Pool Bar Romance

I was looking forward to this vacation for a while now. A week at the beach was just what I needed, pool, beach, sun, and lots of rum.

We spent the first morning at the beach. The kids played in the waves and looked for shells while my wife and I watched them from the beach chairs and soaked in the sun. We went back to the resort for lunch then headed for the pool.

The kids found other children about their age and made new instant friends. I found the pool bar. It was crowded and busy. The only bar tender was struggling to keep up. I sat in the last open chair at the far end of the bar. As soon as my butt touched the seat, the bar tender looked over, waved, and assured me she would be right over. I did not mind the wait. There were a lot of pretty women of all ages, shapes, and sizes wearing not much at all.

The bar tender finally made her way to me and said her name was Jess. She asked me what I wanted. I told her I wanted something fruity with lots of rum and asked her what her favorite rum drink was to make. She said it was a mai tai, and I ordered the first of many that afternoon.

As the afternoon went on, I began to notice Jess more and more. She seemed very young, maybe just out of high school. Her silky brown hair was pulled back tight into a high ponytail to keep it out of her way. She was about 5'05" and thin, not anorexic thin though with very small breasts that seemed to fit her small frame perfectly. She had a cute face with the tiniest diamond nose piercing that was barely noticeable until it caught the light. Her uniform was a simple polo shirt with a khaki skirt that reached just above her knees.

The next day we slept in. The wife and kids wanted to go into town to go shopping and see a movie. I went back to the pool bar. It was not nearly as busy at the bar with only a few other people coming and going. This gave me time to talk with Jess a bit. I thought maybe the evening before it might have been the strong rum drinks that got me thinking about her, but now talking with her while perfectly sober I realized something about her fascinated me.

She was older than I thought, 22 years old and just finishing up nursing school. I was glad I did not do any drunken flirting with her the evening before and embarrass myself. She was very open with me and talked about school, our jobs, and her recent breakup with her fiancé.

That afternoon Jess was giving a drink making class for some of the guests at the bar. I could not keep my eyes off her while she mixed drinks and explained what she was doing. I was not staring like I was at the milf in the bikini back at the pool. Rather I was watching all of her; how she smiled, moved her body and her facial expressions as she joked with the guests.

After the class, the bar was quiet. Jess was cleaning up and restocking supplies. I watched as she was slightly moving her hips to the steel drum music playing in the back ground. When she finished and came over to check on me. I told I was doing fine and just enjoying the sun as I watched the TVs at the bar. Instead of going back to her chores, Jess just leaned against the bar and chatted with me for a while again until other guests arrived for their last drinks before the bar closed down, it was only open in the afternoons until early evening so I don't want you to think I was spending all day at the bar stalking this girl.

The next day we went up the coast for the day so I didn't get a chance to go to the bar, but I could not stop thinking about Jess. What was it about her? She was cute, but there were many women at the resort much prettier and hotter than she was. Still she had a simple "plainness" that made her so.....cute. Cute is the perfect word for her.

The following day I made my way to the pool with the kids. They found their friends and I was off to the bar. I was surprised at how busy it was for a Thursday. Jess was working, but she would be so busy I would not get much time to talk with her. I would only get to watch her work and try not to look creepy.

As soon as Jess saw me she waved me to a seat right next to the register. She handed me a mai tai that was obviously meant for someone else who now had to wait for their drink. Jess said she was glad to see me and hoped I hadn't left. I handed her my credit card to start my tab, but she handed it back and said with a wink that she was buying my drinks for the day.

The pool bar was busy and stayed that way. A second bar tender form the restaurant came to help out, but Jess always insisted on getting my drinks herself. They were a little stronger today too.

Toward the end of the afternoon the bar quieted down and Jess was once again on her own at the bar. Jess was able to chat with me a little more now and it kind of seemed like she was flirting with me. She didn't really say anything overt, but her tone seemed to indicate she really liked me. Then as I was leaving, she ran around the bar to give me a hug. I had on a lot of tanning oil and it left a big stain on the front of her shirt. I apologized but she said not to worry because it was worth it.

The next day we were busy so I only had time for two drinks, but Jess was very happy to see me. Her hand lingered on mine for several minutes when I handed her my credit card. Her thumb was actually caressing my wrist.

Saturday was our last day at the resort and it was a drizzly rainy day. We packed up and my wife's sister came up to take my wife and the kids back to her place for a few more days of an extended vacation. I had to be back to work so I was going to just drive home by myself the next morning.

That afternoon I went back out to the pool bar hoping Jess was working. I found her at the bar chatting with the only couple who were braving the weather. I took a seat next to them, the only other seat under cover and dry. We all chatted about the crappy weather and how we were enjoying the week otherwise.

When the couple next to me left, I sheepishly told Jess that my wife left me and took the kids. Her jaw dropped and she quickly asked what happened. I smiled and explained that they left with her sister for a few days and I was on my own for the rest of the night and had to go home by myself. She laughed, threw a wet bar towel at me, and told me to never scare her like that again.

I figured it was now or never. I asked her if she wanted to go to dinner. To my delight she said she would love to. She said she would run home grab a shower and meet me at the restaurant. I then pushed it and asked her if she just wanted to have dinner in my room. Her smile faded and her shoulders dropped. I thought I had just screwed everything up. Jess said as much as she wanted too, she would get fired if she was even caught in the buildings with the guest rooms. The resort was strict about employees not fooling around with guests. Then she looked at me sideways and softly said we could get a hotel room if I wanted. I was instantly hard.

The rain cleared and several guests joined us at the bar. Our private conversations had to wait. I slipped Jess a note with my cell phone number and she gave me a note back with hers.

The drive to the restaurant took about an hour. Jess got there just as I reached the front door. She was dressed in a pair of shorts and a simple t-shirt, nothing revealing but so damn sexy just the same. We hugged tight and I enjoyed the way we fit together. She said she wasn't very hungry so we just had an appetizer and a couple of drinks. When we were finished, Jess announced she had already reserved a room at a hotel nearby. I followed her there and we checked in.

I wrapped my arm around her waist as we headed toward the elevator. She leaned her head on my shoulder and looked up at me with her soft brown eyes. We were alone in the elevator as we shared our first kiss. It was so soft and gentle. Her lips parted we gently touched our tongues together for the first time. The taste of her mouth was intoxicating. Now I realize why I was so enamored with her at the pool bar.

We reached the room and went in. Our kiss continued and deepened. Jess felt so good in my arms. We took our time, kissing and exploring each other's face. She was so amazing, so light and strong at the same time. I lifted up her shirt over her head and she did the same to mine. We moved over to the bed and I backed her up until she was lying on her back. I climbed on top of her and resumed our kissing as my hands explored her body. I kissed my way to her neck and nuzzled behind her ears as her short fingernails dug into my back.

I pushed her bra up exposing her small hard breasts. I kissed my way down and kissed and sucked her nipples. Her chest rose up pushing her breasts against my face as I played with her breasts. I moved my hand between her legs and up to her crotch. Now her hips rose to meet my hand, grinding herself against me as her breath quickened. I kissed my way to her tummy as my hands move to her hips and slid her shorts down her silky smooth legs.

I kissed farther down to her lower tummy just at the waist band of her low cut panties. I fingers traced the outline of the panties on her legs. Jess wiggled her shorts the rest of the way down her legs and off so she could spread her legs.

Jess placed her hands on my head and pushed my head lower. I obliged and kissed over her panties, feeling her neatly trimmed hair. I kept going and placed my whole mouth over her pantie covered pussy. I licked and kissed finding her clit. Jess loved the feeling of me eating her through her panties. It wasn't just my drool getting them wet, and her moaning told me I was doing what she liked. She began bucking against my face harder and harder. She begged me not to stop. Her orgasm was marked by a groan of satisfaction.

I slipped off my shoes and slip my shorts off. I climbed back on top of her and kissed her deeply as we started dry humping with our underwear still on. Jess grabbed my boxers and yanked them down as she told me to roll over. Jess climbed on top of me. She grabbed my wrists and pinned them to the bed as she kissed me all over and licked my face. Then she pulled her head back and just smiled at me.

Jess said it was her turn and she kissed her way down my chest and stomach. She took my cock in her hands and held it as she kissed her way down. She slid her mouth over my dick and began kissing and sucking and teasing me with her tongue. I ran my hands down her back as far as I could, almost reaching her ass. I pulled my hands back pulling her bra the rest of the way off.

I pulled Jess up to my face so I could kiss her again. I grabbed her hips as she began to grind herself against me. I pulled her tight so I could feel her breasts crushed against my chest. Her kiss was so wonderful it made me feel warm all over.

I flipped her over and pulled her panties down. I held her legs up and went down on her again, this time with no panties in my way. She tasted wonderful. I explored all of her with my mouth, enjoying the way she squirmed and bucked beneath me. I slid a finger inside her as I sucked on her clit. I ran my other hand along her tummy. I could feel her muscles twitch beneath my fingers as she came close to orgasm again. I swirled my tongue around her and inserted another finger. Jess fucked my hand as I sucked her until she shuttered with orgasm.

She was so wet now and my face was covered with her. I came up to kiss her. Jess kissed me with such passion, hands squeezing me where ever she could grab me, nails digging into my skin.

I pressed myself down on her and parted her legs with mine. My cock was between her legs rubbing against her clit. Then I pulled back and slowly eased myself inside her. She felt so good around me. I began slowly fucking her and enjoying every movement she made underneath me. Her kisses drew me deeper into her somehow. We settled into a rhythm, a slow steady deep rhythm. We were not fucking though. We were making love and it was the most sensual feeling I have ever had. Everything I did I did to please her sexually. I teased her clit with my fingers, I sucked on her breasts, I caressed every inch of skin I could touch, and we kissed. This lasted for over an hour.

We let the sensations build. When it got too intense and she was close to cuming I would back off just a bit to heighten the sensations. Finally I could feel Jess pushing harder against me. She was pushing at my hips trying to get me to go faster. I knew it was time now. I obliged and picked up the pace and hardened my strokes. I slammed against her as she groaned in approval and encouragement.

Even still, while I was pumping as hard as I could, we were still not just fucking. The sensations were overwhelming me. I was now as close as Jess was. As soon as I felt her start to orgasm I began as well. Jess arched her back lifting us both off the bed. I pushed back as deep as I could get while we both came together.

We were now covered in sweat as we slid our bodies against each other. I could not keep my hands off of her. I had to touch her all over. She was so beautiful.

I had to roll off her to catch my breath, even though the last thing I wanted was to break contact with her. Jess must have felt the same because she held herself over me and kiss my face all over. She told me no one had ever made her feel like that before. No one had treated her like she was so special. As she straddled me I was able to slide back inside her. We began to make love slowly again, this time Jess was setting the pace as we stared into each other's eyes.

It was morning before we knew it. One night seemed both eternal and a blink of an eye at the same time. I knew I had to say goodbye, but it was so hard. Jess seemed to know what I was feeling. She said she knew I was married and was not leaving my family anytime soon. She did not expect me to. She said she was so happy for that one night. She said it was just what she needed to feel like a woman again after being in so many shitty relationships. We live an 8 hour drive apart, but agreed to stay in touch and try to see each other as much as we can.