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.
As she lifted herself out of the water, my mouth dropped open and I took in the sexiest vision I had ever seen. What Maddie didn’t realize was that her white bikini top was quite see through when it got wet. I could clearly make out the shape and color of her perfect, pink nipples that were as erect as I’d ever seen them. “That must be what everyone was staring at in the crowd,” I thought to myself. I couldn’t blame them for kissing her, she was irresistible and I would have done the same in their shoes.
“Let’s go walk over to the other pool party. Amys been texting me to join them,” Maddie said and without a word I got up and walked with her holding her hand as we walked.
“That was quite the round of kissing over there huh,” I said, breaking the silence after a little walking.
“I’m sorry, I don’t know what happened. They just started kissing me, one of them that wasn’t even at the game. It just escalated so fast and I couldn’t control myself or them,” Maddie said, sounding a little guilty. “I hope you’re not mad at me.”
“Mad? No. A little jealous? Maybe yeah, but so turned on at the same time. The way those guys looked at you was so hot. I could tell they all wanted you so badly,” I replied to her enthusiastically.
“Wow, ok,” Maddie said surprised.
“Remember our deal, I promised to stop it anytime if I’m not ok with something and I didn’t try to stop you so we’re good.” I said reassuringly. “It took everything I had not to jump in and take my own turn to kiss you and pull off your bikini and fuck you right
there in front of everyone.”
“Oh god, that sounds incredible,” Maddie said, turning to meet my gaze. “Though that’s going a lot farther than flirting with guys and making out,” she added.
“Yeah, true, I guess I just got a little carried away there for a second,” I said. We both laughed it off and kept walking towards the pool and as we were walking, I noticed every person, man or woman, stole a glance at her tits through her bikini which was slowly drying off and becoming less transparent.
It was almost dark as we got to the pool and by this time both of our suits were dried off. With it being 9 PM you would expect the tequila bar which was right beside the pool party to be in full gear by this point, but it seemed relatively empty. We almost immediately saw Jason, who looked like he just got out of the pool and went over to join him.
“Hey guys, glad you could join us. I’m glad we haven’t scared you guys off yet,” he said, reaching over for his towel to dry his face.
“No! We’re so glad we met you, you guys are the coolest couple we’ve met on vacation,” Maddie replied, equaling his sincerity and going in for a hug.
After she stepped back from their hug Jason’s eyes dropped from her face to her tits that were once again wet from being pressed to his chest. We talked for a while and recounted the party at the other pool and what it was like until Maddie asked “so, where’s Amy?”
“She’s over there in the pool talking to Roger,” Jason said.
“I’m going to go say hi, be back in a little bit,” Maddie said, before giving me a kiss and turning to join them in the pool.
Maddie waded through the crowded, waist high water on her way to Amy when she was backed into causing her to fall fully into the water. The person apologized and she continued on her way until coming up behind Amy.
“You made it!” Amy said, sounding as drunk as Maddie felt. The two bikini clad women hugged tightly and turned to each other and shared a quick kiss. Roger stood a few feet away with a grin on his face as the two girls shared a sensual moment. As they broke their embrace Roger slid in to give Maddie a hug himself, lingering longer than normal.
While hanging out in the water the girls recounted the events of this morning with the starter at the golf course which piqued Roger’s interest. “Maddie, I didn’t think you had it in you,” he said excitedly.
“This one’s fully of surprises. We made a good team today, didn’t we Maddie?” Amy said turning to Maddie.
“We sure did,” Maddie answered.
Roger, then turned towards Maddie and got his first good look at her in this bikini said “Maddie that bikini is the sexiest thing I’ve seen all week.”
Maddie smiled at the compliment. “Thanks Roger, you look good too. You’re filling out that speedo very well,” Maddie said as she let her eyes drop to the top of the water and landed on Roger’s crotch. She was originally just playing along but when she caught a glimpse of the size of the bulge in his speedo, she became desperate to find out if he was hard or if he was just really thick. She was lost in thoughts of discovering what was behind the speedo. She pictured herself reaching into his tight suit, wrapping her fingers around it and pulling it out. She started to picture how big and full of cum his balls were as her mouth started to moisten and she bit her bottom lip. Roger and Amy noticed this and saw her nipples firm up through the bikini showing how incredibly turned on she was.
Amy sensed the whole party had taken a turn early today and there were couples making out and touching each other all around them. She followed suit and waded over to Roger and started rubbing the front of his speedo along his length before reaching in and pulling out Roger’s cock. She started to stroke it, pointing it in Maddie’s direction and looking back towards her.
Maddie mouthed “oh my god,” but no sound came out as she was fixated on the huge member that Amy is stroking for her to see. She couldn’t tell if she was inching closer or if they were but the distance was being closed until she was less than a foot away, close enough to easily reach out and grasp it. In her trance like state her arm was slowly starting to reach out of the water to grasp it when Amy broke the silence.
“I have an idea, follow me.” Amy said, letting go of Roger’s cock. She grabbed Maddie’s hand, fully snapping her out of her gaze. She led Maddie through the crowd toward a bathroom, stopping just before they walked in to beckon Roger to join them. They had a quick look around to make sure it was empty and walked into the more spacious disabled stall. Amy pushed Maddie against the wall and pushed her body against Maddie as they Passionately kissed. Amy’s hands explored Maddie’s body, caressing her perky tits and grasping her ass as she pushed their mons’ together firmly. Amy abruptly broke their kiss as she heard the door open. She whispered Maddie excitedly, “just go along with my plan, you’re going to love this.”
Roger entered the bathroom and looked under the stalls and saw 2 pairs of women’s feet so he knocked on the door that Amy let him in through and locked it behind him. Roger looked at both the women and wasn’t sure what was about to happen but knew he was going to like it.
“Listen Roger, I’m going to give you what I promised the other night and since this is her first time, Maddie is going to watch while I show her how it’s done,” Amy said commandingly. With that Amy dropped to her knees and removed her bikini top and dropped it to the floor. She reached for the band of the speedo and pulled it down, unleashing Roger’s hard cock. He was about 7 inches long and about average girth but with an upward curve and a huge, thick mushroom head. Maddie’s eyes went right to his cock, she couldn’t take her eyes off it. Part of her wanted to drop down and join Amy and suck that huge mushroom head into her mouth and taste his precum. Maddie who’d recently been giving a lot of head to her husband found herself in a situation where she was now craving this man’s cock in her dripping wet mouth. Using all her will power she resisted the urge and instead slid her hand down to her bikini bottoms and placed a hand over her aching clit.
Amy slowly licked up and down Roger’s shaft before she took his head into her mouth, savoring the taste as she closed her lips around the start of his shaft. With his head now fully engulfed, she was surprised how full her mouth was. She went back up and down and back up them paused at the top before going down as far as she could take it in her throat. She stopped about an inch before the base as Roger moaned loudly. She felt Roger’s hand at the back of her head trying to force her further. She pulled back completely off his cock with a string of saliva attaching them from inches away as she kept eye contact. Maddie started to rub her clit in a long elliptical pattern as she witnessed Amy blow Roger in the steamiest scene she’d ever seen. Amy went back down and up, keeping a steady pace while gurgling his cock. Maddie picked up her pace and started to clench her toes as she felt her orgasm building. That’s when Roger, who was leaning against the wall right beside Maddie, reached over and felt her breast, squeezing it tightly as Amy pleased him. Maddie moaned as the sensation pushed her closer to cumming while she continued to rub her clit in tight circles now underneath her bottoms. Maddie was too wrapped up to care at this point, she just needs to cum and this old guy’s hands grabbing her perky tits were getting her there in a hurry.
“Oh fuck,” Maddie moaned, arching her back and tilting her head up to the ceiling.
Roger pinched and tugged at Maddie’s nipples and said “Your tits are so fuckin soft and these nipples look like they like they need some attention.”
Maddie felt his fingers pinch her nipple hard while still played with her clit, seconds away from her orgasm. She let out another moan, this time opening her eyes.
“Who are you?” Maddie said, looking at a man peeking his head over the divider from the other stall.
“Shit, ” he said, still staring at the scene frozen with fear.
As the kid was about to run, Roger released Maddie’s boob and said, “hey get back here kid. What’s your name?”
“Ethen,” the man called back.
Roger looked down at Amy who had paused her blowjob to look up and made eyes to her as if asking a question. Amy nodded a little and let go of Roger’s cock before saying “If you promise not to tell anyone you can come in here and finish watching the show.”
“O-Ok,” Ethen said and Roger reached over and unlocked the door. Ethen walked in and now the once spacious stall was quite cramped and they were all in separate corners. Maddie realized that she was still slowly working her clit and was ready to pick up where they left off. She knew she was past the point of no return and needed to cum so bad. Amy had started to continue her blowjob when Maddie noticed that the kid who looked like he couldn’t be more than 18, had the top button of his pants undone and was sporting a bulge.
“Pull it out kid I think she’ll like it,” Roger said, gesturing to Maddie.
Ethen dropped his shorts and out sprung his cock. It was fairly thin and only about 4 inches long with a sharp, pointy head. It was a sharp contrast to Roger’s above average, veiny, huge headed member. While she still had Roger in her mouth she looks over and saw Ethan’s dick. She reached over and started to stroke it while expertly focusing on Roger.
Roger went back to Maddie’s tits with one hand, pinching her nipple as he went with his other resting on Amy’s head.
Maddie looked over at the kid to see what he was doing and he stared back at her awkwardly because he has his hands to his sides. She got the feeling that he was being left out and so she reached for his hand and placed it on her other breast. He instantly began to knead and squeeze which forced Maddie to gasp as she was on the brink. That’s when she felt Ethan’s grip tighten which was all it took for Maddie to go over the edge and start to cum.
“I’m Cumming, of fuck Ethan, I’m cumming,” she said between the moaned while looking him in the eyes.
“I’m going to cum too!” Ethan announced as started to tense up, still holding Maddie’s breast.
Hearing that Amy backed off Roger’s cock and started pumping Ethan and Roger’s cocks faster, pointing them both at her tits. Ethen erupted, shooting a huge glob of cum across Amy’s nipples which made her gasp and tilt her head back so she could enjoy her cum bath. She continued jerking him and more and more jets shot out, glazing her tits.
“Oh god, I’m cumming too,” Roger yelled as he grasped his own cock and aimed it between her tits and unleashed twice the cum as that kid had. Amy’s chest and stomach were dripping with cum that formed a small puddle underneath her.
As Maddie slouched over into the corner watching Amy get bathed in cum, she saw that Amy too had been playing with herself and before she knew it Amy was having a huge orgasm herself. Both men watched, dicks still in hand as this beautiful woman moaned and flinched in pure ecstasy.
Everyone seemed to calm down over the next minute, allowing everyone catching their breath. Ethen was the first to leave, then Roger after he gave each of them a kiss. Amy went over to the sink and Maddie followed to pass her paper towels to mop up some of the cum. As Maddie approached her, she saw her slide her finger along her nipple and bring that finger to her mouth and taste the cum. After helping Amy get cleaned up, they made sure their bikinis were in place and walked out of the bathroom stealthily and rejoin their husbands in the crowd.
It was about 11 PM when the DJ came on the speaker to announce a bikini contest to a loud cheer from the crowd. The prize for winning was a voucher for half price on your next stay at the resort. I looked at Maddie and said “You have to join, I bet you’d win!”
Amy butted in “Yeah girl, you’re the hottest one out here tonight, they have no chance.”
“Ok, but I’m going to need another drink before I get on that stage,” Maddie said, reluctantly agreeing.
Everyone slammed another shot and Maddie left to sign up. She got to the stage and saw that there were about 20 other women there to sign up. “These girls are all younger, skinnier and hotter than me, I hope I don’t get eliminated right away,” Maddie thought to herself, allowing some of her past insecurities to creep in. Then she thought about how many compliments and stares she got that week and how sexy it made her feel to have those men ogle her.
The show began and all the girls came out on stage to a massive cheer from the crowd. They all took their place on stage and the DJ went by the girls one at a time asking the crowd who they thought looked best in their bikini. Maddie was the third to go and she got a loud roar from the audience. She scanned the crowd as the DJ worked his way down the line and she spotted her husband staring at her with the biggest smile she has seen since she walked down the aisle in her wedding dress.
As the DJ returned to the front having heard the reaction of the crowd to each woman he said “The top 5 contestants are: Number 8, 11, 17. 20 and 3. The rest of you sorry, but you have been eliminated.”
To Maddie’s surprise she made it to the top 5 and some of the women eliminated looked smoking hot. She felt great about herself, all the doubts she had coming in were completely erased from her mind at that moment.
“In the next round, how about we find out who looks the best all wet, shall we?” The DJ announced. Two men with hoses emerged and aimed them at the girls on stage. The water was freezing and caused all the women’s nipples to become prominently firm. Maddie threw her hands up and bounced in place, readily accepting the stream of water hitting her chest. She cheered along with the crowd while she did a little shimmy, shaking her perky tits at the crowd. She was careful not to do it too fast lest risk her nipples falling out of the skimpy suit. The whole crowd watched as all the women put on a show as they got wet. Most of their attention seemed to be on Maddie though because with the suit being wet, her nipples showed clear through the suit and she was essentially flashing the crowd. The contest went on for another minute before the DJ announced “I think we have our winner: Number 3!” The crowd erupted and Maddie leapt in the air exuberantly celebrating her win by giving the crowd another little show as they sprayed her with water before leaving the stage.
Maddie gave the DJ her name and information then she went back to join her friends. As she passed through the crowd on the way to her husband, everyone’s eyes were still on her, cheering her on and high fiving her. She finally reached her husband and leapt into his arms, giving him a huge kiss. “That was amazing! I’m glad you guys talked me into it, I feel great!” Maddie said excitedly. She slid off of me and went straight for Amy and gave her a big hug and kiss as well which she was more than happy to receive. “I know I already said it but I am so glad we met you guys,” Maddie said, still running on the high of her win. “Let’s go dance,” she said.
We all got deeper into the crowd where people were dancing and all 4 of us followed suit together. We kept it up for the half an hour on the way to midnight with Maddie on several occasions getting pulled away to dance with strangers. She felt like a celebrity, everyone wanted to say hi and see her up close to check out her body, some drunk or bold enough to try to feel for themselves as they danced with her. She would entertain them for a few seconds before coming back into our little group to try to stay close. Roger and Martina also joined in our little circle of dancing.
As the count wound down to midnight, I found Maddie and held her close, as did Amy and Jason. Midnight struck and everyone screamed happy new year. I gave Maddie a long sensual kiss that made us both disappear in the moment. We turned to the other couple and Amy caught me off guard by throwing her arms behind my head and pulling herself close to me. She drew her lips to mine and it felt amazing. We came up for air after a while and I saw Maddie doing the same with Jason. Amy slid in between them and planted an even more aggressive kiss on Maddie which she reciprocated.
I shook Jason’s hand wishing him happy new year and that’s when Martina grabbed me and pulled me in for a kiss. It was closer to making out as she slid her tongue into my mouth and I met it with enthusiasm. It lasted only seconds but it was amazing. Her body felt so good on mine and it took my attention away from Maddie for a second. We separated and I turned to Maddie to see that Roger was behind her as she made out with Amy, similar to the other night in the tequila bar. He was grinding his speedo covered crotch into her ass while tracing his hands up her side. The scene was so hot, I started to get hard and Martina noticed as she planted another kiss on me that was even sexier than before. She grabbed my hand and placed it on her breast which to my pleasure was a perfect handful. They felt even better than they looked which was saying a lot. She gasped as I kneaded her soft breast reaching out to pull the fabric to the side exposing her nipple so I could get an even better feel.
From the corner of my eye I saw Roger’s hands were now planted firmly on Maddie’s perfect tits as Amy ground her body into Maddie’s and kissing her with the same intensity I had just kissed Martina with.
Let’s jump in the pool and cool off,” Martina said, loud enough for everyone to hear. Most of us snapped out of it and headed towards the pool. All three guys sported atleast semi hard cocks, most obviously Roger in his speedo. We got into the water and Martina didn’t bother to put her top back into place. Normally she might have been out of place, but it seemed the energy around us, much like the tequila bar had turned very reckless. I looked around and there was almost as many people without tops as there was with. Women of all shape, size and age were all hanging around without a care in the world and if any of us wasn’t fully hard before, that had definitely changed. Martina took a step toward Maddie and planted a kiss on her that lasted several seconds before wishing her Happy new year.
“I hope you don’t mind but I stole a kiss from your husband and he was pretty excited,” Martina whispered into Maddie’s ear. “He’s got a nice cock.”
“Yeah, he does, I’m a lucky girl,” Maddie replied in a low voice relishing the feeling of Martina’s bare tits pressing against her chest.
After their kiss Martina announced that she had to leave to meet Juan and Roger seamlessly found another partner in the crowd, seemingly at random,
and just like that it was down to just the 4 of us. The night had turned chilly and the crowd had thinned out so Maddie suggested they all go back to our place to warm up in the hot tub.
On the way there the girls walked ahead of Jason and I just far enough so we could only hear them giggling.
“Hey we like you guys a lot and if anything starts to get out of your comfort zone tonight just give me a signal and I’ll back off. I know you guys are new to this and I just want to make sure you guys have a good time,” Jason said to me reassuringly.
“Thanks, I appreciate it, I don’t know exactly where this is heading (though I had a good idea) but I’m going to let Maddie take the lead on this,” I said.
We got to our room and went straight for the hot tub since all of us were already dressed for it. I sat between Maddie and Jason while Amy was beside Maddie. I opened the bottle of complementary champagne that came to the room this morning and gave everyone a glass. We all cheered for a great new year and sat in silence for a minute, enjoying the jets of the hot tub in our buzzed state.
“I have just the thing, do you guys smoke?” Maddie leapt up excitedly, having just remembered the weed she bought earlier.
They nodded and Maddie left to get the joint and light it. After lighting it and taking a big hit she passed to me and I did the same then passed it along to the others. When Maddie got it back, she took a hit and held it in before leaning over to Amy and blew the smoke into her waiting mouth. Their tongues met outside their mouths and they began to kiss before backing away to pass the joint around one more time before it died. Along the way Amy had taken off her top, exposing her large soft tits. We joked around and chatted as the weed started to take its effect on us, removing what little inhibitions we all had left.
“Maddie, I don’t know why you’re still wearing that top, it’s not leaving much to the imagination especially, now that it’s wet.” Jason said, smiling as he stared at Maddie’s tits that were half underwater.
Maddie looked down to see what he meant and finally she saw that her top was essentially see through when wet. “I can’t believe I went the whole day and didn’t notice! That’s probably why I won that contest and why men couldn’t keep their eyes off me today!” Maddie said with a sudden realization. “And you, Jack, I can’t believe you didn’t tell me. I bet over 200 people saw my tits today!” She added, punching me in the arm. “You’re right I might as well.” She stood up and reached behind her back and untied the strings causing the top to fall to the water.
For the first time in our relationship Maddie was topless in the company of another man and the sight caused my cock to rise. Maddie turned to me to gauge my reaction and saw my lustful expression and slid over to lean into. I felt her hand on my leg work its way up, feeling the head of my cock and sliding further up toward the base and tracing her fingers along my length. She repeated the motion a few times before Amy stood up and said, “Now that you guys can see us, I think it’s our turn for a little show.” Amy looked down, motioning for the guys to remove their trunks.
Jason stood on the bench and looked towards me, expecting me to do the same so I got up with him. We looked at the girls who had inched closer while we both showed obvious tents in our suits. The girls looked at each other and back to us and each grabbed the sides of our trunks and yanked them down, unleashing both our dicks to the cool air. We both look down at the girls who giggle as they inspected the two different cocks before them, licking their lips with anticipation of what is going to happen next. I notice that while Jason’s belly kind of hid his modest 4-inch circumcised cock, a very large, heavy set of balls hung below.
The girls backed away and stepped on the benches across the tub and together pulled down their bottoms so all of us were completely nude and out in the open air. We slid back into the tub and Amy suggested we play a game of truth or dare thinking that it would move the night’s activities along. Going first I asked Maddie truth or dare and she chose dare. I didn’t know what to pick expecting her to choose truth so I said the first thing that came to my mind “I dare you to motorboat Amy and let her Motorboat you.”
Maddie grew a big smile and slid over to Amy and pushed her tits together before squishing her face between them, lingering for a few seconds before surfacing. Amy did the same but did so while licking Maddie’s tits and even sucking her nipple into her mouth briefly causing Maddie to openly moan.
“God, that’s good,” Maddie said beneath her moan.
Amy was next and she chose truth which again was not the answer I was expecting.
“What is your biggest turn on?” Maddie asks.
“I love it when guys cum on my chest, not just my husband but anyone.” She replied with no hesitation or uncertainty.
Maddie’s mouth began to water as she sat back onto my lap the same way Amy was with Jason, still facing each other. She feels my cock get trapped between us pointing up rubbing between her ass cheeks under the water as she lightly ground into me.
Jason’s turn is next and he picked dare. Amy quickly said, ‘I dare you to kiss Maddie.”
Maddie felt my cock twitch against her ass giving her the confirmation that this would excite me even more than I already was. They both stood up and Amy sat beside me to gauge my reaction as the two met in the middle. Jason leaned in and met her lips and Maddie enthusiastically responded by throwing her hands behind his back and pressing her perfect, erect nipples into Jason’s chest. Maddie could barely clasp her hands together as frame made it more difficult than she was used to and his belly pressed into her. I saw that his fully hard cock was poking her just below her belly button and his balls swung down and slapped her mons. He reached down to feel her breast which Maddie loved. The whole time Amy was leaning into me watch my gaping mouth water as her husband enjoyed my wife. She kissed my earlobe and whispered, “they look fuckin hot together, right.”
Still frozen and taking all of it in, I didn’t respond. I was just able to nod slightly, not breaking eye contact with the sight before me.
They separated and something caught Jason’s attention behind him. With the weed now in full effect the rules of the game seemed to be blurred and Jason skipped me. He instead turned to both of the girls. “I dare both of you to run out there and kiss those guys when they walk by,” Jason suggested mischievously.
We turned to look and there were two 18-year-old looking guys in swim trunks about to walk by the pathway behind our room. Not one to back shy away from a challenge, Maddie grabbed Amy’s hand and led her out of the tub and through the grass to where the guys were walking. They didn’t see them coming because the lighting at the hot tub was pretty dim. They were very surprised when two beautiful, naked women showed up right in front of them. They were even more shocked when they both walked closer and started to kiss them Within a couple seconds of the girls attacking them, they wrapped their arms around and started to explore their bodies with one grabbing Maddie’s ass and the other caressing Amy’s tits. After about 10 seconds, the girls swapped guys and now they were each kissing the other guy. Amy seemed to really get into it as she was grinding her pelvis into the one guy’s leg as he held her tightly by her ass. Maddie was no longer kissing the other guy since he had worked his way down to her tits where he was kissing and licking furiously. They both break away and run back to the hot tub while the guys stood there confused and now fully tenting their shorts. They lingered for about a minute as we watched and the girls waved to them as they finally continued walking again.
“Those guys were pretty cute huh Maddie,” Amy said, biting her lip looking at Maddie who smiled back. “It’s our turn now,” she announced. “I dare you guys to sit on the edge and jerk your nice fat cocks for us.”
Jason and I looked at each other and stood up facing the girls and started to stroke our cocks in their direction.
“You’ve got a nice big cock Jack,” Amy said, rubbing her tits as she stared directly at my cock. She got to about a foot away while she continued on.
“And Jason you’ve got such huge balls, I bet they’re full of cum,” Maddie said looking up at Jason jerking himself while she bites her lower lip and pinches her nipple. She inched closer and closer until Jason could feel her breath on his head and held herself there. She continued looking up to him, letting her mouth stay open as his hand slid up and down his shaft half a foot away.
“I bet you guys want a show to jerk off to, don’t you boys?” Amy said sensually before leaning in to whisper something to Maddie.
Both of us continue to slowly stroke our cocks as the girls began kissing, getting steamier by the second. Amy’s hand reached underneath the water and a second later Maddie’s eyes opened wide and she moaned “Oh fuck!” Her hand continued to move in the water and Amy drifted down to put her mouth on Maddie’s nipple. She began to lick circles around her nipple and pinch the other, with her free hand as she continued to work Maddie underneath the water. Maddie was again caught in a trance as she opened her eyes and staring hungrily at the men stroking their cocks at her.
Amy stood up and took Maddie by the hand to lead her out of the tub and inside the room. We join them as they toweled off and we watched as Amy took Maddie to the king size bed. They both crawled on the one beside and Jason and I walk to the edges of the bed still slowly stroking our fully hard cocks. Amy resumed her massage as she slid her fingers up and down Maddie’s slit making a squishing noise from all the juices coming out. She paused for a second and brought her finger to her mouth and sucked on it, savoring the flavor of her juices. She dipped her finger back along Maddie’s pussy and brought it back up, this time for Maddie to taste which she hungrily accepted.
“Mm,” Maddie moaned.
As she did this I was now behind her head at the edge of the bed with Jason to her right. Amy started to move her kisses from Maddie’s mouth down her body, pausing at her breasts to suck each one before continuing further down her body. Just as Maddie felt the first flick of Amy’s tongue on her pussy she reached up and grasped my hand tightly as she writhed in pleasure. After a few seconds she settled in and accepted the immense pleasure Amy was giving her. She reached out and grabbed my cock, jerking me towards her head and placed her other hand on the back of Amy’s head, adding to the pressure on her wanting pussy. I shifted onto the bed and balance on my knees next to Maddie’s head. She got my hint and took me into her mouth letting out muffled moans while I filled her mouth with my cock. I groan in the pleasure of her mouth on me and I saw that Maddie also placed a hand on Jason’s cock and was stroking him as she sucked me. I started to thrust my hips forward, forcing my cock further and further into her mouth to about half way down my shaft. I looked up and Jason is sucking on her breast as she picked up the pace on him.
After a minute Maddie started to shake and she took my dick out of her mouth and screamed “Ohhhhh my god you’re going to make me cum Amy, don’t stop!”
Amy continued and Maddie convulsed as she came and continued to jerk us off furiously. Just as she was coming down from her orgasm. I started to get close to cumming myself which I announced with “babe keep doing that and I’m going to cum.”
Amy looked up and saw Maddie splayed out on the bed and both guys getting ready to cum as Jason had stood up and was now jerking his cock over Maddie’s body. She beckoned Jason to come behind her and he walked quickly behind her and slid into her pussy easily. He started to pound her from behind with slapping sounds coming from both his stomach hitting her ass and his gigantic balls hitting her clit as they swung with his thrusts. Soon after she announced “Fuck I’m so close to cumming I want those cocks to cum all over my tits.”
I turned to Maddie who was still stroking me while watched her friend get fucked from behind, begging for the guys to cum on her. She smiled up at me and signaled that she wanted me to do what she said.
Just then Jason burst out that he was about to cum and told Amy to get on the floor. I was pretty close myself, so I joined him with Maddie following me. With Amy on her knees pushing her tits out towards Jason, Maddie sat right next to her and reached up to keep stroking my cock. She took it in her mouth, sucking my full length a few times before pulling up and watched Jason empty his balls onto Amy’s chest with jet after jet of hot cum. Amy was rubbing her chest with one hand and her clit with the other looking up into her husband’s eyes. That’s when I announced I’m about to cum and Maddie pulled it out of her mouth and pointed my cock at Amy’s tits. She watched intently as I came hard onto her chest, continuing to milk me with her hand until the last drop was stuck on the tip of my dick. She leaned in and licked it up and smiled up at me. Amy, with cum splattered all over her tits, dripping to the floor, came to her orgasm right after, and screamed even louder than Maddie which certainly alerted the neighbors to what was going on in here.
We all collapsed onto the bed to catch our breath, taking in what just happened. It was definitely the craziest sexual experience of our life so far and I was glad we did it. Maddie cuddled up into my body under my arm and said, “I love you so much.”
“I love you too, thanks for taking this journey with me,” I replied silently, giving her a kiss on the top of her head.
After a while Amy rinsed off in our shower and hugged Maddie on her wayout saying goodbye. With only a few days left on our trip I was more than satisfied with all we had done and I felt like even if we never did anything like this again, I would die a happy man.
Be on the lookout for part 6 to follow shortly.
Comments are very welcome to help me improve and to let me know you guys like what you’re reading so far.