Tommy's First Time

My pulse raced as I typed the words out on the screen in front of me. "Would you like to meet up?" I stared at them not knowing whether to hit enter or backspace. I'd only been trying online dating for a month and though Cody and I had been chatting the entire time, I hadn't actually met anyone in person. Sure we had chatted on skype a few times, I had seen his face, I knew that he existed. Hell I had even seen him without a shirt during one of our skype sessions. Still I was nervous.

I closed my eyes. My teacher always says we regret the things we don't do, not the things we do. "Fuck it." I thought to my self and slapped the enter key, sending my message across to Cody.

Cody was 20 and a very hot looking guy. Six foot tall with a swimmers build and a smooth body. Also he was a great guy. Very funny and never once pressured me into meeting up. He knew I had never been with a guy before. That wasn't exactly true, I had given a few head jobs at school but never truly been with another guy if you know what I mean.

Me, I was 18 and straight out of school. 5 foot 8 and very slim. I wanted big muscles but have never been able to develop them. I also wanted to start acting on my sexual urges. I wanted to experience and explore. I was way too nervous to go any gay bars alone, so the internet was where I went.

Cody replied. "Sure." I felt a wave of relief wash over me. "There's a bar on 12th, Shorty's. Let's meet there at 8. My parents have gone away too, so we can go back to mine later if you like. No pressure."

"Awesome! See you there."

"Can't wait to finally meet your cute ass." he added.

I was so excited. Finally I was going to be able to act on my urges. I was 18 and essentially a virgin. I craved having Cody fuck me. That was all I wanted when I thought of being with him, or any man I liked. I don't know why, but I just knew I was a bottom. I had never been with a man before, but I knew that when it happened, it would be me giving my ass to him and not the other way around.

I arrived at the bar a few minutes early, hoping to have a quick drink to calm my nerves before Cody arrived. Shorty's is now the first gay bar I've even been to. It looks just like any other bar really. The place was almost empty. Just me sitting alone and on the opposite wall, three men sitting at a table drinking bourbon. I drank my wine in big sips, hoping it would take effect before he arrived. A man on the other table stared in confusion as I finished my drink in only a few minutes. I glanced at my watch, 8:05. Where was he? Has he stood me up? Surely not. I mean, everyone is politely 15 minutes late anyway. As the first drink began to take effect, I ordered another wine while I waited.

The same man on the other table kept glancing over at me in between the laughs of whatever story the others were talking about. Three of them all looked in their 50s. Two balding, stocky looking guys with their backs to me and the slim grey haired man who kept glancing over.

Oh shit. We just made eye contact and he smiled right at me. I immediately looked away nervously. Where the fuck was Cody? I checked my phone. It was now 8:30. He was properly late. "Hey I'm here. Where are you?" I texted to him. I looked back at the grey haired man. He was back in conversation with the other two. He reminded me a bit of my neighbour Carl. He would mow his lawn without a shirt and I would look at him through the window, perving on his muscled hairy chest. He was the first man I ever had a crush on. Unfortunately he moved away last month, after living next door for less than a year.

More and more people started coming in, but none of them Cody. The place was really starting to fill up now and people were taking the empty chairs from my table. Still no reply from Cody. The three men all stood up laughing and shook hands with each other. The two stocky men walking out together. The grey haired man looked at his phone briefly before looking over at me again. I looked away.

"Is this seat taken?"

It was the grey haired man. Oh no, he wanted to talk! What do I do?

"Oh um, I'm waiting for someone." I stammered.

He laughed. "You've been waiting over an hour now. If he was coming, he would be here by now."

He was right. Cody was a no show. "Come on, I'll buy you another glass of wine." he said as he sat down.

"So tell me, this guy who stood you up, where you meet him?"

"Online." I murmured.

"This your first meeting?"

"Yeah." I sighed.

He laughed again. "Chin up son, there's loads of fakes online. Hell, half the boys I arrange to meet never show up either. Don't worry about it. You're a good looking kid."

"Thanks man."

"Look around, every man here would give his left nut to take a boy like you home for a night."

I let out half a laugh. He was trying to cheer me up and was doing alright.

Our drinks arrived and he handed one to me. "Cheers." he said as we clinked glasses. "I'm Rob by the way."

"I'm Tommy."

"Pleasure to meet you Tommy." he grinned as he extended his hand to shake. "I hope you don't mind my checking out your handsome face from over there before?"

"That's ok." I said as I took a sip. Looking at Rob, it was obvious he took care of him self. He was slim but fairly defined. I could see the vein in his bicep as he raised his glass. He must work out. His grey hair was accompanied by a brown beard. Very short, almost like stubble. He was quite a handsome man, just a lot older than the one I was intending to meet.

"So tell me Tommy, what brings you here tonight?"

I explained that I was meant to be meeting Cody and I was my first time in a gay bar. In fact it was my first time meeting another guy and that's why I was so nervous. He said he understood and that it was like that for him too when he was young, but that it got easier with experience. I told him that the only experience I had was a few blow jobs in school and he laughed. "You have a lot ahead you. All that will change." he laughed.

The three glasses of wine had made me quite tipsy, which must be why I was able to spill everything to Rob. He was really understanding and I was beginning to feel quite attracted to him. We had another drink and by then the DJ had started playing. It was now very loud and almost impossible to hear. Rob leaned over the table, almost having to shout over the music "What do you say we finish these and go somewhere more quiet?" he yelled.

I nodded and finished my glass in a big mouthful.

We walked outside to a nice summer night. It was late, but still warm. We walked along the river as Rob told me how he was surprised to see me tonight because not many twinks go to that bar anymore and how it's mostly dads and bears.

"It's kind of lucky you got stood up tonight Tommy. Otherwise I wouldn't have met you." He said as he put his arm around my shoulder while we walked.

"I like you Rob." I said as I also put my arm around his waist. "Do you like me?"

"I sure do Tommy. That's why I've got a proposition for you."

"What's that?" I asked, as a nervous excitement rushed over me. Am I about to have my first experience with a man? A real man?

"I know you want experience. You don't like that Cody kid for who he is, you just wanted to experiment with someone didn't you?"

"I guess so. Yeah."

"I have loads of experience. Come back to my place and I will give you what you need."

"What do you mean?" I asked. I was pretty sure I knew.

He lowered his arm from my shoulder, placing it on my butt and giving it a squeeze."You know what you want Tommy. You didn't want Cody, you wanted a cock. I'm a total top, no cock has ever been near my ass and none ever will. But I've spread more asses and mouths than you'll ever know. And I know a bottom when I see one. You're a total bottom boy. When you get naked with a man, you know your job is to get on the end of his cock. Am I right?"

I didn't say anything. I didn't need to. He was absolutely right and he knew it. Whenever I pictured myself with another guy, I was always the bottom. Always working to satisfy the other guy.

"So Tommy, that's why we are going back to my place where I'll be the first man to mount this cute ass" he said as he squeezed my butt, "and you can experience what it feels like to have a real cock throbbing inside you."

I didn't know what to say.

"If you don't enjoy it, just say so and we can stop. But I think your cock is doing the talking for you." He laughed, pointing at the hard bulge that had appeared in my jeans. "I think before long, you will be begging for it. It's just around the corner here."

Rob lived in a second floor apartment overlooking the river. I didn't get much time to take in the view however as the second the door shut behind us he had me pinned against the wall as he laid a big kiss on me.

"Fuck you're a hot boy" he said as he pulled his shirt over his head, revealing his defined pecs covered in a layer of thick chest hair. Next he unbuttoned his pants and dropped them to the floor, freeing his 7 inch cut cock which was already standing a full, thick erection, veins bulging. "Normally I would start you sucking for half an hour but the thought of busting your cherry makes me want to go straight into it."

He pulled my shirt over my head as I pulled down my pants, until both of us stood there naked, facing eachother. He led me over to a dark timber dining table, "Here, bend over." he said as he grabbed me by the shoulders and turned me around. Nervously I stood facing the table, placed my hands on it and leaned over. It was so thick! Would it fit?

"All the way over." he ordered, pushing me down until my chest was firmly against the cold surface of the table. My chin was pressed into the table and I couldn't turn to see behind me, but I felt his big hands spread my ass cheeks and waited nervously for what was about to come. Unexpectedly, his face plunged into my ass and he thrust his tongue into my hole. Shocked, I let out a gasp of pleasure as my eyes began to roll back. I had never experienced anything like this before, as he worked at my tight hole with his tongue. My hole twitched as his wet tongue worked its way inside.

"You like that boy don't you? I think we better loosen you up before your first cock."

Next he slipped his finger tip inside me. Slowly he worked it deeper inside as his tongue continually lapped at my ass. Then a second slipped in. The feeling was intense. Never before had another guy played with me like this. The feeling of nervousness I had before had been replaced with a craving. No longer was I scared of being fucked, I wanted it, I needed it right now.

Rob pulled his two fingers away and removed his mouth from around my ass. "I think you're ready now boy. Do you want it?"

"Yes."

"That's not begging for it. Do you want it or not?" said Rob.

"Please. I want it now." I stammered.

"Then beg. How much do you want it? Beg for daddy's cock to fuck you."

"Please fuck me. Fuck me daddy, I need it."

"That's my boy." he chuckled. With that he positioned his cock against my virgin hole and began to push. Almost immediately his thick cock started to force its way inside. "You are one tight little slut. Even after all that rimming" he said as he pushed further inside me. "Don't fight it boy, I'm coming in, just breathe deeply. Relax and let me inside. Let me fill you up."

The pain was not as bad as I had feared. It was almost as if my ass knew to let him in. Finally I felt the base of his cock push against me and I knew he was fully inside. Almost immediately the pain subsided. With his cock firmly buried in my tight ass he leaned forward and whispered into my ear, "I knew the moment I saw you tonight that I was going to bring you back here and fuck your brains out. How does it feel to have your first daddy cock breeding your ass?"

"It feels good." was all I could moan, my hole stretched around his slippery cock.

He pushed one had between my shoulders, pressing me into the table and placed the other on my hips. With that he began to thrust. Slowly at first, but gradually increasing in speed. Each thrust pushed me forward and rubbed my own cock which was pressed between me and the table. I could hear Rob moan and grunt with each thrust. The thought of another man using me for sexual pleasure made it even more intense.

The thrusts go faster and harder and the moans got louder and louder. His hips were now slamming into me which each thrust. He gripped my hip harder, almost digging his nails into me. I could tell he was about to cum. Finally he let out one loud moan before ramming to cock in one last time and staying there, trying to bury it as deep as he could as his sweaty body collapsed on top of me, his balls emptying their load inside.

"That was pretty intense." He said as he regained his breath. "But you still have much more to learn about serving your man." He stood up and his softening cock slipped from my ass, leaving me feeling very empty. I stood up too and noticed a pool of cum on the table where my stomach had been. So intense was the fucking that I had cum without touching my cock.

"I get home from work at 6pm. From now until the end of summer, you will meet me here every night at exactly 6pm. You will suck my cock or give me more ass until I am satisfied. Only then can you call your self a bottom. Do you understand?"

"I will be there." I said as the excitement washed over me again.

I began to get dressed and Rob interrupted. "Where a you going?"

"Home?" I queried, thinking we were finished.

"Oh no you're not. I'm not done with you yet. We're gonna clean up in the shower and then I'm gonna see if that little mouth is as good as your tight ass." He grinned as he took my arm and led me off to the bathroom.

This was going to be a good summer.