This story, modified to protect the anonymity of those involved, blends fact and fantasy.
Reader feedback is welcomed, and the author will do his best to answer questions and respond to comments. Contact him at hairy.jacques@yahoo.com.
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I felt myself crest the wave. My whole body stiffened. I exhaled sharply and shot one, then two, then three, then four thick volleys of cum into Greg's mouth. I started to shudder. The sensations were just too much. I bent forward at the waist as Greg continued to suck me. I could hear him gulp and feel him swallow. Finally, right before the moment when I couldn't take it anymore, I pulled away, pushing him back against the bed before buckling over on top of him. Our lips pressed together as his muscular arms embraced me. We panted as we exchanged wet, sloppy kisses and my hips bucked forward =into the heat and hardness of his cock.
I could barely see straight. I don't think I'd ever felt an orgasm so intense. Greg pressed his tongue into my mouth, sharing the remnants of my cum. I nuzzled his neck. I felt his fingertips lightly stroke the naked skin of my back. It was a tender moment. I'm not sure how much time passed: maybe several minutes, maybe not. When I finally pecked him on the lips he smiled at me.
"That was amazing," I whispered.
"You're an amazing teacher," he replied.
"Last night or just now?" I asked. I wasn't sure if he had learned from my example or my instruction.
"Both," he said, nibbling the edge of my ear. "And there's a lot more I want to learn."
Even though I had just cum, I could feel my erection begin to stir. I pressed forward into his groin. The cotton of his underwear provided just the right amount of friction on the underside of my dick. I could feel alongside it the heat of his own throbbing cock, still sticking out of his fly.
Regaining a bit of my strength, I propped myself up on my elbows. This allowed him to shift a bit. His palms slid down from my back and traced up my sides to caress my pecs. His fingers gently pinched and pulled down on my nipples. Releasing them, he raised his arms and clasped his hands behind his head.
"You like my armpits?" The tone of his voice made it a question, but it could have worked as a statement.
I love armpits, and I especially loved Greg's. Pit hair had turned me on since junior high school, when it became for me a visible sign of masculinity and sexual maturity. It helped signify the difference between boy and man. Real men had hair under their arms. To me, pit hair on a guy is like blooms on a rose. I pressed my nose into the damp hair of Greg's left pit. The smell of him brought about an almost involuntary reaction: I thrust my stiffening cock into his cloth-covered crotch.
"Easy tiger," he said, quoting my words back at me. "Let's slow things down for a couple of minutes. We can catch our breath."
I have to admit feeling kind of disappointed. I didn't want to take a break from what at that point was the hottest hookup of my life. But of course there's give and take in every relationship. "You want to take a shower?" I offered.
Greg raised an eyebrow. "Do I need one?"
"Hell no," I whispered. "I love the way you smell."
This caused him to smile. "What I had in mind for slowing things down," he said, "was something both of us might like. Any interest in giving me a tongue bath?"
I didn't need to be asked twice. I pressed my face back into his pit, inhaled deeply, and extended my tongue. Soon I was in danger of suffering from sensory overload. There was the visual, of course. All the muscles of Greg's chest and arm seemed to point toward the manly canal between them. And then there was the fact that Greg's pit hair was smooth and silky but acquired an almost coarse texture when matted down with my saliva. He tasted salty and his manly aroma verged on the animalistic. It wasn't the freshest sweat, after all. He'd started perspiring hours earlier at wrestling practice, and then again he soaked the fabric of his PT shirt running to my place. But all this sweat, all this musk, had been refreshed and recharged during the erotic heat of his submission to my cock. So he was moist, and not only with my saliva. There was nothing rank about his pits, at least not to me. His scent was strong but also, if not exactly fresh, somehow young. In other words, his odor was less like the smell of an older dude at the end of his factory shift and more like a college jock exiting a gym. And that was Greg: a college jock. The only thing regrettable about licking and sucking his armpit was that it caused the taste and smell to dissipate. But if Greg's sweat was disappearing as I exchanged it with my spit, his gentle sighs and the caress of his strong fingers in my hair signaled that he remained very much in the moment. So did his cock, which throbbed and leaked alongside my own.
I fought the urge to keep thrusting, in part because I'd been admonished to slow things down and in part because I knew that, if I sped things up, I'd end up cumming onto the fabric of his tighty whities. I had better plans.
For the moment, however, I contented myself with his other pit. "Contented" is too weak a word, of course. I could hardly believe I was lucky enough to get so up close and personal with Greg. He was a physical specimen, a total stud, a premier Naval Academy athlete, and no doubt the object of the fantasies of many young women and more than a few young men.
Certainly he was a dream to me, and yet all of this was real. It was even real that Greg, a college wrestler and future naval officer a decade younger than me, seemed almost as turned on by me as I knew I was by him.
That's when he flipped over on top of me. It was as if he had read my mind and wanted to validate my thought. He wanted my body. He pinned my arms over my head and returned the favor, suddenly feverish in his need as he swabbed my pits with his tongue. He quickly turned his attention to my nipples, sucking with his mouth, nipping with his teeth, and swirling with his tongue, which he then flattened and extended in order to drag it across the hair on my chest.
As his head rose up from my collarbone he established eye contact. I held it. I wanted to say something but resolved to remain silent for a moment. After all, it was his thoughts I wanted to hear.
His eyes sort of sparkled as he said it: "I've wanted this for so long. Not just with any dude, but with someone like you, who would be my coach."
At that moment my hunch was that he wasn't asking for role play. He was asking for mentorship. In hindsight, I'm fairly certain I was right. He didn't want to be bossed around or barked at. He wanted to be guided by a guy who knew more than he did and who could help him reach his potential. I was flattered he'd see me this way. More to the point, I resolved to be up to the task.
I rolled him over onto his side, running my hand along the length of his torso, his briefs, and then his naked thigh. I grabbed his cock, still hard and leaking as it projected from the fly of his BVDs. Releasing it, I let my fingers trace a path north from the waistband of his underwear. I followed the short little hairs of his treasure trail up to his sternum and reached left and right to caress his muscular pecs.
Then I nudged him backward against the mattress. I couldn't resist any longer. I had to taste his cock again. I started by kissing him on the lips but quickly worked by way down, tracing my tongue over the patch of hair at the center of his chest and then following the path of his treasure trail. By the time I reached his navel I was fondling my cock, just to make sure I was hard and ready to go. I was. As my eyes soon confirmed, so was Greg. His dick was protruding obscenely from his briefs.
I had denied myself long enough. I licked my lips, took in the sight of his throbbing cock, and lowered my face. Starting at the base, immediately above his cloth-covered balls, the tip of my tongue traced a feather-light path along the underside of his shaft. As I reached his prepuce, that extra-sensitive spot where his shaft met his helmet, I started to gently flick my tongue. This brought forth a gasp from Greg and a tiny dollop of pre-cum from the tip of his cock. I dipped my tongue in it and then pulled back. His sticky juice, thin as a spider web glistening in the light, for a long second refused to let go. I then got down to business. As my lips surrounded him, my nose went to work, inhaling deeply. His musk was strong. He had been sweating all afternoon -- first at wrestling practice, then on his run, and then during the course of our hot hookup session. It was such a goddamn turn-on to smell him. So much so that I relinquished his dick and pressed my nose into the damp fabric of his briefs. I inhaled and felt my own cock stiffen. My lips latched on to his underwear and started to suck on the cloth, drawing out the salt of his sweat. I tongued his balls through the fabric, pulling first at the left one and then the right. The taste and the aroma, manly and strong, called to mind my own college memories of locker rooms full of hot young men, their pumped-up muscles glistening with sweat and confidence.
For the past 45 minutes, the sight of Greg's cock, protruding through his fly, had tantalized and tempted. It was like I was a kid again, and my most hoped-for Christmas toy had been left partially unwrapped under the tree. Of course I wanted to rip off the last of the wrapping paper. But I also wanted to prolong the anticipation and expectation. I wanted to have my cake and eat it too. Now, I decided, was the time to eat the cake. It was time to finish the unwrapping of Greg's gift to me.
I hooked my fingers under the waistband of his BVDs and slowly pulled it down. The first inch merely uncovered more of his treasure trail, but the second inch exposed the top of his pubes. I kissed, smelled, and tasted his silky hair before pulling down another inch or so. This exposed most of Greg's bush and the very base of his turgid cock. As my nostrils made contact with his nest of hair I breathed in the fullness and intensity of his musk. My cock twitched; it was so hard it almost hurt. Finally I pulled Greg's shorts down far enough that his shaft slipped through his fly and smacked back against his lower abs. I paused for a long second to take in the sight of him. Then I swallowed hard and did my best to cover my teeth with my lips.
As he filled my throat, I could taste not only his salty flesh but also the sweetness of his pre-cum. Soon I was bobbing up and down. I felt my eyes water as the width of his cock stretched my throat. But this only spurred me on. It was as if I couldn't get enough of him. And of course, I couldn't. I couldn't possibly get enough of Greg. I wanted all of him.
As his pubic hair tickled the insides of my nostrils I backed away. I hooked my hands under his knees and lifted his legs. This exposed his balls and hairy ass crack but his BVDs, still mid-thigh, constrained his range of movement. I wanted full access, so I pushed his underwear down his muscular thighs until he was free of all constraints. As Greg grabbed his ankles, I saw his ass spread before me in all its glory.
For a guy with only a moderate amount of hair above the waist, Greg had quite a furry ass. Dark brown hair fanned outward from the center of his crack to dust his firm, full asscheeks. His heavy balls were adorned with fine, longish strands. And then, encircling his asslips, there was a dark, dense moss that outlined my target.
For a brief moment I had second thoughts. Keep in mind, at that point I considered myself basically straight. I'd had fun times with other guys, but the main focus of my sexual energy was my wife. And now I was staring longingly into another guy's hairy, sweaty, and no doubt not 100% clean ass. On one level it was gross. But on another it was hot. Very hot. Even more than his cock, which his teammates and roommates probably glimpsed on a regular basis, his asshole was a private part, taboo and unseen by the world. But now Greg, his knees pulled up to his chest, was inviting me to have my way with it. To share, in the fullest sense of the word, intimacy with him. I felt my dick throb. I could feel my mouth water. I decided to go for broke.
Palming his asscheeks and pulling them outward, I dove face first into his ass. My tongue hung broad and flat as I licked and sucked his hole, drowning it with my saliva, smelling and tasting his body's deepest, darkest secrets. None were too shameful. Greg tasted amazing. Meanwhile he was gasping and moaning almost incoherently: "wow, wow, wow-wow-wow," "more, more," "sir, thank you," "yes, yes," "fuck yes," and "oh, fuuuuck!"
That he was loving this so much made me love it even more. Mostly, it removed from my conscience that twinge of hesitation and, even, shame. If he loved it and I loved it, what could be wrong with it?
I licked my middle finger and pressed into the entrance of Greg's ass. He was tight, of course. "Push out," I whispered, "as if you're taking a dump." Suddenly I felt him open up to me. There was still a bit of resistance but mostly just accommodation. My finger sank in to the second knuckle. I circled around inside of him with my fingertip while using my tongue to trace the length of the underside of his cock. I took him back into my mouth while pressing forward with my finger. My digit sank in all the way while he groaned and rewarded my tastebuds with another little dollop of his nectar. I then started to stir around inside him, working my finger in circles and then in and out. He shuddered as I grazed his prostate, so I focused my attention on this swollen little nub. He gasped. He started panting. My mouth released his dick. "Are you okay?" I asked. He answered in a raspy voice: "Yes. Fuck yes."
I took his words as permission to up the ante. I withdrew my middle finger from his ass and plunged it in my mouth. I know it might sound kind of disgusting, but damn if it didn't taste good. Tangy, and definitely more savory than sweet -- but good all the same. I added my ring finger to my mouth, getting it wet as well. Then I took these two fingers, slicked up with saliva, and worked them back into Greg's hole.
I watched his eyes roll back as my knuckles cleared the clench of his hair-fringed sphincter. I heard him whimper. Then I heard him whisper: "so fucking good." I loved that he was comfortable enough to verbalize his feelings. "Fucking great," I enthused in a hushed tone. For some reason I was whispering too. As I gazed upon his ass I noticed on one of my fingers a blaze of gold. My eyes focused. It was my wedding ring. For a second I felt a pang of guilt. A second after that, all I could feel was the throb of my cock and the silky clench of Greg's ass.
I scooted up to kiss him on the lips. He kissed me back. As a matter of fact, he basically gobbled my lips. I reached down to jack my cock with my free hand. Then I reached into the drawer of the end table. This was the "guest room," but for my wife and me it was also a getaway. We sometimes slept here on long weekends and at other times when we wanted an easy change of scenery. She and I had great sex here. But when I reached into the drawer with my wife in the bed, it was because she was sometimes dry where most women are moist.
I pulled out a bottle of lubricant and applied some to the fingers that were causing Greg to moan and pant. He was taking nicely to the penetration, but I knew that my dick would stretch him past the point of comfort. I wanted his first time to be memorable for the pleasure rather than the pain. I wanted him ready.
I also wanted to savor the experience for myself. It's not every day that you get to pop the cherry of a Naval Academy midshipman who just so happens to also be a college wrestler who just so happens to be one of the hottest guys you've ever laid eyes on. I was definitely lost in the moment, but in the back of my mind I also knew that this was going to be one of the most memorable sexual experiences of my life.
I remembered my own advice: make the most of your senses. I took a moment to really feel the interior of Greg's ass. It was slick, but not entirely smooth. There were little ridges of muscle and the subtle bumps caused by blood vessels beneath his skin. And then, as I spread and rotated my fingers, I could feel the firm little scallop that was his prostate gland. I applied pressure and listened for a reaction, but Greg's grunting and groaning actually stopped. Instead I heard a sharp intake of breath. As I saw his head tilt back, his jaw dropped. His eyes darted upwards and I actually noticed his pupils contract. My fingers still spread, I slowly withdrew, dragging against the walls of his rectum. I noticed the hairs encircling his ass lips, slicked up with lube, clinging to my fingers as they pulled away from the heat of his hole. I lowered my head and extended my tongue, tasting the tangy juices on my fingers. I inhaled his musk. Up close I surveyed the crinkly skin encasing his balls and then let my eyes wander up his stiff shaft, bulging with veins just below the surface of his skin, all the way up to his cockhead's tip, which was glistening with even more pre-cum. My tongue followed my eyes and I tasted his salty sweetness.Once more I went down on him, pressing my nose into his crotch while I scooted my body forward. Applying full suction, I slowly withdrew. I half laughed at the slurping sound as he slipped from my lips. Both of us smiled as I hooked my hands under his knees. I lined my lubed cock up with his asshole and angled forward, pressing the head of my dick against the entrance to his ass.
"You ready?" I asked.
"Hell yes," Greg whispered.
I went into coach mode. "What are you going to do to take my dick more easily?"
"Push out," he said, "like I'm taking a dump."
I locked eyes with him. I nodded. "You can also do the opposite," I said. Greg seemed confused.
"Who controls your ass muscles?" I asked.
He nodded as he processed my question. "I do," he said.
"Can you clench them?" I asked.
He nodded again.
"Just keep that in mind, okay? When you want to loosen up to reduce pressure, push out. When you want to tighten up, clench down on me. It's probably going to hurt at first, but after a while the pain turns into pleasure. You sure you're ready?"
Greg reached up to grab the back of my head, pulling me in for a kiss. I guess that meant "yes." I know it meant that my cock moved forward against his ass. I could feel my head press into his pucker, pushing but not penetrating. I debated whether I wanted to be French kissing him while I breached his entrance or whether it would be better to be more upright, increasing my leverage and allowing me to witness the loss of his virginity. After our tongues danced in his mouth, I pulled away from his lips, rose upward, and planted my palms on the undersides of his knees. This freed up Greg's hands,which fell to his sides and instinctively gripped the bedsheets.
I looked down to see the head of my cock nudging Greg's ass lips, both of us glistening with lube. I pressed forward a bit. He was still closed tight. I pressed forward more. Still, no progress. I made eye contact with Greg. "I'm going to count to three. On three, I want you to push out like we practiced. Okay?" He nodded. I could see the nervousness in his eyes. Then I directed my gaze back toward his ass. It really was magnificent: hairy and muscular, it occupied the south side of my favorite neighborhood, just below his balls and an erection pointing true north.
"One," I said, pressing forward a bit more. "Two," I said, pushing harder. I waited a moment. I wanted both of us to remember this. Then: "Three!" Greg's abs contracted and his sphincter bloomed open just enough for me to enjoy the sight and the sensation of my cock breaching the entrance to his ass. As I registered the tightness and heat I looked up toward Greg's face, just in time to see his eyes roll back. His jaw dropped open as his head fell backwards onto the mattress, causing his adams' apple to to bulge out alongside the chords of muscle on his neck.
I held still for a moment. "You did it, buddy. You okay?"
Greg, who had been holding his breath, exhaled. "It feels intense," he rasped, "but I can take it."
"I know you can," I smiled. "You already are."
I pushed forward another inch, leaning in to kiss him. As my tongue swirled inside his mouth I circled my hips to swirl the first two inches of my dick inside his ass. I could feel him begin to loosen up. I pressed forward some more. Greg moaned into my mouth. But still he was kissing me. I began to saw in and out of him. He was still tight, but loosening, and very hot and very wet. A minute later, after a slow but steady descent down his chute, I felt myself bottom out.
At first I held still, allowing him to get used to the feeling of having all of me inside of him. At this point our lips were gently touching but we weren't really kissing. Instead, we were staring intensely into each other's eyes. As Greg's ass relaxed just a bit, I watched his pupils dilate. I took this as a sign that he was ready for more. I slowly withdrew until I could feel the helmet of my cock pull back against his sphincter muscle. Then I slowly pressed back into him, bottoming out. As I repeated this process, I gradually picked up steam. As I fucked him his hands unclenched the bedsheets and made their way to my back. I felt his palms raking up and down my spine. His fingers dug into my shoulder blades as his ass started to buck against me, meeting my thrusts to intensify the sensations. I winced as his fingernails dug into my back.
My tongue extended to scrape against the stubble at the base of his chin. "Fuuuuck!" he sighed, grinding his ass onto my cock. I could feel his dick grazing against my abs, twitching in its desperation for sustained contact.
My plan all along was to fuck the cum out of Greg. I wanted him to experience his first anal orgasm. And now, as I thrust in and out, sweating and panting onto him, I grazed the head of my cock against the nub of his prostate. But as I continued my communion with his insides, as I repeated the teasing of his chute, as I felt myself getting closer and closer to the point of no return, I pulled out just far enough so that the heat and wetness of his ass continued to embrace the head of my cock.
This exposed my own asshole. I reached for the lube and coated my finger, which I quickly shoved into my sheath. As I fingered myself the suspicion that a good fucking could make me cum quickly turned into a certainty.
I pressed my mouth to Greg's and this time allowed his tongue to work its way between his own lips. I climbed over his thighs, grabbed his cock, and angled it to press against my hole. I sat down -- immediately feeling pain as my clench rebuffed his attempt to penetrate.
That's when Greg read my mind. "Push out," he said. The student was now the coach. I did as he instructed. A split second later, he pressed in. This time my own jaw dropped. Holy shit! Greg, to me, was many great things. At this point, however, the only thing that mattered was his hard, thick cock. I forced myself down on him. I couldn't get enough. And even if I had wanted to slow things down, Greg, who was bucking into me, was in no mood to hold back. I'd been fucked before, but never like this.
The consummate wrestler, of course Greg didn't hesitate to maneuver into a more advantageous position. He flipped me onto my back. He leaned down to kiss me and then to suck and bite my neck. There was little thought involved. He was rutting up against me. Our sex had turned primal, wanton. I felt him lower himself onto me as the force of his thrusts increased. My hands embraced the slickness of his sweaty back. His treasure trailed danced against the underside of my erection. I did my best to press up into him. I felt the heat and moisture of his body, the musculature of his hairy ass, the scrape of his teeth against the sensitive skin of my ear. I inhaled the moist heat of his body. I tasted the salt of his sweat.
That's when I crested the wave. I convulsed and unleashed. I spewed and I clenched. As my cock started to shoot my ass muscles tightened around Greg's shaft. That's when I heard him breathe in sharply. I could feel him shoot. There was the first, long ejaculation. He clutched my body and sort of whimpered. He thrust into me a split second later, grunting again. And then again. And again. I was surprised to be able to feel the volume of his cum. Never before had I been with a guy and felt his load leaking from around his dick to trickle over the tight ring of my ass.
Greg collapsed on top of me. "Stay in me," I panted. "Don't pull out." I didn't want to break the connection. Neither, it seemed, did he.
When eventually his cock softened and gently slipped from my ass, he rolled to his side. He looked amazing. His muscles were pumped and his skin was flush. He was glistening with sweat and -- on his abs and around his pubes -- cum.
Greg and I showered together and then dried each other off. We went out onto the deck naked to grill our dinner. By this point it was totally dark -- and certainly fairly private. After dinner we fucked again. This time he took the lead. But this time I finished by breeding him.
The sex continued for the remainder of the academic year. Even after Greg graduated, we remained close. He visited once when my wife was away. When he came home on R and R from one of his deployments, I flew out to see him. We shared a room -- and some hot times -- during my cousin's bachelor party weekend. My wife was present for the wedding, but that didn't stop us from finding time to be alone. and wedding weekends. Even now, more than a decade afterwards, we remain in touch.
I still live in Annapolis. Greg has risen through the ranks and is now a commander in the U.S. Navy. He's been deployed just about everywhere but will soon return to USNA to help take charge of the wrestling program.
When he phoned a couple of weeks ago, I asked the obvious question. "Can I still be your coach?"
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