Trying It Again

It's been maybe three years since my first time. I thought I would never get another chance to feel a cock inside me again. I had posted personal ads occasionally over the years in hopes of getting another chance. After enough people disappearing on me or my own lack of courage to go through with it, it seemed that there would never be a second time. I was wrong.

Last week, my parents had gone out of town for the weekend, leaving the house to just me. I hadn't planned on this, but on the last night I had the house before they came back, I found myself posting another ad. I posted late at night at around two in the morning. I was sure no one would respond before I was asleep. However, within minutes I received a message from Teddy, if that was really his name.

He was interested in coming over and fucking me. Usually this would be the point where I would send a few messages back and forth, turning myself on until I jerked off and lost all interest in the matter. However, Teddy didn't want to waste any time. He told me he was 47, an age that really turned me on. I am 23, and the idea of a man more than twice my age having his way with me makes me instantly hard.

I replied to his email as I sat in my chair gently bouncing up and down on the two markers I had in my ass. In my response I told him what we would do. He would drive up, come into the house which was completely dark, fuck me, and leave. After sending the message I grabbed another marker, pushing a third inside of me and stretching myself a bit more.

He answered quickly, agreeing to my terms and asking for my address. My address... Fuck no I wasn't going to give it to him. What if he was just some strange murderer or something? We've all heard stories of murderers that find other people in personal ads. What if he was one? I started to chicken out as usual, getting ready to close my email, but then I stopped. I had the house to myself and probably wouldn't for at least another year. This was my chance...

I typed in my address and then froze to look at it. If I sent it, I couldn't really turn back. I thought about it, hovering over the 'Send' button for a minute. Fuck it. I clicked, sending my address to this complete stranger. I started to regret it, hoping maybe he wouldn't answer. He did though, and told me he was on his way and would be there at three. I looked at the clock on the computer. Twenty minutes was all I had to prepare? Another minute ticked away as I looked.

I started panicking a little, still unsure of my decision. I wasn't ready mentally at all. I stood up from the kitchen island and opened the cabinet above the fridge, pulling out a bottle of Southern Comfort. I filled the glass halfway with ice and to the top with the liquor. I needed to drink as much as I could before he showed up or I would chicken out for sure. My sips turned to gulps when I saw that I only had ten minutes left.

I lubed up another marker and placed it with the others, hoping I could stretch myself more before he showed up. It fit but not without difficulty. I filled my glass again and continued drinking while rubbing my dick, watching the minutes fly by. Six. Five. Four. I saw a light outside and turned out all the lights as my heart raced. I moved to the front of the house and peeked out the window. It wasn't him. After the car drove out of the neighborhood, I opened my front door and left it ajar for when he showed up.

Two minutes left. I removed all of the markers and drank as much as I could of the second glass before I heard a car door shut. I threw a blanket on the floor of the room connected to the kitchen, and hurried to the front room to peer outside. A dark figure was halfway up my driveway and walking quickly towards the house. The idea of shutting the door and locking it flicked through my mind, but I stood there nervous and frozen as he opened the front door and stepped in, closing the door behind him.

"Hey," I said weakly, my voice shaking.

"Hey," he replied in a nervous voice as well.

There was an awkward moment of silence as we stood there facing each other, unable to really make out the features or faces of each other.

"Sorry about the no lights thing, I'm just really shy and nervous," I said embarrassed.

"It's cool... so..," he replied. I turned and walked slowly into the next room which was attached to the kitchen.

"Um... you can sit down if you want," I said, motioning in the dark towards the love seat next to the doorway. Teddy sat down and remained there quietly.

Another awkward moment of silence.

"Sorry, I'm really nervous," I repeated. I sounded like a fucking idiot.

"Well, what do you want to do?" he asked.

"Whatever you want," I answered.

"Well... we could watch some porn to start," he said.

Porn? I've never been a fan of gay porn even with my occasional fantasies. I didn't want to tell him no, but I certainly didn't want to watch any porn. I did the only thing I could think of that would avoid that, which was to drop my shorts and pull off my shirt, standing naked in front of the stranger I had just met. I stepped forward towards him, and he pulled out his dick and began stroking. Teddy reached out and grabbed my hand, pulling me another step forward. He guided my hand to his dick, wrapping my fingers around it. I started stroking slowly, hoping I was pleasing him. I dropped to my knees between his legs, continuing my motions.

"Do you... want me to suck it?" I asked in a soft voice.

"Definitely," he answered, leaning further back.

I wasted no time, sinking my head between his legs and sliding his dick into my mouth. I was pretty sure I give horrible head. In my defense, I had only had one brief opportunity to practice before. My teeth grazed a little the first time I pulled my head back up. I made sure to use only my lips as I moved my head back down. Stroking his cock with my lips, I slid my tongue around it. The taste was neither pleasant nor unpleasant. I attempted to slide his dick deeper into my throat, but I gagged and closed up every time. His moans gave me the impression that he was enjoying it, but I really just wanted him inside of me. I removed the stranger's dick from my mouth.

"Do you want to fuck me?" I asked softly, my voice still shaking.

"What?" he replied.

"Do you want to fuck me?" I repeated a little louder.

"Of course... do you want to go to the bed or...?" he answered.

"We can here," I responded, motioning towards the blanket that I had placed on the floor earlier.

I dropped onto all fours and turned away from him, crawling onto the blanket. I looked back to see him pulling out a condom and quickly placing it over his hard dick. Looking back now I think I am glad he did, but at the time I didn't really want him to use it. I wanted him to cum inside me.

He knelt down behind me and grabbed my hips, pulling me towards him. I arched my back preparing myself for him to fuck me. He fumbled around for a moment, trying to slide himself inside of me. It wasn't going in so easily, so he gave a hard thrust into me. The blanket was a bad idea. There was no friction and I immediately was pushed flat onto the ground.

"Um... maybe we can do it over the couch?" I said embarrassed. He stood up and I followed. Teddy sat back down on the love seat, stroking his cock.

"Come ride me," he told me.

I obeyed and stepped in front of him. I had never found myself in this position before. Bending my knees, I lowered myself down over him. His dick slid straight into my asshole. I bounced on the stranger's lap, stroking his hard cock with my tight ass. He placed his hands on my hips and began moaning.

As I continued my motions up and down his cock, I thought about how I was a slut. I was letting some random old guy use me for his pleasure and I loved it. I started lifting myself further off his dick, only the tip remaining inside, and slamming myself back down on it. His moans grew louder. He thrust up into me every time I lowered back down.

"Are you about to cum?" I asked. I wanted him to shoot his cum on my face or in my mouth.

"I just did...," he replied.

I was disappointed. I slowed my bouncing as I stroked myself until I finished as well. My cum shot out onto the floor while I sat in his lap, his dick still inside me. I started feeling how I always did when I finished. The idea of gay actions changed from a turn on to... not. I couldn't believe what I had just done. I pulled myself up off his dick and stepped away.

Another awkward moment of silence.

He pulled the condom off and asked me where to put it. I took it from him, walked into the kitchen, and threw it into an empty soda box. When I turned back around he was standing.

"So... do you want to do this again sometime?" he asked.

"Maybe... I'll let you know," I replied.

I wasn't sure whether I did or didn't at the time.

He made his way towards the front door and left. I watched out the window until he drove off, looking around to see if any of my neighbors were watching or noticed the strange visitor. I haven't tried contacting him since then, but as I write this I am considering it. Although, if I ever experience another guy again, I hope that he is much more dominant and forceful next time...