Chapter 1: Jack’s Story

Despite all my reservations, I had agreed to house sit my parent’s place for a month this summer while they were on vacation in Europe. My parents lived in the suburbs and were far from my usual stomping grounds. Literally, there was nothing, but nothing, around unless your amusement was the local shopping mall.

“Jack,” my father had said, “your mother and I would feel so much more comfortable if you were here. But, unfortunately, this wave of robberies in this area occurred when people were on vacation.”

“But Dad, I need to earn money for my next semester at school. Life at the university isn’t cheap.”

“I did not intend you to do it for free,” he told me. “I will pay you the equivalent of what you would have earned at a summer job.”

So there I was in suburbia, condemned to a summer of watering the garden, mowing the lawn, and going to the mall and the supermarket for the next four weeks.

Fortunately, there was a good gym at the mall, and I was allowed to use my parent’s membership. So my life settled into the gym routine in the morning, followed by some housework and gardening. Since this was almost a retirement community, there were few people my age around.

My gym classes were almost a religion for me as I was determined to increase my strength and muscle mass in anticipation of returning to the university wrestling team in the fall. I had done well the last semester and competed in the inter-university championship at the state level, winning my division. It was my goal to compete at the nationals in the coming year.

Because I got to the gym as soon as they opened, I was usually alone and could do my workout uninterrupted. Fortunately, most people using the gym didn’t show up until I was ready to leave. They all appeared to be older men and women who were in dire need of a good workout. The sight of all the flab and adipose tissue was not something that would inspire me.

After the first few days, I was no longer alone. A woman was there at the same time I was each morning. She must have been in her middle forties; however, she was fit and good-looking. The first two mornings, she just smiled at me and nodded her head as she went on with her exercise routine. She seemed to prefer choosing a location at the other end of the gym from where I worked out.

On the morning of the third day, she walked up to me. I had ended my exercises and was preparing to leave. “Good morning, are you Jack, Andrew’s son?” she asked, smiling at me and holding her hand.

“That’s me,” I answered, taking her hand. “Do I know you?”

“I’m Meg Thomson, your parent’s next-door neighbor,” she answered with a smile.

My expression must have spoken volumes. She burst out into a peal of laughter. “I don’t think you were expecting that, were you?”

“Uh ... not really. You don’t look at all way the way I remember you. What happened?”

I remembered her as a somewhat plump unsmiling woman who was rather cold and aloof. But, she was nothing close to this woman who now stood before me.

Gone was the plumpness. What I had in front of me was this slim, sexy redhead with magnificent green eyes and a lush, sexy figure.

“Jack, I’ve been a widow for the last three years. When my husband died, he left me with the means to indulge myself. I decided that I wasn’t particularly enamored with what I looked like or who I was. What you are seeing is the result of a two-year makeover.” She answered, smiling at me as she made a slow 360-degree turn. “What do you think?” she asked.

“You certainly have done a great job. I would never have recognized you if you had not introduced yourself.” I said, smiling back at her.

“Well, you’ve also changed. You don’t resemble that gangly boy I last saw headed off to boarding school. Instead, my god, you’re a man and a very good-looking one.”

“Thank you, Mrs. Thompson,” I replied, feeling my face heat up.

“I have to get going, Jack. I am sure we will see each other often now that you are at your parent’s place. If you need anything, just come over and ask.”

I watched her walk away and admired how her ass swayed as she walked away from me. This was a very hot-looking babe, and I was left thinking that I would certainly be interested in pursuing something with her. But, of course, I was no virgin; however, the girls I had been dating did not have the sex appeal this older woman exuded.

A week later, I was out in the backyard finishing my outdoor chores. I had pulled out a lawn chair and stretched out to catch some rays. Wearing a pair of shorts commando style, I stretched out to enjoy the sun. Then, a motion in the adjoining yard caught my eye, and I saw her.

She was wearing a green bikini that revealed more than it covered. Noticing me, she called out, “Hi there, handsome,” as she waved at me.

I waved back and said, “Hello, Mrs. Thomson.”

I watched as she walked over to me. I could see her eyes examining me from head to foot.

“Jack, no more Mrs. Thomson. Please call me Meg. That way, I’ll feel less like an old woman.”

“Uh ... okay, but I can assure you that I don’t see you as an old woman.” Then my mouth went on automatic, “You are a gorgeous woman in my eyes.” I felt myself blush as the words came out. Shit, I hoped I had not offended her.

Her eyes twinkled, and she gave me a sweet smile, “Please don’t blush; you have made my day. That’s so sweet.”

“May I sit here with you for a minute?” she asked as she sat next to my chair on the grass. “I would like to speak with you about an idea that came to me.”

“Sure. Can I bring you a lawn chair?”

“No, this is fine,” she insisted. “Jack, one of the elements of my makeover was that I have become an artist. I have always been artistic and decided that painting was what I wanted to do. I have become somewhat successful, and my paintings are noticed in the art world. So I thought about you and realized that you would make a great model for my next piece. Is that something that might interest you?” She asked.

“Me ... a model? Now there’s something I’ve never considered.”

“You have a great body that brings some very classical elements to my mind. I watched you from my yard and thought you would inspire me to do my best work. I have this commission to do a painting for a private collector. I couldn’t pay you right away, but we could share the commission when the sale is made.”

“Meg, I’ve never done anything like that before. I don’t know how to be a model,” I answered.

“Oh, don’t worry about that; I’ll show you how to pose. It is not hard ... but it’s tiring. Maybe you’d be more inspired if I said you’d make a cool $1,000 when I deliver the finished work.”

“Wow, you get that much for a painting?” I blurted out.

“Oh no,” she laughed. “I make much more. The thousand would be your share of the proceeds. So, have I sparked your interest?”

“Sure have. When would you want to do this?” I answered, thinking the money would be great, but it would also put me in close contact with this woman who certainly was having an erotic effect on me.

“We could start tonight if you’re available. I’ll go out this afternoon to get the materials I need. Normally painters like to work in the sunlight, but it will be cooler this evening, and painting can be hard work. So come over at six, and we will get started.”

Meg’s Story

“Three years,” she thought to herself. “It’s been three long years since my husband passed away. During the first year, I spend my time sorry for myself and reflecting on my life with him. It was not a pretty picture to contemplate.”

Over the fifteen years of marriage, I had let myself go. I had turned to fat, was shrewish, and not the picture of the woman he had married. Our sex life had become a Saturday or Sunday ritual neither of us enjoyed, but rather just a way of relieving our pent-up frustrations.

I had decided to embark on a two-year process to lose weight, become fit and change my outlook on life. Innumerable self-help books and seminars later, I realized finally that I had to start loving myself. It was not an easy road. Ultimately, however, I began to do things that would bring pleasure into my life, or at least some satisfaction.

I had always had a passion for art and took up painting. Over time my works started to be recognized. Finally, I had reached the goals I had set myself two years ago. I was happy, I looked sexy, and once again, I was feeling horny.

Going to the gym had become an integral part of my life, and when I saw the young man working out at the other end of the hall, I found myself watching him and admiring his body. I could feel my pussy aching with desire and getting very wet. But, afraid he would see the stain he was causing on my crotch, I avoided him for the first few days even though I thought I recognized him.

On the third day, I mustered up my courage. Having taken the precaution of wearing a panty liner, I introduced myself. He was my next-door neighbor’s son, as I had surmised. Driving back home, I made up my mind that he would be my first new conquest and my reward for three years of celibacy. He would be the reward for all the hard work I had done for myself.

Just looking at him made me drool and drip. But, I also noticed that he was not immune to my looks. A discernible bulge formed in his shorts as we chatted.

That same afternoon I saw him in the backyard mowing the lawn and then lying down to tan. I had gone over and proposed to him that I needed a model, and he was my choice of the perfect subject for a new painting I had been commissioned to produce. He had accepted my proposal after hearing how much I would pay him, but I was hoping that maybe he was also interested in me as a woman.

At 6:00, I was waiting for him to arrive. I had taken a shower and thoroughly washed. My pussy was freshly shaved. I had not been able to resist pleasuring myself at the thought of seducing this young man. “Meg, you’re a cougar,” I thought with an inner smile.

Dressed in a pair of skin-tight shorts, a man’s shirt, and barefoot I went to answer the door when he rang. He was dressed in shorts and a t-shirt and looked delicious.

“Hi, Jack. You’re very punctual,” I said, smiling at him. “Come this way to the studio.”

I led the way making sure I wriggled my ass with each step. I could see him in the mirror as he followed me. His eyes were riveted on my backside. This is going to be easy, I thought to myself. I could feel my pussy tingling in anticipation.

I had already set up my easel and paraphernalia, the canvas had been prepped, and all that was missing was my model. I led him to a small platform and asked him to stand on it.

“Now, Jack, take off your shirt, please.”

“My shirt? You want me to take it off?” He asked sheepishly while blushing.

“Yes, please. This painting is going to be a nude. It will depict a wrestler ready to grapple with his opponent. Is that going to be a problem for you?”

“Uh ... I guess not. I just wasn’t expecting it, that’s all. But hey, why not? Do you want me to remove my shorts as well?” He asked.

“Are you wearing underwear?”

“Yes, I have jockey shorts under.” He answered.

“Okay then, take off just the shorts. It will give me a better opportunity to sketch what I need.” My inner naughty self was already in overdrive, contemplating how I wanted this to end.

I stepped behind my easel to give him some privacy to strip down and get comfortable with the idea. Then, when he voiced that he was ready, I proceeded to show him the stance I wanted him to take. Knees slightly bent, arms up as if prepared to grapple with an opponent.

He was magnificent. His muscle definition was perfect, he was ripped, and his body was relatively hairless except for some fine blond hair on his muscular arms and legs. I had to resist jumping his bones right then and there.

I got back behind my easel as he assumed the position I had asked him to take. I started to sketch his body with charcoal on the canvas. A large mirror placed behind him enabled me to admire his back and firm buttocks encased in a very brief slip.