Anal Appointment with Derek Thompson
I’d barely slept the night before. My sheets were twisted, my dick hard half the night, my brain replaying the taste of Derek’s cock over and over again. Twelve years of crushing on him, and now I was counting down hours like I was waiting for Christmas. Only this wasn’t Christmas. This was Derek. Coming back. For me….For my hole.
By the time Saturday rolled around, I’d already showered twice. I must have rearranged the room three times - fresh sheets on the massage table, candles, even wiped down every corner like I was prepping for a damn inspection. My heart was pounding with every sound outside, each car passing making me think, that’s him.
And there it was.
That knock. Heavy, confident. Not just a knock, but the kind that said I’m here. Be ready.
I froze for a second, heart hammering, then rushed to the door.
It was him. Derek, standing in all his glory. Black compression t-shirt that looked painted onto his chest, short athletic mesh shorts riding high on his thick, muscled quads. His whole body carried that gym-fresh heat, the kind of presence that filled a room before he even stepped in.
In his hand, a different bag this time. I knew without asking it wasn’t full of creams and stretching bands; it was packed with towels and massage oils. I thought to myself, are we seriously still pretending this meet up is for an actual massage? I might as well have booked it on the app as “massage,” but let’s be real, I should’ve just written Dick Appointment.
“Hey! Dan… Daniel!” he said, grinning wide. That smirk of his sat cocky on his lips, the kind of smirk that whispered, yeah, I’m about to ruin that hole.
“Hi, Derek!” I said quickly, stepping back to let him in. “How was your week?”
He walked inside, setting the bag down by the massage table. “Good, man. Stressful. Work, clients, training. Been carrying all this pent-up energy around.”
I smirked, glancing at the table. “Mhmm, same here. I’m sure the massage will help today.”
He gave me a look like he saw right through me. “Third appointment in one week, huh?” That smirk tugged higher as he tugged his shirt over his head. No explanation this time. He didn’t bother pretending the room was hot or that he needed to “move freely.” He just stripped.
The compression shirt hit the chair, then the mesh shorts. He was left in red Calvin Klein briefs; tight, smooth, almost silky. The kind of underwear gym bros wear when they know someone’s going to see them. His bulge pressed out shamelessly, the fabric cupping him so well it was impossible not to stare.
He stood near the table, cocky as hell. “Guess this one’s not going to be professional anymore.”
I swallowed, heat crawling up my neck. One by one I stripped off my own clothes until my cock dangled free between my legs. Then I climbed onto the table, laying flat on my stomach, my ass pushed up just enough to show him what I was ready for. “The first two weren’t exactly professional either,” I muttered into the sheet, grinning.
His warm, heavy hands landed on my back, pressing slow, teasing strokes down my shoulders. He kneaded me like he was easing tension, laughing low in his chest. “Relax, man,” he said mockingly. “I was being professional. Just gave you a happy ending.”
The way his palms pressed into me, strong and sure, made my muscles melt. My body loosened under his weight, his hands spreading heat across every inch of my back, down toward my hips.
“So…” I breathed, half into the pillow. “You aren’t going to be professional tonight?”
His hand slid down the curve of my back, deliberate, heavy, until his palm cupped my ass. A squeeze, hard enough to make me lift my head from the pillow with a gasp. Then—smack. The sound cracked through the quiet room, my ass jiggling under his hand.
Another spank. Harder. My cheeks burned.
“Is this professional enough?” Derek’s voice dripped with dark amusement as both his hands kneaded and spanked my ass like it was his personal stress toy. His grip swallowed me up, fingers sinking into my flesh, spreading me open.
“Uhmm… no…” I laughed breathlessly, still sprawled on the table, my cock dragging against the sheets with every squeeze. “I don’t think that’s very professional of you… Mr. Brady.” I put weight on his last name just to tease, glancing over my shoulder with a grin.
His answer came in the form of fingers gliding into my crack. Slow. Teasing. Not quite on my hole, but dangerously close just ghosting around the edges, pressing against the tight rim without slipping inside. My whole body clenched up in anticipation.
“So, I won’t be professional then,” he said, voice low and thick. The way he said it left no room for doubt; he was here to ruin my hole.
“Mmmhh fuck,” I moaned, my hips twitching against the table. My cock rubbed hard against the sheets, leaking.
Derek shifted, stepping down near the foot of the table. His hands never left me, still spreading, squeezing, holding my ass like he was getting familiar with it all over again. Then I felt his body slotting closer; his chest brushing against the insides of my thighs, his shoulders forcing them wider apart. His breath hit the backs of my legs, warm, wet, sending shivers straight up my spine.
Then...closer. The heat of his mouth hovered over me, every exhale washing across my ass. My toes curled.
“I don’t… remember booking this appointment as a booty massag—e” I tried to joke, but the words fell apart into a raw moan, “—aauhhhh oh holy f-fuck…”
His tongue. Wet and slow, dragging across one cheek, then straight through my crack. A line of heat and slickness that stole my breath. He licked me like he was tasting something he’d been starving for, flattening his tongue, pressing deep.
“Fuuuckk, Derek,” I moaned into the pillow, my body arching back into him without even thinking. My ass pushed back, grinding against his face, needy for more.
He answered by diving deeper. His nose buried itself between my cheeks, pressed firm against me while his tongue flicked over my hole, teasing, circling, then flattening hard against it. He moaned into me like my ass was feeding him, his breath going hot and wet.
I gripped the edge of the massage table until my knuckles went white. Every drag of his tongue made me twitch. Every flick over my rim had me panting like I was already about to cum.
He spread me wider with both hands, his thumbs pulling me open so his tongue could work me raw. Long, slow licks up and down my ass crack. Sharp flicks directly against my hole. Then pressing, pushing, grinding his tongue harder against the tight rim until it gave just a little.
“Jesus fucking Christ,” I gasped, my voice breaking. My hips bucked against the table, cock sliding in slick pre-cum mess. I couldn’t stop rocking between the friction below and his mouth working me open from behind.
“Eat me, Derek… fuck, don’t stop… eat my fucking hole,” I begged, voice muffled into the sheets, throat raw with need.
He growled into me, the sound vibrating through my ass, sending sparks up my spine. Then he alternated, tongue flicking fast against my hole, then plunging deeper, then dragging out in one long, filthy lick that left me shaking.
I pressed back against him, shameless. My ass grinding against his mouth, nose buried so deep I could feel his stubble scraping me raw in the filthiest way.
Derek’s tongue drove deeper, hot and insistent, the slick muscle spearing into me. I moaned into the sheets, drool spilling from my open mouth as his spit was leaking down over my hole, making everything wetter, filthier. He spit directly on me, a hot strand splattering, then licked it all back up before shoving his tongue inside again, grinding his face deeper into my ass like he couldn’t get enough. The obscene sounds filled the room; slurping, gasping, my shameless moans blending with his growls.
My body jerked every time his tongue stabbed in, the tip finding spots that made my toes curl. His nose rubbed against me, his stubble rasping in the rawest way, a dirty burn that only made me want more.
His tongue was ruthless, plunging and twisting, spit dripping down my crack as he tongue-fucked me open. Every thrust sent me clawing at the sheets, muffled moans spilling from my throat. “Fuuuck, Derek… deeper… please,” I begged, my voice cracking.
He groaned into my hole, the sound vibrating straight through my body, like he loved the taste of me too much to stop. His stubble burned raw against my rim every time he dragged his tongue out, only to shove it back in, sloppy and hungry. My ass was slick, messy, dripping with him.
Then his hands moved. From gripping my hips so hard I’d bruise, they slid away, and I heard it; the faint stretch of elastic, fabric being tugged down thick thighs. My chest heaved, anticipation choking me as I felt his tongue press one last filthy thrust into me before he pulled back just enough to breathe.
“Fuck, your ass tastes so good,” he rasped, his voice shredded with lust. I moaned into the table, hole clenching at his words, at the sound of fabric hitting the floor with a careless toss.
The next second, his weight shifted over me, heavy and dominant, pinning me down. His chest slid against my back, damp with sweat, his heat sinking into me until I couldn’t move. My whole body trembled under him.
And then I felt it. His cock, thick and hot, slapping against my saliva dripping ass. Heavy, blunt, teasing. My mouth fell open on a ragged gasp.
He buried his face against my ear, breath hot and filthy. “You ready for some prostate massage now?” he whispered, voice low, moaning the words like a threat and a promise.
My eyes fluttered shut. “Mhmm… yes…” I breathed, voice breaking into a needy whimper.
Derek’s tongue left my hole wet and trembling. I felt the blunt weight of his cock slide between my cheeks, hot and wet from all the spit he’d worked into me. He groaned low, dragging the thick length up and down, smearing the mess across my crack, teasing my hole with every lazy stroke.
“Fuuuck…Derek” I moaned, my hips rocking back against him without even thinking. Each pass left me aching, desperate, his cock heavy like it belonged there, like my ass was made to hold it.
He pressed harder, letting the fat head nudge against me, not pushing in yet, just grinding, smearing himself in my spit until my hole was slippery and swollen. His voice broke the tension, rough and amused in my ear.
“Damn bro,” he muttered, rutting between my cheeks, letting the head bump my entrance again and again. “All that spit… coated my cock like lube. You’re ready for it, huh?”
I whined, barely able to form words. “Fuck Yes...Please…”
He didn’t wait anymore. No more teasing my hole with that fat cock. With one steady push, he lined up and shoved, the blunt crown forcing my hole to open. The first inch of his eight-inch cock stretched me wide, my lips parting in a ragged cry that melted into a groan.
“Uhhh—fuck, Derek—” My fingers dug into the edge of the table, body shaking at the intrusion.
“Fuck yeah, take it,” he growled, pressing forward, sinking deeper.
My back arched as he split me open inch by inch, every thrust burning, filling, lighting me up from the inside. The thick friction made me gasp and moan into the sheet, my cock grinding helplessly against it, smearing pre-cum into the fabric. The table creaked under me as his weight drove me down, his cock carving me open until I could feel all of him inside, heavy and throbbing.
He inserted his 8-inch cock all the way in until there was nothing left to give, his hips flush against my ass, his cock buried to the base, thick and throbbing deep inside me. The stretch was overwhelming, my hole clenching around the heat of him, every nerve sparking. His groan rumbled against my neck as his chest pressed down on my back, and I shook under the weight of him, stuffed full, owned.
“Unghhh—uhhh ffffuck—” I couldn’t even form words.
“Yeah, that’s it. Feel me. All the way in your guts.” His teeth grazed my shoulder, a low growl vibrating through me.
He pulled back slowly, then slammed back in, the massage table creaking beneath us. The sound of skin slapping skin filled the room, sharp and filthy. My moans grew louder with every thrust.
“Ahhh—ahhh fuck, fuuuckk—”
He set a brutal rhythm, hips snapping forward, cock pounding deep into my prostate. Every slam had my vision flashing white. The table rocked under us, my hands clutching the edge like I’d fly off otherwise.
“Uhhh fuckk… Derek… uhh ffffuck me harder—”
“Shut up and take it slut,” he groaned.
I let out another moan, shameless and needy, but he cut it off by shoving two thick fingers between my lips. I gagged instantly, throat straining as he pushed deeper, stuffing my mouth until spit leaked out around them, dripping down my chin. My muffled moans vibrated against his fingers while he slammed into me, each brutal thrust knocking more drool loose, my jaw stretched wide around the taste of his skin.
He pulled them free with a wet pop, strings of spit breaking as he slid his hand down to my hips. His grip clamped hard, fingers digging into my flesh as he pried me open wider for his cock. I cried out, the sound filthy, porn-like, turning my head back toward him with my lips slick and swollen. “Unngh… Derek…”
He leaned forward until his mouth caught mine, swallowing that moan in a hungry kiss. His lips pressed hard, messy, and his tongue pushed deep, not asking but taking, exploring, tasting the spit he’d just pulled out of me. His breath was hot, his stubble scraping my skin, his mouth claiming mine like he couldn’t get enough. I kissed back desperately, clutching at the edge of the table as his cock drove deeper, every movement making the kiss wetter, needier and filthier.
I moaned into his mouth and he swallowed it, grunting into me as his thrusts grew rougher. His lips didn’t just press against mine, they devoured. Wet, greedy, almost brutal. His tongue shoved past mine, swirling, sucking, pulling me into him until the kiss became another kind of fuck. Every time his hips slammed forward, his cock burying deeper, his tongue mirrored the rhythm inside my mouth, filling me, gagging me with heat and spit. I was choking on him in two places at once, lost in the dizzy blur of pleasure and pressure.
His teeth scraped my lower lip, biting hard enough to sting, then sucking the hurt away in a messy drag. Our spit slicked both our chins, drool running hot down my cheek. He kissed me like I wasn’t supposed to breathe, like oxygen was his to control, like he wanted me to drown in him. Every gasp I managed, he stole right back, swallowing my voice until all I had left were muffled whimpers vibrating into his mouth.
He pulled back for a second, just an inch, letting a strand of spit hang between us before slamming his tongue back into me, swallowing me whole again. I shuddered at the rawness of it, his beard scratching my skin, his breath burning against my lips. My whole face was wet, sloppy from the relentless kissing, but I didn’t care. I wanted more of it, all of it.
And his cock.. Holy fuck. He drove into me with the same hunger, pounding harder now, hips smacking against my ass with a meaty crack that echoed in the room.
Each thrust slammed me flat into the table, wood creaking, my body bending under his weight. His hand slid up my chest, fingers curling around my throat, squeezing lightly while he shoved his tongue deeper into my mouth, groaning into me like an animal. My throat vibrated with his moans, my chest burning with every held breath, but I only pushed back harder, begging for more with every filthy sound I made into his kiss.
He angled his hips suddenly, finding that spot inside me that made my vision burst white. My moan broke against his lips, high-pitched, desperate, the sound instantly swallowed by his mouth as he kept me pinned there. His cock hammered that same place over and over, merciless, precise, until my legs shook uncontrollably.
I clung to the edge of the table, knuckles white, as his hand left my throat and grabbed my jaw instead, forcing my mouth wider for another messy, devouring kiss. I tasted him, myself, the spit we’d traded. His tongue dominated mine, curling and plunging, dragging me into the filth of it until I didn’t know if I was being kissed or fucked harder. Both, maybe. My lips were swollen, my throat raw, but he never slowed, never gave me a chance to recover.
My body shook under him, every muscle stretched tight, hole clenching around his cock like it couldn’t decide if it wanted to hold him in or push him out. He groaned against my tongue, biting my lip again before shoving back deep, his chest pressing harder into my back, sweat dripping down his forehead to smear against mine. I was pinned under him, consumed, every thrust and every kiss branding me.
And then...fuck. The table jolted under us as he picked up the pace, fucking me rougher, deeper, harder. Our mouths broke apart for half a second, both of us panting, spit strings still tethering our lips. Then he yanked my face back to his, growling low as his cock bottomed out again and again.
“Fuck fuck fuck.. Daniel. You fucking whore”
My cock dragged against the table with every slam, the friction pushing me closer, precum streaking the sheet. I was about to cum just from this, just from him destroying my hole and grinding my cock raw into the table.
“Unghhh—ahhh Derek, I’m—fuckk I’m gonna—”
“Cum,” he snarled, hips pistoning. “Cum while I breed this tight ass.”
His mouth dropped to my ear, hot and wet, his teeth sinking gently into the lobe, then nibbling. I cried out, the sensation ripping through me, my whole body convulsing.
“Uhhhhh—ahhhh—fffuuuuuuckkkk—”
I exploded against the table, cum shooting in hot streaks onto the sheet, my cock jerking against the surface while Derek never slowed. He fucked me through it, harder, rougher, each thrust pounding cum out of me, my body going limp under him.
The table rocked, my cheek pressed into the soaked sheet, his teeth still on my ear, his cock still buried and driving deep, chasing his own release.
“Gonna fill you, gonna breed you,” he whispered into my ear, his thrusts erratic now, desperate.
“Do it,” I whimpered, still twitching. “Fffill me, Derek—fuck, please—”
He slammed in deep, held, and let out a guttural moan that shook through my chest. Hot, thick pulses of his cum spilled inside me, his cock throbbing as he emptied himself in my hole. I felt it flooding me, spilling over, warmth stretching deeper with every twitch of his shaft. He ground his hips into me, shoving every drop further, like he wanted to brand me from the inside. His teeth dragged across my ear one last time as he came, his growl breaking into a long, helpless groan.
The table creaked under us as I shuddered, my body clenching around him, milking him. I could feel it leaking already, wet warmth dripping down my crack, sliding onto the table. He groaned again, quieter this time, softer, almost satisfied. Then finally, after one more push of his hips, he pulled out slow. The loss made me whimper.
I stayed bent over, destroyed, as he stepped back. His cock slipped free with a wet sound, cum immediately spilling from my hole, running hot between my cheeks, down my thighs. It felt like a weight had been lifted, quite literally. My body was trembling, sweat slick across my skin, my ass stretched and ruined, dripping. I looked up through the haze, watching him move toward the head of the table where my face was.
Derek loomed there, chest still heaving, his cock hanging heavy in front of me, half-hard, glistening with our mess. Pearls of cum slid down the shaft, gathering at the fat tip, threatening to drop. He gave me a look that was nothing but raw ownership. Then he held it closer, smirking.
“Clean it.”
My lips parted immediately. I opened up, tongue sliding under his cockhead, catching the cum dripping there. It was hot, salty, musky. I swallowed around him, licking down the underside, careful, obedient, pulling the mess from his slit until he gleamed again. When I pulled back, lips wet, his eyes burned into me.
“Fucking slut,” Derek muttered, almost to himself.
I flushed at the word, shivering. He didn’t linger. He stepped back, grabbed his underwear, pulling them on lazily. Shorts next. He threw his t-shirt over his shoulder instead of wearing it, his body still shining with sweat. Casual, like he hadn’t just fucked me senseless.
“Best massage client ever,” he said, smirking as he glanced at me sprawled there.
I laughed weakly, collapsing onto my back now, too spent to move much. “Best masseur ever,” I croaked, voice rough and shaky.
He looked at me like he owned that answer, and started toward the door.
“So do I still need to book you through the app, or…?” I asked, half-joking, half-serious, my voice quieter now.
Derek stopped, gave me a grin over his shoulder. “Hahaa..Just text me… when you want your pussy fucked but book through the app when you actually want a massage.” Then he left, door closing behind him like nothing happened.
I stayed there on the table, wrecked, my mouth still wet, the taste of his cum heavy on my tongue. My throat burned with it, my ass still dripping onto the sheet, more cum cooling on my thighs where it had leaked out. My body buzzed...wrecked, sweaty, marked all over.
Finally, after years of crushing on that jock, years of sneaking glances, wondering, fantasizing, I’d had him. And he’d fucked me like he’d known what I wanted all along.
I stared at the ceiling, a stupid smile tugging at my lips. My body was ruined, but my mind wouldn’t stop spinning. Derek’s hands had gotten me here, from the first touch to the last grip on my hips.
Yeah, the jock’s hands really did have magic. And it wasn’t just for the massage.
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