Out with the Old, In with the New

I was 28. Towards the end it was a bit of a rocky relationship with my girlfriend, and I think we both knew it was just a matter of time before one of us couldn't take it any longer. She made the decision for us by disappearing one evening with all her belongings before I arrived home.

She worked as a theatrical performer so naturally all of her friends were fun, outgoing, talented and attractive. I had become friends with most of them myself, so they still talked to me long after she decided not to. But one friend who lived in my neighborhood was quick to text me after hearing the news of the break up. I was pretty sure I knew why the texts came so soon and so frequently, however I decided to play it cool and let her friend steer the conversation over the next two days. It was basically small talk mixed with the occasional concern for me and how I was feeling. It wasn't until one particular comment that gave us the opportunity to easily take the conversation in the direction we knew we both wanted it to eventually go.

"That's why I've given up on girls, they're too complicated" Chris texted. After all, most of her theater friends were gay males just as he was. "Maybe you should switch over :)" he said, half joking. I knew this was his way of testing the waters, but to his surprise I told him that I've been down that road already. "You've been with guys before?" he asked. I told him that I've only been with one guy- just a handful of times. "That's hot! Tell me about it" he texted. So I proceeded to text Chris the story of my first experience with another guy.

It was a weekend night about 3 years back, and I was performing as a musician in a club. After the set I was approached by a guy with very similar features as mine- tall, nice build, short brown hair, a bit of scruff. He told me he enjoyed the show and said my next beer was on him. After some small talk, he wrote down his number and said "let me know when you're here again, and if you drink too much you can always crash at my place." He smiled and shot me one last look as he left the club.

The next weekend I was at a different club near my home, but after a few drinks I remembered his number stored in my phone and I decided to text him. "Hey man, at a different club tonight. If you're in the area you should come out." It didn't take long at all to get a response.

"Sure, but if I drink too much I'M crashing at YOUR place ;)".

I had thought about being with a guy before, but never seriously considered it as much as I was this particular night. I knew I would need a little more to drink, so I ordered up a shot and texted back "No problem :)". After about an hour and no text, it was getting late and the bar was closer to closing for the night but at this point I was counting on this encounter happening. I texted one more time, "Getting late, you going to make it before the bar closes?"

He responded right away - "on my way, I was in for the night when you texted me so I had to get ready." I knew that he wasn't coming for a drink at this point, he was coming for me.

So I decided to cut right to it- "You want to just meet at my place?" I said.

"Send me the address, see you there" he replied.

I headed home, and it was only about 10 minutes later that I heard a knock on the door. I was shaking with anticipation at this point. When I opened the door he looked even better than he did the week before- trimmed beard, fresh haircut, and smelled of cologne. I invited him in and offered him a drink, but his reply was "couch or bedroom?"

"Couch" I replied, without missing a beat. I sat down and he sat down next to me, and within seconds his hand was on the outside of my jeans between my legs. "I've never been with a guy, so go easy" I told him.

He smiled and said "you won't be saying 'go easy' by the end of the night" as he squeezed my dick through my jeans. I put my hand on his and its size felt similar to mine.

"Six or seven?" I asked.

"Six and a half" he responded with a laugh.

"Perfect" I said, as I unbuttoned his pants and got down on my knees in front of him. I pulled down his pants and boxer briefs to reveal a nice six and a half inch circumcised cock, just a little thicker than mine. I smiled and took it in my hand as I started to lick the shaft from bottom to tip. From all the blowjobs I had gotten in the past from girls I knew what I liked, so applying that knowledge I took the tip in my mouth and started to work my mouth around his whole penis until I felt I couldn't take anymore, which surprisingly didn't happen for almost the entire six and a half inches. I worked it with my mouth for about a minute.

He finally let out a loud moan and said "you're a natural, can I get a little rough with you?"

I pulled his cock out of my mouth and said "please do".

We went up to the bedroom and he took off his shirt, and told me to take my clothes off and lie on the bed face up with my head over the edge. As I did, he stood over me with his balls against my forehead and said "open up". He took my head with his hands and without a warning began fucking my mouth as his balls bounced against my nose. The smell of cologne was strong and the taste of his dick was better than I could've imagined. I gagged a few times, but when he asked if I was okay I told him I never had been better. He reached across me and began jerking me off as he continued to fuck my throat. "Are you ready to get fucked? he asked.

"Uh-huh" I said, muffled by his cock still in my mouth.

He sat me up against the headboard and put my feet over his shoulders. Fortunately he had brought lube, and squirted a few drops on his fingers as he worked them around the base of my balls and the outside of my ass. "This will hurt at first" he said as he pressed the tip of his dick against my ass. He was right - there was a short sensation of pain, but that was quickly overcome with a rush of pleasure as his cock slid up inside of me.

"Oh my God, that is amazing" I said barely able to speak. My dick was so hard, and I was worried that I was going to cum before he even had a chance to fuck me properly. I grabbed his ass and pulled him in closer, taking all 6 and a half inches inside of me.

"You're going to make me cum," he said. It was perfect, because I knew I couldn't handle much more before I did.

"I want you to cum" I told him. "Fuck me and cover my face with it". He only got in about 5 more thrusts before he started moaning loudly.

"Fuck dude, I'm gonna bust!" he said. I started jerking myself off as he pulled out of my ass and sat up higher on his knees while straddling me. His cock was two inches from my face as we were both jerking ourselves, and finally he let out a long moan as his warm cum shot out onto my cheek and forehead and dripped down across my lips. I immediately came, and felt my cum hit his ass and drip down onto my stomach. He took his cock and smeared the cum across the giant smile on my face. He smiled and said "See you again soon" as he climbed off me and gathered his things, getting dressed on the way out. I heard the door close and the car leave as I lay there, covered in both of our cum, trying to figure out why I hadn't possibly done something like this earlier in my life.

"So, that was my first time", I texted Chris. He was in awe, since he had only ever seen with girls in the couple years he had known me.

"Dude that is so hot, I can't focus on anything right now" he said. "I need to get off before I do anything else today".

I texted back - "Wanna come over?"