Paying Me In Different Ways
- 8 months ago
- 12 min read
- 12,715 views
About three months ago, as I was finishing up a job, I heard a female call out my name. I looked around to see who it was, and noticed the woman across the street from the house where I was working, standing on her porch, waving to me. Her name was Jessica, and I had done work at her house several years ago. Unfortunately, it didn't work out because her husband was a real cocky guy, whom I later came to find out was shady as hell. He owed me some money, and never paid me, which is why I stopped working on their property. As I saw Jessica waving at me, I started walking towards her, wondering what she wanted. I crossed the street and met her on the sidewalk in front of her house. The first thing I noticed as I approached her was that the house was a mess, with the grass almost knee-high. It was odd to see the house that way because they always took really good care of it. The husband ran a bunch of businesses, and always had people working around the house to keep it in order.
Once I was next to her, she greeted me and asked how I was doing. I told her I was great and asked how she had been. She looked down at the sidewalk, and softly said that she wasn't doing so well. I asked her what was up, and she told me that a lot of things have happened since I had last worked on the property. I looked at her and asked if she was okay, and she said that she was going through a rough patch and started to talk about her husband and how she was divorced. I was shocked, as I had no idea about that. I worked across the street from her house, once a week, and had no idea they had split. His truck was still in the driveway, which made it confusing. As I asked, what had happened, she began to say something about him being in jail, and I quickly cut her off. I told her that it sounded like some private stuff, and that she didn't really have to tell me. She insisted that she wanted to because she needed to talk to me, so I decided, to listen to her, but not in front of the house. I told her to meet me on the southern end of town, where there was a big park, with a bunch of soccer fields. I said I would be waiting in the back corner of the park, and for her to meet me there at lunchtime. This way she could talk to me, and none of the neighbors would know or see what we were talking about. There were a lot of nosy people on the block and they didn’t need to hear about her troubles. I didn't want to go into her house and talk, because I knew her kids were there and I'm sure that it probably wasn't a great subject to discuss with them present. She agreed to my plan, and said that she would meet me at lunch. With that, I went back across street to finish up what I was doing, before heading to the park.
As I drove across town, I thought about what she had mentioned, and a part of me was happy that she had split from her husband. Like I said, he was a cocky businessman, who was a bit older than her. He was making money with his businesses, and he thought that he was better than everyone because of it. She was blinded by the money, and married him, against her family’s wishes. I think it got to the point where they disowned her and stopped talking to her because they couldn't stand him. I wasn't surprised, because he was a real scumbag. I had actually felt bad for her when I first met her, because she seemed like a sweetheart who was lost. Unfortunately he knocked her up, having five kids, so she was stuck at the time. She was a good-looking woman, and I had no idea what she saw in him, besides the money.
I arrived at the park a short time later, and parked my truck and trailer, while waiting for Jessica to arrive. Surprisingly, she arrived a short time after I did and parked next to my truck. She got out and walked over to where I was standing, and we greeted each other once again. We then began to walk, towards the back corner of the park where there were marshes and wetlands. I used to go back there when I was a kid and ride my bike through the tall weeds, and along the waters edge. It was a spot where a lot of high school lovers would sneak to after class to hook up because it was such a secluded area. Nowadays, it was deserted and nobody ever really went back there. I would walk around back there whenever I needed to clear my head because it was a quiet place.
We walked along and began to chat, about the last several years. She told me that a lot had happened and began to break it down. Apparently, her husband, who I always suspected of being shady, was ripping off a lot of clients, and that's why he always had so much money. I guess it finally caught up with him one day, and he ended up getting arrested. He went to court, and was ordered to pay back all the money, on top of fines, and also got jail time. Throughout the process, she got tired of all the crap, and divorced him, which was probably the best thing she could have done. Unfortunately, when he went off to jail, he didn't have much money to pay back the people he owed. This left her in a terrible situation. She had a home with a mortgage, along with five kids to feed. She had a part-time job but was having trouble finding regular work because she didn't have a college education. As she continued on, I started realizing that she was in a real bad situation, and truly felt bad for her.
We continued walking and talking, until we got to an area where an old train trestle was. As I saw it, a bunch of memories of the good old days, came rushing back. We stood under the trestle and continued to chat, as she continued to vent. After telling me everything that was going on, I told her that I truly felt sorry for her and wished that there were some way that I could help her. She smiled and said that's why, she had wanted to talk to me. She knew that she owed me money from the jobs I had done years ago, and really wanted to pay me back, but didn't have the means. I told her that I understood the situation and told her not to worry about that, be cause it was a thing of the past. She thanked me, and told me that she appreciated it, and that she really felt bad asking me for help, but she was stuck. The town that we lived in was after her because her property wasn't maintained, and she had received several tickets because of it. Obviously she couldn't afford to hire anyone to do it, and she didn't have the funds to go out and buy lawn equipment, which is why she wanted to talk to me. She was hoping there was some way we could work things out and figure out a way for me to help her out. I chuckled a bit, and looked at her, while shaking my head.
She seemed a bit sad, and looked down at the ground as I pondered what to do or say. A part of me wanted to help her, and the other part of me didn't want to get ripped off again. Of course, it wasn't her fault that I hadn't gotten paid in the past. As we stood there, I finally spoke, and told her that I felt bad for her situation and that I would be willing to help her out with the property, but I didn't want to be taken advantage of again. She looked up at me and her eyes began to fill with tears, as she thanked me and told me that she would do whatever it took, in order for me to help her out. At that very moment, I don't know what came over me, but as she stood there crying, I started getting this weird feeling. Out of nowhere, I reached out, and placed my hand on her cheek, to wipe her tears. As I did, I slowly pulled her towards me, and before I knew it, we were locking lips.
It came as a huge surprise for me, as I had no intention of doing that, when I told her to meet me at the park. Of course, I didn't stop myself either, and neither did she. We kissed each other and did so rather passionately. She immediately slipped her tongue into my mouth, and we went at it pretty hot and heavily. As we were doing so, I put my arms around her and pulled her in tightly.
We continued to kiss, and I could feel my cock coming to life. This was the craziest situation ever, and one that I never saw happening. I mean, I always found her attractive, but since we were both married, never thought anything of it. Now, here we were going at it hot and heavily.
As we kissed, I began to run my hands up and down her back, before taking a chance and slowly lowering them to her ass. She offered no resistance, and continued to kiss me, so I began squeezing her ass. She was wearing a pair of tights and her ass felt nice and firm. I squeezed it softly before running my hands up and down her body again. She seemed to be enjoying the attention, and I once again tested the waters, by sliding my hands under her shirt and running them up and down her back. Her skin felt soft and as I was doing that, I felt her hand go down and start rubbing my crotch. I had a massive hard on at that point, and desperately wanted to fuck her. We kissed for a little while longer, as I began to kiss and suck on her neck as well.
After doing this for a short period, I broke the kiss, and spun her around, so that she was leaning up against the trestle. Without saying anything, I got up against her, and began to kiss her neck, while she pushed her ass back against my crotch. She rubbed her ass cheeks against my hard cock through her tights and my jeans, while I kissed her neck and reached up and squeezed her tits through her top. I couldn't believe that all this was happening.
As I kissed her neck, I lifted the front of her shirt, as well as her bra, revealing a very nice set of tits. I reached around squeezed them, and couldn't believe that she was letting me do that, right there, out in the open. I squeezed them for a bit before I decided to take another shot and reached down for the waistline of her tights. She once again offered no resistance, and I slowly slid them down to her knees. As I did, she parted her legs, inviting me to take her and I knew that it was on from there. I quickly undid my jeans and pulled them down as well, releasing my throbbing cock from my boxers. I quickly positioned myself behind her and rubbed the tip against her eager opening. She was wet and ready to be fucked.
Slowly, I penetrated her as she gripped the wall and let out a soft moan. I buried inch by inch of my cock into her, while reaching around and squeezing her tits. Once I was buried inside, I took a second to enjoy the warm feeling of her pussy, before beginning to thrust. I started off slow, enjoying the feel of her pussy, as she closed her eyes and began to moan. It was an amazing feeling and I couldn't believe that it was happening.
In the past, I had imagined fucking her, whenever I was working on her property, but never figured that it would happen. Now, here I was, in a spot where I used to hang out in high school to hook up with chicks, with my cock in her pussy, fucking her at a steady pace. The whole thing seemed like an erotic fantasy.
Little by little, I began to fuck her harder and harder, as she moaned louder and louder. I could tell she was enjoying it, as it was probably the first time she had been fucked in quite a while. Her pussy felt great, as it wrapped itself around my cock.
After a short time, I could feel my balls churning, and told her that I was going to cum. She told me it was okay and to keep going. With that, I gripped her hips tightly, and fucked her even harder, before finally exploding deep inside of her. I flooded her pussy with my hot seed, as I continued to thrust, until I had shot off the last of my load. Once I was done, I pulled my cock out of her, and my cum immediately began to seep out of her and down her legs. She didn't seem to mind as she began to redress herself, while I did the same.
Once we were dressed she reached over and kissed me again, while thanking me for a wonderful experience. We began to walk back towards our vehicles, and once we arrived at them, I told her that I would be by the following day and work on her property. She thanked me and said that she looked forward to it, while also telling me that she hoped I wouldn't mind being paid in ways other than money. I knew exactly what she meant, and smiled while kissing her, and telling her I would see her tomorrow. With that I was on my way back to work, while she headed home.
Sure enough, she was true to her word. I showed up the next day to do the work, and she did exactly what she said she would. Unfortunately, with all the kids in the house, we had to go into the garage, where she pulled her tits out, and gave me an amazing blowjob. I loved it and since then, I've gone back every week to do work, maintaining the house, as well as maintaining her. We've fucked in the garage, as well as meeting up at the park, and fucking in our cars, and even under the train trestle again. She couldn't get enough cock in her, and I didn't mind, because my sex life at home sucked so this was making up for it. I didn't know how she was going to handle everything else that she needed, but as far as the maintenance, I had no problem continuing, as long as she had no problem keeping her end of the deal…