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I apologize for the delay in getting the second chapter of this series out. I had a combination of writers’ block, real-life, and ideas for other stories before I could continue this one. I hope it was worth the wait.
After my night with Rita, I returned to Chicago to talk to some people there about advertising. I had a few friends who were in the ad business, as well as a former FWB who owned a string of travel agencies. I also talked to a buddy of mine who was a lawyer, and soon I had all of the arrangements made to try to get some business headed to my new resort.
My travel agent friend suggested that I invite a few of her colleagues down for a look at the resort, so I had her put out some feelers for me.
Having been a “working stiff” all of my life, and knowing how hard it could be to make ends meet and still take a vacation, I decided that I was going to cater to people like me, and try to give then an affordable escape. I knew that was what my uncle would have wanted.
Part of my plan was to give teachers, cops, fire fighters, and military a good price on a stay with us.
When I returned, with Valentine, Rita, and Betsy helping, I was able to work out quite a few deals with the locals, assuring everything from decent taxi rates to food and liquor supplies. It seems that my uncle had developed a great reputation as a good man, something that really didn’t surprise me, which also helped.
After a couple of months, business was slowly starting to pick up. We went from only a couple of bookings a month to a couple every week.
As I walked into the lobby one morning, I saw Rita talking to a group of women, with Valentine standing nearby with a pile of luggage.
There were four women in all, and Rita told me later that they were all family members, the youngest in her early twenties, her mother, and her grandmother and great-aunt. The two younger women were wearing sun dresses, while the older two were in what looked like the ugliest, baggiest “mom jeans” I’d ever seen.
I stayed out of the way, and then watched as Valentine walked them down the path to their villa.
Rita came out of the lobby and told me that they were the only guests booked for the week so far. She had put them in the two bedroom villas, which were about fifty yards apart, the older women in one, and the younger in the other.
A couple hours later, as I was stocking the bar, all four women came walking down the path from their villa. I could see that the youngest was very pretty, but it was her mother that really caught my attention.
I guessed her to be in her late 30’s or early 40’s, maybe about 5′ 4″, and, as the saying goes, ‘curves in all the right places’. With shoulder length blonde hair and glasses, she had a hot, girl-next-door quality about her, and a body that matched.
“Ladies,” I asked, as they walked up to the bar. “Can I get you anything?”
“It’s a little early to drink, isn’t it?” one of the older women asked.
“Ma’am, I’m Irish and German,” I replied laughing. “It’s never too early to start drinking. Besides, it is after noon, and you’re on vacation. There are no rules.”
“Well, I think it’s too early,” she shot back. “We came down for some lunch.”
“Not a problem. You can have a seat out here by the pool, and I’ll have someone out here as quickly as I can, or you can go into the dining room, right through those doors,” I told them.
The two older women looked at each other, and the other one spoke up.
“I’m not one for eating outdoors,” she said, and started walking to the dining room.
The two younger women looked at each other and rolled their eyes.
“We’ll be there in a minute,” the older one said. “I want to get something to drink.”
Both of the older women looked at each other, and the mom shot them a look of disapproval before they walked off.
“I can have something sent to you, if you’d like,” I told her.
“No, this is fine,” she replied softly.
She and her daughter stepped up to the bar.
“I’m sorry,” the mom said. “That was my mother and my aunt. They mean well, but …”
“Say no more,” I replied with a smile. “I’ve got a ‘means well’ mother myself. What can I get you?”
“Well,” the mom said, smiling at me, “I could go for something fruity, with rum. LOTS of rum. I have a feeling I’m going to need it.”
“I can do that for you,” I smiled back.
“And for you, young lady?” I asked her daughter.
“I’ll have something fruity too, but virgin,” she replied.
“Not a problem,” I told her. “One virgin punch, and one a little slutty, coming right up.”
Both ladies laughed and sat at the bar as I started making their drinks.
“You work here?” the mom asked.
“Yeah, you could say that,” I replied.
“Cool. So, you’ll be here all week?”
“That I will,” I told her.
“Good. It’s always nice to know your bartender,” she said, smiling at me again.
Getting lost in her smile for a second, I told her I agreed, and went back to blending the drinks.
“I’m Debbie,” taksim üniversiteli escort she said, extending her hand across the bar as I cut up some fresh fruit. “This is my daughter, Christine, and those other two are my mother, Ellen and my aunt, Pat.”
“Debbie, Christine, the pleasure is all mine,” I told them, shaking their hands.
I could’ve sworn I felt a spark as my hand made contact with Debbie’s, and she continued smiling at me.
A few minutes later, I handed the women their drinks, and watched as they walked into the dining room to join the others.
Later that night, after the women walked around the property, and then had dinner, they all walked up to the bar.
“Ladies,” I greeted them as they sat down. “Would you like a drink, or is it still too early for you?”
Debbie and Christine both smiled at that comment, Christine looking like she was trying hard not to laugh out loud.
“I could definitely go for something,” the one called Pat replied. “Do you have any Scotch?”
“I do,” I told her. “We have some stored away somewhere. However, you’re in the islands, ladies. May I recommend something a bit more tropical?”
“Like what?” Ellen asked, not looking very happy.
“Well, you’re in Jamaica,” I told her. “This is the home of rum! How about something along that line?”
“For you,” I told Pat, “if you’re more in the mood for something straight, I would recommend some of Jamaica’s finest, Appleton Black.”
“For you,” I told Ellen, “I can make you anything you’d like.”
Pat agreed to try the Appleton, while Eileen asked for a Cuba Libre’.
“Ahh. Rum & Coke, with a lime,” I teased. “Being adventurous while on vacation, are we?”
She shot daggers at me with her eyes while I asked Debbie and Christine what they were drinking.
They both replied that they wanted the same thing that I made them earlier, and I started mixing up the drinks.
I took care of the older ladies first, and as I handed Debbie and Christine theirs, Pat blurted out loudly, “Make sure you don’t mix their drinks up! Christine is pregnant and can’t drink!”
Debbie sighed, and Christine turned red as I gave them their drinks.
“Not a problem,” I replied. “Although, I’m not too sure that Miss Christine wanted the entire resort to know that she is pregnant.”
Debbie and Christine both smiled at me, as Pat replied with, “What? I was just making sure!”
As the evening wore on, I listened and talked with the ladies and discovered quite the family dynamic.
By 10:00, Pat and Ellen were quite buzzed, and decided to go sleep it off. Christine was tired, and also said her good nights, prompting Ellen and Pat to ask Debbie if she was coming along.
Debbie told them that she wanted to stay, and would be along soon. When her mother looked at her questioningly, Debbie replied, looking at me, “I think I’ll be safe here, won’t I?”
“Absolutely,” I told her. “I’ll make sure that you get back to your room safely.”
Ellen shot me another look, and then the three women walked off.
“Thank God they left!” Debbie said.
“Isn’t family fun?” I joked.
“You have no idea,” she sighed. “So, what’s your story?” she asked.
“Me?” I replied. “I have no story. I’m just here.”
“Bullshit,” she laughed. “You don’t ‘just’ work here, do you? You’ve got something to do with management.”
Smiling at her, I replied, “Yeah, you could say that.”
“So? You’re the manager?”
“Yeah, you could say that,” I told her.
“Is that your only answer? ‘You could say that?’,” she laughed.
“Yeah, you could say that,” I teased, smiling at her.
I was getting drawn in to Debbie’s smile as we continued talking, and I kept making her more drinks.
As the night wore on, Debbie told me that the reason behind the vacation was for Christine to get over her boyfriend’s leaving her when he found out about the baby, and for Debbie to get away from her husband for a while. When the two older women heard about the vacation, they invited themselves along, all on Debbie’s dime.
“As I said, you’ve gotta love family,” I told her, raising my glass in a toast.
“So, you don’t have family issues like that?” she asked.
“Honestly, I haven’t heard a word from my family since I came down here,” I told her, avoiding the details.
“Do you live here full time?” she asked.
“No, I still have my place back home, in Chicago,” I replied.
“Really?” she asked. “I was born in Chicago. I live in Wisconsin now, though.”
“Cool. A cheese-head,” I teased.
“Oh yeah!” she replied. “Go Pack!”
“Oh, geez!” I laughed at her reference to the Wisconsin/Chicago rivalry.
“So, I’ve been telling you all about me. Are you going to tell me anything about yourself?” she asked as I handed her what she said was going to be her last drink of the night.
“Maybe,” I joked. “Ask me a question, and see if I’ll answer it.”
“Ok, what is the real story behind you being here?” she asked.
“I, tophane escort um, help run the place,” I told her.
“Uh huh,” she replied, smiling at me. “Something tells me that there’s more to it than that.”
“I’m sure I don’t know WHAT you’re talking about!” I told her, smiling back at her.
“So, that’s all you’re going to tell me?” she asked a couple of seconds later.
“Well, that’s all you asked,” I said.
Debbie sighed, and put her empty glass down on the bar.
“Well, I think that’s it for me tonight,” she said softly.
“Ok,” I replied. “I’ll walk you back to your villa.”
“I think I can find my way back,” she said, standing up.
Seeing her wobble as her feet hit the ground, I stepped out from behind the bar.
“I told you that I would get you back safely,” I told her, offering her my arm, “and I try to never break a promise, especially to a beautiful lady.”
Debbie looked up at me, and blushed again.
“It’s been a long time since anyone other than my kids told me I was beautiful,” she said softly.
“Well, now that is just wrong,” I told her as I led her down the path to her villa. “Your husband never tells you that?”
“My husband has … other priorities,” she said softly. “Like work, the waitress at the diner he goes to every morning for breakfast…”
“Wow,” I replied. “That is just wrong on so many levels!”
A couple of minutes later, I had Debbie at her door.
“Thank you for making sure I got home safe and sound,” she said, still holding tightly to my arm.
“It was my pleasure,” I assured her.
As I looked down at her, I saw something in her eyes that made me want to lean in and kiss her, but I fought off the urge and walked back toward the pool area to clean up, and then go to bed myself.
The next couple of days, I had Rita and Valentine arrange tours of the coffee plantations, the rum distillery, and the usual tourist places for the women. To my complete lack of surprise, the two older women declined to go on most of the trips, staying behind at sitting by the pool, smoking cigarettes and complaining instead.
In the evenings, after dinner, we all sat around the pool and bar, as I made Debbie different cocktails, giving her daughter virgin copies, and Ellen stuck with her Cuba Libre’s, with Pat either trying what I made for Debbie or sticking with straight rum.
Most nights, the conversations were filled with the older ladies complaining about how the food was too spicy, even though I made sure that Betsy used no hot peppers or spices at all, or how bored they were. I knew that they were starting to irritate the staff, and I tried my best to soothe their nerves.
After the others would go to bed, Debbie and I would sit and talk. At one point, I offered to take Debbie on a “special” private tour of the resort, telling her that there were some things that had to be experienced at night. After sitting in silence for a second, she promised that she would think about it.
Finally, on their last night, after the others all went off to bed a bit earlier than usual, due to an early flight back home, Debbie and I stayed up having a few more drinks.
That night, she was wearing a flowery halter-top sun dress, with her beautiful legs leading down to a dressy pair of sandals. I was admittedly having a hard time concentrating on the conversation as I looked her up and down.
“Does that offer for the private tour still stand?” she asked.
“Of course,” I replied, offering her my arm as I stood.
As she took my arm, holding on tightly, I led her down the path toward my house, and took the detour to the beach.
When we reached the beach a few minutes later, I told her that she might want to take her sandals off so that she didn’t ruin them, and also to make walking easier in the wet sand.
As she held on to my arm, I watched as she leaned over and slipped her sandals off, also giving me a nice view down the front of her dress at her braless breasts. As she stood, holding her sandals, I told her they would be safe on a flat rock at the path’s end.
I then led her further down the beach, to a secluded cove that I found shortly after I moved out there.
“Wow,” she said, as we walked under a natural canopy formed by trees covering the area. “This is nice!”
“It is,” I agreed. “I love coming out here when I just want to be alone. It’s very peaceful, just sitting here listening to the ocean.”
“I bet,” she replied.
I led her to a spot toward the back, cut into an old rock wall by the water over time, for us to sit at. I sat down first, and Debbie joined me, sitting with her back to me.
“This is really nice,” she said, leaning against me. I wrapped my arms around her shoulders, and she raised her hands and held on to my arms.
“It sure is,” I replied, holding her tightly.
I didn’t know whether she was referring more to the setting, or sitting there with me, but I wasn’t going to push the issue.
We sat there silently, just looking topkapı escort out and listening to the sounds of the ocean for a while. I could feel her body relax as we sat there, my arms around her.
A few minutes later, it started raining softly. Debbie looked up, and I told her not to worry, as the trees above us would keep us dry.
“Are you sure?” she asked, looking up at the canopy. “It’s starting to come down a little heavier.”
“I’m sure,” I assured her. “I’ve been out here in a heavy downpour, smoking a cigar and having a drink, and stayed completely dry.”
“Oh, yeah?” she asked. “And how many other women have you brought down here?”
“You’re the only one,” I told her.
“Ok,” she sighed, leaning back into me. “I’ll believe you.”
I began to softly stroking her arms, and soon she had placed her hand on my thigh and she started stroking my leg.
At one point, she moved her arm, and my hand fell to her side. I felt, and heard, her sigh, and I slid my hand under her arm and softly stroked her side.
Before I knew what I was doing, my fingers were on the side of her breast, and she inhaled sharply.
“Oh geez!” I said, moving my hand away quickly. “I’m sorry!”
Wordlessly, Debbie reached up and wrapped her fingers around my wrist. To my surprise, she brought my hand back up to the side of her breast.
“Don’t be,” she said softly. “I’m not.”
I turned my head slightly, looking at the side of her face, and gently slipped my fingers inside the halter of her dress. I cupped her breast as I leaned in and softly kissed the side of her neck, just below her ear.
Debbie gasped, and I felt her hand tighten on my thigh at the same time that I felt her nipple stiffen under my fingertips.
She suddenly sat up, and I thought that I had gone too far. Before I could say anything, though, Debbie turned to face me.
We sat there for a moment, looking into each other’s eyes, and I reached out and slowly stroked her bare shoulders and arms.
I felt, as well as heard, her sigh, and I saw the look in her eyes.
“Kiss me,” she whispered.
Leaning in, I put my hands on her face. As I leaned in to her, our lips touched.
After a couple of seconds, she leaned back and looked at me.
I slid my hands down to her waist and pulled her in to me, and we kissed again, more intensely this time as her legs draped across mine.
As I slid my hands up her back, and across her back, I could feel her breasts crushed against my chest.
Our kiss became even more passionate, and I could feel a thin layer of perspiration begin to build on her bare skin.
Pulling my lips from hers, I looked deeply into her eyes.
“Let’s go,” I whispered, as I slid my hands down to her ass, cupping her cheeks and standing.
Debbie whimpered softly as I rose, holding her body tightly to mine.
Reluctantly, I let her lower her legs, until she was standing.
With a look of animalistic heat, Debbie pushed me against the rock wall and stepped into me.
I moaned softly as I felt her lips on my neck, and then on my chest as she began to unbutton my shirt.
I slid my hands down her back, and then up under her dress.
To my surprise, my hands were soon on her bare ass.
“Did you forget something?” I whispered in her ear.
“Well, weren’t you the one who said ‘We’re on vacation. There are no rules,’?” she asked.
“Why, yes, I seem to remember saying something like that,” I chuckled.
“Ok, then. Are you complaining?” she asked as she continued to kiss my chest.
“No ma’am,” I breathed.
I pulled her face back up to me and kissed her again. I slowly started sliding my fingertips across her ass, and she slid one hand in between us and wrapped her fingers around the bulge in my pants.
We both moaned, as she squeezed my hard shaft, and my fingers reached down around her ass. I teased her tight little asshole with my fingertip, and then continued to her wet slit.
“I want this,” she whispered, squeezing and pulling on my pole as she pulled her lips from my neck.
“Mmmm!” I moaned, moving her hand. “Not yet!”
Keeping my fingers teasing her hot pussy, I quickly spun us around, and placed her up against the cool rocks.
I slid my hand around to her front, keeping it under her dress.
I leaned in and kissed her again, slowly dragging my hand through her sparse hairs above her shaven slit. I lightly teased her clit, and then slid one finger past her swollen lips, and into her wet pussy.
Debbie gasped loudly, and I felt her body shake. As she began to moan into my mouth, her hips started moving against my hand, and I slid another finger inside her.
“Oh god!” she softly gasped, squeezing my arms.
I felt her hand slide back down to my cock, and start to lower my zipper.
“Patience,” I whisper to her, as I moved her hand again.
I then moved my thumb up to her clit as I slid my fingers in and out of her hot, wet pussy.
I felt her breathing get even heavier, and she started to shake just a little. “Oh, god!” she gasped, squeezing my arms harder.
I quickly slid my fingers out of her panties. Debbie’s eyes opened, and she watched me as I brought one of my fingers, coated in her juices, up to my lips.
I heard her moan again as she watched me slide one finger into my mouth, tasting her.
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