The Caretaker - Cover

The Caretaker

Copyright© 2021 by C...B

Chapter 5: Fun memories.

Fiction Sex Story: Chapter 5: Fun memories. - Dylan Clark's life is going nowhere fast. With his marriage a failure and his prospects for the future grim, he realizes that he needs to make some drastic and serious changes. He takes a mysterious job hoping to get his life back on track and moving forward again. Instead of the hoped-for positive changes, he finds himself caught in a deadly web of mystery and intrigue. What the hell has he gotten himself into and is there any way for him to escape?

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Consensual   Mind Control   Heterosexual   Fiction   Mystery   Restart   Workplace   White Male   White Female   Oriental Female   Hispanic Female   Anal Sex   Cream Pie   Fisting   Oral Sex   Voyeurism  

Near Present day – October 16th
Montana Compound (assumed) – second tour

I smiled as I thought about that visit from Liz. I had to admit the health care plan here was great. Although Liz had said that we might meet again, that had yet to happen. When I had gotten my second medical exam during my second two-month work period, the exam had been provided by a male medic. He had not offered, and I was not hard up enough to accept if he had.

I drifted back into recollecting to my first work period. After Liz’s visit the following three weeks were more of the normal routine. I had just another week until my first month’s leave and I figured that I would have to hold out until that vacation for any hope of female companionship. I had guessed wrong...


Six months ago, May 1st.
Montana Compound (assumed) - first tour
(Just days before the beginning of the first month-long leave period)

I came awake early before dawn three days before I was scheduled to begin my first month-long leave by a movement on my bed. I had woken a few hours earlier by the sound of a helicopter arriving but I had quickly fallen back to sleep. I opened my blurry eyes to see that the lights out in the mudroom were on. I also made out in the darkness of my room a figure sitting on the side of my bed. I looked over at my clock and saw that it was just after four am.

“I am sorry to wake you so early Dylan, but my schedule got moved up and I can only stay another few hours,” I heard a woman say.

“Who are you?” I asked with a croak. I could now make out that the woman was older, at least ten years older than me, maybe even fifteen. It was still somewhat dark in my room, but I could see that she had short graying hair and was wearing glasses. She was not obese but had the plump look and extra curves common to women old enough to be grandmothers. She was dressed neatly in a blouse and dark slacks.

“My name is Mrs. King, but I’m called Angel. I’m a travel coordinator and scheduler for the organization. I’m here to discuss your upcoming leave. Why don’t you hop in the shower and then when you are fully awake, we can discuss your options and plans,” she said.

I just nodded and sat up. I could smell and hear the coffee percolating in the kitchen. Angel had apparently hit the button on the already prepared machine. Before I got out of bed I remembered I had no robe nearby. I looked to Angel to warn her but I could see her already smiling.

“Oh, don’t worry about an old lady like me Dylan, I’ve seen it all.”

So be it. I stood up in just my underwear. My cock was still semi-hard from the good dream I must have been having. I entered the bathroom and found Angel was right behind me.

“We might as well talk as you shower. You don’t mind do you?” she asked, still giving me that small smile.

What the hell ... when in Rome and all that. If she was not going to be offended, then I was not going to be shy. I ditched my briefs and stood over the toilet to take a leak. Angel moved right around and was not shy about getting a good look.

“Oh Dylan! That is a nice piece of equipment you have there. A bit larger than my husband’s.”

“You’re married?” I asked.

“Was. Bob had a heart attack eight years ago,” she said matter-of-factly.

“I’m so sorry,” I said with sympathy. I also noted that our conversation was pretty bizarre considering that I was standing there still pissing like a race horse.

“Thank you. I miss him but I’ve gotten over the worst of the loss. You know, I’ve been stuck flying and traveling for over twenty hours. I’m feeling a bit grungy. Maybe I’ll join you in your big shower and we can wash each other’s back.”

She had not even finished talking before she was unbuttoning her blouse. I just finished up and shook my cock dry. She folded her blouse neatly and set it on the vanity. Next, she popped her bra open and her fully mature tits popped free. They sagged a bit but were surprisingly firm. Her nipples were large, pink and hard.

She paused and asked, “You don’t mind, do you? You remote location guys are always a little ... backed up, if you know what I mean.”

I just smiled and shook my head. Now topless, Angel lowered the toilet lid and took a seat. She grabbed my hips and pulled my manhood towards her mouth. She rubbed her face along my stiff pecker and inhaled deeply. I had masturbated last night and I was sure she could smell traces of my semen.

“Oh, I love the smell of a man,” she said with her eyes closed.

The few drops of urine still on the tip of my pecker never even slowed her down as she engulfed my manhood. Her right hand wrapped around the base of my cock while her left pulled my ass towards her mouth in time with her strokes. Her lips formed a good suction seal while her tongue swirled around the head of my cock. She clearly had a well-honed technique, and I was powerless to stop her.

After a minute she had my cock as hard as a rock and tingling. She popped her mouth off for a moment.

“I hope you don’t mind that we are doing this here. My knees can’t take kneeling on the floor.”

I couldn’t care less where I got a blow job, as long as I got one. She resumed her suction and jacking. My hips started moving faster. She grabbed my hand with her left and brought it up to the back of her head. I got the hint and added my other hand and started moving her head forward and backward, fucking her mouth. Her right hand was still locked to the base of my cock which safely limited the depth I could reach. Another thirty seconds and my balls were tingling. I looked down and saw her eyes were shining as she stared up at me. I started to cum, and she sucked me in even harder, swallowing steadily.

“Gawd!” I yelled out as I struggled to keep my knees from buckling.

After my orgasm had subsided I helped Angel to stand and gave her a hug.

“That was great!” I said, “Thank you Angel.”

She just smiled and began to remove her slacks. I started the shower and got out an extra towel for her. She folded her pants and also set them on the vanity. I watched her remove her panties and noted that she was in pretty good shape. There were wrinkles and dimples but heck, I was starting to get a few of those myself. When she turned around I saw that her mound was large and plump. She was smooth shaven and this made her look like a big muffin.

I saw her take out a tube of something from her handbag and set it by the shower door. She also got out her toothbrush and set it on the vanity. I got in the shower first and started washing while she brushed her teeth. Soon, I felt her enter the shower behind me and start in on washing my back. She was free with her hands and was not bashful about washing my ass and reaching around to wash my cock and balls.

When I was done with my face and hair I switched places with her and let her stand under the water stream. I then started in on her back. I also fully washed and explored her ass and even got her moaning when I reached around and began washing and fingering her plump mound. I easily sank a few fingers inside her loose channel and found it warm and accommodating. I was able to jamb four full fingers inside her without no trouble. Angel had a large cunt and from her moans, my plunging fingers were appreciated.

She let me work away at her cunt while she somehow finished washing her hair. My attentions had her squirming around though and she was moaning every so often. My cock had started to harden when she finally turned around and gave me a deep kiss. We hugged as our tongues tangled and I felt her reach down and begin stroking my cock vigorously. Soon I was fully erect again. She pulled away a bit.

“I’d love for you to fuck me stud but I’m afraid that five kids have left me a bit loose as you surely have already noticed. Fortunately, I have a better option that I think you will love.”

She reached out of the shower and retrieved the tube that she had left on the back of the toilet. I saw that it was a small tube of lube and she proceeded to spread a big dollop on my cock and rub it around my shaft. She squeezed out a second gob and I watched her reach around and work the lube into her ass. She turned around and bent over, grabbing the movable shower head bar to support herself.

“Mount up stud. My ass is still plenty tight.”

It had been almost two decades since I had taken a woman in the ass but I was definitely game. First, I eased my middle finger into her rosebud. She squirmed and moaned while her anus tried to spasm and expel my finger. Finally, I felt her relax and release, so I added another digit, working them both around and spreading the lube deeper. She squirmed more and reached one of her hands into her plump gash to start sawing in and out of her cunt while diddling her clit.

“Shove that big cock up my ass Dylan. I’m ready for you!” Angel said.

I fisted my cock a few times to get it fully rock hard and lined up the head with Angels rear opening. I applied steady pressure expanding her rosebud until the head finally popped in. She hissed and I held off moving for a few seconds. Finally, her ass relaxed some and I began to very slowly bury myself deep into her bowels. Angel pushed back until I was embedded as deep as I could go.

I began to slide in and out, taking full deep strokes each time. The shower water ran over her back and was trapped between our bodies when my hips met her plump ass. Her ass was tight and felt very nice around my shaft. I could feel her clenching her muscles to increase both our pleasure. She was moaning constantly as I began to pump in and out faster.

I surprised myself when I felt my orgasm building quickly. I had just come from her blowjob not ten minutes before and I thought I would last a lot longer. But the combination of taking her taboo orifice, her loud moaning, and the thrusting and clenching action of her ass had me fully turned on. I took hold of her hips with both hands and began to slam her ass as hard as I could.

“Yes! You young stud, give it to me hard!” she grunted out.

I felt her ass clamping down as she started to shudder. This brought me off and I came, jetting a much smaller load up her ass then I had recently shot down her throat. She started to wobble a bit and I reached down to help hold her up. I slowed my thrusting and pulled her up fully, hugging her big floppy tits from behind. My cock softened but did not slide out of her ass for nearly two minutes until we had caught up on our breathing. Finally, my spent and shrunken rod popped out of her with a wet plop.

“That was great! You are a real man Dylan.”

“My pleasure ma’am, anytime.”

We washed each other up again. I was glad to see that there not much of a mess at all. After the shower, I did give her some private time in the bathroom so she could flush herself of my spend. She had also found the hair dryer stored in the vanity drawer which I never used.

While she finished up, I just got dressed in my bedroom and shook my head at the crazy situation I was in. Who would have imagined that my sleep would have been interrupted by a stranger and then not fifteen minutes later I’d be enjoying a blowjob followed by anal sex. I had to admit, it was a hell of a good icebreaker though and made our talk which followed much more relaxed and informal.

After we finished a cup of coffee each Angel got down to business. First, we went over my impressions of my first two months. She wanted to know what I had struggled with or where they should have provided more information. I assumed that since this had been my first work shift that they had wanted more information on how I was adapting to the situation.

Next she carefully probed into my feelings on the lack of knowledge and background of where I was and why I was here. I had gotten used to the scant information and mystery and had settled down to just do the job without wondering the why behind it. She apparently needed to hear me express that.

Finally, she delved into the scheduling of my leave and how I was to spend the first week. One tradeoff for having my leaves fully funded by the organization was that I had to use some of the time for supplemental training. I was surprised when she retrieved a passport from her travel bag. It was for me.

“You will be doing ten days of instructional training near Rio de Janerio, Brazil. I understand that you will be learning basic concrete and rebar techniques, some structural steel welding and the assembly of pre-engineered metal buildings. Your next two-month labor period will involve a bit of new construction I am afraid. The location will be isolated and extremely remote so pay attention to the safety training that is given along with your other instructions.” She paused to stare at me sternly from above her glasses.

“Yes ma’am,” I said while nodding earnestly.

She smiled and continued, “Seriously. You do not want to be injured during your next assignment. Medical care will be extremely limited and serious injuries will likely be fatal.”

She paused a bit and then continued. “Now, after the ten days in which you will be busy learning new skills, I have slotted you in for four days at Praia do Flamengo. This is a nice little beach area south of the city. I have arranged a small seaside apartment for you. I am sure you will get to exercise that wonderful cock of yours with the tourist or local girls. Just be sure to use protection. We like our staff to remain clean.” She again paused to stare at me over her glasses until I nodded back.

“Finally, how do you feel about an ocean cruise for the last two weeks of your leave? Note that I am referring to a private vessel rather than a large, crowded tourist boat.”

I thought for a moment and decided that would be fine. “That sounds great! Sign me up.”

“Good! You are now signed up.” Now, I’m sorry for this gotcha, but the yacht is what is known as an ‘expedition yacht’. What this means is that it is more rugged and utilitarian then the fancy yachts you might have seen on TV cruising the Med. This boat is designed to travel for weeks or months to and around some of the more remote areas of the world.”

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