Kelly Gets the Scouts Together

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It's 2010, Kelly and her friends get ready for Halloween.
8.5k words
4.27
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Part 1 of the 2 part series

Updated 06/10/2023
Created 09/22/2021
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The late afternoon NFL games for Week 4 had just ended when my phone rang. It was my friend Mike who ran the weekly football pool. I figured he was calling to gloat over winning that week. I had an especially terrible week of prognosticating, so I knew I was not going to be the winner. I hit the answer button and prepared for the worst.

"Hey man, guess who won the pool this week."

"I know it's not me, so I guess it is you and that's why you're calling."

"I wish" he said, "but I did just as badly as you. No man, Kelly won, she got 10 right and with just the Sunday and Monday night games left no one can catch her."

"You cannot be serious" I said. "She doesn't know anything about football. I just have her fill it out to get more money in the pot."

"The way this week's games went; it was probably better to not know anything about football and pick by team colors or cities or whatever else she uses to choose than. Just figured I'd let you know you guys are $200 richer so you can celebrate."

"Thanks; I'll let her know when she gets home. See you tomorrow."

I was in complete disbelief. How in the hell did she win? I'm never going to hear the end of it. When I first asked her to join, she wanted no part of it saying it was a waste of money. I convinced her that I would win at least twice a year, (which I did) so we were practically guaranteed to come out in the positive each year. She was still unsure, so I sweetened the contest, giving her extra incentive if she ever won it, which I knew she would not. I was so sure of it, that we had made a one-sided wager. If she ever won, I would wait on her hand and foot for an entire week. Whatever she wanted, whenever she wanted it. I would have to prepare myself mentally for what was to come.

"Are you serious!?" she screamed excitedly when I told her upon her return home. "That is wicked awesome" she said with a big smile on her face channeling her New England accent which didn't come out too often anymore.

I told her Mike would have the $200 for her in the morning if she wanted to pick it up or I could do it. She decided it would be more fun for her to pick it up so she could "make sure" it was all there.

As we got into bed for the night, she hadn't said anything about our side wager. I was hopeful she would have forgotten about it or just decided the money was enough and be happy with it.

"What are you going to do with the money," I asked, trying to keep her focus on that.

"Oh, trust me I have plans for MY money" she said with a smile. "This is going towards my Halloween costume. Maybe I can get a little extra done to it. Make it look more authentic."

Kelly and I loved Halloween. Two years prior we had quite the night with one of her friends. It was the first time we had both been together with one of our friends. Kelly and I were very much in love, but I knew that sometimes you needed a little change of pace. Thus, we agreed to be honest with each other should we ever look for a fun night with someone else. Kelly had taken advantage of our agreement once, but I was not certain I ever would. The desire was there but I was unable to get past my own trepidations to actually go for it.

"Are you ever going to tell me what we are going to the party as so I can make sure to get my costume ready? The closer we get to Halloween the harder it's going to be to find whatever I need."

"You already have your costume; you just don't know it yet. Trust me, you'll be fine and ready to go before the party."

"Alright," I said as I tuned off the light and gave her a quick kiss. "Good night."

It had been a couple of weeks since her victory and still no mention of our side-wager. I figured I had lucked out and the money had been enough for her. Halloween fell on a Thursday this year so the party we had been invited to would be held on the Saturday before. We were going to one of the area Country Clubs per an invite from her friend Sara. I was worried the night was going to be nothing but pressure to join but Sara convinced us that would not be the case. The only requirement was that everyone had to be in costume.

It was two weeks before Halloween when Kelly finally hit me with the reminder of our side wager. She sent me a text message about an hour before I got off work which reminded me of our agreement. She said she wanted to start the week that night and sent me a shopping list of things to get. 6 bottles of wine (3 red/3 white), vodka (regular and whipped cream infused) and any other liquors we may be out of at home.

I inquired as to why we needed so much all the sudden. She let me know that her friends would be coming over Friday night for dinner and spending the weekend so they could all go out Saturday for a girl's day and make sure their costumes were ready. She made sure I knew that the couch was going to be for me both nights as we only had one spare bedroom. She would sleep with one of her friends in our bed and the other two would sleep in the guestroom. I was not thrilled with this idea, but a deal was a deal and when it was time to go, I picked up the wine and liquor as requested.

When I got home the rest of her plan was revealed to me. I had a half day on Friday, so I was to go shopping once again for dinner and make dinner for her and her friends Friday night. Again, this was a "Girl's Event" so I would not be joining them, just preparing for them and serving. I objected that the deal was that I was to do as she asked for a week but not for others too. We discussed that and agreed that if I did this, my penalty would end on Sunday instead of going the full week. I agreed to the terms and asked what she wanted me to make. Surf and turf was the response. Oh, wonderful I thought.

After getting off work after lunch, I went to the butcher to pick up the smallest ribeye's they had, figuring the ladies wouldn't want a huge meal. After that was the market for crab legs, fixings for a nice rice pilaf and what I needed for Caesar salads. When I got home, I cleaned up a bit and got the table set with a fresh tablecloth and the place settings. Still had a couple hours so made myself a big dinner before getting started on everything else. When Kelly got home, she looked around at what I had done and complemented everything. She asked if I would set up the outdoor heaters on our enclosed patio in the back in case it got a bit too cool out there if they wanted to use it. I set up the heater and switched out the lightbulbs, one black and one orange for ambiance. A couple of pumpkin lights on the patio table completed the look.

Everyone was supposed to arrive by 7:30 so I started prepping at 6. Got the salad made and set in the refrigerator and prepared the pilaf for the stove. Got the large pot of water boiling for the crab legs and seasoned the steaks. Kelly's friend Stephanie (never Steph) arrived right at 7. Out of all her closest friends I never really connected with her. She was 5'6" just like Kelly but had dark brown hair compared to Kelly's light brown. Her nose was kind of pointy so I figured she would be going as a witch to the party next week. I know I should not be stereotypical, but I can't help it. Other than that, she was a beautiful woman. Nice smile, small breasts, I would guess they were 34A's. The couple times I had seen her in a bikini she didn't fill it out.

Nicole was the next to arrive, doing so just as I got the steaks on the indoor grill. I always had a great time with Nicole and her husband when we would get together. She was the tiniest of the friends, standing at 5'3." Her hair was almost identical in color and length to Kelly's, but the biggest difference was the breasts. Nicole had hers augmented to 36C's a couple years back. I thought what she had before was fine and that these new ones were too big for her frame, but she liked them and according to the looks and comments she would often get, so did many others.

Dinner was served at 7:30. To no one's surprise, the final friend, Sara was not on time. Sara was the youngest of the group by about 12 years having just turned 22 over the summer. She and Kelly met because of her ex-boyfriend who had worked for Kelly. The guy was a total waste of space and we all wanted to throw a party when he left. Sara had dropped out of college to move in with him, thinking he was the one, to her parents' chagrin. The good news for her was that her parents had money; I'm not sure what they did or owned, just that they were loaded. They took care of her financially, getting her a nice apartment and ensuring she had everything she needed on the promise she would go back to school. She was finally going to go back to college for the spring semester. It was actually her parents' invite that got us into the party next week.

Sara arrived just as the others started eating. From the looks of her, she had just come from the gym, where she practically lived. Before dropping out, she had been a cheerleader. The couple games we went to, it was hard not to watch her instead of the game. Michelangelo could not sculpt a more perfect body in my opinion. She was the tallest of the group standing at 5'9" with jet black hair and blue eyes that always appeared to sparkle when you looked directly into them. Her body, from what I have gotten to see of it, had no imperfections. Tight, tanned and lean from top to bottom. Speaking of her bottom, absolutely no complaints there, it was exquisitely round and firm. Picture Catherine Zeta-Jones in the training scene from Entrapment where the camera focuses on her ass (or perhaps her stunt doubles) as she goes under the wire.

Whenever I saw her, I always thought, man if I ever had the opportunity with her, I'd...remember I was married and even though we had the agreement between us, I felt close friends were unavailable.

Each had two glasses of wine in front of them, one red and one white since I didn't know which each would prefer. To my amazement, I had to refill them rather quickly.

Why aren't you eating too?" Sara asked.

I explained I had eaten earlier to make sure everything was ready to go. Kelly decided to pipe in at that point.

"Actually, the real reason he is not eating is because he is mine to command all weekend long," she said smiling at me.

"What do you mean?" Stephanie asked.

"A couple of weeks ago I proved I know more about football than he does. I won $200 in his football pool. The deal was that if I ever beat him, he would have to do anything I asked of him for a week but since we had this weekend planned, I told him that I would only make him do it through Sunday."

"Is it only what you ask of him or do we get to play too," inquired Nicole.

"Sorry ladies, only what Kelly asks," I said quickly.

"No, no, no" Kelly quickly interjected. "The deal was you do what I want, and I want you to listen and do what they want too."

I motioned for Kelly to meet me in the bedroom right quick to have a discussion. I explained I was displeased that she was including her friends into our little arrangement. Embarrassed enough already that she let them know what was going on.

"Don't get mad and embarrassed. Look what you have out there. Four women who have nearly finished two bottles of wine in less than an hour. They are all staying here tonight and tomorrow. There will be a lot of drinking going on. You are the only guy here. Who else are they going to flirt with all weekend? Not only that, but you are also going to be the first person to see us in our costumes after we pick them up tomorrow. See how sexy we are dressed up as...oops almost spoiled the secret there. Couple more glasses of wine and I probably would have. Just give me this weekend for fun with the girls and I am most assuredly going to pay you back ten-fold later, ok?"

Kelly was good at keeping her promises and she made this one sound special, so I agreed to it. Walking back out to the dining room, Kelly announced our updated agreement which led to some mocking cheers.

"Oh butler, teased Nicole, more wine for everyone please."

As I walked back to the kitchen, I thought to myself, this has a chance to actually be fun or could be the worst most aggravating two nights of my life.

They moved from the dining room to the living room to continue talking and having fun. In a bit of fun, Nicole called me "Butler" and directed me to clean the table and do the dishes with a wink and a pat on the butt. Guess dinner was good as there was very little left on the plates or maybe it was the wine they used to wash it down. By the time they moved to the living room, four of the six wine bottles were empty.

As I finished the dishes up, the ladies were getting ready to go to bed. I went to the closet to grab a blanket and pillow for myself and threw them on the couch.

"Aww, you make your butler sleep on the couch?" Nicole teased.

"Can't treat him to well, or he won't work as hard" Kelly replied.

As Sara walked by me, she said, "Thanks for everything," and gave me a small peck on the cheek.

"Ooohhhs" rained down from the others embarrassing Sara a little bit. However, Stephanie and Kelly followed suit.

Nicole was feeling the effects of the wine a bit more and took advantage of the fact the others were already out of the room when she walked by. Being nine inches shorter meant she couldn't give me a peck on the cheek unless I bent down so she gave me a hug which lasted a while. I started to think maybe she had passed out in my arms when she finally looked up at me.

"Wish you were sleeping with me instead of Sara. Maybe when she falls asleep you can carry her out here and put her on the couch and jump in with me."

As she said this, she slid her hands down my arms while turning away, pulling on my hands to get me to bend down before turning back around and planting a kiss on my lips. Although it was just a plain kiss, the surprise and the length were a turn on which she apparently saw.

"Wow, he sure did wake up pretty fast" she said as she reached out and grabbed me through my pants. "You better calm him down before making a mess. If Sara falls asleep quickly, maybe you can join me in the shower" she said over her shoulder as she walked to the spare bedroom.

I stood there stunned. Sure, we had been playful and flirted a bit in the past but never anything close to what she had just suggested. Unfortunately, or perhaps thankfully, she fell asleep quickly leaving me with my thoughts of what could have been.

I woke up before anyone else the next morning and started my duties for the day. I reset the table and began getting breakfast ready. The girls had a spa day planned before going to get their costumes. What they didn't know is that I had a big surprise waiting for them. I was supposed to chauffeur them around and sit in the car all day waiting for them. That wasn't going to happen. There were too many college games on TV, and I wasn't going to miss them. Being the loving husband I am, I rented a limo for the day to take them wherever they wanted to go. I would pretend to get ready to drive them around and surprise them with the limo instead. If that didn't earn me some extra points from Kelly, nothing would.

Sara was the first one out, dressed in running shorts and a tank top. I offered her a glass of juice and she politely declined. She handed me a water bottle to fill up while she tied her shoes. She was going to go for a run before everyone else got up. I filled the bottle and handed it to her as I opened the door. As she walked out, I couldn't help but watch her ass in the skimpy running shorts. What I wouldn't give to pull those off her when she returned, bend her over the bed and take her from behind while pulling on her long ponytail. How this woman was not seeing someone was beyond me. Guys should be lined up trying every line and trick in the book for the chance to win her affections. If I was 12-13 years younger and single, I would definitely give her the opportunity to turn me down. Out of all Kelly's friends, she is the one I wanted the most.

I went back into the kitchen and cut up fruit and got the blender ready in case anyone wanted a smoothie. Made coffee and poured apple and orange juice into separate carafes. Just as I sat down to watch some College Gameday, Kelly and Stephanie emerged from the bedroom.

"Daaaaammmmmnnn, I need to come over here more often if this is how you get treated. My husband can barely make Eggo waffles."

"Are Nicole and Sara up?" Kelly asked.

"Sara is. She is already out on a run," I responded.

This information earned a groan from both of them. Kelly bemoaning about their lost youthful exuberance and Stephanie agreeing while downing a glass of apple juice. They made me shake my head. Both were barely in their mid-30's so it wasn't like they were old hags. After finishing the apple juice, Kelly grabbed Stephanie's hand as they walked to the guest bedroom. According to the shriek coming out of the room, they ripped the covers off a still sleeping Nicole.

About the time Sara got back from her run, the others were coming out of the bedroom for breakfast. Sara asked if she could shower before eating to which the others agreed. She kicked off her shoes at the door and moved the hair stuck to her head with perspiration to the side. She handed me the water bottle to wash later. As she was about to walk into the bedroom, I called out,

"If you need anything let me know and I will bring it."

I thought that was just being polite, but the girls felt it was a bit more than that.

"My goodness keep it in your pants until at least she's had breakfast" Nicole teased.

"Seriously" added Stephanie.

"How kind of you to make such a nice offer just to try and sneak a peek of her in the shower" added Kelly.

"That's not what I meant or was trying to do!" I exclaimed.

"Relax, said Kelly. We're just messing around with you. I would be more worried if you didn't try and sneak a peek. I've seen her in the shower at the gym and it is a beautiful sight."

The others nodded in agreement discussing how if they were lesbians, she would be at the top of their respective lists to try and get with. Well, the top of Kelly and Nicole's lists, in a bit of a shock to everyone, Stephanie let it be known that Kelly was at the top of hers. As the day wore on, that wouldn't be the only revelation to come out.

After breakfast it was a whirlwind of activity between the four of them. We only had two bathrooms, so four women trying to get ready in two bathrooms made for some Three Stooges type hilarity. Clothes being tossed around, requests to borrow this and that, cries about forgotten items left at home. I stood in the middle of the house waiting to help in any way I could.

I got the call from the chauffeur right at 11 letting me know he was waiting outside. I made sure the curtains looking out to the road were closed to keep the surprise exactly that. When they were finally ready to go, I made a big production about how I didn't think it was fair that I had to stay with them all day and miss the games.

Kelly made a pouting face and fake cried before saying; "Maybe next time you won't think you know so much about everything in the world and make a stupid bet."

"Well maybe I will find someone else to drive you all around so I can relax," I said as I opened the door.

Kelly was the first one to see the limo.

"What is that doing here?"

"I found someone else to take you guys around today."

"Really?!"

"You can't be serious, Oh my God!" and many other squeals of excitement sounded as they realized it was not a joke and really for them.

The chauffeur opened the door, and everyone but Kelly jumped in. As they were getting settled, Kelly looked me in the eye and smiled with a little tear in her eye.

"This is too much," she whispered while giving me a hug.

"You deserve it," I replied, don't worry about it and have fun."