Growing up in a small town can be tough at times. I was a jock but not a popular one. I played football where I started as middle line backer, I wrestled, and I participated in track to stay in shape for football and wrestling.
I was the biggest kid in my school. My freshman year I was 6' and weighed about 240. Of course I wasn't a muscle head but I was in good shape and was strong from working summers for my neighbor on his farm.
I also wasn't very popular because I liked to keep to myself. I was friends with everyone but was never the guy that the high school girls would pine for. I got invited to all of the parties but never really went because I always felt out of place. In my town everyone knew who you were and who your family was.
My father was an asshole and he beat me until I turned 17 and then I ended up kicking his ass and from then on the beatings stopped. The repercussions from that were I was kicked out of my house. I ended up homeless for a few days until my grandparents said I could stay in their fishing cabin.
Of course word got around quickly about what had happened and I was looked at differently. People stopped talking to me. I wasn't popular to begin with so it became much worse after that. Small town life sucked for me then.
I was determined to stay in school and graduate. I loved playing sports since they were a big part of my life so I devoted as much of my time as possible to them but I had to eat so I needed to find a job.
As I said my town was small. Thirty miles away was a much bigger town with many job opportunities. I ended up getting a job at a farm store in the bigger town. The store was open until 10pm and then after the store closed select few were scheduled to stay and restock shelves. Everyone that stayed usually finished up around 1am and then went home.
I spoke to the manager and told him my situation and asked if I could stay with the late crew and restock because I really needed the money. He felt bad for me so he said yes which was good for me.
One of the people that worked the late shift was a woman named Michelle. Her and I always seemed to work the same days so we became very friendly. We talked everyday about life and what we wanted out of it.
Michelle was married and had 2 children. She was 29 and extremely good looking with long blonde hair always pulled into a ponytail and deep blue eyes. From the first time I saw her I imagined what she looked like under her clothes. She always wore tight jeans and tight t-shirts to work. She looked like she weighed about 125. I guessed she was around 5'7. I guessed her breasts were maybe 34C but I wasn't sure and her ass was very well rounded and looked really tight in her jeans.
As I said before I looked older than I was because of my size so Michelle thought I was at least 18 since I was working the restocking shift with her. After the store closed and the restocking began her and I always made sure we were paired together because we had become good friends over the months that we worked well together.
One night after we had been working together for a few months the night shift supervisor pulled everyone together and told us that we were done for the night. It was only 11pm so we were all surprised. We all went to the time clock to punch out.
"Are you heading home Michelle?" I asked.
"I don't know. Everyone will be asleep and I am not tired since we are normally here until one. I think I am going to drive a round a little and see what is going on." she replied.
"What are you going to do?" she asked.
"I'm probably going to head home and get some sleep." I replied.
"How about we get some beer and go over to the park and hang out for a little while?" she asked.
"Sounds good to me." I replied.
We walked outside to our vehicles. Michelle knew I wasn't old enough to buy beer so she said she would get the beer and meet me at the park pavilion in 20 minutes.
"See you there." I replied.
As I got in my truck and watched her drive off I was nervous but extremely turned on thinking that Michelle and I would be hanging out together having a beer and talking. I didn't think it would go anywhere except for friendly conversation but I was hoping.
I had been at the pavilion for about 15 minutes when Michelle pulled in beside me. As she got out of her car I noticed two things. First was she had changed her clothes from jeans and a t-shirt to a pair of pink spandex work out booty shorts and a white sports bra which accentuated her beautiful breasts.
Michelle walked over to my truck and crawled up inside handing me the beer. I grabbed two beers and set the rest of them in the back seat of my truck.
I couldn't stop staring at her. She was beautiful and it turned me on very much. Seeing her wearing such revealing clothing started making my cock hard.
"I had to change out of my work clothes. It is such a nice night and I was so hot in them. I hope you don't mind." she said.
"Not at all. You look amazing!" I replied.
"Thank you. That is the nicest thing anyone has said to me in a long time." she said.
"I doubt that Michelle, you are gorgeous!"
Michelle blushed a little but said thank you as we started drinking our beer. We talked about different things. I asked about her married life and about her kids. She asked me about my family and about what my plans were for the future. The whole time I kept staring at her amazing body. The way the sports bra lifted her breasts and how I could see her nipples sticking out hard. I could also see that her spandex shorts were pulled up tight against her pussy lips and I could see there outline through them.
I was entranced with how hot she was which started to make my cock grow. My cock is big. It is a little over 9" long and it is almost 3" around. It was expanding down the right leg of my pants the more I looked at her. I was afraid she would be able to see it if she looked. I was still a virgin. I had had a few hand jobs in school from younger girls. They made me cum by jacking me off but wouldn't let me fuck them because they were afraid I would hurt them.
Michelle asked me about my home life in which I explained what had happened to me. She was listening intently and as I finished she reached her hand over to pat my right leg and tell me how sorry she was. At that moment when she touched my leg she felt my hard cock. She pulled her hand back quickly and looked at me.
"What was that?" she asked.
I didn't know what to say. I just looked at her more embarrassed than I had ever been.
"Is that your cock?" she asked.
"Yyess, I stammered. I'm sorry. Seeing you in your sports bra and booty shorts made me hard and I was hoping you wouldn't notice." I replied.
"Oh my god John, your cock is huge!" she replied. "I want to see it!"
I was so nervous and embarrassed that I couldn't speak. I didn't know what to do. Here was this gorgeous MILF sitting next to me and she wanted to see my cock.