How I Ended Up With Gary

Chapter 1

It's hard for me to describe how I ended up with Gary that night.

At 22, I wasn’t really into young boys, but guys my age with a medium to athletic build. My last steady partner was an athletic education major, so he was hardly a shrinking violet.

But here I was in a dark pick-up bar at 1:30 on a Friday night. And here was what looked like an effeminate young boy flashing his green eyes at me from a dark corner of the crowded bar. He was nursing a beer, so he couldn’t be that young, and closing time was fast approaching. What to do?

Funny thing is, the more I looked at this pretty young thing, the more I became genuinely interested. Maybe a fem was just a path I hadn’t tried yet, or maybe it was just him?

Anyway, I made the approach and our eyes locked. There wasn’t much conversation to be had in the noisy bar, but I learned three things. His name was Gary, he had a breathy voice like a young drag queen in training, and he had truly captivating green eyes that I just couldn’t disengage from.

A half-hour later, we had squeezed our way out of the bar, and were on our way to his nearby apartment. At about 5’6" in height and maybe a hundred pounds soaking wet, I felt like I was sneaking with a junior high school friend. Obviously not my usual type, but we were on our way.

Despite that he had the build of a slight fourteen year old, I learned that he was a senior at a nearby college, and worked at a bookstore to share an apartment, which he moved into last month, at the start of the school term. His new roommate traveled, and wasn’t home this weekend.

Once inside the apartment, we shared a beer, and he just kept staring at me with those beautiful green eyes, and I couldn’t break the eye-lock either. Even when we started to make body contact in the narrow kitchen, we were still eyeing each other curiously.

Maybe he was as surprised and fascinated as I was to be with so preppy looking a guy as me. A grad student who worked as a bartender was, apparently, not his usual take home fare.

Usually by this time on a Friday night it is time for a desperate grope and fuck, but here they were, two guys just beyond each other’s usual comfort zone, sort of doing an edgy courting dance as if both of them were unsure about each other and where this was headed.

While we talked in the kitchen and shared our beers, I made the first move to bring him close to me, so we were in body contact at last. There was no question that we were both saying yes to what would come next, but we were still sort of feeling each other out. Talking about each other, and caressing each other with our eyes.

This was obviously not going to be just a wham-bam. This was going to be some kind of different experience.

Once our beers were finished, he pulled me into a kiss, then turned around in my grip and breathlessly asked if I wanted to see his room.

I followed him up the stairs still confused about the fourteen year old boy thing, but drawn by his eyes and the gentle seduction that was, no doubt, just beginning. He brought two glasses of wine along too.

The apartment, though small, was decorated better than you would expect for a college student, so I assumed his roommate was a little older. They had separate rooms, and I noticed that Gary’s was nicely decorated, as he turned on some dim lights and the stereo.

Finally, we were sitting on his bed, sharing our wine, but still doing the eye dance–not quite ready to jump in the sheets and fuck each other’s brains out.

I was still absorbing the young boy/fem thing, and maybe he was trying to figure out something. As if he wasn’t sure how much to offer on a first date.

Again, I made the first move, setting my glass down and rolling over to kiss him. After he set his glass down, we started to make more body contact, and I was becoming more and more curious about what might be in his pants---a little boy dick, or something surprising. But I didn’t want to grope–it seemed out of step with tonight’s little seduction---so we kept cuddling and kissing, and getting used to each other. It was almost like going to "first base" with a girl for the first time.

After about ten minutes of continued forays, and plenty of eyes contact, he reached into a drawer and pulled out a joint. He lighted it, took a deep toke and held it for a minute, then handed it to me as he slowly exited for the bathroom.

When Gary came back, he was in a terry robe, and had obviously shed his shirt and pants. Slipping into something comfortable?

He gentle straddled my lap and asked whether I had enjoyed the joint. While I answered, his eyes showed a little more fire as he raised up in my lap enough to, for the first time, reach for my crotch, and begin to loosen my belt and zipper.

The robe spread a little, and I could see he had on some silky briefs, but his hands were just a bit concealed as he fumbled to loosen my khakis, and slide them off my crotch. He stood for a second, slowly pulling my socks and pants off, leaving me in just a polo shirt and cotton bikini briefs. I would have participated more, but he seemed to be enjoying being in control, so I lay back and relaxed.

Next, he climbed back into my lap, spreading his robe again so that we were crotch to crotch, his eyes on me all the time, even while we kissed. At that point, I began to open his robe and kiss my way down his neck and chest, taking my time on the little nipples that emerged, and enjoying the slow seduction. He gently gasped enjoyment and began pressing his crotch more against mine, as his robe gradually fell open.

From there, I worked my hands downward and began rubbing his nice little dick, which felt to be about 4 or 5 inches under the briefs. We shared a smile as I rubbed his hardening penis, and then slid down between my legs to enjoy his prize.

He was kneeling on the side of the bed, his now loosened robe spread apart, and was nuzzling, then licking my cock as he peeled down my briefs. I knew I was in the hands of an experienced cock sucker as his tongue, throat and fingers worked like a symphony on my cock and balls. I knew, too, from his pacing that he wasn’t about to push me over the edge; he was just getting me warmed up for what would be a long night.

He came back up again to straddle me, still in his silky bikini brief which, by now, was tented and showed some dripping spots that I was getting anxious to taste. Again, he was seducing me with those lovely green eyes, even when we were kissing and starting to grind our crotches together. My hands had massaged my way down his back, and were gently kneading his little boy ass cheeks wrapped in silk, while he was poised over me. One of his hands kept a firm grip on my cock, while the other fumbled softly with my balls.

He seemed to enjoy being in charge, the one on top with all the control, and it was clear that he had no intention but to fully satisfy his captive. So, I left him in charge, which resulted in nothing but more of the slow seduction. Every now and then he would lean down and kiss me, or lick along my ear or neck, and a few times lick and softly bite at my nipples, but he seemed to just enjoy straddling me, and feeling my body under his, and, of course, rubbing my hard cock and caressing my balls.

Again, he lit another joint, and shared a wine glass with me, toking away as if we were headed for a deeper more mystical trance-like state. Eventually, his robe slipped off his shoulders as he swayed on his knees over me, a joint in one hand and the glass in another, still tickling me with those mesmerizing green eyes.

After the joint was finished, he rose from his trance and stood before me, a naked young boy’s body cloaked only in a silky light blue bikini brief that was hard to describe as either boy’s or girls. Still, the hard cock and wet spots left no doubt as to what should happen next in Gary’s little seduction, so I kneeled before him and began to worship his pretty little cock, first licking it through the panties, then to enjoy the tasty mouthful inside.

He really seemed to be enjoying himself as I grovelled below, paying homage to his throbbing slim five inch cock, especially when he leaned forward a little, and held my head firm while he face-fucked me for five minutes or so. I would look up to see his green eyes locked on mine, and enjoying being the god or goddess in control.

We then moved to the bed, and began a serious 69 with each of us driving a little faster. This was not the earlier gentle seduction, but something steadily intensifying to a next level.

I stopped for a wine break, and while he continued licking my cock and balls, I told him how blown away I was with him, how sexy he was, and how I thought we were going to have to cum a few times tonight. He smiled and said that he usually doesn’t open up to anyone on the first night, but felt that we were really making a strong connection.

Gary said that most guys he’s been with just seem to take him for a little boy, ready for a quick fuck, then they leave. He felt something more between us, and didn’t want to push me over the edge too soon. He was just enjoying what we were doing too much to ruin it by cumming too soon.

I told him that I wouldn’t be surprised that anybody would want to fuck his tight little ass, especially after seeing those silky bikini briefs, but I asked what he would enjoy most.

Gary said, in his breathy voice, that, as you can tell, I’m pretty fem, and have been teased a lot since I was in middle school about it--- that’s why he left his neighborhood and moved downtown, so he could fit in better. But sometimes, like with you, I enjoy feeling like I have some control of the situation.

Hesitantly, he explained that he usually is a bottom, but, for some reason, really felt compelled to slide into me for a change. I still want you to fuck me, but, "Maybe I could do you, too?"

I didn’t answer, but instead, climbed into his lap, straddling his cock, and sliding it between my crack. He motioned to the drawer beside the bed, and I opened it to remove the lube. After spreading some on my hole, and leaning him back on the bed, I began to lube and adjust his five inch prong to fit in just the right place.

His beautiful green eyes sparkled as his cock head went deeper and deeper, and I began to slide up and down. It went in easily, and was just long enough to hit my prostrate. Once adjusted, I began to writhe and moan. He was really getting a kick out of me saying, "Oh yes, Gary, Fuck me deep, Fuck me hard."

I was really having a blast playing him for a macho stud. I rolled on my back with my legs spread wide, and begged him to plow me---harder and harder. And he just kept driving away, while my hands gripped his ass cheeks and pushed him harder and harder., until his cum burst into me and he collapsed on my chest, spent but grinning with pride and satisfaction.

After he recovered, he was ravenous. He sucked the cum out of my ass, them moved to my balls, and took my cock all the way down his throat in almost one gulp. He had me kneel at the edge of the bed, and, from the floor, he brought me into a powerful face fuck, with my six inch cock popping down his tight throat with each penetration. I could feel it right down to my toes, and every nerve was screaming "yes," right up to the moment I exploded. He didn’t let the cum go down his throat, but squirted it into his open mouth, even dragging the dripping rod across his cheek---he really savored his cum bath.

Again, we rested a while, and he got us a snack and more wine before we played in the shower to clean up. After settling me back on the bed, we lit another joint, then we got back to our main focus. I started sucking him and slurping my way down to his balls. Before long, he was rock hard again, and I started to finger his little rosebud, with saliva for lubrication. God it was tight, but starting to open up, especially as I moved him on his stomach to enjoy a really deep rimming. He was writhing and moaning for a while before I turned him back over and climbed up his chest to present his mouth with my cock.

This time he really went to town, nibbling and licking, slurping from top to bottom, a real raunchy and exciting blow job. After a few minutes, he pulled my cock out of his mouth to tell me that he really needed me inside him. Did he have to ask twice?

Gary pried his legs wide as I slipped downward, and began to lubricate him. Then came what we both needed, as I my cock head popped inside with a shared moan from both of us. After we adjusted, I slowly began to pump deeper and deeper, and he started to cry out with pleasure. Before long, he was up on his knees, and I was desperately humping like the horny dog I am. The rhythm was fast, deep and powerful, and with each thrust, I could feel his tight ass ring trying to squeeze the cum out of my balls. God he was tight, so each move in or out was full of pleasure. He was also enjoying my hand working on his hard cock.

He rolled over again to lay on his back, saying he wanted to watch my face when I came, and boy, did I ever come, just a few strokes later. As I rested inside, I could really feel how powerful his muscles were, still squeezing my cock until I shuddered again and again.

By now, the sun was rising, and I was just getting ready to go down on Gary’s still hard cock. I suckled it gently for a while, but after a wild night of sex, expected that I would have to really speed up to get the cum out of it. Instead, I was just having too much fun suckling, as we lay on our sides with him slightly pumping, and me working like a milking machine. Then it came gushing out, a tasty spurt that left him crying out for me to stop–after he came the second time, it was all just to overwhelming for his cock.

So we cuddled and slept until noon. I remember waking to the smell of fresh coffee as he slid back under the covers to swallow my rapidly re-hardening cock. We entered a furious 69 and had each cum before our coffee.

I remember thinking the night before that he was not quite my type, but I guess last night showed me a new type that was now mine. I didn’t leave until late afternoon.

Since then, I had seen Gary a few more times, and we had the same great fun, but school and work schedules were never perfect for either of us. So we stayed as fuck buddies whenever the schedule fit.