My Bosses Son
My boss, and close family friend asked me to watch his son overnight while he and his wife went out to spend time with each other. His son was at that age where he gets curious and began asking question. That led to other things…
Now I’m normally not the kind of person who tells people about his sex life, but sometimes something so great happens, you should let everyone know about it. Hell, maybe they can go have that experience to. This story is about my encounter with an underage male, Jake. He was actually the 13 year old son of my boss. I am very close to his family and the little guy always got along with me. One night, my boss and his wife wanted to spend some alone time so they asked if they could drop off Jake at my house for the night. Of course it was fine, we would watch some movies or play some games, or so I thought.
About an hour after Jake’s parents had left, he told me he was learning about sex in school. I tried to change the subject because it made me a little uncomfortable. But, he persisted. He asked me what it was like. I told him the birds and the bee’s story, basically the same way every father tells his son. He asked my how old I was when I first had sex, and what she looked like underneath.
Soon, the conversation turned very personal and he told me about himself. How he liked girls, but always wondered about guys. Trying not to embarrass him, I said every guy has that feeling every once in a while. Then, very surprisingly, he asked me about my dick, how long it was. I told him about seven inches. He told me his was about the same.
Eventually, the talking had gotten me a little excited, and because I was wearing sweat pants and no underwear, he could tell. I saw him glancing down at it and staring for a while, even though I tried to hide it. He then reaches for the remote, which was on my other side from him. He purposely rubbed his chest on my cock just to see what it felt like.
We both got quite for a little while, and I said, you felt it didn’t you. He laughed and admitted to it. He said he did it on purpose, just out of curiosity. He asked it he could see it. Once again trying not to embarrass him, I said maybe some other time. He said, I’ll show you mine. Without giving me a chance to reply, he pulled his shorts and underwear below his dick. It sprung strait up and pointed directly at me. It was really large, a little larger than mine. “Now show me yours” he said.
I said, okay, but it’s very important that this stays between us. He agreed. I pulled my pants below my dick, it was semi-stiff. “Wow, you have a lot of hair” he said. Yeah, you will too soon. He then asked if he could touch it. When he said that, my cock got rock hard and he knew I wanted it. He didn’t wait for an answer, he just grabbed it. I felt his small soft hand wrap around it and I almost lost control. He just held onto it for a while, before getting closer and telling me to grab his. “Teach me how to have sex” he said.
I reach down and grabbed his cock, it was so thick. I began stroking him and he moaned a little with pleasure. I told him; first, he had to suck my dick. He got on his knees on the floor, crawled over between my legs and put the head of my dick in his mouth. I wanted to cum right there, but I held it in. He sucked for a good five minutes before he got tired of it and asked me to suck his.
He sat back on the couch and I assumed position. I put all I could of his cock in my mouth. About thirty seconds of sucking, and without warning, he shot his load deep in my throat. I gagged a little and his young white cream came out of my mouth and all over his bald balls. I thought he would be finished, but I thought wrong. He got up and flipped over and told me to fuck his ass. I was so surprised, this little innocent kid, just asked me to fuck his little ass.
He bent over a pulled his ass cheeks apart. I could see he had never done this before. His ass looked like it had never been touched. It was completely hairless and the hole was so tiny. I thought there was no way I was going to get it in. I leaned forward and licked his ass. He flinched but stayed put. I began licking faster and faster, eventually getting him to loosen up and let my tongue enter. He tasted so great. I felt like a virgin again. I then stuck a finger in and finger fucked him, leading up to two fingers. After I felt like he was loose enough I got up put the tip of my now throbbing dick to his ass hole. I applied a little pressure.
I seen his hands grab the pillow of the couch to help ease the pain, but he said nothing. I got about three inches in before I began to get in rhythm and actually fuck him. I reach down to play with his balls and felt his dick was rock hard again. I fucked for about five minutes before I let myself go. I shot a huge load in his ass. I stayed in him until my dick got soft. When I pulled out, cum followed and flowed over his balls before dripping on the floor.
I knew he would want his turn so I turned around and put my ass in the air. When he turned, he didn’t lick or spit, he put his dick at my entrance and went in fast. It hurt like hell but felt great. I had the large dick of a 13 year old kid in my ass hole. It didn’t take him long either. After about two minutes of fucking, he said “I want to cum in your mouth.” By that time, I didn’t care; I rolled over and opened my mouth. His cum shot all over my face, and into my mouth. It tasted great, I sucked every last drop before swallowing it.
We got up a talked and little and decided it was time to go to bed. He told me he was going to make sure that I was going to watch him whenever he needed a babysitter. That was fine with me. I went to bed and before I got to sleep, he came in my room and asked if he could sleep with me. I told him okay, and well, that’s for another story…