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The Woodlands Assisted Care (Chapter 1)

This is a story of the promiscuous women, sexual encounters and adventures that I had with the worke
How It all started (Chapter 1)

My name is Tom and these events happened several years ago when I worked with a friend of mine who did rental management and property maintenance. Most of the guys that already worked for him were rather young and inexperienced. He was happy to have me on board, because I had a lot of remodeling, construction and management experience.

At the time, I was a 42 year old divorcee. I was 5’ 7” in pretty good shape and although no one would ever mistake me for Channing Tatum, we have similar body types. Of course minus the “six pack” for me although my stomach was still tight and flat.

Mark, my friend felt confident enough with me to take on complete jobs with a crew and as the sole contact point with some of the bigger clients. One day, he asked me to take Carl over to the “Woodlands” an assisted care facility that I hadn’t heard of. He told me that they were a regular contracted maintenance client. He said that Carl was familiar with them and would explain about the regular maintenance that we do.

He also said that they called specifically about repairing a damaged wall and painting all of the halls in the facility. He told me that I should see the manager, Karen about the repairs and painting.

As we were driving over to the Woodlands, Carl made the comment that I would like Karen very much and started laughing. I asked why he thought that and he told me that she was a ‘definite looker’, but she was married.

When we got there, Carl and I went to Karen’s office, but she had someone in there that sounded like a potential new client. After waiting outside of her office in the hallway for a few minutes, Carl said that he was going to go ahead and take care of changing out the burnt out light bulbs. He noticed a few when we were walking to the office. He said that was just one of the things that we did for our maintenance contract with them.

Carl left and I stood there waiting in the hallway for Karen to finish up. Finally after about 15 minutes, they both stood up and walked towards the open doorway of the office.

“Well, thanks again for considering us Mrs. Fields. Feel free to give me a call personally if you or your husband have any questions for the care of your mother.” Karen said to her as they walked into the hallway right beside me. She glanced over at me, smiled and then shook Mrs. Fields hand.

After Mrs. Fields walked away, Karen turned to me and asked, “May I help you?”

“I assume that you are Karen. If you are then yes, I hope you can help me. I’m Tom from Mark’s Maintenance and Mark sent me over to see you about some wall damage and painting?” I said.

“Oh wow! OK, You must be new. I’ve not seen you before. I’m sure I would have remembered you! Yes, I’m Karen. Nice to meet you.” she replied with a big grin on her face as she extended her hand out to me.

As we were shaking hands, a rather large woman in scrubs came up to us. She smiled at me and then turned to Karen and said, “Hey Karen, I really hate to ask, but something came up at home and I was wondering if it would be possible if I could leave an hour early today. I promise that I’ll make sure that all of the prep work is done for dinner before I leave, no matter what. Would that be OK?”

“I guess, Jill as long as all of the prep is actually done. You know how that night shift is. If it’s not all done, you know I’ll hear about it!” Karen replied.

“I promise. Believe me, you won’t hear any bitching from them about me! Well, at least not about the dinner prep being done today.” Jill said and laughed and then looked at me again and again smiled broadly.

I hadn’t even realized it, but Karen and I were still holding hands throughout their entire conversation. Jill looked down at our enclasped hands and then over to Karen and said, “...annnnd who is this?” smiling ear to ear looking right in my eyes.

Karen let go of my hand and cleared her throat and said, “Oh… ummm… yeah… This is Tom. Tom, this is Jill. Jill works in the kitchen.”

Jill smiled even more and stepped even closer in front of me and extended her hand out and said, “Nice to meet you, Tom. Really!”

I took her hand and shook it. “Nice to meet you too, Jill.” I couldn’t help notice at this point that Jill was pretty short and as most large women, she had absolutely huge tits. As I was looking down at her, I could see her more than ample cleavage and my cock started to react in my jeans.

I pulled my hand away from her and turned to look at Karen. “If you need anything, just ask, Tom. Seriously. Anything! Actually would you like some coffee? I’ll bring you some right now. How do you take it?” Jill said.

“Well, Tom. It looks like you’re going to be very popular around here. Jill doesn’t even offer ME coffee! Yes, Jill. I’d love a cup too. One sugar and plenty of cream. Thank you!” Karen said giving Jill a stern stare.

“OK, Karen. How about you, Tom? Lots of cream?” she said as she licked her lips.

“Um. No thank you, Jill. I will take coffee, but I take mine completely natural.” I said.

“OK then. I’ll make a note of that. Completely natural for Tom. I’ll be right back.” Jill said and started walking down the hall, but turned back to look at me halfway down.

“Ahemmm.” Karen cleared her throat again. “Why don’t we step into my office and discuss what I need from you. Oh my God. That didn’t come out right. I mean… well… ummm… let’s talk about the things that need to be done around here.” she continued and then stepped into her office.

I couldn’t help looking at her nice ass as she turned into her office. Karen was about 5’ 6” with a nice slender figure. She looked to be in her mid to late thirties. She was wearing a nice flower patterned dress that came about mid thigh and hugged her body nicely. She had nice toned legs, all of the right curves and a very nice set of breasts that were perfectly proportional to her body. She had shoulder length strawberry blonde hair and the cutest smile that you could ask for.

My cock continued to harden a little more as I followed her into the office. “Have a seat, Tom.” she said as she walked by the chair directly in front of her desk. She continued to walk around her desk. Thank God, as I didn’t want her to see my hardening cock.

I sat down and put my hands on my lap to cover myself. As Karen got around her desk and sat down facing me. She smiled nicely at me as she placed her hands on the desk.

I glanced down at her hands and noticed her engagement ring and wedding band combo. She then held her right hand over her left hand and said, “Yes, Tom. I’m married. Sorry about that.” and then tried to suppress a little giggle.

“Oh, no. I wasn’t looking at that.” I lied to her.

“OK, Tom. I didn’t notice that you didn’t have a wedding band either.” she said and then outright laughed. “Sorry, Tom. I couldn’t resist.” she continued on and then giggled some more.

I now noticed that I could clearly see that Karen’s nipples had become hard and were poking through her bra and the material of her dress. She also had a very nice cleavage. My cock had now become completely hard in my jeans and was aching.

Karen cleared her throat again and then said, “So. Umm… let’s see… So we have this wall in room 119. The plaster stuff started falling off a few weeks ago. I called Mark and as usual, he forgot about me. Since then Mr. Marshall, the occupant crashed his wheelchair into it. So now, there’s a big hole in the wall to boot. We had to move Mr. Marshall to another room temporarily. So, that’s why I called Mark again to get this taken care of. Then there’s the painting. I want to paint all of the hallways.”

“Here you go, dear!” Jill said interrupting Karen as she entered the office and handed me a coffee.

“And where’s mine?” Karen asked.

“Oh shit! I forgot yours. I’m sorry….” Jill started to reply.

“Oh my God. One good looking stud comes in the place and everything goes to hell in a hand basket!” Karen said. “Oh my God. Did I just say that out loud? Ooops!” she said, then covered her mouth with her hand and turned red in embarrassment.

“I’ll get your coffee right away, Karen. I’m so sorry.” Jill said and almost ran out of the room.

I took a sip of my coffee while looking Karen right in her red face.

“I’m so sorry, Tom. I can’t believe I said that. I… I… I don’t know what came over me.” Karen said, still red in embarrassment.

My cock was throbbing in my jeans and tenting them up. Jill came back in the office with Karen’s coffee. “Here you go, boss. I’m so sorry. I don’t know what I was thinking.” she said and placed the coffee on her desk as she stood right beside me.

She turned and looked down at me.

“Well, I think we both know what you were thinking about.” Karen said sarcastically and giggled.

“I have NO idea what you’re talking about, Karen.” Jill replied as she continued to look at me. “How’s your coffee, sweetheart?” she asked me as she reached down and placed her hand on thigh and started to rub it up and down.

I gulped and replied, “Fine. It’s fine.”

I looked back up into Jill’s face as I watched her eyes widen and she said, “Wow. Yes, it’s fine alright… VERY fine!” and then she ran her hand right over my hard cock once and pulled away. She winked at me and started walking to the door. When she got to the door she stopped and turned back around and said, “Let me know if you need anything, Tom. I do mean anything. Oh and by the way, I don’t know if you smoke or not, but we only have one smoking area. It’s outside the back door of my kitchen. I don’t smoke, but I DO enjoy a nice big, fat cigar every once in a while if you know what I mean.” she said and licked her lips, turned around and left.

“Well, do you want to see it, Tom?” Karen said.

I turned back around and looked at Karen. I had no idea what she was talking about as I felt some pre-cum ooze out my hard cock at this point.

“The wall. Do you want to take a look at it?” she said.

“Oh yeah. The wall. Yes. I need to see it.”

Karen giggled a little and then stood up. She walked around her desk as I stood up too. I took another sip of my coffee.

“Oh my God. Wow!” Karen suddenly said.

I looked at her as I brought the coffee cup down from my mouth and noticed she was looking right at my crotch. “Oh SHIT! I’m sorry, Karen. I just… umm…”

“Oh my God, Tom. You’ve got nothing to be sorry about. That’s for sure! Wow! I wish I could… Ummm. Oh my God. Wow! So... well, let’s take a look at it! Shall we?” she said as she continued staring right at my crotch. “Oh my God. The Walll! Let’s take a look at the wall.” she continued as she turned a bright red now.

“Yes. Let’s do that.” I replied.

We walked side by side down the long hallway chatting and sipping our coffee. We turned down another hallway. This place was much larger than it looked like from the front. Karen started telling me about her frustrations about how she felt like Mark wasn’t taking care of things. She started telling me about a number of other things that she had asked Mark to take care of over almost a year that still hadn’t been taken care of.

We finally got to room 119 and walked in. The door automatically closed behind us, just like they do in a hotel. We walked over to the corner where the damage was. I noticed that there were stains from the ceiling more than half way down to the floor. I suspected a water leak as the corner was actually formed into an outside corner as you would do to surround a vertical pipe.The hole in the wall had nothing to do with the water damage other than it was beside the damaged corner.

“Oh what a mess this is.” Karen said and she bent over and started to pick up a piece of drywall which immediately broke into three pieces. “Oh my Lord.” she said. She wiped her hands together and then turned around and went to the bathroom, She came back with the trash can from the bathroom.

She got down onto her knees and started picking up pieces of drywall and putting them into the trash can. I was inspecting the water damaged corner right beside her.

“I think you have a leaking pipe behind here and that’s what was causing the paint to peel off and the drywall to crumble. See those stains? Those are from water or some liquid.” I said.

She straightened up on her knees and looked up at me. My cock immediately swelled in my jeans as I looked at her now. As she was on her knees right in front of me, I could see right down her dress and almost to her nipples.

She hadn’t noticed as she was looking up toward the ceiling and my face. I pointed out the stains to her and said, “I think that we need to discover exactly what the issue is which would mean tearing part of the wall down to see the pipe behind it, instead of just repairing the wall.” I told her otherwise, the damage will most likely just keep happening.

I dropped my hands down to my side as I turned more towards her. “I’m sorry it’s not good news, Karen. Really.” I said as I continued looking down at her cleavage. My cock was throbbing and more pre-cum released again.

Karen sighed while looking in my eyes. “That figures. Nothing is ever easy. Oh well. I guess we need to do whatever we need to do.” she said and then lowered her gaze which was now my tented out jeans only inches in front of her face.

“Oh my God, Tom. That is not fair!” she said.


“Teasing me with that big, hard thing right in my face. I mean… How’s a gal supposed to resist that?” she said staring right at it.

“I’m sorry. I didn’t mean to. Besides, it’s not my fault.” I said in defense.

“What do you mean, it’s not your fault?”

“I mean, you’re the one teasing me with those big exposed tits, hard nipples on your knees in front of me like you’re ready to… ummm… well, you know!”

“Ready to… ummm… what, Tom?” she said now laughing.

“See. You’re the tease. You know what I’m talking about.” I said as my cock throbbed and then flexed in my jeans again.

“Oh, I am sooo NOT a tease, Tom!” she said and reached up and unzipped my fly.

“Oh God, Karen!”

“What?” she said as she unbuttoned my jeans and then grabbed the top of my jeans and started pulling them down. “I’m just going to prove to you that I’m no tease!”

“But Karen, you’re married!”

“Yeah. I’m married. So are most of us around here, but as we like to say… we’re just married, not dead!” she continued as she pulled my jeans down to my knees. She looked at my boxers tented straight out from my hard cock.

“Oh, Tom. I can’t wait to see this!” she said as she grabbed my boxers on both sides and ripped them down to knees. My cock bounced right back up and hit the underside of her chin.

“OH TOM! What a nice cock!” she said as she immediately wrapped her right hand around it and squeezed it. More pre-cum immediately dribbled out of my tip. “Oh God, yes!” she said as she lunged forward with her mouth open and swallowed my cock head. I felt her tongue lick the pre-cum from me as she brought her hand up my shaft forcing more pre-cum out into her mouth.

“Mmmmm.” she responded as she started to stroke me and bob her head on my cock.

I reached down and placed my hands on the back of her head and helped her bobbing head.

“Oh, Karen. Oh God, that feels so good.” I moaned out as she continued. I knew that I wouldn’t last long after all of the previous arousement. Suddenly her little hand held radio came to life crackling.

“Karen? Where are you and what are you doing?” the radio sputtered out.

Karen responded by stroking me almost twice as fast and bobbing her head faster too.

“Karen? Karen? Are you there, Karen?” the radio blurted out again.

Karen pulled away from me still holding my cock tightly. “FUCK!” she yelled out and reached down with her other hand. “WHAT, BARB?” she yelled into the radio.

“What are you doing? Where are you? I need you!” Barb said.

Karen started stroking me again as she looked up at me. “I’m busy. What do you need, Barb?”

“Busy doing what, Karen?”

“Going to the bathroom, if you MUST know. What do you need, Barb?”

“Mrs. Johnson is acting up again and I need your help in her room.”

“OK, someone will come very soon.”


“I meant, I’ll be there very soon.” Karen said.

“OK, hurry though, please!”

Karen dropped the radio and held my cock tightly looking up at me and said, “I really need to go, but I’m going to finish this first to prove to you that I’m NO tease!” and she sucked my cock down until it met the top of her hand. She let go of my cock and placed both her hands on my ass. She lunged forward, forcing my cock down her throat. She started deep throating me quickly.

After a few times, she pulled back and grabbed my cock and said, “Tom, cum quickly! Cum for me!” she said and started deep throating me again.

On the third plunge into her throat, I screamed out, “Here it comes. Oh GOD!!!” and I shot out as she was pulling back and I filled her mouth with my stream. She tried to swallow it all, but some of it came out both sides of her mouth.

I squirted out again and again. She tried to keep up, but even more came out the sides of her mouth. Some started to drip down her face and onto her dress and in her cleavage. She completely drained me and made sure she got every last drop out of my cock.

When I finally went limp, she pulled me out of her mouth and licked up all of the cum she could reach with her tongue around her lips. “Holy shit, Tom. I don’t think I’ve had anyone cum that much before.” she said smiling and looking up at me.

I reached down with my finger and wiped off the rest of the cum from one side of her face. She grabbed my hand and stuck my finger in her mouth and sucked it clean. I did the same with the other side and she again cleaned my finger off.

I reached down to her cleavage and when I wiped my finger in her cleavage, she moaned out loud. Then she said, “Oooooh. God, Tom, I want to get naked and fuck the shit out of you right now!” and then started stroking my soft cock causing it to start to harden.

“You know you got some on your dress.” I said.

She stopped stroking me and let go. “Oh shit! Fuck!” she said and started wiping it up with her fingers. She stood up and then went back to the bathroom.

“kkkkkkk” the radio came to life again. “Karen? Where are you? I need you right away!” Barb’s now familiar voice said.

I pulled my boxers up and then my jeans and zipped and buttoned myself up. I grabbed the radio and went to the bathroom where Karen was using wet toilet paper trying to clean up her dress. “They’re calling for you desperately now. It sounds like they really need you.” I said.

“I guess that’s as good as it gets.” she said and grabbed the radio from me. “I’m on my way!” she said and then looked at me and said, “I proved that I’m not a tease. It’s your turn to prove that you’re not one either. We’ll have to continue this later, huh?” she said as she reached out and palmed the front of my jeans.

“I’ll see you later, big boy!” she said and walked out of the bathroom and then out of the room into the hallway.

I couldn’t believe what had just happened, but I sure thought that I was going to thoroughly enjoy doing the maintenance around here! I walked out of the room and to the truck to grab some tools to tear into the wall to figure out what was going on.

I ran into Carl on my way and he had finished up with the lights and asked what was going on. I explained and he went with me to get the tools and then back to the room. After about an hour, I finally saw what was going on with the pipe. It had a crack in it and was going to need a section replaced.

We cut the wall out in the corner in order to be able to do the pipe repair later. We went ahead and cut the wall out around the hole to the studs so that we could replace the drywall ther later on too. After cleaning up, it was quitting time. I went to Karen’s office, but she was already gone. One of the other workers told me that she works from 6 to 3 and was gone for the day.

I left her a note that I would be back in the morning around 8 to repair the pipe and talk with her when she was available about the painting.
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Copyright © All stories are original stories, both fiction and non-fiction. I retain all copyright and all rights reserved as per the copyright law of the United States. No portion or any story in it's entirety can be republished in any form without the written consent of myself.

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