Date: Wed, 5 Dec 2018 14:00:52 +0100 From: Lycra Boy Subject: Dylan's After School Program Dylan walked up the stairs to my apartment and through the door as he usually does without knocking. Hello, Dylan is that you? I heard him yell yep as he came through the door. Dylan would come over while his mom was at work, and I am home early most afternoons. Dylan lived a few apartments away, so there wasn't much concern about him making his way to see me once he got off the school bus. Hey Dylan, I said as he ran over and gave me a hug which almost knocked my laptop onto the floor. I laughed at his enthusiasm as he sat down on the couch next to me. He asked what I was doing and I said just finishing up some work. I put my laptop away as Dylan kicked off his shoes and got comfortable on the couch. I had the TV on as background noise, but he's been here before and knew how to work the remote to find a channel he liked. We started watching TV as he snuggled up next to me, but my attention left the TV and landed on Dylan. He was wearing a pair of mesh shorts and a t-shirt. I put my arm around him as my hand draped over the side of his torso. My other hand I used to give him a quick hug and strategically left it rest on his leg. As the show progressed, I carefully slid my hand up his leg trying to not draw too much attention to it. I reached the opening of his shorts and moved my fingertips to his inner thigh. I adjusted myself to conceal my growing erection, which wasn't easy as I was wearing a t-shirt and my lacrosse shorts from high school. He looked up at me and asked, what are you doing? I got nervous and a little embarrassed and asked what this? I slid my hand a little further up his leg into his shorts and back down his leg again. He said, yes that. I asked him if it didn't feel good. Dylan replied, no, but it feels weird and kind of tickles. Oh you mean this, I asked with a smirk, as I began to slide my hands faster up and down his leg. Yes, he yelled out as he started to giggle. I moved my hands to his sides and started tickling just beneath his rib cage. He started thrashing about and laughing out loud. He jumped to try and get away but ended up stumbling and landing into my lap. We both froze as my hardon pressed against his back. What is that, he asked as he turned to look at it and then at me. Is that your wiener? I could feel my face turning red as I answered yes. He asked why it was like that and I responded that it happens when it gets excited. Dylan had a look on his face that he could relate to what I was saying, and said oh ok. I slid back onto the couch as Dylan stayed where he was looking like he was taking all the new information in. He put his hands down to his sides and slid back against me again. We started watching TV again as he pulled my arms around him into a hug around his stomach. I started to relax a little, but then he reached back and started to feel my hardon! I asked Dylan if everything was ok, he said yes, but said he was curious. He felt the tip of my cock through the mesh fabric and moved down my shaft until he reached my balls. Wow, he said, yours is much bigger than mine! I said don't worry it will get bigger as you get older. He paused and pulled his hand away. I asked again if everything was ok. After a minute or so he said yes as he stood up slowly. I thought he was going to go running for the door, but then he grabbed the bottom of his t-shirt and pulled it off. My hardon was straining against my mesh shorts as he turned and walked towards me. He asked almost in a whisper if we could do what was on the video that I was watching. I got a surprised look on my face as I had forgotten he had walked in on me watching porn on my laptop the other day. I asked, are you sure, I don't want to hurt you. He said, I trust you. I reached out and cupped his boy butt and pulled him close to me. I leaned in and kissed him as he started kissing me back. I started to tug on his shorts as they slowly slid over his bubbled-butt and landed at his feet. He stepped out of them and was left only wearing a pair of Lycra boy shorts he wore when going swimming in the neighborhood pool. I could see a bulge in the front of his trunks, he looked down at it and smiled saying it was excited too. He put his hands on the waist band, but I stopped him and said, I'll be right back I need to get some supplies. I quickly left for my bedroom to grab lube and an inflating device. As I was about to leave my bedroom, I heard footsteps running down the hall as Dylan ran into my room and jumped onto my bed, completely naked! I smirked and placed the items on my night stand. I removed my shirt as Dylan came over and began pulling my shorts down. He put his hands on my cock and began licking it since he could only fit a little of the head into his mouth. I moaned a little and asked where did you learn that? He said, I have internet too you know. I smiled and enjoyed the sensations he was giving me. I could feel myself getting close, as I stopped him some pre-cum came out as he licked my head. He smiled and said mmmm that tastes good! I laid him onto my bed as I moved down to his boy cock and slowly slid my hand up and down his shaft. Once it started to respond I slid it into my mouth allowing my tongue to massage it along the way. I could feel his body start to tense up and shake as his cock twitched in my mouth several times before relaxing again. Dylan asked what that was and I said it was an orgasm. He asked if anything came out and I said no, but that will happen as you get older. I asked him if he was ok and was comfortable moving forward with our experiment. He cautiously said yes and I said that I would try to keep him as comfortable as possible and let him know what to expect. He relaxed a bit after that as I slid my hand down his thigh and gave his ass a good squeeze. I told him that we would need to do some stretching before we could continue. He started to stretch out his arms and I laughed a little and said it's a little different than that kind of stretching. We'll be stretching here as I pressed a finger against his boy hole. I put some lube on my finger as I had him roll onto his stomach and spread his legs. I then pulled his cheeks apart and rubbed a finger around his ring. He gasped at the coolness of the lube. Once the lube was applied I told him he would need to try to stay completely relaxed. As he did I could see the tension disappear a bit from his sphincter. I pressed my finger onto his boy pucker with a bit more pressure. He moaned a little as the tension returned and I reminded him that he must relax. I tried my finger again as it slowly sank passed his ring. He let out another moan and I said you're doing great, just stay relaxed. My finger finally made its way into his anus and once it was all the way in I held it there for a few minutes before slowly pulling out and inserting two fingers this time. Once both fingers made their way fully inside him I spun them a bit to make sure he was being stretched in all directions. He moaned a little and I asked if he was doing ok and he answered with a soft yes. I left my fingers in for another minute and slowly pulled them out. I said ok now we need to stretch a little bit further, but I can't use my fingers if we want to stretch you properly. I showed him the stretching device and explained this device goes inside you and starts to stretch you out. It's on a timer so once the timer goes off, after about 20-30 minutes, you should be fully stretched. Ok? He nodded and I began to lube up the device. After adding more lube to his boy hole I began to slowly push the device into him. I got the device half way in and he said it was starting to hurt and he began to wiggle trying to move away. I said you're doing great; just remember to relax, just a little bit further. He became calm again and I continued to push the device further in. Once the device was in, I started the timer as the device slowly started inflating. I picked him up and carried him to the couch where I powered on the gaming console and told him he could play games while the device ran. About half way through I could see him start to 'play through the pain' as he began wiggling his butt. I reminded him again to make sure he stays relaxed and if the pain gets too bad to rub his wiener and make it hard. He looked at me in disbelief, but decided to give it a try. He rolled onto his side and we noticed that he was already hard from the device pressing against his prostate. He started to rub himself and smiled as the pain started to fade. A few minutes later he decided to sit up on the couch, forgetting for a moment that the device was still working inside him. As he sat on the couch it pushed the device in a bit further. He yelped and started to rub himself again as he leaned back onto the couch. Not too much, I joked, save some for me! He spread his legs and put his feet on the coffee table to alleviate some of the pain and continued playing his game. The timer finally went off just passed 20 minutes. He looked relieved for a minute, but I said we should leave it in a few minutes longer to make sure he was stretched completely. A few more minutes went by and I could hear a slight moan coming from Dylan as he began to rock his butt into the couch. That was my indicator that he was ready. I said ok let's take it out. We went back to the bed and he laid down on his back and spread his legs. I began to slowly pull the device out; Dylan hummed a little from pain and relief as I pulled it out, released the air and placed it in the sink to clean later. I got up on the bed between Dylan's legs and spread his cheeks a bit. I could see his hole was staying open and was wider now. I asked him again if he still wanted to do this. He said after doing all that, yes I am! I picked up his feet and placed them on my chest. I moved closer to Dylan and let my cock rub against his crack. I wanted to get inside him before his hole closed back up, but didn't want to go too fast. I said ok, here we go, don't forget to stay relaxed. He nodded eagerly. It was time to feed my cock. I got a clump of lube and added it to his hole and the rest on my hard man meat. I spread his cheeks again as I aligned my 6.5 inches with his hole. I learned forward and began to press against his eager boy hole. I was met with some tension as I had to reduce pressure and reapply. Finally, on the fourth try I applied a little more pressure and my cock head broke through the seal. Dylan let out a whimper as I moaned from his anus clamping down on me. I slowly pushed forward. The device did its job but not to the complete size of my cock. As I slowly travelled inside him, his anus stretched to match the size of my cock. Dylan was still whimpering a bit until I pushed myself in a little further and hit his prostate. It was like he was hit with electricity; he gasped as his eyes grew larger and let out a moan. Oh, yes, this feels good he said. That was all I needed as I pushed myself in until my ball sack was resting on his cheeks. I left my cock inside him for a few seconds to finish stretching him and to prepare for his breeding. I pulled out until my head was at his ring and then pushed back in. As I did Dylan gasped again as I began to kiss him. My tongue made its way past his soft lips as it began to massage his. We kissed as I began to quicken the pace. Dylan's anus had stretched perfectly for my cock to enter him without much resistance now. My hips were rhythmically pounding into him as I began to feel myself nearing climax. I pulled myself up a little to get a free hand on his cock. It was completely hard now as I slid my finger tips up and down his shaft. He started to moan loader when I felt his dick twitch and his anus clench down on my hungry cock once more. I made one more thrust deep inside him and cried out as I felt my cum shoot up my shaft and explode into Dylan. After the last strands of cum were released, I kept my softening cock inside him to enjoy the moment, and to keep my cum inside him so it wouldn't leak out. As my cock retracted it made a slight pop when it exited Dylan's used boy hole. I moved closer to Dylan as he took my cock and licked the remaining cum off of it. I looked back and saw there was some fluid by Dylan's cock. I bent down and licked it up. Dylan asked if that was his cum. I said not entirely, but we can work on that next time. He smiled as we headed to the shower.