Man-to-Man Firsts

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Man-to-Man Firsts Page 2

by Diana Sheridan


  Something about his attitude of understanding made me start to blurt out the story. I guess I was in bad need of spilling to someone. In dribs and drabs it came out, and then I looked at him to see if he’d recoil in disgust from my admission of gayness. I was still pretty uncomfortable with myself. But Todd put a hand on my shoulder. “It’s okay, man. I understand. In fact, I’m gay too.”

  “Really?” I asked, like some kind of idiot.

  “You’ve never…done anything with another guy, then?” he asked. I shook my head, no. “You want to?” Todd asked.

  “I…I guess…I guess I do,” I said, shocking myself.

  “Now? With me?”

  “Uh-huh.”

  “I only have one rubber in my pocket. You wanna suck or get sucked?”

  “Both.”

  He withdrew a quarter from his pocket. “Call it,” he said, tossing the coin in the air.

  “Heads,” I said. It came up tails.

  He shucked his jeans and shirt, displaying a pale blond bush with a thick, pale dick, half-hard, uncoiling from the nest of pubes. Putting on the rubber, he said, “Suck.”

  I had never sucked a dick, never even pictured myself doing it. Now I closed my lips gingerly around the latex-capped corona with a combination of eagerness and the hesitancy born of fear of fucking up. Extending my tongue, I flicked it at the swollen dickmeat throbbing palpably in my mouth. Then I hesitantly began to descend the quivering dick-column that was filling the front of my mouth.

  I got it as far as the back of my mouth before I started to seriously gag. “Back off it a little,” Todd suggested. “Take your time getting used to it.” At first I was reluctant to let any of that hot manmeat out of my oral grasp, but when I started to retch more strongly, I hurriedly loosened my mouth-hold. “Work the base with your hand and suck on the top half till you get more used to it,” the sandy-blond-haired guy suggested.

  I took his suggestion and engulfed as much as I could handle with my now-eager mouth, wrapping my paw around the rest. Though his shaft felt unquestionably different from mine, having a dick in my hand was certainly a familiar feeling, and I began to jack it slowly, just as natural as can be. My mouth worked up and down the exposed top half, and my tongue once again got into the action, dragging tauntingly up and down the flat bottom of Todd’s shaft.

  “You’re doing fine,” my instructor said, in a voice that exhibited a hint of lust-induced raggedness. “Now cup my balls and work them with your hand while you suck me. That’s the way!” I had slipped my hand beneath his sac and now was lightly squeezing and rolling his gonads. “Yessssss,” he hissed approvingly. “Just like that!”

  My mouth, meanwhile, had discovered it could take just a tiny bit more of his shaft now, and I eagerly gulped more meat within my maw, and then more and more, till at last I had overdone it again and once again began to gag. But this time, when I backed up the hot, throbbing rod, I didn’t have to back up quite as far. And the next time I worked my way down, I could take still more.

  “How does it feel?” Todd asked.

  “Mmmf!” I answered, nodding my head, unwilling to take my mouth off his thick throbber for even a second to answer him.

  “I’ll take that for a positive answer of some sort,” he laughed, and then he began hunching up and down, lightly thrusting his meat into my mouth though careful not to drive so far down my throat as to gag me again. “Ooooo, yeah. Ooooo, yeah. Yeah, yeah!”

  And then, unexpectedly, he stopped, yanking his meat out of my mouth.

  “Did I do something wrong?” I asked. I was pretty sure he hadn’t come yet.

  Todd chuckled. “No, but we still have just this one rubber, and I want you to know what it feels like to get fucked.”

  A wave of terror flooded me at the thought of that huge thing spreading my shitter and plowing up my anus. “It’ll never fit!” I cried out.

  “Trust me…it will.” Todd put three fingers into his own mouth. When he withdrew them, they were generously lubed with spit. “Get on your back and hold your legs up.”

  Tremulously I followed his instructions. A second later I felt the wetness as one finger touched my quivering pucker. Todd didn’t try to breach me right away; instead he skated round and round my bunghole, tantalizing the nerves that live there. Soon my pucker-hole began to actually want to feel his finger slide in.

  He knew it, too. He knew just when to slide that first finger in within the grip of my anal sphincter and then when to plunge it deeper, till finally it was up inside me, tickling my inner walls, setting off sparks up my rectum.

  He knew, too, when it was time to add a second finger, and then, quickly, a third. By the time his three fingers were inside me, fucking in and out, plunging deep, I was beginning to wonder how much better his dick might feel up there and whether it might really be possible for him to slide it up there without ripping me apart.

  “I want it,” I said, surprising even myself.

  Todd didn’t ask questions. He knew was I was saying. He pulled out his fingers and presented his dick to me again. “Slather it with lots of spit first,” he instructed. I did as I’d been told. Once I had it in my mouth, I began sucking again. I almost didn’t want to let it go; I was discovering just how wonderful it was to have a dick in my mouth. But I was eager to feel it up my asshole too, so reluctantly I let it slide out of my mouth again.

  Once again I was on my back with my legs up, and I watched with a mixture of fascination and fear as that big, thumping club of a dick positioned its snout at my pucker-hole entryway. Then I felt Todd push.

  Suddenly it hurt. Pain seared through me. “No!” I yelped. “It hurts. Stop!”

  “Take it easy. Take a breath. It’ll ease up in a minute,” he said in a voice filled with certainty and a bit of sharpness. Then he shoved again.

  My asshole blazed. I saw redness before my eyes. My ears rang. But then two things happened. First of all, the pain crested and began to ease off. And secondly, as Todd began to make little in-and-out motions, slowly driving himself a bit farther with every forward hump, he rubbed nerves inside me that, despite the pain, brought me intense pleasure.

  Bit by incremental bit the pain eased, and bit by incremental bit the pleasure grew. Soon I was feeling nothing but pleasure and the tiniest bit of a burning sensation that was easy to overlook totally.

  “How’s that?” Todd asked. Unable to voice my answer in coherent English words, I uttered a groan that plainly told the whole answer. Reassured, Todd gave a sharp forward hunch and drove significantly deeper into me.

  I watched with awe and amazement as his shaft disappeared into me bit by bit. The sight of that thick shaft of dickmeat being swallowed up by my asshole was almost as hot as the feel of it plowing up inside my rectum. As I watched that dickslab slide up into me, I pictured it as it might be seen from the inside, entering me and coming in deeper and deeper.

  Suddenly I realized I was almost ready to cream…and neither of us was touching my dick. But once again, Todd seemed almost to pick up on my thoughts. Supporting his weight on just one hand, he wrapped the other around my ready-to-fire tool and began to jerk me.

  He was almost instantly rewarded with a geyser of thick syrup. And as I felt myself fountaining in his hand, I felt him give three fast, sharp lunges, then one last drive that carried him deeper than ever into me…and then I could feel the pulsations and contractions as he shot off deep in my bowels.

  “So…how was it?” he asked.

  The sun was fully up now. I thought I had never seen such a glorious morning. My only regret was that I hadn’t felt his lips around my dick or my dick inside him. I told him so.

  “I do have more rubbers at home,” he laughed. “It’s too late to paint the sunrise anyhow. What d’you say we go grab a cup of coffee at the doughnut shop and then head back to my place?”

  “Do we have to stop at the doughnut shop?” I asked.

  “Eager, aren’t you?” Todd laughed.

  It turned out I
liked getting sucked and fucking ass even better than the other way around, but then Todd broke out more rubbers, and…well, it was a Saturday, and neither of us had to work. By the time I limped to my car to go home, we’d gone through something like eight rubbers and I’d been well and truly initiated into gay sex.

  THE CONSTRUCTION STUD’S HAMMER

  Just looking at him made me tremble, and I knew why. The guy was over six feet tall, with muscles on top of muscles, fair skin made tan from working outdoors and freckled extensively, curly reddish-blond hair that stuck out from his yellow hardhat, sparkling blue-green eyes, a pug nose, ruddy cheeks, a square chin, and unruly eyebrows. But that wouldn’t make the average guy…the average straight guy…tremble.

  Nor would the way his tree-trunk legs filled those tight jeans. And the average straight guy—even if he was a bit of a pecker-checker in a competitive but hetero way—wouldn’t spend so much time covertly checking Sean’s basket. Noticing the bulge. Following the path of that formidable snake. Wondering if it was fully soft now or had hardened just a bit. Wondering, if it was soft now, what size it got to when it was hard. Wondering what it looked like naked—hooded or cut, mushroom-capped or more of a plum shape or….

  But I wasn’t totally straight…if I was straight at all. Not that I hadn’t fucked my share of girls. In fact, I’d never had sex with anything but girls. I’d done nothing with any other guy. Nothing at all. But I could hardly deny what I felt. I was fully aware that simply looking at, simply being near a good-looking guy—a muscular dude like Sean, a cute guy like Ed, my neighbor, a guy with a massive bulge like the veterinary assistant at the clinic where I took my dog—was enough to sprout a giant sequoia in the crotch of my pants.

  No, the signs were all there, and I’d have had to be in total denial not to understand what it was all about. But admitting it to myself—that at the very least I had gay tendencies—was a far cry from doing something about it. I was still very much of a virgin when it came to gay sex.

  And that was where things stood the day I met Sean. You see, I work in a bank. I’m a loan officer. And I had recently been transferred from doing home mortgages to doing business loans. I was supposed to meet the president of a small but growing company at the site of his outfit’s future building, now under construction, to arrange for some additional financing. When I got there, though, he wasn’t there yet.

  Mr. Powers was running a bit late, Sean, the construction foreman, explained to me apologetically. I barely processed the message. All I could take in was Sean’s big muscles, Sean’s thick legs…and that swelling snake in his jeans. It was all I could do to keep from staring blatantly. Yet I was sure Sean had noticed where my attentions were wandering all the same.

  “Is there anything I can help you with while you’re waiting for Ted?” he asked me, putting a hand on my arm. Was he implying something with that…or was I just reading something into it because I was so turned on by him?

  I certainly was turned on; my dick was hard as a metal spike and fat as a salami. It was pumping out pre-cum so rapidly that I was grateful I had a dark business suit on—though I was sure it was jutting out and tenting my pants. I didn’t dare look down and check, though. Yet at one point I thought I saw Sean’s eyes jumping up from a look-see when I had been looking around the site and brought my focus back to him. Not that my mental focus had ever been off him.

  “Maybe I can help you get a better picture of what’s going on here,” Sean said. “Of course, Ted’s likely to be back any minute…and I think I’m needed over there.” He gestured to some construction hunks who were working on the far side of the site. They weren’t bad-looking either, but they couldn’t hold a candle to Sean. “Hey…how about we down a coupla beers after I get off work? You can ask me all the questions you want. I’m sure you have some.”

  Was it a blatant come-on? Or was my horny, virgin-but-eager brain reading things that weren’t at all intended? I didn’t know. And I didn’t know how to judge it. I’d had no experience with gay dating…or sex…or…well, with gay anything. But the first step seemed to be to say “Yes,” rather than, “Well, I’m sure Ted Powers can answer any questions….” So I accepted.

  Sean said he got off at four-thirty. I’d like to be the one who gets you off, I thought, though I didn’t say any such thing. We agreed to meet at a local tavern. And we did.

  We sat at a back table. Was there a reason he’d chosen this secluded table? Once again, my imagination was running away with itself. But when his knee touched mine…and didn’t pull back…I began to have hope that I wasn’t imagining his intentions. Sean was gay. Sean wanted me.

  His thick, strong, muscular arms seemed to command my attention more than anything else. My eyes were constantly drawn to them, big and muscular, tanned and hairy, bulging and beckoning. The only thing that was able to draw my attention away from his arms at all was the light but constant pressure of his knee touching mine. And then that pressure got harder.

  Suddenly his hand was on my thigh. It didn’t work its way up my leg to my crotch…but neither did Sean pull back. He let the hand rest there, a question. I exhaled, only then realizing I’d been holding my breath. “Want to go back to my place?” Sean asked. I nodded my head, sure my voice would come out in a squeak if I tried to talk. When I rose from my chair, I stumbled, almost knocking the chair over.

  But at Sean’s house, my eagerness propelled me and overcame any hesitancy or last-minute doubts. I was naked on his bed before I could think. And then Sean had my balls in his mouth. I felt the wet heat of his mouth-cavern surrounding my orbs and wondered if the hair on them tickled the roof of his mouth. I’d find out soon enough…when I did the same thing to him. The thought made my balls rumble and my dick twitch.

  Without taking his mouth from my ball sac, Sean reached into his bedside table drawer and retrieved a couple of rubbers. He capped my ready-to-explode dick in latex and then did the same to his. I watched him stretch the rubber with difficulty over his generous-sized tool and wondered how on earth that whole thing was going to fit in either my mouth or my ass.

  The burly construction stud prodded my ball sac with his insistent tongue, meanwhile squirming a finger between my tightly clenched butt-cheeks to zero in on my quivering rosebud. Finding my anal portal, he paused at the entryway and then began using gentle but insistent pressure to worm his way inside. My sphincter muscle, unaccustomed to anything going up there, fought against it. Though I tried to will my sphincter to relax and accept the finger, the feeling was strange, weird, and almost scary, and my muscle kept tightening and fighting to keep him out.

  Sean was persistent, though, and finally wormed his way in. Then that finger burrowed up and up inside me, till he was touching my prostate. Oooooh, what a feeling I had when that finger rubbed across my little walnut gland. I’d heard that a prostate massage could make a guy spurt off, without his dick even being touched, but I’d never believed it till I felt it. Suddenly I was on the edge of orgasm…and Sean was still sucking my nut sac and not even touching my rod.

  Fortunately Sean was experienced enough to realize he had me on the edge of orgasm. He pulled his finger back from my prostate just in time to keep me from firing off and concentrated on finger-fucking me without massaging my prostate. A second finger soon joined the first one, and then a third. He was continuing to suck my balls while thrusting three fingers in and out of my awakened asshole in rough, demanding motions.

  Sean’s mouth released my ball bag from its suctioning grip, but his tongue remained prodding into the squishy sac. Then he began licking his way up the wrinkled, bulging nut bag till he’d reached the base of my dick. Now his tongue began a slow, torturous journey up the underside of my column till at last he reached the glans. Prodding through the latex, he dipped into my welling slit and smeared the syrupy pre-cum around my corona.

  Then his lips closed around my swollen dickknob.

  Heaven.

  Slowly those lips crept down my quivering knob, en
compassing more and more of it in their grasp. Now he had my whole swollen corona enclosed in the loving, wet warmth of his mouth. And still his lips were descending my dick-column, down and down and down, and now he had three-quarters of my shaft in his greedy, gobbling mouth. And still he was taking more, and more, and then my entire shaft was buried in the searing heat of his mouth, my knobhead reaching down into the tight confines of his gullet.

  I was so close to spurting! I tried to hold back—I wanted my first blowjob, my first gay encounter, to last as long as possible. There would be other blowjobs, I was sure, other encounters with guys, maybe even with Sean, but there would never be another first. But my willpower was weak in the face of Sean’s insistent mouth. His tongue rippled up and down the underside of my dickshaft. His throat muscles wrapped their python-like way around my quivering knobhead. His mouth closed tight around my shaft.

  And I blew. My balls suddenly constricted, powering out a jet-propelled stream of hot cum-sauce, and I felt the globs of cum rocket up my cum-tube and out the piss-hole end of my dick. My whole body tensed as the orgasm hit me like a palpable force; then I relaxed utterly, a limp mass on the bed.

  But Sean wouldn’t leave me lying there limp for long. He gave me a minute or two to enjoy the sensations that were washing across me; then he said, “Okay…lift your legs up.” And he hoisted my legs to his shoulders, with my help.

  His only lube was spit, and at first my bunghole refused to admit his dick at all. “Jeeeeze! You’re tight as a fuckin’ cherry!” he swore. Prodding and poking, he still couldn’t get in. “What’s up?” he finally asked me.

  “Um…I am…uh…cherry,” I finally admitted, embarrassed to let this muscular stud know how inexperienced I was. But his attitude changed totally when I made my confession. Rather than expressing contempt, he acted as if he had won a prize.

 

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