Once In a Lifetime

Once again, I found myself on-line looking at porn and drinking beers on a Friday night. After a few hours I moved to the AOL m4m chat rooms. At first I was just looking for some hot chat, but eventually my motivation was to find someone to fuck me for the first time. I had thought about it off and on, chatted about it and even done some on-line role playing, but it was tonight I decided I was going to try and experience in real life. I had a seven inch rubber dong I had been using on myself, so I kind of knew what it was like but I wanted to feel it for real.

I started by chatting in the rooms, checking out profile and putting it out there in the room. I had a couple of responses, but one guy stood out to me so I decided to private message him. His screen name was RunBod2 and it turns out he lived about fifteen away from me.

"Hey, my name is Tim."

"My name is Greg."

"So I was looking to try bottoming for the first time tonight and I saw on your profile that you are a top."

"Yeah, total top."

"I have had some practice with a couple of rubber dongs. The biggest is seven inches."

"Nice, I'm not much bigger. I'm eight inches, average thickness."

"Nice. So, would you be interested in getting together tonight?"

"I would. Where are you located?"

"I live near 56th and Georgetown, you?"

"Nice. I live near Broad Ripple."

"Cool. Not too far away, maybe fifteen minutes."

"Cool. So, when can you be ready?"

"I just need to throw some clothes on and get your exact address."

Greg gave me his address, an apartment near College avenue. I think I have been around there before, so I knew I would have no problem finding his place. I put on some jeans, a T-shirt, and shoes. I skipped the socks and definitely the underwear. I don't want to slow things down when I get to Greg's. I grab my keys, leave my apartment, lock the door and get into my car. I sit in my car for a minute, almost trying to talk my way out of this but I didn't want to be that guy. After a minute or so, I started the car and headed out of my complex on my way to Greg's.

Driving there, I started to think about my first time with a guy when I was 19. How nervous I was, but so excited at the same time as I drove to that mall in Greenwood. I reached his apartment complex and after getting my bearings, I drove to his building. I got out my car and walks to the building and soon found his apartment. Taking a deep breath, I knocked on the door. After a few seconds, I heard the door unlock and then open and I was face to face with Greg.

"Tim?"

"Yea."

"Come on in."

"Thank you."

Greg was just as he described himself. A little taller than me, a little leaner, with short black hair and blue eyes. He was wearing a T-shirt, shorts and no shoes. I walked in and looked around. It was a typical one-bedroom apartment. The kitchen was on the right off the entry and the open living room to the left.

"Nice place."

"Thanks, Tim, it's home."

"You want anything to drink?"

"Nah, I'm okay. Thanks for the offer."

"No problem. You want to go to the bedroom?"

"Yea."

With that, I followed Greg down the hall and to his bedroom. It was a decent-sized room, with natural, brown colored furniture, including a nice wood-framed bed.

"Nice. I like the colors. I have the same at my place."

"Nice. So, I'll take it slow. Seeing it is your first time with the real thing."

"I appreciate that."

There was a moment of awkward silence as we just kind of looked at each other and around the room.

"Why don't you get undressed, Tim."

"Okay."

I started by kicking off my shoes and then pulled my shirt off, almost losing my glasses. I paused for a minute as Greg started taking his clothes off, starting with his shirt. He had a nice body, definitely a runner's body. I unzipped my pants and slid them off, my naked body now in full view of this strange man. I looked up to just catch Greg pull off his shorts, his cock now in view. I'm sure my eyes widened and I had to catch my breath, seeing a cock as big as his in person.

"Very impressive."

"Thank you, Tim."

"Yea, so much different seeing one in person and not in a picture or video."

"You want to suck it first?'

"Yea, I do."

Take a seat on the bed."

I did like Greg said and took a seat as he walked to me, his cock swaying and bobbing. This was only the second time in my life I was going to suck another man's cock and what a nice cock it was. Ted's was nice, but Greg's is much better. Slender, with a nice head and very well trimmed with some light bush on his balls. Once he got close enough, like my first time I didn't hesitate and took hold of his cock, paused briefly before taking his cock head into my mouth.

"Oh, nice, Tim."

Hearing my name as I started sucking Greg's cock, got me very excited. His hand went on my head and started caressing.

"I see you have done this before."

I sucked for a bit more before taking his cock out.

"I have, once but I have practiced on my dong several times. But this is so much better than my dong."

Greg just smiled down at me as I started sucking again, almost forgetting why I was there and had to restrain myself from trying to suck him to completion.

"Yea, I think I'm ready now. You?"

I pulled his cock out of my mouth, "Yeah, let's do it."

I knew if I thought about it, I might try and back out but I wanted Greg to fuck me.

"Get on the bed, on all fours with that pillow under your stomach. It will help."

I did as Greg asked and got on the bed, pulled the pillow under my stomach and got on my hands and knees.

"Maybe on your elbows, Tim."

"Okay."

I felt like I was in bottoming 101 and Greg was my teacher. He was so patient and gave guidance to ensure my first time was as good as it could be for me.

"Let me get some lube and a condom."

I looked over as he cracked open a condom and slipped it on his cock before popping open a bottle of anal ease and started lubing up his condom and then my ass.

"It's gonna be a bit cold, be ready."

It was a bit cold, which made my ass twitch a bit, but I knew that was nothing compared to what was about to come next.

"Just relax, Tim and breathe; it might take a bit to get my cock in comfortably."

"Okay, I'm ready."

"Okay, once you get comfortable, I'll got to work, just as fast and deep as you can take."

"Okay."

I braced myself as I felt his cock head press to my hole. I started thinking back to the first time I used my rubber dong and how I had to slowly work it in, but once the head was in, the rest was easy to take.

"Just relax, Tim, it'll be fine."

"Okay, I trust you."

"Thank you, Tim, here we go."

With that, I felt Greg's cock head pushing into my hole. My ass must have been more ready than I thought, because there was no pain, just the pressure of his cock piercing my hole.

"How are you doing?"

"I'm good, it's good." I paused and took a deep breath. "Don't stop now."

"Okay, Tim."

With that I lowered my head and braced my body as I felt Greg's head pop into my hole, giving me a sense of calm and ease deep inside me. Here I was getting fucked by a guy I just met and I was at total peace and feeling such waves of growing satisfaction.

"Oh yea, that feels so good, Greg..."

"Yeah, I'm glad."

Greg paused, and rubbed my ass cheeks before I felt him working the rest of his cock deep inside my ass.

"Oh fuck man, that feels so good," I started breathing a little heavier. "Never had a cock so deep inside me... fuck."

"That's it, Tim, you have taken it all."

"Oh fuck, it feels so good. Fuck me, Greg."

"Oh yeah."

Greg obliged and started getting a slow and deep rhythm going and even though he had a condom on, I swear I could feel the flesh of his cock pressed to the inside of my body. Slowly getting faster, but not harder and really working my ass like the total top he said he was.

"Oh Tim, Tim," Greg grunted, "you feel so good!"

"Yeah."

Yea. That was all I could muster to say as Greg masterfully worked my ass. My mind could think of nothing but how good I was feeling getting fucked. He was hitting me so deep, my ass was tingling and seem to be on fire. I'm glad I was on my elbows like he said; it was so much easier to hold myself as he fucked me. I was feeling him in my legs, they were starting to shake and feel like jelly and I was loving it.

"Oh Greg, Greg, oh fuck man!"

"Yeah, Tim, yeah," Greg started breathing harder. "Fuck you feel so good!"

His hands gripping my ass tight as he started getting a little faster and a little harder, but I was taking it.

"I'm getting close Tim."

"Yea," I grunted "okay."

Greg started only working his cock halfway, but still had a good rhythm and was still making feel it. He fucked me like that for a couple of minutes more and then started breathing faster before pulling his cock out and letting out a deep groan."

"Uh!"

The next thing I felt was his cum hitting my ass as he grunted an groaned.

"Oh fuck Tim, yes."

My ass stayed open, gaped by his fucking as he spurted at least three or four shots on me.

"Oh Tim, that was one of the best orgasms I have had in awhile."

"Yea, wow."

"Let me get you a towel and get that off of you."

"Okay."

I just laid there, catching my breath as I watched Greg go out of the room, his cock still pretty hard and then come back with a towel with which he wiped my ass off. I rolled over and smiled.

"So, you really took that, Tim."

"Better than I imagined."

"Well, I'm glad you messaged me in the room, Tim."

"So am I."

There was another awkward pause before I said I should probably be going.

"Sounds good."

I watched as Greg put his shorts on, his cock still semi-hard. I put on my jeans and my T-shirt, then slipped on my shoes. I stood up and followed Greg to the front.

"Thanks again, Greg."

"You are very welcome. I'm glad you enjoyed it."

There was a little pause and then Greg leaned in and gave me a hug. At first, I thought he was going to kiss me. We hugged and then I exited his apartment.

"Drive safe," he said

"I will. Good night."

"Good night."

I got into my car and headed home, my ass still feeling worn and worked. I got home, stripped down and jacked off thinking of Greg's cock. After shooting a good load, I brushed my teeth and went to bed and fell asleep thinking of how that was a once-in-a-lifetime experience.