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. There has been this wave of robberies in this area occurring 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 for you to do it for free,” he told me. “I will pay you the equivalent of what you would have earned on 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. My life settled into a routine of the gym 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 to 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. It seemed that most of the people using the guy 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.

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 putting out 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. In my mind there 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 with 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. My god, you’re a man and a very good looking one at that.”

“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. I was no virgin, but the girls I had been dating did not have the sex appeal this older woman exuded.

A week later I was out in the back yard 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. 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 an incredibly beautiful 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 in 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 being noticed in the art world. I was thinking 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 to my mind some very classical elements. I was watching 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 when the sale is made we could share the commission.”

“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. 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. The first year I spend my time being sorry for myself and reflecting on my life with him. It was not a pretty picture to contemplate.”

Over the course of the fifteen years of marriage, I had let myself go. I had turned to being fat, 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 towards life. Innumerable self-help books and seminars later, I realized finally that I had to start loving myself. It was not an easy road. However, I started 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 were starting to be recognized. 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. Afraid he would see the stain that he was causing at my crotch; I avoided him for the first few days even though I thought I recognized him.

The third day I mustered up my courage. Having taken the precaution of wearing a panty liner, I went over and introduced myself. He was my next door neighbor’s son as I had surmised. Driving back home I made up my mind that he was going to 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 on myself.

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

That same afternoon I saw him in the back yard 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 lead 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 had been 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.

“Ok 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. 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 ready 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. There was a large mirror placed behind him that enabled me to admire his back and firm buttocks encased in a very brief slip.

After about forty-five minutes of sketching, I walked over to him. “Ok relax, I’m done with my preliminary sketch,” I told him. “Would you like to see what I’ve done?”

He stood beside me beside the canvas, but I noticed his eyes were looking down at me. I had managed to open the top two buttons on my shirt and he was getting an unobstructed view of my braless tits. I smiled as I saw the bulge form in his jockeys as he started to get an erection.

“Can I get you a beer?” I asked. “Then we can relax and get better acquainted.”

“Sure I’d like that. Shall I get dressed?”

“No, just sit on the couch. We might do more work after you’ve had a chance to rest, ” I told him going out to get the beer.

When I returned, Jack was sitting the couch, massaging his calves and thighs.

“I told you that modeling could be difficult work. It looks like holding that awkward pose has made your muscles sore. Would you like to soak in the hot tub while we take our break?” I asked.

“Sure, but… I don’t have a bathing suit.”

“Jack, you will be posing naked before we finish. Remember at my age I have seen it all, so don’t be shy. If it makes you feel more comfortable I’ll take my things off and we can soak together.”

The expression on his face was priceless. The reaction of his cock was adorable. I could see it spring to attention and a little damp spot form where the tip should be. “Go ahead,” I directed him. “My hot tub stays ready. Go jump in I’ll join you in a few minutes.”

I gave him time to go to the backyard and get into the tub while I went and prepared the bedroom. I turned down the sheets and lit a few candles and some incense to set the mood. Once I determined everything was ready, I stripped down and examined myself in the mirror. Pleased at what I saw, I returned downstairs and went out to the tub.

It was a warm summer night but I could feel the goosebumps of anticipation as I walked in the dark towards the pool of light formed by the underwater lights. Shivering with excitement I stepped in while he gazed at my naked body. I was so mesmerized by the thoughts of what would happen that I lost my footing as I stepped in and ended up in his arms when he attempted to catch me.

“Sorry, I lost my footing,” I said. “I’ve always been a little clumsy.”

He sat with me in his lap. I could feel his hard cock poking into my ass crack. My pussy felt as if it was being jolted by electrical shocks.

Jack was obviously embarrassed and said, “Sorry, but you are such a sexy woman I can’t help that. I’m afraid it has a mind of its own.”

I swiveled my body around and wrapped my arms around his neck. “You think I’m sexy?”

“Meg, you have turned me on from the moment I first saw you at the gym. Yes, I think you’re sexy. I have wanted you and dreamt that this might happen, though I didn’t have any expectations,” he answered looking deeply into my eyes.

I moved my face towards him and our lips met in a kiss. I parted my lips and his tongue came out to play in my open mouth. Gladly I returned the favor as our tongues twined for what seemed to be an eternity.

His hands came up and he fondled my breasts. He cupped them in his palms and rubbed them together. I felt my nipples become swollen and stiff under his hand. “Pinch them,” I begged almost whimpering with desire. I felt his fingers torment my swollen nubs causing my pussy to gush even more.

Lowering his head he sucked on them. “Harder, please suck them harder.” He kept sucking while his hand reached between my legs and he rubbed my pussy lips. I opened my thighs to let him penetrate me. Taking the hint his finger entered my throbbing pussy as he thrust it in and out of my needy cunt.

“Yes, faster! Frig me faster. You are going to make me cum. Oh! That feels so good. That’s it love, make me cum.” I felt as if I was going to explode as his fingers flew in and out of my drenched box. He was massaging all my long neglected pink flesh and I loved it.

I arched my back against him as I felt the wave of excitement carry me. “I’m cumming, please don’t stop. That’s it, Jack. Oh so good.” I lay back in his arms catching my breath. He kept massaging my tits and kissing me. I caressed his face and told him, “That was wonderful.”

Feeling his cock pressing into me again, I stood and held out my hand to him. “Come with me. Let’s go to where we can be more comfortable. ”

He stood up and climbed out. I took him by the waist and led him back inside the house. I felt his hand cup my ass as he walked beside me. We scrambled up the stairs and I led him to the bedroom.

“Just stand there, Jack and let me feast my eyes on you.”

He went to the foot of the bed and stood there. His legs were slightly apart and truly he was a feast for my deprived eyes. His cock was over eight inches long and slightly curved. It was so thick that I was certain I would not be able to touch my finger to my thumb if I held it in my hand. The tip glistened with pre-cum and his balls were hanging heavily below. I was ready to beg if I had to.

I moved closer and pushed him back so that he fell across the bed. I parted his thighs and crawled between them. “It’s your turn just lie back and enjoy,” I told him as my hand reached out for his cock.

My fingers curled around it enjoying its combination of strength and softness. I traced each inch with my fingers discovering every vein and ridge. Drops of pre-cum oozed from the tip and I used my tongue to lap them up and savor the taste of his masculinity. It twitched beguilingly to the touch of my tongue and fingers.

Lowering my head and bending his legs back I explored his scrotum with my tongue. I heard him moan and started to suck gently on his massive balls, they felt as if they weighed a ton. I mouthed them savoring his muskiness and using my tongue to bathe them. From there I slowly licked the length of his erection till I reached his bulbous head.

I wrapped my lips around him and sucked on the head as if it was a lollypop. My tongue licked at his hole and gathered more of his pre-cum that was oozing out. Slowly, I lowered my head engulfing his shaft in my warm, wet mouth. Almost immediately, I could feel him pulsing and I let his cock slide down into my throat. I gagged a few times as my head bobbed up and down, but was determined to have him spill his seed down my throat and into my belly. His pulsing was growing more intense as were the sounds he was making, a combination of growls and moans.

It was time to bring him over the edge. I took my finger and played with his anus. After he initially recoiled, he started to press his hips forward and slowly my finger entered his ass. I reached his prostate and started massaging it. The effect was instantaneous. I felt his cock erupt in my mouth and hot strings of cum slid down my throat. I sucked every drop down without spilling any. Finally sated, I pulled back and looked at his gleaming eyes.

He looked at me with wonder in his eyes. “Meg, that was incredible. This was not my first blow job, but it was like nothing I have ever felt before. I think I’m falling in love with you.”

“Jack, don’t even think that. Today you are my reward for three years of sexual abstinence. You are a wonderful lover. I want you to be in lust with me, but you can’t fall in love with me. I am old enough to be your mother. You will always be in my thoughts but you need to find a person more your own age to find true love.”

“But, Meg, I want to love you.”

“Oh, you sweet lovable boy. I’ll make a deal with you, you can always be my lover and I will give you that. However, save your love for a woman who can be with you for the long run. Almost half my life is now gone and you deserve better. Anyways enough talking, I want your mouth and tongue on my pussy and ass,” I said lying back and spreading my thighs to him.

He sat up and looking down at me he lowered his face to mine and kissed me passionately. His mouth trailed down the soft flesh of my neck and he nibbled his way ever lower. Reaching my breasts he sucked each erect nipple into his mouth and his tongue rasped over my sensitive nipples sending twinges of excitement to my pussy.

He shifted his body to place it between my thighs and ran his tongue between my swollen pussy lips. He kept running it up and down and I ached for him to part them and lick my tender inner flesh. He bent my legs back and parted them wide. I felt his tongue rim my anal pucker and my excitement began to rise at the feel of his velvety tongue probing my ass.

Using his fingers he spread my pussy lips and his tongue slid upward and I felt it reach deep into my pink interior. I was gushing with juices which he lapped up like a starving kitten with a bowl of cream. I felt his mouth and tongue attack my clit which had risen from its hood and he sucked it deeply into his mouth while his fingers curved into my sopping pussy and started to rub my G-spot .

My moans rose in pitch as he frigged and sucked me closer and closer to an orgasm. I could feel my hips thrashing upward to get more contact with his questing fingers and tongue. My moans were rising in intensity as he steadily kept at it. My back arched and my stomach muscles rippled under his assault till finally with a piercing scream I exploded into one of the most violent orgasms I had ever experienced.

He withdrew and came to lie beside me. Cradling me in his arms, he kissed me with unbridled passion.

“Where did you learn to please a woman like that?” I asked as we lay there catching our breath.

“I don’t know. I was just doing what I thought you wanted me to do.” He responded, “Was it good for you?” He questioned.

“That was more than good. It was out of this world,” I answered running my hand down to his cock.

It was again at full erection, both soft and hard within my fist. It felt hot and again there was a dew drop of precum at its tip.

“You’re already hard,” I said with a smile.

“Meg, I want to make love to you. I want to feel my cock buried to the hilt in you.”

“I would like that so much. But I want you to fuck me, Jack. I need to feel you deep inside me. I want it hard and fast.”

He positioned himself between my legs again and spreading my pussy lips introduced his thick cock into me. Slowly he slid into my receptive pussy, stretching me like I had never felt before. He pressed into me until I could feel his balls resting against my ass.

“Jack, I want you to pound me hard and fast. I am fully open to you, fuck me like there’s no tomorrow.”

I felt his hands slide below me and cradle my ass. His thrusts, long and powerful, were reaching all the way to my cervix. Using his muscular hands he lifted my ass towards him as he thrust down into me. I could feel every ridge, every vein rubbing my tender inner flesh.

His fingers curved around my ass and he rubbed my asshole. I immediately started to clamp down on his throbbing cock, determined to milk every ounce of his cum into my waiting pussy. I could feel his cock pulse in me as he came closer and closer to his orgasm.

My gushing pussy milked him with all my inner muscles as I felt the wave of orgasm rise within my body.

“Meg, I’m going to cum,” he yelled.

“Cum love, cum with me,” I said as I felt the stream of his cum flood my hole. I immediately felt my body loose it’s pent up orgasm.

He lay against my body and kept on riding me with a still hard cock from orgasm to orgasm till I finally pulled back from him totally washed out. He withdrew and let his mouth seek my nipples. Slowly we wound down from the ecstatic high we had been on.

He rolled on his side and turning my body so he could spoon me with his hand caressing my breasts, I felt him sink in to an exhausted sleep.

I smiled to myself. Day one of my new life was beginning. I dreamt of what other joys and adventures would be mine. As my eyes closed, I was wondering how long it would be until Jack awoke and took me again.

I finally understood the meaning of the phrase “In Praise of Older Women”. It was not just a matter of a young lover praising us it was also we as ‘Older Women’, who managed to regain our appetite for life, who should praise ourselves. Age was just a number, attitude and spirit defined us.

Edited By JefferyB