Nude in the Rooftop Pool

It was a sunny November day and warm enough to consider using the pool if it was heated. I dressed for dinner with a friend and left my room to meet her, but there was just enough time to check out the pool. I tried the elevator button for the top floor. It was locked. I tried the stairs, too, but the door was blocked. 

On the way to dinner, I stopped by the front desk and asked the person on duty, Chloe, about the pool. She said it was closed for a private event until 10 pm, but it would be open the rest of the night. My mind instantly started spinning out possibilities for the pool later that night. 

My first thought was to invite my friend to the hotel after dinner. That would be hard for her because it was so late and she had to be at work in the morning. On the way to the restaurant in her car I invited her to stay for a swim. As expected, I got a “thank you, but ” reply. I tried to put it out of my mind and just enjoy the dinner, but in quiet moments, my imagination took over. So many possibilities. In addition to some fun alone in the pool or a chance encounter with a stranger at the hotel bar after dinner, now there was Chloe, who would probably end her shift at 11 pm. Hmmm. 

But these were just snippets, barely formed outlines of something that might not even happen. It had been an exhausting trip and rest was probably the best choice.

I focused on being in the moment with a very dear friend, enjoying a memorable meal, thoughtful conversation, and making plans for future adventures with our spouses. I enjoyed our get togethers, which always involved travel because we live on opposite coasts of the U.S.

I really hated to say goodbye when she dropped me off at my hotel after dinner. It felt like the evening was incomplete. It was too late at night to call home because of the difference in time zones. It was an easy choice to just stop in the bar for a martini. I passed through the lobby and smiled at Chloe, who was chatting with another guest, and found my way to the bar, where I took a seat and surveyed the room. My thoughts were dangerous and I was already buzzing from some great wine that we had with dinner. It was time to go up for the night.

The bartender brought my drink and I asked if it was ok to take it up to the pool.

No one paid much attention as I paid and stood to leave with martini in hand.

Disappointed, but undaunted, I left for the nearest bank of elevators, stepping through the open doors, pushing the button for the top floor, and delighted in seeing it light up, igniting some fires deep inside me during the quick trip to the roof.

The entire top floor was dedicated to the pool facilities, including an indoor/outdoor bar and serving area, which was already closed for the night, and separate bathrooms with showers for men and women. The view, even late at night, was every bit as spectacular as I had dreamed. The lights up and down the beaches gave way to the darkness of the cold Pacific waters, punctuated by a surprising number of ships at sea. 

The private party was over, but there was still one group in a corner area, having drinks, laughing together, braving the chilly night with the help of a few outdoor patio heaters. It was cold enough for me to wish that I had worn something warmer than the skirt and and jacket outfit, which left my legs exposed from the knees down. I found a seat near a heater at the opposite end of the pool from the noisy group. There was one other person, a man, sitting it the dark, reading what looked like a large phone or a tablet. I sat quietly with my martini and plotted my next moves.

It was too cool to sit for long. My legs were cool to the touch. My hands felt like ice on my legs. It was time to finish my drink and move on.  I stood and walked to the edge of the pool, kneeling down to see if the water was warm. It was! I took my empty martini glass with me to the women’s bathroom, looking for security cameras on the way. It wasn’t 11 pm, yet. I thought of Chloe. She was young, very attractive, and possibly watching me on camera. That warmed me up. 

The bathroom was empty with several sinks and a large mirror along one wall. I stood looking at myself in the mirror, placing my martini glass on the counter, and warming up to the idea of a solo session in the pool. I started to undress, but realized that at any moment someone could walk in and it would be better to at least look like I had only come for an impromptu late night dip. 

I straightened myself up, picked up my glass and left the pool to go to my room, mentally gathering what my swimming outfit would…jog bra, leggings, hoody, cross- trainers, and flip flops. I always travel with something for a good workout and a pair of flip flops to wear around in the hotel room. It was the only plausible outfit that I could think of. And then, I would have to rely an old throw-away pair of bikini panties that wouldn’t fool anyone. 

In less than 5 minutes, I was dressed and on my way back to the pool. It was about 10:30 and I wanted to be in the water in time for the show I had created in my mind for Chloe. I walked onto the pool deck and looked around. The party people were getting ready to leave and the lone man had disappeared. It was time to lose the leggings.

I slipped into the bathroom to get set, so excited that my heart was pounding and I felt almost short of breath after removing the cross trainers, then while peeling off the leggings, trying to balance my bare feet on the flip flops. The image in the mirror, me in a hoodie, messy hair and old panties, was oddly comforting, making me feel at home. My hands naturally migrated to the bare skin of my thighs and now they felt warm. It was tempting to stay in the safety of the bathroom, the pleasurable feelings coursing though my body were undeniable as I pressed the puffiness of my labia through the old undies. But the pool, and the possibility of Chloe watching me on camera, called to me. 

I wrapped a pool towel around my waist, grabbed my things and another towel, then stepped out of the bathroom into the cold. It reminded me that I was in a very public area. The party people were gone by now, but people were free to wander out onto the pool deck at any time. I placed my shoes and leggings on a nearby chaise lounge, then took off my hoodie and laid it on top of the pile. My nipples reacted to the cold, tightening and pushing out against the fabric of my bra and I rewarded them with some soft pinches and tugs. The feeling was electric, as anyone watching could have seen.

Even with the cold, I really wanted to get in the water, so I went to the shallow end, leaving my towel and flip flops at the side of the pool and descended into the warm water one step at a time. It felt so much warmer than the air, which made the decision to keep going easy. I quickly walked to the center of the pool up to shoulder depth and slid both hands inside my panties, playing with my clit with my fingertips while tugging and massaging my lips. I turned to the direction of the entry door and kept masturbating, watching for anyone coming down the hall from the elevators. 

My panties were too inhibiting and I decided to pull them off. The water feels so different flowing freely between your thighs, especially when standing with your legs in a wider stance. I started bouncing up and down in the water and it was delicious feeling the soft pulsing of the water between my buns and across my pussy. It was tempting to keep going but I could tell it wasn’t enough to make me cum and there are, for me anyway, reasons why I didn’t want to insert fingers while in the water, so I focused on just getting a nice feeling going, then making a dash back to the room. 

I really had hoped that there were cameras and that maybe Chloe could see me in the pool. I didn’t bother putting my wet panties back on before climbing out of the pool and covering up with a towel. My nipples were clearly visible through my white jog bra. If anyone had walked out of the building onto the pool deck, they would have quite a show, but no one came. 

It was really cold after getting out of the water. I looked at the time on my phone and it was after 11pm. I picked up my shoes, hoodie, leggings and towel and went into the warmth of the bathroom to dry off and dress, but needed to pee, so I left my things by one of the sinks and went into a stall and sat down. 

The thought of Chloe lingered in my mind while I started to pee. For that moment, I was fixated on the fantasy of her watching me and then coming up to find me after finishing work. I barely waited to finish peeing before inserting a finger and fucking myself with one and two fingers as fast as I ever have, cumming and letting out gasps of pleasure while alone in the bathroom in what seemed like one long intense moment in time. 

The jog bra started to feel uncomfortable after the orgasm. It was wet and fortunately the pool towels were large enough for one to cover me top and bottom. I wasted no time stripping off the bra and went back to my room naked, except for the towel and flip flops, carrying everything else. 

When I was safely back in the warmth of the room, I fell naked into bed and let the fantasy take over again, envisioning Chloe joining me up on the roof, cumming on her own fingers while watching me.

I wonder when I will see her again and what I will tell her.