Date: Mon, 22 Jun 2020 21:32:09 -0400 (EDT) From: ShortStories@PlayTime69.e4ward.com Subject: Panty Playing Neighbors - Chapter 1 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 involving sex acts between adults and children in many different combinations some even being related. 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. ****Special Author's Note**** This is a trilogy that started with a single idea of a neighbor boy seeing the waistband and the seams of the panties worn by an older male neighbor. The first story expanded to a second then third making it a trilogy before the first story was even published. Each story has many chapters due to their length. The timeline order for the stories goes "Panty Playing Neighbors", to "My Little Beach Bunny and Her Children", and finishing with "When Families Cum Together". They have all been written and are ready to go, and will be published one to three chapters a week until all three stories have been posted in full. Each of the three can be read independently or out of order, but to get the full understanding they need to be read in order from start to finish. You will find, as you read, there is a lot of information telling what is going on and the thoughts of the different ones in the stories, and because of this information it might seem some chapters are more lacking in sex than others. Trust me the sex will show up again very soon. The more comments I get the faster I will release the chapters. Enjoy. Panty Playing Neighbors Chapter 1 by: Playtime69 I was bent over in the front yard picking up leaves and sticks from the previous night's storm when I heard, "Mr. Gray, my mother wanted to know if you had and extra dozen eggs we could borrow." I stood up and turned around to see Jake, the neighbor's son. "Hi, Jake. I think I do have some extra eggs. A dozen? That is a lot of eggs. What does she need that many at one time for?" I replied. "She has to make a lot of cookies for Madeline's school band. Madeline's band is having a bake sale tomorrow to raise money for the band trip coming up." Jake answered. "Well, let's go in and see what we can find." I suggested. "That was some storm we had last night." I mentioned. "I do not like storms. They scare me." Jake said. It was a very warm spring day and I had been outside working for quite some time and since it was hot I was only wearing shorts and no shirt. We entered the house and I was hit by the cold air as I said, "Wow it is cold in here, at least compared to outside." "Yea, I guess so. But you do only have shorts on." Jake giggled. I found the eggs and gave them to Jake. I asked him if that was all she needed and he claimed it was. We went back outside where I resumed my work and Jake went home. While working I got to thinking about how things got to where they were. Jake and his father had been my neighbors for most of Jake's life. Jake's parents were divorced when Jake was only a couple years old. I had even watched Jake from time to time when his father did not have anyone else to watch him. His father remarried a few months ago to a young sexy woman. She had two daughters. Madeline was 15 years old and was as sexy looking as her mother. Jennifer was 12 and was very cute. Jake was now 13 years old and was a very quiet nice looking child. He and Madeline were pretty much the same size except Madeline was a few inches taller than Jake. Jennifer on the other hand was a tiny girl all the way around, but then again she was only 12 and had not started her growth spurt yet. I am sure Jake felt some confusion from going from just him and his father to having three new females in the house. His step mother was very nice and was good to Jake, but still, Jake hit puberty at the same time two very cute girls moved into his house. Not really knowing them as sisters probably added to the pressure. I know if I had two cute little girls move into my house when I was 13 I would have wanted to fuck them both, but then again, I was an overly horny teenager growing up. Funny, I thought, I was still as horny as the day I turned 13 or maybe even more so. All this thinking of cute girls and how I would have wanted to fuck them if I were Jake had got the best of my cock and it had grown to its max length, 7.5". It really did not matter because I was hard a lot of the time I spent working in the yard anyway. Luckily, I had put on a pair of panties that morning so my cock was not falling out the leg opening of my shorts. Normally, I did not wear anything but shorts but when I did wear more it was always panties. I loved the way the soft cotton material caressed my cock as I walked around. Some I wore were plain and some were very childlike and cute. I even had some that was very sexy like the thongs and g-strings. I was just about finished cleaning the yard when I heard, "Fruit of the Loom or Hanes Her Way?" This took me by surprise. I turned around to see Jake again. I knew what I had heard, but was confused on why he had asked. I was not even sure of how I should answer. I wanted to pull my shorts down and say, "You tell me." But, I figured this would not be very proper. "Ummm. I am not sure, why?" I finally decided on saying. "I like Fruit of the Loom best. They are cuter and feel softer." He answered. Then looking at my still semi hard cock he added, "I saw the waist band when you were bent over and that along with the seams I could see when your shorts were tight I could tell you wore panties. I just cannot tell which kind they are." I was so surprised by what he was saying I was without words. I wanted this to go further but was not sure how far to take it. I decided to let it go as far as Jake was willing to go so I asked, "You wear panties?" "I do sometimes. I wish I could wear them more. It started a couple weeks ago." He began saying when I stopped him. "Would you like to go inside and continue this conversation?" I asked. With a big grin on his face he answered, "Yes!" "Ok. Let me get finished here and get the tools picked up first. Go tell your step mother where you are so she will not worry." I said. "She knows. Her and my step sisters are still busy making cookies and will be busy for quite some time. I will help you with your tools." Jake replied. We got the work finished and things picked up then went to the patio to chat. We sat in a couple chairs next to the pool and picked up the conversation where we left off. "So, how did your panty wearing days start?" I quickly asked. "Like I was saying, a couple weeks ago I had run out of underwear and Mom (Meaning his step mother.) told me to get a pair of Madeline's panties to put on. It was a Saturday so since there was no school and we were about the same size I did not think much of it. That was until I put them on and the material tickled my dick. It was a soft gentle touch, not like the hard thick material from my underwear I had been wearing. Well, my dick began to grow as I thought of how Madeline's pussy had been where my balls were, and before I knew it I was hard as a rock. I tried to get it got go down, but the more I tried the harder it got. Finally, I went to my bedroom and laid down on my bed face first. The pressure just added to the feeling. I began to rub myself on my bed and before I knew it I came in the panties. I wiped as much as I could but still had to wear wet cum filled panties around till they dried. Now, every chance I get I put her panties on and wear them under my shorts. I have yet been able to be alone with them long enough to cum in them again. When I saw that you wore panties I just had to talk to you about them. What are your favorite type, color, style? Do you cum in them?" He began asking. He then paused and asked one final question, "Caaannnn I seeeeeeee themmmmmm?" I was so surprised I was not sure what to say. I knew what I wanted to say. But, still. I knew what I wanted to happen was not what should happen. My horniness got the best of me and I asked, "Are you wearing panties now?" Jake looked down and quietly answered, "Yes. I went home with the eggs and just had to put her panties on before coming back over." "Then to answer your question, I will show you my panties if you will show me yours." I answered with a grin. Without another word he stood up and pulled his shorts down leaving him standing there in front of me wearing just a pair of his step sister's panties. I returned the favor and stood up pulling my shorts down and off. His panties were bikini style with a cute floral print using soft pink, blue, and yellow flowers. I had on hi cut style plain white pair because I did not have any idea I would be showing them off to my 13 year old panty boy neighbor. We both had hard cocks straining at the front of our panties. Mine was measuring about 7.5" while Jake's looked to be about 4". Fuck, I wanted him inside my butt hole, but then again, I wanted to just look at him while jacking off too. We continued to talk about all the different panties that both his step sisters wore and what he like better. We also talked about his step mother's panties and all the sizes that they all wore. He told me which he liked better and what he would like to wear when he got a chance. Then he took me by surprise and asked, "When did you get started wearing panties?" "Well, I guess it started when I put on a pair of my ex-wife's panties while she was at work one day. They felt so good that I wanted to leave them on as long as I could. She came home from work early and caught me wearing them. I was surprised she did not get upset. It was just the opposite. She loved the way my cock looked pressed against the fabric. Over time she bought me some different ones and even a nightie to wear when we had sex. What I did not know until later was that she liked seeing me in them and the nightie because she was gay and really was thinking of me as another woman. A few years later she finally left me for a girl she worked with. They now live together across town. Luckily she left me several pair of panties and some nighties." I explained as both our cocks grew to a painful hardness. I was just finishing up and about to ask Jake about his masturbation and sexual habits when the doorbell rang. We looked at each other like we both had been caught doing something we should not have been doing. Our cocks seemed not to care at all with them both staying rock hard. The doorbell rang once more along with a knock on the front door. Without a word said we both pulled our shorts up over our panties and hard cocks. We both walked to the front door to see who it was. I opened the door to see one of the cutest little girls around. It was Jake's younger step sister, Jennifer. "Hi, Jennifer. You sure are looking good today. What can I do for you?" I asked as I took a good look at the way she was dressed, or should I say the small amount of clothing she had on. "Hi, Mr. Gray. Mom sent me over to get Jake. Dinner is ready and she wants him to come eat." She smiled as she answered. I looked at the clock and noticed we had been talking for several hours then said, "Oh, time got away from us I guess. We had been by the pool talking. Guess you better go home and eat before she sends over the Calvary." I then added, "You come back anytime to talk more about..." I stopped just before saying, "panties" because I was not quite sure what Jennifer might say or do if she knew we had been talking about panties. Jennifer smiled and her and Jake left. I decided to eat before jacking off to the thought of Jake wearing panties while playing with my cock. I was just finishing up when I heard the doorbell ring. "Who could it be this time?" I thought to myself. I went to the door and opened it up to find Jake's father. He had a strange look on his face, kind of like he knew something that I did not want him to know. I was going to play it cool so I said, "Hey, what's up?" "Can I come in?" He replied. "Sure, sorry." I said as I moved from the doorway so he could enter my house. "I hate to bother you, but my wife said I should come talk to you about something." He mumbled like he was being forced to say something he did not want to say. I just knew Jake had said something or had been caught wearing panties and had said we had talked about me wearing panties in front of him. I was not going to tell him any information without knowing he already knew about it first. I wanted to get this over with so I asked, "What is it?" "I guess Jake told you that Madeline and Jennifer have to take cookies to the bake sale tomorrow. But, what he probably did not say was that I am expected to go with their mother to help set up and help run the sale for the band members." He was explaining when I broke in with, "No, he did not mention that." Jake's dad then continued by saying, "Well, that just leaves Jake. I know he will be bored cause there will not be anything for him to do. I was just wondering if he could stay with you. We will be gone from about 8:00 am till about 4:00 pm tomorrow. I know this is short notice and I should have asked earlier, but it just slipped my mind." What a relief. I was so glad it was not what I expected, I quickly replied, "Sure! No problem." Then I added, "Did you ask Jake if he wanted to stay with me tomorrow?" "No, but I cannot see and issue with it." He answered. "Ok. Just have him come over when you leave in the morning and tell him to bring a swimsuit so we can do some swimming." I suggested. He thanked me and went home. I was so excited about what might happen the next day that I had a hard time going to sleep. I made sure I did not jack off until I was with Jake. This was going to be the most fun I have had in many years, I thought to myself. The next day finally came and just before eight Jake rang the doorbell. I answered and let him inside and closed the door. We smiled at each other as I asked if his parents had left. He told me they had left about half an hour ago and then unexpectantly said, "Before you ask, yes, I am wearing Madeline's panties." I smiled back and said, "Great. Can I see?" "I will show you mine if you will show me yours." He answered with a dirty grin on his face. Without another word, I dropped my shorts revealing my hard cock pressing against my cute pink panties that had a sexy little bow in the middle of the waistband. He then dropped his shorts giving me a view of his sister's lavender flowered little girl panties. We both smiled as we continued to look at each other's privates. I broke the silence and odd looks by asking, "Would you like some breakfast?" "I already ate." He replied. "Well you can come into the kitchen and chat while I fix me something to eat. You can put your bag on the couch for later." I told Jake as we walked into the kitchen. I started off with basic conversation about school and the subjects he was taking. Pretty much he was just answering my questions and not giving any information I did not request. I do not know if he was tired, still asleep, or just scared to talk. I just know that each question I asked had a reason. I was trying to find out what he thought about sex and what he had been doing with himself and others. I did get out of him that he was taking a sex education class in school but it was just giving him basic information with few exciting pictures or films. Not getting anywhere I went a different route. "Do you have any friends in school?" I asked as I began to dig deeper. "I have a few I talk to and have even spent the night at some of their houses before." He answered. "Do they have sisters?" I probed. He looked at me funny like I was asking stupid questions, but he did answer with, "One has a younger brother, one has a much older sister, and one has a sister a little younger than he is." "You ever ask them about their sister's panties?" I continued digging. "No! I would be too scared to ask them about panties or even if they do anything with their sisters." He quickly answered. Still wanting to get the information I wanted, I kept asking questions. "Have you ever seen them naked?" He was a little slower answering this question but finally said, "I have seen them in PE class at school. They all wear normal underwear. Some have bigger cocks and some are smaller. No, I have not seen any of them at school with a hard dick, so I do not know if they are really bigger than me or not." Finally, I am getting somewhere. He is finally giving me more than just basic information from my questions. "So, you have not seen any other guy's hard cock before? In person that is?" I questioned. He did not say anything for a while but finally replied, "Well, there is one boy I have 'done' something with." Yes, Jackpot. "Tell me about it." I begged. I then added, "Are you sure you do not want some bacon and eggs with me?" "It does smell good. I guess so. If you do not mind." He said avoiding the real question I had asked. "Ok. No problem. Now tell me about your friend you 'did' something with." I begged. He looked down like he was ashamed to tell me but was going to anyway. "Last year a friend of my step mother had an emergency and could not find a sitter for her son. They live just a couple houses down. You might know the little boy, David?" I nodded my head, 'No' as he continued talking. "He was 9 years old when I watched him one evening. I was 12 so they figured it would be ok. I got there and we watched some TV for a while then heated up dinner. We ate then watched some more TV before I told him to get ready for bed. He went into his bedroom and then called for me to come help him. I walked in and he was standing there naked." Ok now this is getting good. My cock even thought so as it was now growing inside my pink panties. I just was really curious of how it was going to end. Still talking as my mind was racing, "His little cock was sticking straight out in front of him. It looked to be about two and a half inches and about the size of a pencil maybe a little thicker. I asked him what he needed help with and he said he could not find his pajamas. Well, I know mine is kept under my pillow so I looked there first. I was right. I figured he already knew where they were so figured he wanted something else. His cock was still at full attention but now he began to touch it and pull at it. My cock had now began to grow while watching him play with his. It was like he was putting on a show for me. I asked him if he wanted me to do that for him. Meaning play with his little dick for him. He nodded his head, 'Yes', so I reached out and began to pull at his dick like I did mine. I had been jacking off for a couple months by now and knew how to make myself cum really hard. While I played with his tiny cock he reached out and pulled at my shorts. At first I pulled back but figured if he wanted to see and play I would let him. I let go of his cock and pulled my shorts and underwear down and off. My cock bounced out as it was freed. It measured about 4" then and about twice as thick as his cock. He quickly wrapped his tiny soft fingers around my shaft and began to play. I showed him how to correctly play with a cock to make it feel good and allowed him to stroke me till I was about to blow my load. I told him I was about to cum. He did not know what that was so I had to explain. He also wanted to know if he could cum and I told him that he was too young to squirt cum right now but someday it would happen and he would not be able to keep his hands off his penis. He wanted to see me cum so I had him lay on the bed and I got above him so he could see my cock. I had him start stroking me again and just before I came I took over. I pounded my cock like crazy as my cum flew in all directions, most of which hit David's little cock and thin stomach. I then played with his tiny cock some more before getting some tissues and cleaning us up. He got up and I got him dressed. He then asked me why I had hair around my cock and he did not. I told him it was because I was older and he would get some hair soon. I did find his hairless cock to be really cute to look at and wondered what it would be like toooooooo..." His comments blew my mind as I listened to him explain his first experience with another boy. My cock was now about to poke a hole in my panties it was so hard. Wondering where his talk was going to go if it had not ended there was sending my imagination into overdrive. Trying to jump start his talking I said, "Hairless cock like this?" And with that, I pulled my pink panties down with one quick action. They fell to the ground and I stepped out of them as my cock stuck straight out in front of my balls. Jake took a gasp of air and yelled, "You do not have any hair! Why?" "I like it that way for many reasons. You like?" I then asked. "Yes! very much! Can I touch it?" He begged. "Not right now. If you touch it now it might just shoot cum all over you and since breakfast is ready we need to eat before it gets cold. But, why not pull your panties off so you will be naked too?" I suggested. Without a second thought he pulled his panties off freeing his rock hard 5" cock that was in a nest of black pubic hair. I had never seen so much hair around a young boy's cock before. Not only was his cock buried in hair but his balls were also covered in the same black hair. I much more preferred bald cock but his was interesting to look at. "Nice bush around you cock and balls." I commented. "Now let's eat." "Thanks." He said as we sat down to eat. The conversation continued and now that I had him relaxed on the subject of sex we would be able to openly chat about it. Finishing breakfast I suggested we clean up and get into the water for a while. We did not swim but simply floated and sat in the water as our food digested. Later we got out and rinsed off before sitting by the pool. "Can I touch it now?" He begged. I moved toward him so he could touch my cock and balls. While he played with me I reached down and began to play with his privates. While we played I asked, "Would you like to learn how to give blow jobs?" "I gueeessss so." He managed to get out. I pulled back and bent over taking his cock into my mouth. I caressed his balls as I sucked on his cock. Sliding up and down on his shaft with my lips locked around his member was both an enjoyment to myself and to Jake. I got him close to an orgasm when I stopped. "Now it is your turn. Just suck on my cock while sliding up and down on my shaft. For more enjoyment you can play with my balls at the same time" I instructed him. We switched positions and he began to suck on my member. He was a little rough around the edges with what he was doing but I think over time he could get to be an expert cock sucker. I was about to shoot my load when I pulled back making my dick pop out of his mouth. "My turn again, but this time I am not going to stop. Just pay attention to what I do to you so you will know what to do to me." I explained. We switched again and I went down on him once again. This time though when he got close I shoved my nose deep into his pubic hair as his cock went to the back of my throat. He began to buck against my face causing his balls to slap against my chin. It was such an exciting time for the both of us that I did not want it to end. I tried to force him to take his time cumming but he fucked my face hard and fast and I was not able to stop him from cumming. His cock shot his cum down my throat in a direct path to my stomach. We quickly switched so my cock was now deep inside Jake's mouth. He once again began to suck and fuck my cock with his mouth and tongue. It did not take long before I was ready to spew my load. I shoved my cock deep into his little mouth as I emptied my balls into his stomach. When done I pulled out and looked into his face to see if he liked it or not. "That was really cool." He quickly commented. "I cannot wait to do that again. I want to teach David that too. I would love to suck his little dick." "That is fine. Just be careful and do not get caught giving him a blow job." I recommended. "Hey, come see what I brought from my house." He giggled. I figured that the bag be had brought just had his swimsuit and a towel but boy was I wrong. We walked into the living room and he opened the bag and dumped the contents on the couch. Out flowed a pile of panties. Even though I had just cum I was already getting hard again. "This pair is my mother's." He said as he held up a sexy pair of red and black lace panties. "These are Madeline's." He said as he laid out three different pair of very cute panties. "And these are Jennifer's." He then added as he laid out some cute little girl panties. I just wanted to lay in the pile and play with and cum on each and every one of them. My cock now fully in fuck mode was bouncing up and down as I gazed at all the sexy cute panties. Jake too was really excited as his cock was also back to being rock hard and ready to shoot another load. "I have an idea. Will this pair fit?" I asked as I held up a pair of Jennifer's little young looking panties. They were so baby like I just wondered what her pussy looked like tucked away inside the panties. Jake pulled them over his cock. They just barely covered his cock head. Then he turned around so I could see his pantied butt. Fuck he was cute in the baby panties. I then put on a pair of Madeline's stretched out panties. If they had not been some well worn stretched out panties I would not have been able to get them on. I too turned around so he could see my butt. He took a swipe at my butt landing a perfectly applied spank. Little did he know that I loved being spanked while fucking. I laid down and had him lay on top of me. I then told him to put his cock on top of mine and to fuck me with his cock. He began to fuck me with his panty covered cock. "Fuck, Jake. That feels great!" I moaned into his ear as he pumped up and down on my pre-cum oozing dick. This talk make him even more excited and he began to fuck me harder and faster. I continued talking dirty in his ear saying, "Baby, fuck my panties. Think of me as your sister. Would you like to fuck your sister's pussy? Dream of her pussy inside the panties and you dick fucking her pussy while Jennifer watches and plays with her own panty covered pussy. Yes, right there!" He had hit just the right spot and I was just about to cum when I heard him grunt. His cock had erupted cum inside the panties and I could feel it leaking onto the panties I had on. "No!" I thought to myself. He came and I am almost there. I cannot stop. I had to cum or bust. I grabbed his butt cheeks with one arm and his bare back with my other arm and I picked him up. I laid him back down on the couch and laid on top basically switching positions. I then reached between our bodies grabbing my cock inside my panties. I pulled it and my balls out the leg opening of the panties. I then shoved my cock head inside the leg opening of his panties and pushed. It slid up next to his cum covered dick. It was almost like sliding it inside a wet pussy. I began to fuck his dick with mine. The orgasm began to build once again and within five minutes I had blown a load of my cum inside his panties mixing with his cum. That was the hottest sexual thing I had done in years. We laid together for quite some time before we separated. Sitting upright on the couch we looked at the mess we had made inside his sister's panties. We smiled at each other then talked about how much fun that was. I told him we would wash and dry them so he could put them back without them finding out. I was surprised it was already lunch time and we only had a few hours left to play. We stood up taking the cum soaked panties off. Without cleaning the cum off our cocks, I put on the red and black panties that was his mother's, and he put on a sexy pair of Madeline's. We left the cum soaked panties on the floor and went to the kitchen to fix and eat lunch. While we ate I asked him if he would fuck my asshole. He was so willing to do so I thought he was going to cum in his sister's clean panties. After we finished and got cleaned up we headed to my bedroom. I grabbed the lube and dropped my panties. I lubed my asshole and after he dropped his panties I lubed his cock up getting it hard again. Getting on all fours I said, "Here, fill my butt with a load of your little boy cum. This time while you fuck me I want you to spank my butt while you pump your cock in and out." He got behind me and slowly slid his cock into my hole. He began to pump in and out. I then felt a mild slap to my butt. "Mmmmmmmmmm! Yes! Fuck me. Spank me!" I demanded. Smack. I felt another spank to my butt cheek. "Harder! Spank my butt harder!" I begged. Smack! "Harder! Harder! Spank my bare butt!!!" I continued begging as I tried to fuck back as his cock pounded my butt hole. Smack!!! Smack!!! Smack!!! "Oh, Baby, Yes! Perfect! Now cum inside my ass!" I pleaded. He quickly picked up speed as he fucked me harder. Adding more slaps to my reddening ass was giving me pleasure on top of pleasure. Finally he erupted. He shot so hard I could feel his cum filling my hole. When he was finished and pulled his dick from my body, I quickly turned around jacking my pre-cum dripping dick. Aiming at his face, I shot my load. It hit his nose, forehead, lips, and chin. He licked his lips as I bent down and kissed him on the mouth. He kissed me back as we hugged each other. "Would you like to fuck me in the butt?" He asked. "Yes!" I excitedly answered. "But. Sorry to say. Your little hole would not be able to handle my fat cock. I could make it fit but it would really hurt you and if you were ever examined the damage would be noticeable. I really wish I could and maybe in a few years but for now we will have to pass." I explained. "Pleeezzzzzzz?" He begged. "I will not tell anyone." He then promised. I could not believe it. My cock was growing hard again. I had not had this much sex in years and it looked like my dick was not going to give up anytime soon. "Sorry. I just can't." I was saying but he looked at me with very pouty eyes so I said, "I tell you what I will do. I will rub my cock on your butt crack and just as I begin to cum I will shove my dick head into your asshole entrance. I will not be able to get the entire head inside you but will give you some pain and feeling of being fucked. I will then shoot my load inside you so you will be able to feel my cum inside your butt." He smiled and said, "Thanks." I had him lay on the bed with his legs spread. I climbed between them with the lube. I put lube on his butt hole and on my cock head. I then put more on my finger and slid my finger inside his ass. Fuck he was tight. I had to really work to get my finger inside and I could tell he was in a lot of discomfort as I did so. He did not complain but I could tell he was glad I was not going to fuck his ass with my cock. I put my cock in his lubed up crack and began to fuck him. It felt so tender, so sweet, so young, and so wrong at the same time. The pre-cum was just flowing from my dick like a running faucet. I knew it would not be long before I shot another load and this one was going to be big. "Get ready. I am about to fill your ass with my daddy cum." I moaned. I could tell he was a little nervous but I had gone this far and was not going to back out now. I gave it a few more minutes and just as I was going to blow I placed my cock head at the entrance to his ass. I shoved as hard as I could without doing damage to his hole. The tip of my cock entered his hole just enough I could feel his inner body heat. It was just enough I could get the sensation of being inside and that was all it took. I exploded with a unbelievable amount of cum. All of which was shot deep into Jake's tight ass. We both moaned together as the cum left my body and became part of his. I pulled my cock from his tender ass as I began to deflate. We cleaned up our mess putting all the panties in the washer. I started the washing machine and we took a shower together. We did some talking about how he could try to get into his sisters' pussies which then turned into one last jack off session while looking at the panties we did not mess up. When the laundry was finished, he took the panties home and put them away. We then just sat in front of the TV waiting on his family to come home. His father came over and thanked me for watching him. I told him that it was my pleasure and would not mind doing it again someday if needed. I wanted it to be sooner than I let on. It was definitely one of the best sexual experiences I had ever had. I think the only thing that would have made it better was to be able to fuck Jennifer, Jake's little 12 year old sister. A few weeks later Jake saw me working in the yard and came over to talk. With a smile on his face he asked, "Mr. Gray, how have you been?" Then after looking around he quietly added, "Been playing in anyone's panties lately?" "I wish. Are you going to volunteer your panties?" I replied. Giggling he answered, "Sure. But Saturday night I have to babysit David again. This time I am going to see if he will give me a blow job. I want to see if I can give him one too. I can't wait." "Sounds like fun. Just make sure you do not get caught and do not tell anyone what you are planning on doing." I suggested. "Ok." He halfheartedly replied. The thought of Jake having a now 10 year old hairless cock in his mouth was more than my cock could take. That night I blasted a load of cum in my panties and then slept in them for fun. The rest of the week I planned on doing nothing with my dick. I guess I was hoping Sunday Jake would come by and give me a blow by blow of what went on the previous night. Saturday night was especially hard because knowing what Jake had planned and my cock not having had any attention for several nights was causing it to ask to be touched. I ended up putting his cage on so I would not be tempted. **Special Note** There are 5 chapters in this story then the trilogy will pick up in the next story called, "My Little Beach Bunny and Her Children."