Time Taken Off

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.

*

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.

Leaning over, I cupped my hand on her soft breast. I could feel the erect nipple in my palm. I closed my eyes to enjoy the situation, squeezing her tits while getting jerked off. My fingers tweaked her hard nipples slightly. Her breathing intensified as time went on.

Karen moved in to kiss me again. She stopped wanking my shaft temporarily, but still held it firmly in her hand. As we kissed, she moved her body to sit on top of me, with her legs were straddling mine. All of a sudden I felt something strange. She no longer was holding my penis, but it felt different than just being in the hot water.

Extremely confused I thought to myself, "Holy crap, I think my cock was just in her pussy."

To this day I'm not entirely sure if it was. I can't even be sure how she would have removed her bikini bottoms to let my cock slide in. It happened so quickly. Combined with the hot water making my cock a little desensitized it was hard to tell what exactly happened. But either way it felt great.

Soon after she whispers in my ear, "I want you to fuck me. But I think we should wait until tomorrow."

We were both extremely drunk at the time, and I was starting to not feel great. So waiting actually made sense to me. We exchanged phone numbers and I told her that I'd call her the next morning. She re-tied her bikini and we got out of the hot tub. I kissed her goodnight.

The next morning I gave her a call. It went to voicemail, so I left the awkward message, "Hi Karen, it's the guy from last night. I'll be at the pool so stop by and say hello."

A large part of me was concerned she wouldn't show up. Perhaps she was wasted the night before and her judgment was impaired. She might wake up and realize that she hooked up with a guy that's about 20 years her junior. A million thoughts entered my head, convincing myself I wouldn't see her again.

But I was wrong. She showed up at the pool. "Sorry it took me so long to get down here," she said. "I had a conference call with some clients this morning."

"Oh that's terrible you have to work on your vacation."

She left out a sigh, "Ugh tell me about it. I actually need help with my computer. Are you good at that kind of thing?"

"Sure no problem."

We left the pool area and headed inside. "Well at least she is inviting me to her room," I thought. Inside her room, it took me all of 2 minutes to fix her computer problem. As I sat on the bed she bend over to pick something up off the ground. Through her white shorts I saw an outline of a thong. I instantly got hard, but tried to conceal it since I didn't want to look too pathetic.

I was hoping we would somehow have sex right then and there. But it didn't happen. Instead we made plans to go to Old San Juan to walk around. We spent the day together shopping and had a drink or two. At no point was the previous night mentioned. Our conversations were purely platonic and there was very little physical contact.

When we got back to the hotel I desperately needed to take a nap. She seemed disappointed, but being hung over in the Puerto Rico heat was putting me to sleep. I met up with her again in a hotel restaurant several hours later. She was sitting at the bar, and clearly she had several glasses of wine. I had a couple drinks but she was by far drunker than I was.

After she finished eating, she whispered in my ear in a sultry voice, "How about we get a bottle of wine and head back to my room?"

Without hesitation I replied, "Yes that sounds great."

We made our way to her room. At no point was the bottle of wine mentioned again. She sat down on her bed and I made my way to her bathroom. By the time I finished in the bathroom, she had already gotten changed. Beside the bed was a piling of clothing, including those white shorts I had spent so much time staring at earlier in the day. There she lay in nothing but a red silk robe.

Karen smiled at me and I smiled back. I stood in the doorway for a second, trying to capture a mental image of her on the bed. Her robe gently slid open. I finally got a good view of her tits. Her pinkish medium sized nipples were erect. Her breasts looked amazing for her age. Ever so slightly her robe opened more, and I saw a neatly trimmed pussy.

Slowly I pulled at the string formed neatly into a bow. It felt like opening a present on my birthday. She lay there staring back at me. I pulled the robe off her shoulders until she was wearing nothing at all. She let out a giggle like a schoolgirl.

"Want to go down to the hot tub?" she asked.

"You really want to go now?" I confusingly replied. She was already naked, why would I ever want her to put clothes back on.

"I want to suck your cock in the hot tub."

"Um I think the water might be a little hot for that."

"I'll only suck it when it's above the water."

I let out a huge laugh. I'm pretty sure she was serious, but it also gave me a pretty clear indication that she was drunk. I tried to convince her that having sex in a public hot tube might be difficult with all the cameras the resort probably has. Although, no one did bother us the night before. Eventually she agreed to stay in the room.

She sat up on the bed, and leaned in towards me. We shared a deep passionate kiss. My tongue wrested against hers. With my hands I caressed her bare naked back. We broke the kiss for a second and Karen pulled the shirt over my head. She glanced down at my shorts.

"We should take those off too," she said as she looked down at the budge. With one motion she ripped my shorts and boxers off. My dick stood up erect as ever. "Mhmm," she let out.

Karen moved her hand towards my shaft and finally grasped it firmly. Her fingers wrapped around the base. She gave it a couple of gently tugs. I leaned in to kiss her again. As we embraced, her tugs got harder and more aggressive. I started breathing slightly heavier. Karen began to rub the tip of my cock back and forth in her palm.

I reached my hand down towards her pussy. My fingers massaged over her pussy lips. She was already very wet. I let a finger slip inside of her, and it came out soaked in juices. I let it dip in a couple more times and could feel the muscles grasping my finger. I move towards her clit and start slowly rubbing. She let out a slight moan so I kept going. I massaged it in a circular motion with two fingers.

"I want you to cum inside me," Karen said to me.

Confused, I replied, "You want me to cum inside you?"

"No!" she yelled. "I don't want you to cum inside me. I want your cock in me."

I laughed at the confusion. I took the condom from my wallet that I always carry around with me in case of situations like this. I put a new one in my wallet right before I left home. The worst feeling in the world is having to throw a condom away because the expiration date has passed.

I wrapped the condom on rock hard shaft. She was lying on her back with her legs spread. I lowered my body down on top of her. Slowly I inserted my cock inside her wet pussy. It slid right in. Karen let out a soft moan. I felt the walls of her pussy grasp my member.

It was throbbing as I gave it a couple pumps deep inside of her. She gave out a deep moan. Her breath felt warm against my ear. I started going a little faster. The mattress was rocking back and forth on the bed frame with each thrust. I cupped her tits in my hand and gave them a firm squeeze.

"Harder," she panted loudly.

Karen's legs wrapped around me. My cock shoved in as deep as it could go. Her moans got much louder.

"Ohh ohh don't stop. Don't stop." She yelled out. I was sure that anyone in neighboring room would be able to hear. "Ohh fuck me. Fuck me."

There was a long mirror that ran the length of the bed. I turned my head and watched myself plow into her. There was a moment of reflection where I took my mind off the task at hand. Instead, I thought about how surreal it was that I was screwing this mature woman in Puerto Rico. Never in a million years did I think that was a possible scenario for my vacation.

"Ohh yesss," she continued to moan. "Cum for me baby. Cum for me."

"Yesss," I replied. My cock drove inside of her a couple more times. Finally, I whispered in her ear, "I'm cumming."

I gave one last hard push into her pussy and I let out a loud grunt. A river of semen spewed from my shaft into the condom. Laying there on top of her for several seconds, we both tried to catch out breaths. As my cock started to get limp I finally rolled off of her and made my way to the bathroom to get cleaned up.

Back on the bed, she looked into my eyes and said, "That was wonderful." She giggled again.

I laughed back, "I definitely had a good time. Thanks for having me over."

She smiled. "You ready to go again?"

Perplexed, I responded to her, "You mean right now? I only brought one condom!"

"What do you mean you only brought one condom? What did you think was going to happen here?"

I sat there in complete shock that this woman in her mid-40's had this much energy. I was completely exhausted. "Well I have more in my room."

She stared at me and said, "Ok hurry."

Without skipping a beat, I reached over to my pile of clothes. I grabbed for my shirt and shorts. My underwear sat on the floor since it seemed faster to not put them on. I grabbed her keycard so I could get back in the room. In the hallway, I realized the now obvious downside to skipping the underwear. My cock was still semi-hard. It created a noticeable bulge in my shorts, and considering what I had waiting for me it wasn't going away anytime soon.

I did my best to navigate the hallways as quickly as possible. Luckily I didn't see anyone on her floor. I pushed the elevator button. It seemed like an eternity but finally came after about a minute. It was completely empty. On my floor coming around the corner I spotted a young couple. I positioned my hands in front of my partial wood and they walked past without noticing.

In my room, I grabbed about 5 condoms from the box in my suitcase. Most of the time it would sound ridiculous to bring that many condoms on vacation, but I guess I was optimistic. Thankfully my optimism actually paid off for once. I rushed back to her room without a problem.

"I'm back," I yelled as I entered the room.

Karen was sitting on the side of the bed still completely naked. She smiled at me as I sat down next to her. I leaned in to kiss her full on lips. Our tongues wrestled each other for several minutes. My hands wandered, gently massaging her body. She pulled the shirt over my head once again, and removed my shorts. My cock stood straight up.

"So did you get them?" she asked inquisitively.

"Of course," I replied. I reached down to my shorts and pulled out the condoms.

"Haha," she laughed out loud, probably at the site of seeing so many.

Without hesitation, I lay down on the bed and ripped of one of the packages open. Once it was on, Karen got on top of me and straddled her legs.

"I'm still wet," she said. She lowered her pussy down onto my cock and let it slide in. Sitting upright on her knees, she began to raise and lower herself onto me. I did my best to thrust upwards as she was coming down. My cock slipped out once or twice. Finally, we got into a rhythm in which we were in sync. Whenever she sat down, my cock drilled in deep.

Even though I had cum once already, it still felt really good. I squeezed onto her tits. Karen arced her back, and supported herself with one arm. She began to scream out again. Without notice, she bounced up and down really hard and fast. The bed was shaking all over the place. Surely, if the neighbors didn't hear before they would hear now.