The Big Wager

Our betting dated back to a management seminar the two of us attended years ago. During the seminar Karen and I were pitted against each other in several of the training exercises. The trash talk over coffee and donuts led to a wager of dinner for the winning team. We took this competition between us back to the office. I guess one of the managers picked up on it and we were given competing territories. Over the years we bet on monthly sales totals, net gains, and any other bench mark possible.

Normally the wager was for lunch, a bottle of wine or a small dollar amount. Then this year the college bowl games were announced and her school was going to play mine in one of the minor bowl games. She had been a cheerleader and this triggered the super fan in her to ramp up the trash talk. After a few days of this constant "rah, rah, we are going to beat your ass" haranguing, I had enough.

"Ok, Miss Cheerleader, it's time to put up or shut up" I said.

She jumped on that like a cat on a mouse. "I'll bet you $100 that we cream your team" she shouted.

"No, this bet has to be more personal than money." "You have to risk your dignity," I replied.

After a long negotiation it was decided that the loser would be slave for the day. The game was scheduled for Saturday so Monday morning the loser would report to the winner's office and surrender. There were only two rules; the winner could not make the loser do anything that would cause them to lose their job and that the servitude would be from 8AM to 5PM.

Although my team was the underdog and was expected to lose by 10 points, I racked by brain to come up with embarrassing things for her to do Monday. I planned to have her wear my school colors, maybe declare to the office that she was a loser, and fetch me coffee and lunch. She apparently had other ideas.

I was watching the game at a local sports bar and it wasn't until late that night that I got the phone messages that Karen left during the game. It would appear that she wanted me to suffer for my team's lack of ability. The first message was right after they scored a touchdown on the kickoff.

"Hey loser, are you ready to do my bidding, are you ready to grovel at my feet, to be humiliated and embarrassed," she taunted.

It only got worse after their second TD and at halftime when we were down by 20 points Karen started listing my duties. "You will report to my office with a hot cup of coffee and then strip off all your clothes." "You will jack off so that I can have fresh cream for my coffee." "I'll keep your underwear in my desk drawer as a reminder that your ass belongs to me."

Things looked a bit better when we scored a touchdown late in the third quarter. No message until they scored a field goal late in the fourth quarter. The score was 23 to 7.

"My college roommate is visiting and you are going to serve both of us lunch around my pool." "You of course will be nude and both of us will have full access to your body." "I wouldn't rule out you having to masturbate for our pleasure and even have to eat one or both of our pussies."

Her elation was short lived. We ran back the kickoff from the field goal and made the extra point. In one of the flukes of college football they fumbled our kickoff and we scored again. Now the game was 23 to 21. With less than a minute to go in the game they were on the 50 yard line 3rd and 10. Instead of just taking a knee they tried a run to the right side. Our right guard managed to bounce the football loose and we recovered. A short pass to the outside put us on the 35 yard line. You guessed it, our kicker put that sucker thru the uprights and we won by one point. Her team's missed extra point early in the game came back to bite them on the ass.

On Sunday about noon I phoned her with instructions. "You will report to my office at 8 AM, you will bring me a hot cup of coffee, and you will not be even a minute late."

I then explained that she was to wear the blue outfit that she wore to the company party. She was to wear nylons with a garter belt. I should tell you that Karen is about 5 foot ten, 38C, with legs that ended at an ass that would make grown men cry.

Come Monday morning I was waiting at my desk when she sashayed in.

"Well master, what degrading, humiliating and dirty things do you have planned for the day" she asked.

"First thing is take off your underwear, that is your bra and panties and then I will give you the rules for the day."

I have always thought that a woman taking off her bra without taking off her blouse is one of the sexiest things in the world. The removal of the panties without exposing anything is another turn on for me. With the bra and panties secured in my bottom drawer I outlined the day for her. She was to do everything I asked promptly and with a smile. Anytime I felt she was disobedient I would cut one button off her blouse.

By lunch time I had a hand full of buttons and the only thing keeping her from flashing the entire office was the jacket of her suit. I had made arrangements for both of us to be out of the office for the afternoon at a "business conference" with some high valued clients. Both of our assistants would cover for us in case one of the suits from upstairs was curious about our disappearance.

A friend runs a gentlemen's club, aka a titty bar, which serves bar food for lunch along with a floorshow. Karen and I ordered a drink and then June, one of the dancers, came by to offer a lap dance. I slipped her a fifty and told her to give Karen the works. What Karen didn't know was that I had spoken to June on Sunday. In fact, half the club was in on the wager. When June finished the lap dance Karen was red faced, flustered and breathing hard. One might even say she was turned on.

"Ok, now you have seen how it's done I want you to go over to the table in the corner and give one of the guys a lap dance." "June will get the money for the dance so you had better be sure you get a big tip" I warned.

It is customary for the girls to be topless and for a little extra they will flash some pussy. I had June explain the clubs rules before sending my slave off to do my bidding.

With her jacket and blouse off and her skirt hiked up to her waist Karen was getting the attention of everyone at the table. She ended up giving each of the four guys a lap dance and put a bundle of cash in June's hand. She confided in me that one of the guys actually came in his pants.

It was time for the next event of the day. My girlfriend Terry owns a beauty salon with a massage table in the back. It is normally closed on Mondays but she agreed to do me the favor of helping with a special client. We stripped Karen down and put her on the table. She did not have a lot of pubic hair but did sport a landing strip. So we decided to add a wax job to the list. It was my job to rub in the lotion before Terry shaved her pussy and prepared the wax.

After the wax was removed with any trace of hair I once again rubbed oil all over her pubic mound from her clit to her rosebud. While I was doing this Karen was humping my hand and asking me to let her cum. Terry in the meantime reminded her about making me eat pussy if I lost. Terry then pulled off her pants and presented Karen with her own clean shaven pussy.

"You will eat my pussy until I cum, before you get to go home," she ordered.

With me rubbing her pussy, playing with her clit, massaging her rosebud, and slipping my fingers in her slit to tease the "G-spot" Karen was humping and wiggling all over the table. I kept her on the edge but did not allow her to cum.

By the time Terry came it was getting late. I loaded Karen in the car and headed for her house. I still had a surprise for her. Since I had not allowed her to dress at the salon she was nude when we pulled up in front of the house. I took her keys and opened the front door and she made a mad dash up the walk into the house.

I left her tied spread eagle to the bed with a blindfold on and waited down the street for her husband to arrive. Once he arrived I raced back to the salon where Terry and I made very good use of the massage table.

The next morning Karen walked into my office at 8AM with a cup of coffee and a note from her husband. This was not a note I wanted to open. As I was reading the note she calmly stripped off all her clothes and posed in front of me.

"Thank you," it began. "Last night was the best sex I've had all year. As you read this note Karen should be standing in your office stark naked. Please give her back her panties and bra since I would not allow her to wear any to work this morning. You should know I made the same bet with Karen and her college roommate that you made with her, only mine was for a week of servitude. You may now let Karen put on her clothes."

In the envelope was an invitation for Terry and me. We were invited to his house on Saturday evening for a pool party. He said that we would be the perfect couple to help discipline Karen and her over sexed college roommate.

Saturday cannot come soon enough for me.