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.
