Jerkbooth
Introduction:
First story.
Well, that may not do it justice. Ever since I discovered what my dick was for, when I was about twelve, I’d been surfing the web nonstop, watching girls and women do all sorts of things! I guess that’s also pretty natural for an American kid left to his own devices in the suburbs, but that habit never really stopped for me. As high school wore on, I began to think of it just as much as a forum for exploration as an easy way to get off. I didn’t have much luck with girls (I was a virgin through all of it), so everything I saw sort of became my little secret.
As sex at that point wasn’t something I had to share with anyone, I felt free to try anything I cared to, and I did. I quickly discovered that rubbing my nipples felt amazing, and made that a habit that continues to this day. I had always had a fascination with the female body that extended to how sex made them feel, and the wealth of anal porn on the web (and the fact that I found anal hot beyond belief) made me particularly curious how that felt. It started the way it does for most (I suppose): first I started playing with the hole, then I started using vaseline to get one finger inside, then two. I noticed that though the fingers by themselves didn’t feel particularly good or bad, they made my orgasms much more powerful, so it was always a bit of a treat. Much to my delight, it seemed that the more of my hand I could get up there, the better it would feel and the more powerfully I would cum, so while I was never able to get a full fist up there, if I had the time, I could definitely fit at least three fingers.
Watching porn with these experiences in mind brought me to a whole new level of fascination with what the girls were doing: it looked like they were enjoying these huge dicks so much, sucking and fucking them to a glorious cumshot. I began to wonder what it would be like to suck one of these monsters or take it in my ass, and with this in mind tried, for the first time, to watch gay porn. Well, no matter how much I looked, I couldn’t find any that even remotely turned me on. I liked nothing about the male body, and it only made me uncomfortable to watch a man sucking off another man. Transsexual porn was only marginally better– I didn’t mind the penis, but I found the “girls” to still be too masculine, and would always end up just switching back to the real thing. High school ended around that point in my “adventures.”
I got into a good school in the midwest (I’m from tiny New Baltimore, New York) and spent my freshman year attending class, making some friends, and masturbating pretty much whenever I had my room to myself! Having a roommate and people looking to hang out meant that I generally didn’t have time for anal play, though I would always relish the opportunity when it did come along. I wasn’t much of a partier, so though I met a few nice-looking girls who showed potential interest, I remained a virgin at the end of my first year.
My second year, however, was a different story. Through one of my classes, I met a gorgeous girl named Kate who kept coming back, and, much to my delight, she was okay with just about every fantasy I’d cultivated: she loved rubbing and licking my nipples while we fucked, and we’d even begun having anal sex; that is, her taking my dick, which is about 7”, circumcised, and a good deal thicker than average. She willingly accepted early on that my sex drive was even higher than hers (which was already excellently high), and was and is very okay with me pleasuring myself if she isn’t available; combine this with a sparkling personality and I couldn’t be happier with her.
The summer after that wonderful second year, we decided to stay together in spite of the knowledge that we’d be spending full three months apart before school resumed in the fall. For the most part the first month dragged by: I hadn’t secured a summer job and I missed Kate dearly, though I was able to do pretty much whatever I wanted, since with my parents out at work every day I usually had the house to myself, which made things slightly less mind-numbing. In addition to near-constant masturbation, I took up running and weightlifting, which quickly got my 6’3”, 180-lb. frame in very decent shape. Unfortunately, though, my two main habits had to come to a temporary end: my family was having a big Fourth of July get-together down in the city and my parents and I, along with my aunts, uncles, and cousins, were staying at my grandmother’s town house were going to spend a week down there. While I’ve always enjoyed visiting the city, I knew that I would get virtually no privacy, so I wasn’t exactly tripping over myself to go.
Well, as the week wore on, I found myself needing a release badly. I never even had time to dash up to the room I was sleeping in for a quickie, as at my age I was expected to entertain some of my younger cousins. This was by no means my first long dry spell, but for whatever reason I found myself getting hard at the slightest thought of sex. To make matters worse, Kate and I had gotten into the habit of sending each other dirty texts, so every time my phone vibrated, I knew it was trouble: “I wish you were here fucking my ass right now,” I would read while sitting across a table from my mom, and would have to change the way I was sitting to hide a temporarily raging hard-on.
By the time I woke up around ten o’clock on my third-to last day there, it had become unbearable. I woke up while lying on my side with a severe case of morning wood, lying on a twin bed on one side of a room while my eleven-year-old cousin lay on another across the room reading a comic. I rolled over on my stomach to try to wait for my wood to subside before getting out of bed, but all that did was make it harder. I rolled back to my side and grabbed a book from my nightstand. It was “The Road,” an un-sexy book if ever there was one, but even while reading that it took my boner a full five minutes to subside. I hopped out of bed as it did and made a beeline for the bathroom, walking as quickly as possible in case there was any lingering bulge under my sweatpants. In the bathroom I took a piss, brushed my teeth, and texted Kate, “I’m up, and really horny. Wish you could suck me dry!” This gave me the mental image of her beautiful face moving up and down my dick, which got me hard all over again, and it was only made worse when my phone vibrated a minute later: “Mmm I’d love to feed you your cum afterwards.” When I can do something about it, I love the way this girl thinks, but right now it was torture!
I went downstairs and put two slices of bread in the toaster while pouring myself a cup of coffee. Two minutes later, as I sat absentmindedly munching on my toast and staring at the front page of the Times’ sports section, I began to think about sex again, but in a constructive way, what I could possibly do to remedy my situation. “I can’t get anywhere with everyone in the house, so I’d have to do it outdoors,” I hypothesized. “But where?”
The moment the thought occurred to me, I knew it was the only way: I would visit a jerkbooth, one of those 25-cent places. I’d never been in one (no need), but I figured that in New York, tons of people must use them. It’d be an interesting experience, I expected, and in the end I’d know what it’s like; my mind was made up.
“Hey mom.”
My mom looked up from her Arts section. “Yeah?”
“I think I’m gonna go take a walk. I haven’t been getting out much these last few days, and it’s a nice day.”
“Okay. Ask Jack if he wants to go along, would you?”
Shit! My younger cousin! “Alright, but I don’t think he will.”
I put my shoes on and bounded upstairs to the room, where Jack was still looking over his comic in bed. “Hey, you want to go for a walk?”
Jack glanced up at me, then looked back down at his comic with seemingly more concentration than ever. “Nah.”
Yes! I walked across the room, opened my bag, and pulled out my computer. A quick search for adult stores revealed that there was a promising-looking one in the Lower East Side, about ten blocks from my grandmother’s. “Okay, have fun,” I absently said as I moved out the door, then practically jumped down the stairs. “Jack doesn’t want to go, mom, so I’m gonna get going.”
“Alright, sweetie, have fun!” I was pretty much out the door already.
The ten-block walk seemed to go fast enough, mainly because I had to pay attention to where I was walking, what with no numbered streets. By the time I turned the corner I’d almost forgotten how far I’d come, but I immediately knew I was in the right place: a huge neon sign proclaimed “EMPIRE STATE ADULT VIDEO.”
As I walked up to the blacked-out entrance, I checked up and down the street to see if anybody was looking at me. Nobody was, so I opened the door just enough to squeeze through, and I was inside. It wasn’t a huge place, just a counter with a sort of odd-looking man in his late twenties (I would guess) behind the counter to my immediate left, six racks of videos, toys, and miscellaneous things ahead and to my right, and in the back, four doors, the one farthest to the left saying “EMPLOYEES ONLY,” and the other three marked 1, 2, and 3 in large white numbers.
I turned to the guy at the counter and sized him up. He was thin and had a sort of patchy beard, and he was really pale. He gave me a sort of nod before I spoke: “Hi, can I get a booth?”
“Sure, for a dollar you get four tokens. Two tokens get you fifteen minutes.”
I did a little thinking, then handed the guy three dollars. He handed me back twelve tokens and said, “Booth two. Have fun.” With this he gave me a little sideways grin, which I honestly found a little creepy. I reasoned, though, that this is a porn store, and shrugged it off as I walked to the back.
Once inside, I checked the booth out. It was fairly spacious for its purpose: about eight feet wide by ten feet deep, with a steel chair in the middle of the room, a roll of paper towels and a lube dispenser to the right, and a machine with a pretty big screen to the back of the room which displayed its options. There were all sorts of dirty things written on the wall, but that wasn’t what surprised me: on each side, there actually was a “glory hole.” I’d thought that stuff was made up!
I spent a few seconds gawking at that before moving to the machine and pressing the button labeled “MOVIES.” From there some options came up. I selected the only one that seemed to feature anal, and was told to insert three tokens to watch the film. I did, and it seemed to be the right choice: a pretty girl with a slim frame, nice fake tits, and long black hair faded in, did a little striptease for the camera, and sat down on a couch. As I squirted some lube onto my hand, a black man appeared to one side of her. She undid his pants and pulled them down to reveal a gorgeous, muscular cock, which she immediately put her mouth over. As she worked herself into a rhythm sucking up and down his dick while following with her hand, I worked myself into a rhythm as well, matching her strokes. I was hard as a rock, and soon the girl bent over to receive the guy from behind. As his big balls slapped against her and the girl started to moan loudly, I felt the slight stirring that signals the initial stages of orgasm. I loved the way the girl looked at that moment, like the dick inside her was the best thing she’d ever had, and her face scrunched up as he slowed down his strokes to grind the cock inside her.
Just as this happened, I saw something move out of the corner of my eye. Though I didn’t really think anything of it, I glanced to my left, and there was a veiny, eight-inch cock staring straight at me! For a second I thought about how strange it was, but my dick pulsed in my then-still hand and I knew that I was even more turned-on by this than by the porn. Without so much as a second thought, I moved my chair over to the cock and grabbed it with my lubricated right hand, stroking it slowly at first. The thing was hard as a rock, the way I get when I play with a nipple, so I knew the guy on the other end must have been as turned on by this as I was. I tentatively opened my mouth and put it over the head, tasting the strange sweetness of the lube while swirling my toungue around. I tried to summon up as much spit as I could and allowed a little more of the dick into my mouth, still stroking the shaft with my right hand. I quickly thought about what I like Kate to do while giving me head, and took my mouth off the cock and began to lick the shaft up and down, giving it a kiss on the head each time I came up. The big dick grew even harder, so I decided to switch to what I believed would make it cum: I put the head back into my mouth and wrapped my hand around the shaft, and began working up a rhythm, trying to take more and more of this mystery guy into my mouth each time I went down. Though my gag reflex prevented me from making it very far, I was producing a lot of saliva, so I knew that I was doing things the right way.
After about three minutes of this, my jaw was starting to get sore. Just as I was thinking about what I could do to get this guy to cum, I heard a low grunting on the other side of the wall, and the dick grew even harder, if such a thing was possible. I took this as a sign, and sped my strokes up. The man’s grunting became more pronounced, and about fifteen seconds later I was rewarded: the guy’s dick spasmed as I kept moving up and down, shooting a pretty big load cum into my mouth. It was slightly saltier than mine, but overall the taste was very similar. I still held the dick with my right hand, and released it as I became conscious of what a ridiculous thing I’d just done! I licked a spot of cum from the corner of my mouth and noticed that the girl was lying on the floor with her legs spread wide, almost screaming as the big black dick pounded her ass and rubbed her clit with his thumb. I reached back down to my own dick, still quite hard, and started stroking again. The lube had dried up a little, so I turned to my right to get some more.
As I turned I spotted another eight-incher sprouting from the glory hole of booth three, this one darker and thicker than the one I’d made cum a moment ago. I glanced back at the porno and the couple was going at it from behind, and this gave me an idea I knew I had to see through. I squirted more lube onto my right hand and got down onto my knees with my legs apart, taking the dick in my mouth and moving my right hand back to my ass. I circled the ring with my middle finger, taking care to coat it well with lube. I did this and then applied pressure, penetrating my ass with my finger while moving my mouth up and down on the cock as much as I could manage. A minute later I buried a second finger in my ass, and after giving myself time to adjust to this, a third. After a few minutes of this, I grew impatient and stood up. I grabbed a generous amount of lube from the dispenser and coated the hard cock with it, then grabbed an even more generous dollop and put it up and around my ass. It was cold, and sent shivers down my spine as I breathed in what I was about to do. Yes.
I turned around, putting my middle finger partway up my ass in order to keep it open and reaching back with my left hand to grab the big dick. After poking around for a second, I felt a slight stretching and knew the cock had found its mark, and took my finger out and started to press back on it. I stretched more as the head popped in, and this is when the pain started. As had been my experience in the past, this was one of the most excruciating types of pain I’d ever felt, but luckily, my adventurous side won out. I gritted my teeth and grabbed my asscheeks, still putting more weight back on the big dick. Each millimeter enveloped me in a new world of pain, but at the same time gave me the wonderful feeling I’d gotten with more fingers up my ass, only to a greater extent as this cock was even thicker than that.
After about five minutes, I felt my asscheeks bump up against the cold wall, and I knew I’d gone down as far as I could. I paused for about thirty seconds to allow some of the pain to fade away, and then started to withdraw the thing, keeping track of where I was so that it wouldn’t pop out. I reached the top in about twenty seconds, and then repeated the process, taking about twenty seconds to reach the wall again, then continuing, gradually speeding up. As I did this, the pain faded and was replaced by a wonderful fullness, hitting what I presumed was my prostate each time I bumped up against the wall, as it sent a surge of pleasure through my body.
Within another few minutes I was ramming myself back against the wall, grunting along with whoever was in my ass. The prostate sensation was getting intense, so I was using both hands on my nipples as I moved back and forth, impaling myself over and over and over, letting my mind focus on how amazing everything felt. In this zone, everything else faded out: I was only conscious of this perfect dick and what it was doing to my body.
As the dick grew harder, I faded back into reality, as the man behind the wall’s grunts changed to moans: “Oooo-ooohhhhh! Aaah!” I pinched my nipples hard and felt my own orgasm surging forward every time I reared back, so I increased my pace and concentrated on the feeling. The feeling of orgasm grew inside me, and just as I reached the point of no return, I felt a warmth flowing threw me, and my sphincter stretching slightly more. My dick shot its biggest load ever across the room as I reached down to stroke more out of it and held my body back against the wall, pushing the pulsating cock as far into my ass as it would go. I started to soften, and so did the dick in my ass. I slowly pulled away, and soon I felt it pop out.
As I walked over to the paper towel roll, I came to my senses: neither of the guys had worn condoms. This was New York! My face turned red as I thought of the possible consequences as I stood holding a paper towel under my ass and forcing as much cum out as possible. I felt physically satisfied beyond belief, but hell, that guy could’ve given me anything!
As I collected my pants and put them on, I wondered what I was going to do about getting tested, and what I’d tell Kate, or if I’d tell Kate. As I dazedly walked through and exited the store, the man at the register gave me the same sideways smile he’d given me when I first arrived, and I wondered to myself if the dick I’d sucked had been his.
More to follow?
