Anonymity

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Losing himself in the crowd leads to a bet.
7.3k words
4.71
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Part 1 of the 2 part series

Updated 09/22/2022
Created 04/28/2005
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EddyFox
EddyFox
33 Followers

Many thanks to papaya_lynne for helping with editing.

That's all I really wanted. I wanted to be left alone. I was nice, followed the rules, was fairly naive, and had some geeky tendencies, which means I was a perfect target to be picked on. My sophomore and junior years of high school were a particularly wan shade of hell. The low self-esteem, loathing to go to school, fear of turning the corner and seeing my tormenters, essentially robbed me of two years of my life. I went to a small private school, so with a graduating class of 37, there weren't many places to go to get away from it. My situation wasn't as bad as some I have heard of since I joined the ranks of the working man, but none the less, I was miserable. Years later, when I heard about the tragedy at Columbine High School, I realized that a new era had begun. One awkward kid who kills himself in a fit of depression is just one kid that we didn't get to in time. Two kids who take guns to their high school and eliminate their perceived antagonists, and anyone else who gets in their way, before turning the guns on themselves is an indication of a national epidemic of bullying behavior that must be addressed and remedied. There are now tens of thousands of unnamed kids who will find help when they eventually turn to a trusted teacher, parent, or mentor, and their suffering can end. The gunmen of Columbine are murderers and heroes.

Fortunately, I found a way to escape without resorting to a gun. The Drama Club. I could remove myself from my situation and be anyone, anywhere, any time. This was the ultimate in escapism. I no longer had to come up with witty lines and slick moves. My words and actions were prepared for me.

After high school, I went to a large college where, finally, I was a number. One student out of 25,000. I blended in, and no one noticed me.

I did, however, retain my penchant for the theater. My primary motivation was getting a role where pretty girls would be forced to kiss me. I took drama classes even though I was a computer science major, and I became heavily involved in the student-run theater. After a couple of roles and some tech work (lighting, set construction, etc.) I was approached to play a villain in a Shakespearian-era play because someone had to drop out. I have a good English accent, and a decent amount of agility. I got to sword fight, run one guy through, cut out a girl's tongue, and poison two people. What fun!

After the Saturday evening performance, Karen, one of the girls in my Shakespearian class, came up to me with a twinkle in her eye and a sly sneer on her face. I put on my most innocent face. She was very cute, about four inches shorter than me, with dishwater blond hair, and eyes so blue that I was sure they were contacts, although she assured me they weren't. She was not skinny, but her curves only made her walk more captivating. She tended toward black in her wardrobe, but then again, so did most people in the drama department.

"You bastard," she said, after a long pause.

"Thank you very much," I replied, sincerely appreciating her compliment.

"How can you be such a bastard on stage and such a nice guy in class?" she challenged.

And in one of those rare moments where I knew exactly what to say, I replied, "I would love to discuss that with you in great detail. Have you had dinner?"

"No, I haven't." With that, she looped her arm in mine, and we walked down to 9th St. to get a bite.

We spent a long time that night at the fast food place talking. What I pulled down waiting tables made this the expensive night of the week. They threw us out when they closed, so I walked her to her dorm. We lingered at the front door to her building.

"Well... thanks for dinner," she placed her hands in mine.

"You're welcome. Thank you for coming to see the play," I said as I pulled her a little closer.

"We should do dinner again some time," she said, pulling away from me a little.

"I'd like that."

With that, she moved forward quickly and pressed her lips against mine, and just as quickly, she moved away and slipped through her door with a "'Bye" as she disappeared.

The next thing I remember is arriving at the steps of my house.

********

It took a couple of dates, but pretty soon we were spending every waking moment with each other. School and work got in the way, but other than that, I followed Karen around like a lost puppy. She didn't seem to mind.

After about a month of this, I finally made the crossing into manhood. It was awkward and halting, but we managed to get through it. We then devoted lots and lots of time to practicing. I soon came to the realization that for guys, sex is easy. Enough stimulation, and bang, the next thing you know, you're snoring. The trick is to get the girl off. Make it more fun for her, and it will be a lot hotter in the bedroom.

I paid close attention to what Karen liked and didn't like. I also did some studying on the internet. I was soon proficient in making sure everyone had a good time every time. Karen volunteered that I was the best sex she had ever had. No guy in his right mind would ask that question. Why would you put a girl on the spot with the potential of REALLY deflating your self image? I told her that she was the best sex I ever had. It was true. She was also the only sex I ever had.

********

During these days of coital bliss, I would meet her in front of the theater department to go to lunch. One particular day, she left her purse in class and went back to retrieve it, urging me to go ahead and get a table at Hector's, our restaurant of choice, which was right across the street from the drama building. I started slowly across the quad, when I heard her call my name. I spun around and continued walking backward toward the street, when I ran into a brick wall. I went to the ground like a rag doll, books and papers flying everywhere.

"Why don't you look where you're going, you pencil-necked geek!" I only thought it was a brick wall I ran into. "I'm sorry. Are you alright?" Then I looked at him. What a stupid question. It was actually a 6'4" person doing his best to impersonate a brick wall. He looked like a Norse god more than anything else, with closely cropped blond hair. From what I could see, the only way I was going to hurt him was to hit him with a car. I started chasing papers and books as the breeze taunted me further.

"What do you think, geek? I usually swat things like you!"

By this time, Karen ran up. "Are you OK, baby." Before I could answer, Brick Wall Boy chimed in. "I'm fine, baby."

"I meant him." Karen handed me the last of my books.

"Why don't you go out with me some time, baby? I'll show you what a real man is like."

Karen shot me a look and I knew she was done with this guy. "Because he's better in bed than you are." I froze. I had no idea where that came from, and I had no idea how to respond. I was content with inaction until I thought of something.

That's when I saw her. She was one of the most beautiful creatures I had ever seen. She was probably 5'7" with dark brown hair that came down to the neckline of her top. She moved with the grace of a dancer and jiggled in all the right places. She moved up beside Wall Boy during the pregnant pause that ensued.

"There is no way that he is better than me in bed!" Wall Boy almost shouted.

The brunette screwed up her face in the cutest way, "WHAT!"

Karen put her hands on her hips. "Bet me money!"

The brunette tried again to get Wall Boy's attention. "Tom, what is going on?"

"This chick thinks that he's (pointing at me) better in the sack than I am!" The brunette gave me the once-over evaluation, and a smirk crossed her face. I'm just glad she didn't laugh out loud. Tom chimed back in, "How much?"

"Five hundred bucks," Karen replied, not skipping a beat. I knew she had just cashed out a $1000.00 "whole life" insurance policy her parents had been paying into since she was born. That money was supposed to get her through the school year. I said nothing for fear of messing up her bluff.

"You're on." I've seen the look that crossed Tom's face before. It's the one linebackers get right before a snap. His voice was low and calm. "How are we gonna do this? Swapping partners isn't going to work, because it will just end in a tie." My mind reeled at the permutations that statement hinted at.

The brunette spoke up at this point, her eyes following something in the distance, "We need somebody impartial. Jill!" I turned to see who she was shouting at. A girl about 5'6" with straight blond hair whipped her head around and ran over to the brunette as fast as she could, which was pretty damn fast.

She pulled up to a stop two feet from our little group. "Yes, Sister Michelle?"

"I have a task for you, Pledge." Sorority. I should have guessed. The hair on my neck rose up instinctively. I knew what was coming. "You will be the judge in a little contest we have going. You are going to sleep with Tom and with..." she looked at me trying to get my name. She was trying to exploit her power over a person in a compromised position. I was trying to not rip her head off. I couldn't figure out where to hide the body. "Ed." Karen had volunteered my name.

"...and with Ed, and you are going to tell us who is better in the sack. This will fulfill your obligation as a pledge." Jill's eyes lit up with that last sentence.

Karen chimed in, "Oh no. There is no way she's going to be fair. She's got a vested interest in your boyfriend coming out on top."

Michelle shot her eyes over to Karen, but otherwise, ignored her. "You will be fair and impartial... You will become a full sister AFTER you sleep with both guys, and BEFORE you announce your decision." Michelle turned to Karen, "How's that?"

Tom jumped in at this point, "She's with me at 5:30 today, and with Ed here the same time tomorrow. She'll need the recovery time."

"Sister, if I could move the time to 6:00?" I couldn't believe what I was hearing. "I have practice 'til 6:00."

"Done. Get everyone's phone numbers and addresses." I could tell Michele liked being in control. "We'll all meet at Hector's for lunch on Friday to receive your decision." I was stunned. Jill got my number and address quickly and hurried off through the quad. I stood there, dumbfounded. "Sweetie, are you ok?" Karen had finally noticed my total lack of responsiveness.

"What just happened?" I asked, fighting down the waves of panic.

"What do you mean, Sweetie?" Karen looked at me with surprise. I began to wonder if she had experienced the same reality that I had.

"You just bet Goliath $500 that I'm better in bed that he is! You've just arranged for me to sleep with that girl, who's name I can't even remember! He's twice as big as me, and his muscles have muscles! How can you be so sure that I'm better than he is?" My rant had expended itself.

"Sweetie," she said, as her eyes softened, she stepped toward me, and stroked my cheek with her hand. "Don't worry." I assumed a putty-like state. "I've dated guys like him in the past. You are so much more giving and caring than his type. He is not as good as you are, and the opportunity to take him down a notch was too good to pass up. Not to mention the $500. Letting you have sex with that other girl is a small price to pay." Her eyes caught fire. "Besides, are you complaining about your arranged sexual encounter?"

"No." My eloquence knew no bounds.

"Baby, you're gonna fuck her lights out." The smile on my girlfriend's face was an evil one.

********

Tom was sitting outside the frat house. He was restless. The restlessness you get before a game. Once you're playing, once you're focusing on your task, it's easy. It's the waiting to get started that's hard. Finally, he saw Jill come into the quad moving quickly, but looking winded.

"Sorry I'm a little late." Tom glanced down at his watch for the first time. "Practice went over. I've got to go take a shower. Can you give me 30 minutes?"

"No problem. Take your time. I'm going up to my room to get ready. Go up the stairs and it's the second one on the right."

"Thanks. I'll be right back." She jogged off back the way she came, cleats swinging from her bag as she went.

Tom thought to himself, "An athlete. That explains it. She moves well, but not graceful like a dancer, with power." Thinking back, she did mention something about practice. It must be soccer, or field hockey. He turned back to the frat house a little more impressed with this girl. As he entered his room, he looked around quickly. Maybe some sort of effort was called for, even if this was just a sorority stunt for her. He quickly assessed the tasks that would make the most impact in his room and dove in. He circled the room gathering empty drink cups, energy bar rappers, and cereal boxes, and depositing them in the trash. He returned to his room after taking the trash to the dumpster, and decided that the clothes on the floor needed to go next. It took three armloads, and the closet was 18 inches deep in clothes, but he managed to get the door closed just as there was a knock on the door.

When Tom opened the door, he found Jill standing there wearing a green rugby shirt with a white stripe across the middle and a pair of faded jeans. Her hair was wet and she smelled like she had just stepped out of the shower. Tom reassessed her looks again and decided that she was pretty. He invited her in and closed the door.

"Have a seat." The reality of the situation was much different than the abstract idea of a 'Sex Contest'. The details of their 'date' seemed less important, and, therefore, more difficult. Tom sat on the edge of the bed facing her as she sat in his study chair. "So...any questions about what's going on?

Jill shook her head. "No, I think I got a pretty good idea from earlier today." Tom started removing his flannel shirt. Jill followed suit and began removing her clothes as well. Tom reminded Jill of a Greek statue. He was 6'4' and his muscles jumped around as he took his clothes off. Soon they were both standing in the room naked. Tom's penis had begun to inflate to erection. Jill was very fit, and didn't jiggle seductively like Michelle did.

"Ready?" Jill nodded her head in response. "Then let's go!" With that, Tom lunged forward reaching across Jill with his right arm over his left. Jill reflexively lifted her arms to shoulder height, letting Tom do what he was going to do. She let go a yelp as he picked her up off the floor and spun her upside down. The result was that she was staring at his semi-hard penis as her thighs came to rest on Tom's shoulders. This guy was strong. There was no hint of effort in what he did. When Jill finally came to rest, Tom attacked her pussy with his tongue. The unexpected feeling rushed over her as she opened her mouth to cry out, but managed to stifle the sound. Jill's hands pushed against Tom's thighs, but he would not relent in his assault. After she got a hold of herself, Jill slipped her mouth over Tom's cock and began to bob her head up and down. The moan the escaped Tom's lips further stimulated Jill's slit.

Tom didn't have any trouble maintaining this position. Michele only liked it as a place to start. Jill was a little heavier than Michele, but somehow, her toned body was easier to hold. Tom was ready to move on to something else, so, having picked his position in the room specifically, he simply fell backwards on the bed. Jill released Tom's cock from her mouth and let out another yelp as she and Tom bounced on the bed harmlessly. He rolled Jill off him and got up off the bed.

"You scream like a little girl." A sneer crossed his face. Jill punched him in the arm with her fist, to absolutely no effect. The perfect reaction. Tom grabbed Jill's right ankle and pulled her to the side of the bed. He took the leg he had hold of and placed it over his right shoulder, putting her on her side. He moved in and slid the head of his dick between her pussy lips. She moaned as he crossed her threshold and pushed inside her wet hole. Tom started slowly, moving faster and faster with each passing moment. He grabbed hold of her leg to increase his leverage, and Jill, in turn, grabbed his wrist to increase it even further. This girl knew how to have a good time. As she started moaning and throwing her head back, Tom knew he wouldn't last much longer, so he pulled out, repositioning Jill while his cock had a chance to come back from the brink.

Jill gasped as Tom withdrew, but didn't have a chance to complain as he picked her up off the bed and deposited her on her back on the floor. Spreading her legs, he went strait for her opening with his dick. The effort of picking her up had served to stave off his orgasm for a bit. He started slowly again, building up speed. With no cushioning under her back, Jill's pussy was subjected to the full force of each of Tom's thrusts. Again, Tom felt himself nearing the edge, and just as Jill had begun moaning and biting her lip, he pulled out and stood up. Jill voiced her frustration, but didn't have long to complain. Tom grabbed her hand and pulled her to a standing position. He placed her arms around his neck and bent down picking up her right leg. After he had placed the back of her knee in the bend of his elbow, he coaxed her left leg into a similar position, grasping her ass in the process. He impaled her slowly on his rigid cock, easing her down until she hit bottom. Again he started with a slow rhythm, making sure she bottomed out with every thrust, controlling the tempo with his hands holding her ass. The tempo increased, and Tom was going for broke. Jill started gasping for breath as Tom pounded into her harder and harder. When the sweat glands on his back and neck released, Tom knew he was a goner. Fortunately, Jill exploded right before he did, digging her fingernails into his back to maintain her grip. After Tom emptied himself into Jill, his knees finally gave out, dropping him, and consequently Jill, back on the bed again. Jill was too spent to yelp again. Tom eased himself back on the bed, bringing Jill with him. They lay there, trying to regain their composure, until Tom's softening prick slipped out of Jill's pussy. Jill rolled off of Tom and leisurely began reclaiming her clothes. "I'm going to need another shower."

Tom laughed as he pulled on a pair of sweatpants. "Thanks for doing this."

Jill regarded him with a sneer that reeked of afterglow, "My pleasure."

********

It was 6:05. I had been ready since 5:15 and had a hard time sitting still for 45 minutes. I had already rechecked my preparations 5 times, and I was determined not to do it again. Just as I began to wonder if she would actually show up, there was a knock.

When I opened the door, Jill was standing there in a tee shirt and shorts. She had her gym bag over one shoulder and her field hockey stick in her hand. The cleats slung over the gym bag had managed to add to the dirt on her shorts. Her bangs were plastered to her forehead with sweat and she reeked of physical exertion and the outdoors. "Hi. Ed, look, I know I'm late, but I've got to go take a shower and change before tonight, so..." She turned to leave, but I grabbed her hand and pulled her gently back toward my apartment.

"No. Jill, come in. I want to talk to you."

"Ed, I'll be right back. I've just got to get cleaned up first."

"I've taken care of all that." My words caught her off guard, and she allowed herself to be lead into the room. I closed the door and took her bag and hockey stick from her and put them in the corner. I lead her to the couch and I pulled one of the kitchen chairs away from the table and sat directly in front of her. "Before we go through with this, I need to know something. I need to know that you are OK with this, and that you aren't being bullied into doing something you don't want to do."

EddyFox
EddyFox
33 Followers
12