Fun in the Sun! Ch. 02

Welcome to one of my stories! My ex-girlfriend said I should share some of these crazy stories from my younger, crazier days with the world. At the time, I never bothered to write things down 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.

If you read the first chapter of this story, you met my ex-girlfriend Courtney and got to follow us on a weekend to a fun & sexy tropical resort with a clothing optional pool area. We had some fun, and met some new friends (who we will call Bill & Kristin) and most importantly, Courtney got a little bit more adventurous as the afternoon went on. Our original plan for the weekend (just a quick escape from a particularly cold winter/spring in the northeast where we lived) was to start slowly. Courtney originally said she would probably go topless, and I bought her an especially naughty bikini to wear that weekend. Before we even made it to the pool area she had changed from her regular bikini into her new skimpy one, and she ended up spending at least 2/3 of the afternoon completely naked. She even made a naked trip to the poolside bar where she met Bill and Kristin!

Courtney was a big hit at the pool area. She had a smoking hot body - somewhere I still have a picture of her in that skimpy bikini and I wish I could find it! It was so funny to see her acting like that around the resort because back home she was very modest in her attire. When she and Kristin walked around the pool naked in the first chapter, people practically tripped over themselves to get a better view. She really came out of her shell that first day!

The first chapter ended with Courtney and I passing out after a quickie. Between the booze, the sun, and then the sex, we both took a nap but woke up and realized it was only about 5pm, and still light out. I made a joke or two about "wow, is it really only 5pm?!?" but we knew we weren't done for the evening. The resort had an amazing bar and pool but we were guessing that the room service wasn't that great. I looked at my phone, and had a text from someone identifying themself as Bill, which I figured out was Bill from that afternoon. I guess Courtney had given them my number instead of hers, ha! Bill said that he and Kristin had one of the fancy suite units at the resort, and did we want to come over for drinks and maybe dinner?

I told Courtney, and said she thought that would be fun but had one question.

"Aww, does that mean I have to put clothes on?" she asked playfully.

I took the bait.

"Well, they saw you naked all afternoon, so I suppose they wouldn't be offended. I think their suite is only a few doors down. I cant imagine anyone here would mind too much...that is...if you're feeling daring" I said, with a wink.

Her jaw dropped a little, at the suggestion of heading to Bill & Kristin's suite in the nude. I guess she hadn't expected me to raise the stakes that quickly.

"I don't know..." she started.

I was getting ready to throw up a hail mary with some reverse psychology here.

"I knew you wouldn't just walk over there like that!" I said.

She totally took the bait!

"You were there when I walked around the pool butt naked, right?" she asked, almost defiantly but with a smile.

"Well sure, but that was when everyone else was doing it too." I said, with a wink.

She smirked at me, and winked back.

I could tell she was at least thinking of it, but only time would tell if she would go through with it. She said she wanted a quick shower, so I texted Bill that we would be there in a half hour. He said great & that they'd have a round of drinks ready for us. Courtney ran off to the shower and I went for a quick walk to scout out the path to Bill & Kristin's place. It was at the other end of our same hallway, so the walk from their unit to ours wouldn't be too risky. I wasn't sure if she would actually go through with the dare but I figured I'd scope out the route anyways.

By the time I got back to our room, Courtney was out of the shower and getting ready. I figured I should probably grab a quick shower too so I hopped in. When I got out, Courtney was still naked. I threw on my bathing suit and a t-shirt and asked her if she was ready to go.

She just kind of shrugged her shoulders, and gestured down to her naked body.

"Yup!" she said, as if to prove me wrong.

"Alright! You showed me. And everyone else too, but definitely me!" I said.

We both laughed, and she gave me her phone to put in my pocket (and she was not amused at any of my suggestions about how she could carry it). Off we went.

"I cannot believe we're doing this!" she said, almost giddy.

"We? You're the naked one!" I said, looking up and down her body.

We both laughed. I took her by the hand and lead the way down the hallway toward Bill & Kristin's suite. She wasn't going to chicken out now! The hallway was completely quiet for the first few seconds, but, as soon we had the door to our room closed and had made it 10-15 feet from the door we heard a noise. A door opened down the hall and we froze for a second. A man & woman stepped into the hallway and turned to walk in our direction.

"We can turn back..." I said, quietly.

"Whatever, they probably saw me today by the pool anyways..." she said, with a giggle.

We kept on going.

The man & woman did look like they just came in from the pool. They both had on bathing suits, and seemed nice. They smiled and said hi, so did we, and maybe just for a second but they certainly got a good look at naked Courtney as we passed each other. They just kind of chuckled and Courtney giggled as we did our best to keep straight faces and act casual. I could almost hear Courtney's heart pounding as we got to the door of the suite and knocked.

"Here goes nothing!" she said.

I started to say something as I realized I heard more than two voices coming from inside, but the door opened suddenly and Bill was standing there.

"Hello! And...wow, hello!" he said as he realized Courtney was still naked.

Everyone halfway cheered and halfway laughed as Courtney walked into the suite naked. She was a big hit, for sure! Inside the living room of the suite was Bill, and Kristin, and another couple. Kristin had her bikini top from that afternoon on, with a pair of shorts. The other couple (lets call them Dan and Megan) were seated around the coffee table and got up to greet us. Megan had on a bikini top and shorts just like Kristin. In case you're wondering, it looked like Dan & Megan were friends of Bill & Kristin, in that Megan looked about 25 and Dan looked like he was close to 40. Megan was super cute and about 5'2''. She was a skinny little redhead with really big boobs for her tiny frame. She and Kristin had huge smiles on their faces as they realized Courtney was naked.

"Girl, didn't you pack any clothes for this trip?!?" Kristin asked Courtney with a laugh, and gave her a hug.

"Well, I heard this place was clothing optional, so I opted for no clothing. I really want a drink though!" Courtney said.

I had never seen this side of her, but I liked it.

Bill poured her a drink right away. I had to admit, she was rolling with it nicely. I could tell her heart was pounding but she was too competitive to chicken out so she just sat there, in a fully lit room with two strangers and two people we barely knew. At first, everyone just kind of pretended like there was nothing at all unusual about the situation. Everyone was sneaking a peek here and there but at first all we talked about was what to do for dinner. That went on for about ten minutes (and we decided on pizza delivery, and ordered the pizza) when the talk drifted to Courtney's nakedness and the fact that the other two girls were clothed still.

"I can't believe you did this! You're so brave! " Kristin said.

"Well, I cant believe that you're not doing this! Remember how much fun we had this afternoon? I figured why bother getting dressed?" Courtney said, with a giggle and a blush.

Isn't it amazing when women prod each other into sexy fun? I figured if I had pointed that out to Kristin, not only would she not have done it, I might have gotten slapped in the face. Instead, with Courtney doing it, she would seem like quite the prude if she didn't end up naked.

"Both of you were brave this afternoon! But she's right, honey! Why both with clothes?" Bill said.

Kristin smirked at Bill, then they seemed to wink at each other. I was guessing that this wasn't the first time they had a debate like this. Bill was clearly trying to get Kristin in on the fun. She hadn't seemed to be shy at all that afternoon when she slipped her bikini right off at Courtney's suggestion so I was thinking it probably wouldn't take much convincing.

"You know what we should do! We should get naked too, and then when the pizza gets here we should answer the door that way!" Kristin said, mostly to Megan but to the group.

It's easy to forget, but the "naked pizza dare" was a big thing a year or two before that. In case you either forgot, or missed it completely, the "naked pizza dare" was where a group of giggling girls would record themselves answering the door naked for a pizza delivery person as a prank/dare. This was typically done by college-aged girls but Kristin, Megan, and Courtney weren't too much older than that.

"Yes! We totally should!" Megan said.

"Okay, it's a dare! Well, I'm ready. Ladies?" Courtney said.

This was so far out of character for her that I was beginning to wonder if she had had some more tequila shots while I was in the shower.

Kristin and Megan sure didn't need to be told to get naked twice! Just like that, they both reached behind their backs, untied their tops, and let them fall off. We all stared with anxious anticipation! Then they both stood up and slid their shorts and bikini bottoms off in one motion, to the great applause & enjoyment of myself, Bill and Dan (and probably Courtney, ha!). I had seen plenty of Kristin that afternoon at the pool but this was my first look at Megan. She was somewhat fair-skinned, with her reddish hair but her tits looked amazing. I was guessing that they weren't real but she clearly had an amazing surgeon because they didn't look fake, just very perky! Her nipples were rock hard, and she had a soft landing strip of light reddish hair.

"Now it's a party!" Dan said, as we all watched the girls for a minute.

"Thats right boys...the carpet matches the drapes. Go ahead and get a good look, felals. Thats at least half the reason I still have that down there!" Megan said, noticing that we were all looking at her.

Megan and Kristin kept standing, knowing that we were all staring and jokingly striking model poses. They let us all get a good look for a minute or so before they sat back down.

We sat there, having drinks. Three lucky dudes and three naked ladies until we finally heard a knock on the door. The girls all looked at each other nervously and got up, giggling.

"Well, here goes nothing!" Megan said.

The ladies went over to the door, blushing and giggling. The funny thing to me was how nervous the girls were! That afternoon, Courtney and Kristin had walked naked across the whole pool area naked and ordered drinks naked at the bar, but they seemed to be more shy and nervous about the pizza guy than the crowd by the pool.

Kristin looked through the door's peephole.

"Oooh, I think he's cute!" she said.

The girls opened the door, and all kind of giggled and said hi at the same time. The pizza guy looked to be in his mid/late 20's. He seemed nice, and I could tell he enjoyed the view but if the girls were hoping to shock him, they failed. I guess that probably wasn't the first time that he had delivered to this place and probably not his first naked pizza dare. Still, he was grinning ear to ear and clearly having fun. He did his best to not look but come on, he was only human.

"Don't be shy, dude. If you don't look at least a little bit, I'm going to hear about it all night!" Bill said, from the living room.

Dan and I laughed as Kristin's jaw dropped and she teased Bill.

The pizza guy blushed a bit, but he looked all three ladies up and down while Kristin took her time counting out the money.

The pizza guy just about forgot to charge us for the pizza until Kristin reminded him and handed him the money. The girls giggled as they closed the door and brought the pizza in. The whole episode with the pizza guy probably lasted about 2 minutes but the girls were pretty amped up for the next hour or so as we ate and laughed. We sat and laughed about it and had a slice. All three girls stayed naked as we ate.

After we finished our pizza, Dan had an idea.

"Who wants to go for a quick swim? The pool is right outside..." he said.

"What's the dress code?" Megan asked him, jokingly.

"Yes, I'm sure you can stay naked. The pool is clothing optional during the day, I'm sure it is at night too." Bill said.

"Whatever, you just want us to stay naked!" Kristin teased.

"Guilty" Bill said, with Dan and I nodding in agreement.

The girls seemed up for it, but it seemed like one more drink would be needed. We Bill poured us another round. Finally we got ready to head outside. The girls grabbed towels but not bathing suits and they didn't wear the towels, they carried them. This was going to be awesome.

Being our first day there, Courtney and I had no idea what to expect with the pool in the evening. It was about 8:30 or 9:00 pm, so not super late but certainly after the prime day-time pool hours.

We got right outside the suite and sure enough it was only a few steps to the pool. We all kind of jumped right in. The girls were still naked, but the guys had our suits on for now. Certainly men are allowed to get naked at those places but 90% of the attention is always on the women. Nobody paid any real attention to me that day, but I was okay with that. Courtney on the other hand got plenty!

A little while passed, we swam around and played in the water. After the initial excitement of jumping into the water and everything, we got together and chatted some more. We realized we were the only people in the pool, but the bar had a bit of a crowd. The funny part though was that the bar crowd was fully clothed, in fact, they were not even in swimsuits. There was apparently some sort of event at the bar.

We were standing in the "shallow end" of the pool, far away from the bar but where the waist-high water which meant we still had a fantastic view of the ladies.

"So, you ladies feel underdressed?" I joked.

"Very funny! No, not really." Courtney said.

"I guess you won't mind going and getting us a drink then?" I said.

I knew I had her.

"You want me to walk through the bar area and all those people naked?!?" she said.

"Want you to? No, I am just saying you won't do it." I said.

"I didn't say I wouldn't!" she said back.

"Well, then consider it a dare!" I said.

She knew I had her.

Everyone laughed.

"Well, I'm not doing it alone!" she said.

We discussed as a group for a few minutes. The first thing I noticed was that the girls definitely seemed okay with the idea. At no point were we trying to talk them into it. All that was really debated was what they wanted in return. They clearly thought it would be fun, and sexy. They weren't going to do it for free, though.

Their first counter offer from the girls was that we all go over as a group. The guys shot that down.

"Sweetie, a bunch of naked girls casually stroll through a party at a poolside bar, you'll get grins, giggles, and maybe a handful of dirty looks from women whose boyfriends or husbands are staring at you. A bunch of naked dudes show up and not only will they not laugh but we'll be lucky if they don't call the cops." Bill said, and we all laughed.

He wasn't wrong.

We did eventually settle on what it would take. The girls were willing to go through with the dare, but they wanted us to take our suits off too. So, we get naked, and they go get us all a round of drinks, naked. Seemed fair enough.

"Alright! Game on!" I said, slipping my bathing suit off underwater and tossing it out of the pool onto a chair.

"Woohoo!" Courtney cheered.

Dan and Bill followed suit with their suits, and the girls cheered and catcalled us a bit. I suppose turnabout was fair play!

"Alright ladies, it's your turn!" I said.

The girls all sorta smirked at me as they headed for the stairs. For the most part, the crowd at the bar had not even really noticed us in the pool. The girls made their way up the stairs, dried off just a little bit and then made their way over toward the bar. Because the bar area had more lights on than the pool, I'm not sure if anyone saw them coming. Dan, Bill and I swam over toward the edge of the pool nearest the bar to watch the scene unfold.

At first, nobody caught on. The girls walked into the pool area like they owned the place, and a few heads turned but at first nobody really reacted. They made their way straight to the bar, and as you can imagine three naked women in the middle of a group of normally dressed people caused quite a stir. Nobody seemed upset though, mostly we just noticed some grins and laughs.

The bartender had the drinks ready after a few minutes, and the girls turned to make their way back. All three had a drink in each hand and a huge smile on their face. Oh, and rock hard nipples. Like, we were 30-40 feet away (I guess) but I could still see her nipples were rock hard. It looked like Courtney said hi to someone, but they mostly headed straight out and back toward the pool.

One of the only rules the place had was around glass and the pool so we got out of the water and set up some chairs for the girls to sit with us. They made their way over to us, huge grins and smiles on their faces.

"Well, I do stand corrected!" I said, winking at Courtney.

"Mmhmm, you do! We keep making these little bets, and you keep losing" Courtney said.

"Funny, I feel like I'm winning..." I said, looking at her hot body.

Everyone laughed at that one.

Courtney handed me my drink, gave me a small kiss on the cheek, and leaned in to whisper in my ear.

"You had better fuck me good tonight!" she whispered.

"Oh don't worry honey, I'm gonna!" I said out loud, which kind of tipped everyone off about what she had whispered.

We all laughed, again.

Our little group sat there and chatted for about 10 minutes, mostly talking about how awesome and brave the ladies were for doing their dare. I could tell that Courtney wasn't the only one who was revved up and ready to go, but we all finished our drinks and hung out for a bit. As much fun as it was to sit with three beautiful naked girls, the lighting was pretty dim and we were all pretty excited to get back to our rooms. A minute or so later, Courtney squeezed my hand which I was guessing was a sign she was ready to head back.

"Alright folks, I think Courtney and I are going to head back to our room." I said.

We all bid our goodbyes, and I thanks Bill & Kristin for inviting us over and told Dan & Megan it was nice to meet them. I put my suit back on, not so much to cover up but it was easier than carrying it. We dispersed, and the rest of the group headed toward Bill & Kristin's suite while Courtney and I headed toward our room. We were about halfway to the door when I heard a woman's voice call out Courtney's name.

"Courtney! Over here!" the voice said.

We turned, and a woman was walking our way with a man trying to keep pace.

"Oh, hey Kelly!" Courtney said.

Apparently Kristin and Bill weren't the only people Courtney met by the pool that day. She had met Kelly and her boyfriend by the pool that afternoon, and I was guessing that was who she had said hi to at the bar just now.