I was 18, and my friend of several years (Jeff) was had turned 18 just a few days before. We played on the same baseball team, and every year for last few we had at least a couple of classes together. So we were pretty close. We were both in good shape, but Jeff always had that certain something. He was about 5' 10" and had kind of round face that made dimples when he smiled - which he so often did. He kept is dirty blonde hair a little long, but always looked well kept. His shoulders, back, chest and upper arms were sort of naturally well defined without having any kind of a body builder look, and he had the straightest white teeth you have ever seen. It was no wonder he didn't have any trouble getting a date.
Both Jeff and I went on dates with girls from school on a fairly regular basis. Jeff even had a girlfriend for a few months, but nothing ever really evolved from either of our relationship attempts. I don't know about Jeff, but I was only dating because it seemed like I was supposed to. At that age there is a lot to figure out. We were entering our senior year in high school, and it seemed like all of the guys had stories about getting laid last weekend. I tried like hell to get excited about dating, and spent my fair share of time looking at porn on the internet for motivation. My porn sessions always seemed to end the same way though. I was watching the guy.
I had been fighting this for a long time thinking it was just a phase, but it was becoming clear that my attraction was to the same sex. I didn't have any feminine qualities, and I always played sports and did normal guy things. It was a real struggle for me to begin to accept that I might be bi, let alone gay. It seemed like every time I was almost willing to admit it to myself though, I would get turned on by some drop-dead hot chick walking down the street and convince myself I just hadn't met the right girl yet. My interest in guys was my most guarded secret and I wouldn't have admitted it to anyone.
Finally I decided to indulge my curiosity and Google up some gay teen porn. I almost couldn't even type the words. I felt ashamed to be doing it, but my urge won over. Not long into my experiment, I had stroked myself to the most awesome orgasm I had ever known. Needless to say, my gay porn viewing became a fairly regular thing after that. I would watch guys my age suck each other off, and dream about having someone's dick in my mouth. That someone - I wished - was Jeff. I never let on though. Jeff and I were too good of friends for me to risk asking any questions that would lead to an awkward situation between us.
It was spring break, and Jeff and I had been out fishing in the nearby creek. Jeff had swiped a few beers from his dad and we made quick work of them. We were maybe just a little bit tipsy, but far from drunk. We walked back to his house as it was starting to get dark. Jeff asked if I wanted to spend the night to which I agreed. I just lived a few houses down and a street over, so I went and packed a change of clothes and headed to his house.
We were in Jeff's room playing video games when my problem started. Jeff was wearing some loose nylon mesh workout type shorts and sitting in a chair kind of slumped down a little. I was laying on the floor with my head propped up on a couple of pillows when I glanced over and saw his underwear up his shorts leg. He was wearing white boxer briefs. I could tell that, but I couldn't tell much else. I could just barely see the edge of his bulge and that was enough to get me excited. Boxer briefs were kind of a fetish of mine, and I was wearing an orange pair of Hollister BB's that evening. I desperately wanted to see more, but couldn't risk repositioning in some way that it would be obvious what I was doing. Just about then he lifted his hips and tugged at this underwear through his shorts to adjust his junk all the while his eyes glued to the game we were playing. I got a good shot of his package neatly hugged by his bleach-white boxer briefs. I had to get up and do something else or I would surely be noticed staring. Besides that, I was starting to get an erection that I wouldn't be able to conceal.
I told Jeff I was going to take a quick shower. He said "go ahead, there are towels under the sink". He had a bathroom connected to his bedroom. I went in and took a cold shower to try to get my mind off of the thought Jeff's gorgeous manhood in my mouth. It didn't work, and temptation got the best of me. I remembered that I had an app on my iPhone that would record video while the phone was sleeping. I knew that was all kinds of wrong, but I couldn't help myself. I positioned my bag and phone on the vanity in such a way to make it look like it was just randomly placed, then quickly made my exit knowing Jeff would be next up for a shower.
I came out and sat on the edge of his bed watching the game he was still playing. Within a couple of minutes he was done with it and announced he was going to take a shower too. I was feeling guilty, nervous, and overwhelmingly excited all at the same time. His shower took a long time, and I imagined his naked body the whole time he was in there. Finally he came out and we started playing a different game. I couldn't stand the suspense and said I had to use the bathroom.
I closed the door and immediately went for my phone. I started the video and had a semi obstructed view of Jeff dropping his shorts to reveal his white AE boxer briefs. What happened next was magic. He looked down and saw my orange underwear I had apparently forgotten to pick up off of the floor while focused on adjusting my "randomly placed" phone. He picked up my underwear and sniffed them. By this time he had moved almost center frame of the video, and I had a full front view. I could see that he was getting hard. He opened the top of my underwear as if to simulate someone wearing them, held it up head high, and licked the crotch. Then he started rubbing himself through his underwear. He stopped to turn the shower on, evidently just for the noise, because he quickly returned to smelling and licking my underwear while fondling himself. I knew I didn't have much more time before he would be wondering why I was in the bathroom so long, so I skipped forward in the video to find he was jerking off still with my underwear planted in his face. He finished up, threw the underwear back on the floor where he found it, and jumped in the shower to clean up.
By this time, I had a raging boner and couldn't believe what I had just seen. Jeff may not be gay, but he is at least curious... Very curious. I flushed the empty toilet and walked back into his room trying my best to conceal my excitement. After an hour or so more of playing video games, we decided to go to sleep. I started unfolding a blanket on the floor when Jeff said "dude, I've got a king-sized bed, you don't have to sleep on the floor". To which I responded "I'm cool with it if you are". Jeff had slipped into some flannel pajama pants and a t-shirt in the bathroom after his shower. He asked "do you care if I sleep in my underwear, I hate sleeping in pajamas"? My erection had subsided by this time, and I was struggling to keep it that way. I said "I don't care", but that was a lie. I cared very much and wanted nothing more than to see him in his undies.
He slipped off his pants and flopped down on the bead. I was near the foot of the bed and looked at him to ask if he wanted me to turn off the light. It was the most amazing site I had ever seen. Jeff in a fresh pair of white boxer briefs, his legs slightly spread to reveal his perfectly sized and neatly contained package. He was looking at something on his phone, so he didn't notice my unnecessarily long look at him - or at least I don't think he did. He said "that's fine", and turned on his bedside lamp. I laid down next to him but as far away as possible without looking weird or nervous. We talked about going fishing again the next day for a few minutes, and I started calming down. Then he pressed his feet on the bed to lift his hips and adjust his underwear. The lighting on his junk was perfect when he did that. I could see the outline of his penis and his beautiful balls, and I immediately started getting hard once again.
That's when I went for it. I said "I was listening to a raunchy morning radio show a few days ago, and they said that 70 percent of men will have a sexual experience with another guy at some time in their lives". I hadn't really heard that on the radio. In fact I completely made that up. I went on to say "I would have never thought that". Jeff - still looking up at his phone - said "that's more than I would have thought too, I hope you aren't suggesting anything" in a joking way. "No, I'm not suggesting anything" I hurried to reply while half laughing " I just thought it was weird". Jeff then set down the phone, looked at me, and asked "have you ever thought about doing anything with another guy before"? I said "I don't know... not really... I guess everyone has a crazy thought once in a while, but nothing I would want to pursue". Again, I was lying. Then I said "what about you... ever any un-pure thoughts about another guy" knowing full well that he just had an hour earlier. Jeff said "I don't know, I guess I kind of wondered what it would be like to jerk off with another guy". I paused and then said "I'll try anything once... you know... if you want".
Jeff looked at my crotch and said "take off your shorts, I'm feeling weird here in my underwear alone". I knew I was in trouble then, because I was already pitching a tent under my shorts. I figured what the hell and slid them off. Jeff looked and said "I'm starting to think you WERE suggesting something with that radio statistic". But by the time he finished that sentence, he was starting to pitch a tent of his own. That drove me into a frenzy, and a drop of pre-cum quickly bled through my underwear. Jeff looked into my eyes before leaning down to lick it off. When he raised back up, we kissed. It was absolute magic. Then we kissed again and this time I groped his bulging underwear. I said "I want to suck you off". He didn't say anything, but he laid flat on his back ready to accept.