Date: Sat, 1 Jul 2023 09:59:22 -0400 (EDT) From: ShortStories@PlayTime69.e4ward.com Subject: Helpful Boy Gets Paid This story is 100% fiction and is for mature readers only. If you are under 18 please leave now. Please note that all my stories are written for enjoyment only and not intended to give anyone ideas on what to do, what to try, or who to do things with. The actions taken in my stories should stay in your mind only and not expanded to real life situations. This story is a fantasy involves an older male and a young preteen boy. You can see a list of all my stories on the authors page under the author, Playtime69. All comments are appreciated and can be emailed to ShortStories@PlayTime69.e4ward.com. Please identify what story you are talking about when you send me a message. Even though I do not respond to all emails I do read them all and have used some of your suggested ideas in my stories. I also will write new stories with your suggested ideas. Just send me your ideas to address above with as little or as much information as you want to tell me including names, ages, sexes, positions, relationships, and what section on Nifty you want the story to go, etc. I will see what I can do with it. If you want to name the story that is fine too. Just make sure the information is yours and not from someone else's story. Thanks for reading. Please, find it in your heart to donate to nifty at http://donate.nifty.org/donate.html without them we would not have a safe place to deposit and read such great stories. This story idea and basic information came from one of my readers. I took their information and worked it into the story you see here. I hope you enjoy this story about how a young boy get paid for helping an older gentleman in an unusual way. Helpful Boy Gets Paid by: Playtime69 "Wow! What a storm." I commented to my neighbor and his son. "Yeah. I have never seen anything like it in my life." The neighbor responded. "This will take me a year to clean up. I am just so tired of these storms I am tempted to move where there is not so much of an issue with the weather." I added. "Well when you find that place let me know and I will go with you." He chuckled. My neighbor and his 11 year old son began to clean up their yard while I did the same with mine. The problem was I had been injured at work many years ago and was disabled. The settlement that I thought was fair then does not even come close to giving me an easy life. I had money for food and the house was paid for but left little to none for emergencies or to hire help in cases like this. All I could do was plug along the best I could. I could not work long before I had to rest and I could not move heavy objects without help. It took my neighbor a few weeks to get their yard back into shape where it looked like I was just getting started. Summer had arrived and Daniel, the neighbor's 11 year old son, was out of school. He saw me trying to move a broken tree limb and asked if I needed some help. I told him I did but did not have any money to pay someone to help so I just had to do the best I could. The next thing I knew Daniel was gone. Not knowing where he had gone I went back to work. A few minutes later Daniel was right in front of me in my yard. "Mom said I could help you clean up your yard. That is if you did not mind." Daniel explained using a very serious tone. I was almost in tears as I told him how much I appreciated the help. I told him I was really sorry I could not pay him but maybe someday I could find some way to help him out. He just giggled and said that was not necessary. He told me that he did not have anything else to do and that he did not have any friends that lived close by so helping me would give him something to do this summer. The days had been getting warmer but this day was particularly hot. We had only been working together for less than an hour when Daniel asked me if I would mind if he removed his shirt. I told him I did not care and he could remove whatever he wanted to be comfortable. I had to take more breaks than normal and quite often I went inside to get Daniel and myself something to drink. We would sit and talk as we drink water and rested. We began talking about his school, his friends, and what he liked to do. After a few breaks I knew most there was to know about Daniel and his friends. He then began to ask me questions. He wanted to know my age, how long I had lived next to him, and about my disability. I told him that when I was younger I had an accident at work which left me disabled. I explained how I could not work long before I had to rest and how my disability check was not going as far as I had hoped it would. I finally got into some of the more personal questions by telling him I was 67 years old and had lived in the same house for 35 years. I told him my wife had passed away 15 years ago and it was like a part of me also died. I explained that it really did not matter much that I did not have a girlfriend because the accident had left me impotent. "Impotent? What's that?" Daniel asked. Chuckling I answered, "Means that I can't get it up." I then looked down between my legs so he knew what I was talking about. He kind of blushed before telling me he was sorry. I told him it was alright and that I was still interested but could not do anything about it so I just ignored the idea. Soon we were back to work but now after the last conversation I began to notice Daniel's muscular tanned body. All he had on were some pretty small shorts and shoes which made his arm and leg muscles stand out. His light brown shoulder length hair gave a great introduction to his childlike chest and back. Other than the hair on his head, he appeared to be hairless which was a sure delight to look at. His butt was firm and small and was sitting atop his narrow powerful tanned legs. It was hard to get a look at his package because that would mean I would be in front of him and the last thing I needed was him running home telling his mother I was looking at his peepee, so I figured I would just take a look when I could. It was not like I could do anything with it anyway. Daniel eventually went home for lunch but to my surprise came back an hour or so later. We worked until he had to go in to get cleaned up for dinner. Not long after he left, Daniel's father walked over and told me that if Daniel ever got too personal or too much trouble to just send him home. He told me that his son would try to get all the information from someone that he could. It was just that he was really curious about people. He finished up by saying it would not surprise him if he became a psychiatrist when he got older. I told him he was fine and a great help and that I appreciated it more than he would ever know. He thanked me for putting up with Daniel and with that I went inside and he too headed home. Not knowing what to expect I went to work in the yard the following morning. To my pleasant surprise, Daniel was over soon after I had began to work. Soon as it began to get warm his shirt came off without asking me this time. I wondered what he would do if I took mine off but figured I would ask his permission. "Would you mind if I remove my shirt today?" I cautiously asked. "I do not care. This is your yard so you can take off whatever you wish." He told me. Even though I could not get an erection I still liked to be seen and the thought of being naked in front of an 11 year old boy was tempting. I decided to play it safe and just chuckled as I simply removed my shirt. We worked well together and he enjoyed the breaks and talking as much or more than I did. Over the course of the next few weeks we got to be pretty good friends. I finally got to see his crotch but he did not appear to be hard. There was not much I could tell from what I saw except the desire to see more. Like it or not I was getting interested in his body but not for my own personal gain. I was getting interested because I felt I could have a second childhood through Daniel. I figured if I could help him grow up and have some fun then it would be like it was myself doing it too. The more we worked together the more we were becoming one. On more than one occasion he knew what I was thinking and I knew what he was thinking. It was a good thing he did not know much about sex or things might have really got out of control right there in the yard. Eventually we would both start the day wearing just shorts. I even went so far as to not wear underwear from time to time. I know my dick fell out some but was not sure if he saw or cared. I knew it was dangerous but I was hoping he would ask more questions about sex but that joy never happened. We were within a few days of finishing the yard work when I decided to push Daniel into thinking about sex or at least wanting to know more about it. I invited him over for dinner just before our last yard work day. He told me what he liked to eat and after his mother gave permission we set up the day and time. Luckily I did not have to wait long before that night came. "Hi Daniel. Come on in and make yourself comfortable." I told him when I saw him at my door. "Thank you." He politely said. "Dinner is almost ready. You can come on into the kitchen and we can talk while I finish things up." I suggested. "Ok." He simply replied. He followed me in and I pulled out a stool for him to sit on while I finished up our meal. We talked about general things including how much I appreciated his help and his companionship. He told me that he too enjoyed it and was sad it was over. I let him know that he could come over any time to talk or help with things as long as his parents said it was alright. That seemed to lift his spirits a bit. With the food ready I fixed our plates and drinks and carried it all into the dining room where we were going to eat. "I really wish I could give you more for helping me with the yard work." I told Daniel as we began to eat. "I like to help others and anyway it gave me something to do." He said. We talked more about school, his friends, his classes, and teachers. I tried to move the conversation into a sexual one but I just could not get that subject started. I was running out of time and was getting desperate so I finally made a bold move. "Daniel. I know it is hard to talk to your parents about some things and it sounds like you do not have many friends you can talk to either. So if there is ever anything you want to talk about or a subject you want to know more about all you need to do is ask. What we talk about will stay just between us. Ok?" I told him hoping it would spark a new line of conversation. "Ok. Thanks." He bashfully said. It seemed like I had made a connection but he either did not trust me or he was just too shy to talk about it. There was not much more I could do about it at that time though. We continued to talk and I served our desert. I could tell he was in deep thought about something. I was just not sure what. We were just about finished with desert when Daniel blurted out, "What is a normal size?" "Normal size?" I questioned. "Yeah. You know. How big is normal." He said again but this time he pointed to his lap. "Ohhhh. Well, the normal size of an erect male penis is a little over 5". If it is not hard then the average size is about 3.5." I answered once I figured out what he wanted to know. I guess this opened up a new opinion of how he thought of our friendship. I was open and to the point with the answer. I did not cross-examine him on why he wanted to know nor did I make fun of his question. I was a little curious of why he was asking. "Thanks." He quietly said. I was hoping he was going to continue asking more questions but he simply went back to his desert. We finished and I carried our plates into the kitchen to be washed later. "Would you like to sit in the living room and talk some more?" I asked hoping that he just needed more time to get the courage to ask more about sex. "Sure." He answered. We went into the living room and sat down. When he did not say anything I knew he wanted to talk more on the subject but was still just too afraid to ask. I again began to prod him along. "Can I ask why you wanted to know? You do not have to answer if you do not want to. I just want you to know you can ask anything you want." I told my 11 year old neighbor boy. "Well. There is this guy at school. He is about my age. He might be 12. I am not sure. Anyway, he said his was 8" when it got hard. And...well... mine is only about 4" maybe 4.5" when I am really super hard. I guess I was just thinking that there was something wrong with me." He bashfully said. I began to laugh which made Daniel a little upset. I quickly told him I was laughing at what his friend said and had nothing to do about his size. "Did your friend ever show you?" I asked. "No. We told him to show us but he said he was not going to whip out his massive cock in front of a bunch of guys just to prove something." Daniel answered. "Well...There you go. He is just bluffing. Have you ever seen him soft?" I then proceeded to go deeper into the topic. Daniel giggled and said, "Yeah. It was in P.E. We had to shower and I saw it then. His was smaller than mine. When I said something he told me to keep my eyes to myself and that it was so small because of the cold water and because another guy was looking at it." "Well it is true that being cold will make it shrink and sometimes even quite a bit. Some boys are shy and if they do not like to be looked at then that too will make it smaller." I tried explaining why his friend said what he said. But, I knew there was more that needed to be said so I asked, "So, how big is yours when it is soft?" Blushing a bit he said, "1.5" maybe 2"." "Ok. Well first. I am going to say yours is normal and maybe even a little bigger than normal. I would guess that your friend's is either the same size as yours or a little smaller. Now if he has started puberty then his should be bigger than yours. You have not started puberty yet have you?" I rattled on before finally asking the next question. "I do not think so. I still do not have hair down there, my voice is not changing, and I still do not have any hair under my arms." He answered. "Does your friend have hair around his?" I asked. "Yes. some." He answered. "Sounds like he has started and his dick should be bigger than yours but sounds like yours is bigger so you have nothing to worry about. You are normal. Sounds like your friend was just trying to make himself look good." I explained. Daniel looked a lot happier because he had found someone he could talk to about his sex questions. We continued to talk some about guys and girls but nothing too exciting. It was getting late so I told him he had better go on home but if he ever had questions he now had someone that he could talk to. He thanked me and on the way out he gave me a hug in appreciation. I hugged him back and watched to make sure he got home safely. I already knew he was not going to be able to help the next day so I took it easy and just relaxed. Later that day I went to get the mail out of the mailbox just as Daniel's father drove into the driveway from work. I waved to him as he exited his car. He waved back but also called out, "Donald. Hold on. I need to speak to you." "Ok." I responded as I felt my heart race. Could Daniel have said something about our talk? Had his father found out about my interest in his son and wanting him to get paid for his serviced but not with money? Were just a few of the thoughts rumbling around in my brain. "I just wanted to thank you again for inviting Daniel over for dinner last night. He really enjoyed himself." His dad told me. "I was glad to do it." I replied being greatly relieved. He then continued by saying, "I am sure he told you he does not have many friends and even fewer he can talk to. But what he probably did not tell you was that he feels more comfortable when he is around adults than he is around kids his own age. He joins in with the adult conversation anytime I have my friends over. Problem is most of them would rather him not be around. You are different. You seem to like being around him. So, again, I just want to say thanks." "That really means a lot to me. And, yes, I do enjoy talking to him and being around him. Funny but I something think of myself as just a boy that never grew up. So being around Daniel is like being around someone my own age." I explained. "Daniel was really excited about last night but then he is also sad that your yard is now almost finished." Daniel's father then told me. "One more day will get it. Then I guess you can have him back for your yard work. " I chuckled. "Problem is that I only have the weekends to do the work. That leaves all week for him to be basically alone." He then told me. "Well I do have a project he could help me with. That is if you do not mind." I said. "What's that?" He asked. "The paint I use inside the house is on sale and I was going to repaint the inside of the house. I could really use some help moving stuff around and painting. It is going to take quite some time but if you did not mind I sure would appreciate the help." I replied, hoping he would let his son help me out. "I do not see a problem with that. That is if he wants to." His dad told me. "Great. Do you want to tell him tonight?" I asked. "Why don't you ask him tomorrow. That way if he wants to he can ask me and I will agree to let him help. If he doesn't then it will be fine but that way he is the one deciding." His dad said. "Ok. I will." I agreed. We each said good bye and headed into our own houses. This was great. I now had a chance to get further into detail with Daniel about sex. The next day Daniel came over and as we worked I asked him about helping me paint the inside of my house. "I would love to...but..." Daniel answered with a very concerned look on his face. "But what?" I asked. "Well, I have never painted before so am not sure what to do or if I will be of any help." He told me. I chuckled then replied, "It is alright. I can teach you and yes I am sure you will be of help to me. Might even have more questions to ask me about other stuff." I gave him a look of hope of continuing the conversation about sex. He smiled knowing what I had meant before telling me that sounded good. We finished the yard work and before he went home we made plans to start paining Monday morning. This gave him a couple days to help his dad in his own yard. It also gave me time to pick out and buy the paint and supplies. That weekend I bought everything I needed to do the entire inside of the house. I took it all into the garage and stacking it all up into piles according to room. I then made a plan of what order to do the rooms and by Monday morning I was ready to go. Right on time Daniel rang the doorbell Monday morning. I opened the door and let him inside. This time he was wearing an old tee shirt and some old shorts. My heart began to pound as I knew what I had planned on telling him. I just hoped it would not scare him or make him run home and tell his parents. I was pretty sure he would enjoy what was in store the next several weeks. I took him into the garage and showed him all the paint and supplies. He was amazed it was going to take all that stuff just to paint the walls inside the house. I then took him around the house going from room to room in the order I had planned to work. I told him how we had to move stuff out or around inside each room and that we had to cover what was not removed. I explained how not only was the rooms getting painted but I would be doing some repairs and cleaning stuff up and getting rid of some stuff as we went. When we were all done with the plan we headed to the starting room. We moved a lot of the stuff out of the room into another room. There I would go through it tossing some out and cleaning the rest. That part would be done at night when Daniel was at home. I then sent Daniel to the garage to get the plastic, tape, and other things we needed to get started. We coved stuff up and laid out plastic on the floor to protect it from paint splatters. I explained each step as we went and told him that each room would be done the same way. "Now to get to work." I commented. "First we will need to tape off all the door frames, windows, and anything else we do not want to paint." I instructed. I removed the switch plates and outlet covers and told him to be careful around them because of the wires. The closer we got to starting to paint the harder my heart pounded. I brought in the paint and brushes and suggested we take a short break before painting. We went to the kitchen for a snack and drink. This was when my plan was either going to crash and burn or be successful. "Daniel, you know how we worked outside with no shirt on?" I began slowly with the plan. "Yeah." He replied being a little confused. "Well, when I paint inside I find it to be really messy." I told him then paused. "I figured that because Mom made me put on this old shirt and pair of shorts. She said it did not matter if they got paint on them." Daniel said. I took a deep breath and with all the courage I could muster I said, "I have found it easier to paint without any clothes on. That way I can just wash off and I am clean. I do not have to worry about my clothes at all." Daniel just looked at me like he was a deer and I was a car heading right for him. He said nothing but did not run from the house either. I figured I had better make him feel more at ease before I ran him off. "If you do not want to paint naked then that is alright but do you mind if I do?" I questioned. "Really? You do not mind if I take my clothes off in front of you?" He cautiously asked. "No. Why should I? We are both guys. So what's the big deal?" I said as I urged him to agree to strip naked. "True." He quickly agreed. "Well I guess we had better get at it." I told him. I grabbed an old chair that would be used to sit on to clean our feet before going into the rest of the house. I also took a step ladder into the room along with some towels, a pan of water, and some paper towels. Once we entered we would not need to leave until lunch. That gave us an hour or so before needing to leave the room. I then stood outside the room and began to strip. I removed my shirt first then my shorts and finally my underwear. I did not have shoes and socks on so in a matter of seconds I was standing in front of Daniel totally naked. Just before I removed my underwear, Daniel took his shirt off. Like me he already had removed his shoes and socks. "What's wrong? You do not have to take your shorts off unless you want to." I told him. "You will not laugh will you?" He hesitantly asked. "Laugh? At what?" I questioned. "You know." He answered as he looked down between his legs. "You are so big and I am so small. You also have hair all around it where mine does not." He then added. Now I just had to see him naked. I had not seen a hairless cock in a very long time and even though I was impotent I still enjoyed thinking and talking about sex. I promised I would not laugh. I also told him that when he got older his would be big like mine too. With a crooked smile on his face he began to slowly remove his shorts. My heart really began to pound as I looked at this little 11 year old boy in his cute underwear. He then pulled his underwear down and place them in the pile of clothes before we entered the room. Fuck his dick was cute. It was so small and hairless that I just knew I would have to do something to him to make him feel good. If I were still able to get an erection, I was sure I would have been as hard as a rock at that point. Might have been a good thing that I was not able to become erect because it might have had him run from the house in an instant. "I do not see any reason for you to be worried with your size and looks. I think it is really exciting to look at." I told him. "But yours has hair all around it and is so fat." He said. "Well I use to keep it all shaved off. That was when I was married. Guess I have gotten lazy since the accident." I explained. Doing just what I had hoped for, Daniel asked, "Shaved? Why would you do that?" "Because my wife would not suck it if I did not have it shaved. She really gave a good blowjob and so it was well worth it to stay hairless." I told him. "Suck it? She would put it in her mouth? Yuck!" Daniel yelped. I chuckled and answered, "Yeah. Do not knock it till you've tried it. Feels really good and is fun to do to others too." This sparked even more interest and questions. "You have sucked on one before? Another guy's?" He asked. "When I was a boy, yes. I too liked the hairless ones better. I really do not like getting those little hairs stuck in my throat." I explained. I guess between him looking at my naked dick, us talking about blowjobs, and me commenting about sucking little hairless cocks he was getting aroused. I could see his little dick was getting hard. It did not grown much fatter but it grew in length and by the time we had just begun to start painting his dick was about 4" long and just begging to be sucked. I showed him where to start and how to begin to trim stuff out. I did the upper stuff and by using the step ladder I was at a perfect eye level for him to get a good close look at my fat dick. We continued to talk about sucking dick and squirting cum. He asked how it tasted and I tried the best I could to tell him. The more we talked the harder he got and soon his little prick was bouncing up and down to the beat of his heart. I was just about to suggest I suck his dick so he would know how good it felt when the phone rang. I quickly checked my feet for paint and ran naked through the house to the phone. It was Daniel's mother. She was calling to let Daniel know his lunch was ready and for him to come home to eat. I told her I figured he would be eating with me but she said it was already fixed. She did say that the rest of the time he could eat with me. I went back and cleaned him up and had him dress to go home to eat. It was almost like he did not want to get dressed. I promised that once he came back he could strip as soon as he got inside the house. Daniel went home to eat while I ate a quick lunch. I then did something I had not done in years. I shaved off all my hair around my dick, balls, and butt crack. I almost felt young again. I did like the feel of being hairless and wondered why I had stopped shaving. Daniel came back and as soon as he had the door closed he stripped naked before walking through the house to the room we were working in. I was already painting with my back to the door when he entered. "I'm back and ready to paint." He cheerfully stated. "Great. Grab your brush and get started." I told him as I purposefully kept my back to him. "How was lunch? Your mother say anything?" I asked as I tried to keep my shaved crotch hidden. "Lunch was ok. Mom told me I would be eating with you till we finished painting. Oh, and she asked why I did not have any paint on my clothes." He answered. "Oops." I thought. I had not thought about that problem. "What did you tell her?" I asked hoping he did not say anything about painting naked. "I just told her that we had to move stuff and trim things out so we had not done much painting yet." He answered. "Good. You know not to tell them you are painting naked right?" I checked. "I would never tell them that." He said. "Good. Tonight when you go home tell your mother to send some clean clothes for you to put on after we paint. You can just leave your old clothes here. Each day after you paint naked I will clean you up and you can dress in your clean clothes. The next day you can tell her you will change here into your painting clothes and then change back when you go home." I told him then slyly I turned around so he could see my newly shaven dick. "Your hairless!" Daniel chirped. "You like?" I asked. "Yes. I like it much better this way." He said as I noticed his small cock springing to attention. "It looks so soft and cuddly. Ca...ca...can...I touch it?" He begged. "Sure. Can I touch yours?" I asked. "Ummm...Hmmm..." He responded. We each took turns touching each other and soon he was playing with my balls as well. I began to stroke his dick and play with his balls as his eyes closed. I really wished I could get hard but then again I had to remind myself that this was all for Daniel. I wanted to do something for him for all the work he had done for me and this was the only thing I could think of. "Would you like me to suck you?" I asked. "Ummm...Hmmm..." He purred. I sat him on the chair and got on my knees between his legs. I leaned over and took his entire shaft into my hot mouth. He gasped in pleasure from something he had never felt before. I worked my mouth up and down on his young hairless dick and my hands played with his balls. I worked one hand between his legs to his butt crack and massaged his butt cheeks as I sucked his shaft. He soon began to moan as I felt his balls tighten. I knew this meant he was about to cum but was not sure if he was shooting cum or not. It really did not matter because I was just about to give him his first blowjob. Cum or not he would remember it the rest of his life. "Ohhh...Ohhh...Mmmm..." He moaned as his hips began to fuck my face. I was not letting him go. I was going to take him to the top and let him have a nice loving orgasm without fear of getting caught. A minute or two later he made one last hard thrust up telling me he was there. I sank my face hard into his young tender crotch and sucked hard like I was trying to suck cum from his balls. His body began to shake and shiver as his hands grabbed the back of my head and held me in place. A few minutes later his body went limp and it was over. No cum but he had just had a fantastic orgasm. He opened his eyes and looked at me. He smiled but said nothing. His eyes was telling more than words could ever tell. "I guess you like that?" I asked. "I sure did." He said. "Was that your first orgasm?" I asked. "Ummm...Hmmm..." He moaned. "Guess I will have to teach you how to jack off and maybe some other stuff too, but for now we had better get to work." I told him. "Ok." He said and he struggled to get to his feet. The rest of the day was spent talking about sex and sex acts. I answered all his questions and encouraged him to ask more. By the end of the day we had the room trimmed out and with little or no paint splatters on us we were able to call it a successful day. He dressed and I reminded him on what to tell his mother. I put paint and supplies away and began to go through the stuff we had piled in the other room. Later I ate dinner and went back to work. The painting was going to be done only when Daniel was around because I was enjoying his company. I still had much planned for his payment for all his previous help and for helping me paint the inside of the house. The following morning I heard the doorbell and found Daniel dressed in the same old clothes he was wearing the previous day. He was carrying a bag which contained some clean play clothes that he was told to be careful not get paint on. I put his nicer clothes on the couch and told him he could dress just before going home. With a smile on his face he asked, "Does that mean I can paint naked again today?" "Sure. Let's go into my bedroom and I will show you where you can keep your painting clothes till we are finished. If you ever feel you want to put them on then you will know where they are." I told him. "Ok." He said. We then both stripped naked. We placed his shirt and shorts in the dresser drawer and he took his underwear off. He took them to the living room to put on when he dressed later. We met back in the room we were paining. I noticed he was already hard and knew at that point that was going to be the most fun painting I had ever had. "Looks like you are wanting some payment before we get started today." I commented as I looked at his hard little pecker. Giggling he said, "I really liked what you did to it yesterday. Can you do it again?" "Let's paint first and I will take care of your needs later." I suggested. I could tell he was disappointed but he said that would be fine. My plan was to talk about sex all day making him ready to explode by the time I made him cum. I knew that was mean but figured he would have harder orgasms that way. We began work and before we knew it we were slinging paint all over the place. I again was doing the part above him so when we were in the same area he was getting paint dripped all over his naked body. I can't say I was staying clean myself but I was not as paint soaked as he was. We stopped for lunch but before we left the room to eat I made sure our feet were free of all paint splatters. The last thing I wanted was paint all over the carpets. I placed a towel on the seat before he sat down to keep the paint on his butt from coming off onto the chair. I did the same to mine. I fixed up some sandwiches and fries and before long we were back painting again. He asked me about jacking off. I told him what it was but that I would teach him how to do it later. I guess I was a little afraid that he might do it more leaving less interest to my mouth and other bodily help. By the end of our painting day he was once again hard as a rock and was so excited about having another orgasm that he could hardly stand it. "Ok. I think we can stop here." I told Daniel. "Oh. I still have an hour before I have to be home." He informed me. "Yeah, but we have to put some of this away, get cleaned up, and take care of that hard stick that is sticking out in front of you." I explained. Giggling he grabbed his shaft and pointed it at me saying, "You like taking care of me as much as I do. Don't you?" "As much or more." I stated. I cleaned our feet off and took him by his hand to my bathroom. I started the shower and got the water warm. We got into the shower and I closed the glass door. I had him sit on the built in seat as I grabbed the soap. I soaped him up from head to toe then had him stand. I then did his backside paying close attention to his cock, balls, and butt. As I soaped up his hard shaft he moaned as I stroked it clean. I rinsed him off and washed out the paint from his hair. I did my own body next while he sat and watched. He asked if he could go my dick and balls. I happily handed him the soap and told him to have fun. He did to me what I had done to him. I again was wishing I could get hard from him playing with me. I rinsed off and turned off the water. I grabbed a towel and dried off my little helper and as he finished drying himself off I dried his hair with the hair blower. I did the same to myself as he watched. When we both were dry I took him to my bedroom where I had him lay on my bed. I looked down at his sweet innocent naked body thinking of all the fun things I wanted to do to him. His dick again was hard and pointing up at the ceiling. I snuggled up between his legs and took his shaft deep into my mouth. I sucked hard as I played with his balls. I managed to get my hand under his butt and finding his butt hole I made ready to add a little extra enjoyment to his orgasm. I sucked and stroked his shaft as my fingers played with his balls. The more I sucked and stroked the louder his moans got. I could feel his balls tighten up which told me he was almost there. Adding a little more play he let out a big moan as I could feel his dick beginning to twitch inside my mouth. It was then I shoved a finger up his asshole. His eyes popped open and a look of surprise showed on his face. That look was soon replaced by a look of extreme pleasure. His body shook so had the bed was moving. His eyes soon closed as his head with back and letting out a loud grunt I knew it was over. I pulled my finger from his ass as I pulled my face from his crotch. I gently pulled his legs back together as I moved up his body. I kissed his sexy belly button and each of his boy nipples. I then kissed him on his mouth. I turned an innocent friendly kiss into a passionate French kiss in an instant. He kissed me back having fun as our tongues had a battle between our mouths. I noticed the time knowing we had to stop. I took one last look at his naked body laying in my bed before I had him get up. We walked back to the living room naked where I watched him get dressed. I gave him a gentle kiss and as I opened the door to let him go home he gave me a hug. "I really had fun helping you today. See you tomorrow." He lovingly told me. "I did too." I said with a smile. The rest of the week was pretty much the same. I gave him a dry orgasm with my mouth at the end of each day but added something different or did it in a different way each time. Friday he begged me to let him suck my fat cock. So, that day we got in t he '69' position and I let him suck on me while I gave him another hard orgasm. I really enjoyed the oral sex from Daniel. I almost had and orgasm myself as I took him over the edge but it did not quite happen. Since I had actually been injured which was what caused my impotence it was even more difficult for me to cum than other men. I was just happy I was making the little boy feel good. By the next Monday he knew what to do. He walked right into the house without ringing the doorbell. Then as soon as he closed the door he stripped naked leaving all his clothes on the couch. He then would find me already naked getting things ready for the day's work. We had finished the room on Friday so after it had all weekend to dry it was time to pull all the tape off and put back all the switch plates and outlet covers. We then pulled up the plastic and moved the furniture back into place. We re-hung all the pictures and began to replace all the stuff I was keeping. I had already thrown out what I was discarding, well most of it anyway. It took all day to get that room back in place and to get the next room ready. We did not do any painting at all that day but we sure did enjoy working naked. I loved teasing him by touching his dick from time to time as we passed. He would grab my fat cock and tug on it too. I popped his ass a few times finding he liked being spanked. When the day's work was almost over I said, "I have a surprise for you today." "What?" He yelped. We went to the living room where I had him sit on the floor. I pulled a stack of porn magazines out of a box and placed them on the floor around his naked butt. "This week I will be teaching you about jacking off." I informed him. "Goody" He chirped. "I want you to look through all these and place them in five different piles. Each pile depends on how much you like what you see. If you like it a whole lot put in one pile. If you just think it is ok then in another pile. Then the other three piles are somewhere in between." I will give you a few minutes to do that while I work on going through the stuff we moved today." I instructed. He looked up at me with somewhat of a sad face and asked, "Are we not going to shower together today?" "No. We did not paint so we do not need to get any paint off of us. Anyway, you need the extra time to learn a new skill." I answered. He went through the magazines and I went to work going through the stuff from the second room. About a half hour later I returned to find him sitting in the middle of five piles of magazines and his dick was sticking straight out in front of him. "Looks like you liked what you saw." I chuckled while looking at his hard little dick. Fiddling with his cock he replied, "Yeah. I guess I did." I found out which he liked best and worst and I marked each pile in order from worst to best. I left the pile he like the worst in front of him and moved the rest away to my bedroom. This pile had mainly teenage girls licking pussy or shoving dildos in each other. There were four magazines in the pile which was one of the smallest stacks. I then had him go through and pick out his favorite picture from each and open the magazine to that page and lay them out so he could see them without moving. He did as I said without questioning why. When he finished I said, "Good. Now sit up here on the couch with me and leave the magazines on the floor." He was a little confused but did as I said. I then told him about stroking his cock and the parts that felt better. I told him about lubricant and how some guys liked it and some did not. I also told him how every guy was different and he would just have to try many different methods before he knew what he like to do the best. He maintained his erection through the whole talk making me wish I too was again his age and able to stay hard that long. "I am now going to show you the basic method and a few variations. See which you like best. I will then let you play with yourself before I let you cum." I told him as I took hold of his throbbing dick. Taking a light grip I began to stroke his shaft from the base to the tip. He began to moan as I made contact in just the right place. I then began to play with his hairless balls as I stroked. He moaned even more as I picked up speed. Adding a few drops of lube in just the right place I paid close attention to the skin just under the head of his cock. Daniel began to hump my hand as he moaned, "Ohhh...Yeah...That feels really good." I took him close but held back from letting him get too close to an orgasm. I tried different ways paying attention to different areas and using different strokes. When I was done I let him give it a try. He very childishly began to pump on his dick. I could tell he still needed more guidance so I placed my hand over his and showed him how to keep control of what he was doing. When I figured he had enough of my help I had him sit on the floor in the middle of the opened magazines. "Now let's see if you can jack off and have an orgasm on your own. Pick out your favorite stroking method and while you look at the different pictures you just stroke away. It might even help if you fantasize about doing things with them or having them do something to you. Let your mind roam and think of whatever you want to make yourself feel good. At some point you will hit just the right spot and your hand will fly and it will happen. The point is to feel good and have fun." I explained. He did as I said and I sat back and watched. At first he was a little shy looking at naked girls while touching himself. Then with me watching probably did not help any but I wanted to see what he was doing so I might could give him some pointers. Daniel's small hand wrapped tightly around his thin dick as he pumped away. His eyes bounced from naked girl to naked girl in the different magazines. He must have eventually found just the right picture and speed of stroking because his breathing became labored. He then began to pound his hand hard against his pelvic bone smashing his balls between his legs with each thrust downward. The speed soon picked up and his moaning was soft and gentle. Not long after that he began to pant as he tried to inflate his lungs. His hips began to thrust upward as his stroked got faster and faster. I knew he was now on his way to one of his exciting orgasms. This would be the first time I was actually able to see him cum. All the other times my face had been in his lap and I could not really see that much. His small fist was now working as hard and fast as a jackhammer as it tried chipping up a sidewalk. "Mmmm...Mmmm...Mmmm...Ohhh...Ohhh...I think. Ohhh...I think I am about...there. Mmmm...Mmmm...Mmmm..." He muttered. Then with a loud hard grunt and a hard trust upward, his body shook and his small hand gripped his dick as hard as he could. His butt soon fell back to the floor, his head tilted back, and his eyes closed tight as his entire body shivered violently. His body now heaving as his breathing was hard and fast. Soon as his body stopped shivering he fell back. His head laid on the floor as his legs stretched out in front of him. He still had a firm grip on his cock like a child holds his teddy bear at night. He gave one last thrust upward as his hand fell to his belly still holding on to his newfound toy. I let him lay there enjoying the remnants of his very first solo jack off session. I let him lay there as long as I could but knowing time was getting short I had to have him come back to reality pretty quick. "Daniel. You need to get up and get dressed. It is time for you to go home for dinner." I softly told the boy. "Ok." He moaned. He began to get up and found he was sore but did not know why. I told him that he had just used some muscles he had never used before but the more he jacked off the less sore he would be. He got up and while he was dressing he asked if he could take magazines back home with him so he could do it again later that night. I told him it was not a good idea but he could jack off in the shower or in bed. I told him he needed to be quiet so his parents did not hear. He gave me a hug and we kissed just before he left. The next day we began to paint so we had to shower when we were done. After we showered and were dry I took him to my bedroom and had him go through the second stack of magazines that he liked least. This was a stack of older women doing the same as the fist stack. This one did have a few guys in it but when he picked his favorite pictures they were not among the choice. This was a pillow humping lesson. I had him lay out the different magazines and I placed the pillow in the right spot. I showed him how to rub his cock on the pillow and then hump it like he was fucking a girl. He really liked this method and soon he was again shaking and shivering as an even more intense orgasm tore through his body. When he regained his composure and sat up I told him that when he began to squirt cum he would need to wear some underwear or if he could sneak a pair of his mother panties to wear to catch the cum then it would be better than squirting cum on his pillow. I told him that if he could not find some panties to let me know and I would get him some. Just before he got out of bed he looked at me and hesitantly asked, "Would any type of pillow work?" "What do you mean?" I questioned. "Well, anything squishy like a pillow?" He then asked. "What did you have in mind?" I replied. Almost afraid of asking he quietly whispered, "My teddy bear?" "Sure that would work. If the teddy bear does not mind." I reassured him. Daniel smiled and said, "I think he will like it too." Daniel got up and dressed and headed home. The rest of the week I showed him all kind of methods for self pleasure. Some he liked and some not so much. Each day I gave him another stack of magazines to look at until Friday when it was his favorite stack. This one had a bunch of young men touching each other. His favorite pictures were of two guys touching their dicks to each other some even with cum running down the shafts. We had finished up the second room and a bathroom that week. The following Monday was my bedroom and bathroom. We got things all moved around and like the previous week we finished a little early. This week I was going to let him pick his own way of having an orgasm. Some days he had me suck his dick and some he jacked off. No matter what method he used he came each and every day. The fourth week was all the halls, closets, and kitchen. This was an easy week and one day I picked out as a vacation day. When he arrived he was stripped naked soon as he closed the door just like normal. He looked around but did not find me. He called out trying to find where I was and I told him to come to my bedroom. There he found me naked like normal. "I thought we were finished in here." He said. "I was thinking we needed a break. How would you like to sleep with me?" I asked. "Wow! That was be cool." He yelped. I got into bed and had him get in with me. I wrapped my arms around him and kissed him hard on the lips. The kiss soon turned into a passionate French kiss. Our cocks began to rub against each other and we wiggled around. I managed to move him around until he was on top of me with his cock rubbing on mine. "Hump me like I was your teddy bear." I urged. That request did not have to be made twice. We kissed as I felt his hard dick rub against my soft fat cock. Fifteen minutes of humping and kissing as he was rewarded with a sweet orgasm. When he finished having his way with me we turned on our sides still facing each other and we both drifted off to sleep. Sometime later we got up and ate lunch. After eating we went back to bed where I sucked him off and once again fell asleep in each other's arms. Out of all the time we had spent together this day was his favorite. I too enjoyed the closeness we had that day. We finished the week up and got ready to do the living room and dining room last. We had everything taped and ready to paint by Friday making the last week an easy one. We painted and got it all back in place by Thursday which made Daniel sad. I told him to come back Friday so I could pay him for all his hard work. He seemed to be a little confused but agreed. Friday he came in and stripped naked just like normal. Looking around he again did not find me so he looked in my bedroom where he found me waiting on him in bed. "Do we get to sleep together again?" He asked with a hopeful tone to his voice. "First I have something special for you today. That is if you want to do it." I told Daniel. "Ok." He replied not knowing what to think. I handed him a couple of the magazines that had guys fucking other guys in the ass. I told him to look through them and tell me what he thought of the idea. It did not take long before I had my answer and he did not have to say a word. His cock instantly bounced to attention as he looked at dicks being shoved into other male assholes. "I like looking at them. It looks like fun." He told me. "You want to try it?" I asked. "You mean it?" He asked with an excited voice. "Sure. If you want." I said. I put a pillow under my butt and grabbed the lube. I showed him how to lube up an asshole to get it ready. I then put some on his super hard cock. Lifting my legs, I had him snuggle between my legs with his hard cock leading the way. I had not been fucked in the ass since I was his age so I knew my hole was going to be tight. I also knew with his thin dick it was not going to hurt and figured he would not have a problem shoving it in. I told him what to do and what to expect. He followed my instruction and soon I felt the tip of an 11 year old boy's penis knocking at the entrance to my asshole. "Ok. Good. Now push. If it will not go in then pull out a little then push back a little harder. Just be careful not to push too hard too fast. You have to be gentle." I explained. Doing as I said he began to push his dick into my wanting hole. It really felt nice as he slide it inside my hole. It was not too big to hurt and was not too small not to feel. I would say it was just right for fucking me with. He pulled back a little and then pushed in a little harder. Slowly I felt it press deeper and deeper into my ass. "Mmmm...That really feels good." I moaned. "Feels good to me too." He purred. I urged him to push as hard as he could because I wanted to feel his balls press against my butt cheeks. Pushing with all his might and weight I could feel the warmth of his balls pressing hard against my skin. My balls were also feeling his pelvic bone as he pressed hard into my crotch. We both moaned from the pleasure we were receiving. All of a sudden I watched as he took his small hands and began to play with my still limp cock. He began to stroke my dick as he slowly fucked my ass. His hand play soon turned into jacking me off at the same time his hips picked up some speed. He sped up to the point he could not balance himself and had to let go of my cock. His arms were then placed on either side of my hips as he put more weight onto his privates as they began to pound harder into mine. "Oh fuck! That feels good!" I yelped as I could feel him rubbing my prostate with each thrust. Daniel's breathing was taking too much energy to make comments as he pounded my ass with his 4.5" child dick. I urged him on as he pounded me harder and faster in the ass. "Cum for me Baby. I want to feel you blow a load of cum deep into my body." I said knowing he was still not squirting cum yet but thought it might encourage him to fuck me harder. He was giving me all he had as he pounded my body with all his weight. His balls smashing into my butt with each thrust. My own dick and balls flopping around as his body caused mine to be tossed around on the bed. Daniel hit some perfect spot in my ass that all of a sudden caused me to begin to have an orgasm. His panting got louder and harder as he rammed his cock home inside my body. I felt his cock begin to swell telling me he was about to cum. Oh how I was wishing he would shoot cum into my ass but deep down I knew it was not going to happen, not then anyway. Daniel gave a half dozen super hard jabs sending me over the top causing my body to shake from a much overdue orgasm. He too began to shake as his orgasm blasted through his small young body. We were both cumming together for the first time. When I came I shot a small amount of cum onto my belly. It was not much but was more than I had shot in many years. Daniel looked down at the cum I had shot and asked, "Wow. Is that cum?" "Yes. You did that to me and it felt great." I said then after a slight pause I asked, "Would you like to taste it?" "I...I...I...Don't know." He quietly answered. I encouraged him to at least try it by sticking his tongue in the puddle. I told him that if he liked it he could then lap it up. Doing as I suggested he leaned over and stuck his tongue into the cum puddle. Just the sight of him doing so sent a wave of pleasure through my body. Just a second after he tested the cum he began to lap up all he could find including sucking my cock dry. "Well I see you liked it. Too bad there is not anymore." I said. I had him pull his now limp did from my ass and I cleaned him up. We cuddled a while making sure we had a passionately hot French kiss. I held my sexy little boy in my arms as we drifted off to sleep. Like before we got up to eat lunch but soon after eating I offered him my ass for another fucking. This time I got on my hands and knees and told him to fuck me doggie style. He remembered what that was from some of our previous discussions. I was still pretty slippery inside and no bigger than he was I knew I did not need any more lube. He propped himself up and slipped his cock into my warm hole once again. I could feel his balls slapping the underside of my ass as he rammed his cock into my hole. He was really ramming me good as he tried to make both himself and I feel the best we could. With skin slapping sounds and the feeling of his cock being squeezed into a tight asshole, Daniel did not last as long and soon I felt his cock inflate followed soon by some hard thrusts and heaving breathing as he once again had a hard exciting orgasm. I slowly laid down in the bed while telling Daniel to keep it inside me. I then truned and he cuddled up next to me with his dick still inside my hole. He held on as we went back to sleep. A few hours later I told him to give it to me one last time. Still laying on our sides he began to pump it in and out of my ass. This being the third time that day he was running out of steam but with my butt clamped tight he had more resistance which triggered the last orgasm of the day for him. We got up and showered together. After our normal washing and before we got out of the shower I locked my mouth around his semi-erect dick and sucked him to a small but enjoyable orgasm. We finished up and got dried off before exiting the bathroom. I walked him to the door naked where he dressed himself. He was happy until that point. He told me how sad he was that we had finished painting but loved how he was paid for all of his help. He told me to let him know if I ever needed more help. I told him that at any point he just wanted to come over to talk or play to come on over. I explained that my hole was his hole and really wanted a load of his cum as soon as he was shooting. As for his painting clothes I told him I would keep them with me in case he was to come help me again. In reality I just wanted a part of him in the house so I could look at them when I wanted. I also kept the magazines and over time I let him have two at a time. He was told to make sure no one saw them and when he wanted to switch out he could switch them for two others. He liked that idea and eventually he began to shoot cum. It did not take him long after his first wet cum before he was deep in my ass again. I will never forget the feeling when he made his first deposit inside my asshole. I carried his load inside my ass for a day or two before it was expelled. Luckily he would give me a load from time to time. I miss some of the things we did together but after he got older he found both girls and boys his own age to fuck leaving me once again alone. He did manage to visit me until he went off to college and I will cherish those special times just like I do our first time together. The End