by Greg Scott
All the usual stuff about you must be old enough in your jurisdiction, etc. In other words, if you are underage, don't read this unless you have a really cool teacher who assigned it. Otherwise, come back in a few years, when nobody will yell at you.
Jordan and I got back to our hotel room thoroughly wiped out around midnight. We had started the day by going to the top of the John Hancock Building. From there we headed to the Museum of Science and Industry, which was super cool.
I know I'm sounding like a real geek, here. How many high school seniors use Spring Break for a trip to Chicago? In fact, neither Jordan nor I are geeky in any way. I suppose we're in the "popular" group at our school, although we cross a lot of social lines.
We're sort of minor jocks, too. We're on the wrestling team, and we run cross-country. Jordan won regional's at 125 pounds, although he didn't make it far in the state tournament. I wrestle several classes above him at 160 pounds and win the majority of my matches. My longer legs, though, give me an advantage over him at running. I usually finish a race in the top third; he's typically in the middle of the pack.
It seems like I'm trying to convince you that we're not really geeks, even though we didn't hit the drunken beaches like most of our friends. Maybe I should tell you how it is that we decided to spend a couple nights having a great time in the Windy City.
A few weeks before, Jordan has raised the idea that we go someplace for the break. I didn't want to go with our friends to Fort Meyers or the group that was going to Padre Island. I couldn't afford to go on the ski trip to Breckinridge that some of our closest buddies were taking. I told Jordan that I'd rather just hang around home and save Spring Break parties for next year when we would both be in college.
Jordan explained that he didn't want to join any of the groups, either. He wanted for just the two of us to get away together for a few days. He pointed out that we hadn't had any one on one time together in a long time.
I guess you could say that Jordan and I were best friends. We had been friends for at least seven or eight years, depending I guess on what actually counts as friendship. We had known each other longer. Mostly, though, we did things in big groups, whether it was flag football, going to the movie or whatever.
I had dated Jordan's sister for two years, and I thought we had a future together, but she broke it off a couple months ago. She found out she was pregnant. Since she and I had never done anything, it was obvious to both of us who wasn't the father! I was pretty depressed. Okay, I was devastated. My mom and dad even asked my brother, Greg, to come home from the university to try to cheer me up.
I won't get into what happened while Greg was home, but it did get me over the depression enough that I was able to get back to school. I wasn't exactly happy with life again; however I was regaining some of my usual optimism. Jordan helped me a lot during my down time. He even brought school work to me during the two weeks when I refused to go.
When Jordan suggested a relaxing trip to Chicago, it sounded like it would be a welcome change of scenery. I knew I would enjoy the time that I would be able to spend with my best friend.
I liked Jordan a lot. I guess you could say that I loved him, although certainly not in any romantic way. My brother, Greg, is the gay one in our family. I'm incurably straight. So we decided to make reservations and have our own private Spring Break.
This would be the last night of our mini-vacation. Maybe most guys would have thought of some way to extend the evening by trying to find someplace that would serve them drinks or even play a game of truth or dare, but as athletes we were used to listening to our bodies. Our bodies were clearly telling us that the day was finished.
As Jordan stripped to his boxers and climbed into his queen sized bed, I was struck again by how much he reminded me of his sister. They were about the same size, roughly five inches above five feet. If you looked only at their faces, they could be mistaken for identical twins. Their hair was exactly the same color and texture, although Sarah's was longer even though Jordan's was fairly long for a guy. I guess it would be called "dirty blonde," although there was nothing dirty looking about it.
I took off everything except my boxers, brushed my teeth and got into my own bed. I rested on my back, thinking about our day and dreading the drive home in the morning.
"Good night, Jason," Jordan called from his bed. "Thanks for agreeing to come along."
"I've had a great time, Jordan," I replied. "It's been a lot of fun. I hate to see it end. Good night."
"Yeah," I said with barely enough energy to get it out.
"Would you think I was weird if I told you something personal?" he asked.
I figured that I knew what was coming. For quite a while I had known that Jordan was gay, although he hadn't come out to anyone. I could tell by the way he looked at other guys, and sometimes I would catch him staring at me. I had kind of expected that he would use our time together to come out. I would make a good practice case, because he knew I had no prejudices and, besides, my brother was gay.
"You're my best friend. I won't think you're weird," I reassured him.
"What if I told you about a weird dream I had," he asked a little hesitantly.
"You're lucky," I said, trying to lighten the mood. "The only dreams that I remember are too boring to care about, like I'm taking out the garbage or something. I know that I have more interesting dreams, but I can never remember anything about them." I figure that I couldn't tell him about the extremely horny dreams that I still had about his sister.
"You sure you're not going to think I'm weird?"
He was nervous, so I said, "There's no way I would ever think anything bad about you no matter what you tell me."
"Well, a couple weeks ago, I had this dream where you and I were here in Chicago, but the hotel room looked different than this one. We were just hanging out. Then suddenly, I was bent over you giving you a blow job! Weird, huh?"
I hadn't expected this, but I wasn't really all that surprised. I was still trying to figure out if this was a proposition or if it was just his clumsy way of telling me that he was gay, so I probably let the silence continue for longer than I should have.
"I mean, obviously, I'd never even think of doing anything like that to you or anybody. But what do you think it means?" His voice was a little panicky as if he figured he had crossed a big line.
"Well, I'm not Freud," I said, sort of stalling as I organized my thoughts. "Everybody has dreams that have nothing to do with reality. This could be just one of those."
"Do you think I'm weird?" he asked almost desperately.
"I don't think you're weird," I reassured him. "There are other possibilities, though. Do you want to hear them?"
"Sure," he replied, but I'm not sure that he really did want me to go on.
"Well, it could be that you are a little curious and this was your mind's way of handling that curiosity," I said as matter-of-factly as I could.
"Yeah, I don't think that's it," he said hurriedly, as I could sense him chickening out on whatever it was that he had planned. This was obviously not a casual conversation that had magically happened without planning.
"Or," I continued as if he had not submitted his denial. "It could be that you never had that dream, and this was just your way of bringing up the subject to let me know that you're gay."
There I had said it. My words hung in the air for a while before he said anything.
After too long a time, he said, "I think it was just one of those weird dreams that everybody has that doesn't mean anything at all."
He couldn't do it. I figured he must not be ready, yet, even though he had to know that I was a safe audience. But maybe he just wasn't sure that I would accept his sexual orientation. I decided that I would talk to him tomorrow on the drive home. I was too tired to have a long discussion tonight.
He must have been too tired, too, because I soon heard the regular sound of his breath coming from a few feet away. He was asleep.
I must have fallen asleep quickly, too. What I remember next was being awakened by the sound of him getting out of his bed. I figured he must have to pee, so I didn't really think anything of it.
I am a very light sleeper. My brother used to complain that I would wake up when he would just turn over in bed. I think his complaint was because he could never sneak in a private, middle of the night jack-off session. Poor guy. He was just the opposite. A marching band could have come through our bedroom, and he wouldn't have even stirred. Consequently, I could pretty much jack off as much in the middle of the night as I wanted. Most nights, in fact, I took advantage of that.
Jordan didn't head off to the bathroom. Instead, he just stood there, unaware that my eyes were open watching him.
He must have stood motionless for at least a minute. At last, he broke his trance and took two short steps to the edge of my bed, where he again froze.
If I hadn't had a sense of what was about to happen, I might have thought he was sleep walking. There was sort of a zombie like ambience about him.
He leaned forward slightly and very slowly grasped the sheet that covered me. He pulled it gently toward my feet.
I focused on my breathing, trying to keep it steady so that he wouldn't suspect that I was fully aware of all of his movements. It's hard to breathe regularly when you're thinking about it. Try it, you'll see what I mean.
Once the sheet was covering only my calves, he brought his hand down to the spot where the top of my boxers met my bare torso. He moved it closer and closer to my skin.
I was reminded of games of dexterity like pick-up-sticks or the game where you have to remove blocks out of a wooden tower without making the tower crash to the table top. He moved his hand with the same care.
Finally, I could feel his hand brush the tiny hairs on my stomach. It tickled, but I resisted reacting. Then he came into actual contact with my skin and started to gingerly move his fingers under the waistband of my boxers.
If his target was what I expected, he would had an easier time of it by taking the route through my fly, but I wasn't really in a position to give advice. I had decided that I was going to continue to feign sleep no matter what.
Because of the angle of his wrist and forearm, the front portion of my boxers was being pulled down as he inched his finger tips through my pubic hairs. I watched his face as he did all this as my perspective did not allow a view of the action. I saw a mixture of fear and lust. It's possible that I was just projecting those emotions, because those were what I felt. I was a little fearful of what this might do to our friendship if he got all weirded out by what he was doing. On the other hand, I was anticipating the touch on my cock of a hand that wasn't my own.
I was surprised and admittedly disappointed when he bypassed my raging cock and continued its glaciar's pace downward. What's he doing?
I got my answer as he hooked the waistband of my boxers behind the underside of my balls. Soon thereafter, he gently wrapped his hand around my cock and rested it there, watching me for any reaction.
It took every bit of self control on my part to keep from moaning or releasing a sigh, at least. Somehow, though, I continued to breathe at the steady pace.
At last he slid his hand up and down my member. Suddenly, though, he released my cock. I panicked, thinking that he had abandoned his plan.
My fears were unfounded. He dropped to his knees, leaned in and took the crown of my dick into his warm mouth. He moved his tongue slowly around.
I'll let you in on the clever plan that I had quickly devised when I had a strong sense of Jordan's plans for me. As his hand hovered above the little hairs on my abdomen, I decided that I would allow him to do whatever he wanted to me, but that I would continue to pretend to be asleep. Then, tomorrow, I would let him know that I had been awake.
My twisted logic told me that by following that plan, I could save Jordan the stress of coming out and do him the favor of letting him do to me what I suspected he had wanted to do for quite a while. It made perfect sense to me.
It made sense until I felt that mouth engulf my cock head. At that point I raised my head slightly to watch. What I saw in the little light available in the dark hotel room could have been Sarah instead of Jordan. Although Sarah and I had done nothing more than a little through the clothing stroking and massage, I instinctively reached forward to touch her hair. Of course, I knew it was really her brother's hair, but my hand was unstoppable.
As my fingers reached the back of Jordan's luxurious hair, he jerked his head away from me, turned to look at my upturned head and practically shouted, "Oh my god, I'm sorry Jason! I didn't mean to!"
The next day, we actually laughed together about that line. "'I didn't mean to?' What kind of explanation was that? Yeah, you were walking to the bathroom, when you tripped in the dark. Your mouth unfortunately landed squarely on my cock that just happened to be hard?" We laughed uproariously.
But that conversation was the next day. On this night, I simply said, "I was enjoying it. Don't stop."
"Are you sure?" he asked with clear trepidation.
"I'm sure, but climb into bed with me; it'll be easier for you." I thought I should at least make him comfortable while he blew me. That's just the sort of thoughtful guy, I am.
He climbed into bed, with his head at my groin and with me staring at his monster of a hard cock poking out of his boxers' fly staring me right in the face. This wasn't exactly what I had in mind.
He quickly returned to his prior lip lock around my dick. He was doing extremely well, although with a bit less skill than Greg had done a few weeks earlier.
"Jordan," I said. He came up for air, and I continued, "You know I can't return the favor, right?"
"I know," he said. "I don't care. I just want to do this for you."
Strangely, I thought I was doing him a favor by letting him blow me. It was supposed to be my good deed. I had not realized that he thought he was doing a favor for me.
As he went on, taking me deeper and deeper each time, I stopped worrying about who was doing who a favor. My hand returned to the back of his head, running my fingers through what could have been Sarah's hair while I gently pushed her bother's head down further and further onto a cock that frankly didn't care whose mouth surrounded it.
Before too long, he had me fully implanted in him all the way to the root of my dick. I had no more to give. I continued watching him and completely lost all memory of Sarah for a while, focusing only on the guy--the man--the male who was giving me such pleasure.
I felt the pressure build within me just a moment before I exploded into his mouth. I realized that I had forgotten to warn him, but he didn't seem to mind. He moaned, causing my cock to vibrate with his utterance, which created an unfamiliar but entirely welcome sensation.
When my jarring climax had subsided, Jordan kept my dick in his mouth, and I could feel him swallowing what I had given him. I turned my head slightly in exhaustion and gazed guiltily as his rigid, still unsatisfied cock.
I was startled again by its mass. Of course, I had seen it before. As I said, we both wrestled and ran cross country, so we both found ourselves in the shower room together along with the other guys. I had noticed it and been a little surprised.
Here was one of the smallest guys in our class. He had short fingers and small feet, just the sort of combination that I would have expected would produce a small dick. Yet, from what I could tell, he had the biggest. A few of the guys even teased him about it, but I didn't join in. I kind of figured that it just looked bigger on him, because he was so small in comparison.
But, staring at it from a few inches away and seeing it hard for the first time in my life, his dick didn't look big just in proportion to his small frame. His dick actually was big. I mean very big.
Granted, I don't have a lot of experience with this sort of thing. In fact, until a few weeks ago, I had never even seen my brother's dick hard...and we shared a bedroom my whole life until he went to college. I was almost hypnotized by Jordan's impressive member.
Jordan broke the silence of my physical recovery by letting my softening dick fall from his mouth and asking, "Is it okay if I jack off?"
"Of course," I replied.
He rolled onto his back and wrapped his hand around his awaiting cock. This wasn't exactly what I expected. I had assumed that he would go into the bathroom or, at the very least, return to his own bed. Being unsure of the etiquette involved in such matters, I didn't say anything, though.
Watching him perform his workman like masturbation, I began to wonder what he was feeling. What's it like to jack off a cock that size? It truly was just a matter of curiosity. I wasn't aroused watching him, just curious. Truly. Irresistibly. Besides, I guess I sort of owed him.
I reached across to wrap my own fingers around his dick. Naturally, it felt entirely unfamiliar. Interesting. I slid my hand up and down, imitating the pace that he had been using.
In addition to both the length and girth, I noticed that another difference between jacking him off and jacking off myself was that his skin seemed a little looser. It seemed to almost glide over his shaft.
"That feels so good, Jason."
"I'm glad," I replied. I didn't really want any feedback.
I purposely slid my hand up farther a few times so that I could surreptitiously get a sense of what his crown felt like. That felt much like my own, except of course for the size difference.
"I've wanted this for a long time," he said.
"I know. I've known for quite a while," I said.
"Oh," he whispered immediately before firing his first shot directly at his nose, where it landed with a splat. The rest of his multiple shots made a progressive line from his chest down his belly. I milked his cock a few more strokes coating my fingers with his final, slimy drizzles.
I gave him a few minutes of peace before releasing his cock entirely and wiping my gooey hand onto his boxers. Jason got up to go to the bathroom to clean up. While he was out of the room, I realized that I still had a little of his cum on my index finger. I was about to wipe it on the extra pillow on my bed, when I suddenly slipped it into my mouth, instead.
"Huh," I thought to myself. "Not bad, I guess, but I really don't understand what gay guys see in it."
I went to sleep before Jordan came out of the bathroom. I was satisfied by the good deed--both mine...and his.
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