Fifty Things

Many thanks to Jenna for first editing and improving this story, to author/editor ColetteJulie, whose stories are so hot they'll melt your eyeballs, for further editing and suggestions that inspired me to make it much shorter and better, and to author/editor Amela, who plays with readers' minds in her unusual stories, for additional fixes and inspiration to finally solve the problem of the protagonist's motivation.

The high school slut was looking at me.

She sat at the other end of the bar. I recognized her instantly though it had been more than twenty years since I last saw her. Damn, she looked good!

My hair was thinner and I had gained a few pounds. For Catherine, it seemed as if time had stood still. If anything, she looked hotter than when she was young.

I felt a stirring at my crotch and laughed at myself. She was turning me on the same way she did when I was a pimply teenager. I wondered if she recognized me. She was with a young man who wore tight clothes that showed off his muscles.

As I looked at her, I imagined myself at eighteen again, in my senior year, lusting after her. A couple of things she had said to me had given me the impression that she had been approachable. Why didn't we ever get together?

She was the most beautiful girl in school, as well as the most developed. And she was insatiable at a time when most girls were scared of sex.

She was notorious for offering herself to every boy who said something that made her laugh or did anything to please her. She didn't seem to discriminate by race or looks, but the rumor was she turned away bullies and conceited rich guys.

The girls hated her, but most of the guys treated her with respect. There were a few who tried to put her down and call her names, probably because she had rejected them. But every guy I knew who had been with her told me that she was awesome, and that they would drop everything whenever she summoned them.

Her voice startled me, and I snapped back to reality. She and her friend stood in front of me.

"Hi Ronnie. How are you?"

"Great, Catherine! And you?"

"I'm fine. This is my friend, Harold. I was telling him that we were friends in high school, but we never hooked up."

"Ummm...I don't know what to say."

I think I got red in the face because she laughed.

"Did anyone ever tell you that you look cute when you're embarrassed?" she asked. "Don't worry about Harold. He knows all about what I did in high school. Did you ever wonder why?"

"I hope you forgive me for being a clueless, sex-crazy teenager. I didn't even think about what was happening in your home. You always seemed so positive and happy. Now I realize it was probably an act to cover up some terrible mental or physical abuse. I can't pretend that I wasn't eager to have sex with you. I was just like the others. For some reason, I never did."

Catherine smiled.

"Yes, you never did," she said with a sigh. "What you just said about me -- I've heard it so many times when I've run into kids I knew in high school. But it's all wrong.

"I wasn't abused or raped or anything like that. My family was as American as apple pie, and my brother and sister were like all the other kids. My life changed in seventh grade. Sex education really turned me on. I started experimenting, and I couldn't get enough of it! I still can't."

I saw her eyes light up and decided to change the subject.

"Do you live here?"

"No, I'm staying at the hotel and leaving tomorrow. How about you?"

"Me too," I said. "I've been in town on business calls. It was an exhausting day, and I've got an early flight. It was so nice running into you. Let me buy you and Harold a drink before I leave."

"Thanks, but you don't have to."

I heard a change in her voice tone from the polite friendliness that she had been using. It sounded like every word was perfumed with lust, and her eyes were gleaming as she looked at me. I glanced at Harold and wondered if he noticed.

Hearing that voice and seeing how good she looked, I would've jumped at the chance to take her to bed, except it was too late. I'm happily married, and even though I was out of town at a hotel where nobody knew me, I would never cheat on my wife.

I'd fantasized about adultery when I had to travel on business. After a day packed with meetings, I'd sometimes end up at the hotel bar for a drink. I saw a lot of beautiful women, most of them probably hookers, and I imagined things, but I never approached anyone and politely turned away those who came on to me. It was safer to watch porn in my room.

"It's my pleasure," I said, waving over the bartender. "Would you please take an order from this couple and put it on my room?"

Catherine ordered a martini, Harold a beer.

"Put it on Room 3016," she told him.

"No, I insist," I said. "Put it on 5023."

"Thank you," she said to me and then turned and nodded in the direction of Harold. He nodded back.

We touched glasses when the drinks came and talked a few minutes more. She asked me a lot of questions about what I had been doing since graduation, and I answered politely, trying to concentrate on winding down the conversation and ignoring her seductive voice, lascivious gaze and body language that left no doubt about what she was trying to do. I finished my drink and wished her and Harold a good night.

A few minutes later, I was already undressing in my room when I heard a knock on the door. I put the chain on and opened it a crack. It was Catherine.

"Look what Harold found," she said, holding up my wallet.

"Oh my god," I said. "Thank you so much."

I reached out for her to hand it to me, but she had stepped back and waited for me to open the door. I was in my underwear, and I didn't want any misunderstandings, so I asked her to wait a minute. I quickly pulled on my pants and opened the door.

As I did so, someone big grabbed me and lifted me in the air, carrying me to one of the two queen-size beds before throwing me onto it on my back and holding me down. Then I couldn't see anything as I felt flesh push into my face.

Whatever was pushing at me slid down, and I could see what it was. It was Catherine's naked butt. My eyes were uncovered, but she was still sitting on my face. I felt her pubic hair against my lips and tickling my nose. I saw Harold standing next to the bed. It was so bizarre that I would have laughed at the scene if I had not been in the middle of it.

I heard Catherine's voice from above.

"I'm sorry about this, Ronnie. I was hoping you'd make a pass at me and we would come up to your room together, without Harold. But you are a faithful husband. I compliment you for that.

"You're wondering what's going on, and I owe you an explanation. I wish I could do it face to face, but you'll have to listen in this position. I hope you're not too uncomfortable.

"This goes all the way back to high school. Despite being obsessed with sex, my brain has room for other stuff. Only my counselor and the teachers who saw my IQ score knew this. They were always telling me that my wild behavior would ruin a great career. Choices have consequences. If I heard that once, I heard it a hundred times. I didn't listen to them, and I didn't go to college.

"Instead, I went to trade school and became a cosmetologist. I found out that there is more sex of every variety available in the beauty industry than probably in all the others combined. It starts during school and never stops.

"When I graduated, I went to work at one of the big chains. Because of some suggestions I made to improve things, the boss made me assistant manager, and when he was promoted, I took over. I made a few changes, and my store won the award for the most productivity that year.

"A vice president showed up one day and took me to lunch and pumped me for ideas. The following week, he called me and asked if I'd be willing to move to corporate headquarters as his assistant.

"Corporate headquarters was almost as wild as beauty school and the salon. I moved up fast. I suppose it helped that in addition to being good at work, I also slept with nearly every man and woman in the office. When they found out that I didn't ask for anything in return, they gave me more than I would have ever imagined.

"When the president received an offer from a competitor and left, the board, which I'd also gotten to know intimately, unanimously elected me to be the next CEO.

"I made so much money for the company that the stockholders kept voting me bigger and bigger bonuses. I bought a big house and entertained a lot. I had everything money could buy.

"It seemed like I was living the life of my dreams, but it gradually dawned on me that something was missing.

"At first, I didn't know what it was, but then I realized what was bothering me. Everybody on the Internet and TV were always talking about following their passion. They climbed mountains, they ran marathons, they tried to win Olympic medals in archery, they competed to post the most selfies of themselves with famous movie stars. To be truly fulfilled, you needed to pursue the impossible dream. It didn't even matter if you achieved your goal. The journey was what mattered.

"I had enough money for five lifetimes, but I didn't have a passion. Then I saw the 'Bucket List' movie. There was my quest. I immediately began working on my own bucket list.

"I had dreams that went back all the way to high school. I always thought of them as fantasies, but maybe I could achieve them. I knew that my money wasn't enough. I had to summon the true grit and determination that the people on TV were always talking about. I handed in my resignation, but the board offered me an obscene amount of money to stay on for one more year. I was offered even more the next year, but I left anyway to begin my odyssey.

"My bucket list wasn't that large. It turned out to be only fifty-three, so I call it 'Fifty Men to Do Before I Die.'

"You are one of them, Ronnie. I wanted you badly in high school, but you didn't care. All the things I did with some of your friends never felt humiliating or demeaning. I didn't care what anyone thought.

"But the guys who turned me down or never followed through when I approached them were the ones who hurt me. I wasn't good enough for them. They considered me beneath them, and that made me cry into my pillow many nights. I never showed it at school, because I didn't want them to see, and most of the time I was happy. But those boys who looked down on me - I could never get them out of my mind completely.

"Can you imagine how humiliating it was for me to know you wouldn't give up one night of homework for sex with me? Don't deny it, Ronnie. Actions speak louder than words. Your choices have consequences. The consequences are tonight.

"I started with an expensive detective agency, but I'm finding most of the men with the help of the guys I've already tracked down. Your friend, Jim, helped me find you after I fucked him. I know you'll help me find some more of them. I'm determined to do all fifty-three before I die. Life is unpredictable and I could be killed in an accident tomorrow, so my mission is urgent."

I blinked because the room started getting bright as Catherine continued talking.

"My friend Harold, who just turned on all the lights, will be doing a video of us for a remembrance. Harold's as talented as he is strong. He's a magician and his hands are so fast that he can remove a wallet no matter where you carry it.

"Don't worry about the video. My goal is to screw fifty-three men, not destroy their lives. Unless you tell her, your wife will never know. And even if you feel you have to share this, she'll understand that it wasn't cheating.

"I think you will probably want to get this over with as soon as possible, so the best thing you can do is follow my instructions. If you don't, it will just take longer to do the same thing. Lick my pussy if you heard me."

I was still trying to comprehend everything and didn't immediately respond. I felt her hands unzipping my fly and going into my boxers. They cupped my balls and began squeezing slowly.

"Can you hear me now?" she said. "If you can, lick my pussy."

Her hands squeezed tighter. I quickly licked her pussy. She let go of my balls and then I felt my pants being pulled down. She slid back on me a little.

"Now, I'm going to give you a blowjob while you eat out my ass," she said. "Don't worry, I've cleaned it. I'm going to pull my cheeks apart and put my asshole right over your mouth. Start by licking all around it and when I tell you, push your tongue in as deep as it will go. If you can hear me, start licking my asshole."

I licked her hole and tried not to gag. I felt her squirming on my tongue.

"Okay," she said, "Now I'm going to push out to make it easier to stick your tongue deep inside."

As I did what she asked, she pulled her cheeks wider apart and pressed down on me. It felt like my whole face was embedded in her ass. My nose pushed into her crack and I could barely breathe. I was gasping for air when she finally lifted up.

"That was good," she said. "Now go to work on my pussy while I work on you."

I felt her mouth suck me in as she shifted and put her pussy over my mouth again. Her juices were coming out so fast they soon covered my face. I stuck out my tongue and began moving it around inside her.

My cock soon grew hard in her mouth. She took her mouth away and her fingers pushed something onto it.

"I'm putting a cock ring on you," she said. "It's just a tight band that I'm pushing all the way up to where your balls meet your cock. It will keep you from coming until we finish."

As I continued to lick, she leaned forward so my tongue was caressing her clitoris. That got her body moving, and she began moaning. She rolled back and forth over my mouth and pressed down harder. She was masturbating against my face.

When she came, she slammed her pussy against my mouth. I gave up licking and just tried to pull back as she hit me like a punching bag. She almost knocked me out before she stopped and sat down hard on my face.

She rested there for a while and then got off the bed and leaned over me

"That was terrific, Ronnie," she said. "Now it's time for the cowgirl to ride the big bull."

She got back on the bed and lowered herself onto me and began riding, slowly at first and then faster and harder, slamming her body down on my stomach and knocking the wind out of me. My body responded and tried to come, but it couldn't. The frustration of being held back became painful. She slowed down, and I felt her vagina spasm as her body slammed into mine and collapsed on top of me. I was nearly unconscious by that time, so all I felt was her large breasts heaving against my chest.

It took her a couple of minutes to recover. I was so out of it that I didn't realize she had gotten off of me until she spoke again.

"Ronnie, you've been the best one so far. I'm making a scrapbook, and that will be in there. I really wish you had invited me up here, because then we'd be finished.

"Harold also has a goal in life. He's gay, and straight guys turn him on more than anything else. He calls them flowers, and his passion is to pluck the flowers. He's on a quest to deflorate a hundred virgin asses in his life. He calls it his 'Fuck-It List.'

"When I can seduce one of my fifty-three, all he does is film us. But if I need his help to get them to cooperate, then I give him my help in return.

"It's like they say on TV: When you want something enough, somehow you'll find a way to get it. It may be something you never imagined, but it always turns up just when you need it.

"Harold turned up when I was stuck, and at first I rejected the arrangement he suggested. But the next day I was watching a daytime talk show and a beautiful singer who was talking about her new perfume business said that if you help others achieve their goals, they will be eager to help you achieve yours. I had heard that before, but hearing it at that moment made me realize that working with Harold was the right thing to do."

I flinched as a finger entered my ass. I tried to get up, but was still exhausted from Catherine bouncing on me. Harold pushed me down hard and then stuck his finger in again.

"He's just putting a little lube in," Catherine explained from behind the camera.

Then his finger was gone and replaced by a tube that he pushed deep into me.

"It's to clean you out," said Catherine. "Once that's done, he'll fill you up with lube -- you'll be so full your belly will stick out. It's for your protection.

"You'll try to tighten up so Harold can't get into you, but all of the lube in your colon will want to get out, and eventually your ass will spasm. When it does, he'll slide right in without any trouble. He'd rather force his way in, but I made him do it this way.

"After that, he'll do a lot of things to you that you won't like and he'll make you do things for him. He hopes you'll fight him, but even though what he does will be a little painful and extremely humiliating, I hope you don't. That way he'll finish a lot sooner and it will be easier on you.

"You'll know you're nearly done when he puts you in the position where you're sitting on his lap facing me and the camera. When he does that, I'll take off your cock ring. Harold will grab your thighs and will rock you quickly on and off his cock. Then he'll pull you back and rip out of your asshole. He likes the video of him opening a gaping hole.

"As the gape starts to close, he'll drop you back onto his cock and begin the rocking again until he pulls another gape.

"You've got to try not to think of what he's doing and get yourself off as fast as you can. I'll help you by giving you a blowjob until you're hard. Then I'll use some of the lube and pump your cock for a bit. You'll have to take over and keep pumping until you come, no matter how much pain and humiliation you're feeling. As soon as you come, he has to stop and you're done.

"If I submitted the video to one of those amateur sex video sites, it would go viral. But I would never do that to a great guy like you. I'm certain you'll help me find more of my fifty-three men now that you understand how important it is to me. If you like, I can show you some of the video we made of your friend Jim before he helped me find you. But I'm sure you're not interested.

"I see you are starting to squirm and your face is squeezed together to help you hold in the liquid. Harold will take you to the bathroom to finish your preparations so we can start on his video. Before he does, I want to apologize again for inconveniencing you and thank you from the bottom of my heart.

"Before I started this journey, I watched celebrities on TV telling everyone to follow their passion, but I never understood what they meant. Now I know.

"The celebrities always thanked a lot of people for helping them. They said that when you have a big goal, it takes a lot of people working together to achieve it. I know from personal experience how right they were, and I'm deeply grateful for your support."

For background on the stories of edrider73, see "Author Interview: edrider73" by Literoticauthor. Tag: "author interview."