The Super Bowl Bet Pt. 03

Part 3: The week continues

Sunday went much like Saturday. I woke early and orally serviced each of the women before making breakfast. They slept in later than on Saturday. I guess they were tired from all the activity of the preceding night. Sarah and Allison left for work together following breakfast and Samantha left to visit my step mom for the day. The list of chores for today involved a lot of outdoor activities. I was to work in the garden, do some landscaping and mow the lawn. I also had to wash and wax the three sister's cars. I worked while wearing a bra and thong panties.

Allison's yard was fairly well protected by shrubs. She had neighbors on both sides of her house and I could hear them working away in their yards. Her neighbor to the east had a two story house, and I swore I saw shadows in the second floor windows staring down into Allison's yard as I worked. The street she lived on was fairly quiet with only an occasional car passing by. Her front lawn wasn't large, but still would take a half hour or more to mow with her push mower. Even though I would be exposed, wearing only women's underwear, I was not given any additional clothing while I did the mowing. I practically ran with the mower trying to get done before being seen by one of her neighbors or anyone passing by. Ann and Ashley lounged on the porch watching me work and teasing me with comments about how nice my tan lines would be, and how they would need to buy me a training bra with padding since I didn't fill the one I was wearing out properly. Occasionally I would hear a horn sound as a car passed by. Once I head some cat calls and saw Ann waving to an older lady walking her dog on the sidewalk across the street. "If you run out of things for him to do, just send him my way. I definitely know how to treat bad boys, and he certainly looks like he has been bad to me" she said as she made her way down the street. Occasionally she would turn and laugh at what she had seen.

By the end of the day I was again ready to drop. I had managed not to earn any additional punishments, but my ass was still sore from Saturday's activities in the basement and the butt plug I was forced to wear all day. When Allison got home she said she wanted a steak and baked potatoes for dinner. She gave me a pair of woman's pants and a ladies blouse that she had purchased in my size and told me to put them on over the underwear I was wearing.

"Here is enough cash to purchase what we need for diner. Although you are dressed in women's clothing, you should be able to pass as a man unless you draw unwanted attention on yourself. Go to the local grocery store and pick up what we need. If you don't have enough money, then you will have to figure out how to make up the difference. I am sure there will be a few ladies there who might like a quickie in exchange for a handout. Hurry back because I am hungry and you don't want to keep me waiting. Remember yesterday morning! By the way, don't even think about trying to skip out. Your chastity device has an integrated shocking device that will start shocking your balls should you travel more than a mile from this house. Fortunately there is a grocery store about half a mile from here. They have really good prices and is owned by a friend of the family. Now get going."

I got dressed and got in my car. Although I was dressed in female attire, I agreed that it wouldn't show unless I had to stop and have a conversation with someone. It felt good to be away from the ladies, even for a short time. I thought about running, but figured the consequences were not worth the risk. I just had to endure this week, and then a week with Ann and another with Ashley then I would be free. I'd go back to work and never think of getting in another relationship like this. There definitely wouldn't be any more bets like the one I was foolish enough to make.

The grocery store was easy enough to find. I parked the car and went inside. They were not real busy for a Sunday evening, in fact I think they were getting ready to close. I picked out some steaks, a bag of potatoes and some salad and started for the checkout. I only purchased enough for the girls as I wanted to be sure I had enough money for everything. As I got up to the cashier, I noticed her staring at me more than normal. I started to become more self-conscious. Could she see the bra under my blouse? Did I appear overly nervous, or was I just imagining things? When she finished ringing up my purchases she said it would be $43.54. I panicked. Allison had only given me $40.00.

"I'm afraid my girlfriend only gave me $40.00. I guess I will have to put something back"

"Wait a minute" she said. "Is that a bra you're wearing under your blouse? I bet you even have panties on under those pants. I noticed the panty lines as you walked in. What's your girlfriend's name? I know most of the people in the neighborhood, maybe I could give her a call?"

I told her what she wanted to know and she whipped out her cell phone and called Allison. After a brief conversation she turn back to me. "Allison is a dear friend of mine. I've known her family for years. I think we can work something out here. Let me just close up and lock the door. I have an office in the back and you can work off the balance of what you owe. What was it, $3.54?"

We headed to her office. What choice did I have? She was older than me, probably in her early 50's. Her hair was starting to grey a little. She had large, sagging breasts and an ass that would tax any seat and hang over on both sides. I guessed she tipped the scales at well over 300 lbs.

"Let's see. For $3.54 I think I should be entitled to a couple of orgasms. Since I know you have on a chastity belt, I guess I will have to settle for your mouth. Lay down on this bench, face up. I'm going to sit on you face until I've had my fill, and it's been a long time since I've sampled any oral from a white boy."

Oh. Did I forget to mention, she was an African American and she enjoyed having white boys under her. She put all of her weight on my face, shifting every so often to allow me to get a gasp of air. First she sat facing my feet, placing her pussy over my mouth and wiggling her ass so my nose was embedded between her ample ass cheeks. She rode me like that through an earth shattering orgasm and then turned so that her ass now was over my mouth and my nose rubbed her cunt. She rode me like that to a second orgasm, rubbing her cunt on my nose and forcing me to stick my tongue up her ass, licking her rosebud and occasionally penetrating it. After about 45 minutes she was done. She refused to let me wipe my face and sent me on my way.

I arrived at Allison's a few minutes later to find her furious. "That's two punishments for you. One for keeping me waiting, and the second for not figuring out how to pay for dinner on your own. Emily had to call here instead of you confessing you were my slave and offering to service her in exchange for your purchases. From now on, you will be buying all the groceries we need for the rest of the week at her store, and I will not be giving you any money to make your purchases. Now go fix dinner, your punishments can wait until after we eat."

I was getting more and more worried. More women were using me every day. I had now served six different women, and it was only Sunday. No telling what the rest of the week, or the two additional weeks of service had in store for me. This was also the first time that Allison had called me her slave, and that scared me even more. I had to find a way out of this predicament.

The punishment session following dinner was not as severe as the previous night's. I received a paddling and a whipping from each of the ladies. The butt plug was removed and I was told to go clean it. "You're lucky she doesn't make you clean it with your mouth" Sarah said as I went to wash the plug. When I returned I saw that Allison had a larger plug in her hand. This one was metal and had a large head which narrowed to a slim neck.

"This one is designed to stay in place without the need of a strap. You will wear it until tomorrow night when I replace it with a larger version. If it should fall out, you will ask the first woman you see to replace it for you. You will also receive a punishment for losing it. If you need to use the bathroom, you will have to ask someone to remove it for you and reinsert it when you are finished. Again you will receive punishment for its removal. Now off to bed. I want to make love to Sarah and you will just be in the way."

The rest of the week followed in much the same manner. Ann and Ashley had to go to work each day. Ann seemed to be more of a sadist than the rest of the ladies, so her absence was a relief. Allison or Sarah were there to supervise when not working and the step sisters were in and out. Most of the ladies were present at night, but since all were busy with their jobs, the amount of punishment I received was minimal. I did housekeeping, odd jobs around the house and in the yard, and of course, made my daily trip to the grocery store.

On Friday morning Allison announced that tonight would end my week of service to her. I still would have a week of service to Ann and Ashley to perform, but those would be scheduled at a later date. Tonight there would be a party and I would be the guest of honor. Allison would not tell me more but stressed that I should be sure that the house was immaculate, that I prepare refreshments for those attending, and that I should be prepared for a long night.

"How many should I prepare for?" I asked.

I'm expecting around twenty or so.... Give or take. You never know whose going to bring a friend to my parties. They're the talk of the town you know. By the way, since your week is up tonight I have decided that if you please me during the party tonight I am going to give you a little reward"

"Reward" I thought, "If her rewards are anything like her punishments, I think I might pass."

"If you please me, I am going to let you have sex with me, as much as you like, for the next week, Just remember, I wouldn't plan any pay backs for this week, as you still have two additional weeks of servitude to fulfill. I can guarantee you that my sisters will be glad to punish any inappropriate behavior. But just so you know, when it comes to sex, I am insatiable. You already know of my cock sucking ability, and I love vaginal and anal sex just as much, so if you're interested, you better stock up on those little blue pills because you're going to need them."