Jason and Me
An older man and a young curious teen discover they have unsatisfied common needs.
I first saw Jason shortly after moving to this house. He is young, handsome, and smart, and turned out to be a huge help for me around the house as well as friend.
My wife and I purchased a lovely small home on 5 acres surrounded by woods that gave us the privacy we always wanted and yet was close to major stores and access. The grounds were immaculately kept and the swimming pool was perfect. The elderly couple we purchased it from basically ended up in a nursing home and were forced to reluctantly sell. We were grateful for the find and while my wife was alive her and I pretty much kept up with the up keep. I lost my wife two years ago to a stroke and while I’m getting over all of that loss, I did not anticipate the level of maintenance required to keep such a large property on my own but I was still not sure what I wanted to do. Anyway it was paid for and cheap to live here. So I knew that Spring and Summer would keep me busy but the rest of the year, the outside work would be minimal so for this year I’d give it a try and see how I was able to manage around the house alone.
I am 62 years old, a widower now and still adjusting. My two children are off on their own in different parts of the country but I try to get and see them a couple times a year. My work at the UPS office was downsized and as a result I was offered a substantial buy out. Between that and pensions, I could live comfortably and not have to touch savings for years. Between friends and various organizations I belong to, I try to stay busy and remain well connected. In general I’m a very happy person overall.
The only void in my live I am noticing more and more is the companionship and sex. I haven’t dated at all since my wife’s death but any potential woman out there that I’ve met throughout the various organizations I attend or volunteer work just seem unappealing. So if you can imagine my need to fulfill my want for sex and passion has been limited. Now I’m no hunk eye candy guy but still not too bad to look at. I’m 5’8″, 178 pounds. Full head of hair, and keep myself clean shaven and groomed. My body is generally smooth with no hair on my chest, and I’m generally comfortable in my own skin as they say. For my age, I guess I’m not too bad looking. However to be honest I have turned into one horny guy in the past two years and I find myself masturbating almost every night. So between outdoor gardening and some volunteer work I like to do, masturbation and fantasies are another one of my other pass times and now that I’m home alone and retired I find myself even hornier than ever before.
Perhaps out of boredom, I spend a lot of time on porn sites and generally finding ways to get myself off. I was even thinking of buying an expensive life size doll for personal pleasure but just haven’t gotten around to it yet. I don’t know why I haven’t bought one before now My latest interest has been watching gay and lesbian movies but my interests have peaked in the subject of male on male. I have never had a desire to be with a man but for some reason the idea these days has intrigued me. It brought back memories of when I was a kid and my best buddy and I would play in his Father’s shed show each other our little penises and watch each other rubbing our own. I don’t know if 10 year old kids do that sort of thing anymore but we did as kids and that’s when I discovered self pleasure and my first time kissing a penis on a dare.
Anyway back to the present. Like I said, I also spend a lot of time these days working outside and enjoying my landscaping. It was Jason that I always saw in the neighborhood. He lived in the subdivision backing up to my property and I see him walking on my street and along the edge of the tree line near my house everyday. He and his Mom Kathie had moved in to the sub behind me just before my wife died but with Kathie and I both working, we have only spoken a few times since then. I couldn’t believe how much Jason had grown since I first saw him. I have only seen him twice since we first met and wow I thought, he is growing up to be quite the hottie!
At first, her Son Jason would just walk by and wave but the past few occasions he had stopped and introduced himself again and we chatted for a few moments before continuing on his walk. He’s just a kid, and 12 years old now. Really a sweet and polite kid and so cute. I found myself staring at him as he walked by wearing his little shorts and tank top and sneakers. When we spoke I couldn’t help but to notice his nipples protruding from his tight fitting tank top. Surprisingly I found him to be very sexy and caused my cock to tingle. I was a little confused at my reaction towards this young boy but I guess I should have expected it since I have been enjoying watching and reading gay sex material. The feeling of getting turned on at the site of this young boy was a new sensation.
He would always stop now and say hello if he saw me outside in the garden and I would always make sure to stop what I was doing and take the time to chat with him. He was attractive and sexy in his own sort of way and he was at that age between being a kid and forming into a sexy young man. Surprisingly enough, when we spoke he would take my breath away and the tingling in my cock would remind me how horny I really was. I have thought what it might be like to have sex with another man now that these new feelings and sensation had been in my mind and if the opportunity came up I wondered if I could muster enough nerve to try it. I tried to think of what other men I might know that live alone and might be going through the same feelings and desires I was but none came to mind and I’d probably chicken out anyway. But I had certainly never considered having sex with a young boy barely in his teens but when I met Jason my thoughts and curiosities were stirred at the possibilities.
With school out for the summer now Jason was basically home alone while his Mom went to work. Being in a secluded area, its not like you could walk to the mall or anything like that so without a driver’s license it wasn’t easy to get anywhere. Basically Jason visited and chatted me up often either because he was bored or he actually liked being around me. I concluded that its probably because he’s bored but it didn’t matter anyway, I enjoyed his company and I appreciated someone to talk to. After a few visits and idol chats I invited Jason into the back yard and offered him a cold coke while we sat around the pool. He told me all about himself, his likes, and about school, and we seemed to chat it up like that over the course of a few days.
On one occasion, he told me how bored he was. Jason didn’t even have a cell phone to talk to his school friends with and I felt a little sorry for him Has I imagined what a long Summer break it will be for him. He wasn’t old enough to drive, too young to get a job, and no way to get there even if he could work and that sucked he said! I laughed about how he phrased it and I told him how sorry I was that he was stuck at home most of the Summer. We talked more and I was completely enamored by his youth and optimism. The more we chatted the more I appreciated him visiting me, almost daily for the past couple of weeks. To the point that if he didn’t stop by I would miss him.
“So I was thinking Jason,” I casually asked him, “Would you like to work for me as a summer job? There are plenty of things to keep you busy around here as you can see, and I’m really not able to keep up with it all myself. Maybe you could use the extra money?”
“You can work a few hours a day helping in the gardens, cleaning the pool, helping me with some light housework, and then just hangout with me if you like, or use the pool or whatever want.”
Jason’s face lit up with enthusiasm and told me he’d like that a lot. I commented how much I appreciated his company and he would be a big help for me. I told him jokingly that on one condition. Jason looked at me waiting for me to continue. I delayed my response for a few moments, keeping him in anticipation. Jason saying “What, what is it?” He taunted.
“Well the condition is that you let me make you lunch after you’re done your morning choirs. I usually like to take a few minutes to eat lunch and it would be fun to have you share that with me.”
Jason was delighted and after, we worked out her pay details, we agreed on our employment conditions. The fringe benefits of the job would also include unlimited use of the pool and Sun deck, a free lunch, and a place to hang out if he wanted company. We joked about it for a few minutes and I could tell Jason was thrilled at the idea and so was I. Of course he was to get an okay from his Mom with the whole job deal so that evening I met with Kathie and let her know what Jason and I had discussed. Of course her she was delighted that Jason would be busy and not so much alone at home this summer. We had some coffee together and I learned that Kathie was divorced and had raised Jason herself for the past 5 years. She is a nurse at the local hospital and works crazy shifts but has a good income and she and Jason were doing ok. I was happy to meet Kathie who is younger than me, maybe 40 or so and I’d say on first impressions we liked each other. Actually I thought she was pretty hot and made a mental note to include her in my masturbation fantasies!
So the next day Jason and I spent most of the morning reviewing what I needed done and he was happy to have a chance to earn some money. I showed him how to clean the pool, check the filter, and check the chemicals, and I showed him how to use the riding mower, leaf blower and edge trimmer. He was amazing and picked up on everything very quickly. Before Jason got started outside each day, he would spoil me and come in and clean up any dirty dishes if there were any, he would make my bed and tidy up, dust every other day, and even wanted to do my laundry. I believe he learned that from his Mother and it was a good feminine trait to have.
He was quite the domestic help around house and would make someone a perfect partner one day. Plus I think he was trying to please me.
“Jason you are an amazing help around here! I’m so pleased with everything you do for me.” I told him. “You are spoiling me rotten and not leaving anything for me to do.”
“Oh sorry Mr. Waters, I just want to do a good job for you.”
“Well Jason, first of all please call me John, and I want you to know how much I appreciate your help and your company. You are such a sweet kid and good friend to me and you are doing a great job! I hope you help your mom out around the house as much as you help me.”
He liked hearing that and I soon gathered that Jason appreciated the attention. He was a pleaser. His Mother Katie had done a good job raising him so far and I made a mental note to compliment her on that next time I see her. I noticed every time I complimented Jason or praised him for something, he would light up and soak it in like a sponge. I hated to take advantage of him that way but soon learned I could get him to do anything with a few compliments and words of praise. Maybe because he doesn’t hear it at home, or he is a little shy and feels inadequate around his friends but either way I liked complimenting him and seeing his reactions. It made me feel good knowing he was happy and oh my God he was so cute and sexy and of course I would tell him that to.
Over the next few days we sort of got into a routine. Jason would arrive in the morning around ten and get started on what needed to be done. He was surprisingly organized and I couldn’t help to stare at him throughout the whole time as he worked. I enjoyed watching him bend over or seeing the outlines of his tight little ass when he wore his tight cycling shorts. Sometimes I would notice a small bulge and I loved it when he wore those shorts. I also enjoyed fantasizing what it might be like to kiss him and suck on his small dick and wondered if he had any hair on it. How would he would react to such a thing? What if I complemented him enough, maybe tease and groom him enough that he might want to show me. I appreciated him being around, I wasn’t so lonely these days and I got my cheap perverted thrills checking him out without him knowing. So as the routine went, we would have lunch and sometimes finish up what he started but for the most part we got into the routine of just laying around the pool in the afternoons soaking up the Sun. He really didn’t have anywhere else to go and neither did I so fortunately for me I enjoyed the company.
On this particular day I was feeling very horny and since the Sun was hot and the day was humid, I mentioned to Jason that we should just hang around the pool this afternoon and do nothing.
“You are doing an amazing job and I really appreciate all of the choirs you’re getting done for me. I’m so happy you agreed to help me out!” I could see Jason blushing a little but knew that he was soaking up the compliments and appreciation. I told how much of a good friend he had become for me and that I wasn’t as lonely these days as I would have been had he not visited me so often. All of what I said was true of course.
“Oh I don’t mind John, I like hanging out with you. It’s way better than sitting around all day waiting for my Mom to come home. I used to wish school would get started sooner but now I’m really enjoying my summer break.”
Jason didn’t have his swim suit with him today since we were not planning to go in the pool and he wanted to go home a get it. I explained that it would be Ok if he just sat around in his underwear, save him a trip, and that if was more comfortable that I would just do the same. Jason agreed and I proceeded to strip down to my boxers. Jason stripped down as well. He was also wearing boxer shorts. We sat around on the pool deck for awhile longer and Jason and I went in and out of the pool a few times. I was enjoying having someone around to keep me company and I think Jason also liked hanging out with me, despite our age differences.
“Jason!” I asked him, would you mind rubbing some of this 15 screen on me? I don’t want to burn.”
“Sure Mr. Waters, I mean John.” And we laughed about him always correcting himself like that.
“Looks like you should be using some Sun screen yourself buddy,” I told him with concern. He was getting red and he knew it. “I’ll do you after you do me,” I told him. I realized after I said that how it may have sounded but yes I would like to “do him” if wanted to.
“Ya sure John, that would be good.” He assured me.
I lay on my stomach and enjoyed the sensation of the warm cream on my hot skin and I especially enjoyed him touching me all over. I spread my legs just slightly when his hands were near my inner thighs. It was instinctive that I spread my legs but he didn’t go there with the lotion. I was a little disappointed but none the less feeling relaxed and mellow and felt like he could have messaged me all day. I let out a low sigh and realized I had a raging hard on.
“You don’t have any tan lines John.” He noticed, and I told him that I usually tan naked. The Sun feels amazing when your naked.
“I don’t want to gross you out or anything but it’s very private back here and I’m always here by myself so I usually don’t wear anything at all when I sun tan. As you can see no tan lines anywhere!” I said jokingly as I continued to just lay there on my stomach, resting my head on my forearms. I went on to say it feels so amazing and so natural. I hope that doesn’t gross you out or anything but like I say it just feels so amazing.” Jason didn’t say anything. He just dutifully squirted the lotion on my back and nervously worked it in.
“Oh by the way I wouldn’t mention to anyone I sun tan naked, our neighbors might not appreciate it and we shouldn’t tell anyone, not even your Mother or friends at school about it.”
“No way John I would never say anything, not even to my Mom!” I could sense Jason felt comfortable with me and knew he could trust me. I would make a point to compliment him more and show him my appreciation. I know he would like that.
“Oh wow Jason! You are such a great guy and a good friend. It feels so good when you rub that lotion on me. I bet you give good messages as well!” I commented hoping for a reaction.
“I don’t know anything about messages I’ve never given one or had one but I’ll try to give you one if you like.”
“Oh yes,” I moaned. “Oh yes, you are doing great job so far,” I reassured him. “Can you keep doing it? And after I’ll give you one if you like.”
Jason was actually pretty good at it. He was gentle and deliberate in his movements and asked me if he was doing it ok. I answered yes, and told him he could keep going as long as he wanted or stop any time he wanted to. Jason applied more lotion to his hands and rubbed all along my shoulders and back. He rubbed the back of my arms and then the back of my legs. He must have been messaging me for a few minutes because I was dreamy and dozing off in and out and I woke myself up with a moan.
“Are you ok John, did I hurt you?”
“Ha ha oh no buddy, you are doing this so perfect. I actually dozed off I’m so relaxed. You have magic hands my friend and I love the feel of the hot lotion on my skim.” I told him.
I praised him again that he really knew how to give a great message for a first time and that it feels sooooo good being touched. Guess I’ve lived alone too long!
He laughed and I offered to rub lotion on him and give him a message. His first message as he stated. I got up off the lounge and quickly realized that my hard on was tenting my boxer shorts and wasn’t sure how to handle it so I joked about it.
“Oh my God!” I laughed looking at him and looking down at my own cock, “you must have a crazy effect on the girls at school and from the looks of me you have a magic touch that got me hard. I’m so sorry you had to see that! I’m a little embarrassed.” Jason was looking and he didn’t seem to be offended. Actually he looked very curious and almost an hypnotic look.
“Ah don’t worry, I’ve seen dicks before at school showers after gym class but I’ve never seen one that big though!” As he continued to look. Jason’s eyes were glued to my raging hard on I couldn’t remember the last time it felt that hard. This kid has had an effect on me, no question. I told him that I don’t usually get this hard anymore at my age so thank you very much for helping in that department and I chuckled as I tried to read the look on his face. “So ok then! I don’t feel too bad, I thought it may have upset you Jason.” I was still laughing at what just happened and for some reason the image of him checking out the other boys in the locker room came to mind.
“So you have checked out other boys dicks before? That’s pretty normal you know.” Jason looked at me and looked surprised and somewhat relived that he wasn’t the only one doing that.
“Really guys do that?” He asked in surprise.
“Oh ya it’s pretty normal, I guess it’s a guy thing. Have you ever experimented with other boys,” I asked him. “You know compare each other’s dicks and stuff?” Jason looked embarrassed and I quickly added that when I was his age, it was pretty normal sometimes to sit around with your buddies and show off your stuff. Sometimes we would watch each other rub our own dicks and see who could get harder, bigger, and faster. I don’t know if kids do that anymore. Jason was so surprised that I would even know about stuff like that since he heard about it from his friends and that some bragged that they were doing it.
“Oh ya sure, I heard some of the guys at school talking about when they have sleep overs but I never did.”
“Ya that’s cool Jason, it was pretty normal at 11 and 12 to be curious about stuff like that.” I told Jason that his age is one of the most curious ages when it comes to sexuality and when I was around 12 I didn’t have a Dad or a big brother to tell me anything. I wish I had someone to talk to about that stuff. I had to learn through my friends or on my own.
“I don’t know where my Dad is, and I’m an only child and no way I’m asking my Mom!” He laughed.
“Yes I can see that as a problem. Well if you ever have any questions or anything, we are pretty good buddies I think. Just ask me, no problem, it will be our secret. Oh just one more thing, I was just wondering, by the time I was 11 I was already jerking off. I know you might be embarrassed to tell me but I was just curious if you have already?”
I hope I didn’t cross the line here with this questioning and hoped that Jason wouldn’t just up and leave in embarrassment. When I asked the question it was like I had busted him on his secret as if he was the only boy that ever played with himself and he was found out. I was a little disappointed in myself to have asked him such a direct and personal question, but it’s done and I quickly changed the subject.
“Jason, you are defiantly getting sun burned.” I said very as a matter of fact. “You can’t be in the Sun this long when you’re that white. Come over here and let me put this 15 screen on and you should be good for a few more minutes in the Sun before finding shade or jumping in the pool. Besides, I can give you your first message ever!”
Jason lay on his tummy with his head resting on his folded hands. He was a skinny little thing, looked very cute in his baggy boxer shorts and left practically nothing to the imagination. Looking at him there I couldn’t help but to imagine him naked. Anticipating on rubbing and caressing his cute little tight ass but cheeks and waiting for his reaction. I was not sure where these new perverted thoughts of mine were coming from but they were exciting thoughts. Of course I knew in reality if I touched him that way it would probably freak him out and he’d be gone so I had to gently seduce him!
“Ok then Jason just lay there and relax, I’m going to rub this sun screen on you because you are defiantly starting to burn, and I’m going to give you your very first amazing message and you will love it!”
He was delighted and told me he had never had a message.
“Ok then buddy, I’m going to show you how it’s done!”
I slowly rubbed the lotion on his shoulders and back, being deliberate but gentle and allowing the tips of my fingers to inconspicuously touch the sides of his chest. I applied more creamy lotion to the small of his back and to the back of his thighs and gently rubbed it all in. Then I started messaging his inner thighs and legs. Sliding my slippery palms all up and down the back of his legs, squeezing several muscle groups as I went, and allowing the flat palms of hands to message and squeeze his butt cheeks underneath his boxer shorts. His cute butt cheeks were tight and pleasurable to the touch. My cock was fully erect now and Jason was sighing and moaning quietly under my touch and every so often I would ask him if he was Ok. After about 15 minutes I told him that if he wants the real deal, we would have to do his front muscle groups and so I asked him to turn around.
Jason laid on his back and the first thing I noticed was his hard on. I smiled and told him he had the same effects on me so just relax and enjoy. I proceeded to lather him up with suntan lotion and start messaging his chest and each arm. I lingered a little as I gently squeezed his nipples and then started messaging his legs starting with each foot and moving slowly up his legs and messaging his inner thighs. Should I stop myself I wondered or should I reach in and discreetly touch his balls? I should have stopped myself from getting too caught up in my thoughts but I wanted to slip my hands up underneath his boxers and touch him there. I asked him if he liked the message so far and he confirmed yes. I slowly moved my hands up so the tips of my fingers would barely touch his balls. By now Jason’s little 4″ cock was rock hard and I was sure he would have like to touch it.
I commented how hard and nice his cock looked and asked him if I could touch it. I didn’t hear any response so I took it as an Ok to go further. I rubbed him down pretty good and thoroughly covering every exposed part of his skin without freaking him out. My slippery hands rubbed in and around his hard cock but I didn’t actually touch it. At least not yet. I told Jason that since it was just us guys here, I wanted to tell him that I thought he had a nice cock. I already had an erection and was dying to touch it and I was sure Jason felt the same way.
“I was wondering Jason, I think you are pretty hot for a young kid and was wondering if you would let me see you naked?” I had already stopped messaging him and he looked at me as if to say something. I quickly offered to show him mine first if he wanted to since he had never seen a grown mans cock before. Jason put his hand on his and was holding it, I guess waiting for me to get naked. He looked around and I reassured him my yard is completely private so no worries its just us guys here. I lowered my boxer shorts and held my cock up proudly asking if he had ever seen anything like that before? Jason just starred and said no.
“Do you want to touch it?” I asked him. Then I took both his hands and placed them on my hard cock. “Go ahead and touch it if you like. I don’t mind. You can play with it all you want. I know you want to. As you can see you are so sexy Jason, you make me hard.” At this point I wanted him to suck on it but I was taking everything slow and easy and letting him take the lead. After a few moments I mentioned how hard he looked and can I see his?
Jason slipped out of boxer shorts and there it was. Practically hairless, cut, and very hard. “Can I touch it?” I asked him. He didn’t have to answer, I already knew the answer. I held his cock and started to gently jerk him off. I knew he would cum soon so I put my mouth to his cock and gently swallowed it in. Jason was in heaven. He was squirming and moaning. I gently sucked on him and within a few moments he an amazing orgasm. The best he had ever had!
I gave Jason a few minutes to recovery and get his head straight. I told reassured how sexy he is and if I was a girl I would want to kiss him. Jason leaned over and placed his arms around my neck and pulled me in for a kiss on the lips. I enjoyed the feeling and instinctively I kissed him back.
From that day forward Jason and I played with each other the entire time during his Summer break and there will be other adventures to write about later.