Swimming At The Cloisters

© 2020 Sal De Klerk, All Rights Reserved

Edited by ElmerStudd

Authors Note:

This story comes from a series of events in my life, and a healthy dose of imagination. The muse for combining reality and fantasy was "Stripped in the Pool'' by sensuallyembarrassed. I will leave it to you dear reader to decide what is fact and what is fiction. If you want more please ask. I do have an idea for at least one more chapter, but if no one lets me know they want more, why should I write it

Warning:

This story contains adult content including voyeurism, exhibitionism, CFNM, consumption of alcohol, public sex, vaginal fingering, and handjobs. If this is not your kind of smut, please find another story.

8========D

I worked for the Winter Park Police Department, a suburb of Orlando. To afford to live within the city limits I would work several off duty shifts a week. That allowed me to afford to live in the overpriced upscale city. Tonight I was working one of my favorite locations. An upscale four-story single building condo complex called The Cloisters. It was located a block or so from Park Ave the heart of the city.

My job was to make sure nothing happened during the night. The biggest problem was keeping drunks from skinny dipping in the pool after the bars closed. Most city residents were young singles or couples, but this condo housed a lot of seniors. The youngest resident was over 60 and there were four people over the century mark. So this location was not exactly a hotbed of activity at any time, especially at night.

I'd worked at The Cloisters several times a month for two years or so, and had only met two residents. My shift started at ten pm to and I got off at six am. By the time I arrived, the whole place was dark, except the lights on the east side parking lot. The west side of the building was the pool and hot tub, although hot tubs in Florida never made sense to me.

I'd worked this post so many times I had the routine down pat. Show up, radio in and walk around the property several times to make sure nothing happened. I'd fill out the daily report, leave it in the property managers dropbox and go home. It was boring, but easy money.

Well, one night, around three am, it was still hotter than fuck and around 90% humidity. I'd spent most of the night in my patrol car with the AC running. Every time I'd stepped out to make my rounds, the sweat would pour off my body like Niagara Falls. The night shift supervisor already swung by, and no one was ever out and about at this indecent hour. After making my usual patrol, I decided to take advantage of the very inviting pool.

I stripped off my uniform and locked it in the trunk of my car with my gun belt and body armor. Wearing only my boxers, I jogged over to the pool and eased myself into the cool water. I swam around for a while enjoying the cool water on my sweaty skin, it felt glorious. After three minutes or so, I began to feel guilty and climbed out of the pool.

I didn't have any towels with me so I dried off best I could. Then I figured that I needed to strip off my underwear. After all, I didn't want anyone to think I pissed myself. I took them off and threw them into the trunk of my car and slipped into my uniform. Once I looked like a cop again, I made another round. When I finished and returned to my car I felt as hot as before.

As I sat in my car, updating my duty log, I thought about how I felt when while naked in the parking lot. It felt like freedom, or the first time on a thrill ride, exciting and scary. I also got a thrill from my illicit swim. I knew I would go swimming again soon.

It was several weeks before I could sign up for a shift at The Cloisters. When I put my name won the roster, I felt a surge of electricity run through my body. All I could think about was going for a three am swim.

I arrived early for my shift. My excitement made me anxious to get there. I signed in and made my first round. Time seemed to drag as I waited for zero hour when I would take my dip. Nothing unusual happened that night. After an interminable wait, my watch chimed, to let me know it was three am.

I could hear on the radio it was a hectic night. There had been an event at Rollins College, and most of the department was dealing with the traffic. The usual public drunkenness and minor drug offenses continued as well. This meant the night supervisor was too preoccupied to check on off duty jobs.

I stripped down to my bathing suit, which I had worn under my uniform. Then I walked over to the pool carrying my towel. If a resident caught me, I'd claim to be someone's great-nephew having trouble sleeping. If a fellow cop caught me, I knew that the 'blue wall of silence' would protect me.

Smiling as I stood at the edge of the pool, I took a deep breath and jumped in. When I hit the water it felt sublime. I spent over an hour swimming, floating, and cooling off. When I climbed out I thought to myself, 'The only thing missing is a sexy female in a small bikini.'

I dried off as I walked back to my car. As my patrol car came into view, I remembered the thrill of stripping last time. I decided to take off my swimsuit, and walk the last 50 yards or so in the buff. There was a breeze blowing, which felt like ghost hands were fondling my cock and balls. The sensation was enchanting. I ambled to my car so I could experience the sensations coursing through me.

The next day I got a phone call from the Lieutenant in charge of off duty assignments. He asked me to pick up a couple of shifts at The Cloisters since I would be in court all week. I agreed my body charged with anticipation, knowing I wouldn't bring my swimsuit again.

For the next several nights I kept my boxers on while I walked to the pool. When I got close I would drop them and swim bare-assed naked. The second to last night, I took stripped before going through the pool fence and would leave my boxers on the gate. I loved the naked stroll to the water's edge.

On my last night, my cock got hard as soon as I arrived. I felt subdued with nervous anticipation. The clock ticked the seconds away, each one taking longer than the last. I left my boxers with my uniform, in the trunk and meandered to the pool.

Finally, my watch alarm beeped! It was three a.m. My cock spasmed as I hurried to my car and stripped off my entire uniform, leaving it in the trunk. All I had was a towel and flip flops. I headed to the pool for my perverse nightly ritual. I could feel my body relaxing during my trek. I thought about how free I felt when I went naked in the outdoors. I considered a weekend trip to Titusville to visit Playlinda beach. If I only had a lady to go with me.

I dropped my towel onto a lounge chair and stretched my back and sides. I realized I prolonged the time I spent exposed, enjoying the freedom. Then eased myself into the pool, using the stairs in the shallow end. Standing tall, I savored each step as I moved into deeper water. I delayed the amazing feeling of cool water surrounding my genitals as long as I could.

When I was waist deep, I ducked under and swam the length of the pool underwater. I decided to swim back to the shallow end without coming up for air. Once I returned to the shallow end, I lifted my head out of the water to breathe the sweet-smelling night air. As I did, I heard a female voice on my left say, "Hi stranger."

I whipped around at the unexpected greeting, "Holy Fuck!" I murmured when I saw her. My cop's mind went into overdrive, memorizing her details. Female, White, five foot six, 110 pounds. Early 20's, red hair to her shoulder blades, green sparkling eyes. Freckles on her forehead and around her eyes, fading out around her cleavage. She was wearing a modest bright yellow bikini, that showed off her flat stomach. She had a single belly piercing, a large emerald. No other visible marks scars or tattoos, on the front. Her finger and toenails were hot pink and her lips matched. Even if I wasn't naked, a woman this beautiful would have made me mute.

I stood there not knowing what to say as she stood on the pool deck, smiling at me. "Uhh hi," I stammered, despite the flock of butterflies in my stomach.

"I couldn't sleep, because my AC broke, so my apartment is way too hot. I figured a dip in the pool would help me cool off," she said, keeping her eyes locked on mine.

I wasn't sure if she noticed my lack of clothing from where she stood. If she got into the pool, she would definitely notice my rapidly expanding baton. "Yeah, sounds reasonable", I answered, as my mind raced with plans to get out of this dangerous situation. I needed to wrap my towel around my naked and very erect cock.

"I hope you don't mind if I join you. You aren't a rapist or ax murderer are you?" she giggled as she walked closer to the pool.

With each step she took, my anxiety grew. If she got in it was inevitable she would find more of me than expected. Then she would scream and all hell would break loose. She walked to the deep end and stopped at the edge. Sitting down, she dangled her legs in the water. I dove to down until my chest scrapped the bottom. Then I swam to the deep end. When I reached the wall I, using it to shield my nudity. I was only a few feet away from her. I leered at her long lean supple legs, trying to come up with a plan to extricate myself.

Looking at me, "Hi I'm April. I live across the street. I hope you won't call the cops and have them arrest me for trespassing," she admitted.

I swallowed hard, wondering if she knew who I was. I feared she wanted to get me in hot water, maybe file a sexual harassment or attempted rape charge. With the current anti-police sentiment among young people, I half expected her to bust a cap in my ass. I could see the headline:

RAPIST COP KILLED BY VICTIM

Now that would be a salacious story that would broadcast nationally. WPPD would never recover from that black eye. I knew I had to get out of there in a hurry. But I had no idea how. "I'm Tom," I replied to her.

"You're too young to live here," she said, winking at me. "Everyone here is at least 80."

Trying to be nonchalant I nodded. "I work here. I do overnight shifts and was on my lunch break," I told a half-truth.

"So that's why I only see you here some nights. Although it's been fun watching you strip naked and skinny dip the last few nights."

"Wait! What?" I exclaimed.

"I'm a bartender on Park Ave. I usually get home around three. I usually have a light snack before bed. My kitchen window overlooks this pool. I've seen you out here a few times swimming around as I ate. When I realized you swam naked, I kept my lights off so I could see better. Then yesterday I bought a pair of binoculars and watched you strip down before jumping in. Tonight I decided to join you."

My face was burning, knowing that my escapades hadn't been as secret as I believed. If she had seen me all those times, then who else had witnessed my foray into nudism. Now I was glad that my patrol car was on the other side of the building, out of her line of sight. She had no idea I was a cop. I breathed a sigh of relief at that, but I knew I had to go, SOON. The hourly radio check was coming up. If I missed it, several patrol cars would roll up, lights flashing, to check on me. That would be bad. If one cop that found me naked in a pool talking to a hot redhead could keep it from the brass. If Several cops and a supervisor found me it would mean suspension, if not termination.

"Since you know I'm naked, you won't mind me getting out and going? My break's over and I need to get back to work."

April pouted, "But we were getting to know each other," she complained. "Can we meet here tomorrow night?"

"I wish I could, but I won't be here on overnights, for a few days at least," I replied.

"Well here's my number, text me when you will be here, and we can meet up. Next time, I'll bring you lunch." She winked at me as she wrote her number on my hand with a Sharpie. 'This girl comes prepared,' I thought as I turned pushed myself up out of the pool.

April sat there watching me, or a certain part of me as I collected my towel. I draped it over my shoulder, turned my head and called out, "Be careful swimming here. The property manager has a cop here every night. If he catches you, you might get arrested for trespassing."

"So why don't you get arrested?" she asked.

"I told you, I work here," then I winked at her and strode off. I opened my trunk in time to hear dispatch giving a second call for me. I grabbed the mic and responded in a strong voice, "post 24, 10-4." The district sergeant was a cop I had gone to the academy with and we detested each other. As soon as the check ended, he told me to switch to a secondary freq.

I switched over, "What's up sarge?" I inquired.

"Why the fuck didn't you answer the first call!" he demanded in his belligerent tone.

"I had a mouth full of nice tender roast beef on rye." I lied knowing that he recently found out he was allergic to meat, couldn't eat his beloved roast beef sandwiches anymore.

There was a brief pause, but his anger was so strong I could feel it emanate from the radio. "Switchback," was his reply.

I switched back, to the primary channel for the zone, and checked back in with dispatch.

By this time I had finished dressing and decided to check out the pool to see if April was still there. I arrived in time to watch her run across the street and go inside an apartment building. I stood there watching the windows to see if a light went on in an apartment. I was disappointed.

At six am I closed out the reports, leaving out the trespassing April. I drove to the station to see if I could sign up for more shifts at The Cloisters. I was lucky, the new sign up hung from the bulletin board, and no one had signed up for any shifts. I put my name down for The Cloisters for every shift that wouldn't affect my duty schedule. I wanted to see more of April again soon.

On my lunch break, I texted April

Me: Nice 2 meet u. hope we can hang again soon.

April: Let me no when ull b in pool Ill bring u sumthing sweet 2 eat.'

My dick leapt at the thought of eating the sweet sexy April. The rest of my shift was a blur. Two days later I was in court on a drunk driving case. A scumbag ambulance chaser with eight DUI arrests, and in six of those he assaulted an officer. The man was a millionaire and usually got off with a $500 fine and six months probation.

My neighbor had a clean record. He got one DUI and it cost him over $10,000 dollars and his license got revoked. 'Must be nice to be rich and have the DA as a golf buddy' I thought in anger.

After the judge adjudicated the case, I headed home. I was only a few blocks away when my phone rang.

"Officer Houlihan."

"Hey Tom it's Lieutenant Flynn."

"What's up Lieu?"

"I need you to work The Cloisters tonight. Officer Hanson got hurt in a fight and is on sick leave. I know you're duty shift is eight to eight tomorrow. I checked with the shift sup and he approved you to work as house mouse noon to mid, instead. Can you do me the solid?"

"Wilco, but how's Hanson? We were in the Academy together."

"She'll live. A couple of broken bones from a bad fall. They want to observe her for a day or two before sending her home."

"Shit! Her husbands Gaurd unit deployed last week, and she has two tender age kids. Can you let everyone know I'll be setting up a meal train for them?"

"I'll let everyone know. Thanks."

When I parked my car, I sent April a text:

Me: I'll b @ pool 2nite. Hope it's sticky sweet.

April: c u there @ 3. hope u wear same suit ;)

I looked up the duty roster to see who the night supervisor was. It was Sargent Lopez, an old-timer, who drove up and down Park Ave scoping out the college girls as they bar hopped. He never checked on me or any other off duty post, unless something happened.

I took a nap and woke up when my alarm went off at 9:30. I ate some leftover pizza and put on a clean uniform. I drove to The Cloisters and began my shift. It was the same old same old. I wanted to get to the pool before April, so I set my watch for 2:45. I knew I would be comfortable naked in the water. Walking up to the pool naked with someones watching was a bit intimidating.

I removed my uniform and walked over to the pool. I brought my swimsuit but didn't wear it. My cock and balls were swinging free. I jumped into the water, and when I surfaced I heard a now-familiar female voice, "Hi stranger."

Spinning toward the sound, I smiled at April. She looked exactly the same, except her bathing suit was green instead of yellow.

"Hi yourself," I replied as I stood up in waist-deep water, drinking in her nubile form. I wondered how far we would go tonight. 'I can't wait to get her out of that suit,' I thought as my eyes drunk in her well-formed calves. I let my eyes follow them up past her sexy knees and over her toned thighs, until I reached the valley of hidden delight. 'Hopefully, it won't be hidden for much longer.'

"I have some food set up on the table over here," she said, smiling and pointing to a table nearby. I looked over and saw an honest to god picnic basket. Looking at her I mumbled, "You promised sticky sweet."

She must have heard me because she gave me a curious look. "Well get out of the pool. Then you'd see I have homemade honey buns and individual strawberry shortcakes. Now join me."

She turned her back and walked over to the table. Her jiggling ass cheeks enticed me out of the water, and I followed her delectable ass to the table. She unloaded her goodies, though they weren't the goodies I desired.

After watching her unpack some plates and silverware, I shrugged my shoulders and got out of the pool. I walked over to the table and sat down. I realized the table she chose had a glass top, so it wasn't hiding my dick from her view. She served me a piece of shortcake and a honey bun, then served herself some and sat down next to me.

As I put the first forkful of the cake into my mouth, I realized her naked thigh was touching mine. It was soft and warm, the heat headed straight to my dick. As I swallowed I wanted to compliment her skills in the kitchen. Before I could open my mouth, her hand grabbed my semi-erect dick and started teasing it. My eyes sprang wide open and I looked over at her.

April was looking down at her hand on my cock, watching as she caressed it up and down. She had a small smile on her face as she watched it grow to its full size. She was an expert at giving handjobs. She teased my shaft and caressed the head, and even played with my balls. All the while sitting there eating the deserts she had made. I decided not to ruin a good thing and sat there letting her stroke my dick, feeling the cum churning in my balls. I wanted to explode, but I hoped it wouldn't be on my chest or the concrete pool deck.

The whole situation was surreal. I was naked, while on duty, getting a handjob from a beautiful woman, dressed in a bikini, who had been a peeping Tom to my Lady Godiva. Neither of us were talking to each other and this was only the second time we had met. I shook my head and continued to eat the delicious treats, enjoying the way she handled my cock and balls.

As she took her last bite, she increased the tempo of her hand and used my pre-cum to ease some of the friction. She had grown serious about making me cum. Her hand was a blur as it pulled the cum from my balls. I sat there moaning softly as I felt my dick begin to enlarge. I tried to hold back as long as I could. April's smile had grown as she felt the pressure build.

"Cum for me baby," she whispered as she put her other hand on my chest and pinched my nipple.

"FFUUUCCCCKKKKK," I moaned, as my dick exploded, blasting cum all over the cement under the table. Her eyes widened and her breathing quickened as she watched my thick white cream blast out of my dick.