The Super Bowl Bet

Chapter 4- The Party

I was totally confused all morning. Allison had as much as told me she was going to screw my brains out next week. If she had told me this last week, I'd be the happiest man alive. After the week of hell I had just endured, I wasn't sure I wanted to take her up on the idea. I also still had two weeks of hell to endure, one with the sadist Ann and the other with Ashley. I wasn't looking forward to either.

By noon I had the house in order. It really wasn't that dirty as I had spent most of the week cleaning this or that. I still had to make refreshments for the party which meant heading down to the grocery store once more, a task I wasn't looking forward to. As I drove to the store I began wondering about the party. Was this going to be some of Allison's co-workers coming over for a get together like the party where I first met Allison, or was this going to be something a little more exotic with me serving a bunch of horny women? I wasn't in any real hurry to find out.

I arrived at the grocery store about 12:30. Emily was there with a grin on her face as she saw me approach. "What can I do for you today?" Emily asked. "Need some supplies for the party tonight?"

My stomach immediately started doing summersaults. "Ah, yes ma'am. I need some stuff for snacks, and I guess I better buy some wine and beer. Do you know what Miss Allison normally serves at her parties?"

"Sure" she said. "I go to them all the time. She has these things about once a month, but it's been awhile since she's had any special entertainment for us. Tonight should be special. I'll get one of the girls to get everything you need. Come on back to the office and we'll arrange for payment. It'll be a pretty big bill so I hope you can pay."

Well the bill for all the party supplies was over 200.00. Since I didn't have any money, I had to agree to serve Ms. Emily for a week to pay the debt. She said I didn't have to serve her now as she knew I would be busy all afternoon, but she would be getting some freebies tonight at the party. As I left the store I had little doubt that tonight was not going to be a fun night for me. Little did I know how right I would be.

By 6 pm the sisters were all there. Allison, Ann and Ashley were getting ready upstairs as I was putting the finishing touches on the refreshments. Allison came down and said it was time for me to get ready. She handed me a thong and told me to put it on. I could wear what I wanted over top of it. "Maybe this won't be so bad" I thought. "At least she's letting me wear normal clothes over my panties."

My step sisters were the first to arrive. To my surprise, entering behind them was Jane, my Step mother. I blushed a little and hoped that Samantha and Sarah had not told her too much about my week. A few other ladies arrived over the next 15 minutes. Three or four I recognized from the previous party I attended. Allison greeted them and I assumed they were co-workers. Around 7 pm Emily appeared along with two of her employees I recognized from the grocery stores.

"These are my daughters Rachel and Cecilia" she told Allison. "Hope you don't mind me bringing them. They've never been to a party like this, and I thought it would be a good learning experience for them."

"Not at all" Allison said. "We're all one big happy family at these events and tonight will prove to be a special night, just you wait and see."

I went to work serving drinks and greeting women as they arrived. I could see that this was to be a hen party, as I was the only male in attendance. By 8 pm there were over 20 women present ranging in age from about 20 to over 60. Some were well dressed, as if coming straight from an office somewhere while others were obviously dressed more casual and ready to party. At about 8 pm I went to answer the doorbell. When I opened the door I gasped and took a step back.

"Is that any way to greet your boss" said Ms. Williams. Entering with her was the human resources manager of the firm, Ms. Reynolds and Mary, the loan manager from my team. "I think you know Robin and Mary. Please take our jackets and bring us a glass of wine. By the way, I hope you enjoyed your vacation this week, you'll have a lot of catching up to do when you come back to work Monday."

I was shocked to say the least. Here was my boss, the HR director and a co-worker of mine at a party where I was sure to be the entertainment before the night was through. My step sisters and step mother were here also, along with about 20 other women I didn't know or barely knew. I had a feeling something bad was about to happen.

After I had served everyone drinks, some were on their second or third by now, Allison got up to speak.

"Can I have everyone's attention? Several months ago I met Dean here at a party. We have been seeing each other since. Dean was foolish enough to make a Super Bowl bet with me which he lost. He has been forced to serve me for the past week in any way I wish. He was also told that he must serve any woman who enters this house. Therefore, tonight he will serve any of you in any way you desire. Feel free to punish him if he fails to meet your needs. I have also told him that if he performs well tonight, that I will reward him for his efforts. At the end of the party I will take a vote to see if he will be rewarded or not. Have fun and let the party begin."

I was told to strip to my thong and the ladies went wild. Allison sat back and watched as several of the women came up to me and started rubbing their hands over my body. The Alcohol was making the women lose any inhibitions they had and soon I was orally pleasing one after the other. My thong was ripped from my body and there I was naked in a room with over 20 women. I lost track of how many pussies and asses I serviced and how many women rode my cock. I remembered Emily sitting her large ass on my face followed by her two daughters. My step mom mounted my face and rode it like she hadn't had sex forever. After a while, I was no longer able to maintain an erection and my cock was so raw I couldn't stand anyone even touching it. My tongue was numb and I could no longer differentiate the taste of pussy from ass. I was nearly ready to pass out when Allison stopped the action.

"I think we have succeeded in wearing him out sexually. Is everyone satisfied?"

A chorus of "NO! WE WANT MORE" repeated over and over again. "Very well then, since he has failed to satisfy you he must be punished. Ann, would you go to the basement and get a variety of paddles and whips so these ladies can show this boy what happens when they are left unfulfilled?" In the meantime, Allison continued. "OK. I have been training his ass for the last week, let's see what he's learned."

I was tied face down over a padded bench with a spreader bar attached between my ankles. Wrist restraints were attached to my wrists and a rope tied from my hands to my ankles. The rope was pulled tight bending me over and totally exposing my asshole to the crowd. Several strap on harnesses were produced. A variety of strap on dildos laid out on the table. Some were smaller than the anal plugs I had been wearing all week while several were much larger. I started to cry as I realized what was about to happen. I was lubed up and the first lady stepped up to plunge her weapon into my ass. After three or four of the women had their way with me Allison came up to me with Ms. Williams by her side. Both were wearing harnesses with an extra-large dildo attached. I guessed them to be at least 10 inches in length and over 2 inches in diameter. I was sure it was larger than anything I had taken to this point. Allison began. "Tonight I will ask Dean to marry me. He will have until next Friday at this time to decide. If he accepts, he can expect many more days and nights of serving women. All women will be his superiors. He will be subjected to weekly play parties such as this, and he will be loaned to any of my friends upon request. Now, I think it's time I fucked him right." Allison mounted Dean and thrust her dildo in with a single stroke. She waited a moment before brutally raping his ass with her phallus. After about 20 minutes she withdrew and Ms. Williams stepped up. "I hope you accept my daughter's offer of marriage" Ms. Williams said. "It will be good having a man, I mean boy, around the house again. I'm sure we can find some additional duties for you at work as well. Since you'll be marrying into the family, I'm sure you won't mind the added responsibilities. Of course, if you decline her offer, you will have to find a new job as well. There's no way I could continue to employ a pervert like you in an office full of women unless I was sure you were under the control of someone like my daughter."

I looked up at her and couldn't believe what I had just heard. My boss was Allison's mom. And if I didn't agree to marry Allison, I would lose my job. I think this is known as a no-win situation.

Ms. Williams continued. "Just so you know, I have copies of all the pictures that were taken this week including those taken tonight. I have made a copy of your contact list on your phone which includes many clients and business contacts. If I should send them a copy of these pictures, I am sure finding another job anywhere within a hundred miles of here will be next to impossible. If I post them to the internet, you might as well apply for bankruptcy and look for a job digging ditches somewhere. Maybe Emily would hire you." With that Ms. Williams grabbed my hips and thrust with all her might sinking her massive rod balls deep into my rectum. She withdrew completely and thrust again. This time she got into a rhythm and rammed my ass for what seemed like 30 minutes. I cried the entire time.

By 1 AM the women had lost their enthusiasm to play. They continued to drink wine and beer and talk about the night's activities. Allison realized that there would soon be a problem given the number of women present, the amount of alcohol consumed and the number of bathrooms available for use, so she came up with one last indignity for me to endure.

She went down to the basement and soon returned with what looked like a portable potty that looked similar to one that would be use while camping. She gave me the toilet and told me to place it in the corner of the room with a piece of plastic under it to prevent spills from messing her floor. As I placed the toilet I noticed an opening between the legs. Miss Allison told me to stick my head into the opening face up. She attached my wrists to the toilet's legs and placed a plate around my neck which locked me into place underneath the toilet seat. She lifted the lid and inserted a funnel in my mouth that ensured anything deposited into the toilet would end up in my mouth.

As she was doing this several of the women gathered around to watch. They made comments like "No, she's not going to make him a toilet" and "Oh, I think I feel a pee coming on." The comment I feared most was from one lady whose name I didn't know who said "I think I'm going to be sick, I shouldn't have drank so much."

Fortunately for me, she got sick before Miss Allison had me ready for use, so the woman rushed to the bathroom rather than vomit in my mouth. While she was gone, the other women got the urge to pee, and one after the other they sat on the portable toilet to do their business.

The party broke up about 8 am Saturday morning. A vote was taken to see if I had passed the test of the party and should be rewarded. The vote was close, but I passed. I noticed that Ms. Williams both my step sisters, and my Step mother voted against me. Still, I was to be rewarded with a week of unconditional sex.

The last of the guests didn't leave until noon. I was kept as a toilet until that time. When I was released, I was given my clothes, car key, phone and wallet and told I could go home.

Allison said "I agreed to have sex with you anytime you like this week, whenever you're ready just give me a call. Right now you better get some rest, you look kind of tired; and you smell like piss too."

So now I sit here on Sunday afternoon. I slept for 16 hours straight. I've cleaned myself up and look like nothing unusual has happened. When I return to work tomorrow, I am sure most of my co-workers will know of my ordeal, I'm not sure how I will face them. I need to decide if and when I will have sex with Allison this week, and more importantly if I will accept her offer of marriage.

I don't know how I will cope with a life where I have to submit to her at home, and most likely her mother at work. What's worse, I don't know what I'll do if I reject her offer and my experiences are exposed to the world. All my friends and co-workers and even my step family will abandon me. I'll have no job, no way to pay my bills, and in reality, no life. All because of a silly little bet.