Jackie’s Problem

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Şub 20, 2023 // By:analsex // No Comment

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Sitting out on the back deck I do not always hear the doorbell when it rings. I should probably fix that problem some day since I spend so much time out here enjoying the view and sun. Then again I do not get many unexpected guests.

I live on the outskirts of town on a large bluff. The back of my home faces the south towards the city and the view is spectacular. The view was the main reason I choose this spot to build, that and it is quiet and peaceful without a neighbor within a mile. The large expansive deck and patio is where I spend most of my nights and some days as I work from home.

It is Friday, midafternoon, the sun high in the sky with a temperature of nearly 80 degrees. It is very pleasant out here sitting under the covered area of the deck. With iced tea in hand I was just getting ready to light the first cigar of the day. I save my cigar time until after my work day is complete so that I can enjoy the time it takes to really appreciate the craftsmanship.

I moistened the wrap, clipped the end and placed the cigar to my lips to light. Clyde, my German Shepard, lifted his head, ears alert. Being that I just walked outside minutes ago, I did not see the car drive up the private road. Clyde rose, walked to the door, and looked back at me. Looking at Clyde I asked, “What is it boy?” With that he pranced into the house towards the front door. With a sigh I followed.

Sure enough the doorbell rang again. “Good boy Clyde,” I said as I rubbed between his ears.

I wasn’t expecting company; I was dressed in only a pair of linen shorts. The bell rang again, as if somebody was impatient. I walked a little faster and opened it.

“I am so sorry, Mr. Walsh,” breathed an excited Jaclyn or Jackie as she preferred.

Jackie is my housekeeper. She normally arrives on Thursdays, which she had done just the day before, to clean my home. She works for a service in town and she was assigned my place to clean once a week. She attends the local university and I believe she is in her second year. I am not sure on this point since I never asked; she rarely opens up about her personal life. She usually shows up, lets herself in, does her work and is off.

“Jackie, what’s the matter?” I said. Her makeup was smudged around her eyes as if she had been crying.

“Mr. Walsh, can I come in and talk with you?” Jackie asked while looking down at her feet.

“Sure Jackie, I was just out on the back deck when you arrived. Would you like something to drink, lemonade, iced tea, water?”

“Do you have anything stronger Mr. Walsh? I sure could use something to calm my nerves.”

“Sure thing Jackie, help yourself, you know where everything is. I will be out back. Come and join me there.”

Jackie is a cute, petite girl, standing probably no more than 5’2″ and 100 pounds. She has long raven hair, big brown eyes, a button nose and full reddish lips. Her hips flair out just right for her frame, her legs are muscular but not big and her breasts are probably a large B cup.

Jackie poured herself a straight shot of bourbon, quickly drank it down and poured another. With the second glass poured she walked out to the deck where I was sitting. She already looked much calmer. Sitting across from me she gazed across the valley over the city. She obviously had something on her mind and it must be heavy on her shoulders considering she drove out here to talk with me. I hardly know the girl.

Giving her some time I took a sip of my tea and decided to light that cigar that I was getting ready to enjoy. With the cigar lit I sank into my chair as if Jackie wasn’t even there. I gazed out across the city, too.

“It’s very beautiful up here,” Jackie said breaking the silence.

“Yes it is,” I answered. “This is the reason I picked this spot for my home.”

“Do you get lonely up here all by yourself?” said Jackie, “I mean you hardly ever leave especially since you work here to.”

“Oh, I get to town a few times a week. I meet with clients, shop for groceries, go out to dinner,” I responded.

“Yes, I suppose you do,” Jackie contemplated.

More silence ensued. Clyde was lying next to Jackie and I was puffing on my cigar. I was in no hurry before Jackie arrived; I guess I shouldn’t be in a hurry now. I was more curious than anything. I was sure she had a good reason for coming, but looking at her slightly disheveled state I was not going to press, at least not yet.

After about fifteen minutes I rose from my chair, grabbed both glasses and walked into the house. From the kitchen I could see Jackie sitting, gazing out over the city. I would assume with whatever was on her mind see really didn’t see anything. Jackie’s feet were stretched out in front of her, her feet were bare. I could see the week old polish on her toes, some shade of red and starting to peel. Her legs were tan and I could make out all the muscles up her calves and over her thighs. They were twitching slightly; apparently she was unable to relax. From this angle I could not see her short denim shorts. She looked naked from the waist down. Beylikdüzü escort My mind wandered with that observation. I wondered why I never noticed those legs before. Probably because she worked and then left, always wearing appropriate clothing. The service must have a loose dress code, no provocative clothing.

Shaking my head clear I reached for a new glass for me, walked to the fridge and tumbled a couple of cubes of ice in each glass. I walked over to the liquor cabinet, grabbed the bourbon and poured three fingers each.

I paused again on my way out the door and gazed once more at Jackie sitting there. The angle this time was different. Jackie’s long hair cascaded across the back of the chair, the strap of her tank top invisible making her shoulders appear bare. Her breasts from this angle looked larger than I am sure they are and her nipple was erect. “Curious,” I thought, “she must not be wearing a bra.”

I stepped out and placed a refilled glass at her side and then settled into my own chair. Again silence.

I could only be so patient so I decided to give her only a few more minutes before I spoke.

Jackie took a small taste of the bourbon, set down the glass and turned to me. I could see her out of the corner of my eye, but I did not turn.

“Mr. Walsh,” said Jackie.

I turned to look at her. Her big brown doe eyes were looking directly into mine. “Jackie, since you are here for reasons other than work, call me Mike.”

“OK … Mike, I have a serious problem and I needed to run. I didn’t know where to go, but I thought of you and this house out of town. I thought it might be safe until I figure things out.”

“Safe here, how long are you planning on staying?” I asked.

“Well,” Jackie paused for a long moment, “I haven’t thought that far ahead yet.”

“Jackie, on a scale of one to ten, how serious is this problem of yours?”

Without hesitation Jackie said, “Eleven.”

“That serious huh?” I was young once and I remember the serious problems I encountered. In looking back at my “elevens” they were really no more than maybe a three or four. “I can see in your face that the wheels in your head are spinning. Why don’t you stay here for the night and if you are up to it in the morning we can talk more.”

Jackie’s shoulders dropped, it looked as if a weight had been lifted and she could somewhat relax. “Thank you Mike, I really could use a night to think.”

Clyde, sitting next to Jackie, lifted his ears and he sat his chin on her thigh. Dogs must know more of what is going on than we give them credit for. Jackie smiled at him and wrapped her arms around his neck to give him a big squeeze. I think Clyde was smiling at me.

I would be smiling too.

Jackie stood, excused herself into the house, as I sank back into my chair. I grabbed my cigar in my right hand and my bourbon in my left and contemplated the previous events.

“What could be so serious to a girl only twenty … how old was she?”

“Was she wearing a bra under that tank top?”

“Where is her family, did she live alone here in town?”

“I wonder if she shaves, trims or is au naturel.”

“Is she having boyfriend troubles?”

“Of the $100 a week I pay the cleaning service how much does Jackie get?”

Breaking me out of my thought Jackie stood in the doorway to the house. “Mike, I am making dinner tonight. What should we have? I didn’t look in the kitchen; I didn’t want you thinking I was snooping.”

“Jackie, I haven’t thought that far ahead, I usually go into town on Fridays a get a bite at McGruder’s.”

Jackie’s eyes dropped to the floor, “Ok, you mind if I find a little something for me here?”

“Jackie, why don’t you join me?”

“Oh no, I can’t go back into town, not tonight.”

“Well then, I guess we can browse the kitchen and see what we have. There won’t be much. I usually drive to town on Saturday to grocery shop.”

“Mike, you stay there. I will see what to make.” With that Jackie turned and disappeared once again.

Fifteen minutes later Jackie reappeared. She had the bottle of bourbon in her hand and refreshed my glass. “I found a couple of steaks in the freezer, one potato I will bake and we can split, and enough for a small salad. Does that sound all right with you?”

“Delicious. Everything is better when prepared for you.”

“The steaks will take a little while to thaw, would you mind if I took a shower while we wait? “

“Not at all,” I said, “make yourself at home tonight. You probably know more than me about where everything is.”

With that she pranced into the house again. She does look like she feels better; again “elevens” are many times a three or four.

Forty-five minutes later I heard Jackie in the kitchen. I just finished the last of my bourbon and my cigar. Moments later she appeared and walked to the edge of the deck. She was wearing one of my t-shirts. She placed her arms on the railing, lifted her heals and bent at the waist as she leaned forward. Her calves became taut and the bottom Beylikdüzü escort of the t-shirt rose up her thighs. The way she was angled and the position of the sun Jackie was silhouetted in such a way I could see the outline of her legs where they joined in paradise. I could not see her sex, but I could definitely imagine. She inhaled a deep breath and turned.

My eyes were still at the level of her pussy, she caught me looking. With the light on her back my previous question still went unanswered. I glanced up slowly to her breasts, her nipples visible under the light cotton. Father up her lips were slightly parted, a small smile formed. Her eyes were expressive, definitely not the girl that walked into my house earlier this afternoon. The make-up smudges were gone; her face was clean and without makeup. Jackie was absolutely gorgeous.

I smiled back. “You look like you feel better.”

“I do, thank you. I will start dinner in a few minutes; I hope you don’t mind if I borrowed a shirt. I didn’t bring any other clothes. I put mine in the wash so they would be clean for tomorrow.”

“Not at all Jackie, in fact it looks better on you than it could ever look on me.”

Dinner was wonderful and simple; the red wine Jackie picked went well with the steak. The conversation was light. Jackie seemed to have forgotten what brought her here. She cleaned up for us and again we found ourselves on the deck. The sun was down and the lights below illuminated the city. The sky was clear and the temperature dropped into the low seventies. I could see that Jackie’s nipples were hard under the t-shirt. Her legs were stretched out in front of her and slightly parted. The result was that the t-shirt was high on her thighs. If I was in front of her looking on I am sure the view would be much better than the city below us.

A quiet hour later Jackie stood, stretched and retired for the night.

Soon after I went to the master bedroom, stripped naked and settled on top of the covers. My hand rested on my cock seemingly on its own. My mind flashed across the afternoon, Jackie’s watery eyes when she first arrived, her long muscular legs, her nipples poking against the thin cotton, the sun shining through the t-shirt, the silhouette of her sex. Before I knew it my cock exploded, cum spurting up to my chest, pooling on my stomach and dripping down my hand.

I went to the bathroom, cleaned up, returned to bed and was fast asleep.

Morning came with the smell of fresh coffee. Looking through the kitchen window I saw Jackie leaning against the railing looking down the valley. The sun wasn’t in the right position to get the same view as the day before, but I am positive my ass doesn’t look that good while wearing my own t-shirt. I poured a cup of coffee. I was wearing pajama pants, my cock semi-erect and swaying as I walked. Jackie turned and looked then turned back to the view.

I was sitting now, still admiring my own new view and said, “Jackie, are you ready to talk?”

She turned again, walked to the chair and sat.

With a deep breath, then an exhale, it all came out.

“Yesterday morning I drove 200 miles to this town across the state line to pick up some drugs and deliver them to another town. While driving down the highway I felt like I was being followed and pulled into a busy rest area. Freaked out I took the drugs into the bathroom and flushed them down the toilet.

I came back here and while I was pacing around my apartment my phone rang about a half an hour after I was supposed to show. I didn’t answer; they hung up and called again, over and over. Since I didn’t answer any of the calls I got a text which said, **Where are my fucking drugs BITCH**. I dropped the phone and started crying then the phone beeped again. Another text, **You have one hour or you are dead**. That was yesterday, I haven’t heard back.

I ran out of my apartment crying, got into my car and drove around for about an hour. Then I realized that the place I picked up the drugs would know my car. I freaked again, not knowing where to go I drove my car straight here. It is way out of the way, they couldn’t possibly know where I am. I am so sorry, I shouldn’t have come here. I will go get my clothes and leave.”

I don’t think she took a breath, it all came out so fast. I had questions.

“Jackie, first take a deep breath, then tell me where your keys are, I will park the car in the garage.”

With that I walked into the spare room, got the keys and promptly moved the car. I walked back into the house and back out to the deck. Jackie was curled up on the chair; her knees were to her chest, her feet flat on the chair, her head resting on top of her knees. From the way I approached I now knew the answer to my question, trimmed.

The way she was sitting made her fully exposed. I am not sure if she realized that her pussy was on full display or if she even cared. Her pussy lips were plump, but not from arousal, that was their natural state.

I turned around, walked back into the house and up to my room. I retrieved Escort Beylikdüzü a pair of boxer shorts and returned to the deck.

“Jackie, put these on.”

She looked up, embarrassed. Her cheeks did not turn red since they were already red from her story. She stood, turned away from me and slipped on the boxers. “Thank you,” she said and sat back down. “Mr. Walsh you have been very kind and I am sorry that I have bothered you. I don’t want you involved so I need to leave and figure this all out.”

I kneeled down in front of her and said, “Jaclyn,” I reached up and brushed the hair from her face. I could tell that her big brown eyes were getting ready to tear up. “Let me ask you some questions first, then let me see what I can do to help.”

I sat back down across from her and thought for a moment.

“Was this the first time you have done this?”

“Yes, I was desperate, my rent is due and I am really short on the money I need.”

I looked at her. “Have you asked your parents for help?”

She looked down at her feet; she is curled up in the same position as before but now the boxers are covering her. “I don’t have any parents. I was in and out of foster care since I was eight and I moved west when I got out of high school. After about three years I moved here and decided to try to go to college. I was tired of moving around, being homeless and afraid.”

“I see,” I said. “Have you told anyone else about this? How did you come across these people to run drugs for?”

“Well, I called a friend from the last place I lived and asked her if she knew of some quick work that I could do to make a few hundred dollars. She said she was still prostituting, but not on the street anymore; she was using the internet. I don’t want to do that again I said.”

“Again,” I said, apparently out loud though I meant to say that to myself.

Jackie looked away, her voice quieted a notch, “Yes, again. I am not proud that I did that, I needed to. I was on my own and needed to survive. I watched the girls around me get hooked on various drugs. I didn’t want that, that is why I was turned to foster care. My parents were addicts.”

“I am sorry to hear that, Jackie,” I said and I genuinely meant it.

She turned back to me, she was looking in my eyes, I think trying to read me. Her brown eyes were beautiful. I stared back. She smiled at me and said, “thank you Mr. Walsh.”

“No more Mr. Walsh, remember its Mike.”

“OK, Mike it is. Anyway my friend told me she was running drugs up the interstate and they pay her $300 a trip. I needed about $500 to pay my rent and buy some food, so I thought two trips would get me back on track. Since it is summer my student aid stopped until the fall term. The housekeeping agency doesn’t pay enough for me to live. Being a college town work is hard to find in the summer.”

That I can understand, about 20,000 students vacate the town for the summer. Tourism brings in a few people during the summer with all of the outdoor activities but those jobs are hard to come by.

“Do these people know where to find you? Do they know where you live here?”

“I don’t think they know unless my friend told them. She doesn’t know exactly where I live but she does know where I go to school.”

“Jackie, can I have your phone?”

Jackie got up and went into the house. She retrieved her phone and brought it back. I looked at the texts, nothing new.

I started typing on her phone, she looked a little scared.

**I don’t have the drugs anymore, I was being followed and flushed them**

We waited, but not for long. A text came back.

I looked at Jackie, “Is this your everyday phone?”


I opened the new text and read it. **BITCH I am at your school I only had to hit Caitlyn five times to get her to talk I will find you**

I looked back at Jackie, she was standing behind me. She wasn’t really crying but tears were running down her cheeks. Her hands were shaking a little. She reached around me; her head rested on my shoulder and she said, “I am scared.”

I turned and started typing again, **what can I do to make this right**

Moments later the phone beeped, then beeped again.

**I want my drugs + $2k or $8k plus $2k for my trouble**

**or I want your ass you are going to work it off**

“Do you have any idea who this guy is?” I asked.

Jackie shook her head.

I put the phone down. Jackie walked over to the railing. She looked sick.

“Well we only have one choice to get you out of this,” I said.

Jackie turned, “I don’t have enough money to pay my rent, the drugs are gone, so the only choice is to run.”

“Well I wasn’t thinking that, so I guess you have two choices.”

Jackie didn’t smile, instead she ran into the house and into the guest room.

I slowly followed. The door was ajar so I walked in. “Oh, sorry,” I said. I just as quickly backed up and closed the door.

Jackie was naked, from the angle I was at in the door way I could only see her from behind. Her long hair cascaded forward as she was bent over putting on her panties. Her right leg was bent and raised off the ground as she put her foot through to one side, her pussy on full display once again. Leaning forward her breasts swung slightly as she moved. She was in a hurry.

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