Jack and I had been enjoying each other alone for several weeks. After one steamy session, we were lying in his bed, my ass leaking his cum after a wonderful time, when he surprised me with a question, "Have you ever thought about topping someone, yourself?"
I thought about it for a moment before replying, "Well, I am not nearly as big as you, but I have thought that I might be good at it, after all, I know what it takes to be a good bottom for you. My smaller cock means less initial pain for someone being broken in...it would be hot as fuck! Why do you ask?"
Jack smiled and said, "Evan has a friend, who is curious about a male sexual experience. He is afraid of being hurt, and Evan was wondering if you wouldn't mind breaking him in, giving him a taste of what being a bottom is like."
I smile, snuggling against Jack, feeling his cum leaking from my ass, "Tell Evan, send the guy to my place tomorrow night. Evan can tell him how to prep, and how to dress. I will give him a good time!"
I spent the afternoon preparing myself, trimming and shaving, setting the right mood in my apartment. I found some very sensual porn to put on my TV, made sure I had beer in the fridge, my bar was stocked reasonably well so I felt comfortable I could put him at ease. When my door rattled with a knock I looked at my watch; he was ten minutes early! I supposed he was eager...
I opened the door and saw a man about my height, slender, his eyes were a light gray, and very intense! I smiled and opened the door wide, "Come in, my name is Alex, and I am your host for the night."
As he stepped in I could see his nervousness. I closed the door behind him, and motioned to the living room, the TV was just then displaying a scene of two men, kissing, fondling the other's cock with their hands. I looked at him, realizing he had yet to speak, I didn't even know his name. I cleared my throat gently, looking at him, "So, you know my name, what's yours? Can I get you something to drink, beer, wine, something stronger?"
He started, as if hit by a sharp stick, "Oh my goodness, I am sorry! My name is Dave, and I am a friend of Evan, who recommended I come see you tonight. And yes, a beer would be wonderful!"
As he finished speaking he turned his attention back to the TV screen, one of the men was on his knees, just beginning to suck the massive cock of the other man. I could see Dave swallowing hard. I quickly went to the fridge and came back with two cold beers, handing one to him and motioning to him to sit down on the couch. I considered where to sit, and decided to join him, leaving the middle section open, assuming he wasn't quite ready for close, physical contact, yet.
I sipped my beer, looking at Dave. I glanced down, and noticed the bulge in his sweats. I smiled as I realized he was turned on by what he was watching. Sitting my beer aside, I said quietly, "Dave, I understand you are curious, about having sex with a man. I put on the porn to see if it would turn you on, and I can see that it does. So, let's be open about this, both of us should get naked, and take things slowly from there. How's that sound?"
I stood up, and pulled off my t-shirt, and lowered my sweats, having nothing on underneath them. My cock is average, maybe a little over 7 inches long, not overly thick, and uncircumcised. Dave's eyes went a little wide as I stripped off my clothing, swallowing once again as he saw my cock, his eyes on me making me grow hard with a suddenness that surprised even me. My balls are my best asset, as they are large and hang down perfectly.
Dave stood up, peeled off his polo shirt and unzipped his pants. He hesitated, and then a look of resolve crossed his face and he shoved down his pants and boxers. His cock was maybe six inches long, hard, twitching slightly, thicker than mine, and his balls were probably not quite as large. I let my eyes roam, admiring his slender build. I sat down on the couch, and pointed beside me, 'Sit beside me, and if you're ready, I'd like permission to touch you."