Wrong Questions

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A pool party goes wrong for one guest.
3k words
4.14
10.3k
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Part 1 of the 2 part series

Updated 06/11/2023
Created 11/19/2022
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"Seriously again?" I asked as I looked at Lorraine, my girlfriend.

"What?" Lorraine responded.

Lorraine was the queen of selfies. She was aiming her stupid phone at herself every chance she got and taking a picture.

Lorraine's social media pages were filled with pictures of her, what she was doing, where she was, and what she was eating. It wasn't a surprise she wasn't able to hold a job.

Lorraine was adamant that one day she would be the perfect model, the next Instagram model to hit it big. I always laughed it off. She didn't have much of a following, but that didn't stop her.

Lorraine was, as some would say it, plain. I hated to admit it, but there were times when I caught myself wondering why I was with her.

I was no catch either. I wasn't pulling in all the women but compared to Lorraine. I was the better half.

Lorraine had blue eyes, which, if I have to say, was her best feature. She always plastered her face with makeup and dressed like she had it going on body-wise.

Even tonight, as we were heading for a Halloween party, she dressed like a succubus with wings and everything.

She wore a tube top that didn't have to worry about holding anything inside because Lorraine was flat as a board, as my friend Tyler always teased her.

Lorraine was envious of her little sister, that was sixteen and had giant tits already. It was hard for anyone not to look at them.

Lorraine stood just over five feet tall and was skinny as a beanpole. She even tried to do the only fans thing that was all the rage, but not one person subscribed, not one!

"Nice!" Jackson said as he opened the door to his house.

Everyone was here. I loved Jackson's parties. It was always a huge hit.

"Cyclops!" a guy said as I walked around.

I was a big movie guy and loved Cyclops from the Marvel comics, not the stupid movie black leather suit, but the original suit from the comics, blue and yellow.

"There is Mary, I am going to hang with them," Lorraine said.

"Sure, whatever," I shrugged.

I went outside to the large pool. It was filled with bubbles, and a bunch of women in skimpy bathing suits was inside it, laughing and playing.

"Stare harder, her bikini might just fall off," Tyler said as he bumped into me.

"Wow," I shook my head as I looked at him. "Again?"

Tyler was dressed like a doctor, or how he put it, a gynecologist. He kept saying these stupid lines to get women to take off their clothes. I swore that sometimes he was stuck in his college years and not a twenty-eight-year-old like me.

"Oh, like yours is original," Tyler shook his head. "What is that gel?"

Tyler looked at my brown hair and tried to get it out of place. "Leave it alone," I shook my head.

"Seriously, she wouldn't even notice you, even if you had a huge cow bell around your neck and was jumping up and down," Tyler shook his head.

He was, of course, talking about Jolene. Every guy in the building wanted a piece of her. She was drop-dead gorgeous with a body to match. Jolene had huge tits, a perfectly sculpted stomach, not even a pouch, long brown hair, and eyes that melted a man's soul.

"How does Jackson do it?" I asked.

Jackson was the man, not just the guy that worked out of a comic store, but the man. There he was in the pool with five women all over him.

He was no one to look at either. He didn't have rock-hard abs or the perfect hair. He was normal, average joe, but at every party, all these people would come, and he always ended up in the pool with the women.

"Who knows," Tyler said. "How does someone with an eight hour a day job at a comic book store afford a house like this?"

I nodded. That was true also. Jackson's house was huge, with a vast backyard and a pool.

"Come on, let's see what the others are doing," Tyler said.

By others, he meant Hank, Charles, and Grayson, the other members of our friends.

"Of course," I shook my head as we got to the kitchen.

They were drinking and staring at the girls on the dance floor.

"Just once," Grayson said, shaking his head.

"Rebecca wouldn't touch you even if you had a golden dick," Charles laughed.

"Yeah, well at least I have spoken two words to her," Grayson said. "You haven't even said a word to Cheryl," he laughed.

"I am waiting for the right time," Charles said.

"It's been seven years," I said as I took one of the beers from the ice chest. "The right time has come and gone."

"Yeah, like you have room to talk," Hank added. "Your girlfriend has the body of a teenage boy!"

"At least he has a girlfriend and gets laid, when was the last time you losers had sex?" Tyler said. "Having sex with a blow-up doll or your hand doesn't count."

None of them said a word.

"Pitiful," Jackson said as he came into the kitchen, his clothes drenched and dripping all over the place.

"Jackson, the man!" Hank and the others yelled.

"Derek, let me talk to you for a second," Jackson said as he looked at me.

I walked with him to a backroom where he got a towel and was drying his hair.

"Why do you hang with those losers?" Jackson asked.

"They are my friends," I shrugged.

"No, they are pathetic," Jackson shook his head.

"Yeah, compared to you," I smiled. "You've seen my girlfriend; I can't pull anything like what you can."

"Dude, you're breaking my heart," Jackson said. "I like you, you've always shown me respect, even before," he paused.

"Before what?" I asked.

Jackson sighed. "Okay, I have to show you something, but you can't tell a soul."

"Sure, I can keep a secret," I said as I finished my beer.

"They were tearing down a wall in the shop, when they found this," Jackson said.

"A piece of paper," I smiled.

"Yeah, but, I swear to you, it changed my life," Jackson said. "I read it a couple of times and bam, everything changed, I won the lottery, I can eat whatever I want and not gain a pound, it's fucking amazing, I say things people listen, don't know how but that piece of paper did it."

"Wow, a Halloween prank," I nodded as I looked at the old piece of paper. "What? I am supposed to read it and go out there and people will pretend to like me, then what?"

I gave the piece of paper back to him. "Nice try," I shook my head.

"Dude I just got my dick jerked off by April and Summer," Jackson said.

"They are lesbians," I shook my head.

"And those lesbians just jerked me off," Jackson smiled.

He held the paper in his hand, and I looked at it. "I swear if this is some prank," I said, shaking my head.

"I will leave you to it," Jackson said.

I looked at the paper; the ink on it was old and garbled. I tried to read whatever it was, "It's not even English," I shook my head.

I kept reading it over and over. Then it just got stuck in my head. I kept reading it in my head, out loud, and then it stopped. I just stopped.

"What the fuck was that?" I asked as if I had just woken up from a trance.

I shook it off and stood up. "Fucking idiot, falling for a stupid prank," I laughed as I went out of the room.

"Derek, right?" a guy said as I got out in the open. "Look you need to do something for me," he said as he held a wad of cash. "Keep this away from me, I can't have it on me," he said, shaking his head.

He walked away. "What the fuck was that about?" I asked as I counted the money. "Dude, this is three hundred dollars!" I said, but he was gone.

"Told you," Jackson said. "That's how it starts, I am telling you."

"This is definitely a prank," I nodded. "I am leaving."

I walked back to the living room. "Lorraine," I said as I approached my girlfriend.

"You are too good for me," Lorraine said with tears running down her face. "You should be seeing someone so much better than me," she said.

"What the fuck are you on?" I said, irritated.

"Go, I am setting you free," Lorraine said as she ran for the door.

"Seriously!" I yelled at her.

"Told you!" Jackson said.

"How the fuck do you keep appearing out of nowhere?" I yelled at him.

This whole night was getting stupid. I went out to see if I could find Lorraine and get the fuck out of here.

"You're not leaving, are you?" a woman's voice asked from the balcony above me.

"Yeah, this party is getting...." I said as I turned around.

It was Jolene. She was standing on the balcony in her bikini.

"I was just about to go back into the pool, want to join me?"

"Sure," I nodded like a stupid bobblehead doll.

I walked around the house and to the back. Jolene smiled and grabbed my hand.

"Shit," I said as I stopped at the pool. "I didn't bring my trunks."

"Who cares?" Jolene said as she dived into the pool.

"Okay then," I nodded.

I jumped into the pool. "Okay, bad idea," I said as the leather outfit stuck to my skin and started to shrink fast.

"Take it off," Jolene said.

"Yeah right," I smiled.

"You are wearing underwear, right?" Jolene asked.

"Yeah, boxers," I shrugged.

"Then take it off," Jolene said, inches away from me.

"Okay," I nodded.

I unzipped it, started peeling the tight leather off me, and slammed it down at the side of the pool.

"Better?" Jolene asked.

"Much," I replied.

Jolene was intoxicating to look at as she stood in the pool right next to me.

"You want to kiss me, don't you?" Jolene asked.

"You have no idea," I said, shaking my head.

"Do it," Jolene said as she swam closer to me. Our faces were less than an inch apart.

'This has to be a prank,' I thought the moment I lean in to kiss her. I will get laughed at and have to walk through this whole house in my boxers.

"Well?" Jolene said.

'Fuck it, I am going for it,' I thought.

I leaned in and kissed her. To my surprise, she kissed me back.

"See, you're still alive," Jolene said.

I grabbed her by the waist and pulled her closer to me. We kissed again, and this time it was much better than the last.

"What else have you been thinking about?" Jolene asked.

"Well?" I smiled.

'No fucking way,' I thought again. 'This is not happening, I must be dead or something, that's it, I am dead, and this is a dream before I wake up in hell. There is no way this is happening!'

I opened my eyes, and there she was Jolene Hackerbun was riding my cock on the bed in the upstairs bedroom.

"Still here," Jolene said as she bounced up and down on my cock.

I had my hands on her huge tits as she rode me hard and fast. Lorraine always got on top and lazy rode me back and forth, but Jolene rode my dick like she was at a rodeo.

'Holy fuck, she's going to tear my dick off,' I thought as I gripped her big bouncing tits.

"Is this what you imagined," Jolene said as she came down and looked me in the eyes as she rotated her hips.

"Not even close, this is a lot better," I nodded.

"Good, because it's going to get a lot better," Jolene said as she sat back up.

She rode me harder, and I had to grip the sheets. It felt as if she was pulling me up from the bed.

"I'm cumming," I said, thinking she would get off me and jerk me off.

"Then cum inside me," Jolene said as she stared down at me.

"I couldn't do that," I said, shaking my head.

"Why not?" Jolene said as she stopped bouncing and moved her hips back and forth. "You don't want to put a little you inside me?"

Jolene put a hand on her tight stomach with the nice ab muscles.

Every guy in the building would love to be in my position; impregnating Jolene was what most of the guys in the kitchen and the pool would only dream about, and here I was debating it.

"Cum inside me, now," Jolene whispered in my ear as she lowered her face to mine.

I held her by the waist and started bucking up inside of her. Then I held her down as I pushed up. 'Holy fuck,' I thought as I stopped cumming. 'I just came inside of Jolene Hackerbun!'

"I am going to get cleaned up, and then we can go again, or better yet we can go to your place and do it as many times as it takes to...." Jolene paused as she rubbed her stomach. "You know."

Jolene went into the bathroom, and I relaxed on the bed.

"Told you!" Jackson said as he was sitting on the edge of the bed.

"What the fuck!" I yelled. "How did you get in here?"

"Well, that's the problem," Jackson smiled as he stared at me. "You humans, never ask the right questions!"

Jackson shook his head.

"How did I get all of this?" he asked.

"Why did I pick you?" he asked

.

"How is all of this happening, why is this happening," he said as he stood up.

"But the most important question of all?" Jackson said as he stared at me.

"What the hell did I just read?" I said.

"Bingo!" Jackson jumped up and down. "Well Derek my dear boy, you just read a contract, making me the new owner of your precious soul."

"What?" I asked, sitting upright.

"Yes, you're dead," Jackson nodded. "Dead as a doornail, pushing up daises, met the grim reaper, all those good names for being D E A D.... Dead!"

Jackson laughed.

"No, I was in your room and then," I said.

"Then everything that you wanted started happening, you are late on your car payment by how much?" Jackson asked.

"Three hundred dollars," I shook my head.

"You've always wanted to break up with your girlfriend but never had the guts, always wanted her to do it," Jackson smiled. "Am I right?"

I nodded, curling my knees up to my chest. The cold realization was coming to me.

"And the cream of the crop," Jackson said.

"Jolene," I nodded.

"Humans, so easily manipulated," Jackson said, sitting on the bed next to me." Do you want to see what's really happening?"

I nodded.

Jackson put a hand on my shoulder.

They were putting my body in the back of an ambulance with everybody standing outside.

Lorraine was crying with her friends.

"One minute he was drinking then he just fell down," Tyler told a police officer.

"I'm really dead," I said, staring at my body.

"Yup, heart attack," Jackson smiled. "One of my favorites, so easily determined, that and brain aneurysms. Your human bodies are so fragile!"

We were back in the bedroom.

"What are you?" I asked.

"Another good question," Jackson leaned in towards me, his eyes went black as charcoal.

I jumped back.

"The devil!" I shouted.

"No!" Jackson shook his head. "Much lower on the totem pole, but yes a Demon of sorts, I like to feed on the pleasures of my victims."

"You can't do this to me!" I yelled at him.

"Oh yes we can," Jackson nodded. "We can't force you to do anything, but if you willingly do it," Jackson shrugged. "It's all fair."

"You forced me!" I yelled.

"No, I didn't," Jackson said, shaking a finger at me. "I showed you the piece of paper, then left, and you decided to read it. If you had simply walked out of the room, then I couldn't do anything, but now I am going to feed off of you for a very long time."

"Well, now that I know, I won't do it," I said, putting my feet down.

"So much spunk!" Jackson laughed.

"Well, I won't," I said, folding my arms.

"Well, I won't," Jackson said, mocking me as he folded his arms. He busted out laughing again.

"What's so funny?" I asked.

"Another question you forgot to ask," Jackson said, "Why did I tell you all of this?"

"No," I shook my head as it finally dawned on me.

"The other question is, how many times are you going to ask me?" Jackson said, standing up. "When I flick my fingers, you will forget all about what I have told you and go back to not knowing, and I will keep returning and letting you know, then letting you forget, and letting you know and letting you forget, over and over for all of eternity!"

Jackson started laughing again. I rushed toward him, and he flicked his fingers.

"All clean," Jolene said as she came out of the bathroom.

"Wow, you look great," I said.

Jolene wore jean shorts and a crop top that barely held her bulging tits in place.

"So, did you decide?" Jolene asked.

"Yes, definitely should do this at my place," I nodded.

I walked downstairs with my hand in Jolene's and was the envy of every guy in the building.

"Holy crap," I said as we approached Jolene's car.

"What?" Jolene asked.

"I have always wanted a car just like, the exact one, even the color," I said.

"Here," Jolene said as she tossed me the keys. "It's my dad's he gave it to me as a birthday present, I don't really like it, you can have it."

"Now you are pulling my leg," I said as I climbed inside.

"Not your leg I want to pull," Jolene winked at me and eyed my crotch as I pulled the seatbelt across.

"This night has been the best night of my life," I grinned as I pulled away.

The End

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