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.
The weather in the winter of 2015/2016 was especially bad where I lived. It seemed like every day set a new record low temperature for the city and at least three or four times we had a major snowstorm. However, right as winter set in I met a young lady who helped keep me warm. Let's call her "Courtney", and she was a cute brunette. For whatever reason, we only dated a couple of months, but we did have two or three really fun adventures. My wildest days had passed, and so had hers. We were both in our 30's, and we were certainly open to the idea of some adventures but the wild parties in some of my other stories were few and far between at this point. But the combination of crazy low temperatures and snow lead Courtney and I to escape the city for a few days, and it lead to our first adventure.
We had been on a few dates, and had hooked up a few times. The sex was pretty good! She had a really good body, but she was totally shy. I told her a couple of my stories, and her jaw dropped every single time. She kept telling me she was too shy for something like that but I could also tell that the idea of showing off a little bit turned her on a lot. Especially when I brought up the idea of getting out of town for a few days. It may have been freezing cold up north but it was 80+ degrees and sunny in Florida. I found an upscale resort that catered to couples, didn't allow kids, and had a clothing optional pool area. Now, I just had to convince Courtney!
She seemed okay with the idea overall, and she loved the idea of getting out of the freezing cold city and going someplace warm. She did freak a little when I showed her the place, but I pointed out that the fact that it didn't allow kids meant that the pool area wouldn't be overrun by kids running and screaming and all that, and also that the booze would flow a little harder. Sure enough, the pool area looked like it had at least two or three bars. And I told her that "clothing optional" meant that we could opt for bathing suits, or, opt for no bathing suits. She wouldn't have to go naked if she didn't want to. Now, of course, I knew that she was the type who would go with the flow once we got there but that was beside the point.
Once we talked it through, she really liked the idea. She said she might take her top off but that she planned to keep her bottoms on. I knew she would take her top off, especially after a few drinks but I said that was fine, and even offered to buy her a new bathing suit. I told her we should have some fun with it. She could bring one of her normal bikinis but that I would buy her a new, much naughtier and skimpier bikini that she probably wouldn't wear anywhere else. She blushed and I could tell she liked the idea. We shopped online and found one that was barely there, and she blushed, but she said it was okay so I ordered it. Side note, I am still on that company's email list all these years later. The super skimpy bikini came a few days later and she modeled it for me as we planned the trip. The top was just two tiny triangle's that did not even cover her entire breast and was held up by strings. The bottom was a tiny patch that kind of covered her pussy, and only had a G-string for the back. She had just had a Brazilian wax done so it looked kind of funny but by the time we got down south it would look smooth and sexy! I bought a new bathing suit too but I realized that nobody would be looking at me as long as I was next to Courtney. We packed for the trip that night and just a few days later we were headed south.
The main thing I was worried about with the resort was actual the weather. The trip was planned for early March, and while that part of Florida is usually 80+ degrees and sunny, the thing that had the biggest potential to ruin the sexy fun was if it was 65 and overcast the entire time. As long as the weather cooperated, I was confident that we would get plenty of booze and have tons of fun by the pool. I was also confident that Courtney would be naked in no time. She said she wanted to keep her bottoms on but that was just because she had never been before. I suspected if the other women were doing it, she would want to do it too.
Finally, the day of the trip came. It was about 15 degrees when we left for the airport at 6am and we landed in 75 degree Florida at 11am or so. I checked the weather app on my phone and it was supposed to be 80 by the time we had lunch and got to the pool. Perfect! We got a rental car and headed out to the resort. It looked somewhat normal from the outside but I could tell pretty quickly when we got inside that it was going to be a fun place. The checkin process included a review of the rules for the resort, including rules against cameras and an explanation of the clothing-optional policies. I could tell Courtney was a little nervous but so far she was having fun. We made our way to our room, and then changed into our suits. I knew she was open to the idea of fun and sexiness when she put sunscreen on all the areas normally covered by her suit before we got to the pool. We had planned to grab lunch by the pool in their restaurant and then lay by the pool for a bit. It was a little bit crowded (apparently we weren't the only yankees who had the idea to escape winter for the weekend) but it looked like there were still plenty of lounge chairs left. In order to help ease Courtney into the fun, we agreed she would wear her normal bikini the first day, and the new naughty bikini the second and third days. Not that her "regular" bikini was terribly modest, but I was excited to see her strut around the pool area in the new naughty one.
We got to the bar area for lunch and walked right past the pool on our way and I could tell she was getting more and more comfortable by the minute. Maybe the margarita that tasted like it was 90% tequila helped, or maybe just seeing the pool area and realizing that it was going to be fun after all. Probably she had built it up some in her head but now that we were there, it seemed way less intimidating. She had a second margarita and seemed like she was ready to get to the pool. We had a couple of quick sandwiches for lunch and headed to the pool!
Right away I noticed that most of the women were topless but only about half of the women were nude. The men were about the same. Before we got settled, I could tell she was thinking about something and I asked her if she wanted to go change into the skimpier bikini. It turned out that was exactly what she was thinking. I gave her the room key and told her to go ahead and that I would find a good spot for us. She gave me a kiss on the cheek and took off toward the rooms. I walked around and found a good spot with two lounge chairs and a good view of the pool area. It was pretty far from the bar but I actually had a plan for that. I texted Courtney my location and settled in. I felt a little awkward at first, realizing that single men are generally not welcome at these places. I made sure to spread out Courtney's towel on her chair so that hopefully people assumed that I wasn't there alone. I scanned the pool area and just enjoyed the sun and margaritas. There were so many people!
An important detail about Courtney is that of all the girls I knew in those days, she didn't have the prettiest face but she might have had the best body. That's not to say her face was ugly, but she wasn't really into makeup or fancy hair. She usually had messy hair in a ponytail, no makeup, and always dressed modestly. The first time she got naked in my apartment was somewhat of a revelation. I was like "uh...wow!". Once you got underneath the layers, she was amazing.
About 10 minutes later, Courtney showed up. She had on a sheer coverup that didn't cover much up, and the sexy bikini that so far she had only dared to wear inside my apartment. I could tell that she felt bold and daring! She dropped the coverup and certainly got the attention of the people nearby. From the back, it was hard to tell if she was naked or not. She sat down on her lounge chair next to me, and we started talking.
"You were totally right. This place is great!" she said.
Maybe it was just the sense of relief that it was actually fun, or maybe it was the two margaritas talking. We sat and enjoyed the pool for a bit. She scooted her chair slightly closer to mine, so we could talk without anyone hearing us.
"Babe, I'm so horny!" she said, barely above a whisper.
"Oh yeah?" I said, also barely above a whisper.
"Yesss!" she said.
"I have a dare for you then." I said.
"Ooooooooh?" she asked.
"I dare you to stand up, in your naughty bikini, and walk all the way over to the bar, and get one drink. Just one, don't get two." I said.
She stood up, in just her tiny bikini, and walked over toward the bar. Granted, there were plenty of naked women by the pool area, but she still turned a head or two. She had a great ass, and the tiny g-string barely covered anything. She walked all the way over to the bar. I watched heads turn, both male and female, to follow her over. She stood by the bar, waiting to order a drink. I could tell that she was excited. She had barely anything covering her, and she was standing in line, waiting for a drink. It looked like a couple in line was making some friendly conversation with her. I knew that would turn her on. Finally it was her turn. She ordered a drink, got it, and walked back to our lounge chairs with it. Again, I watched her as she walked and noticed she was attracting plenty of attention.
She got back, and handed me the drink. I sat up, and she leaned in to kiss me on the cheek as she handed it to me. Then she sat back down.
"OMG, that was amazing." she said.
