Twenty one years of of bisexual exploration

I was bored and up late on a spring night in 2002. My fiance was asleep as was our roommate. I had been online when they both went to bed and after awhile I drifted into an adult chat on yahoo (2003)

My fiance seemed to lose interest in sex as soon as we got engaged and I had found myself in these chat rooms more and more. Mostly it was a time waste, trying to find women to talk to, but on occasion I would get lucky. This particular night I was striking out and getting frustrated. About an hour in I got a message "having any luck?" from a username that obviously male. I responded "not really. I'm a guy btw" and he said that he was just bored. For some reason I engaged in the conversation and we chatted for a few minutes, mostly about the chat room. Then he asked me if I ever thought about men, I explained that I wasn't gay or into guys but he persisted.

Admittedly I was pretty stoned and I ended up letting him talk me into giving him 5 minutes and if I didn't get hard he would move on. By minute two my cock was as hard as it had ever been, by minute five I was giving into the fantasy and letting myself enjoy the idea of this man sucking my cock and then he suggested maybe I wanted to suck his cock and that pushed me over the edge. I tried to hold back but I unleashed one of the biggest orgasms of my 23 year old life. We chatted for a bit after, I told him how much it turned me on and how it confused me but excited me and before we parted he said something that has stuck with me "I bet you'd be a natural cock sucker, you really should try it"

Over the next few days I couldn't stop thinking about sucking another man's cock, it became an obsession I tried desperately to ignore but couldn't. I started to gravitate to gay chats, looking for men in my city, chatting, and trying to find the courage to meet a guy. 

One night I finally did find a guy in the chat that was local and fit all my criteria for my fantasy. It was before cell phones and it was late night, I drove to a store he instructed me to and called him on the pay phone, no answer, damn. I tried a few more times and realized I'd been stood up. I went home disappointed, jerked off and snuck into bed, resolved that I was "over" the whole idea.

A few months later and we had moved from the city back to our small town area. I found myself in chat rooms again, and was shocked when I met a guy from the next town over. He was 20 and we shared fantasies and said we hoped we ran into each other again.

A few weeks later my fiance went on a trip with her mother for a few days and after work on the second night I was a few bowls of weed and 3 beers into a six pack when my new local friend messaged me. Feeling, bold, horny and under the influence I said "hey what are you doing tonight? Do you want to meet?" and he was hesitant but kept the conversation going.

I was halfway through the 4th beer when he said "you know what? Let's do it". I told him I had been drinking so he would have to pick me up but I knew a spot and told him to pick me up in 20 minutes. I told him I'd be standing in front of a well known church about a block from my apartment and he said he would see me then and what car he drove.

"Oh shit, oh shit, ohhhhhh shit" I thought as I got ready and locked up "I can't believe I'm going to do this!" I thought as my heart started racing. "I'll just try it once and if I don't like it, I'll go through with the wedding" (a decision I would regret later)

I nervously smoked a cigarette as I walked the block to the church, arriving a couple minutes early. I sat in the steps and waited, going over all the things I wanted to do with him. It was a rather ambitious list given neither me or my partner had ever been with a man before. I was resolved I was going to suck him and he was going to fuck me, I was way off in my estimation.

A few minutes later his car pulls up and he he asks if I'm Jeff (a name I would go on to use with most men for my liaisons, though occasionally I used my own) I said "yes" and got in and gave him directions to a secluded spot I knew we'd have privacy.

As he drove I sized up this hunk who would unlock the world of hot, steamy, man on man sex. He was twenty, chubby, had a sad moustache and was 1000 times more nervous than I was. We arrived at our wooded destination and it was clear that it was going to be up to me to make the first move, the only problem is I had no idea what I was doing with a man. I ended up doing what I would with a woman and I kissed him.

As soon as our lips met and parted and he stabbed my tongue with his it became quite obvious, I wasn't just the first man he'd ever kissed but I was the first person he had ever kissed. After a few minutes and some kind instruction we were making out. "Ok this isn't terrible, it's kind of hot how his stubble feels on my lips" I thought and let my hand find his thigh.

I made my way to the button of his jeans and undid it and unzipped his pants, I reached my hand in and found a shrinking cock among a puddle of his cum "oh no, he already came? I didn't even touch his cock and he already came?!" But I was committed to the experience so I started to stroke his cock and kiss him. He was not even remotely well endowed and barely at a semi hard on but damn it, I came to suck cock and I was going to!

I lowered my head to his lap and looked at his rather sad, smallish cock and let myself lick the head, the shaft of his cock. The skin was so soft and smooth I couldn't resist putting him in my mouth. The musky taste of cum residue turned me on and made me moan when I thought about it. Within a couple minutes he was hard in my mouth and I told him I wanted him to fuck me. 

We got out of the car and I dropped my pants and handed him the condom I brought. His cock was maybe 4 inches and he started going soft when he got the condom on. I desperately stroked him and played with his balls and brought his erection back to life. I put my hands on the hood and bent over, moaning as I felt the head of his cock touch my hole.

What I didn't realize was that having never even been fingered I would need lube. He tried to enter me with no luck and quickly went soft. "Damn it!" I thought, it was clear I was not going to be fucked. In an attempt to salvage the experience I dropped to my knees and pulled the condom off his wilting dick and sucked for all I was worth until I finally felt him harden. A few minutes later his hand was on the back of my head and he eeked out a small load into my mouth. It tasted terrible and was not at all arousing.

I spit and wiped my mouth, he thanked me, I chuckled and we pulled our pants up and had an awkward drive back to the church. "What an absolute disappointment, I'm NEVER doing that again" I thought and decided the experience must mean I was should get married, which I did a few months later.

It would be 8 years before I tried again and that was a whole different story, but I'll save that for another time.