I responded to the request, accepting it, and a few days later, she sent me a message. I read her message, which was basically her asking me how I was doing. I responded, telling her I was great, and we went back and forth for a few minutes, messaging each other. As it turned out, her father-in-law at the time was one of my lawn customers. I had no idea, and thought to myself, what a small world. For the next few days, we exchanged messages, and I also checked out her profile, and noticed that she did a lot of charity work, as well as being an art teacher at the local middle school. She often left me a lot of responses, and comments, because I always posted pictures of my little guy, who suffered from seizures, and dealt with autism, and it was something that was very near and dear to her heart. Her own mother suffered from seizures, so she knew what I was going through. We often messaged each other about it, and I could see that she really cared for my little guy.
As time went on, we continued to stay in touch, and I became one of her best clients when it came to her charities, especially at Christmas time. She always put together a list so anyone who was interested could buy gifts for children who didn't have much. Growing up wasn't always easy for me and my family, so I knew what these kids were going through, and since I was doing okay in life, I would often purchase many gifts from her list. I would then go back on the final day, and if there were any gifts left over that weren't purchased, I would buy the remaining items. She often thanked me, over and over again, while also telling me that it wasn't necessary to purchase so much, and that she really appreciated what I was doing.
We hit it off pretty good, messaging each other often, and I was happy to be able to catch up with her after all these years. Then, one day, everything changed.
It was at the beginning of last year, when I noticed she went silent, right after the holidays. I figured that she was away on vacation, or something like that. I asked one of my nephews, who was in her class, and he told me that she was there, but had recently changed her name. Alarm bells immediately went off in my head, and I knew something was up. I tried to message her, but there was no response for several days. I began to get worried, and hoped all was well with her. At the same time, I didn't want to be too intrusive in her personal life, so I waited to see if I would get any response.
About a week later, there was still no response, so I asked my nephew to just say hi to her in class and send her my regards. He did, and that night, I finally got a response from her. I opened my messages, and there was a very long note for me to read. I sat and read it and saw that she had just gone through a very nasty divorce. I felt sad for her, and knew what she was going through, because my own sister had recently gone through a nasty divorce as well. I reached out to her and let her know that I was there if she ever wanted to talk or anything else, and she thanked me. I mentioned that my sister had gone through the same thing, so I knew what she was feeling and what she was going through. We went back and forth, and this opened up our conversations once again. We continued to message each other on a daily basis, and slowly I could see that she was starting to get back to herself. Then, this past summer, things really took a turn.
It was a warm Saturday night, and I had just finished eating dinner when I decided to go down to my man cave and have a drink or two. I grabbed a brand-new bottle of Scotch that I had just purchased and poured myself a glass. As always, I grabbed my phone and took a picture of both the bottle and the glass and posted it on my social media pages. I instantly got a few comments, and so that one was from Jill. I read it, and she had commented, asking me if I delivered, because she could certainly use one or two of those. I replied to her message, playfully telling her it was no problem and that I just needed an address. I followed that message with a lol, and a smiley face emoji. I wasn't expecting much, and figured we were just being playful, but was pleasantly surprised when, within a few seconds, I received a private message from her. I opened the message, and all that was in it was an address, which was only a few blocks away. I looked it over real quick, and without really thinking about it, I grabbed the bottle, along with my wallet and keys, and was soon in my truck, on my way to her house. I didn't really put much thought into it, and had no idea what I should expect, but figured we would just roll with the flow. After all, it would be nice to get together, and enjoy a few drinks, instead of constantly messaging each other. I hadn't seen her in well over 20 years and was extremely nervous as I pulled up in front of the house.
After parking my truck, I made my way to the door and rang the bell. I could feel butterflies in my stomach as I stood and waited. The door flew open a few seconds later, and there stood Jill, with a big smile on her face, looking just as good today as she did back in high school. She was wearing a summer dress, which showed a hint of cleavage, and came to rest just above her knees, and she looked great. She quickly greeted me with a hug and kiss on the cheek, and after we exchanged pleasantries, she invited me inside. We headed up to her apartment, where she guided me to the living room, while she ran to the kitchen to grab two glasses, and two beers. She returned a few seconds later, and I quickly poured us each a glass of scotch, while she also cracked the beer open. We sat back on the couches, sitting opposite each other, and began to chat.
We spent the next hour or so chatting and catching up on the past 20 years, and I think we were both surprised to be sitting in her living room enjoying some drinks. It certainly was something I never expected after graduating high school.
As we chatted, we continued to drink, and at that point each had consumed a couple of beers, as well as a couple glasses of scotch. We were both in a great mood at that point and really started to open up to each other.
At one point, she looked at me and apologized to me for the way she behaved when we were in school. She told me that I was always a sweetheart to her, and she basically just used me to carry her books home every day and have me help her with her grades, since I was always doing essays and reports for her. I told her it wasn't a big deal and that it was just the way I was. I told her that even today, I often did stuff for free for some of my clients, because it just seemed like the right thing to do.
After a bit, she got up to go use the bathroom, while I poured us another round. She returned a few minutes later, and as she walked back into the living room, I gave her a once over and smiled, while shaking my head. She stopped and looked at me, with a puzzled look on her face, and asked me what was the matter. I responded and told her that she looked just as great today, as she did back in high school. She thanked me, telling me that I was still that same sweetheart, and I smiled at her, while telling her I couldn't believe that I was sitting on her couch, having a drink with her, some 20 years after having such a huge crush on her.
As I said it, she put down her glass and didn't say anything. Instead, she came over to the couch where I was sitting and took my drink from me. She placed it down on the table, and without saying anything, she climbed onto me, straddling me in the process and quickly grabbed my face. Without warning, she placed her lips on mine and kissed me. I was both shocked and surprised, but at the same time, found myself kissing her back.
We locked lips for a few seconds, before she broke the kiss and just stared at me. At that point, I grabbed her, and pulled her in for another kiss, and this time, we went at it rather passionately. Our tongues intertwined in each other's mouths as I ran my hands up and down her back. As I was doing that, she quickly reached up and pulled the straps of her dress down her arms and followed that up by pulling the top of her dress down, revealing her lovely tits to my eager hands. I quickly went to work squeezing them, before lowering my lips to each of her nipples, where I licked and sucked on each of them while rubbing her tits all over my face.
As I was doing that, she reached down underneath her and began to rub my throbbing cock through my shorts. She did this for a bit, before reaching for the waistline of my shorts and beginning to tug on them. I quickly grabbed them and began to pull them off, while she lifted herself a bit to give me access. Once I had them off, my cock sprang free and she quickly lifted her dress up, revealing she wasn't wearing any panties.
She lowered herself onto my cock, and her pussy was soaking wet. I was quickly buried deep inside of her and the two of us sat like that for a few seconds before she began to slowly raise and lower herself on my cock.
She took her time at first, and her wet pussy felt amazing as it gripped my cock tightly. Slowly, she began to pick up her pace as she moaned louder and louder. By the way she was moaning, I could tell she hadn't been fucked in a while.
As she rode me, I gripped her by the hips and guided her, while her tits bounced around in my face. It was such an erotic feeling, to be sitting on her couch, while she rode my dick after all these years. It had been a fantasy in high school, but now, it has quickly become a reality, and I was enjoying every second of it.
As she rode me, I felt her grip my shoulders tightly and she closed her eyes. She then let out a very loud moan, and her entire body began to shudder. I could feel her cumming all over my cock as she slammed down on it.
She continued to ride me, while gripping me tightly, until she came down off her high. She then began fucking me harder and harder and within a few seconds, I felt my balls beginning to churn. I warned her that I was getting close, and she moaned into my ear that she wanted me to cum in her. I gripped her hips as tight as I could, and within a second or two, I exploded deep into her pussy, flooding it with my hot seed. She continued to bounce on me, using her pussy to milk me of every drop.
Once I was done, she collapsed on top of me and the two of us sat and tried to catch our breaths.
Eventually, she climbed off of me and cuddled up by my side on the couch as we enjoyed a couple more sips of our scotch.
We sat for a few minutes, before she looked up at me and we kissed each other once again.
She then got up and held her hand out. I grabbed it and she led me through her apartment, to her bedroom and I knew that I had a very fun night ahead of me...
|
Note from the webmaster: authors always appreciate feedback about their stories, so by all means write the author a note if you liked the story! The author of this story: oppy-n-rose |