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Part 4

I Need A Break

Tim is desparate for some time off
I Need A Break

I just got back to Medford in time to get undressed and go to bed. I was hoping this venture would be a good way to spend three to four days a week. It’s been on the run ever since I met Cynthia and not all computers. I do need time off.

The next morning George Lewis from Overton walks in the door. I had a good night’s sleep, so I was ready to get back to work. George poured a cup of coffee from the table and sat down by my desk.

“George, it’s great to see you. What brings you to Medford?”

“I had a couple of days off, so I thought I would give you a visit. It’s nice to get away for a day or two. The system at the office is running great and Mrs. O’Connell can’t stop bragging about the low cost.”

“I enjoyed my time in Overton. You and everyone were so welcoming. It’s a great place to live. That’s why I came to Medford. I wanted a nice town to have a small business and help wherever I can. My first customer was Cynthia Crenshaw. Ever since then, I have had to keep my repair bag packed. I am grateful for all the business she has brought to me, but damn, I need a rest.”

“Where do you want to go?” asked George.

“I don’t know. I understand Miss Thompson at the library is well-versed in this and the surrounding area. I may ask her for an idea or two.”

“If you find a place, call me. I’ll ask the Sheriff for a few days. I’ll come up here and cover for you. You know, I’m pretty good at computers.”

“That would be wonderful. I will take you up on your offer. George, you are a lifesaver.”

Two weeks went by, and the repairs were caught up. The two house calls were simple, so I was beginning to see the light at the end of the tunnel was not a train coming at me. I started to relax.

Late on a Tuesday afternoon, I was sitting back, having a nice cold beer, and listening to Country Western on my phone. I was on my third beer and the door opened. Enter Mrs. Cynthia Crenshaw preceded by her perfume.

“Hello Tim, how are you?” Cynthia said in a tone that warranted caution.

“I was hoping you could close your business a week from this coming Sunday for about four days. I want you to come with me to my other home. My friends are having a get-together, and I am hoping you will be my escort. They are very nice people, and you will fit right in.”

Fit right in, sure. Maybe as a busboy or servant, but with that crowd, I would be the pink elephant in the living room. These people have tons of money, and it is obvious. Cynthia and Lillian don’t flash it, but even the perfume reeks of Ben Franklins.

“Cynthia, I don’t know. I am just getting caught up with my repairs. I don’t have a suit and I have an obligation to my customers. Can I call you tomorrow and see if I can plan to be closed that week.”

“Excellent. So, plan on me picking you up and eight on Sunday morning. I know you will love my friends and have a wonderful time. Talk soon.”

And Cynthia made her exit and had taken with her my option of saying “No”. I hate to infringe on George. He was great to have with the installation in Overton. I hate imposing myself on friends. I don’t want to lose Cynthia’s influence and connections. Damn, hello, George.

“Lewis.”, George answered his phone.

“George, Tim Ouster here. Is your offer still open to watch the shop? I have an “offer” from Cynthia Crenshaw to go to a party with her friends a week from this coming Sunday. I should be back on Friday. I know it’s one hell of an imposition. Why are you laughing?”

“Mrs. Cynthia Thompson Crenshaw. What a piece of work. She is one you should not say “No” to. She can ruin your business. I’ll cover for you.”

Seven-thirty on Sunday morning, I was packed, but not ready to go. The door opened, and Cynthia’s perfume entered the room followed by Cynthia. I didn’t know if I should bow or genuflect.

“Good morning, Tim. I hope you slept well. It’s about a three-and-a-half-hour drive, so I need some nourishment.”

With that, Cynthia unzipped my shorts and pulled them and my underpants down in one swift motion. She pushed me onto the couch and knelt in front of me. She had my cock halfway down her throat before I could get comfortable. She pulled me to the end of the couch, so she had access to my balls.

Cynthia began sucking and licking my balls as only she can. She busied her hand stroking my hardening cock. My balls were in her mouth and her tongue was giving them an oral massage. She is damn good. After a few moments of oral and manual seduction, she switched.

Now Cynthia had my balls in her hand and my cock in her mouth. Her face was buried in my crotch and her tongue was massaging the underneath of my cock with great expertise. As she fondled and pulled my balls, her mouth began sucking up and down my shaft. It was like being in a vacuum. She would suck going down and up.

She grabbed my cock with her free hand, continued to pull my balls, and was wrapping her tongue around the head of my cock. As her tongue swirled around my cock head, I was getting closer and closer to my climax.

She removed her mouth and stroked my straining cock with a few expert strokes. My cock went back in her mouth, her tongue swirled around my cock head and I shot every ounce of sperm from my balls into her waiting mouth.

“Now that’s how I love to start a day. Now, I want to be sure, I haven’t missed anything.”

My cock was back in her mouth being attacked by her sucking and licking again. My heart was pounding through my chest, and my lungs were straining for air. When she was sure nothing was missed, Cynthia brought me a cup of coffee. And was ready to get on the road.

“I hope you’re relaxed for the drive. I’ll have you drive. Then, if I need to relax, you will have a free hand. Now, get dressed and we’ll be on our way.”

I love subtle intimacy. So unexpected, so spontaneous, so sit down and let me give you a blow job. I am not complaining, just stating facts. I wonder what Cynthia would do if I did the same to her. She would love it.

We’re driving down this two-lane road through the countryside. Everything was so lush and green. It was beautiful. The wind blowing in our hair, blue sky for the roof of her convertible, a small billow of cloud would pass overhead, the air seemed so fresh. We stopped in a nice-sized town at a tailoring shop. When we walked in, the owner knew her on-site.

Mrs. Crenshaw, how can I help you? he asked.

“Billy, this is Mr. Ouster. He is up for the weekend and has forgotten his suit. Would you be so kind as to fit him?”

“It is my pleasure, Mrs. Crenshaw. Casual, formal, what will be the evening’s attire?”, Billy asked. “May I suggest a black coat and slacks, with socks and shoes to match? Maybe a white shirt, button down collar to be left open at the neck.”

“Excellent.” Cynthia agreed.

“Mr. Ouster, will you please follow me.” Billy pointed to a room down a short hall.

Billy found coat and slacks to match that if I didn’t know better, I would have sworn he had it tailor-made for me. I looked damn good. Cynthia was very pleased. Billy put a plastic bag over the purchase, and out the door, we went. I wonder what her accountant says when he sees some of her purchases.

When we got back into the car, Cynthia decided it was her turn to relax. She turned to me with her back against the door of the car. She pulled her dress to her waist and opened her legs. I ran my hand down her thigh to her warm spot.

Cynthia closed her eyes and smiled. I tried to lightly touch her pussy lips, but Cynthia only slid down in the seat making my finger slide into her. She reached for my hand, combined three fingers, and reinserted them into her passion pit.

Using my fingers as her sex toy, I thought, this is a good spot to pull over. I stopped the car and pulled my hand from hers. She gave me a disappointed look. I got out and went to the other side of the car. I opened the door, and Cynthia turned toward me and looked surprised. Then I pulled her legs until her sweet round ass was just at the end of the seat.

I got on my knees, put her legs over my shoulder, and shoved my tongue into her wet pussy. I was sucking and licking for a while and Cynthia pushed my head into her crotch. I didn’t stop my oral assault on her passion pit, and she started humping against my mouth.

I reached around her legs and pinched her large tits with my fingers. Her nipples were not in the safety of a bra and her reaction was immediate. Cynthia started to climax as I have never seen before. Panting, moaning almost groaning while she humped against my mouth. I licked and sucked every drop of her delicious vaginal juice.

When she had recovered a bit from her experience, I pulled her out of the car. I turned her around so she could put her hands on the seat still wet from her orgasm. I dropped my shorts and shoved my hardened steel rod into her.

She let out a whimper, and I started pounding her. I gave it to her so hard you could hear our flesh slapping together. I grabbed a handful of hair but never missed a stroke. Cynthia whimpered and let out a cry like a kitten and flooded my cock and balls with more sex juice.

It was then, my balls exploded with every drop of sperm I had at the time. Her hot juices and my streams of lava mixed and gave me a euphoric orgasm like never before. My exhausted cock slid from her soaked pussy and held onto the car door to keep my balance.

Cynthia sat on the car seat. She was still panting. Her face was flushed and sweat dotted her forehead. She looked up at me smiling her sexual smile. I bent over and kissed her hard.

“Where did that come from?”, Cynthia panted out.

“My balls. You said you wanted to be relaxed, and it seems that whenever I give you some hard sex and a load from my balls you get relaxed. And it seems you want to make sure you have every drop you always pull my cock back into your mouth for a few more sucks. So, take a few more licks.”

I leaned toward her, and she opened her mouth and sucked on my limp cock. She did take a few more licks then released my captive cock.

“You do know me, Tim.” Cynthia cooed.

I didn’t realize that it was still a fifteen-minute drive to the house when we got to Crenshaw’s driveway. Did I say “HOUSE”? This thing is huge. I walked into the living room looking for the sign on the wall that stated, ‘YOU ARE HERE”. I followed Cynthia down the hall to a bedroom that just said “Cynthia”.

Lacy white curtains, white satin sheets, dressing table with rose marble side tops. Not to mention the plush carpeting. While I was taking in the “Louis the Fifteenth” furniture I compared it to my thrift shop Living room set. This is where I must fit right in. Right.

“I’m going to freshen up a bit. We are to be at Elenore’s at four. I have made sure there is plenty of beer for you. Just go to the fridge in the kitchen.” Cynthia said then disappeared into what was probably an Olympic-sized shower. I should have left breadcrumbs from the front door.

It was just before one in the afternoon, so I was ready for a cold beer. I found the kitchen, grabbed a cold one, and sat at the breakfast nook. It was an amazing house. From the kitchen, which was adjacent to the living arena, was a clear view of the swimming pool. The gardening around the pool made you think you were in a palace somewhere.

I was standing at the kitchen door admiring the pool when Cynthia came up behind me.

“It is beautiful out there. The pool is cool and refreshing. We have a gardener on staff to keep it looking wonderful.” Cynthia said.

I turned to agree with her, she was naked. Why was I surprised?

“I don’t wear clothes here. There is usually no one here other than me. Tim, I hope you will change that from time to time during the year. I do get so lonesome here. Take your beer and have a shower. I’ll be in the living room. Take your time.”

The glass-lined shower was huge. You could fit three people in there with no problem. I wouldn’t be surprised if that had happened before. The hot shower and shave felt good. This was going to be a memorable week, but I couldn’t live like this.

The shower was wonderful. For some crazy reason, it felt better than my shower at home. Maybe it’s piped in spring water and not like the city of Medford water supply. I was toweling myself dry, and I looked at my new suit in the plastic sheath, then went to meet the lady of the house in my birthday suit. No resemblance.

At the first stroke of four, I rang the bell at the “Home” of Elenore Winston. A gentleman opened the door wearing a black waistcoat, white starched shirt, and black bow tie. He was smiling when he opened the door wide.

“Mrs. Crenshaw. A pleasure to see you again. How have you been?”

“Hank, I have been doing quite well. May I introduce you to Tim Ouster? He has recently moved to Medford. He is into computers and security management.”

“It is a pleasure to meet you Mr. Ouster. If there is anything you require, please alert me.” Hank said in a very pleasant tone he has said for who knows how many years and how many times.

I said, “Hank it is a pleasure to me you as well. If there is anything I will let you know.” My mind said, Yes, this is where I fit in. No.

I’m guessing that Elenore is another exquisite woman around Cynthia’s age and monetary bracket. When we were introduced, it was obvious Elenore Winston was proud of her cleavage. Elenore and Cynthia were in a conversation, and I was taking a quick glimpse of Elenore’s very ample breasts when I hoped I wouldn’t be caught. But Cynthia did catch me looking. OK, so I got busted.

When they finished their conversation Cynthia said, “She has buried three husbands, Tim.”

“Hell, Cynthia, you damn near buried me the first time we met. You know I am very fond of you.”

“We all are.” Came a voice from behind me.

“Tim, I want you to meet Patricia and Albert Trenton. They live in the house next to mine. We moved in almost at the same time. Cynthia added.

“It is a pleasure to meet you both,” I said and extended my hand to shake Albert’s. We traded firm friendly handshakes.

“Tim, I understand you are a computer person,” Albert said.

“Yes, I am. I moved to Medford to start a little business to keep me out of trouble three or four days a week. Thanks to Mrs. Crenshaw I have all the business I can handle. She has been very kind to me.”

Patricia stepped in, “Enough of the Mr. Sir and Mrs. Ma’am. I am Pat, this is Albert, we are at Elenore’s you are with Cynthia and your name is Tim. Does everyone agree?”

“Great I said. Can I bring anyone a drink?” I asked.

About this time Hank walked up with a full tray. The drink of choice for each of us.

“Hank, are you a mind reader?” I asked.

“No sir. I’m just good at what I do.” We all enjoyed a good laugh at his response.

A commotion had started at the other end of the patio, by the pool. It appeared I was about to meet Avery Thompson, Cynthia’s other brother. The brother no one talked about.

I started to walk over, but Elenore grabbed my arm.

“Tim, come with me, please.”

I followed her to a small hidden shed at the back of the house. When we got in the shed, Elenore undid her blouse, and her large soft breasts sprang from their bondage. It didn’t take me long to understand life is big money.

I sucked Elenore’s large breast and squeezed the other. She was panting. Her hands were on the back of my head as she held me to her breast as if her life depended on it. Elenore was rubbing my hardening cock through my pants.

I undid my pants and dropped them and my boxers to the floor. I turned Elenore around. I pulled her dress up past her waist and forced her panties to the floor. I stood behind Elenore with my shaft pointed at its target. I slid it inside her.

Elenore winced a bit. “It’s been a while, but don’t stop.” She said.

I slowly stroked my cock in and out of Elenore’s warm vagina. After a short time, I increased my rhythm to Elenore’s delight. Now she was used to my cock in her, so I reached around and fondled her huge soft breasts. It wasn’t long before she was bucking back on my cock. Our bodies were slapping against each other as she started to moan and push harder against my intruder.

I grabbed her nipples between my thumb and index finger and twisted and pulled them. Elenore had to climax. She shoved her passion pit on my raging cock and winced and whimpered every time I pulled her nipples. I pumped her harder and Elenore finally gave in. Her orgasm trickled down to my balls. Then I released whatever I had restored in my balls from earlier in the day.

Elenore straightens herself up to look presentable. I tuck in my shirt and straighten my collar before we part. Elenore turned to me,” Go down to the pool area where the commotion had started. I’m going to the house to fix myself. Thank you, Tim”, and Elenore left.

When I got to the pool, all hell had broken loose. Hank was trying to restore order as a gentleman, but that was not going to work. This nut was way too drunk to reason with. I found Cynthia, she gave me a knowing look.

“Your brother?” I asked.

“Yes, Tim. Avery was the third child. He could do no wrong. When our Daddy died, he left a very nice inheritance for all of us except Avery. Daddy knew it would go to drink or up his nose. We don’t know how he affords his lifestyle.

“Can I try to stop this before someone gets seriously injured?”

“Yes, Tim, please do.” Cynthia pleaded.

“Cynthia, ask Hank to bring a wheelbarrow down by the pool, please.”

I walked over to Avery who has no clue what planet he is on. But he speaks fluidly drunk. The bartender is doing his level best saying no more booze, but Avery isn’t having any of that. Reasoning with this guy is going to go as well as swim fins on a buffalo. Let’s try the absurd.

“Hey! Aren’t you Avery Thompson? Aren’t you the guy who won that five-thousand-dollar poker pot in Templeton last week? Damn, you played some shrewd hands.”

“Yesh, that wash me. Who in hell are you?” Avery asked.

“I was watching that last hand, and that guy thought he had you beat. You showed him a great bluff and took the whole pot home. You were just great. Here, let me get you a drink.”

All you could hear was Avery, me, and the pool filter. I don’t think anyone was breathing.

“Hey, man. What do you want to drink?” As I asked Avery what he wanted I whispered to the bartender, water.

After a few attempts at the English language, Avery was able to ask for a gin and tonic. As I reached for the glass of water from the bartender, I whipped around, I caught Avery in the head with my elbow. He went down in a lump and never got up. In a minute or two, he was snoring.

Hank and I lifted Avery into the wheelbarrow, and Hank wheeled him to his car.

Albert asked Elenore, who had rejoined the party if she wanted to call Gerald, the town constable. Elenore refused but thanked him just the same. Everyone knew of Avery’s addictions but didn’t do anything to help him. Truth is, he didn’t want help.

The witching hour was approaching, and it seemed as though everyone enjoyed the evening despite the commotion. It was time to say good night. Elenore was thanked and praised for her selection of guests and food. Cynthia and I just held back and watched for a while.

When the guests had left, Elenore came over to Cynthia and me. She was smiling from ear to ear.

“I have to tell you, I am torn. I want to thank Tim for your handling of the situation, but Cynthia, I am sorry for how it ended.”

“Elenore, we all know Avery is a low life. Every day, his brother and I are surprised if we don’t get a phone call telling us that he was found dead in an alley. And I want to thank you for letting Tim join our festivities.”

I said to Elenore, “I had a wonderful time. I do apologize for the fisticuffs, but to me, it was that or throw him in the pool. Considering this is my first-time meeting Cynthia’s friends. I don’t mean to be forward, but I hope to see all of you again. Everyone was so kind to me.”

“Elenore, didn’t I tell you Tim would fit in with our group?”

“Yes, and he fit in perfectly.”

I’m glad it was dark because my face was fire engine red by this time. I had a weird feeling that Cynthia knew I had sex with Elenore but wasn’t saying anything. Damn, I hope I didn’t louse up a good thing with Cynthia.

Cynthia and I were walking arm-in-arm back to her car. It was the only one left in the driveway.

“I am very proud of how you handled Avery. I was sure he would show up, but there would be no one there to handle him. I knew you could. But that’s not the reason I wanted you to be with me. I want you to be in our circle. Lillian couldn’t make it tonight or she would have been here. I am very proud of you and very fond of you. Everyone there likes you. You do fit in.”

I opened Cynthia’s car door and then walked over to the driver’s side. I got in and put the key in the ignition. Cynthia was staring out of the front glass. Without looking she put her hand on my crotch and gave me a gentle squeeze.

“I hope Elenore left some for me tonight.”


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