Naval Academy Wrestler

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 trail 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. 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?"