It Pays To Be Helpful
written by:
oppy-n-rose

I was running the lawnmower up and down the side of my neighbor's house, trying to get the lawn cut before she got home from work. I wanted to get it all cut before she showed up and tried to pay me. There was no way I could accept her money because I knew that she was having a tough time getting by. She had an office job but had recently taken a huge step in her life. A woman who was very close to her had suffered some personal issues and could no longer care and maintain her two children. She was forced to put the kids up for adoption, and my neighbor had decided to adopt them. She was in her late 20's when she adopted the two boys and I knew that it was a huge step for her. Most women in there 20's would love to be out partying and hitting the clubs. Instead, she had done the noble thing and adopted the two boys, and this way they could still be close to their mother. Basically, she became a single mother of two and I knew that she was barely getting by. I had taken it upon myself to go over every other week and cut the lawn for her because there was no way she could afford a landscaper. She always tried to pay me whenever she saw me, but I would never take it. I knew she needed the money for more important things and I didn't mind helping her out. After all, like I said she was in her late 20's, had taken pretty good care of herself, and had a real good-looking body. Her tits were the size of two nicely rounded cantaloupes, and she had a nice full round ass. There were plenty of times that she would be outside playing with the kids, and I would sit on my porch with a cold beer and enjoy the view.

I was almost done with the lawn, when I looked up and saw the bus stopping at the corner. I saw her come off the bus and she came walking down the street pretty quickly. She seemed to be in a hurry as I waved to her. She waved back and ran into the house, and within a few minutes, she ran back out and took off up the street in the opposite direction. I continued mowing the lawn, but watched that ass as she walked down the street. I then realized that she was rushing to get to the daycare that was at the end of the street. I looked at the time on my phone and figured that it was probably closing time at the daycare. Sure enough she hurried into the daycare and soon emerged with the two boys in tow. When she finally made it back to the house, she looked like she was worn out. She walked over to me and like usual offered to pay me. I quickly declined and asked her how she was doing. She told me that she was exhausted from all the running around everyday. I complimented her and told her that it took a strong woman to do what she did and she thanked me. She told me that it wasn't easy because she barely got home in time everyday to pick the boys up from daycare. The daycare closed at six and if she didn't make it to the place before six, then she would be stuck paying extra. I felt bad for her and asked her if there was any way that I could help. She thanked me again and said that there really wasn't anything that could be done and she hoped to try and work something out at her job and hopefully get home a bit earlier. I told her that it sounded like she was having some rough times and she just responded by saying that hopefully things will get better.

As we talked, I got a bright idea and offered to help her. I told her that I got home every day from work around four and that it wouldn't be a problem to run down and pick up her boys for her. She quickly told me that there was no way that she could expect me to do that. I told her that it was no problem because whenever I came from work, I would just spend my time outside in the yard anyway. I told her that I could pick up her boys and bring them over and let them play in the yard. I had a basketball hoop that they could play with and they could even bring over some of their stuff and keep it in my shed. She told me that there was no way she could impose on me like that and I told her once again that it wouldn't be any problem whatsoever. I told her that this way she wouldn't have to rush home after work. The boys could play in my yard, until she got home from work. She asked if I was sure about all of this and I told her that I was positive. She thanked me over and over again, and even gave me a big hug. I was just happy to be able to help. That's what I was taught when I was growing up. She thanked me once more and asked me if I could meet her in the morning, before she left for work so that she could take me to the daycare and inform them that I would be picking up her kids. I told her I would see her in the morning and the three of them headed off into the house. I finished up mowing her lawn and then headed over to my house as well.

The next day I went with her to the daycare and we worked everything out. That afternoon, I got home from work and picked up her boys and brought them over to my house. They had a great time spending the afternoon playing basketball in my yard for a bit. They had bought a few of their own toys, and spent some time playing with those as well. Their mother eventually arrived to pick them up and saw how much fun they were having and thanked me again. I told her to stop thanking me and said that I would see everyone tomorrow. The next few weeks were pretty much spent the same way. I would come home from work, pick up the boys and they would have fun playing out in my yard, until their mom came to get them. Every now and then, she would offer me some money for watching the kids and I would always deny her. I kept telling her that I didn't want her money because I knew she needed it for more important things. I would always tell her to take whatever money she was going to give me and put it into a bank account for her kids. She was always very grateful for my help, but insisted on giving me something. I decided to push my luck a little bit and told her that if she really wanted to give me something, then I would love for her to go out and get something to eat with me. She smiled and quickly accepted my offer. I told her to let me know which day was good for her and I would take her to a nice place that I knew. She told me that she would call her mom and have her watch the kids on Friday night, and then we could go. I said okay and she was soon on her way with her boys.

Friday night came and I was a bit excited to be taking her out for dinner. Of course I couldn't expect too much, but hey a guy could fantasize. I threw on some khakis and a nice dress shirt and then headed over to her place to see if she was ready. I rang the doorbell and was stunned by what I saw. She opened the door wearing a black v-neck dress that showed a bit of cleavage and cut off just above her knees. I was at a loss for words as she greeted me and I quickly managed to tell her that she looked stunning. This was definitely a side of her that I had never seen. Usually you would see her out there in shirts and even tank tops, but I never saw her like this. I did my best to hide my excitement and we were soon on our way to the restaurant. The place was just outside of town so it didn't take us long to get there. We arrived at the place and made our way inside to get a table.

The waiter made his way over and we started off with some appetizers and a bottle of wine. While we waited for our food, we chatted about anything that we could think of. I asked her how things were at her job and she told me that it had definitely gotten easier ever since I started picking up her kids. I told her that I was just trying to be helpful and she responded by telling me that I didn't know how much she really appreciated all of my help. Our food eventually came and we enjoyed the meal, as well as each other's company. Eventually, we finished our dinner and after I paid the bill, we made our way out to the car. I began driving, making my way towards the house. She complimented me on the restaurant that I had chosen and I asked her if she enjoyed. She told me it was great and appreciated being treated to a night out. I told her that I was glad to hear that and that we should do it again. She smiled and told me that the night wasn't over just yet. I wasn't sure what she meant and just continued driving. That's when she began looking around and then instructed me to turn down one of the side streets. I did as told and she took off her seat belt. She looked around once again and then proceeded to get on all fours on her seat. I asked her what she was doing she just smiled at me and told me that she had noticed the look on my face when she opened her door, and since I wouldn't take her money, she wanted to show her appreciation in another way. Before I could say anything, she reached over and began rubbing my crotch.

My cock began to come to life, as she slowly unzipped my pants. She reached in and grabbed my cock and pulled it out. I did my best to focus on the road, as she began slowly stroking it. She then took another look around and then lowered her mouth to the tip of my cock and began taking it in. She tightly wrapped her lips around my cock and began bobbing up and down on it. As she did this, I took my free hand and ran it down her back, towards her ass and gently began to squeeze it. She continued bobbing up and down on my cock and I decided to get a bit bolder. I slowly ran my hand from her ass, underneath her, to the opening of her dress and rubbed her cleavage. She stopped sucking on my cock and sat up for a second and reached into her dress and pulled both of her tits out. I did the best to keep my car on the road, as I stared at those massive tits. They were everything that I had ever fantasized about. She took my free hand and placed it on one of her tits and then I softly began squeezing it. She then lowered herself back onto my cock and began bobbing up and down on it once again, as I reached underneath her and squeezed each of her tits. Within a few seconds I began to tense up and told her that I was going to cum. She just kept sucking on my cock and I soon blew a huge load down her throat, which she swallowed. She bobbed up and down on me for a bit more and licked my cock completely clean. Once she had sucked up every drop, she pulled me out of her mouth and sat back down on her seat. She smiled and asked me if I liked it and I told her that she was amazing. I continued driving with my cock still out of my pants and I could feel myself coming back to life. She noticed and reached over and started stroking it again, while telling me where to drive. She ended up guiding me to a parking lot in the back of an apartment building, where there was a bunch of cars. She told me the park the car and she quickly jumped in the back seat. I just did as told and soon joined her in the backseat.

Once we were both back there, we began kissing each other like crazy, running our tongues in and out of each other's mouths. I then ran my lips down her neck, to her tits and took each one of them in my mouth, while squeezing them and burying my face between them. She stroked on my cock and lowered her mouth back down to it. She licked the tip with her tongue and proceeded to lick the entire thing from top to bottom, getting it nice and wet. Once I was wet enough, she lifted her dress and took off her panties. I quickly realized that I didn't have a condom and mentioned it to her, hoping that it wouldn't end our fun. She just smiled and told me not to worry about it and pushed me back against the seat. She then climbed onto me, straddling my crotch and guiding my cock into her warm wet pussy. She lowered herself down onto my cock and I couldn't believe how amazing it felt.

She began lifting herself up and down on my cock as her tits bounced around in my face. I buried my face between them and squeezed them tightly as she picked up her pace and began moaning loudly. As I went to place my hands on her hips, she pushed them off and told me that she wanted to do all the work. I then laid back against the seat and enjoyed the site of her bouncing up and down on my cock. I couldn't believe that I was in the backseat of my car banging my neighbor. I'm sure plenty of guys on the block had fantasized about this, but I was actually doing it. She bounced up and down on my cock at a moderate pace, allowing me to enjoy the feel of that wet pussy. She would lift herself up until just the tip of my cock was in her pussy and then lower herself back down quickly. Little by little, she picked up the pace and really began riding me good. She even arched her back so that her tits were pointed straight out into my face. I enjoyed her nipples as she fucked me.

Within a few minutes, I felt my balls churning and told her that I was going to cum. She picked up her pace and began bouncing up and down on me even faster. We both began moaning and I soon felt myself explode inside of her. I flooded her pussy with a ton of my hot cum. She continued bouncing up and down on me until I had shot off every drop that I had left. Once she was done, she climbed off of me and sat on the seat next to me as we both tried to catch our breaths and slowly redressed ourselves. We eventually made our way back to the front seat and began driving back home. I thanked her for an amazing evening and she told me that she still owed me many more payments...