When I was a high school senior I was a skinny, shy kid. Although I didn't have a problem talking and communicating with my guy friends, I clammed up when talking to the girls. As you can guess, it was frustrating when my friends started hitting on and dating the girls. I felt like a fish out of water.
In my high school years, my body changed big time. I have always loved football and decided to play in high school. My commitment to play brought me to the gym for conditioning. I lifted weights four to five days a week, minimum. Within months, there were noticeable changes to my body. I went from skinny skin and bones to a solid muscular frame. My image and confidence in my body changed as well. However, no matter how much my body changed, the shyness I had when it came to talking to girls never changed. It was so frustrating for me.
It's not that I didn't want to talk to them; I just never felt they would like to speak to me, let alone date me. So, I had to settle for fantasizing about them as I jerked off. I have to confess, though, that most of my fantasies were not about my classmates. Most were limited to Mrs. Demarco, whom I called Mrs. D.
Mrs. D was the sexiest woman on earth, in my eyes. She was in her thirties, with long blonde hair, blue eyes, beautiful long legs, big tits, and a fantastic ass. She was a widow. Her husband was tragically killed in a car accident about two years ago.
I can't even guess how often I sat in my bedroom looking out and watching her head off to work. She was always a fashionable dresser and looked sexy going to work. I used to think how she must have had all her male colleagues daydream about her all day; I know I would have. But it was when she went out at night that would blow my mind and my load. She always looked so sexy, not the conservative dress that she wore when off to work. The kind of dress you would see women wear at the club. Short, tight dresses or skirts, revealing tops. Her tits were usually ready to pop out of the tops. I would dream about meeting her at the club. We danced, drank, and had a good time. Which, of course, led us to go back to her place as we fucked the rest of the night. My dream had to move quickly because it never took long before I was shooting my load.
The spring brought some warmer-than-usual weather. My father decided to open our pool early because of that weather, and once it was up and running, he and my mom decided to have a weekend BBQ. That was one thing about our neighborhood: everyone had a pool, and because they worked long hours during the week, they loved their pool parties.
This pool party was like most of them—there was a lot of beer, liquor, soda, and food. The guys all met at the bar to discuss business and sports. I don't mind that part because they always like my opinion on how the team will be and who looks promising since I am now the team captain.
The conversation turned quickly when Mrs. D arrived. All the men stopped talking and just watched as she walked across the patio to where the other women were. She had on a black bikini and a pair of black heels. There wasn't much of a surprise since Mrs. D always wore heels. The quiet was broken when Mr. James just mumbled out, "Just one time, I would die a happy man if I fucked her just one time." All the others agreed with his statement with their head nods. The topic of discussion quickly went back to talking about their stocks when they realized I was still with them.
I knew I was not supposed to be with the men then. I went to the other side of the pool and camped myself out on a lounge chair. I didn't mind, though, because I could lounge on the chair, wearing my sunglasses, and no one could see that I was spending the day looking at Mrs. D.
I could see Mrs. D. was talking with my mom. They kept looking over at me. I couldn't imagine what that was all about. Once they finished, Mrs. D started walking over to me. I was nervous; oh my god, did she catch me staring at her? Is that what she was telling my mom? The nervousness went away as I watched her approach me. Her tits bounced with every step. I was hearing the click of her heels on the concrete patio. Oh no, I could feel my dick starting to grow.
She approached me and sat on the lounge chair next to me. My eyes locked on those tits that were barely covered by her bikini.
"Hi Cory, I have something to talk to you about."
Feeling the anxiety come over my body. "What is it, Mrs. D?"
"Well, Cory, I was talking with your mom, and she said it was okay to ask you this. The weather is getting nicer, and taking care of my property is getting too much for me, so I am looking to hire someone to take care of it. Would you be interested in doing that?
"I will pay you $15.00 per hour, and you can set your hours. I don't want things to get away from me and out of control. Your mom told me you are conscientious and take care of your lawn. It always looks nice so that you would do a good job."
I was taken aback by her offer—something I never expected.
"Please let me know as soon as possible because my grass is already relatively high. If you don't want it, please give me the name of another boy you think might like it."
My mind was racing as I thought to myself. Oh my god, of course, I want it. I can be closer to you. I see you a lot more and get paid for it. I blurted out quickly, "Thank you for the offer, Mrs. D; I am honored you thought of me. I don't have to think about it. I will be happy to do it."
She smiled and thanked me. "That is one less thing I will have to worry about. My lawn mower is in the garage, and gas is in the can next to it."
I told her that, since it was already high, I would be over tomorrow to cut it for you. She was thrilled and thanked me before getting up to walk back to the other women. I watched as her tight ass wiggled as she returned.
I looked around but didn't notice anyone looking, so I got off the chair and went to my room. I was thinking back about how I saw her tits poking out of her bikini and how her ass wiggled as she walked away. You can guess it. I was hard quickly and stroked my cock once again, thinking of Mrs. D. After cleaning myself up, I returned to the party; no one even knew I was gone.
The next day was Sunday; about 11:00 AM, I went to Mrs. D's. I knocked on the door to tell her I was there so she could let me into her garage. The door opened, and there stood Mrs. D. She was wearing a pair of tight blue shorts and a crop top. It was apparent she didn't have a bra on since her nipples could be seen through the light material.
My mouth must have dropped open, and I stuttered as I said, "Good morning, Mrs. D. I'm here to cut your lawn."
She was thrilled that I was there. She took me to the garage and showed me how I could get in if she weren't around and where all the equipment I needed was. I got busy cutting and trimming her lawn. It was a hot day, so I took my shirt off, hoping to get some sun as I worked. The whole time, I thought about how she looked in that outfit and how sexy she was.
As I put everything away, Mrs. D opened the garage door and asked me to come in for a little while. I put on my shirt and went inside. Mrs. D was in the kitchen. She had a cold drink on the table. "Here, Cory, you must stay hydrated in this heat, sit and cool down, and drink." Well, she didn't have to twist my arm since it gave me more time to see that sexy body of hers.
Besides Mrs. D being a beautiful woman, she was also very cool. As I sat there with my drink, she started asking about me. We talked about how I liked playing football, my plans after I graduate next year, and how I am doing in school. I sat there for about an hour talking with her before leaving and heading home. And, of course, I couldn't wait to get up in my room. Yes, once again, there were hundreds of little sperms that sacrificed their lives when I blew a massive load into a tissue. I hope they realize they died for a good cause.
Mrs. D gave me a list of things she would like to have done. I would go and complete the task whenever I had time. I wanted to go and do them when she was home because she wore some skimpy clothes, and I loved that. Some days, I felt like I hit the lottery when she was by her pool in her bikini.
It was late on a Friday, so I went to Mrs. D to cut her lawn. I didn't bother her since I now knew where everything I needed was. It was hot, so I took my shirt off and started mowing. I cut the front and went to the back. I looked over, and Mrs. D was sitting at her patio table. I looked over, and she waved at me, so I waved back and finished my job. Once I was done, I walked back to the pool area and apologized to her. "For what," she asked.
"I didn't think I would interrupt your relaxing time."
"Oh, don't be silly, Cory. You didn't interrupt anything."
She had a picture of cold water on the table and poured a glass. "Please sit, Cory, and join me for a while."
I was looking forward to our little chat sessions after I was done. I sat on the chair across from her. I had not put my shirt back on since it was a hot night. Mrs. D was wearing a floral sundress with a low-plunging neckline. It's always a plus to enjoy our conversation and get to see her sexy body as well.
We discussed our week, and Mrs. D asked me why I mowed her lawn tonight. "Don't you have a date?"
I looked away and was embarrassed when I mumbled, "No, I don't."
"You mean you don't have a girlfriend," she asked.
"What is wrong with the girls in that school? I would have thought you would fight the girls off with your good looks and solid body." The first thought that ran through my head was she thinks I have a sexy body.
I went on to tell her that I was timid and not very good at talking to girls. Mrs. D sat forward in her chair and took hold of my hand to comfort me. When she did, I was able to look right down her dress. Her tits were in full view. I felt my cock starting to react. Then panic set in as I didn't want Mrs. D to notice. I squirmed and moved, hoping she didn't notice. She was talking, and to be honest, I had no idea what she was saying since I was so focused on trying to hide my hard-on. I couldn't take it anymore. I blurted out, "Mrs. D, I must go home." I jumped up, trying to hide my hard-on as I did, but I don't think I was successful. I walked to the gate, but before I left, I turned back to look at Mrs. D. She smiled at me and waved goodbye. I waved back and ran home.
When I got home, I needed to take care of the essential things first. So, after I jerked off, I lay there on the bed thinking. There is no way she didn't see my hard cock poking into my shorts. I didn't know what to do, but I also knew there was nothing I could do. If she saw it and wanted to fire me because of it, there was nothing I could do. I just didn't know how I would tell my parents that I was fired because I am a horny degenerate, and my cock got hard when talking to Mrs. D.
Over the next week, I went to Mrs. D to complete some tasks, but she was at work when I was there. It wasn't until the following weekend that I went to mow the lawn again. I got the lawn mower out and mowed and trimmed. It was my first time working since I ran home because of my hard cock. Mrs. D never came out or was in her yard doing something. I remember thinking to myself, I knew she saw me. That is why she is not out here. She is hiding; she knows how much of a pervert I am.
I was near finishing when the sky darkened, the wind kicked up, and it started thundering and lightning. I watched Mrs. D leave the house and head to the patio. She frantically gathered the cushions off her lawn furniture before they blew all over the neighborhood. I put the lawn mower away and ran over to help her. The skies opened up in seconds, and it started to pour.
We were drenched by the time we got the cushions into the garage. Mrs. D thanked me for the help. When I turned to look at her, my eyes almost popped out of my head. Her tank top was soaked, and her nipples were visible since she didn't have a bra on.
She reached out and held my hand. "Come inside, Cory, and dry off before you catch a cold."
I followed her like a lost puppy dog. I could feel my cock already rising to attention. She grabbed two towels and moved over to me, "You better take your shirt off, Cory, so you can dry off and warm up."
Mrs. D took hold of the bottom of my shirt and raised it over my head. She then grabbed a towel and started toweling me off. As she stood in front of me, drying me off, her tank top still soaked and her nipple poking out, I could feel my dick getting even harder. "Oh god," I thought. There is no way she isn't going to notice my dick sticking straight out. I started to feel panic come over me.
Then she stepped back a step or two, and without notice, she removed her tank top. She stood in front of me topless with her huge tits wet and glistening right in front of me. "I'm chilled to the bone; you don't mind, do you, Cory?"
I looked down and away, feeling embarrassed. "UM, no, I don't mind, Mrs. D."
It's not much different than being in a bikini top, and I see you always looking when I am in one of them. I felt myself get even more flustered. Before I could even deny it, she gently touched my face and told me it was okay. She liked it when others checked her out. It was a compliment that they think I am pretty.
"You do think I'm pretty, don't you, Cory?"
Still looking away and down, I just mumble, "Yes, Mrs. D, I do."
She stepped closer, put her fingers under my chin, and pulled my head up to look at her. Cory, "I am a little worried about you. I want to help you overcome your shyness and feel more comfortable. I want to show you the enjoyment you can have if you come out of your shell. Wouldn't you want to enjoy everything, Cory?"
With Mrs. D still holding my chin, my eyes looked into the sexiest brown eyes I have ever seen, and I whispered, "Yes, Mrs. D, yes, I would want that more than anything."
You promised me you would never tell anyone, right, Cory? I tried to look away, but her fingers were still under my chin. She wouldn't let me. "I promise, Mrs. D."
She went on to tell me that she was so much in love with her husband, and it crushed her when he died. She doesn't want another man and doesn't want to date anyone, but she went on to say how she hates her bed being so lonely. She explained that she still has sexual needs, and she thought that I could help her with those needs, and in return, she could help me be more comfortable with others.
I couldn't believe what she was saying. She said, "I see you watching me, Cory; you have naughty thoughts about me, don't you? I tried to look away.
"No, Cory, look me in the eyes and share that with me."
It took me a while, but with her encouragement, I went on to tell her how I would sit in my bedroom, watch her leave, and think about making love to her. I was embarrassed, and she saw that I was. She told me not to be and told me I was no different from anyone else. She asked me if I ever noticed the men in the neighborhood and how they looked at me. "They have those same thoughts, Cory."