Author's Note -- This is a true story of an event that occurred to me a couple of years ago. The names have been changed.
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My company has a policy that states if you don't use your vacation days you can roll five days over to the first quarter of the next year. In 2007, I was a 25 year old who was relatively low on the totem pole at work. Due to a lot of personnel movements within the company, I was not in a position where I could take a lot of days off. I was put in a situation where I had to take advantage of that policy. However, by March of 2008, I had not taken a single one of the five days and they were due to expire at the end of the month.
After completing the impossible task of trying to find someone to cover my job for me, I put in for a week off at the end of the month. Once the week finally came I got bored quickly. All my friends were working and I sat on my couch for 3 straight days watching TV. I had to go somewhere.
After scouring the travel websites for a hot weather location, I finally came across an amazing deal in Puerto Rico. It was at a well-known high-class hotel chain. Let's call it Spitz Farelton. Obviously not being independently wealthy, I jumped at the chance to take advantage of the rock bottom prices due to the poor economy. I had previously been on vacation by myself, so I didn't mind going alone on this trip as well.
That Wednesday I boarded a plane for Puerto Rico. I landed in the late afternoon. I figured I would take it easy that night and just hang out at the hotel. After unloading my luggage in the hotel room, I took a stroll around. The hotel was far nicer than most of the places I end up staying. The hotel staff was actually friendly and attentive.
I walked through the pool area. There were still some sunbathers trying to soak up the last couple rays before the sun went down. I noticed a couple of hot European girls lounging in hot pink and blue bikinis. One was lying on her back and had amazing, perfectly round tits. The other was on her stomach and had on a string thong that really showed off her ass. Her top was untied so her back was bare naked.
At that moment I was thinking I made a good decision to come here. It was the spring break time of year for colleges, but Spitz Farelton was clearly not a place a poor college kid would go. I was a little concerned who would be there, but my worrying was clearly unwarranted. Walking around the pool, there were some other groups of girls and the occasional family mixed in.
I spotted the bar near the pool and took a seat. In past experience, the bar was often a great place to meet other people. I picked an empty seat and ordered a drink. Mostly I kept to myself for the first twenty or so minutes. There were two mid-30's couples also at the bar but I didn't want to interrupt their conversation. Finally, I overheard one mention being from New York. Also being from New York, I quickly interjected "where in New York are you from?" We got to talking, only to realize they were all captains of industry and here I was barely able to pay my rent.
A couple hours later, a mid-40's woman came over and asked me if anyone was using the chair next to me. She sat down and ordered dinner. I didn't pay much attention to her since she was eating and I was involved in conversation. The couples left, except for one of the guys. He brought the woman into our what we were discussing.
This woman, Karen, was a lawyer from Boston. I almost choked on my drink when she mentioned she charges $700 per hour for her services. Karen lived at the Spitz Farelton in Boston. She had blonde wavy hair and fair skin. Her white shorts came midway up her thighs, and she was wearing a blue sleeveless shirt on top. Despite being pretty drunk at the time, I wasn't really thinking of her in a sexual way at all. Although I love older woman, I had never been with one and always thought that was out of the realm of possibilities.
The conversation went on between the three of us for several more hours until it was dark out. Karen and I would gently touch each other in the flirtatious way, but it really didn't seem like a big deal at the time. I even put my hand on her shoulder and joked about how I was looking for a sugar mama. At one point, she got up to go to the bathroom.
The guy turned to me, "You know she's ready to go, right?"
Confused, I replied, "What do you mean?"
"You know," he said while nodding his head and had a suggestive look in his eyes.
Finally it hit me that meant he meant I had a shot with her. Surprised by his comment I responded, "Really?"
"Oh yeah, big time," he said. Perhaps I was too drunk to notice, which is strange because I'm usually constantly looking to get laid when I'm drunk.
Karen returned from the bathroom and sat down close to me. Maybe the guy was correct after all. After about 10 minutes, he said goodnight and left to find his wife. Karen and I talked for a little while longer. The bar was closing at 9 pm so we paid our tabs and got up to leave. As we walked together by the hot tub Karen said, "Let's get in." There were about 5 people currently in the hot tub at the time.
"I'd love to, but I don't have a bathing suit on," I said.
She looked at me, "I'm sure you can go in with your underwear on."
I glanced back towards the hot tub looking at all the people in there. "Um yeah, let me just run upstairs to my room."
Racing to my room, I got changed and came back down. By the time I got there, the 5 people in the hot tub were no longer in it and were packing up their stuff. The only person still in there was Karen. She gave me a hug smile when she saw me. I thought to myself, "This is interesting."
I lowered myself slowly into the piping hot water. I ended up sitting several feet away from Karen. She immediately moved to sit next to me. As she got up I noticed her blue bikini. Her breasts sat nicely in her top. They were probably B or C cups. I suddenly got hard just from looking at her.
When she sat her tits brushed against my arm. She left no room in between us. I felt her leg pressed up against mine. There was no one else around, including members of the hotel staff. I turned to look her in the eyes and she did the same. Our faces were inches apart. After gazing at each other for a couple seconds, I leaned in and kissed her on the lips.
She put her arms around my body, and kissed me back. I gently slid my tongue into her mouth. Karen's tongue wrestled mine. I put my hands on her lower back and felt her bare skin. Her body was pretty nice considering her age. I gently rubbed the small of her back and she did the same to me. My hands drifted up and down her toned legs.
Being the only people in a fairly large hot tub, we floated around a bit. After several minutes she broke our kiss. Karen wandered towards the middle of the hot tub while I sat near the wall. She stared into my eyes and had a huge mischievous smile. Her hands then moved to behind her neck. Karen took hold of the string knot of her bikini top and let it unravel.
I stared in amazement as the two straps of the bikini fell. Unfortunately her tits were beneath the surface of the bubbly water, so I couldn't get a great look at them. Karen inched towards me and pushed her body against mine. I wrapped my arms around her. Her breasts pushed up hard against my chest and we kissed again.
Suddenly, I felt her hand move away from my back and start to head downwards on my body. It finally came to rest at the front waistband of my bathing suit. While we were still making out, Karen's hand moved to my crotch. My cock had been hard for a while now, and she squeezed the outline of it through my suit. She made several jerking motions with her hand.
Apparently unsatisfied with just feeling the outline of my cock she made another move. Her hand slipped onto my thigh and moved upwards into my trunks. Karen took a firm hold of my rock hard shaft in her hand. She played with it for a little while, moving her hand up and down between the tip and my balls. It felt good in the hot bubbling water.
My penis was way too restricted within my shorts, so Karen yanked it out. Even though it was still underneath the water surface, I undoubtedly felt nervous about being exposed in a public setting. Karen however seemed unfazed by the situation. Once again she broke our kiss. I could feel her warm breath in my ear as she looked down to jerk my cock. At first she was gentle and started slow, but she sped up over time.
