Late Night Truth or Dare Ch. 01: Bobby

Author's Note: At its heart, this is a college harem story, but as it contains incest, it must be categorized accordingly.

Late Night Truth or Dare - Sarah covers the same tale from Sarah's point of view. I believe you can start with either one, but this was the first installment written.

This version has been revised from the original to correct mistakes and reformat for better reading online.

--------------------

Late Night Truth or Dare - Bobby

--------------------

I stumbled from the car, catching my foot on the curb and almost face-planting into the concrete sidewalk, only saving myself from severe facial injuries by grabbing the mailbox.

The wooden post creaked as it flexed under my weight. It was a good call to leave my car downtown, even if it would be another $40 that I did not have, to get it in the morning. It was still cheaper than a DUI.

The surge pricing of the Uber ride, combined with the last round of drinks -- which I bought for my friends -- was enough to place my checking account into single digits. The lowest it had been since I was flush with cash from my student loan deposit in January.

I would need to scrape by for the remainder of the summer, at least if I wanted to keep drinking.

Ultimately, it didn't matter that I was broke. I was living at home for the summer, and my parents would pay for everything essential until I returned to school in a month.

I hadn't wanted to spend the last summer of college at home with my parents and my dorky little sister, but at least I wouldn't be starving for the next thirty days. Nor would I have to get a job unless I wanted to, which I certainly didn't.

I was supposed to be living it up in an off-campus house with three of my friends -- trying to score with the underclassmen -- but our lease fell through at the last minute. The landlord said something about an arrest for disturbing the peace on John's background check.

John claimed it was from a protest he attended the summer after high school, but I was sure that wasn't the entire story.

No matter, the house was no longer ours, and I was stuck at home until I found a new place. Hopefully, one not patrolled by overzealous residential advisors.

Managing to steady myself, I made it to the front door without serious incident. I may have stepped in a flower bed, but the damage wasn't noticeable, and I would avoid my mother's wrath.

As I fumbled with my keys, unable to find the correct fit, the door swung open. I stood there dazed, having not expected anyone to be home.

My parents had taken a weekend trip to visit my aunt, who had recently birthed her first child, and my sister was supposed to be spending the night at a friend's house.

Standing before me was a bubbly blonde, bouncing on her toes as she gave me a once over. Her breasts bounced along with her beneath an oversized t-shirt, no bra holding them in place. The shirt was long enough to hide whatever bottoms, if any, that she wore.

She was short, maybe standing 5 feet, but her legs looked strong and athletic, with smooth skin displaying an even tan for as high as I could see. I didn't immediately recognize her, but she knew who I was.

"Oh, hi Bobby. We weren't expecting you home tonight," the mystery girl said, feigning disappointment, "I was hoping you were a stripper."

"A stripper?" I said, trying to comprehend what she had just said. "You know what? Never mind. I don't want to know."

"I hope you didn't drive," she said with an air of judgment.

"I took an Uber," I paused, struggling to remember which friend of my sister this was, "Ashley."

I hadn't seen her in at least three years, and boy had she grown up. Maybe not in height, but the last time I laid eyes on her, she had been flat-chested without any shape to her hips.

Now she looked like a woman, albeit a short one. Her face still had some baby fat, enhancing her cuteness and adding an air of innocence to her seductive curves.

"Well, don't just stand there. We're about to play a game. Come join us," Ashley said as she bounced towards the living room.

I watched as the hem of her shirt rose and fell, not high enough to fully answer my question but sufficient to confirm that it wasn't shorts.

Drunk and with nothing better to do, I followed the 18-year-old towards the sounds of several more teenage girls. I figured I would play a round or two of whatever board game they had dug up in the basement. I needed to wind down from the bar before I could sleep anyway. Plus, if the others looked anything like Ashley, why not enjoy the eye candy?

There were four more in the living room. My sister, Sarah, and three vaguely familiar faces, all her friends who, like Ashley, had matured since the last time I saw them.

Despite not being home much the previous three years, I had managed to make it to a few holidays. I watched Sarah go from a mousy underdeveloped soon-to-be high school sophomore to a confident young woman on her way to college.

To me, the other four ladies had seemingly ripened overnight, and it made me feel old.

They had gone from timid and pimple-faced to confident and sexually appealing.

They were freshmen when I was a senior, and I would never have considered dating any of them. Now, I could not help but admire their faces and bodies. Especially their bodies, which displayed ample amounts of skin.

Ashley plopped herself on the floor and crossed her legs, her t-shirt pulled apart, leaving a tantalizing gap. Unfortunately, the lighting was such that I could only see dark between her legs.

Bella sat next to her, wearing a white tank top that hugged her medium-sized breasts, with the dark of her areolas showing through the thin fabric. A strip of caramel-colored skin peeked out between her top and her satin booty shorts.

With her legs pulled up, a hint of camel toe showed where the shorts pulled tight against her crotch, and her ass cheeks hung out the bottom.

Bella's grandparents had immigrated from Mexico, but her features were predominately European, having descended from the Spanish Conquistadors.

Moving around the circle, I set my eyes on Candace, a thin black girl who was the star of the cross-country team. She sat on the floor with her back hunched, wearing a sports bra and high-cut running shorts. Her hair was natural, with a small afro reforming after having it cut short during the race season. She was shy, especially in comparison to Ashley's overly outgoing personality.

Dee finished out the friends on the floor. She was of Korean ancestry, but she bucked the stereotypes of being flat-chested by having a similar body to Ashley, with Ample breasts on an otherwise petite athletic frame.

My eyes lingered on her, not because of her looks but because she was wearing lingerie -- an odd choice for a friendly sleepover. A white babydoll cupped her breasts, loosely falling down her body. She was sitting on her knees with the fabric across her lap, making it hard to tell how short the outfit was. Or if she was wearing anything underneath.

I thought I could make out a hint of nipple centered on each breast. For me, the idea of sneaking an unseen peek was almost better than if it was decidedly noticeable.

The four girls stared back at me as I examined each of them. I tried not to stare, but my intoxication made it impossible to hide my interest. Each was beautiful in their own way, and they silently fought for my attention and pulled my gaze from one to another.

I decided I should sit before I made a fool of myself, or worse, my cock decided to pitch a tent for all to see. I was drunk enough, and they were sexy enough to make this possible. I relaxed next to my sister on the couch, the one girl who was not gawking at me like a prized cow up for auction at the county fair.

My sister was also a runner, and her body was similar to Candace's, if only in form, as their skin could not have been more different.

Sarah had the pasty skin of a ginger. So pale that she sported that thick white sunblock on her nose and cheeks during her cross country meets and often opted for long sleeves, even on the hottest days. She felt a bit more sweat was worth avoiding a sunburn and the accompanying pain. Her red hair completed the Irish palette she inherited from our dad.

I received brown hair and tannable skin from my mom's side, giving me a distinct advantage in summer activities and embarrassing prophylactic measures. The distribution of genetics did not make sense to me, but I never took more than high school biology, so who am I to judge.

Sarah was wearing an oversized t-shirt, and unlike Ashley, her small breasts were motionless under the material. Not that I would have paid any attention to them anyway, as I never thought of my sister as a sexual being. Not because she used to be a dork or was not good-looking, but because she was my sibling.

While she had turned into a beautiful young woman, my thoughts never turned sexual, and I continued to view her as my innocent younger sister. Thank God for the Westermarck effect. Otherwise, I might have been some kind of pervert.

Sinking into the cushions, I confidently spread my arms along the back of the sofa, looking toward Ashley.

"I thought you said we were playing a game. Where's the board?" I said, motioning towards the empty floor in the center of the circle.

"We're not playing a board game, silly. We're playing Truth or Dare," Ashley replied.

"Oh, fuck that. The last time I played was in 9th grade. It sucked then, and it'll suck now. Don't you have anything better to play?" I quipped back.

"Don't be a spoilsport. It probably only sucked because you were playing with a bunch of pussies. I promise we'll make it worth your time."

"I doubt that," I grumbled, but I didn't want to go to bed quite yet, "but, I guess, I'll play a few rounds."

The truth was I wanted to see where the game would go. I didn't have high hopes but being the only guy amongst four attractive girls gave me cause to dream, even if my sister's presence threatened to douse the flames.

Best case, I ended up with one in my bed, and at the very worst, I might learn some secrets I could hold against my sister.

"I'll go first," my sister spoke up. "If you get challenged, you get to go next. Deal?"

The rest of us responded in the affirmative as my sister looked from face to face, pretending to think deeply about who would be the best victim for her devious mind.

Despite the posturing, she quickly revealed why she wanted to go first.

"Bobby, truth or dare?"

I did not even stop to think about it. I was more comfortable doing something foolish on a dare than revealing a secret to my sister, much less the other four girls. I could always pass off the behavior as a result of being drunk and told to do it, but saying the wrong thing on a truth was potentially devastating. Those were the things that haunt you.

"Dare."

"Give us the key to Mom and Dad's liquor cabinet."

I realized it didn't matter if I had picked truth or dare; Sarah would've asked for the same information. If my parents found out I let my 18-year-old sister in on the secrets of the liquor cabinet, I would be toast.

Who knew what they would do.

They had made a big deal about letting me in on the secret when I returned home after turning 21, and even then, they seemed hesitant to trust me. I hoped this did not cause them to cut me off, even if it was for the last month of summer.

Choosing dare allowed me to maintain the secrecy of the hiding spot for now.

"I will get it for you tonight, but you have to promise not to abuse it, nor can you follow me to see where Mom and Dad hide it."

"Deal," my sister cheerfully agreed.

The mystery of the key was not as fancy as my parents made it out to be. They simply hid it beneath the wooden lip of the cabinet near the floor. It was a good hiding spot as it was hard to check under there, and once you knew where it was, you could swiftly retrieve it.

"Make sure to give it back before the morning," I said as I dangled the key from the tip of my middle finger.

"Deal. It's your turn," my sister responded as she plucked the key from my finger.

I stared from girl to girl, looking deep into their eyes, trying to see if any of them flinched. I wanted the one who was most afraid to be picked. They would always go for truth, and truth was an easy way to start the game in the right direction.

Even with my limited experience, I knew If you dared someone to do something beyond their limits, they'd bail on the game. This often caused it to collapse before it really started.

In contrast, if you asked a risqué truth, people would squirm in their seats, but ultimately they would choose to lie if you pushed them too far. I never saw anyone abandon because of a truth.

Usually, after a few salacious questions, people would loosen up and eventually steer away from truths and, in theory, into more adventurous dares.

Candace diverted her eyes and studied the floor when I tried to meet her eyes. She would be my victim. I then needed to figure out what to ask when she inevitably picked truth.

"Candace. Truth or dare?"

She hesitated in her response, starting to answer several times before stopping to reconsider her answer. She eventually settled on my predicted truth.

I figured I would start with a question that was not about her. This would not make it easy, as she would have to dish on one of her friends. This would, hopefully, lead to infighting, causing them to up the ante on each other in the subsequent rounds.

"Which of your friends is the biggest slut?"

"That's here tonight?" Candace clarified.

"Of course."

I could tell she already knew the answer, but she didn't want to offend anyone. Sheepishly, she raised her eyes to look at Dee, trying to convey an apology. Dee, for her part, didn't seem to fear the impending revelation.

"I don't think any of them's a slut."

"You have to pick one. Let's not say slut. Let's say sexually experienced. Is that better?"

"Well... in that case, I would have to say, Dee."

Dee smiled and shrugged her shoulders, owning her behavior and not holding it against Candace for outing her.

Across the circle, Ashley rolled her eyes as if she disagreed with Candace's answer. I could not tell if she felt personally snubbed or thought another girl took the cake. Either way, it seemed to get under Ashley's skin, hopefully leading to a retaliatory question.

Candace was next to pick the victim, hesitating only slightly before she focused on my sister.

"Truth or dare?"

"Dare," my Sarah quickly replied.

"Sarah, I dare you to make us all drinks."

The dare was straightforward and would grease the wheels, but I was already starting to lose patience with how long it would take to get anywhere fun.

Four sexy girls were sitting in front of me, and while I would have loved to make out, or more, with any of them, I was growing tired and did not think I would be able to stay awake long enough for anything to happen.

"None for me, thanks," I told my sister as she rose, "and make sure to spread it out from different bottles. It will be too obvious if you only use one."

After some awkward clinking and clanking and several trips between the kitchen and dining room, Sarah finally made it back into the living room with a tray full of drinks. There did not seem to be much method to their distribution.

Sarah handed one to each of us, with no regard for who liked what. Despite my attempt to decline, she shoved the penultimate glass at me before sitting on the sofa.

I reluctantly accepted the cup, which smelled like a Jack and Coke -- mostly Jack. I had no desire to increase my intoxication, so I set it to the side, hoping my abstinence would go unnoticed.

My sister and her friends were still well within the age of not caring what a drink tasted like, only worrying about how drunk it got you. In a few more years, they would look back on this time and realize how stupid they'd been, just like the rest of us had. Although, it takes some longer to develop a discerning palette, as some of my college friends continue to prove.

"My turn," my sister blurted out after a big sip. "Ashley, truth or dare?"

"Ummm... Truth."

"Who do you have a crush on?"

This was what I feared. The girls would get bogged down with crush this and most hated that, and the game would not develop into something more adventurous. It's how it usually played out.

Everyone got excited about Truth or Dare because there's a chance that people would do some crazy shit. In the end, however, everyone picked truth because they were afraid of being dared to do something they feared.

I never understood this. If you wanted to play in the first place, it was because you hoped it turned sexual, not because you needed to find out who has a crush on whom.

If you wanted it to turn physical, then you needed to take a risk and pick dare. Even if that happened, most people were afraid to suggest a dare that's more than kissing or some minor nudity.

Ashley lifted her head with a little smile and stared right at me. I was taken aback. Did she have a crush on me? If so, that would explain her excitement when I came home and her eagerness to invite me to join the game, but maybe I was reading too much into body language. I keenly awaited her answer.

"Oh, come on, Sarah, you know I have had a thing for Ken for years now," Ashley quickly answered and moved on. "Let's step things up a notch. Bobby, truth or dare?"

"Dare. These truths are getting boring."

It was true. I wasn't interested in anything these girls were hiding. Unless it was a secret desire to sneak into my bed later in the night when my sister was fast asleep.

"Well, in that case," Ashley paused, "I dare you to chug your drink, which you haven't touched, by the way."

Shit. Didn't she realize I was already drunk? They needed to catch up to me, not send me to my grave. I was marginally confident I wouldn't puke if I finished the drink, but I wasn't certain I would remain awake. I was on the verge of sleep, and another few shots could easily send me tumbling down the cliff leading to my bed.

"I am already pretty drunk--"

"Shut up and drink it, you wuss," Ashley interrupted my protest.

I always had a thing for bossy girls. Not that I wanted to marry them, but it was fun to have them tell me what to do for an evening or two, especially if things headed towards the bedroom.

Ashley seemed to be one of these girls. I was sure she demanded what she wanted between the sheets, and I would be happy to give her whatever she desired.

With that thought in my head, I reached for my glass. I tipped it toward Ashley before slowly raising it to my lips, trying to build suspense, before tossing it back in one gulp. I'm glad I did because it tasted like straight Jack, which is to say it tasted like burnt toast.

After I made a face to match my disgust, I turned my attention to Dee. She, as well as Bella, had been excluded from the game thus far, and I wanted to get them involved.

"Truth or Dare," I asked.

"Truth," Dee said instantly.

Another truth. What was with these girls? Didn't they want to have fun?

I only knew Dee was slutty, so I wasn't sure what would make her squirm. I wished I could personalize the question, but instead, I asked something generic that could potentially lead to fun later.

"Out of everyone in this room, who do you think is the best at oral sex?"

It was a question I honestly wanted the answer to. Hell, I would've loved to conduct an experiment right then and there. Line each girl up and let them suck my cock. Then we would know who gave the best blowjob.

It would take a miracle for us to get anywhere near that. At the rate the game was progressing, there was little hope of anything sexually charged emerging.