Part XVIII
I was still about half hard as Jay and I met his dad and little brother about a mile from the Porn Palace. Barry hopped out of the family minivan and gave me a middle-aged professional's handshake and a "good to see you again." I tried not to stare too deeply into his brown eyes as I returned the shake and scrutinized the man whom I had recently learned had an affinity for Playgirls. I mean, he looked so straight.
Barry patted my shoulder as he guided me toward the van so we could continue the trip toward Chicago, which, intriguingly to me, was playing host to both Wrigley Field and Jay's identical twin brother Justin. Justin -- a University of Chicago
Freshmen, a "nerd" in Jay's words, and reported Playgirl aficionado like his dad -- remained a mystery.
So did Chicago, for that matter. It had been my dream, a fantasy really, to go there. Although I had grown up in Iowa and barely ever gotten out, I loved cities, what I had seen of them anyway. It was the late 1980s, before before suburban shopping malls really started to rob Midwestern downtowns of their hustle and bustle, to the degree the downtowns had any in the first place. I had liked downtown Des Moines and loved Minneapolis, but Chicago, wow!, I could only imagine ...
Our family had planned to go to the Windy City but my dad's death derailed that, so Jay's dad and family were my tickets to getting my fantasy get fulfilled.
As I folded myself into their mobile world, I attempted to say hey to Jay's 14-year-old brother, Jeremy, but he was more interested in protecting his back-of-the-van turf and of not missing a thing on his portable CD player. So Jay rode shotgun and I took my position in the middle row as we headed out for Chicago.
I was amazed at how the Illinois landscape changed from cornfield to housing developments to office parks to a huge freeway with a train running down the middle. I had never seen anything like it. This was no Des Moines, no Minneapolis. The traffic was bad, but energizing. Jay was right: Barry was a helluva driver as he kept up with the locals, who he said were speeding around him merely because he had Iowa plates.
Barry said he sold medical devices and was in Chicago at least once a month. It was for that reason that he had earned enough hotel bonus points to score us a second room for the second night. A second room for the second night. The words resonated in my brain.
It was shortly before 9 p.m. and pretty dark when we entered Chicago's heart. I took a quick peek as we crossed what I was told was Michigan Avenue as Barry steered us to his favorite a hotel on the city's lakefront. The whole thing could not be more gorgeous. Michigan Avenue. Chicago. Skyscrapers All the people. Jay. Barry.
As we entered the hotel lobby, I smelled swimming pool and swore under my breath that I had forgotten a swimming suit. Had Jay remembered his? What about Justin? Barry? Certainly I could buy one. Swimming seemed like a good chance to play compare and contrast on Jay and Justin's identical twin bodies. I frankly could not wait, and to figure out how Barry entered the picture.
Us being guys, it took us only about 10 minutes to stash our stuff and head out on the town. Michigan Avenue was jammed with cars, cabs, and pedestrians at an hour when most Iowans were home watching TV. Stores glistened along with the fabled Water Tower that Barry explained had survived the Great Chicago Fire of 1871.
Barry led us to a pizza joint about five blocks from the Water Tower, I think. At that hour pretty much every restaurant in Iowa was closed, but in Chicago we had a ten-minute wait before getting seated in a wooden booth toward the back. Jay slid in next to his dad and I took a spot by Jeremy. I counted my blessings and wondered allowed about how great the weekend would be. I literally could not believe where I was.
But on my fourth slice of deep dish, it hit me. As I played compare and contrast with Jay and Barry, I missed my dad. Sadly, it was Jay's dad who was making my dream of Chicago kick in. I felt my nose start to fill and I really, really wanted to cry. More than anything, I wanted to hug Barry and bury my face into his shoulder.
Jay knew me well enough already to know something was wrong.
"I'm, ah, OK." When I sniffled, even Jeremy could tell something was wrong. "Just tired, I guess."
Since we were Midwestern guys, we let my sadness sit as my emotions turned more toward guilt. It involved Jay. Looking back on it, I didn't feel guilty about really, really wanting to suck his dick, or about doing whatever needed to be done to make that happen that weekend even with Jay's dad and little brother around. The guilt involved Jay but was more about Kirk.
Kirk was my best friend, and just two weeks earlier I thought he always would be. We had a bond, one that began in the junior high shower but that evolved to something surprisingly emotional, something that deepened substantially when his dad died too. But now Kirk was dating my former girlfriend, and he was back in Iowa, at home, on the farm, keeping things together. And here I was, a world away from cornfields and manure, in Chicago, living it up, eating pizza at bedtime, heading to Wrigley, and fully prepared for having a sexual experience of some sort.
As the remnants of pizza crust made their way past the lump in my throat, I felt guilty that Kirk and I were about to grow apart, and that Jay and I were not.
I liked Jay. I liked him a lot, even though he was a
Freshmen and I his sophomore Resident Advisor. Jay different than Kirk -- harder to figure out, quieter, but worth it. Jay channeled his emotions not through words but through physical activities ranging from hitting the weights to angrily pounding the dashboard of my car while declaring he didn't need "no fags" around him. If I wanted Jay as a friend, I would have to accept that. If I wanted Jay as more than a friend, I'd have to figure that out. Maybe that weekend.
I didn't want to fuck up our friendship. But but I also wanted to fuck him. At least I thought I did as I watched the sexy athlete blink away the beginnings of Friday night fatigue.
As we made our way back to the hotel, I was the one who was uncharacteristically quiet. But then my sadness and guilt were replaced by a sense of quiet realization, that I had to take a risk. I had to take a risk of having a best-friend fantasy come true.
* * *
It was 10:45 by the time we got back to the room. Jeremy wanted to go swimming, but the pool closed at 11 so Barry put the brakes on that. Barry explained we'd have more time and another room tomorrow night, but for tonight we'd have to double up.
Jeremy, thankfully and predictably, would be bunking with dad. I closed my eyes at the realization that within a very short time, Jay and I would be in bed, close to each other, close to naked.
Jay was watching me, no doubt about it.
"Stu, whoa, you are tired."
"Yeah, we should turn in, I guess."
"I'm tired too. Been a long day. Long week."
It was late, and Barry and Jeremy were in the room, so I was far from confident that something might happen. Plus, we had one more night, and another room. I plopped down on the bedspread in my Dockers shorts and polo shirt. I was almost overcome by a feeling of anticipation as I felt the box spring jostle and watched the object of my desire rest his unbuttoned baseball jersey against the headboard and cross his legs in a way that gave him a delicious lump in his jeans.
Jay found ESPN on the TV and I tried not to watch as his dad stripped to his white briefs, crossed in front of us, and headed to the bathroom begin his bedtime regimen. I thought to myself, that's what Jay will look like someday. Jeremy, for his part, remained in is own little world of headphones and CD player.
As the flickering light from the TV illuminated Jay's jeans, I wondered whether that was the pair he had worn in his high school graduation picture. I got about half hard when I glanced at the jersey and recalled the story about how the hand of Jay's girlfriend had made the black number "1" get coated with the shortstop's white semen in the passenger seat of her parents' car.
Jay and I engaged in a little soft banter about baseball and Wrigley, but neither of us directly addressed the fact that very, very soon, we'd be under the covers, shirtless, probably both in boxers. We both heard a middle-aged snore from the bed to our right, and Jeremy seemed fast asleep too, fully dressed and wearing his headphones.
I made what ended up being the first move. It was innocent enough. I took off my polo shirt first, then my Dockers, and then repositioned my almost-naked self next to the brown-eyed ballplayer who I could tell was watching out of the corner of his eye.
I felt my heart flutter as Jay seemed to be either getting tired or getting the message. I started to feel precum build as Jay pulled himself out of his high school jersey and slipped out of his t-shirt. Jay's 18-year-old skin, still golden from a warm and sunny Iowa summer, glistened in the glare of the TV set's lights. I was having trouble breathing as I heard the unmistakable pop pop pop pop pop, the sound of size 32 501s being opened button by button.
Jay wriggled out of his jeans and laid pretty much flat on the top of the bed in -- surprise! -- tighty whities, just like dad. I laid back too and counted my blessings when I realized I had no choice but to look over the lump in Jay's briefs if I wanted to see the West Coast baseball game on TV. Jays' abdomen rose and fell as he put his his hands behind his head. I changed positions to get a glimpse of the baseball player's armpits and upper chest. Jay seemed not to care as I scanned his naked torso and took note of his treasure trail, just riiiiight there. Mmmmm. I took a deep breath and thought I smelled Jay -- the scent of 18-year-old
Freshmen fresh from a minivan trip and dinner of Chicago deep dish.
I had felt this way before, with males as well as females. With the latter, society made the tension easy to explain and to channel. My contacts with my high school girlfriend seemed natural and certainly to be encouraged during my adolescence. Plus, we hadn't fucked, and I began my sophomore year of college a 19-year-old virgin. That had changed with Rebecca, but even that was socially acceptable as long as we used protection, which we did.
But the former form of sexual attraction -- between males -- was harder to confront. It was hard, amid the uncertainty of what society, our families, and our churches said could, would, and should be done. I had felt the tension with Kirk, and throughout our adolescence and neither of us had done anything about it. And now here it was there with Jay. Here was Jay. In the flesh. Next to me. Jay's flesh next to me.
I think it was about a quarter to midnight when Jay and I climbed under the covers. I wanted to roll over and smother his nearly naked body with mine, to feel my erection grow into his groin as his snaked into my crotch as well. I wanted to feel him, from his ears to his toes, and to make ample stops everywhere in between. Fuck, I was beyond horny! There was no way I was getting to sleep without having an orgasm first. I wondered whether it would somehow be with Jay, maybe with him asleep but hopefully not. Jerking off in the bathroom seemed to be an unacceptable option.
About 10 minutes passed, and the snores seemed to get louder from the other side of the room. I laid on my back and Jay was on his back too, his eyes closed. I started to masturbate myself slowly, resigned to the fact that I'd have to get my rocks off. But as I put my hand under my boxers, I was confident it would be a great cum, knowing Jay, perhaps asleep, was right next to me.
I had to see Jay's face as I jerked my dick. I planned to watch him as long as I could, with hopes I could keep my eyes on him as I planted my seed on my chest. Then I saw his eyelashes flutter.
Jay was awake! He closed his eyes quickly and turned on his side.
Jay turned on his side to face me!
I took my hand from my shorts and heard Jay breathe ever so faintly. I took a risk and got on my side too and made my right knuckle hit him about mid-chest, I'd say. Very softly I whispered "sorry."
Over his dad's snores I heard a faint response.
"That's OK."
Jay readjusted his body a little, closer to me. I moved my hand again, this time causing my knuckles to land on his abs, basically. I thought I felt a touch of his treasure trail, but I couldn't be sure.
I lowered my hand, put the palm side up, and brushed my thumb lightly against Jay to let him know where I was at, physically, emotionally, and sexually. What happened next I will never forget as long as I live.
Jay rolled onto his stomach.
I stared at the ceiling as I tried to discern whether I had Jay more by the dick or by the balls. Through the pouch of his cotton briefs, I couldn't be sure. I let my thumb and first two fingers do a little investigating, and in response Jay started rocking his hand slowly into my palm. My whole body tingled as I felt the 18-year-old shortstop start to pleasure himself against my hand. I tried to move my hand down, but I was pinned, so Jay lifted his hips to provide access for where I wanted to go, which was closer to his testicles. The feeling of Jay's scrotum through the tight cotton was utterly amazing. He felt so good, so big. Soft, athletic, manly. Mmmmm.
I played with the ballplayer's balls for about a minute in that position. As I did, I could feel his erection strain against the cotton briefs. Jay got back on his side so I'd have better access.
I heard the studly athlete giggle through his nose as I tickled his balls through his undies. Then it was time for my initial examination. I assessed the size and shape of the base of his erection, and even through the cotton could feel how much bigger it was than mine. I moved up it inch by inch, through the cotton, until reaching the elastic waistband of Jay's white briefs.
There was more penis to explore, but it seemed to be sticking out the top of his briefs. So slowly, cautiously, I touched the nakedness of Jay that I had yearned for weeks to touch. Jay felt different than me, yet the same and oh so familiar. About an inch and a half of his erection seemed to protrude outside his underwear, plenty for me to explore. I squeezed the head of Jay's penis pretty hard and let my middle finger go where it had never gone before -- against another male's pee slit. My breathing became labored as I realized I was feeling Jay's precum. I could feel Jay start to breathe heavier.
I needed to say something. I needed to communicate with Jay. So I bent my mouth toward his ear and spoke very, very softly.
"You OK?"
"Yeah."
That was all I needed to hear. I slid my hand under Jay's briefs and cherished the amazing feeling of having the 18-year-old's whole erection in my hand for the very first time. Well, not the whole thing. At 7 inches, it was too big for that. But I held what I could, "upside down" basically, with my thumb and forefinger toward his scrotum and his penis' head snaking up my wrist. I moved my hand lower until my thumb and fingers came in contact with his lightly haired balls. They were bouncy, and fun! The decently muscled stud giggled again through his nose as I played with his dangling testicles, this time skin against skin. I did what I had done in my dreams. I assessed each ball's size and shape, and then proclaimed to myself that yes, indeed, Jay's left ball was bigger than his right.
I was going to go deeper, toward his anus, but then Jay started bucking his hips in a way that caused the underside of his penis slip and slide against my wrist and forearm. Fuck, he was AMAZING! I changed my grip and grasped Jay's penis the more traditional way, with my thumb and first two fingers toward the circumcised head. I just held him for a few seconds, not moving, not jacking, but just feeling his hard erectile tissue underneath and relishing the pulsating feel of a baseball player's hard 18-year-old cock in my hand.
I was on my back, more or less. The first time I felt Jay's hand on me was when it landed on the outside of my right thigh. He kept it there until I started jacking him slowly and moved my leg in a way that signaled I wanted him to explore me as well. Jay slid his palm toward my crotch and pressed his fingers down onto the center of my five-and-a-half-inch erection. When he discovered what was there and what sort of condition it was in, the 18-year-old moved his fingers away as if they had hit a hot stove. But very softly I said "yeah," and in no time the shortstop's fingers were back and pressing against my erect underside, moving my erection slightly from side to side.
I didn't want to move my hand from Jay's erection but I had to to take this to the next level. Jay kept his hand in place until he realized what I was doing: pushing my boxers to my knees. I about came right then and there but thankfully didn't when I realized he was fidgeting with himself to do the same with his white briefs.
Jay got his hand back on my cock before I could do the same with him. I sensed that this was his very first time of touching another male's naked penis. He cupped my erection softly, like he was going to break it, as I probably had done with Andy in the northern Minnesota sauna during my first time. I, meanwhile, found Jay's dick without trouble and held it firmly with hopes he'd do the same to me.
It worked, and as I resumed jacking his dick, Jay started doing the same to me. He focused on the underside, more than I was used to, so I began doing the same to him figuring that's how he liked it. I think it was at that very moment that my feelings toward Jay really, really changed. His dick felt great in my hand, but there was more to the experience than that. Besides pleasuring myself, I also wanted to pleasure Jay, to do things that made my friend feel good. At that moment, in that Chicago hotel room, with Jay's dad and little brother just a couple yards away, everything changed.
Looking back on it, I had no idea whether Jay felt the same way. He liked dicks, hard dicks, and I had a dick, and it was most certainly hard. Jay explored the tip and then ran his fingers down the shaft until they met the base, and then investigated my scrotum with apparent curiousity. But then it was back to the object of his desire: my erection.
I glanced toward Jay's face as the light from the TV illuminated him even more. His eyes were closed, and his tongue slightly protruded from his lips. I kept looking at his face as I jacked his hard dick. He opened them halfway, and looked at me with an expression I had never seen before and really have never seen again. It was one of lust, of sexual anticipation, also of confusion, and also of "do not stop this under any circumstances."
Seeing Jay look that way intensified my sexual drive even more. I felt a potentially messy amount of semen build as I quickened my jacking and Jay did the same. By that time, Jay and I were both on our backs and the sheets were dancing in the glare from the TV screen, so if either Barry or Jeremy was awake, they'd be getting a show.
Jay started bucking his hips into my fist, and I did the same to him. And then, the ballplayer did something amazing. He put his head under the covers for a look. I took my hand from Jay's penis, rubbed my slimy palm together, wiped a little into Jay's brown hair, and positioned his head so it was on my chest. I thought about trying to push him down toward my crotch, with hopes he'd do what his dorm-floor mate Rudolf had done: give me a blowjob. But this was more than enough, for now, and was utterly amazing, and almost beyond erotic, having Jay's head on my chest, his eyes on my dick, and his family just feet away.
Jay was curled up in somewhat of a fetal position. His hair tickled. When I moved my right hand down to the back of the ballplayer's neck and put my left on top of his head, Jay's jacking intensified. I touched his back, which felt so strong. Then I went to his bare ass. I would have put my finger in his hole, since I knew he liked having one there, but my arm wasn't long enough.
I slowed my thrusts into Jay's fist, wanting this to last as long as possible. I tried to divert his attention a little by squeezing his ass and pulling his hair. But Jay had work to do. His breathing was hard and deep. When I felt the college
Freshmen's hot breaths on the middle of my chest, that is when I went over the edge. I held both my breath and Jay's head with both hands and started blasting the most powerful orgasm of my 19-year-old life.
The strength of my ejaculation was immense. I tried to be quiet but undoubtedly failed. But that initial feeling of wetness was missing. During the handful of times when I had had an orgasm close to that intense, the cum had landed on my chin or my pillow, or once even on top of my ear. This was not happening, and as I held Jay's head tighter, we both realized why.
I felt Jay's jaw muscles wince after my first amazing cumshot, but there was no way I was letting him escape from where he was. I pushed his head tighter against my chest as I blasted three more shots, and upon coming to my middle-of-orgasm senses about where my cum was landing, my ejaculation intensified even more.
After probably ten convulsions and a ten-second recuperation period, I moved my fingers to Jay's forehead to confirm where the slimy mess had landed. I massaged some of my semen it gently into his tight forehead skin as I felt a little of my cum drip from his face to my belly. I could have stayed in that position for minutes if not hours, relishing the feel of having finally cum not just with the baseball player over whom I had lusted for weeks, but on him. On his fucking face.
But Jay would have no part in such a delay, and just seconds later he moved my hand to his throbbing erection. Jay got on his back but kept his head under the covers as I resumed my masturbation of him. I peered over his body to see if Barry or Jeremy were awake, but I could not tell and to be honest I did not care. I peeled the sheet from Jay's head and nearly had another orgasm when I saw the degree to which I had made a steamy, slimy mess on his hair, face, and chin. A substantial amount of goo was on his right eyebrow, and an impressive rope of my semen ran pretty much from below his right eye, across his nose, and to his left cheek. I about fainted when I saw that yes, indeed, the rope had landed directly over the middle of the shortstop's mouth.
The fact that I had was in post-orgasm mode helped me divert my attention from the results of my pleasure to the pleasure I was continuing to provide for Jay. As I looked past my semen, I tried to see deep inside Jay, to ask him with my eyes what he wanted me to do, to make this the best orgasm of his young life. His eyes met mine with another almost indescribable look -- one of "I can't believe I'm doing this but let's GET IT ON, dude! This is FUCKING HOT!" Then Jay closed his eyes, bit his lower teeth into his top lip, tensed up his face, and got ready for a ride.
The sheets bounced in the glare of the TV as Jay bucked his hips into the air. Fuck, his erection felt amazing. It was long, and thick, but to be honest, it could've been an inch long and I would have loved pleasuring it.
I slowed my pace to a tortuous stroke. Jay wanted me to go faster, and I did eventually, but only after checking the score, making a soft comment that the A's were coming back in the 9th, and teasing out almost pathetic moans from the 18-year-old baseball player.
Jay was about ready to either cry or kill me. He sighed deeply as I fulfilled his wish and went faster and faster and held him harder and harder. His penis was so slick that I thought he had cum, but in fact it was precum, and as I jerked his 7 inches I wondered what he'd feel like when he plowed his pole into a human hole of some kind.
I thought about putting my head under the sheets as Jay had done, to get a look or maybe a taste, fresh from the tap. But I wanted to see Jay's face at the moment he came, and I moved my left hand in place to fulfill one other highly erotic idea.
Time stood still as Jay's neck muscles tightened and the veins popped out. I could tell he was holding his breath. My left hand had found the bottom of his scrotum, and I pressed as hard as I could, beneath the ballplayer's surprisingly saggy balls. With that hand, I felt his plumbing convulse with almost dizzying force. I took my right hand off his erection entirely for perhaps a half-second, and then gripped his thick shaft between my thumb and first two fingers to confirm that nothing was yet making its way through the erectile tissue.
I felt another throb with my left fingers, then another, then another. Jay bent his neck toward his crotch as if to see what was broken, but of course there was nothing broken and nothing to see. I bent his erection toward me, and finally, for his fifth convulsion, I released the pressure and jerked my right hand downward at precisely the right moment. I felt the contents of five cumshots in one land on my chest as Jay grunted in satisfaction that finally his seed was coming out, and that there was much, much more to come.
Cumshots six through probably 12 landed either on the sheets or on Jay. As I felt his young body lose tension, I confirmed that his eyes were closed and then scooped up the huge wad of his semen from my chest and fed it into my salivating mouth. His ejaculate was perhaps 10 seconds old, no more, and was the freshest cum I had tasted to that point in my life. I remember it being pretty much the temperature of my mouth, maybe even warmer, and very sweet, perhaps because of all the Coke Jay had drunk an hour earlier.
I took my hand from Jay's dick and ran my fingers through the results of what we had done. More Jay goo had landed on and around his left pectoral muscle. It was of the more watery kind, and I rubbed some of it into his left nipple and felt that it was hard. With my hand I followed a rope of cum across his treasure trail and into his navel and relished the feeling of semen coating the top of Jay's pubes.
I about had another orgasm as I explored Jay's softening, slimy dick and convulsed at the realization that the penis I had fantasized over in his graduation picture had just exploded not just in my hand, but on my chest. I went lower, to his scrotum, and touched and almost tickled the ballplayer's dangling balls. But he winced instead of laughed. It was understandable, given how tender they were.
I got up on my elbow to see if Jay's dad or brother were awake. They seemed not to be. Then I looked at Jay's face. The athlete opened his eyes, blinked away a drop of my cum, and wiped up some more. He sighed deeply, wriggled his briefs back to his waist under the covers, and peeled himself from the bed, trying to assess whether either is dad or little brother had sensed what we had done. If either Barry or Justin had looked, they would have seen their son and brother not just with a sizable lump in his briefs, but also dripping with cum -- both his and mine.
I climbed from the bed when I saw a ribbon of light indicating that Jay had left the bathroom door ajar just a touch. I knocked lightly but then entered. The ballplayer was at the tall mirror, dabbing the last remnants of my cum from his face. He had not started attending to his chest, where his semen was starting to separate in a way that made the watery part run toward his left groin. Still, though, globs of white clung to his toned torso. The sight was utterly amazing as I watched his messy chest and abdomen rise and fall with each deep breath.
Jay's eyes moved from his face to my upper body. There is little question that he fixated on what was left of the cumshot above my right pec. Since he had seen me come and gotten it all over his face and likely into his mouth, he had to have known that the sliminess on my right pec was his and not mine. Whether he knew I had eaten most of it I could not be sure.
Because Jay had taken the brunt of our orgasms and I had eaten the equivalent of five cumshots, there was considerably less cleanup for me to do. I pulled some more tissues from the holder in the wall and crossed behind the shortstop with a gesture indicating that I was there to help, but he took the tissues from me without a word and began wiping up the watery semen from the left side of his body. I handed him more, and he pulled his briefs from his waist and attended to his privates down below.
Our eyes met in the mirror. For good or for bad, we had crossed the line. There was no turning back. I looked deeply into Jay's brown eyes to get a sense of where he was at, what he was feeling. He broke the gaze first, and turned to leave. I could feel a touch of rage. Just a touch. But not at me.
"Jay, hold on. You OK?"
The gifted athlete stopped and kept his face hidden from me as he rubbed the bridge of his nose.
"Yeah, Stu. I'm fine. But I don't, I just --"
"You just what?"
"I just -- Don't know."
Jay turned and looked at me in the mirror. His lower lip was quivering. His body seemed to be trembling a little, something I confirmed by putting my hand on his bare shoulder. He did not move away, so I flattened my palm against his warm skin and massaged it more as a friend than a sexual partner.
"It's OK, Jay. We're cool. We're OK You're OK. ."
Night Number One in Chicago was complete. In many ways but not all, a fantasy had been fulfilled. What happened during our only full day in Chicago and then that night remained to be seen. There would be another room and another young man involved, Jay's twin brother Justin, who, like dad, had had a thing for Playgirls and expected to be staying the night.
As Jay headed back to bed, I looked at myself in the mirror, and knew I was going to sleep well because I was finally getting a sense of who I was, or who I was becoming.