My New Neighbor Ch. 02

I did as instructed and slowly felt the head of the life-like dildo stretch my hole wider than my fingers had. It had been a while since I had had anything more than my fingers up there and again nothing this size before so the stretch was initially painful. I sharply inhaled at the intrusion.

"Go slow. If it's painful, either stop and wait or pull up a bit," he said sounding genuinely concerned.

"That's it, Parker," he said encouragingly as I was able to slide down past the head. I inched my way down only taking a couple of inches every so often while barely bobbing up and down. Eventually, my ass rested on the windowsill below.

"Excellent. You've got me close, kid. How do you feel?" he asked.

"Full," I replied. "I feel very full. The pressure inside of me is making me lightheaded. May I stroke myself, sir?" I asked, trying hard not to sound like I was begging even though I was absolutely begging in my own head.

"Not yet," he said. "Do one more thing for me. Pull up and allow the dildo to almost pop out of your ass but keep the tip inside. Then, when I say so, sink back down completely as fast as you're able to."

My legs felt a little sore as I stood up slowly, allowing the tip of the dildo to just rest inside of me. I stood there for a few moments with my hands opening my ass wide, showing him I was compliant and obedient. I wanted to please him. And I wanted him to let me get off. My legs started to shake slightly as I waited. Finally, he spoke.

"I want you to picture yourself straddled over my naked body," he said. "My cock head has just gotten through the resistance of your tight hole. I'm supporting your beautiful ass with my large hands and you know I'm about to release you. Your legs are so weak that you know you won't be able to resist it. You take a deep breath to relax your ring, and then it happens. You suddenly drop down and take all of my thick pole at once."

I was so into the story, my cock leaking a continuous stream of precum, that I just relaxed my quads and quickly took the dildo to the hilt, imagining myself sitting onto James' fat dick. The force of the tip of the dildo ramming into my prostate sent an electric sensation throughout my entire body and I lost it. I moaned and groaned loudly, making incomprehensible noises as my cock fired off countless shots of cum all over the chair in front of me. My hands had been on either side of me on the windowsill. Nothing had touched my dick to set it off.

I slowly came down from my high and returned to my senses. I wasn't sure if he had seen what had happened but I would have been surprised if he didn't hear it. I was instantly worried I would be in trouble for cumming without his explicit permission even though it was his story and his instructions that made it happen. I sat down on the windowsill, my ass filled completely, waiting to hear from James.

"Wow, kid. You truly have a magnificent ass. It sounds like you really enjoyed having that whole thing slide up your ass at once, didn't you?" he said.

"I'm so sorry, sir. I don't know what happened. That has never happened to me before," I said with a sense of worry in my voice that I'm sure he could detect.

I could hear him laughing quietly through the phone. "You can't control what you can't control. I saw your hands the whole time. I know you didn't cheat," he said much to my relief. "Then again, I didn't say that you could cum yet. And I haven't even finished yet."

"I'm really sorry, sir," I said while looking over my shoulder into the darkness of the room across the way, the dildo still buried completely inside of me. "What can I do to make it up to you?"

"Why don't you keep bouncing that sexy ass up and down for me?" he said as the familiar sound of him stroking resumed. "But this time, put the dildo on the chair and ride it while facing your bed."

By this point, my orgasm had subsided but I didn't feel completely drained. The constant pressure on my prostate kept me amped up. I slowly stood and the dildo began to emerge from my ass. Once the tip was at my entrance I braced myself slightly and stood up the rest of the way, the dildo making an audible 'pop' as it came all the way out. The sense of emptiness it left felt almost wrong, unbearable in a way. I reached for the dildo, drenched in lube, and moved it to the chair. With me facing my bed, my left side was facing James.

I didn't wait for any additional instructions and slowly sank back down onto the dildo. The familiar stretch and feeling of fullness warmed my body. I quickly began riding this thick pole, getting into a good rhythm. I wanted to give him a good show and get him off.

"So fucking hot," James said as he watched me ravage myself with this dildo. "You can stroke yourself too but only with your right hand," he said.

I looked down and realized that I had never gone soft. My dick was as hard as ever, leaking precum again albeit less than before. I quickly took hold of my dick, making sure it was with my right hand and began slowly stroking, timing it with my thrusts down onto the dildo. I realized now that by using my right hand, James' view was unobstructed. He could see my pert ass swallowing up the dildo he bought for me while he could also watch my hand slowly move up and down my rock-hard dick.

"That's it, kid, ride that cock," he said, his voice a little more strained than before. "Milk my cock with that tight ass. Yeah...you're going to make me cum, boy."

The thought again of me riding him instead of this dildo quickly sent me over the edge and my second orgasm built to the point of no return before I had the chance to stop it. I yelled, "Oh fuck, James! I'm cumming" as my entire body spasmed and my dick began pouring cum. It didn't shoot out like the first time but just oozed out over my hand and shaft creating a sticky, slimy mess.

The movement of my hips slowed to a stop as my orgasmic wave subsided. I again felt guilty cumming without him telling me but it all happened so fast and I lost control. I waited to be spoken to before I would apologize.

"Wow man, that was an incredible show," he said exhaling deeply. "I should be mad that you came again without my permission but the sight of you bouncing up and down on that pole, unable to stop your second orgasm, made me just shoot a huge load. And lucky for you, I beat you to it this time."

"I apologize," I said sincerely. "I guess I just need more training to learn control like you, sir."

"Well, I look forward to teaching you. You have a lot more to learn," he said. "Now, go get cleaned up and get some sleep. Turn the bathroom light on for me while you shower. Don't forget to clean out that hole."

I slowly stood up, the dildo again making a 'pop' sound as it exited my hole. As I was making my way to the shower my phone pinged. I opened it to see a photo of James' face, smiling with a glob of cum across the bridge of his nose and another across his chin going down to the top of his neck. The picture was captioned, "Almost made me hit my eyes, buddy."

I smiled so widely that I almost felt stupid. It felt so good to get this guy off and I couldn't wait for more. I flipped on the bathroom light, turned on the shower, and stepped under the warm water. It soothed my aching muscles, and my legs especially from the run earlier today and the dildo riding I had just done. I soaped up my head and body then moved to my ass. I planted my feet with my ass facing the window and James' apartment, reached back, and spread my ass cheeks while I slowly traced soap around the hole. Every once in a while I would slide a soapy finger in making me moan slightly. I wondered if he was enjoying the show.

Once I was sufficiently clean, I dried off and climbed into bed. My dick was limp and spent from the day and my ass was a little sore but I was satisfied. I quickly looked back at the pictures of James' impressive member before drifting off to sleep, hoping the subliminal messaging would make my mind create a sexy dream with him.

Chapter 3 coming soon.