Getting Even or Getting Off

This is my entry for the 2020 April Fool's Day story contest. Please take a moment to rate this story when you are done to let me know what you think. Edited by Skye4Life.

It was past midnight, encroaching on Saturday morning, as I stood before the sink in the upstairs bathroom. My condom covered cock was in my fist, and I was beating my meat with an intensity that seemed rather forced given the circumstances.

"Come on Kyle. You got this buddy," I whispered to myself, squeezing my eyes shut tight as I tried thinking of anything other than the reason behind my awkward masturbation.

A rattle of the door handle startled me just before I heard Jessica's voice. "How's it going in there, Big Guy?" she called through the door.

"Jesus, Jess. You just set me back like five minutes," I cursed her. "You'll know when I'm done. You'll be able to smell the shame from down the hall." I muttered that last from under my breath.

"I just wanted to let you know that your sister's all ready for you, Stud," she said, not even trying to suppress her giggles.

"You don't want me to cum at all do you?" I asked to no one, because Jessica's footfalls were already fading back down the hall. "Like ever." I sighed as I got back to the task at hand, as it were.

I should probably back this up for you, and tell you why I'm jerking off into a condom, or why my sister's best friend Jessica was encouraging me, or even what my sister had to do with this whole fucked up situation. Well for that, I'll have to take you back to last year, and reluctantly share with you the single most humiliating experience of my life...

It was April 1^st, a day of innocent jokes and harmless pranks. It was also my sister Ashely's birthday. Ever since she discovered that her birthday was April Fool's Day, she had taken more pleasure in pulling pranks than she did in receiving gifts. Being two years younger, and behind the curve when it came to her devious mind, I inevitably became the butt of many of her pranks.

Ashely wasn't above the classics, like saran wrap on the toilet, or blue Kool-Aid powder in the shower head, but for April 1^st, she liked to pull out all the stops and try something special, and usually convoluted. The worst part of her convoluted ideas, they usually went off flawlessly, to my own personal discomfort.

Last years' experience was some of her best work yet, to my misfortune. I had woken up in a heightened state of paranoia, anticipating something from her. I took each step with great care, analyzing everything I saw as I moved throughout the house. I spent most of the day on edge, waiting for some sort of tripwire, or a bucket of hot tar to fall on me before I was beaten with a feather pillow. Every moment that I delayed the inevitable, the more paranoid I became.

The only time I felt truly safe was when I was mowing the lawn later that afternoon. Whether it was for my own safety, or hers, she never risked a prank on someone who was operating heavy machinery, or something that could be potentially dangerous. At least she had that boundary.

I had worked up quite the sweat, and after hydrating, I went to go clean the dust and itchy grass fragments from my skin. Still on edge, I took the time to make sure she hadn't put some sort of dye in the shower head, and then snagged a brand-new unopened bottle of shampoo from under the sink just to be safe.

Despite the freezing water, I found myself getting hard, and I decided to indulge myself. I was only human, and I was finding myself more aroused by the second. I was well into my stroking when I heard something from deep in the house. A moment later I heard it again, and I had to shut off the water to hear it more clearly.

"AHHHHH!" a blood curdling scream filled my ears, and every other thought left my mind as I hopped from the shower.

Rushing for the door, I grabbed a towel from the rack, wrapping it around myself as I rushed into the hall and towards the terrifying sounds coming from the living room. Halfway down the hall I lost my footing, and my feet slipped out from underneath me. In the tumult, I lost my towel as I slid down the hall feet first with my dick pointing up like a fleshy periscope.

As I skidded past the kitchen and into the living room, it dawned on me that I had once again let myself become another one of Ashley's punchlines. Trying to cover myself with my hands, I slid all the way into the living room to stop right on the rug between Ashley and all her friends as they pointed and laughed.

It's kind of hard to pick your dignity up off the floor when you're using both hands to try and cover the world's most painful erection. To their great amusement, I climbed to my feet, slipping as I tried to catch my footing on the tiled floor that was inexplicably covered in baby oil. Adding insult to injury, all her friends stood outside of my bedroom door for the next hour, taunting me, jeering me to jerk my cock. It turned out, that the refreshing Iced Tea I drank was filled with a few tablets of vitamin V...for Viagra.

That should explain sufficiently how much I dreaded April Fool's Day. This year, as the day came closer and closer, I felt that dread rising inside of me once again, anticipating something exceptionally cruel. Our parents were out of town, celebrating their 20^th anniversary, and everything seemed too quiet, too calm. From personal experience, it was the kind of calm that foreshadowed disaster for me. That is how I found myself at the mall a few days ago, stocking up on emergency provisions.

I know what you're thinking, She's your sister, not a natural disaster. Well, you'd be wrong. She's both. Despite her cute, wholesome exterior with those big doe eyes and long blonde hair with sweeping bangs that made her appear so innocent to our parents, she was a tornado on two long legs, intent on plowing through my life, leaving it ruined like the remnants of an upturned trailer park.

Where were we, again? Ah, that's right, I was at the mall two days ago, preparing for the coming April Fool's day...

I had just finished most of my shopping and stopped at the food court for a bite to eat before heading back home when I spotted someone coming over. She was beautiful; long brown hair that had a way of shining, a killer body, and these perfect pouty lips that always made me imagine kissing them whenever I saw them. She was one of the last people I wanted to see.

"What are you doing here?" Jessica asked, sounding surprised to see me as she slid into the seat across from me.

"Getting a new phone case," I lied.

"A phone case?" she mused, twirling a strand of hair between her fingers as she leaned over slightly to glance into the top of one of my bags. "I didn't know that Games Galore sold phone cases. It looks to me like you're planning on shutting yourself in for the big day." she said knowingly. "What's the plan? You gonna lock the door and play video games all day and eat junk food?" she asked.

"Of course not," I lied again.

"You know Ash will just smoke you out if she has to," she said, ignoring my protests.

"We'll see," I said. "What about you? What are you doing here? I thought you would be in class right now with the birthday girl herself."

"My dad thinks I need a job if I'm not taking enough classes to be considered a full-time student," she said, reaching forward to pluck a fry from my tray.

"You, working at the mall?" I scoffed. There was no way she would stoop so low. Her parents were loaded.

"Oh, God no," she laughed. "I'm just pretending to look for a job. That should be enough for daddy...at least until he forgets that he told me to get a job."

"It must be so hard being you," I mused, barely veiling my mild condescension.

"It is, but I manage," she mused, catching the slight tone in my voice but ignoring it. She knew she had it good. "Have you ever tried getting her back?" she asked curiously. "She's always screwing with you, have you never thought to give her a taste of her own medicine?"

"I don't think that's a good idea," I said. "You know Ash, she can get vindictive. The last time I pulled even a small prank on her, she made my life miserable for months before things died down again. In her eyes, only she is allowed to prank people. God help the hopeless soul who tries to get one over on her."

"Not even after what she did to you last year?" Jessica asked, disbelieving. "You're not really going to let that go, are you? You've gotta be planning something special for her this year." Jessica pried.

"No. I don't have anything planned. I replied, feeling my cheeks flush with embarrassment. Jessica had been one of the people there to witness my naked misadventure.

It's not like I'm ugly or deformed. I have nothing to be embarrassed about in the looks department. I work out and keep myself in great shape. The embarrassing part is that to all of my sister's gorgeous friends, I'm just a punchline, a walking joke that Ashley parades around for them when they want a good laugh.

"And if I was going to do something to Ashley, do you really think I would be telling her best friend?" I asked.

"Don't be like that," she persisted. "Do you think you're the only one that she does that shit to? Two years ago, we were shopping for clothes, and she grabbed all of my shit and bolted. I was left in the dressing room in only a pair of socks. I didn't even have my undies. I was stuck there until I finally shouted for someone to help me. This fifty-year-old guy came and found me, and he had to bring me some clothes, and I had to buy them just so I didn't have to walk home naked."

"That sounds kind of bad," I said, listening to her story.

"So, what do you say we team up this year?" she mused. "I bet you we could get her so good."

"What would we even do?" I asked, not believing that we could come up with anything that Ashely wouldn't see coming a mile away.

"Well, your parents are out of town until Monday, and I'm having this party on Friday night," she mused, her plan slowly beginning to unfold.

It took several hours, and a few more baskets of French fries before a plan began to take on a solid shape, and as great of a prank as it sounded, I wasn't feeling very comfortable with the part I would be playing.

"Don't be a pussy," Jessica scolded.

"But it's my sister!" I exclaimed.

"It's not like you're actually going to fuck her," she explained. "We're just going to make her think that you guys had sex. After you let her stew for a bit, you throw out the ole' April Fools, and it's done. No one's going to think that you actually had sex with her."

"Still, you're messed up in the head. You know that, right?" I asked. Her plan was perverse, way beyond anything a sane person might conceive.

"Hey, do you want to get her back, or not?" Jessica asked. "If you're fine with always being her doormat, that's all up to you. I can easily come up with my own prank."

"Fine," I conceded grudgingly. "But this better go off like you said it would."

"Yes!" she exclaimed, a huge smile sweeping over her face. "Don't worry Kyle, I know what I'm doing. Now, let's go over this again. We'll be at my party, and I'll make sure she gets drunk enough to where she blacks out. With your sister, it's easier than it sounds. After that, I'll get her to your place, and we'll set the stage for her morning after," she said, ticking off her mental bullet points. "After she wakes up and freaks out, she'll call me, and I'll fill in the blanks for her," she laughed.

"How do you know she'll call?" I asked. "You keep saying that it's the pacing, the rapid assault of events and information that'll keep her wound up in this prank, but you're putting a lot of faith in what you think she will do."

"I know Ash," Jessica said knowingly. "I've known her since before you could walk. Something like that happens and she'll call me," she assured me. "Now quit interrupting. Okay, so after that..."

Her plan was nearly as convoluted as one of Ashely's. Based on what I'd been hearing, I only gave it a potential success rate of fifty percent. Still, here I was, trying my damnedest to dump a load of my jizz into a condom, at Jessica's instruction, just to add to the realism when Ashely woke next to me in the morning. Finally grunting, I felt myself flooding the condom, leaving me feeling gooey and ashamed.

I carefully peeled off the condom, taking great care not to spill any, and pulled up my boxers. Shutting off the bathroom light, I headed back down the hall to my bedroom. Jessica had been insistent that we used my room. "If she wakes up with you in her bed, she's gonna think you crawled into bed with her," she had said. "We want her to think that she crawled into bed with you. Trust me."

Trust her? It was strange putting any trust in her at all. Traditionally, she and my sister had always been thick as thieves. Hell, Jessica had been present for each and every humiliation I had endured at my sister's hands. The only reason I continued with Jessica's bat shit crazy plan was that I knew my sister could have nothing to do with this. I had already analyzed it from every single angle, and I couldn't see any beneficial outcome for Ashley based on the events that we were fabricating.

Slowly easing open my bedroom door, I found Jessica arranging our clothing around on the floor, trying to create a strategic chaos. She insisted on the realism. It had to look like we had undressed ourselves in a hurry. Jessica paused for a moment before picking up a white thong from the floor and hooking it on one of the knobs on my dresser.

"Is she..." I began, shocked as my gaze moved from Jessica, to my sleeping sister snuggled up under my covers. "Is she naked under there?"

Ashely was lying on her stomach, and my thick grey comforter was thrown over her, leaving her upper back and shoulders conspicuously bare. Her blonde hair was tousled, already looking as if she'd experienced the wild night Jessica was simulating for her.

"Of course, she's naked," Jessica scoffed quietly. "Who has drunken sex and then goes rooting around to get dressed before they pass out?" Then noticing the spent condom in my hand, "Is that it?"

"Um...yeah," I said as she snatched it from my hand. I couldn't stop staring at my sister in my bed. She was naked underneath there, and I was going to have to crawl in there with her.

"How does that look?" she asked, stepping back.

Our clothes were scattered across the room in quite a believable fashion. Jessica had even taken the time to scatter some of the contents of my dresser top, making it appear as if one of Ashely's heels had landed there violently. The pièce de résistance was the used condom hanging over the edge of my waste bin, a small bit of semen pooling out onto a Green Day CD case on the floor.

"Looks real enough to me," I said nervously.

"Only one more piece left," she smiled at me mischievously. "Time to strip, Lover Boy!"

"Can't I just keep my boxers on?" I asked hopefully, already knowing what she would say.

"If she's naked, you've gotta be naked too. It's all about realism. Besides, we want her reeling from the moment she wakes up. The last thing you want is for her to see through her hangover and realize what day it is," she said. "So, pants off."

The way she smiled as she waited seemed like she was enjoying this part a little too much. Embarrassed, I got under the covers, keeping as far to the edge away from my sister as possible, and slipped off my boxers underneath the covers. As I tossed them out, Jessica had a cheeky, knowing grin, as if she knew that I had purposely cheated her out of the look that she wanted of me naked.

"Well, it looks like my job here is done," she said, looking around. "I'll lock the front door on my way out. Don't forget to call me after the initial fallout."

"I know my part," I assured her as I tried to adjust myself on my side of the bed. There wasn't very much room for the both of us and being naked only made things that much more awkward.

"Have a good night!" she smiled wickedly as she left, closing my bedroom door as she went.

My strained ears could hear the tell-tale groans from our house as Jessica made her way down the stairs and out the front door. As much as I tried to find sleep though, I couldn't. Even in the pitch darkness, I could still see Ashley lying naked next to me in my mind's eye. Try as I might to push that image from my head, I could feel her body heat radiating onto me beneath the covers, forcing the thought of her back to the forefront of my mind.

Biting back a frustrated sigh, I eased myself from bed and carefully made my way to my closet in the dark. Despite the knowledge that my sister was seriously down for the count, and hearing Jessica talking so confidently as Ashely lay passed out, I tried my damnedest to keep silent as I reached behind one of the boxes on the floor to pull out a hidden bottle of lemon flavored vodka. It was a parting gift from a friend's house party over a month ago. I quickly unscrewed the cap and took a long drink. Covering my mouth, I coughed and sputtered as it burned my throat. Steeling myself, I took another long drink and replaced the bottle before returning to my bed.

Using my hands in front of me as a guide, I felt my way to the edge of the bed, and slipped back under the covers just as I began to feel the alcohol pull me down into a nice warm place that made everything feel fuzzy inside. Adjusting the covers over me, I felt the warm skin of my sister against my side, and after hesitating for a moment, I turned away from her and lay on my stomach, as far from her as I could while still staying in the bed.

***Ashley***

Light pierced my eyelids like torturous blades, forcing me awake to realize my agony. My skull felt like it might split open at any moment. Desperate to fall back asleep and forget the pain, I pulled the covers over my head and shut out the light.

Just as I moved, so too did the mattress I was on. I held still, thinking for a moment that the room had begun to spin. When it shifted again, I realized that It was not a bed I was sleeping on, but someone's well-muscled back.

"Shit!" I groaned, realizing that I'd done it again. I had to quit waking up like this. Every time I would drink too much, I ended up in bed with someone, and I couldn't even remember it. The most embarrassing part, besides being that girl, was not being able to remember the names of the guys I would wake up next to. I'm going to kill you, Jessica, I thought.

"Hey," I said in a cracking morning voice. "Hey guy...man. It's time for you to go home now." Giving him a nudge, I raised my voice. "Listen dude, I know it was really awesome last night, but it's time for you to go now."

"Five more minutes," the slumbering mass of naked muscles mumbled.

"I'm not kidding...dude." I said, still not recalling his name. "You've gotta go before my brother wakes up. If he tells our parents that I had another guy over, they'll be pissed."

"I said five more minutes, Ash!" he mumbled louder.

As soon as he said my name, I froze. I knew that voice. My head was still ringing like church bells as I leaned closer, over his body to get a better look at his face. As soon as his profile came into view, I couldn't prevent the scream coming from my mouth as I leapt away from him.

As I flew backwards, my scream finally pulled Kyle from his sleep, and he sat bolt upright. I barely missed the edge of the bed and slipped off, making a loud thump as my bare bottom hit the floor. My brother's eyes met mine, and naked and panicking, I snatched the blanket from the bed and pulled it around my body. It might have been a mistake, Kyle was just as naked as I, and after a slight look of naked panic, he rolled off the other side of the bed, crouching there to hide himself.