Spring Fling

It was the spring of 2017, and my curiosity got the best of me. I've led a straight life up until this point, married with children, 2 cars and a house, all the typical family things a guy like me is supposed to have. But I always craved the unknown, the taboo, the unthinkable: I wanted to be with a guy.

More than that, I wanted to experience sex with a man. When I was a young kid, I had a friend named Ron who would always grab at me and try to pull my pants down and make jokes about dicks and things. One day, when I wasn't paying attention, he succeeded, getting my sweatpants and underwear all the way down. I was angry and embarrassed, standing there with my dick hanging out, and said "you happy now?" He just smiled, walked over to me, kneeled down, and took my dick into his mouth.

I couldn't even react. I was completely and utterly shocked. Once I realized what was happening, the feeling of pure ecstasy and joy overwhelmed me, and I did nothing to stop him. He eagerly sucked me for a while, until that feeling of an orgasm overtook me, and nearly passing out, and with wobbly legs, I came in his mouth. He spit it out, but seemed to enjoy it. He apologized for "pantsing" me, but said he really wanted to see my dick. He asked me if it was ok that he gave me a blowjob, and I couldn't really answer him. I wanted to say no, but I ended up saying yes, it was ok.

From that moment on, whenever we were alone, especially during sleepovers, he would blow me, and I soon began to return the favor. I found that I really enjoyed sucking dick. But I was straight, and enjoyed women more, and after we transferred to other schools, we stopped hanging out and all seemed to go back to normal for me. That is, until last spring.

After coming across some interesting online gay porn, I started thinking about the old days, me and Ron's oral escapades, and wondered how much better it might be now, with a man. I began reading Craigslist posts and getting really turned on. About a month into all this, I put my own ad on Craigslist, being truthfully honest about my situation yet being curious. After receiving a ton of creepy responses, I finally got one from a guy the next town over that seemed quite authentic and honest as well.

We agreed to meet at a Starbuck's. I was incredibly nervous, almost shaking. When I walked in, I saw him dressed as he said he'd be, and sat down. We had coffee and made small talk, sort of working me towards getting comfortable. Thirty minutes into our conversation, we were laughing and discussing all kinds of things. I was thinking to myself how I felt very comfortable with him when he asked me if I'd like to go back to his place. I was frozen. I didn't know how to respond. I just nodded yes.

I followed him back to his home, and once inside, sat down on his couch. He sat next to me, rubbed my leg, and leaned in to kiss me. Still somewhat frozen, I barely responded. He laughed, and that made me laugh, then he leaned in again, and this time I welcomed his lips and tongue as we kissed each other deeply and passionately. Very quickly my fears and nervousness washed away and were replaced with an erotic passion to go further. He asked me if I wanted to go into his bedroom, and I said yes.

In his room, he undressed quickly, and watched me undress. He was very handsome, with a beautiful 7 inch cock that was thicker than my 6 inch cock. Once naked, we climbed onto the bed and resumed kissing. His hands were all over me, cupping my balls and stroking my cock. Being inexperienced, I copied what he did, with little instructions here and there to guide me. I was a full mix of nerves and excitement, and with pre-cum leaking out of me like a faucet, he leaned down and licked it off the tip of my cock. I unexpectedly moaned out, and he took that as an ok and put my whole cock into his mouth. It felt amazing.

He told me to turn around and we started to 69, me taking all my cues from him, replicating each and every move. I was in heaven. His mouth felt wonderful and I nearly blacked out. After a few minutes, he turned back around to face me, and asked me how far was I willing to take this. I was unsure how to answer, so he asked me if I'd like to get fucked.

I couldn't even answer his. I wanted to try it so badly, but was so scared that I was paralyzed with fear. Again, I just nodded yes, and he said to scoot down to the edge of the bed and relax. He got down on his knees, lifted my legs up and back, and then started to tongue my asshole. I had never felt anything that good in my life, I was moaning before I realized I was actually making those sounds. I could feel him plunging is tongue in and out of my hole, occasionally inserting a finger or two to get me loosened up.

He stepped up and walked over to the dresser, got some lube, and squeezed it into my hole. He got closer to me, positioned his cockhead against my hole, and slowly started to push into me. The pressure was enormous, and the pain level was quite high. I almost gave up and stopped, but just then, his head popped into my ass and the pain subsided. He held it there for a moment and asked how I was doing. I told him I was a little uncomfortable, but not to stop.

He slowly pushed further and further inside me, until he was fully in, then slowly pulled back and continued this dance with my hole. More and more I felt the pain disappear and was replaced with a euphoric feeling of bliss. He started stroking my cock at the same pace he was fucking me, and after a few minutes, I blasted ropes of cum from my belly up to my chin. I couldn't believe I came that much.

He slowly pulled out of me, got a towel and cleaned me up, then rolled me onto my stomach, climbing on top of me and inserting himself back in. He fucked me for another couple of minutes, then said he was going to cum. He pulled out and I felt his hot cum land on my lower back, pooling as he panted and stroked his cock to completion. He cleaned me up and we both laid back on the bed, laughing and discussing my first time. It was everything I hoped it would be...and more.

So who would have known that this spring fling would end up being an ongoing thing. We get together two or three times a month, and my ass has responded to his cock like a key and lock, and I simply love it!