The Super Bowl Bet Pt. 01

Part 1: Introduction

Isn't it funny how a single event or two can change your whole world? That's how it was for me when I lost my dad to a heart attack about a year ago. My name is Dean and I'm a 35 year old account executive for a large real estate firm in Virginia. I've worked at the firm as a sales associate since college and have been told I'm a born salesman. Translated, that means I've got a lot of 'BS' with me. People can't help but like me due to my personality which is outgoing, funny and just a bit flirtatious. If I have one fault, it is that I am a "player" when it comes to women and relationships. I am not looking for a long term relationship and tend to play the field whenever and wherever I can. I have even hooked up with some of my co-workers and clients. The big "M" word is definitely not in my vocabulary.

This all changed when my father died last year. I became depressed and turned to work as therapy. I stopped going out and dating. I would spend 12 to 14 hours a day working in the office and would even show houses on weekends and nights. While work helped me to forget about my loss, it was evident that I was going to burn myself out and probably end up having a heart attack myself.

About 3 months ago I was called into the boss's office for a chat. The owner of the company, Ms. Williams is a bit older than me. She appears to be about 55 years old, but well preserved. She always dresses smartly in business attire that complements her ample body. I know she is a widow and has several children, but know little else about her. When I entered her office she smiled and asked me to sit down.

"I am very impressed with your work over the past six months" she said. "As you know, the real estate market is recovering from the recent economic slowdown and I have been considering expanding the business. I am looking for someone to take over a new residential sales team. The team will be in charge of promoting and selling homes in two new developments. I have contracted with the developer to be the exclusive agent for these developments and she wants an aggressive sales team to promote them as she needs to maintain her cash flow during the building process. The position will provide you with a substantial raise and you will get a commission for each sale your team makes. Are you interested?"

It didn't take me long to agree to her proposal. I would have three sales agents under me, plus a loan specialist who would assist in procuring any financing the buyers would need, and a secretary who would complete most of the paperwork for the real estate transactions. Best of all, I could pick and choose which properties I wanted to show, picking the ones with the best commissions and leaving the less desirable properties to the other members of the sales team.

The following Monday I arrived at work a little early in preparation for my first meeting with my new sales team. As I walked in and scanned the conference room I recognized several of the members of my team while others appeared to be new employees with the firm. Unfortunately for me, two of the team members were sexual conquests of mine from my earlier days. The other observation that I made was that all the team members were female. I made a mental note that this was definitely not the right time or place to think with my "other head". I certainly did not need a sexual harassment lawsuit now that my life was heading in the right direction.

I had been in my new position for about three months when my step mom invited me over for dinner. I arrived at her house, the one she inherited from my dad on his death, to find both of my step sisters were also there. "Looks like this is going to be one of those family get-togethers" I thought as I knocked on the door. My step mom opened the door and gave me a big hug as she invited me into the house. Both of my step sisters were helping her prepare dinner and I offered to set the table. I was never really close to my step family while growing up, but one thing I had to admit, her cooking was far superior to the fast food and frozen dinners I had been eating lately. We talked about our jobs and what was going on in our lives during dinner, but I sensed that my step mom had a hidden agenda which I was sure she would spring on me before the night was through.

Sure enough, when we were finished with dessert and I was getting ready to leave, my step mom said "Dean, you have been working entirely too much lately and not getting on with your life since your father died. If you don't ease up a bit you are going to end up just like your father. Are you seeing anyone now? Maybe Sarah can hook you up with one of her friends".

Sarah was one of my step sisters. She was a year older than me and worked in the emergency department at the local hospital as a nurse. I had been to a couple of parties with her several years ago, and knew that some of her friends were pretty hot, and they certainly knew how to party.

Sarah gave her mom the "death stare" for a few minutes and then smiled. "I'm not sure that my friends would be a good fit for Dean. You know we work a lot of odd hours, and besides, I'd be a little concerned about hooking him up with one of my friends giving his history with women." After a brief pause she continued. "I'll tell you what... My best friend Allison is having a small party next Saturday. It's a birthday party for one of the nurses in the unit. If Dean wants to come, I'll check and see if it is OK. If it is, I'll call later this week with the details. Just so you know, if you screw over any of my friends, I'll be real pissed".

I was not too thrilled with the prospect of going to a party with my step sister and spending a Saturday night with a bunch of people I didn't know. However, I agreed to go since I knew my step mom would keep pestering me until I did.

Saturday night arrived and at 8 pm I was at the address that Sarah had given me. I knocked on the door and was met by Allison. We made our introductions and she invited me in. Allison was one of those women that men dream about. She was about 5' 9" and 130 lbs. She had strawberry blond hair that was neither too long nor too short. The styling fit her to a tee. Her breasts looked to be about a 38D and her hips were well proportioned to the rest of her body. She had a fine ass and it was apparent she worked out daily to maintain a fine figure.

She introduced me to some of the guests then slipped away to mingle like hosts do. I ended up talking to the one or two people I knew and then sat down on the couch and tried to look entertained. About 11 pm the party was starting to wind down. I was also thinking about leaving when Allison came over and sat down with me on the couch.

"Need some company?" she said. "Looks like you've been sitting here alone most of the night."

We started talking and any thoughts of leaving were history. After talking for an hour or so we realized most of the guests had left. I told her I probably should be going as well, but asked her if I could see her again. She said that would be great and gave me her number. "I'll definitely give you a call" I said as I made my way to the door. As I opened it she grabbed my arm, pulled me close and gave me one of those hugs to die for while whispering in my ear "I hope it will be soon".

The Bet

Allison and I had been dating for about three months. I was quickly falling for her, even though I had not been able to get her into bed with me. Whenever I would suggest escalating the relationship, she would always say "That is something you will have to earn, but when it happens I'm sure it will blow your mind".

She constantly teased me through our months of dating. It certainly kept me interested, but a little frustrated as well. I was determined to keep up the attack doing things that I thought would please her like buying her flowers, doing things with her that she wanted to do rather than things I enjoyed doing, and giving her massages and back rubs. I knew what she wanted. The big "M" word and she was using sex, or more accurately "no sex" to drive me to it.

It was the Friday before the Super Bowl when I came up with an idea that I thought might work. We were having dinner at our favorite restaurant. I thought for a moment on how to best to proceed. It was after several glasses of wine that I finally came out with it.

"Allison, how about we make a bet on the Super Bowl?" She looked at me with a quizzical expression on her face, but didn't say anything. I continued. "The odds makers have it as a toss-up. So, you can pick either team. If your team wins, I will do whatever you say for a week. If your team loses, you have to have sex with me as often as I like for a week". I sat there and waited for the shoe to drop.

At least she didn't immediately get up and leave or slap me across the face. She sat there and stared at me for a few minutes and then smiled. "I'll tell you what, Give me 10 points and I'll take the Seahawks".

Wow, was I surprised. I knew the Seahawks didn't have much of an offense, and the Broncos, with Peyton Manning throwing TD after TD this year were sure to score a ton. I figured that this was a sure thing. I agreed immediately. After all, if I lost I would have to do some chores around her house, stuff I would probably do anyway. If I won, I would enjoy a week of sex, something that I had not experienced in over a year due to my self-imposed celibacy.

It seemed like Sunday would never come. I was like a kid waiting for Christmas day so I could unwrap my presents. The only difference was the present I was going to unwrap was Allison, and boy was I going to play with her. I could only imagine all the positions and sex we would experiment with when she paid up. She called me on Sunday morning and suggested I come over to her place to watch the game. She had a great media room with a large HDTV and sound system. I thought that was a great idea and offered to bring some pizza and beer. She said she would prefer wine, and bring enough for four as her two sisters would be there as well.

I was a little disappointed in hearing this, as I had hoped for some pre-game groping, but since I had already agreed, I felt obligated to go. "OK" I said. I'll be there about 4 pm."

When I arrived we put the pizza in the oven to keep warm and went into the media room to watch the pre-game activities. Ann and Ashley, Allison's sisters were already there kicked back in recliners watching the show. I had met both of them previously. Both were fine looking women. Ann was a little older than Allison and worked as a para-legal at a law firm in the D.C. area. She was about 5'10", 150 lbs and had auburn hair. Although she was a little heavier than Allison, she wore her weight well. The biggest difference between her and Allison was her attitude. I guess it was partially due to her job, working in a profession that was dominated by men, but I got the impression that she was a true feminist and had a bit of a chip on her shoulder. Ashley was younger than Allison and had a model's body. She was tall, in fact she was nearly as tall as me. She was probably 6' tall and 120 lbs. She had long blonde hair which she kept tied back and seemed to be more outgoing and fun-loving than her sisters. She was an aspiring artist and worked as a receptionist in a doctor's office when not painting. It was obvious that she loved to flirt and began doing so the minute I entered the room.

I sat down on the couch with Allison and we began drinking and watching the show. We talked about our jobs, the upcoming game and the commercials that were sure to be as entertaining as the game. After about an hour we got the pizza out and started pigging out. After a few more beers I was ready for the game to start.

The game started out badly for the Broncos and they were soon down by a couple of touchdowns. Allison looked over at me and said "I going to enjoy winning this bet and having you do whatever I want for a week."

As soon as she said that, Ashley chimed in. "What bet? Come on Allison, clue us in. Did you make one of your wild-assed bets with Dean? Let us in on the details!"

Ashley continued to prod for several minutes and finally Allison spilled the beans. "Yes, we made a bet on the game. If I win he has to do anything I want for a week. If he wins I have to have sex with him as much as he wants for a week. I took the Seahawks and 10 points. The way things are going so far it looks like he's going to have to pay up".

"Not so fast there Allison. There is still a lot of game left to play". I sounded like one of those commentators who tried to keep the fans interested even though the outcome looked pretty well decided. "The Broncos had some bad luck so far, but there is still plenty of time left. Don't count your chickens before their hatched."

Ann was beside herself. "How could you sell your body like that? What if you lose the bet? I can't believe you did that!!"

"Come on, Ann" Ashley said. "They've been dating for three months now. She's probably already let him have it once or twice just to keep him interested. Besides, giving the circumstances, she probably has a pretty good chance of winning this bet. I think it would be fun having a boy toy around here for a week. I wouldn't mind getting in on the action too. How about you?"

Ann thought about it for a bit, looked at the score and time remaining in the first half and then smiled. "OK, if he's willing, I'm in, but let's make this real interesting. I think the bet should be a week with each of us. That's a total of three weeks. Three weeks of sex for him or three weeks of service for us. What do you say? You up for it?"

I couldn't believe what I was hearing. I looked at Allison for guidance, but she simply smiled and said. "The ball's in your court. You don't often get a chance to have sex with three sisters. Especially three as hot as us. It's your decision."

Well I guess I was thinking with the wrong head. My good head was buzzing from the alcohol, and if I had been smart, I would have been paying closer attention to the game. "OK" I said. You're on. I win I get a week of sex with each of you. You win, I'll do what each of you want for a week".

The girls got up and huddled, then Allison turn to me and said "OK, but I want to make this official. No backing out on either side. Ann is going to type up the agreement for each of us to sign". By the time Ann got back with the document halftime was almost over. We all signed the agreement and she filed it away for safe keeping.

As the final seconds ticked off the clock the girls counted them down together. I couldn't bear to watch as the final gun sounded ending one of the worst super bowls in history, at least as far as I was concerned. Allison looked at me and then at the other girls.

"I know you cannot take off three consecutive weeks from work to serve us, so we will space this out a little. Tell your boss that you would like to take a week off since you just closed on that big deal last week. I am sure she will agree. You've been putting in too many hours lately anyway. It's time you took a little time off. Report here next Friday at 6 pm and be prepared to stay the week." After a brief pause, Allison added "Just so that you know, although you will be serving me beginning Friday night, both Ann and Ashley will be staying here for the week. There won't be a time that you are left alone, and they have my permission to punish you for any disobedience or failure to do as you are told".

As I left her house following the game, I began wondering what was going on. I had thought I would be doing a few chores around the house, but the way Allison talked, I would be supervised by one or all of them for the entire week and punished if I didn't perform well. I began to get a little nervous, but my "other head" became excited as well.