Date: Mon, 14 May 2018 06:26:07 +0000 (UTC) From: John Schmidt Subject: My Time with Mark The following took place around three years ago. I had come home for winter break during my last year of college. My brother had just moved in with his fiancee and her three children. During the break I frequently had to babysit one or more of her kids, though I didn't mind. One evening I was left alone overnight with her oldest son, the cutest nine-year old ever, named Mark. As usual, it was my duty to make dinner for us and make sure he changed out of his soccer clothes and took his shower afterward. After his shower, he came out of the bathroom in just a pair short of boxers. This was common in his family, both his siblings had this habit too, but I was not raised to walk around in undies as a kid so I was intrigued. I asked him why he and his siblings did this and he told me he didn't know, his family just didn't care. I thought to ask him if he would be ok if I were in my underwear and he said of course. I was excited to now let someone see me in my undies, so took off my shirt and shorts and showed off my tighty whities to him. We sat around in our undies for an hour or so watching tv when I couldn't help to become aroused. I talked him into wrestling around on the bed and, after quickly pinning him a couple times, allowed him to pin me with my face up. He noticed the erection I was hiding under my briefs after a few minutes and asked me what it was. I had just been hiding the remote control from him a few minutes before so I told him it was the remote. He believed me at first but found the remote right after I said that and asked again. I finally told him it was my erect penis, that that's what happens to adults. He said he didn't believe me so I asked if I could show him. When he agreed I pulled my undies down to reveal my six inch rock hard cock, now dripping with precum. He asked about the precum, thinking it was pee. After explaining what it was it I started to jack off in front of him and asked if he wanted to do the same. He slipped off his boxers, let them drop to the floor, and proudly showed his body to me. He was very skinny and had a perfectly smooth body. His penis had not yet grown and was only an inch or two hard. Before I knew it I had reached out and grabbed it with my hand and started rubbing it while jacking off. I moved my dick to his, rubbed our tips together, and covered his dick with my precum. He kept giggling throughout our jacking, so I asked if he wanted to try more. When he nodded yes, I turned him around and rubbed my dick between his perky little butt cheeks. Though I had been with guys before I was never this aroused and couldn't resist him. I grabbed a small bottle of lube from my bag, rubbed some on me and his butt, and started rubbing my dick into him as I tickled him. It didn't take long for my dick to find its way inside him. He let out a loud gasp of surprise but otherwise continued touching and playing with himself. I slowly worked deeper inside him then hugged him for a minute before slowly pulling out. I began pushing gently in and out of him, his small body clenching around my cock as I thrusted. As I humped him a bright light filled my head and I felt as if I were in heaven. I had never been that happy before and couldn't believe my luck and how attractive he was. I had nearly finished after just a minute or two of this, so paused and asked him to turn over to face me. We resumed our activity and while kissing him and rubbing his penis with my hand I lost control and ejaculated inside of him. I couldn't help but stare into his beautiful little blue eyes as I unloaded several heavy shots of cum inside him. A strange sense of dread/guilt and worry washed over me right after I came due to the deed I had done. After a minute of almost panic while still inside him I realized how much we both enjoyed it and how great the experience had been. I slowly pulled out of him and we both put our underwear back on. We sat and talked for a while about what we had done before the conversation turned back to tv. After a bit, he stood up suddenly with a concerned look on his face. I looked over to realize that I hadn't told him to use the bathroom and my semen and the lube I used had just leaked out into his boxers. His boxers, which were short and light blue, had a dark stain on them and a fluid was visible slowly dripping down his leg. I told him to take a quick shower and put fresh boxers. As he showered, I stayed hard and grabbed his dirty undies and continued jacking off until I had another small orgasm accompanied by a small amount of cum shot onto his boxers. Once he finished his shower he joined me on the bed again where we snuggled in our undies til we fell asleep. As the morning broke we were woken up by the sound of his mom and siblings returning home. I quickly reminded him to keep our secret and sent him to his bedroom so I could meet the others downstairs. By that point however it was too late and his mother saw him leave my room in just his boxers. She walked by my room before I could find my shorts and saw me in my briefs but she didn't say anything and I was left to only wonder if she connected those dots. I was consoled by the fact that he and his brother and sister were allowed to wear underwear around the house and so maybe it wasn't odd to see him leave my room that way. Later that day, however, she confronted me on this and asked why he was in my room. I told her he had just come in in the morning. She looked confused and told me she already asked Mark about it and he admitted to sleeping in my room. Caught off guard, I started to stutter and told her he must have come in in the middle of the night. She seemed to accept that answer and told me he slept in the bed with her sometimes too. She left the room then, thankfully not noticing his semen-stained undies just underneath my bed.