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My Summer Job

Category: Mature
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The summer after my sophomore year of college began as a boring one. I was taking summer school classes to fulfill a few perspectives so that I could concentrate on my major courses during my last two years of school. I had a work-study job during my time in summer school so the rent wasn’t a problem at the time, but once summer school was over it was different story. I had no classes to go to, no job, no friends to hang out with (everyone I knew went home and my roommates were both still in summer school and had jobs), and nothing to do that would fill that empty void—that is until one fateful day in early July.

On one of my many days of job hunting I came across a flyer that requested help with yard work. There was a number to call for more information so I pulled a pin from my pocket and jotted the number down on the inside cover of the folder in which I carried my résumé’s. I got back to my apartment later on that day around six o’clock, went to my room, grabbed my phone beside my bed and made the phone call. I was greeted by a soft, grandmotherly voice:

“Hello,” she said.

“Hi. Yes my name is James and I’m calling about a flyer requesting help around the yard. I would like a little more information on the job.”

“Oh yes, I didn’t think anyone was ever gonna call about that.”

“Well I’m pretty good with my hands and I don’t really mind helping someone around the house; and the fact that I really need a job makes it even more appealing,” I joked.

She chuckled and began to tell me more about the job. “Well, my name is Maddie Ashton and you would basically be helping me out around the house. I really need someone to cut the grass once a week or so, and trim the bushes in the yard. There are a lot of things that I want to do around the house and I just need someone to help me from time to time.”

“Yes ma’am, I understand that completely. The work won’t be as strenuous with two people doing it instead of one. I have a question though,” I continued, “exactly how many days a week would I have to come over?”

“Oh we can work out a set schedule later on, but I will pay you seven dollars an hour.” That was all I needed to hear. So we set up a time to meet the next day, said goodbye to each other and that was it. I had finally found a job.

The next day I caught the bus over to her house. She lived in a nice quiet area. I walked up to her front door and knocked. I was greeted by a sweet conservative looking woman. She appeared to be in her late fifties or early sixties, about 5’4, and fairly plump—I’d guess about 220 lbs. She wore glasses and her hair was short and curled and fairly gray. To sum it up, she looked like a grandmother. Now being a very horny college student who hasn’t gotten laid in a while, I’m talking years here, I tend to involuntarily “check out” a lot of women that don’t really fall into what society deems attractive. She had on a short-sleeved housedress. The buttons at the top managed to contain a very large pair of breasts. Despite the distraction I forced myself to make eye contact.

She greeted me with a welcoming hello. I told her who I was, then we formally introduced ourselves and she invited me in. She told me to have a seat in the living room and asked if I wanted anything to drink. I asked for a glass of water and she shortly returned from the kitchen with two glasses of water. We talked more about the things she wanted help with around the house, and how her husband had died and how she had given up on anyone answering the ad. I told her that the job sounded great and we decided I would start tomorrow. Before I left, though, she wanted to show me around the house. As she led me around the different rooms she wanted to change, I noticed that she had a big soft pillowy looking ass. The way it swayed under her housedress was almost mesmerizing. She took me in one room and told me she wanted to make it into her sowing room.

“I enjoy sowing and it would be nice to have a sowing room with all my sowing equipment in here. My own private sowing room.”

“That would be nice” I commented.

“Yeah, and I want to paint this room and—come over here to the closet with me—and clear out this closet, especially, this mess on the top shelf.” As she said that, she began tugging at a rather large box on the top shelf of the closet. The more she pulled at the box the more it looked as though it would fall, so I moved up behind her and reached over her to grab it. At the same time, I was forced to rub my crotch up against that soft ass of hers. As I pulled the box down my crotch was thrust forward causing me to lightly hump her ass. It wasn’t intentional on my part, even though I enjoyed it and really took my time getting that box down. Naturally, my dick began getting hard—I mean her ass felt really nice pressed up against me. I couldn’t help it. The most surprising thing, though, was that she seemed to be pressing back against me, meeting each of my thrusts. I reluctantly backed away after she got a better hold on the box and got it down by herself. She bent over and set the box down on the floor, giving me a great view of that big round ass. I had to quickly put my hands in my pockets to try and hide my erection. I’m not hung like a horse or anything. My penis is about the average six inches or so, but still very visible through a pair of jeans when I’m hard. We talked a little more as she walked me to the door and I told her I would see her tomorrow at 9:00 a.m.

I arrived at her house the next day around 9:00 like I said. Ms. Maddie, as I called her, was dressed differently today. She wore a light-blue, short-sleeved, button up shirt and a pair of tan Capri pants. The few buttons at the top of her shirt were open showing a little bit of cleavage, and the bottom of her shirt seemed to hug her ass, which I find sexy as hell. I just watched her ass sway as she guided me around her house and showed me what she wanted me to do. She created quite a bit of stirring in my pants.

I cut the grass that day and trimmed the bushes in her yard. Once I was finished with everything, I went to the flowerbed at the front of the house where she was working to tell her I was finished. As I approached, she just stared. Well, let me describe myself to give an idea as to what she was staring at. I’m a tall, slim guy weighing about 177 lbs. I work out quite often so my body is fairly toned. I had taken my shirt off earlier because it was pretty hot that day.

“Ms. Maddie, I’m finished with everything. You need any help with anything else?”

“Um, oh no, James, that’s it for today,” she replied looking up at my abs and chest.

“Are you sure?” I asked.

“Um, no I don’t, I mean yes that’s all for today. You can go home if you like.”


That was basically how it went for a few days. I would show up and do whatever work she had for me to do and leave; but as time passed we became friendlier and more affectionate with each other. She began to cook dinner for me after my work and even allowed me to take a shower when I was really sweaty. Then, things really began to get hot.

On one hot day after I finished all the work Ms. Maddie had for me to do, I took a shower and changed into the gym shorts and t-shirt that I brought with me. After I got dressed in the bathroom, I went into the kitchen where Ms. Maddie was cooking dinner.” Since she had just taken a shower before me, all she had on was her bra and panties and a robe.

“So whatcha cookin’?” I asked as I walked up behind her and kissed her on the cheek, making sure to rub up against her plump ass as I did.

“Oh, mashed potatoes and steak.”

“Smells pretty good.”

She finished a few minutes later and we sat down at the table and ate dinner. Afterwards we sat down and watched television together. I usually catch the bus home, but Ms. Maddie said she would take me and insisted that I stay and watch the rest of the show since we were both really into it. So we sat next to each other on the couch and finished watching TV. A beer commercial came on that showed some guy in a club trying to pick up some model-looking chick.

So Ms. Maddie chuckled and said, “If that’s what men are going for nowadays, it’s no wonder I haven’t got a man.”

“That’s not true,” I said, “that girl is so fake. It’s like she was manufactured in a factory. There’re thousands of girls out there like her.”

“Yeah, but she looks like a model. She’s young and beautiful and there’s not an ounce of fat on her. I’m old fat and ugly. No guy wants and old lady like me.”

“No,” I protested, “You’re a beautiful woman.”

“It’s sweet of you to say that James, but I look in the mirror everyday and I know what I see.”

“Well, I see a beautiful women.”

“That’s sweet, but I know I’m fat.”

“So, you have a few extra pounds. It’s in all the right places and I know for a fact that a lot of men find that very sexy.”

Then I saw something in her eyes after I said that. Her eyes seemed to twinkle as she looked at me.


“Yes. As a matter of fact, I think you’re very attractive. You are a very sexy lady.” And those words were the key that opened the door to one of the greatest experiences of my life.

Ms. Maddie leaned over and kissed me on the cheek and said, “That’s so sweet.”

“Not as sweet as that kiss,” I quickly shot back. “Let me get another one.” She laughed at that and again kissed me on the cheek. “Can I have just one more,” I asked through a giggle. She more than willingly complied and went in to give me another kiss on the cheek, but as she did I made my move and kissed her on the lips. It was a light peck but it was enough. Ms. Maddie was momentarily stunned. I wasn’t about to let this chance get away though, so I quickly gave her another peck on the lips, and then a third. On the third peck she returned the kiss and we continued to give each other a series of light smooches on the lips. Then, I held the kiss longer and pulled away and looked directly into her eyes. She understood then that this just wasn’t friendly affection. Our relationship had grown into more. I leaned in and kissed her again, this time showing her how much my affection for her had grown. I pulled back and looked into her eyes again.

“Ms. Maddie I think you’re one of the most beautiful women I’ve ever seen. I wanna show you how I feel about you.” I leaned in and kissed her again, this time I used my tongue to part her lips. We sat there kissing on the couch, our tongues imitating the lovemaking act that we would soon indulge in.

“Lets go to the bedroom,” she said to me. I stood and pulled her up from the couch. I held her hand and led her to the bedroom. We stood by the bed and I pulled her to me in a tight embrace and kissed her once more. I rubbed her back and moved my hands down to that wonderful bulbous ass. As I kneaded her cheeks, I could feel the blood rushing into my member and I pulled her closer to me pressing my erection into her soft belly. I reluctantly broke our kiss as I opened her robe and marveled at her body as her robe fell to the floor. She had on white panties and a massive white bra that supported two of the hugest breasts I’ve ever seen. Most of her body was pale but she had a tan v above her breast from being out in the sun. I took a step back, sat on the edge of the bed, and took off my own shirt.

I motioned for her to come to me and she stepped over. I placed my hands on her hips, and then slid them up to her bra-clasped breasts.

“They’re wonderful,” I said. “Can I see?” Ms. Maddie didn’t say a word; she just undid her bra and let those massive breasts fall out. They were absolutely fabulous. They sagged on her belly, but they were still soft and beautiful. The nipples were pink and stood out about an inch. They were surrounded by pink areolas. I reached up and grabbed her heavy breasts and brought them to my mouth. I sucked and licked one nipple, then the other. I greedily pulled both of those massive udders to my mouth and sucked the two nipples at once. She rolled her head back and let out a sigh as I sucked and massaged her wonderful titties. At the same time, I let go of her breasts with one hand and stuck my hand in the waistband of her panties to pull them down. She immediately grabbed her hanging breast and continued to feed it to me. Once she stepped out of her panties, I let my hand slide up her inner thigh. She widened her stance a little and gave me access to the wet mound between her legs. She let out another sigh as I rubbed her pussy.

“Lay down on the bed,” I told her. She lay on the bed and I got down on my knees between her legs. I slowly made my way up to her cat, planting kisses on her thighs as I moved along. The enticing aroma of her juices pulled me towards her huge slit. It was covered with a graying bush and literally dripping wet. Ms. Maddie rested her meaty thighs on my shoulders as I began to eat her out. I sucked on her juicy pussy lips and then stuck my tongue in her sweet hole. Then, I saw her little nub sticking out demanding some attention. I licked her clit, sending shudders up through her body and feeling her thighs tighten around my head. As I continued to suck on her clit, I brought up my hand and stuck a finger in her pussy. She let out a moan of approval and began to writhe around on the bed.

“Ohhh, don’t stop.”

I slowly finger fucked her pussy and licked her clit as her moans grew louder.

“Ugh, Ugh. Lick me. Lick me. Ohh, that feels so goooood.” She began grinding her pussy against my face. Her moans were very loud now and came from deep inside her. I could tell she was going to cum any second as I continued to suck on her clit. Suddenly, her thighs tightly clasped around my head and she began bucking against my face.

“Ohhh, I’m, I’m…ohhh.” She tried to tell me she was cumming but it was lost in her moans of pleasure. A flood of her juices flowed from her pussy and I eagerly lapped it up. My dick was rock hard now and I just had to have her. I stood up and pulled my shorts and boxers down as she lay there taking in all of my body with her eyes. I climbed on top of her and felt my hard dick nudge the opening of her pussy.

“I want to feel you inside me, James.”

“I want to be inside you,” I replied. We kissed again and she bucked her hips up trying to get me to enter her. I broke our kiss and lifted myself above her. She reached between us and guided my dick into her wet puss. She moaned as we both laid there, a part of each other. Damn, it felt great. She wasn’t tight, but she was very wet from her orgasm and hot as hell. I began to slowly pump into her. She moaned again. My rhythm began to pick up: in and out, in and out, my cock sloshed in her pussy, as her moans grew louder. I could feel my balls beginning to tighten.

“Aww, Ms. Maddie, I’m gonna cum.”

“That’s it baby. Go ahead and cum in me.” I held back as long as I could but I couldn’t take it anymore. The feel of Ms. Maddie’s hot pussy engulfing my cock overcame me and I came. Spurt after spurt of my spunk filled her up. The feel of me cumming inside her sent her over the edge and I felt my cock being bathed in her juices as she came for the second time that evening. I collapsed on top of Ms. Maddie, my sapped member still inside her.

“God James, I haven’t felt that in such a long time.”

“Neither have I,” I said as I rolled off of her.

A few minutes passed and she asked if I wanted her to take me home now.

“No. I think I have a little more work to do around here.” She smiled then leaned over me and gave me a very passionate kiss.

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