Babysitting Discovery Part 5 By Mitchell Knight Christmas was fast approaching, and I was looking forward to it this time of the year for different reasons than I usually did. Sure the presents and the good cheer that came with the holiday were nice, but this year I was really looking forward to it because of all the parties that the Wallace's would be going to. This would get me over to their house a lot in the next few weeks, and hopefully Steve would make good on his promise and we would get together again soon, so he could show me everything he had hinted about. At first I thought my dreams of this season were crushed when my mother started talking at dinner one night about the Wallace's. "I talked to Tami today," my mom was saying to my dad, "and you'll never guess what they're doing for Christmas." "What?" he asked. "They're going to Florida for the week that Nick has off of school," my mom answered. 'Oh no!' I thought. "Doesn't that sound like fun?" she asked. "Yes it does. I'm sure it will be a nice change for them to be some place warm for Christmas." "She also asked me something that you and I will have to talk about," my mom continued. "What's that?" he asked. "She asked if Alex could go along and watch Nick for the week," she answered. 'Florida? With Steve? For a week?' "Oh, mom, can I?" I pleaded. "Please let me go." "No fair," my little sister protested. "Why does he get to go to Florida? I want to go too." "That would be nice," my dad commented. "Can I go, Dad? Please," I asked. "We have been invited to go along. They're staying in a house some friends of theirs own. Their friends are going to be out of town for that week visiting relatives." my mom added. "Really? Hmm...why don't we all go then?" he suggested. "Yah!" my sister cheered. "Disneyworld!" I breathed an internal sigh of relief. Christmas was going to turn out even better than I had thought. The week before we left seemed to go quickly since we were involved in preparations for the trip. I also found that being able to spend a whole week with Steve was much better than just one night, and I could wait for something like that. We all loaded into our van on the day of our flight and headed for the airport. The airplane ride was kind of fun since I'd only been on an airplane once before when I was very young. When we landed in Florida we were all quite glad we had come to this state of warmth and sunshine. Our families picked up our rental cars, packed them up, and drove out to the house. It was a beautiful, large house on the beach. We unpacked and then went out to the beach to relax. That night we went out to eat. The next morning I slept in. When I woke up I went into Nick's room which was connected to mine by a bathroom. His bed was empty. I looked out his window and could see that they were all out on the beach. I returned to our bathroom, slipped out of my boxer shorts, and stepped into the shower. As I was washing my crotch, I started to tease myself. I had worked my cock into an erection when Steve suddenly stuck his head in, nearly scaring the shit out of me. "Hurry up and meet me in your room," he said. Then he pulled the curtain closed. Like I was going to keep him waiting! I shut off the water and quickly dried off, my excitement distracting me from drying off very well. Water droplets still spotted my body, but I wrapped the towel around my waist, not caring. In my room, Steve lay on the bed completely naked with his swollen erection in his hand. To my eyes it seemed shiny. On the nightstand was an open jar of Vaseline. 'Did he put that on it?' I wondered. Dropping the towel, I crawled into bed with him. "I want you to fuck me," he whispered in my ear. "Huh?" I asked. "This is something only a guy can do for me," Steve said. "Bring that nice dick of yours over here." I scooted up closer to the head of the bed. He dipped his fingers into the Vaseline and spread this over my dick. The butterflies started up in my stomach as I wondered what he was up to. Once my penis was fully covered in it, Steve turned over onto his hands and knees. He dipped his fingers into the jar again and spread it generously over his anus. I watched as he slid one and then two fingers into his hole. "You're going to stick this," he said, stroking my cock, "into here." He pushed a finger into his hole again. "Put it in there?" I asked, shocked. "Yes." "Won't it hurt?" I asked. I'd gotten used to a finger, but something like a cock would surely hurt. "No, it'll feel really good. Especially one your size. Trust me," Steve soothed. "Okay." I knelt behind him, putting my hands on his waist and lining up my cock with his hole. "Go slow. I'll tell you what to do," he said. I pressed the head of my erection against the outside of his anus. I pushed forward gently, but my penis slipped down between his legs in front. His hand grabbed my dick and guided it back to his anus. He put the head just inside him. "Now push forward slowly," he ordered, removing his hand. I followed this instruction, inserting my erection bit by bit into him. It was so tight and hot inside. It felt great against my erection. Once I was completely in, his muscles squeezed me a couple times in greeting. "Okay, just hold it there. How does it feel?" "Oh, it's great," I answered. "It feels good from this end too. Now, slowly pull out, but not all the way. Then push in again. Keep doing this slowly, but then go faster when it feels right." I withdrew until just the head rested inside him. Then I plunged back in him. I realized as I continued this pumping action that this might be what it feels like to fuck a girl. When my orgasm began to build, I pumped him harder and faster. The pressure in my groin grew as I continued. I slipped out at one point when I became a little too eager, but I quickly pushed back in without any trouble and regained my momentum. Beneath me Steve was grunting and moaning at each of my thrusts. He even started shoving his butt back into my pelvis to meet my thrusts. This physical exertion caused me to sweat and I started breathing heavily as I thrust faster and faster. Just as I was about to come anyway, I felt tiny muscle contractions within his anus. These caused me to climax. I let out a loud groan and fell forward onto his back as I spurted forcefully in his ass. I lay there for a while unable to move, my slick chest against his sweaty back, and my cock still buried inside him. When I regained some strength, I pulled out and wondered where all that cum had gone. I wondered if it would just stay inside or if it fell out. "I better get going," Steve said, getting up off the bed. "Aren't you going to do that to me?" I asked. Steve smiled. "No, I think I'm just a little too big for someone your size. It would probably hurt if I stuck this thing in you." "Oh. But you didn't come. Don't--" "Yes I did," Steve said, pointing to the bed. Thick white tiny pools of semen covered the sheets. Those muscle contractions I felt in his anus must have been his climax. "It felt really good, Alex. We'll definitely have to do that again." "Okay." "They're probably missing me. Can you clean that up?" he asked. "Sure," I answered. "Thanks." He pulled on his swim trunks. He gave me a quick, but passionate, kiss before he left. I jumped on the bed in sheer joy and rolled around in his semen. I got up and went to take another shower. End Part 5 .