I had only enjoyed sucking my first cock a few weeks earlier, and now I found myself hunting for someone to get closer to, someone who would want to explore my burgeoning sexual appetite. I already knew I enjoyed cocksucking. I wanted to suck more cocks, but I also felt like I wanted to know what it felt like to have a man fuck me...
I knew my method for finding my first cock to suck was not a good idea. It had been foolish, even dangerous. I needed a better way to meet a man who wanted to have my virgin ass, without the inherent risks of meeting a stranger.
It took several weeks before I found someone who seemed interested in getting to know me. As it turned out, we had actually known each other for years, it's just that I never knew he was interested in men. If we hadn't ran into each other, seemingly at random, at a bar and shared a couple of drinks I probably would have never known. His name was Jack, he was a couple years younger than me, fit, and always so well-groomed. I had actually seen him once, naked, in a locker room when we were both in college. I knew he had an absolutely perfect cock.
When we met at the bar, after several rounds of beer and a couple shots of expensive whiskey, Jack finally told me what I had hoped to hear from someone.
"I don't know if you knew this, but I am gay, and I broke up with my boyfriend several weeks ago, and I have been really lonely lately."
I have to admit, hearing Jack come out to me was a relief. As soon as I saw him, I remembered what he looked like without clothes, and I had felt a twinge of arousal. Now, to have him tell me he was gay, and single, was a dream come true. I just wanted to be mindful of his feelings, which might still be raw from his breakup.
"I'm sorry to hear about the breakup, Jack, and I am honored that you would trust me, telling me that you're gay. That can't be easy..."
Jack's eyes looked down, then back up at me, sipping his beer and then sitting it down.
"I think you might be, also. Or at least, I think you might be very curious, and even looking for someone to do some playing with..."
I smiled, shrugging my shoulders, and then putting my own beer aside I said quietly, "I have to be honest, I had my first time with a man just a few weeks ago, but we only engaged in oral pleasure with each other. I am looking for more, I think."
Jack reached over, putting a hand on my thigh. I admit, I flinched lightly at his touch, but them placed my hand over his. He looked into my eyes, a hunger clearly displayed in his gaze.
"How much more?"
I took a deep breath, my hand covering his, the warmth on my thigh spreading; I could feel my cock stiffening as I whispered three words to him, "All the way."
Jack leaned in, whispering into my ear softly, "All the way? You want to be my bottom bitch? You want me to fuck you?"
I pulled back, nodding my head, my hand pulling his up to my crotch, letting him feel my hardness, the bar hiding it from curious onlookers.
"Are you interested in a virgin? In breaking in a bottom bitch?"
Jack smiled as he felt my cock through my pants, his fingers rubbing along the stiff shaft.
"We just need to set a time and date..."
With that, we started planning for a time when we cold be alone with each other, agreeing on his place, and setting the date. Jack gave me some instructions, letting me know how to properly prepare for my first time enjoying anal sex. Before we parted, he asked me, "Would you mind if we kissed, before parting..."
I didn't hesitate, while my first encounter had not included kissing, I knew that going this route was probably not going to play out without some true affection. I leaned in, and kissed Jack. His lips parted eagerly for me, my tongue playing against his as my hand pressed his hand tighter against my throbbing cock.
----
Two weeks passed, and then the day arrived. I followed all of Jack;s instructions and prepped myself for our encounter. As the time approached, I showered, dressed in sweats, and drove over to his apartment. Riding up in the elevator I went over all that Jack had told me. I could feel my cock, semi-hard already. My mouth was dry, my nerves running rampant...what if I wasn't good? I sort of chuckled at myself, muttering to no one, "How hard can it be letting a stud fuck you?"