Editor's note: This short story is true. It's quite an experiment in finding oneself. The further escalation worried me, but I went along with it. My name is Kevin and I'm learning.
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Driving to the motel, I constantly asked myself if I knew what I was doing. I had accomplished what I set out to do. Sucking cock was a taboo, but exciting; now I could put it to bed. It's not gay, it's a mature sex that allows one to experiment, uninhibited. Sex with a woman is still on the top of my list and I can do a respectable job at satisfying her. But I discovered I'm good at giving head and I enjoy it.
This third visit was unnecessary. I agreed to it only because I had a fun time doing it. Don't get me wrong, anyone would tell me that's bullshit, you just can't get enough cock. Maybe, I don't think too much about it. Even though I learned a lot, I was still new to it and understood it makes me vulnerable. When you give head, make sure you can control the situation.
Honestly, I was worried I might not be able to manage his advances. I had cleaned myself out the last time I met with Troy although nothing happened. I did the same this time. I was afraid if something went down, either consensual or forced, I should at least be clean. I didn't want to be embarrassed. It was not my intension, but I knew I was tempting fate.
I pulled into the parking lot, parked the car, and went up to Troy's room. When the elevator opened, opposite his room, I felt strange and hesitated to knock. I was sure Troy thought of me as some cocksucker that can't stop taking any available dick in his mouth. All this experimental stuff is most likely a load of crap to him. I kept up my wise guy ways to convince him otherwise, but who knows. Part of the fun is being submissive. I understood the fun part but wondered about the attitude of the man I'm submitting too. The feelings get complicated.
I knocked on the door and it opened immediately. Troy stood there in his hotel bathrobe.
"Hey, come in."
"Hi Troy, how is it going," I said trying to sound manly.
"I'll be better after you take care of me," he said with a grin.
"I guess I shouldn't waste time then."
I smiled and walked over to the bed. I casually started to strip while Troy stood nearby watching me. I felt like a striptease. I was down to my shorts and bent over to step out of them; that gave Troy a chance to grab my ass.
"Careful Troy, you know how I feel."
I turned my head to look at him, but he kept feeling me up, paying no attention to what I had just said.
"Damn it Troy, what the hell?"
I was at the foot of the bed, facing the bed where I laid my clothes. I couldn't move easily, as my knees were up against the base board. Troy was relentless and let his hand take full advantage of the situation. He had skillfully, worked his fingers down the crack of my ass and found my anus. That's when I felt his finger trying to enter me.
Troy only partially inserted his finger when I twisted to the left and turned around. Troy lost his hold, and his finger came out of me. I stood there glaring at him, he stood there with a smug smile on his face.
"You knew that wasn't going to happen, why?" I asked pissed.
"Because I like ass, I'd like to fuck yours. I figured if I got my finger in you, you might like it."
I didn't answer him, and he continued, "Kevin, you told me you enjoyed sucking cock to experience the feeling. I assumed you were open to new things, even though you object."
"And getting fucked in the ass is one of those new feelings?" I asked sarcastically.
"Think about it, wouldn't it be exciting to go all the way?"
That is a line I'd use on a girl. What the hell. This guy is trying for a fuck session and not giving up. I stood there naked without any clue as to how to get the night back under control.
Troy dropped his robe on the floor, standing there with a hardon and looking anxious.
"Now that's what I'm here for," I said, "Come on, lay down and I'll get to work on you." I hoped it would take his mind off of other things. If I get him to cum, I'll be able to finish this night.
"Kevin, what are you doing?"
"What, I came here to give you a blowjob."
"Wait a minute, wait," Troy said as he came up close to me.
"Listen, just hear me out. I love how you give head, don't get me wrong, but I would really like a shot at that ass of yours."
"I'm not going to let you fuck me Troy, I told you that from the beginning."
Rubbing his chin, Troy said, "Look, why don't we try something. You haven't gotten off, right? Well, that's not fair is it. Let's do this, we can lay down together and jerk each other off, see how it feels."
"I don't see a problem with that, but why change things. I take care of myself."
Laying down on the bed, Troy said rather softly, "come on, let's do it."
Troy patted the side of bed next to him. I felt weird. I wasn't looking for any other action and laying down with him felt strange, more like a couple then just a quick blow.
"Come on, Kev, trust me."
Cautiously, I laid down next to him, my apprehension showing. My cock wasn't hard when he took hold of it. He, of course, was hard as a rock when I took hold of his. It was easy working his meat. Troy, on the other hand, was trying to get me hard. He would alternate between pulling my dick and massaging my balls.
"Nervous?" He asked.
"No, just unsure," I replied.
I wanted to get into it, so with my free hand I reach for my crotch and met his hand working me. Another guy's hand on my dick was getting me hard. We continued until my dick was erect.
"Feels good?" Troy ask.
"Of course," I blurted out, although I didn't want too; I was on alert.
"Yeah, it does, doesn't it? Just go with it."
We spent the next ten minutes manipulating each other. The more I rubbed his cock, and he rubbed mine, the more I wanted to get to what I came for. I rolled on my side facing him. I moved down over his stomach until his cock was an inch away. This time he didn't object when I slid him into my mouth. He couldn't keep holding my cock, but the last ten minutes had me hard and horny. I sucked him with a passion and found the position comfortable.
Troy didn't stop me, so I kept it up. I didn't pay attention to anything except his dick, and knew when he came this time, it would be best out of three. What I didn't realize was, because I slinked down to his cock, my ass was within easy reach. I was blowing him when I felt his hand feeling me up again.
It brought me back to reality. Releasing his cock, I raised my head and said, "Troy?"
"Relax, "he said, "I'm just playing,"
I wanted to get my ass away from his reach. However, I couldn't move without losing his cock. He twitched a few times, so I had the feeling he would soon bust.
I let him have his way, his hand was all over my rear. I tried to ignore it.
Gradually, his fingers crept closer to my anus. He would approach it and move away before I could react. He was testing me, but I was so horny, a little ass play wasn't going to spoil the moment. His hand came off my backside, but, after a brief time, he returned to his exploring. His fingers traveled up the crack of my ass; they felt cool and wet. In the fog of passion, I didn't immediately register the feeling.
Suddenly with one smooth push, he slipped his finger in me. It went in with such ease, it surprised me. Then I realized, he had spread lube around my asshole. He pinned me and I let him get to first base.
Getting his finger in me got to Troy and his cock started twitching hard; I was sure he would cum, but instead, he pulled me away from his cock and laid me back down next to him. He took hold of my cock again and started to jerk me off. I hoped he would keep it up; I needed to cum.
"Troy, damn it. I need to cum, and I want to suck you off, why did you stop me."
He didn't say anything but kept jerking me to a point that I was ready to bust.
As I was moaning, he started gently rolling me away from him. He didn't stop jerking me, which kept me on the edge. I resisted his efforts, but in the mix of things, I was trembling hot and soon found myself on my stomach, still aching to get off.
He rolled beside me and kept of my dick for a minute more. Then he lifted off the mattress and positioned himself behind me.
"This is not a good idea, Troy, cut it out," I said, my voice trembling.
Now he was ignoring me. I pressed my legs tightly together, causing him to straddle me. I thought it might discourage him, but he liked the view. He massaged my buttock which I had tightened up. His fingers would move down the crack of my ass, exploring deeper with each pass. Despite my clenched ass, his fingers were soon where he wanted them. I applied more effort to keep him out, but I could feel him slowly pushing his finger in me.
I arched my back at the intrusion. He didn't do anything and just held me there for several minutes.
I kept my ass clenched as tight as I could, but he was in me. At some point, I could feel his finger moving and rubbing me inside. The feeling was different than anything I had felt before. It felt so damn good, I didn't stop him and figured I could back out if he tried to nail me. Whatever he was doing, it made my cock feel strange, making it twitch on its own.
The feeling was so intense, I just lay there on my stomach, hoping it wouldn't stop. I felt like I wanted to cum but couldn't explain it. I started to move my hips at the pleasure, a moan escaping me. While Troy increased his internal massage, he worked his legs between mine and was slowly pushing them apart. I didn't care, I didn't want him to stop.
Troy finally said something, "Are you doing, ok?"
"Yeah, I'm fine," is all I said.
By now my legs were apart and I was helpless. What Troy was doing had me captive.
