Slowly Opening Up On Vacation Ch 05

We got up early to meet Amy and Jason for breakfast and catch the shuttle to the golf course. Several mimosas were had each and we left just in time to catch our ride to the course. We got our rentals loaded up onto the cart and rolled up to the first tee with Jason and me in one and Maddie and Amy in the other. The starter, who had to be about 75, came up and inspected our carts and when he got to the girl's cart he shouted "hey what's this?" He lifted a bottle of schnapps out of the back of the cart, continuing "you're not allowed outside drinks on the course, I'm going to have to escort you off the property." He grabbed the bottle and headed to his hut to call the clubhouse.

"Whoa hold on, that won't be necessary, will it?" Amy called out to him then got out and followed him into the hut with Maddie in tow. The door closed behind them and only muffled voices could be heard.

Me and Jason who were already on the tee waiting to start watched the whole scene unfold, confused. The door swung open and both Maddie and Amy walked out, Amy holding the bottle and both a bit disheveled. A few seconds later the marshal came out and motioned for us to go ahead. I tried to focus but my mind was racing and both Jason and I hit terrible shots as a result. The girls teed off and we continued onto the course. After a few holes we saw that Jason and I were close in skill so we decided to make the round a little more interesting. On hole 4, while we wait to tee off, Jason proposed that the losing couple at the end of each hole must take a shot. We all agreed and we continue to play. We lost the next 2 holes because Maddie lost her ball in the water on 5 and I missed an easy putt on the next.

"Come on, beat us already, we're getting thirsty," Amy taunted as they won their third consecutive hole. "Tell you what; we'll do a shot with you guys this time because we're starting to get too sober."

We all had a shot on top of the drinks the cart girl kept bringing us. At this point I was feeling it and I needed to slow down or I might not make it to 18, let alone midnight tonight. With some luck we were able to win the next 2 holes and on hole 9 it came down to Jason having to make a putt to tie the hole. As he was about to shoot, Maddie pretended to drop something and bent over in front of him exposing her tiny thong panties to him which caused him to lose focus and miss by several feet.

"All tied up, we got 'em on the run babe," I taunted, then Maddie and I high fived.

The girls went to the bathroom together and we went to buy lunch at the club house before heading to hole 10.

"I wonder what the deal was with the starter," I said to Jason while we waited.

"He seemed kind of mad about something and I guess the girls must have talked him down. We should ask them, I'm curious myself." Jason added.

While in the bathroom Amy mentioned "that old guy just about came in his pants as soon as he got his hands on my tits. Men are easy that way, show them your titties and they melt into your palm and you get what you want. Especially when they're as

nice as yours," Amy added.

"I bet yours looked even better than mine do at my age, yours are still so plump," Maddie replied. "So, what happened with Mateo after you guys left? Sounded like you invited him back to your room," Maddie asked, with it being on her mind since they left last night.

"Ohh yeah, he came over and you would not believe the size of the cock on that man! I took turns blowing him and Jason and they both came on my tits. Jasons usually got a big load but Mateo absolutely drenched me in cum before I cleaned him up and sent him on his way," Amy said seemingly reliving her pleasure. "One of my kinks is I love it when men cum on me, it makes me feel so powerful."

"Wow, I kind of wish I was there to see that. In the hot tub I think he was jacking off next to me and when he hugged me as you guys were leaving, I could feel that huge thing against my leg," Maddie said excitedly.

"I bet the guys would have liked that. I could tell Mateo wanted to stay and see what would have happened when he almost turned down this hot body," Amy teased.

"No way! I don't think anything would have happened so he made the right call. I was pretty horny though... It's nice to have someone to talk to about this stuff with since Jack and I are so new to all of this. I really appreciated you making that excuse when I told you I needed some alone time with Jack. I could tell Jason was needing to cum soon judging by the sounds he was making," Maddie added sincerely.

"No problem, Maddie, from my experience it's important to go at your own pace and not go places until you're ready," Amy replied, pulling in Maddie for a hug. They left the bathroom to join the boys at the 10th tee box.

"Hey Maddie we're curious, what happened with the starter on the first hole?" I asked her.

"He caught us with the bottle of Schnapps and was going to kick us off the course before Amy and I convinced him to let us keep it and play," Maddie said a little embarrassed. Amy leaned in to whisper something to her.

"And how did you manage that?" I asked.

"Do you really want to know, Jack," Maddie said more confidently.

"Sure, I'm curious," I replied.

"We let that old prick grab our tits and he just about came in his pants," Maddie said blankly while staring me down. She waited a few seconds before adding "we're not above giving an old man a little show if it means we get to play."

Jason had a surprised yet proud look on his face and said "good girl." Hearing that put a huge smile on both girl's faces, like they did a good deed and should be rewarded somehow.

I stood there with my mouth gaping open. Maddie had never done anything like that in the time we've been together and I felt a weird feeling of lust towards her even though she let some old guy feel her up.

"Wow," is all I could muster at the moment. Maddie walked by me towards our cart and grabbed her sandwich and drink and returned to her cart winking on the way back, licking her lips.

"Let's up the ante gentlemen," Amy announced. "Since I know both of you guys like a good show, how about the wife of the loser between you two has to play the last 2 holes topless."

I looked to Jason and then to Maddie who looked at me confidently then I said "As long as Maddie's ok with it you're on." Maddie nodded and we had ourselves a game.

We traded wins for the first four holes with three more left to play. I started to feel the pressure but Jason seemed surprisingly relaxed, if not a bit drunk. He's definitely experienced his wife being nude in front of a bunch of people before as evidenced with how comfortable they were in our hot tub. The next two holes passed and we were once again tied with one to go, a short par three with a bunch of water surrounding it. The girls seemed to be less interested in golf than they were in just drinking and laughing.

I walked up to the tee and as I was lining up when Maddie blurted out, "the wife of the winner of this hole has to give the starter a kiss on the way out. This way we both have some fun."

With this on my mind, I didn't know what to do so I just closed my eyes and hit it. It seemed like it was going straight for the water until it landed right beside it in a terrible spot. Jason, having seen this knowing there was no way I would recover, hit a safe shot. It wasn't super close but good enough to pull off an easy win. We went down to my ball and I inspected it and decided just to go for it and I swear I hit the shot of my life and it ended up rolling into the cup for a birdie. I don't know what I had done, Maddie was going to have to kiss with that old guy, but at least she didn't have to spend the next few holes topless. As I grappled with that idea, I looked over and Jason had already hit his shot and it too was heading straight for the cup. It circled the edge and dropped, surprising us all. All of a sudden, the game was tied and nobody won.

The girls seemed disappointed that there wasn't a winner and whispered amongst themselves until they agreed on something. They both stood up, lifted their shirts off and got back in their cart and drove off to the next hole. We snapped out of it and cheered them on as they drove off. On the last green when we finished the girls hugged as well as gave us each a quick kiss on the lips which made Maddie smile when it was my turn. They both drove up to the starter's hut, still without shirts on and walked into the hut where the old guy was.

"Hey, surprised to see us again?" Amy said to him in a sexy voice. As soon as he saw the two scantily clad women his pants tented. Amy leaned into him and kissed lustfully for a few seconds before backing away and letting Maddie have her turn. She kissed him, allowing his tongue to explore her mouth a bit. Unbeknownst to her, Amy was rubbing the front of his pants until his body started to jerk and the girls backed away knowing what they had done to him.

The girls walked out quicker than last time but with just as big of smiles. The guys laughed when they returned and the girls finally put their shirts back on. The shuttle to the resort came shortly then we parted ways with plans to see them at some point later that evening.

On the way to the room, we passed by numerous large parties going on at the resort that, at 3 PM, seemed to be in full swing. We went to the room to get changed and I threw on my trunks while Maddie was taking her time putting on her bikini in the bathroom.

"I have a surprise for you," she called before stepping out of the bathroom in white bikini that made her body look heavenly. It covered even less than the yellow one with a cut-out at the bottom to show some sexy underboob that left little to the imagination. The material also seemed quite thin like the green one and I swear I could almost make out her nipple from behind the fabric.

"You've never looked sexier, babe," I said to her with a hungry grin.

Maddie smiled and said, "Thanks babe, this was the one Josie meant when she said she got a sexy one for her birthday." She did a couple poses for me to show off then we left the room to go find something to eat and check out those parties.

On the way to the party closest to the entrance I noticed Maddie had gotten what seemed like the 40th text of the day so I asked her, "Hey who's been texting you all day? Your phones been ringing non stop."

"Oh, that's Todd and Roger, they've both been texting me asking where I'm going to be today," Maddie replied. "I told them I would let them know when we get settled."

Not realizing she had given out her number to them I just said, "fair enough."

After eating a late lunch, we went to the beach to get a little sun. We were just arriving at the beach when a seedy looking guy with a backpack approached us and asked, "Do you guys looking to party tonight?"

"This must be the guy Amanda was talking about," Maddie said excitedly. "Yes, please we'll take some weed." He pulled out 2 joints and hands them to me and Maddie paid the man a 20 and he took off. "We'll save it for later tonight," She added.

We stayed for a bit to relax before walking towards the nearest party to check it out. As soon as we walked into the area, we figured that there must have been almost 200 people there. Most of them we didn't recognize, so we guessed they probably came from other resorts. The scene resembled something of a rave with most of the older crowd sticking to the outskirts and the younger people in the center dancing and being rowdy. We grabbed a drink which was a special punch they made for the party that contained several types of alcohol in it. The pool was fairly crowded but still enough space to hang out in if you wanted and there were tables set up for drinking games in full swing.

We hadn't seen anyone we knew yet and since Maddie and I used to be unstoppable at flip cup we joined a bunch of random people at a table. Everyone at the table seemed to be in their early 20s except for us which was our first hint that we might have been in over our heads. They announced the rules which hadn't changed: one after another every player takes their drink and flips the cup to land upside down and so on until the last person in line completes this. We lost the first game and found out that the punishment for losing was that we had to do a shot. Being the competitive people that we are, we took the shot and stuck around to try to win. We lost the second one as well and took another shot.

Some people left and we waited until there was an even number of people to play and who showed up but Todd and two of his friends (I later found out Maddie texted him to join us). Somehow, Maddie and I got put on separate teams, me at the end of one line and Todd at the other so the game would hinge on one of us beating the other. He was already pretty drunk looking so I liked my chances. The first game was tied until it got to me and Todd and I got the cup to flip on my first try while he was still fumbling with his. They were forced to take a shot which Todd and his friends down along with Maddie who they all made sure to cheer with and high five after. We played again and I once again got it on the first try which made me feel good. Todd cursed loudly and looked a bit frustrated before taking the shot with Maddie and his friends.

"Why don't we change the teams up a bit?" Maddie suggested. Looking Todd intently in the eyes, she added, "I'll swap for your friend, and why don't we up the stakes a bit."

"I'm listening," Todd replied with a bit of a slur.

"You see I want to go to the spa with my husband on Monday and you have the other pass. If we win, we get your pass but if you win, I'll make it worth your while."

Before I had a chance to veto the proposal Todd blurted out "is that so? What's in it for me?"

"How about a kiss?" Maddie said biting her lip and placing a hand on his arm.

"You're on," Todd answered excitedly.

They shook hands and Maddie switched places with Todd's friend. The game started and someone at the start of our line couldn't get their cup to flip so we were several seconds behind when it came to Maddie. She expertly took her drink and flipped the cup on the first try, intent on winning; now it was all up to me. As I shot my drink back, I looked up to see that Todd was already attempting to flip his cup. I put my cup down and was about to make an attempt when I saw his cup land upside down and with that the game was over. Maddie and I grabbed our shot and cheered and downed it, hitting Maddie right away and making her instantly dizzy. Looking a bit out of sorts she told me she needed some water.

We started to walk over to the nearest drink hut to get a bottle of water to help her clear her head when she turned to Todd and his friends and said "we'll be right back, I just need some water. We'll find you in a few minutes and you can claim your reward."

The guys stared as we walked to get some water and had a seat at a table by the edge of the pool. We sat there for a good 15 minutes and just did a little people watching while Maddie recovered. A man walking by giving out steak and vegetable skewers walked by and I snagged a couple for us. We ate them quickly and Maddie said "I needed that, I feel much better."

"That's good, one of the good things about this climate is it doesn't take long to sober up with all the sweating in this heat."

"That's true, it's really hot today. That's probably why there's so many people in the pool right now," Maddie said. She was right, there were so many people in the pool, there was barely a foot between groups of people, save for the deep section right in front of our table.

"Todds in the pool across the way, waving me over. Might as well get this over with," she said, standing up. She turned to me and said "be right back babe."

She started to walk to go around to the other side of the pool but paused for a second to think before turning towards the pool and gracefully dove in. She adjusted her top as she surfaced and swam the short distance to the ramp of the shallow end. She walked another six feet toward the boys who were standing in a tight semi circle due to the crowd. Todd and his friends stared intently at her chest as she approached them, a look of lust filled their eyes. I was probably 40 feet away and I was close enough to be able to see them drooling over her but not close enough to hear what was said.

"A bet is a bet, so take your prize," Maddie said smiling at Todd. She started to close her eyes and lean in when she was grabbed by the hips and turned toward the friend at Todd's left and he pulled her in and kissed her lips. She kissed him back a little but pulled away quickly as she hadn't expected that. She looked at him surprised while he met her stare then he broke it to look straight down to check out her body. The shameless younger man checking her out made Maddie feel strangely good. Before she had a chance to process any of her thoughts, she was pulled to face the guy at the end and he stepped forward to meet her.

"I'm next," he said in a low growl, before planting a kiss on Maddie's partly open mouth. Their lips met and he pulled her close with his hands on her lower back just below the water. He slipped his tongue into her mouth which she didn't immediately meet with her own. She felt another hand on the back of her thigh that slid up and grabbed her left cheek. She let out a little whimper and extended her tongue to gently lick the young man's. This went on for a few seconds before she felt another hand on her other cheek. The guys had closed the circle and were now surrounding her. She spun once again, this time toward the friend who hadn't played the game earlier. He pulled her in for a kiss and explored her mouth aggressively which Maddie tried to calm but to no avail as he was licking all around the inside of her mouth. Meanwhile there are several hands on her ass and hips, dangerously close to the front of her tiny bikini. She could feel the guy behind her grind into her ass with his crotch which she involuntarily pushed back against. She felt him swelling as it slid along the top of her ass. The sensation was interrupted when she was turned to face Todd.

They paused for a second before Todd pulled her to him and began to kiss her sensually. She was much more receptive to this his kiss and let him kiss her for longer than the 3 seconds she gave the others. She could feel the tent in his trunks poke her just below her belly button and judging by how far away their bodies were separated, he was on the bigger side. As they continued to kiss Todd reached in the water to adjust his cock from outside his suit to point it down towards her feet. As he slid it down, she felt the tip run along her mons before rubbing against her clit briefly causing her body to jolt forward and a shock of pleasure to run through her whole body. With it pointing down towards her feet she was pulled in closer with both his hands resting on her ass and her barely covered tits pressed against his chest. He squeezed her ass roughly which she loved and responded by kissing him harder. As she did this, she felt his thick member spring up between her legs with the top side of his head resting along her pussy lips. While this was happening, she felt another dick against her ass but this one short and thin feeling as it squeezed in between her butt cheeks. Todd started to thrust his hips which caused his head to slide along the thin fabric covering her clit and as it did, she met his thrust with her own causing him to shudder in her mouth. This caused the guy behind her to slide his dick upward between the top of her ass cheeks.

After the longest 10 second kiss ever, she broke away from them and walked backward toward the deep end. As she backed up, she noticed behind the guys that a crowd had formed to watch her kiss those guys and they all seemed to be looking at her chest. She said "see you later boys," before turning and swimming back to the edge of the pool by the table I was sitting at.