Crazy Times Pt. 01: Week 1

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A younger guys adventures with a demanding older woman.
2.6k words
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Part 1 of the 3 part series

Updated 06/10/2023
Created 06/08/2020
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Much to the dismay of people that knew me, at twenty-five I had just moved in with the sexiest woman I'd ever dated. She stood five-three, had an athletic one hundred and thirty-five pound frame that she worked hard to keep in shape, a set of 36 D tits, an ass that was perfect from all the squats she did and legs that were strong yet supple. Her blonde hair framed her features attractively and her blue eyes were so blue they were haunting. We dated for two months before she asked me to live with her. Dating her wasn't exactly making me popular with people that knew me. Being twenty-five and dating a forty-six year old cougar was fun but when I moved in with her my friends questioned what I was doing and my family thought I had lost my mind.

Sitting down, on a Sunday evening, we were done getting me moved in. The house was big. She owned a nice ranch house outside of town. It had a rustic look with the log cabin style finish and the inside was modernized. There was enough room that I could have a work space, a private office of my own to work on writing. It was my dream job. Having finished school I had to take a job to make ends meet and hadn't been able to focus on what I really wanted to do, on my dream.

The offer was not without its' speed bumps. Laurie was a very detail orientated person. I was seeing why she was single, or at least I thought so.

Before we moved in together, she presented me with her list of rules. It actually was, a list, printed out on paper that she wanted me to sign after I read through them. When she told me I could have a year or so to work on writing, take care of the house and the grounds and earn a regular pay check all at the same time I would be living with her I was surprised. Laurie made it seem all so pragmatic, she'd save a little on hiring out the mowing, give me a chance to have a real try at writing and have her guy with her.

All I had to do was agree to her list. From my perspective, hot girl friend, a job, a great place to live and an income. Why would I not sign it?

"So," Laurie smiled as I signed the dotted line. "You're good with the agreement."

"Yes, I'm good with it." I smiled at her as I sat back in the chair.

"Starting tomorrow you know everything that's expected from you."

"Taking care of the yard work and exterior, working out daily and staying in the kind of shape you like, submitting to your desires, which is the fun part and spending my free time, at least forty hours a week, working on my novel," I listed off the key points.

It seems you understand the basics, she told me.

"Yes, I think so."

"And you understand that submitting to my desires means if I desire it, you have to do it?" she asked.

I couldn't wait. This was the sexiest part of her. She was a slightly dominant woman and it meant I was along for a ride. After three years of working my way through school, busting my ass, life all looked more simple this way. Somebody else was going to make more of the decisions.

"Absolutely," I told her.

"Alright," she smiled at me as she leaned in for a kiss.

"Starting tomorrow, unless you have to go somewhere or do something outside that would be unsafe, you will stay nude as long as you're here."

What? I thought it in my head as she said it. Surely she wasn't serious. How could she expect me to stay nude whenever I was at the ranch? How did she expect me to get anything done? Was this actually covered in the agreement? I flipped through the twelve page agreement I had just signed. On page nine it actually says 'Shall only wear those items as necessary, when necessary for legal reasons or safety reasons, to be determined by Laurie Quinn'.

What had I agreed to?

"Well, you're going to follow through with this, correct?" she asked, running her hand up my thigh.

"Is this why there are locks on my closet and drawers?"

"Now you see the purpose of them?"

She'd given me a great place to live, she was providing an opportunity that I wouldn't have any other way, money, keys to a much nicer car than I could afford and a life I never dreamed of at my age. I knew she had quirks and was a demanding woman to begin with. Would it really be that bad? We laid out nude whenever she wanted to, went swimming in her pool without suits, spent weekends together without clothing on as we hung around her place. It's not like I had anything to be ashamed of so why not?

"I'll do it," I told her.

As soon as I said I would do it, she took me by the hand, lead me to the bedroom and began undressing in front of me. Peeling away her clothes, getting down to just a black thong panty, she dropped to her knees and unzipped my jeans. Fishing out my eight inches she playfully kissed the head of my cock before she parted her lips and took me in her mouth. The sensation of her sucking my cock didn't take long to drive me crazy and I knew I wouldn't last long. In just a couple of minutes I erupted against the back of her throat. Before finishing she pulled me out of her mouth, jerking my cock as I shot again and again onto her face and tits.

Not bothering to even wipe her face before she kissed me forcefully, she drug me onto our bed. My hands began to roam passionately across her body, one hand running down her leg as it wrapped around me. My mouth moved down her chin, kissing and nibbling he neckline. She began to playfully dig her nails into my back as I started to harden again. Sliding inside her, we got lost in the moment. Her back arched as a moan escaped her parted lips. Halfway in I lost control and pushed all of my length into her. Being so easily orgasmic, I could feel the walls of her pussy tightening down on me as I thrust inside her. She grabbed me shoulders harder, telling me she was about to cum. It was always the first one of the night that came so easily. I took a nipple in my mouth, nibbling at it as I grabbed her other tit and twisted the nipple, tweaking it. Before I knew it, she lost control and had the first of what would be three orgasms. She drifted off to sleep before I did, her head laying on my shoulder, nuzzled up against me.

I was spent. Spent and tired. As I looked down at how adorable she was as she slept against me, I wondered how the future would look. The agreement she wanted me to sign was on my mind.

After the first few days I was starting to get accustomed to my new living situation. There wasn't that much exciting about it, except for the insane sexual appetite Laurie showed having what she called a younger boy-toy around. We were doing normal couple things. I'd get up, start working on my novel and doing research. She'd get up, get ready for work and give me a kiss and a playful stroking before she left. There were things I had to do every day. They kept me busy and were sometimes exciting.

After Laurie went to work I would write for two to four hours. Checking the mail was one of the chores she left for me. The mailbox was at the end of the driveway, a good hundred and fifty feet from the house. There was a line of trees alongside the road that opened up where the driveway met the road. About eleven thirty or so I'd take a break to stretch my legs. I slipped on a pair of running shoes, one of the only things she left for me to wear, and would take a stroll down to the side of the road. During that first week it was weird at first, being outside without clothing, but I'll admit the feeling of the sun was nice on my skin. By the third day of this I was starting to slow down my walk. I found myself taking my time both coming and going. I'd get back to the porch and would sit down and look through the mail, full well knowing that the driveway wasn't gated and anybody could come speeding up to the house.

I'd grab some lunch, go back into the den and start writing again. I always shot for two hours at a time. Sometimes I would get writers block and would go out to the pool and swim a few laps, do pull ups, sit ups and start working out on the weight machine. By day four I even got on the treadmill and ran five miles. It was a slower five than I was used to but things were bouncing or flopping around more than normal.

Then, at the end of my nine to five schedule I would go out and make dinner. Laurie would be home about six so I always had some time to get things ready.

As soon as she got home we had a routine. She'd come in, slap me on the ass and tell me how glad she was to be home. This would be followed up by her starting to undress as she walked out of the kitchen. I'd bring things out and we would sometimes eat right away, sometimes she'd be laying on the table in front of a chair with her legs spread wide. This was her not so subtle way of telling me to lick her pussy. I'd sit in my chair and let her wrap her sexy, tanned legs around my head. I would start to tongue her neatly shaven pussy, slowly spreading her open with my tongue until the moaning grew loud enough for me to hear. Putting my tongue right on her clit she loved it when I licked in a circular motion. Occasionally I'd suck her clit, grabbing it slightly with my teeth. She would start to force my face onto her, tighter and tighter as I licked until her head dropped back and her eyes rolled.

After dinner we would walk out to the porch and have a glass of wine or three. Usually Laurie would have on a satin robe. I, of course, would have on a pair of sandals.

When Friday morning rolled around at the end of the first week I was surprised to wake up alone. It was only six-thirty in the morning so I knew my little sweetheart didn't have to be gone yet. I rolled out of bed, went to the bathroom and brushed my teeth before heading out to the kitchen.

There was music coming from the kitchen and I could hear voices. I wasn't sure who it could be so early so I very tentatively stepped into the doorway. As I got closer to the kitchen I could see Laurie sitting at the table, drinking a cup of coffee and looking through the morning news on her tablet. She must have noticed me as I got to the doorway as she waived me in.

I walked into the kitchen and started to go toward the coffee pot when I noticed there was another woman standing there.

"This is Tara. She's my part time maid," Laurie explained.

"Tara, this is Brian Jons."

I don't know what I was thinking because at first I almost instinctively moved my hands down to cover my exposed cock. Laurie almost immediately corrected me, telling me that covering myself wasn't in the agreement.

"It's alright, sir. Ms. Laurie already told me about the changes to the house," said Tara, taking a long up and down look at me as she smiled.

"You weren't kidding when you said the job would be more fun than normal. I could look at him all day," laughed Tara as she went about her business.

In a few minutes I started to get comfortable with things as I stood there making idle chat with Laurie and Tara. Tara was an attractive woman in her own right. She had soft, caramel colored skin and a tight, athletic twenty-one year old frame. Her eyes were dark and her face flawless. She wore her hair long and straight and it cascaded down and around her shoulders.

"You see Tara, it's not that big a deal. I love having pretty things to look at," Laurie told her.

"Yes, ma'am."

"One of these days I'm going to figure out a way to see more of you on a regular basis," Laurie said by surprise.

"I don't know if I understand your meaning, Ms. Laurie," Tara said, surprised and judging by the nervous smile, a little taken back by her comments.

"Well, you're very attractive and I bet you have an incredible body. I'd love to see it running around her too.""

"Yeah, I don't know about that. I'm flattered but..."

"What if I paid you an additional thousand dollars a week?"

"What are you saying?" I asked her. "That's kind of rude, isn't it?"

"You would pay me a thousand dollars a week to do what exactly?" asked Tara.

Laurie pulled her purse off the seat next to her. "I'd pay you a thousand dollars a week more just to do what you're doing with one exception. You'd have to do it in the nude, five days a week from six to two and all you have to do is take care of the inside of the house."

I could not believe it. Was she that horny that she'd risk a sexual harassment suit. As much as I was imagining the body on her maid, Laurie was pushing the line and pushing it hard. Much to my surprise, Laurie started counting out one hundred dollar bills. By the time she reached one thousand, Tara started unbuttoning her dress. She let it slip down around her shoulders, revealing what must be a 38d cup set of wonderful tits, a flat tummy and a slightly plump but firm looking ass. She slipped off her bra and panties and stood there in just her heals. All I could think was OH MY as my cock started to twitch.

"See, honey, you're not the only one that I like looking at."

"Here you go girlfriend," Laurie told her, handing her the money. "You just do everything like normal and I'll give you an extra thousand every Friday, tax free."

"Yes ma'am," Tara told her before walking over to the counter and starting to do dishes.

Laurie gave me a kiss and told me she'd be late. "I'm making the final decision on the new business today. I'll be home a little after nine," she said, palming cash in my hand.

"This is too much. We agreed on five hundred a week."

"Yeah, but I've left you some additional instructions for today so I'm giving you a bonus," she responded.

Just like that, she was off and running. Leaving me standing there with in the nude with the now naked as I was maid and an all too familiar feeling of arousal.

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