Meeting people is easy.

I was 17 at the time, and I was still very much into the chatroom scene on American Online. It had been a year since things started with Jeff. We were still hooking up pretty regularly—mostly in the afternoons after I got home from high school before my mother came home from work. Things between he and I were still very hot, only he wasn’t into anal. He didn’t want to do it to me, and he definitely didn’t want me to do it to him.

It was summer, and I had been left home alone again for another week, and I was pretty bored. Jeff had gone on vacation—so I was left to my own devices: masturbating in gay chatrooms.

I found myself frequenting a m4m room that was for my city. It wasn’t that popular, but I found the occasional guy to talk to. They all liked hearing my stories about Jeff. All the time I spent there I was scouting for the possible prospect of someone to go farther with—for someone to fuck me in the ass.

On a Thursday night, I found myself talking to a married man who had been having a lot of bi-sexual urges as of late. He hadn’t done anything yet, although he told me it had come close a few times. He wanted to try it all: oral, anal, the works. He seemed like the perfect candidate.

As the conversation went on later and later into the night—he told me his wife and kids were asleep. I asked him if he wanted to get together on Friday at some point. He said that his wife was taking his kids on a weekend trip, and after some convincing, he nervously agreed. I told him no pressure. That I’d bring some pornos over, some gay and some straight, and we could start with those, and see if things went anywhere.

He told me to be online in the morning, because he was going to send me a message after his family left. I got up early for teenager with nothing to do during the summer, 7 a.m., and logged on. Around 8:00 he got on, and said his family was on their way out. He told me to come by in an hour—just to make sure that his wife didn’t forget anything, and come back suddenly.

I had an hour to get ready. I got a small bag out, and threw in some good porno tapes, and a bottle of lubricant. I hadn’t gotten dressed yet. I stripped out of my pj’s, and looked at my naked body in the bathroom mirror. I was excited about the prospects that the day had, but I was also nervous. I hoped that this guy didn’t turn out to be a creep or anything.

Before I got dressed, I decided to paint my toenails. I didn’t know if he’d be into that—but it made me feel sexy. After they dried, I put on some boxer briefs, jeans and a t-shirt. Then I was on my way.

He lived on the other side of town—I didn’t really know where it was, but I drove around and then I found it. It was a decent sized house in a pretty nice neighborhood. I grabbed my goodie bag, and I rang the doorbell.

His name was Mike, and he was a little over 40. He hadn’t dressed yet. He was barefoot, wearing baggy pj pants and a tank top under a robe. We shook hands, and he invited me in. I kicked off my shoes and left them by the door, and I set my bag down. We went into the kitchen, and he offered me a cup of coffee. We sat down at the table, and talked a little more about his close encounters. The mostly involved public parks known for their meeting places. He said had a lot of offers, but always backed out

After about a half hour, he asked if I wanted to move into the living room and get one of the pornos out. I asked if he wanted the gay one of the straight one. Gay, he said. To set the mood.”

I hadn’t rewound it from the last time I started watching it, so it started up right with two guys fucking. We sat down on the couch. I slid off my socks to air out my feet. I sat close to him—trying to feel him out to see if things would lead anywhere. The video was getting pretty hot, and I could see a bulge start to form in the crotch of his pants.

“You seem to be enjoying yourself, I said.

“It looks that way.”

I decided it was time. I reached my hand across his lap, and I put my hand on the bulge. It startled him, and I could tell how nervous he was. I carefully opened the button the fly of his pants, and his dick rose out of them. It was a good size, and it was nice and hard. I wrapped my hand around it, and I started to slowly stroke him.

“Relax Mike, I told him. If you want me to stop, I will.”

“No. It feels good. Keep going.”

We shut the porno off so I could concentrate on him. He seemed pleased with how things were going so far. I continued to stroke him for a while, then I decided to take it further.

I brought my head down into his lap, and took it in my mouth. He was surprised—he started to shudder a little. I took him out and asked if it was okay.

“Yeah. It’s great. I’m just amazed I’m going through with this.”

I put my mouth back down on his cock, and proceeded to suck.

With my free hand, I undid the buckle of my jeans, and unzipped them. He helped slide them down off of my waist. My cock was rock hard, and he went right for it—pulling it out of my boxer briefs. He started tugging on it. He had a good grasp on it. I looked up from his dick, and I saw he had a look of surprise on his face. He couldn’t believe he was getting a blow job from a 17 year old, and that he was touching another guy’s dick.

I kept sucking him, and he was really getting into jerking me off. It felt good. I could tell he had a lot of practice stroking himself. I wondered how far we were going to go. We were both still mostly dressed, sitting on his living room couch.

I pulled his cock out of my mouth and I asked him how he was feeling.

“Good. Still a little nervous.”

“That’s okay. Do you want to keep going?”

“Sure.”

“Do you want to go upstairs to the bedroom?”

We climbed the stairs to the bedroom. I took my shirt off, and I had left my pants in the living room. I was totally nude. He slipped his robe of as we walked up the stairs, and he took his tank top off. Then he let his pj bottoms slide down to his ankles.

I remembered to grab the lube, and I set it on the dresser in his bedroom. He hadn’t made the bed yet. We both laid down in it, and we stated to kiss. He took his cock—still rock hard, and rubbed it along my inner thigh. I couldn’t help but touch myself. We made out for about 10 minutes, then he started moving his mouth down my chest and stopped at my cock.

“I want to know what it feels like in my mouth, he said.

He slowly lowered his mouth around my dick. It was warm. He cautiously moved his head up and down on it. For someone who had never sucked a dick before, he was pretty good.

He continued to go down on me, while I took my feet and started to jerk his cock off. I liked the way my painted toenails looked wrapped around his cock. I reached my hand around to my ass, and started to finger my anus a little. I wanted him to fuck me.

He took my dick out of his mouth. It was covered in his spit. He started stroking me again.

“Mike, I started. Do you want to stick it in my ass?”

He seemed surprised.

“Are you sure?”

“Yes. I’ve never taken it in the ass before. And I want you to fuck me.”

“I don’t know

“Please. Grab the lube off the dresser. We’ll go nice and slow.”

He took the lube, and poured it all over my ass. I told him to stick a finger in me first to get me loosened up. Aside from my own fingers, nothing had been in my ass before. I wasn’t 18 yet, so I was sure I’d get carded if I went to an adult book store to try and buy one.

His finger felt good inside me. He dumped some lube on his fingers, and they slid in easily. I told him to fit another in.

“I’m ready to put it in, he said.

“Fuck me, Mike.”

He dumped lube all over his cock, and slathered my asshole with another coating. We were both a sticky, slippery mess. He started going in slowly. I felt my anus spread apart when his head entered me. Then the shaft. It hurt at first. Like a pinching. It felt good though. Like I could deal with the pain.

He started to work it in and out of me. Going slow still. He was enjoying himself. We started talking dirty.

“Do you like the way my dick feels?”

“Uh-huh. I love it. I want you to fuck me all day.”

I started masturbating again while he fucked me. He placed his hands on my hips, and he started to go a little faster, and a little harder. I loved how his dick felt as he was pounding it into me. I could feel my ass slam hard against his pelvis.

I had been jerking off pretty hard. I was close to cumming. I told him, and he told me that he wanted me to cum on my hands and then lick it off. A few more strokes—and I blew my load all over myself. Then I brought my hands up to my mouth and cleaned myself up.

He was a machine. His dick was sliding in and out of me. We had been going at it for what seemed like hours. Finally, he told me he was going to cum. The moment we both had been waiting for. I told him to shoot it in me. He moaned, and then I felt it. He slammed his dick into me one more time, and I felt his jizz shoot into my asshole.

He pulled out, and kept beating off to get the rest of his cum out. I quickly turned around, and put my face right in front of it. Little spurts of jizz flew onto my face and into my mouth. I took him back into my mouth—I tasted my own anus on it. I sucked more out of him. Then he peed a little. He apologized, and tried to excuse himself to go to the bathroom and piss. I told him to keep it coming. He pissed right into my mouth.

After he was finished, we went into the shower and cleaned up. We were both still covered in cum, lube and other various fluids. Cum was dripping out of my ass.

When we were cleaned up, we put some clothes back on. He found his pj pants, and I found my underwear. We went back down to the living room and put the porno back on, and started to fool around a little again.

“So, I asked him. Was it everything you hoped for?”

“Yeah. It was. Thanks for coming over.”

“Thank you for fucking me. When is your wife coming back?”

“Sunday night.”

“Are you busy for the rest of today?”

“Not at all.”

I ended up staying Friday night, and then left on Saturday afternoon. We fooled around on the couch Friday afternoon, then at night we fucked again. We went into the chatroom together, and told everyone what we had done. They were jealous. So was Jeff, when I told him what I had done while he was away. He told me that I had been a bad boy, and that I deserved a spanking.

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