Contest

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A Valentine's Day contest. Winner take all.
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My name is William, Bill or Will to my friends, and I'm just a normal guy. Really, I am. I'm not the good-looking heartthrob the high school girls drooled over nor do I have any unusual athletic abilities that would place me in the same category. However, don't write me off completely. I'm not bad looking. Maybe a little above average but average is definitely a good adjective. I'm five foot eleven and about 190 pounds. That puts me on the high side of average. I've got brown hair, short and parted neatly which puts me on the nerd side of average. I don't dress trendy. I'm usually wearing jeans and a denim shirt with white socks and loafers. Definitely on the average side of middle class.

I'm reasonably smart; at least I think I am. In high school I maintained a good B average. There's that word average again. I don't have any outstanding, above average abilities. At least I didn't think so until after I got married.

Let me explain. I didn't date much in high school. It wasn't that I didn't want to, I just couldn't get a real date. Just average I guess. I did have a number of nearly sexual encounters with the girls. Once in the back seat of my father's car that I borrowed for a date late in my senior year and another with a girl from another school during an unscheduled party at some guy's house whose parents had left him home alone for the weekend. It was an open invitation and I went along with the crowd.

Both events were short lived. In the car, just after the girl got her hands on my dick and I managed to get my hands on her bare tits, I got a cramp in my leg and the whole scenario quickly fell apart. At the party, a semi-drunk girl got me into an empty bedroom. We had our clothes off and we were on the bed. I was so nervous I couldn't get a decent erection and the girl left disappointed. After I was dressed again and walking down the hallway, she passed me with another guy in tow, headed for the same bedroom.

After high school, I began working on a construction crew. The pay was excellent but the opportunity to meet women not wearing hard hats was scant until the foreman's daughter showed up on the site. Of the twenty guys on the job that day, I was chosen to show her around.

Josie and I were both virgins when we married. I know I was and I believed Josie when she told me she was. After we were married we discovered a couple of things. We both loved sex, we couldn't get enough of it and although I was average in size, I had the ability to last a long time and recover quickly. About size, on a good day, I'm almost six inches in length erect but on most occasions I'm in the five to five and a half inch range. Josie says that's average. I don't know how she knows. On our wedding night, we managed to screw eight times and I came every time. Josie says that's not average. I don't know how she knows that either.

For over two years after the wedding, we fucked like rabbits every chance we could. Any time and anywhere, as long as the chance of getting caught was minimum. Once or twice in the morning before work, again after work before dinner and two or three times over the course of the evening and on the way to bed. All made possible by my less than fifteen-minute recovery time and an oversexed wife. Some therapists might have described our activity as hyper sexuality but it was normal for us and I'm grateful that we found each other.

I managed the pace well but eventually, Josie said it was wearing her out. She concluded, without any input from me, that, if she couldn't keep up the pace, I might be inclined to seek satisfaction elsewhere. Josie is an organizer and a problem solver. Her solution was to take charge of the situation, fuck me as much as she could without straining herself and provide someone else that she found and approved of to pick up the slack.

I didn't respond well at first to her solution. I really had no desire to bed other women. I told her she was enough for me. She countered that her ability to maintain my pace would wane faster than mine and early intervention was the best way to avoid deep problems later, after I became frustrated. She also assured me that I wouldn't necessarily be alone with other women. She fully intended to be part of whatever occurred. She then had the opportunity to rest while I maintained a faster pace.

I thought the whole idea seemed a little screwy but Josie is hard to argue with once she's made up her mind. I grudgingly agreed with her solution but made it clear, while we might entertain another woman on occasion, I was not in favor of adding another man to the equation. She assured me that, if she couldn't keep up with me she certainly couldn't have another man in her bed. So it was settled and Josie went about procuring resources. It wasn't as difficult as it might seem. She drew from a large number of divorcees, frustrated wives, and horny singles. She had interviews and made careful selections.

The next six or seven months went well. Whenever Josie needed a break, she had someone else laying by. Interestingly enough, the sessions with the other women, made me a better lover with Josie. I became more attentive and considerate of her. Our sessions together were more loving and lasted longer. I discovered that cuddling with Josie was very satisfying as were the hand jobs and blowjobs she began to use as substitutes to fucking. Josie actually enjoyed the sex enough that the number of times she provided substitutes declined over time but it did not cease entirely.

Valentine's Day was fast approaching. It would be our fifth Valentine's as married folks and Josie wanted to make it special for me. She told me to expect a surprise. Expecting a surprise seemed like an oxymoron to me but she stuck to her statement and told me not to prepare anything special for her. She would handle everything.

On Friday, Valentine's Day, I left work early, came home, showered and dressed nicely as I had been told to do. I wore a button down shirt with long sleeves, nice slacks with dark socks and almost dress shoes. I planned to finish the outfit with a grey tweed blazer with leather elbows.

When Josie came in, she appraised my effort, rewarded me with a quick kiss and headed for the bedroom to get herself ready. The result was stunning. She had my attention completely but she fended off my attempts to get physical and take new showers. We left for the restaurant about ten minutes later for a seven o'clock reservation.

Josie's choice was a favorite of ours. A small, pub-like environment with a full bar and the best Italian menu in downtown. Betsy, someone we had known since we moved to the area and one of Josie's recruits, handled the orders, the bartending, the serving and the bussing. It was an outstanding meal. Almost two hours later, we finished our overstuffed cannolis while nursing a second bottle of Chianti Classico.

Josie was in no hurry to leave. On the other hand, I could hardly wait to get her home and peek under the little black dress she was wearing. At times like this and other special occasions, she rarely wore underwear and I was itching to verify my supposition. Josie insisted we take our time. "After all," she said, "there's no rush."

At ten o'clock, Betsy announced last call and locked the front door. I looked at her and then Josie. "A little early for last call, isn't it?" I asked. While I was asking, Betsy lowered the lights so that I could hardly see Josie across the table.

"It's a special occasion. A surprise. She's just following the script."

"Script?" I wondered out loud.

"Down Willie," she said, "Patience."

She had never called me Willie before. Something was up and I took her advice.

About twenty minutes later the place was almost empty. There were a few stragglers but Betsy didn't seem to notice. Josie stood up and I stood up with her. She moved to a space behind the high partition that separated the front and back of the room. The rear space was large, with tables around the edges and a small dance floor in the middle. She looked around, grabbed a chair from a nearby table, placed it at one end of the floor and asked me to sit. It looked as if the surprise I was expecting might be developing, so I sat.

She stood in front of me and began to explain. "Today is Valentine's Day and I promised you a surprise," she started. As she talked, a number of figures emerged from the darkness and stood behind her. I counted six people, all women.

"The rest of the evening," Josie continued, "is a contest. The folks you see behind me, I think you know them, including Betsy and me, are the contestants and you are the prize."

I looked more closely. If I squinted I could make out more detail. I had seen all of them before. I fact, I had seen all of all of them before.

"Actually," continued Josie, "you are both the prize and a contestant."

"Contestant and prize?" I echoed.

"Yes. Tonight, we will contest your resistance against our determination. One of the eight of us may win you for the rest of the evening and all night. No restrictions. Everyone here is a volunteer and has agreed to the rules of the contest that I am about to explain to you. Do you understand so far?" she asked.

"I think so. One of you beautiful ladies can win me tonight. I kinda like that possibility but how do I win? Specifically, how do I contest? I don't fancy winning myself for the evening."

"Let me explain and I think your questions will be answered. All of us have experienced your remarkable staying power and quick recoveries. Tonight we will challenge the former. We will take turns attempting to cause you to climax and the one who accomplishes the feat will win you for tonight. I've reserved a room at the hotel up the block for you and the eventual winner."

"Interesting. How do I win?"

"You win if none of us wins. That is, after we've tried our best and you still haven't had an orgasm. And before you ask, and I know you want to, your prize is all eight of us for the rest of the night."

"I like it. I don't see how I can lose whatever the outcome. When do we start?"

"Well it is Valentine's Day and this is your gift but slow down a little. This is not a free for all. We're going to approach this in a fair and orderly manner. There will be four tasks. Each of us will take part in each task. One at a time we will try to make you cum in the same manner as each of the others. If you survive each task eight times we will move on to the next task and if you survive all four tasks, you win."

While she was talking, the women behind her were taking off their clothes. One after the other, I witnessed breasts and pussies exposed. As distracting as it was, I attempted to follow Josie when she continued.

"Here are the tasks we will attempt. First you will lay on the floor, naked." Betsy produced a large quilt that she spread on the floor in front of me, wiggling her naked ass in my direction as she did.

"We will draw a number for positioning and fairness, and, in turn, will lower ourselves on your erection. We are allowed to sit still for five seconds and then pump up and down ten times before allowing the next contestant to try."

While she was speaking, the women were passing around a large tube of lubricant and rubbing it on and in the equipment necessary for the contest.

"If you manage to outlast our best efforts, we will proceed to challenge two. We will again draw numbers for a different sequence. We will bend over; holding a chair and you will be allowed to enter each of us from behind in order. You are allowed the same five second adjustment period and then ten, only ten, strokes for each of us."

While I thought about it, Josie removed her clothing, joining the other naked women and took the lube from Betsy.

"Task three, should we get that far, involves a new sequence and each of us lying on our backs on the floor. We will hold our legs high and you will enter each of us in turn. As before, you have five seconds to begin a ten stroke encounter before you must move to the next contestant."

Josie finished with the lube and tossed it on a nearby table.

"The last challenge, I'm sure you'll do your best to get there, is eight blowjobs in a row. As before, each contestant will have an individual attempt to finish you off orally. This is the only task where individual technique is a factor and each session will be for twenty oral strokes as deeply as they wish. Failure allows the next challenger to try. What's different this time is that we will each have two attempts to finish you off. If you survive that, you win our unanimous appreciation and we will all walk to the hotel together. Are you okay with that?"

"Shit yeah," I said emphatically.

"I see you're ready to go. You need to take off your clothing and lie down on the quilt. From what I can see, you don't need help getting ready. Oh, three more things. You'll be blindfolded to insure impartiality and there is no touching or speaking. It might help you identify one of us and influence the outcome. One of us will help you navigate and aim if necessary. May the best woman, or man, win."

I stripped and was blindfolded. Several hands helped me settle on my back on the floor. Several seconds passed while the women decided their sequence and the first woman took her place over me. I could feel her approach and a hand, I don't know if it was hers, held my erection steady while she lowered herself on it. She settled down, took a deep breath before she started. Her ten strokes were over almost before they began and I felt the cold air as she removed herself.

It took only a few minutes for all eight to complete the mission. I had no difficulty holding out. I don't think Josie anticipated the restorative power of the cool air between each woman. I could sense the differences between the women but I couldn't tell who was who.

The second challenge began almost at once. I was helped to my feet and led to the back end of the first woman. Helping hands led me to the target and I slipped inside and rested for the proscribed five seconds before I pumped slowly in and out ten times. The cool air while moving to the second woman provided the restorative help I needed. Finishing all eight challengers was easier than I thought. A couple of them attempted to squeeze their vaginal muscles as I stroked in them but I had the stamina to fend off their attempts.

I had similar results with the eight missionary positions. The cool air transitions continued to aid my resolve.

The final test almost did me in. I stood with my hands behind my back. The women were very aggressive and the time between blowjobs was minimum as each one immediately replaced her predecessor, minimizing the effect of the cool air assistance. Every one of the eight had their own technique. Some were quite good. The third woman almost won the contest. The way she used her tongue put me on edge and when she pushed down on me until I was in her throat and undulated her muscles almost had me. I barely escaped. Somehow, I managed to endure the last five challengers. I panicked somewhat when I remembered there was a second round and woman number three would have another opportunity.

Incredibly, I survived all eight second attempts by mentally repeating MLB ERA and RBI statistics and focusing on the state of professional sports today.

I was led to a chair, sat down and was told to keep the blindfold on for a few minutes. When Josie removed the blindfold, all the women were dressed. I was the only one naked.

Josie stood in front of me. "I don't know how you did it. You win. We threw our best at you and you remain orgasm free. That's a situation we all plan to correct later tonight. Get dressed. We have a short walk to the hotel."

Josie and I went to the hotel and checked in. The rest of the women followed in one or two minute intervals to minimize suspicion about their intent.

Room 1721 was a small suite with two king-sized beds, a full sized sofa and two side chairs. The bathroom was huge with dual sinks, an oversized Jacuzzi tub and a walk-in shower large enough for more than one or two people.

Soon, everybody was present. The last to arrive, brought two bottles of Tequila and some margarita mix. When Betsy saw the gifts, she grabbed the plastic bucket and brought back a heaping pile of ice. We stood around looking at each other. You would think, after the events of the earlier evening there'd be little hesitation about what came next but you'd be wrong. I think everybody was waiting for Josie to make the first move. Well, not everybody. One of the women, I remember her name as Teressa, began to unbutton her blouse. Tess was probably the most endowed woman in the room. A couple of others came close but Tess had them all beat in my opinion. When she removed her blouse and dropped it on the floor, her breasts jumped at me.

Tess walked up to me, grabbed me behind my neck and pulled my face between her huge tits. I grabbed her ribs and held her close while I maneuvered, using one hand, to get my lips on one of her nipples. While we were enjoying the moment, several of the others began to remove their clothes while two others began to undress me, starting with my trousers.

Within minutes, everyone, except Josie, was naked, I was deep into sucking Tess' tits and someone was recapitulating challenge five.

Josie watched stoically until someone noticed she was still dressed. All activity paused and we all looked at Josie. "I appreciate your enthusiasm but I have one request. Only one. I would like to be the one to cause Mike to have his first orgasm of the night. It is my earnest hope that each of you have the experience yourself tonight but I'd like to be first."

Everybody stood back until there was no one between Josie and me. I walked over to her and kissed her passionately. "Thank you," I said. "Someday I'll figure out how your mind works but, for now, I love the results. You are the first, and only, love of my life. Please come and join me on the bed."

I began to unbutton her blouse. She stood, smiling, and let me undress her without help. When she was ready, I took her hand, led her to the bed and helped her climb up on it. I knelt between her legs and began to kiss her inner thighs. When I reached her clitoris, she reacted noticeably and pulled my hair to move me up her body. On the way to her other lips, I paused to acknowledge her breasts. At her insistence, I reluctantly continued up. We kissed and then twice more. She moved her body to position me properly between her hips and I entered her.

All the resistance I had built up over the last couple of hours dissolved. I immersed myself in her body and love. In less time than usual, Josie was writhing in my arms and obviously experiencing multiple orgasms. I relaxed and immediately began pulsing warm seminal fluid deep into her vagina. We held each other tightly, kissed several more times and rolled apart.

When I looked up, four women were sitting on the other bed, two were sitting on the sofa and Betsy was standing by the side of our bed. All were watching and seemed to be holding their breath. Their combined inhale when we parted was audible in the room.

Betsy waited several seconds and approached Josie on the bed. She got on her knees beside her and kissed her on the mouth while holding her right breast in her left hand. Josie kissed her back and pushed Betsy's face down toward her other breast. Betsy obliged and soon was kissing and sucking on one breast while squeezing the other.

The other six women watched what was happening on the bed and got some ideas of their own. Three women on the other bed began to kiss and fondle each other and two others on the sofa did the same. To my knowledge, with one exception, none of the women were lesbians so watching the action was fascinating and arousing. Tess, came up behind me, wrapped her arms around me, pressed her breasts into my back and began teasing my nipples with her fingers while kissing the back of my neck. I found out later that she was single and more aggressive than most of those present.