Happy to Help! Ch. 03

Welcome to another one of my stories! My ex-girlfriend said I should share some of these crazy stories with the world. At the time, I never bothered but now with the pandemic I have a lot more time on my hands, so...enjoy! I have changed the names to protect everyones privacy, but the rest of the story is 90% true and 10% filling in the blanks of minor details that I don't remember.

So, depending on where you are joining us from, this story is either the continuation of chapter two from "Happy to Help!", where we met up two weeks later with the fun group of Laura, Brynn and their friends, or it is the continuation from chapter two of "Bowlarama", where Jenny and I had tons of fun in a cabin near the mountains and then Laura, Brynn and the group joined us the following night.

So this story begins around lunchtime on Saturday. Jenny and I awoke that day, had some pretty decent morning sex, took a shower, and hung out for a bit. I got a text from Laura that the group was running about a little late, and would be arriving around 3pm at this point. So, Jenny and I had lunch, and then we got dressed and went for a hike (and by hike, I mean we walked down the trail area immediately surrounding the cluster of cabins). It was kind of a bummer to go get her bag with her clothes in it and have her get dressed, but we wanted to see the trails and decided it was probably safest for her not to be naked.

After we got back to the cabin, Jenny kept herself busy getting the bar set up and getting dinner ready so that we could just throw things on the grill when the time came. I made sure the hot tub was ready. In addition to a bigger living room, cabin #2 also had a bigger hot tub. It had a killer view so I figured it would probably get some use. I took the cover off and it was ready to roll!

Around this time, Brynn called and said they were running even a little bit later due to traffic. She asked if I had the cards ready, I told her I did. If you're wondering what she meant by "have the cards ready", well...I had messaged with Brynn a little to set the plan for the weekend and she gave me instructions for the blackjack game. Brynn said she had talked to some of the other girls and they all wanted me to fix the game so that Laura lost first. I told her that was fine, but that Jenny also wanted to lose and I was sure Alyssa would too. Basically, we all wanted Jenny, Laura, and Alyssa to lose early. None of the girls cared much if any of the men lost. The rest of the ladies (Brynn, Emily, Beth, Megan and Kristin) wanted to join in the fun but didn't want to be naked early in the game.

So my idea was to just to deal off the bottom of the deck, where I would have all the face cards (worth "ten" in blackjack) ready. I would get six or eight decks ready, similar to how Casinos deal blackjack, that way I didn't have to re-stack in the middle of the game. Not that I thought anyone would be particularly upset, I just wanted it to look fair. So I told Brynn how it would work. Saying "hit me" would get a face card from the bottom and probably put the person over 21, anything other than "hit me" would get a regular card. Basically, saying "hit me" means you will bust out and have to strip. Presumably we would have someone "bust out" on every hand (literally and figuratively, ha!) so it didn't matter a ton what anyone had except the girls who said "hit me". She loved this idea, since it meant she and the other girls could control how quickly their clothes came off. Except of course for Laura, Jenny and Alyssa. For those three ladies I would just deal them face cards every time and get them naked as quickly as possible.

Jenny had a pretty impressive bar set up, the hot tub was ready, the cards were ready...now we just needed for everyone to arrive. Jenny and I went back to our room, and took a shower. It was fun to help her pick out her clothes.

"Just think...everything you're picking out to put on now, you will be taking it off later, in front of everyone." I said.

She blushed.

"How do you know, mister? Maybe I'll win that blackjack game!" she said.

"I like my odds. But, I'm happy to make a side bet..." I said.

"Oh?" she asked. '

"That's right." I said.

"I'm game!" she said.

I reminded her that she still owed me one, from chapter one of "Bowlarama!". The "one" that she owed me will definitely end up in a story at some point, but hey, why not shoot for another?

"Ok, how about this...if you end up naked before me, I get to pick an entire evening's worth of activities, and you have to do it, no matter what I pick!" I said.

"Ok! And if I win, same!" she said.

Of course, I was going to win. And she knew that. I'm not sure if she knew what activity I was going to pick out but it will soon become chapter four of "Happy to Help!".

With Jenny dressed, I looked at my phone and saw a text from Laura that the caravan of cars was finally nearing the cabin. We would soon be underway! Jenny and I went downstairs and before we knew it, cars were pulling into the driveway.

Laura, Brynn, Beth, Emily and John were in one car that John drove. Jim drove the second car that had Alyssa, Megan and Kristin. I realized as Laura got out of the car that I hadn't seen her with clothes on in several months. She ran over and gave me a hug.

"Hey there! You look great! But you know, I barely recognize you with clothes on!" I said.

She laughed, and blushed. I introduced her to Jenny and they hit it off right away. I was pretty relieved. The girls all headed inside while John, Jim and I started taking loads of suitcases in for the ladies. It was about 4:30pm, so it was a great time to start drinking!

Ok, so we have some new characters here and I should tell you a little more about them before we get any further. Megan and Kristin we met in chapter two, but they played a pretty minor role so I didn't tell you much about them. Well, in this chapter they do a little more so let's hear about them. Megan and Kristin were friends of Laura and Brynn's and I suspected that they were a couple but it wasn't easy to tell. They shared a room that had one bed, but that doesn't really mean anything with women. Megan was a slightly less hot version of Laura. They could have been sisters, except Laura would have been "the hot one". Still, she was totally hot, with shiny blonde hair, a nice body and a great pair of what looked like about C-cups. Kristin was a little bit curvier, but still had a great body. She had brown hair and a pretty face. We met Jim and Alyssa in chapter three of "She Sure Showed Us!" but since then she had died her dirty blonde hair to jet black. It looked hot! Apparently she and Jim still lived at the gym, since she still had her hot little yoga body. Emily and Beth were super cute. Emily had her boyfriend John with her, but Beth was flying solo. Emily was a sexy brunette who had a medium build, very toned and sexy though. Beth was a skinny girl with a perky pair of what looked to be B cups, and had died her hair with purple highlights that looked super cool. All in all, this was a fantastic group of beautiful ladies!

I gave everyone a little while to get settled, and then started rounding people up with a few bottles of champagne for a toast. The sun turned the sky some really pretty colors, and I popped a few corks. Everyone gathered on the porch, and we had a toast. This was a really fun bunch. We chatted and mingled for a bit, enjoying the champagne, and I started getting the grill ready. There was a funny tension in the air. We all knew what we were eventually going to do, but nobody knew when we were going to start doing it. I figured that the game would be best enjoyed by everyone after sundown so played it cool, poured plenty of drinks and eventually started throwing burgers and things on the BBQ. I managed to have a quick chat with Jim, and mentioned to him that were totally fixing the game. He thought it was pretty hilarious and said it was a great idea. I told him the system, and said it was his call if he wanted to tell Alyssa the system, or if he wanted me to deal her right out of her clothes. He said to go ahead and deal her from the bottom of the deck so that she ended up naked at the same time as Laura and Jenny. Apparently she had really wanted to be in the first game of strip foosball at the party from chapter three of "She Sure Showed Us!" and was specifically looking forward to this evening to show off a little bit. I told him not to worry and that I'd deal Alyssa nothing but face cards.

Nobody ate much, but everyone ate some and drank plenty. Before we knew it, the sun started dipping below the horizon. I mentioned my idea about starting the game as the sun set to Brynn, and said that we should just head in when it did, and everyone would probably follow. She agreed. Once the sun had fully dipped, Brynn and I looked at each other and nodded. We headed inside and sat around the coffee table and sure enough, the group gradually started following us. Soon enough, we were all seated around the coffee table.

If you read chapter two of "Bowlarama", you remember that I had re-arranged the furniture in the cabin to seat a larger group around a huge coffee table. I had three chairs set up on one of the long sides of the coffee table that were intended for Jenny, Laura and Alyssa (our guests of honor). As the dealer, I sat in the middle of the couch across from them. As everyone sat down around the table, I had a little fun thinking back to the previous evening when Jenny laid out on the coffee table naked and played with her pussy while I watched.

Beth, Brynn and I shared a loveseat facing the three chairs I had set aside for Laura, Jenny, and Alyssa. Megan and Kristin sat together on a loveseat on one side of the table, to my right. Jim, Emily and John sat across from them on a sofa to my left. Laura, Jenny and Alyssa figured out the three chairs were for them. It was kind of funny, in that we all knew what we were going to do and we all knew that the three of them were going to lose much faster than anyone else. We even went so far as to make sure they had the best seats! But we didn't talk about it. Part of the fun was pretending like the game was totally fair and not rigged in any way so that the girls could pretend like they were trying to win. And, it was time for the fun to begin!

"Ladies and gentlemen, the game is strip blackjack!" I said.

There were some "ooh's" and "ah's" from the group.

"The rules are very simple. Face cards count as ten and aces can be one or eleven at players choice. If you go over 21, you have to remove one article of clothing. If nobody goes over 21 in a hand, then the lowest hand removes one article of clothing. If we have more than one person go over 21 in a hand, they all have to strip one article of clothing. Jewelry and shoes do not count. Any questions?" I said.

"Let's get it on!" Jenny said, and the group cheered.

There was a little bit of trash talk as I dealt the first hand. Everyone was very excited.

I started to my left, and asked Beth if she would like a card. She was showing a 7.

"I'll take a card." she said, with a wink.

She knew the system we were using.

I dealt her a 4, and she said she would stay.

Jim, Emily, and John were next. They each took a card, and held without going over. Then the real fun began, as I got to Laura, Jenny and Alyssa.

"Hit me!" Laura said.

Laura was showing an 8. Brynn smirked, as I reached under the deck and dealt a king to Laura. Everyone cheered, and Laura blushed. She didn't flip over her card yet, but, the look on her face said it was higher than a 3.

Next up was Jenny, showing a 4. Of course she wanted a card, and I gave her another 4 from the top of the deck.

"Hit me!" Jenny said, giving me a sly wink.

I pulled a jack from the bottom of the deck, and laid it right next to her 4's. Everyone cheered as Jenny blushed.

"I'll stay." she said.

"Stay clothed? No you wont!" Laura said, and everyone laughed.

Alyssa was showing a 9. This would be easy. She asked for a card, and I pulled a queen right off the bottom. Her jaw dropped, and everyone cheered. She blushed, and said she would stay.

Megan, Kristin and Brynn each said they would stay. I suppose after the three girls had obviously gone over 21, there was no need to risk things by taking a card.

"Okay, let's see everyones's cards!" I said.

Everyone except Laura, Jenny, and Alyssa flipped their cards right over. Nobody had a spectacular hand, but the eyes all turned to the three girls who were showing face cards. Laura went first. In addition to her 8 and her king, she had a 5, for a total of 23.

"Uh oh...looks like we have our first loser!" Brynn said.

Knowing the dynamic of her and Laura's relationship, I knew that Brynn saying that turned Laura on. She smiled, giggled, and the group started a chant of "take it off!". As the dealer, it was up to me to inform her that she lost.

"Laura, your 23 means you have to remove an article of clothing." I said.

She smiled, blushed, and pulled her tank top over her head. She had on a black bra that matched her tank top. It showed some pretty epic cleavage, and everyone paused for a minute to look at her. She folded her tank top and laid it on the ground behind her chair. Then she looked at Jenny, and so did the rest of us. Jenny was showing two 4's and a jack, and she flipped over a 6. She had 24.

"Jenny, your 24 means that you have to remove an article of clothing." I said.

She winked at me.

"Oh no!" she said. I almost believed that she meant it. She smiled, blushed, and pulled her t-shirt over her head while everyone chanted for her to take it off. She had on a white bra, with a little bit of lace. Just like Laura, she had some pretty epic cleavage on display. She tossed her t-shirt aside, and looked at Alyssa. Alyssa was a funny one. She just shrugged her shoulders and took off her shirt without flipping her cards over. If you remember from the third chapter of "Happy to Help", Alyssa was super cute with great, perky tits that looked great but were maybe a size or two smaller than Laura and Jenny. She smiled at me, clearly not wanting to flip her card over.

I collected everyone's cards, and dealt again.

The first hand somewhat repeated itself. Nobody took much of a risk, until I got to Laura. She was showing a 3, and asked for a card. I gave her a 6 off the top and she asked for another card. I dealt her a queen right off the bottom and everyone cheered. She turned a deep shade of red and said that she would stay.

Jenny was up next, and was showing a 9. She looked just a tad bit nervous (totally an act) and said she would take a card. I dropped a jack. Her jaw dropped, and everyone laughed.

Alyssa was up next. She was showing a 3, and asked for a card. It looked like she held her breath as I pulled a 4 off the top. She thought it over for a minute and asked for a card, and I dealt her a king off the bottom. She tossed her head back with a big laugh, as everyone cheered. Nobody else took a card.

"Ok everyone, let's see your cards and see who has to strip for us!" I said.

Everyone flipped their cards over. As I expected, nobody was even close to 21, except for Laura, Jenny and Alyssa, who were all well over.

"Uh oh!" Brynn said.

We all laughed.

"Well, ladies, I think you know what time it is. That will cost you one article each." I said, with a grin.

Laura, Jenny, and Alyssa stood up and started fumbling and unbuttoning their clothes. Laura and Alyssa had on shorts, and Jenny had on a miniskirt. They all looked at each other to see when they were ready, and then they all three pulled down their shorts (or skirt) at the same time. Alyssa and Jenny had on sexy little "boy-short" panties, and Laura had on a thong. They all stood in front of us, grinning and blushing in just their bras and panties.

"Excuse me, Mr Dealer? I think we should institute a rule that each time you strip, you have to turn in a circle for the group. I, for one, really want to see those sexy butts!" Brynn said.

"I think that sounds like an excellent rule! I will put it to a vote. All in favor?" I said.

Everyone raised their hands, except for the three girls standing up in just their bras and panties. They just grinned.

"Well, ladies, the group has spoken. Let's see one full circle each." I said.

First Laura did her turn, showing us her perfect little butt. Then Jenny, then Alyssa. Each girl blushed and grinned as she turned her circle, then sat down.

The next hand was just like the first two. I started to my left again, and Beth, Jim, Emily and John each took a card but looked well under 21. There wasn't any real excitement until we got to Laura, Jenny, and Alyssa.

"Careful ladies, you don't have much left to lose!" Brynn said.

She really was fantastic at the smack talk. The girls just blushed.

Laura was showing a 7. She asked for a card nervously, and I flipped a Jack out from under the deck. She squirmed, blushed and laughed as everyone cheered. I decided to play around a little bit with the rules.

"Ok Laura...you're going to have to either show us your cards or show us your tits." I said.

It wasn't exactly the rules of the game but nobody seemed to mind, and Laura didn't argue. She flipped over a 7.

"Uh oh...let's see them!" Brynn said.

Laura reached behind her back for her bra strap. She unhooked her bra, and the entire world seemed to stand still for a minute as her bra fell off and her tits came into view. Her nipples hardened pretty quickly as the entire group stared. I noticed that even Jenny was staring.

"Aren't you forgetting something?" Brynn said, as she motioned her finger in a circle.

Laura stood up, obediently, and turned in a circle for us. She sat back down, in just her thong, and folded her arms in front of her boobs.

"Oh no you don't! No covering up!" Brynn said.

It wasn't a rule we set in the beginning, but I decided to allow it. Brynn instructed Laura to sit with her hands either in her lap or at her side. She did as she was told, and I noticed Laura and Brynn shared a wink as Laura sat in just her thong with everyone's eyes on her.

Not wanting to let Laura have all the fun, Jenny asked for a card. She was showing a king, and I dealt her a queen right off the bottom. She dropped her jaw, again, and laughed as everyone cheered and then began the "take it off" chant.

"You know the rules Jenny...let's see that card or see those tits." I said.

She flipped over her card, and it was a 5. She grinned as she stood up, and reached around her back. She unsnapped her bra, and let it fall into her hands. She tossed it aside as everyone stared. She gave her boobs a little squeeze and her nipples hardened for us. Everyone stared, including Laura, and she clearly enjoyed her moment in the spotlight. She winked at me, and I winked back.

Alyssa had been waiting her turn patiently, with a 5 showing. She asked for a card, and I accidentally dealt her off the top. I guess I was distracted by all of the fantastic boobs on display. I dealt her a 3, and she asked for another card. At this point, she was barely pretending to try to win but nobody was complaining. I dealt her a queen, and everyone cheered. She stood up, and unclasped her bra from the front. She grabbed one side of it, and twirled it above her head like a stripper. Everyone cheered and whistled as she spun in a circle, and tossed her bra at her boyfriend Jim. He caught it, and wore it around his neck like a towel. Her nipples were rock hard, just like Laura and Jenny. The three of them sat in a row, with their boobs out & huge smiles on their faces, loving every second of the attention.

Moving to the right, Megan surprised me and was the first of the girls who were in on the game to say "hit me" and request a face card. I raised my eyebrows at her, as if to make sure she knew what she was asking for, and she winked at me. I reached under the deck and dealt her a Jack.