites or non-sexual hangs. Dee, a big-breasted Korean American, had quickly gained a reputation around school as the girl guys asked out for a sure thing. She would put out for pretty much anyone who bought her dinner. Ashley, a bubbly blonde with a short and athletic build, was known for her head game. She was more discerning about who she let fuck her but was quick to suck a guy off in consolation. She told me she once blew the entire starting lineup of our school’s basketball team, a claim I can’t verify, but I don’t doubt.

I and my two other best friends, Bella and Candace, were still virgins. Bella, a Mexican American of mostly Spanish descent, had made it to third base with a few guys but hadn’t felt comfortable going all the way. Candice, a thin African American with small breasts, was the best runner at our school, but that didn’t get her laid. Her lingering celibacy wasn’t from a poverty of desire. My body was similar to Candace’s, except I was a pale as can be ginger. Candice and I met on the cross country team and hadn’t done more than some heavy petting with a few teammates, who were not the biggest catches on campus. This was supposed to be the summer it changed for us virgins. That, however, required being able to go to parties to meet boys. Hopefully, ones from different schools who didn’t know we were social kryptonite.

To cap it off, my brother Bobby had unexpectedly come home for the summer. I wasn’t too upset as we had always gotten along, but having a doting older brother back in the house made me feel like a child again. It was not always a bad thing. Having him around made me happy, and his arms always felt supportive when he gave me a bear hug, like he would do anything for me. He was also very good-looking, which my friends particularly relished. I surreptitiously ogled him as well, unable to convince myself that it was wholly platonic. Ashley had been openly crushing on him, and I am sure none of my other friends would pass up a night with him.

I couldn’t blame them. I had once accidentally walked in on Bobby getting out of the shower, and his cock was huge, even when flaccid. I could only imagine what it looked like hard. In fact, I’d given the better part of two weeks to exploring that idea. I learned to masturbate while thinking about my brother naked, though never dreaming of actually making a move on him. There was a taboo concerning incest for a reason, but I presumed it innocuous to fantasize about him. Even so, I kept it to myself, not even reporting to my four most loyal confidants.

My friends and I were going to Bella’s for a sleepover, the closest we came to partying, but I thought we were due for a change of plans when my brother said he was going out to the bars. I texted them to see if they’d agree.

Me: Hey girls! My parents are out of town, and my brother is going out drinking with some friends. I doubt he’ll make it home. Lefkoşa Escort Want to party here instead?

Bella: That’s cool with me. Does anyone have any weed?

Me: No, but I might be able to get into my parents’ liquor cabinet.

Dee: Sounds good.

Candice: I’m in.

Ashley: Me too. Too bad your brother won’t be there 😉

I’d lied to my friends, although I didn’t think they’d be upset. My brother almost always found his way home, usually completely shit-faced, making him prime for seduction. We just needed to figure out who’d be the lucky girl. I was sure Ashley would put up the biggest fight, given the length of her crush, but we were all horny, so I hoped we could find a way to share. It wouldn’t be the first time we’d messed around with each other. While a part of me wanted to jump my brother’s bones, I imagined the best scenario was watching him with one or more of my friends. I thought they’d accept that, and it would prevent me from becoming the sick girl who fucked her brother. I didn’t want that stigma, even if it wouldn’t accompany me to college.

I rummaged high and low for the key to my parents’ liquor chest. It wasn’t in any drawer, nor was it stored amongst any of the other keys. I’d marketed my house on the potential to get wasted, but now I couldn’t even offer that. All I had was a shelf full of DVDs and a drunk and hopefully horny brother, which I wanted to remain a secret for as long as I could manage.

When the girls arrived, bearing gifts of chips and cookies, no one appeared upset about the booze. It was par for the course the way the summer had gone. We settled in for a marathon of romantic comedies, starting with the classic of Mean Girls. We had all watched it more than twenty times, but we never grew tired of the plastics getting their comeuppance. I invariably enjoyed the talent show, having less to do with being attracted to girls dancing on stage in short skirts and more about wanting to be like them. I would never dare to put myself out there in such a sensual fashion, particularly in the face of a crowd. Although, I did occasionally have a taste for girls, so maybe it was a little about being attracted to them.

After much deliberation, Ashley pulled the next movie from the shelf, Cruel Intentions, a 90’s sexually charged romantic drama, which is profoundly problematic these days. It had an unusually pertinent plot point. Kathryn, played by Sarah Michelle Gellar, offers to sleep with her stepbrother if he wins a bet that he can seduce Reese Witherspoon’s character. A two-for-one deal if he succeeds.

“Would you sleep with Bobby if he was your stepbrother?” Dee stared me down.

“I… I have no idea, but I know Ashley still would.”

“Damn right, I would. He’s fucking fine.” Ashely mimicked sucking Bobby’s cock.

“You’re such a slut,” Candice interjected, “this movie is fucked up, by the way.”

“That’s why Ashley likes it so much,” Dee teased.

“What’re we watching next?” Bella piped up, clearly wanting to move on from the topic.

“Actually, I hopefully have a surprise for you. I kinda lied about my brother being gone for the night. I’m expecting him to come home, probably pretty drunk. Since it has been a bummer of a summer, I thought we could play Truth or Dare when he arrives. Maybe someone will get lucky. I know all of you, not just Ashley, would totally fuck him. What do you all think?”

“You would totally fuck Bobby if he was your stepbrother!” Dee hopped to her feet in excitement. “I hoped he’d come home.”

When Dee returned, she was wearing a white babydoll nighty, the outlines of her dark nipples visible through the lace cups that clung tightly to her breasts. About the size of grapefruits, her tits looked huge on her petite frame, her powerful hips and thighs finishing a well-proportioned figure.

“Where’d that come from?” Ashley seemed annoyed she hadn’t thought to bring something similar, just in case Bobby showed up.

Dee smiled and shrugged in response, triggering a rush from the other girls to make themselves as fuckable as possible. Ashley was the first to return, having donned a simple oversized t-shirt. It did little for her figure, but it fell tantalizingly high on her thighs, her ass cheeks threatening to display themselves with every move. Her breasts, now free from her bra, swayed hypnotically under the loose shirt. Bella wore a pair of satin booty shorts with a white tank top so thin her areolas were visible in the center of her perky handful-sized tits. Candace didn’t have anything appealing to change into, opting for a pair of baggy running shorts and a white sports bra. The outfit showed off her toned belly, which was always pleasing to look at and rest one’s head on. I didn’t attempt to look sexy for my brother, opting to put on my standard pajama pants and a t-shirt. Unlike Ashley, I didn’t have the breasts to sway seductively, whether I wore a bra or not.

“When will he be home?” Ashley asked, a little too eagerly.

“The bars closed 15 minutes ago, so any minute Kıbrıs Escort now.”

Everyone moved to the front window, waiting for the Uber to arrive, hoping to see my brother first, as if that laid claim to him for the night. I hung back, demonstrating a lack of excitement around what might occur when my brother arrived. I prayed he wasn’t excessively loaded. There’s a fine line separating pliable and passed out, abnormally narrow if there was any hope of me being in the room when it happened.

Ashley was the first to see the headlights advancing up the street. She bounded towards the front door, the hem of her shirt floating up to reveal a cute pair of panties underneath. I had half expected her to be completely nude under the shirt. I guess she felt flashing her cooch at my brother might come off as desperate. The rest of us watched through the window as he stumbled towards the house. He was drunk, but was he coherent enough to play Truth or Dare? We left Ashley to persuade him to play, the rest of us retreating to the living room, prepared to act like we weren’t awaiting him.

“Oh, hi Bobby. We weren’t expecting you home tonight.” We heard Ashley after opening the front door. Her acting was obvious, to those of us in the know.

I sat on the sofa, foreseeing my brother taking the unoccupied seat beside me. The rest of the girls formed a semi-circle in front of me. We’d previously removed the coffee table to sprawl on the carpet while watching the movies. We looked prim, sitting with our legs crossed, backs straight, and our hands in our laps. Entirely proper, save the revealing attire of my conspirators.

“Well, don’t just stand there. Come join us. We’re about to play a game.” We heard Ashley say before she came bouncing towards us, giving my brother a good view as he staggered behind her.

We girls traded glances as we sought to play it cool, not wanting to give away the forthcoming seduction. We should’ve planned it better, not leaving it to the individuals to operate independently. If we worked as a team then we’d surely get what we wanted, but if we fought against each other, we might turn him off, possibly sending him to bed before anyone was satisfied.

Bobby stood, swaying ever so slightly, taking in the sights, his eyes shooting from one girl to the next. He was working at being polite and not gawking, albeit unsuccessfully. He was unable to resist Dee in her babydoll and Bella in her sheer tank top, his eyes lingering on their breasts long enough for all to notice. I saw his eyes dart to Bella’s crotch after noticing the visible camel toe from her shorts pulled tight against her cunny, a lack of underwear allowing the fabric to slip between her lips.

He paid little attention to Candace. She was abruptly shy, hunching her back and glancing away from my brother when his eyes met hers. I hoped Bobby’s disinterest was due to this avoidance and not because of her body. We shared many features, only a difference in hair and skin color making us unique.

“I thought you said we were playing a game. Where’s the board?” Bobby replied as he relaxed next to me.

Ashley hadn’t explained what we were playing, perhaps thinking Truth or Dare would be too presumptuous to mention at the front door. I zoned out the rest of the exchange, my brother and Ashley bickering about whether or not Truth or Dare was an entertaining game. I wasn’t sure where Ashley had played Truth or Dare. At least that had materialized into anything more than gossip and weak ass dares. It didn’t matter though, as tonight had the potential to be wild. All the girls involved were willing to go as far as my brother wanted. He just didn’t know that yet.

“I’ll go first,” I spoke up. “If you get challenged, you get to go next. Deal?”

I dared my brother to open my parents’ liquor cabinet, which I knew was key to the rest of the night being fun. As sexually outgoing as Ashley and Dee were, the rest of us were relatively shy. We needed some liquid courage to get us over the hump. I wasn’t sure even Ashley and Dee would be up to the task while sober. Both of them had only been with high school boys, and my brother was about to be a college senior.

The game got off to a slow start, with most of my friends taking truths, still too sober to get into the dares. My brother, for his part, was trying to push the game in a sexual direction, asking Candice which of us was the biggest slut. She outed Dee with little surprise to anyone besides Ashley. I got dared to mix us all drinks, which I did with glee, making sure to add more than enough liquor to each glass. Ashley then proceeded to make a blunder by challenging my brother to chug his drink. He was already drunk enough, and I was afraid this would put him over the edge.

My brother, still hanging in, asked Dee who sucked the best dick and who ate the best pussy. She didn’t hesitate in saying Ashley gave the best blow jobs, but really who could tell. The only accurate way would be for us all to go down on my brother and let him be the judge. I got nervous Girne Escort as I was the only one who’d eaten out Dee, and sure enough, she outed me for that. My face turned red at the information being communicated to my brother. I wasn’t sure how he’d take it. It’d been earlier in the summer during a sleepover. We’d started watching porn, and well, one thing led to another.

We’d talked about how boys sucked at eating pussy which led to experimenting on each other, seeing if we could do any better. After a few minutes, we all forgot why we were doing it and eased into having fun. The next day everyone was awkward and shy, but we’d quickly moved past it. I am sure it was in the back of everyone’s minds as we worked to seduce my brother. Sadly, I’d made it further with my friends than I had with any boy I’d been with.

The girls started to bicker, accusing each other of dressing provocatively to seduce my brother, which I knew would turn him off. He never liked arguments, especially when he wasn’t allowed to have a say. I began to worry we’d lost him as his focus drifted. It could’ve been the extra alcohol, or it could’ve been the game stalling over an internal debate about clothing choices. The topic was finally changed, but the damage was done. After a few rapid-fire rounds of truth revealed that none of us were on birth control, my brother stood and called it a night, declaring he’d drank too much. I believe he’d have stayed if the girls had been more prepared to pick dare, but the lackluster beginning to the game hadn’t supplied him with the hope of any real fun.

“Sleep tight, Bobby. I hope you dream of us, especially me,” Ashley called out as my brother walked away, “although it still won’t be as good as if you stay.”

We all giggled, knowing Ashley was serious. It was too late; my brother had given up on anything intimate happening. In retrospect, we should’ve known he would grow tired and prepared a more direct and immediate approach. However, still being sober, none of us would’ve been up to the task, even if we’d planned it better.

“We might as well get shit-faced now.” Dee chugged the rest of her drink, motioning for the rest of us to follow.

I soon had another round poured and served to my friends. They were just as strong as the previous, quickly propelling our inexperienced bodies towards debauchery.

“Shall we continue the game? I could use some fun, even if your brother is a lightweight,” Dee suggested, glancing in my direction.

“Sure, who’s turn is it?” Candace asked.

“Mine,” Bella announced, “Ashley, truth or dare?”

I had a feeling things would ramp up quickly. The extra couple of shots had loosened us up, putting us where we should’ve been when Bobby got home. It’d been a good plan, but it failed without access to the liquor.

“Dare. Let’s get this game going,” Ashley announced.

“Take off your shirt for the rest of the game.”

Ashley didn’t hesitate, standing and pulling the baggy shirt over her head. My eyes focused on her bright red panties before shifting to her gorgeous breasts as they slipped from under the fabric.

“What size are those anyway?” Candace asked, a hint of jealousy in her voice.

“Thirty-four double D.”

“Well, you have me beat. I’m only a thirty-two D,” Dee added.

“How appropriate,” Bella laughed at the unintended joke. “I’m a thirty C if anyone cares.”

“We all care, Bella. Anyway, it’s better than my thirty-two A’s. These are sad.” I cupped my tiny breasts through my shirt, trying to give them a shake.

Candace, who I always assumed to be the same size as me because we’d shared bras, turned out to be a thirty B. She explained it was a sister size, but I didn’t fully understand. Nevertheless, we were both small compared to the other girls, making up for it with our toned tummies and long legs.

“Alright, Candace, truth or dare?” Ashley asked.

“Before she answers. We all know pretty much everything about each other, so why don’t we just skip the truths?” Dee suggested.

She had a good point. There wasn’t much to learn about each other. There might be some sordid details here or there, but those would come out eventually. We all wanted the night to turn into our early summer sleepover. We just didn’t have the guts to say it aloud. Asking only dares, especially if we kept it sexual, would get us all naked with a faceful of snatch in no time. We all agreed to stick to dares, although we required another round of drinks first.

“Okay then, Candace, pick one of us and suck on her breasts for a minute.”

Ashley would’ve been the obvious choice as she was already topless and had the best jugs of the five. Candace, however, surprised us all and picked me.

“Also, if you have to remove clothing as part of a dare, then you must keep it off until we’re finished,” Ashley added.

I sunk into the couch, leaning back as Candace yanked my shirt over my head. She hesitated for a moment before leaning forward and taking a nipple into her mouth. She was gentle at first, but as the seconds ticked by, she increased the pressure and even started to nibble with her teeth. I wanted her to slide a hand down my pajamas, but that wasn’t part of the dare. I had to settle for the nipple play. When the time was up, she leaned back and gave me a wink, leaving me with a glistening and erect nipple.

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