First Times Are the Best

I had recently given my first blowjob to another guy. A few days went by of me playing the whole thing in my head, fantasizing about it going further. I kept fantasizing about the feel of his dick in my hand, and then the taste of it in my mouth. I wanted him to know how much I cherished that taste. I knew he knew my phone number, but I didn't know to call him or wait for him or what.

As the weekend approached, I got a text message from him that made my heart race. It said, "Hey boy. You ready to come over today?"

I responded, "Sure. What time?"

"Any time after 6." I felt that same nervousness I did the first time, but this time I was full of eager anticipation having a good idea of what to expect.

I had plenty of time to get ready, but of course it was hard to contain myself. I went straight into the bathroom. I figured I must've looked alright last time for him to call me again. So I wouldn't deviate from that routine much, if at all. I hopped into the shower. My face and legs were pretty smooth, but I decided I better shave everything again just to be as smooth as possible for him. My face, legs, and most especially the area between my legs, I made sure were exceptionally smooth. I put on the one pair of panties I had, and used two mirrors so I could see how feminine I looked from behind with them. After being satisfied with that I put on a tee shirt and some jeans. I felt like it wasn't the right thing to wear, though I wore something similar the first time I saw him. There was no 'right' thing to wear for something like this.

I got into my car. This time I knew where to go and headed straight there. I knocked, and he discretely let me in. He had a tee shirt on and some boxers. He said, "looking good."

"Thanks."

"So you like it? I mean obviously if you're coming back for more," he said.

"Definitely, I wish I had that experience sooner." I felt shy around him, but I was still able to open up to him that much.

"Good. Do you think you're ready for anal?" he asked.

"I guess. I've been fantasizing about it a lot."

"Lets get started." He pointed between his legs as that was my cue. I kneeled there between his legs. I pushed them apart slightly. He grabbed his dick and pulled it out of his boxers. I moved my head towards it and licked the tip. He grabbed the head and held it upwards, so I licked up and down his shaft. When He released his dick from his hand, I immediately put my head on the head. I grabbed it from the base and started bobbing my head on it. I felt much more comfortable with it than the first time.

His moaning became louder and more frequent. He lifted my head up and pulled me into his bedroom. He started pulling his clothes off, so I did as well. We faced each other. He put his hands on my ass, and slid a finger up and down the middle. Once it reached the center, he circled my hole with it. He asked, "are you sure about this?"

"Definitely."

"It will hurt a little, especially in the beginning."

"That's all right," I said.

He grabbed a towel and placed it on his bed. I stood there watching him, until he told me "lay down on your back on it." I laid there, right on the edge. I lifted my legs into the air as I saw him move his head to my ass. I felt the wetness of his tongue on my ass. He moved it around the center but swirled it closer and closer. It helped ease the tension out of me. The tongue provoked a lot of sensations in me, but ultimately it was a tease.

He stood back up, and I watched him put on a condom. "You ready?" he asked.

"Sure," I said as I grabbed my legs tighter. My ass was at the edge of the bed in anticipation. I watched him grab a bottle of something, I assume was lube, and he rubbed it on his dick.

He moved so that he was facing towards me now. He leaned in, with his dick in his hand, and I could now feel it stabbing me. At first it was some pokes in vain, giving a little sharp pain. I tried to relax myself now, putting my trust in him. I felt it enter finally. I moved myself closer to the edge as I wanted all of it in me. It slowly went deeper until I felt his body pressing against mine. He pulled it out halfway, slowly, and went back all the way in me. This happened several more times, progressively faster. After a minute or so it was at full speed. I was hungry for it, and getting it was everything I was craving. He thrusted in me harder and harder. He leaned over on top of me and kissed my neck.

My legs were over his shoulders. For a moment I became aware of how glad I should be to be flexible enough for that. I put my hands on his ass to pull him closer in the closest point of each thrust. Sometimes he would slow down for a minute and then speed up again.

After some time, which I have no idea how long it had been, he started going much faster and harder. I was moaning with all the thrusts.

"I'm going to cum," he said.

I thought if there was something I'm supposed to do at that point. But ultimately I let him continue while trying to pull my legs closer to me. I felt a warmth through the condom. First it was one big burst of warmth, and then several smaller bursts of warmth after another. It wasn't quite as it was when I had swallowed, but I did feel a certain honor in him having his way with my ass.

He pulled it out slowly. It popped out like a cork from a wine bottle, it fit so well. He asked, "how was it?"

"Great," I said, as I watched him leave to throw away the condom in the bathroom. For a second I thought to myself of asking for the condom, so that I could swallow the cum from it. But it was just a fleeting thought, or at least I chickened out not wanting to appear 'too kinky' with all this being still new to me. When he came back from the bathroom though, I grabbed his dick and licked what cum remained smeared all over it.

"I see that," he said.

I left glowing that night. I know I didn't get off, and I often wondered if I'm only interested in being the bottom then when will I get off? But I was content. I had no desire to get off by cumming. Having a man's dick inside me, penetrating me, got me off. Having a man shoot his sperm while inside me got me off.