Virginity Sold, Ass Destroyed

Soft curves, doe eyes, thick ass—I thought $1000 was easy money. The buyer had other plans: total ownership and a ruined, cum-filled hole.

My stomach twisted into knots the moment my parents slammed the door behind me, their shouts still echoing in my ears. Eighteen years old, and suddenly homeless because they couldn’t handle the way I looked, the way I moved, the secret little life I’d tried to keep hidden. The suitcase in my hand felt heavier than it should have, stuffed with the only clothes I owned and the last of my savings—barely enough for a cheap motel room for two nights. No job, no friends willing to take in a boy who got mistaken for a girl every time he stepped outside. I needed money, fast, or I’d be sleeping on the street by the weekend.

That night, alone in the dim motel room, I stared at my reflection in the cracked mirror. My face was soft and delicate, with those wide, doe-like brown eyes framed by long lashes, a slender nose that turned up just slightly at the tip, and full, plush lips that always looked a little swollen. Shoulder-length hair fell in silky waves around my cheeks, the color a warm chestnut that caught the light. My skin had that smooth, tan-white glow, completely hairless after years of careful shaving. At five-foot-seven and sixty-five kilos, the extra softness had settled everywhere it counted—my chest carried two gentle, rounded swells that pressed against my shirt like a girl’s budding breasts, my hips curved out in a wide, inviting sway, my thighs plush and thick enough to rub together when I walked. And my ass… God, it was thick and chunky, two heavy cheeks that jiggled with every step, full and bouncy, the kind of rear that drew stares even when I wore baggy jeans.

Between my legs hung my circumcised five-and-a-half-inch cock, already half-hard from nerves, with a plump, heavy sack swinging beneath it. Even dressed in plain boy clothes, strangers still called me “miss” half the time. I used to love that secret thrill. Tonight, it was going to pay the bills.

I opened my laptop and typed the ad with shaking fingers: “Passably feminine 18-year-old gay boy selling his anal virginity. One thousand dollars, cash only. Clean, discreet, serious inquiries only.” I attached a couple of tasteful photos—me from the neck down in tight underwear, showing off the curve of my hips and the plump swell of my rear, face blurred just enough. Then I hit post on the site and waited.

Replies flooded in within the first hour. Some were crude, some were pushy old men offering half the money. I scrolled past the gym-rat types and the aggressive ones. My eyes landed on one profile that looked… safe. The guy’s photo showed a plain, unattractive man in his mid-forties—balding on top, a little chubby around the middle, thick glasses, a weak chin, and a hesitant smile. His message was short and polite: “I’ll be gentle with you. Just want to make it good for your first time. Can meet tonight at my place. Cash ready.” He sent a face pic and a dick pic—nothing special in the looks department, but the cock in the second photo made my breath catch: thick, veiny, easily nine inches even soft. Still, his meek expression sold me. He seemed harmless. Perfect.

We arranged it for nine o’clock. I showered, shaved everything smooth again, slipped into my tightest jeans that hugged my chunky ass like a second skin and a loose hoodie that hid the soft little mounds on my chest. The bus ride to his apartment felt endless. My heart hammered the whole way.

He opened the door in a faded t-shirt and sweatpants, exactly as plain as his picture—pale skin, thinning hair, a soft belly. “Come in,” he said quietly, stepping aside. The apartment was small, dimly lit, smelling faintly of takeout. He handed me the envelope of cash right away, counting it out on the coffee table like a gentleman. “One thousand, as promised.”

I pocketed it, nerves making my voice soft. “Thank you.”

He looked me up and down, eyes lingering on the way my jeans stretched across my wide hips and the thick swell of my rear. “You’re even softer in person,” he murmured. “Those pictures didn’t do you justice, pretty thing.”

The compliment made me blush. I started to relax—until his hand suddenly gripped my chin, tilting my face up. The meek smile was gone. His eyes had turned hard, hungry. “Strip. Now.”

I blinked. “Wh-what?”

His fingers tightened. “You heard me, slut. Clothes off. I paid for that virgin hole, and I’m not waiting.”

My hands trembled as I peeled off the hoodie, then the jeans, standing there in just my plain briefs. My soft chest rose and fell quickly, the little rounded swells on full display, nipples already pebbled. My thick thighs pressed together, and my chunky ass cheeks wobbled slightly as I shifted my weight. My cock twitched inside the fabric, half-hard despite the fear.

He circled me slowly, like a buyer inspecting goods. One rough hand grabbed my left breast, squeezing the soft, girlish mound, rolling the nipple between thick fingers until I gasped. “Look at these pathetic little tits. You really are built like a cheap whore.” His other hand dropped to my ass, palming one heavy cheek, kneading the plush flesh hard enough to leave red marks. He spread me open through the briefs, thumb pressing against my tight pucker. “And this fat ass… jiggling like it was made for cock. Turn around.”

I obeyed, bending slightly as he yanked my briefs down. My five-and-a-half-inch cock sprang free, bobbing in front of me, my full balls hanging heavy. He laughed, low and cruel. “Oh, what’s this? A tiny little dick on such a girly body? Cute clitty, but it doesn’t belong here. You’re supposed to be a hole, not a boy.” His palm slapped my cock lightly, making it bounce. “Pathetic. Keep it out of the way while I use what I paid for.”

Humiliation burned in my cheeks, but my cock betrayed me, twitching harder. He shoved me to my knees right there in the living room. His sweatpants came down, and that nine-inch monster flopped out—thick as my wrist, veined, the head already leaking. The balls beneath were heavy and hairy, swinging low. “Worship it, bitch. Show me how grateful you are.”

I leaned in, lips parting. My tongue traced the thick underside first, licking slow, wet stripes from base to tip, tasting the salty musk. I cupped those heavy balls, rolling them gently, sucking one into my mouth, then the other, swirling my tongue around the wrinkled skin while my hand stroked the massive shaft. He groaned, grabbing my hair. “That’s it, suck on Daddy’s balls like the desperate little cocksleeve you are.” I moved up, wrapping my pouty lips around the head, sucking hard, tongue flicking the slit. Inch by inch I took him deeper, cheeks hollowing, until the head hit the back of my throat. I gagged instantly, eyes watering, but he held my head down. “Deeper, whore. Choke on it. Cry for me.”

Tears spilled down my cheeks as I forced myself further, throat convulsing around the thick invasion. Saliva drooled from the corners of my mouth, dripping onto my soft chest. He thrust gently at first, then harder, fucking my face with short, brutal strokes. “Look at you, gagging like a cheap whore. Those big brown eyes look so pretty when they’re watering.” My nose pressed into his pubes on every push, air cut off, chest heaving. I cried openly now, mascara I’d secretly applied running in black streaks, but I kept sucking, hollowing my cheeks, worshipping every veiny inch.

He pulled out suddenly, strings of spit connecting my lips to his glistening cock. “Enough. On the bed. I want that virgin ass.”

He dragged me to the bedroom, a plain mattress on the floor. I crawled onto it on all fours, ass up. His hands roamed again, groping my thick thighs, kneading the plush flesh of my cheeks until they turned pink. “Fuck, this ass is obscene. So fat and bouncy.” He spread my cheeks wide, thumbs digging into the soft skin, and leaned in. His tongue dragged hot and wet across my tight hole, circling the rim, pushing inside in lewd, slurping licks. I moaned, face buried in the sheets, my own cock leaking onto the mattress. He ate me out like a starving man, tongue fucking deep, spit running down my balls. Then came the spanking—hard, open-palmed smacks that made my chunky cheeks ripple and sting. “Count them, slut.”

“One… two… ah!” Each slap echoed, my ass jiggling wildly, skin turning bright red. Tears flowed again from the sting and the overwhelming shame.

Finally he knelt behind me, cock slick from my spit. “Time to ruin you.” He pressed the fat head against my virgin entrance, rubbing it in circles, smearing pre-cum. “Beg for it.”

“Please… fuck me,” I whispered, voice breaking.

He pushed. The stretch was brutal—my tight ring burning as the thick head forced its way inside. I cried out, fingers clawing the sheets, but he kept going, inch after veiny inch splitting me open. “So fucking tight. Your boy-pussy is swallowing me like it was born for this.” Halfway in, he paused, letting me feel every ridge, every pulse. Then he slammed the rest home in one brutal thrust, balls slapping my own. Pain exploded through me, but underneath it, a deep, shameful fullness. My cock throbbed untouched, leaking steadily.

He started moving—slow at first, then faster, hips slapping against my reddened ass. The angle had my face pressed into the mattress, ass up high, legs spread wide, his hands gripping my plush hips so hard the flesh overflowed his fingers. Every thrust dragged across something inside me that made sparks shoot up my spine. I sobbed into the sheets, body rocking, my soft chest squished beneath me, chunky ass rippling with each impact. “Take it, you girly little bitch. This is what you sold your hole for.” His balls slapped rhythmically against mine, heavy and full.

He pulled out suddenly, flipping me onto my back. My legs were shoved up and back until my knees nearly touched my shoulders, my thick thighs folded against my soft chest, chunky ass tilted up obscenely. He knelt between my spread legs, cock aimed straight down. The new angle let him sink even deeper, the head grinding against that spot inside with every plunge. My eyes rolled back, tears streaming, mouth open in constant moans mixed with sobs. He leaned over me, one hand pinning my wrists above my head, the other slapping my soft little chest, pinching the rounded swells. “Look at these pathetic tits bouncing while I wreck your cunt. You’re not a boy—you’re my fucktoy.”

The pace turned savage. His hips hammered down, the wet slap of skin filling the room, my virgin hole stretched wide around his nine-inch girth, gripping him like a vice. I could feel every vein, every ridge dragging in and out, my insides molding to his shape. My own cock bounced on my belly, untouched, smearing pre-cum across the soft skin. He spat on my face, then slapped my cheek. “Cry harder, slut. I love how your pretty eyes look when you’re getting ruined.”

I was lost in it—pain, pleasure, humiliation all blending into one overwhelming wave. My body shook, ass clenching around him, the thick cheeks quivering every time he bottomed out.

His thrusts never faltered even as he leaned closer, hot breath washing over my tear-streaked face. “Look at you, shaking like a leaf with that soft, plush body of yours giving in so easily,” he growled, one thick hand sliding up to pinch the gentle swell of my left chest mound hard enough to make me yelp. The rounded, feminine curve jiggled under his fingers, the sensitive peak twisting between them until fresh tears spilled from my wide brown eyes. “These delicate little tits bouncing every time I slam home—fuck, you really are built like the perfect fuckdoll.”

He kept pounding downward, the new angle grinding the fat head of his nine-inch cock relentlessly against that sensitive spot deep inside me, sending jolts of liquid fire through my belly. My own five-and-a-half-inch length lay stiff against my soft stomach, leaking steadily, untouched and ignored except when he reached down to flick it dismissively. “Even with this cute little thing dangling here, you’re nothing but a hole. A girly hole that sold itself for cash.” His palm cracked across my upturned cheek again, the impact making the heavy, rounded globe ripple and sting, the sound echoing off the bare walls.

After what felt like an eternity of that folded, legs-pinned position, he finally slowed, chest heaving. With a wet, obscene pop he dragged his massive length free, leaving my entrance fluttering and gaping, slick strands of spit and pre-cum bridging the gap. “On top now, slut. I want to watch that fat, bouncy rear clap while you do the work.”

My limbs trembled as I obeyed, swinging one plush thigh over his waist and planting both knees firmly on the mattress beside his hips. Facing him directly, I hovered above that glistening monster, my curvy hips tilted forward, the lush fullness of my rear hovering just above the thick head. My supple hands reached back, spreading my own reddened cheeks so the wide tip kissed my wrecked ring once more. Slowly, inch by torturous inch, I sank down. The stretch reignited every nerve, my inner walls yielding to the veiny girth until my heavy, jiggling cheeks finally rested flush against his pelvis, his balls nestled warm and heavy beneath me. The fullness was obscene, pressing outward against my soft belly, making my own cock twitch visibly.

“Ride it,” he ordered, slapping the side of my voluptuous hip. “Bounce that juicy ass like the desperate whore you are.”

I rose until only the head remained inside, then dropped hard, the wet slap of my thick rear meeting his lap filling the room. Up and down I moved, my shapely thighs flexing, the extra softness making everything quiver—my rounded chest mounds bouncing freely, my shoulder-length hair swaying around my delicate features. Each descent drove him impossibly deep, the angle letting the flared head kiss that same electric spot over and over. Tears streamed down my cheeks as I sobbed, pleasure twisting into something shameful and addictive. He reached up, groping both soft swells on my chest, kneading them roughly, thumbs flicking the peaks until they ached. “Fuck, these girlish tits look so pretty jiggling while you fuck yourself on me. Cry harder, princess—let me see those big doe eyes ruin your makeup.”

My pace quickened under his commands, ass cheeks clapping loudly, the heavy flesh rippling with every impact. He slapped my rear repeatedly, each crack sending fresh heat blooming across the already tender skin. Between bounces he made me lean forward so he could spit directly onto his shaft where it disappeared inside me, the extra slickness letting me take him even smoother. I felt every ridge, every pulse, my insides molded perfectly around his thickness.

After long minutes of that relentless riding, he gripped my lush hips and stopped my movement. “Turn around. I want to see that chunky rear from behind while you keep bouncing.”

I lifted off with a gasp, the sudden emptiness making my hole wink and leak. Rotating on shaky knees, I faced away now, back arched, hands braced on his thighs for balance. My voluptuous ass hovered once more before I guided him back in, sinking down reverse until my heavy cheeks spread wide around his base. The new orientation changed everything—the angle pressed him against a different wall inside me, deeper, more punishing. I leaned forward slightly, plush thighs spread, and began riding again, rising high so he could watch every inch slide out shiny with my juices, then slamming back so my rear clapped against his stomach.

“Goddamn, look at that fat ass swallow me whole,” he groaned, hands spreading my cheeks wider, thumbs digging into the soft flesh to expose the stretched ring gripping him. “So smooth and hairless, jiggling like jelly every time you drop. This is what you were made for.” He spanked upward this time, the angle letting his palm catch the underside of each heavy globe, making them bounce wildly. My sobs turned louder, body trembling, the constant stretch and the humiliating exposure pushing me closer to the edge without a single touch to my own leaking length.

He reached around, finally wrapping rough fingers around my five-and-a-half-inch cock, stroking it once, twice, then squeezing the full ballsack beneath. “Even this decent little prick looks ridiculous on such a soft, feminine body. Leaking like a girl in heat while a real cock wrecks you. Pathetic.” The mix of rough handling and cruel words made me cry out, hips stuttering in their rhythm.

Minutes blurred into a haze of slapping skin and my broken whimpers. Eventually he shoved me off again, the wet slide leaving me empty and clenching. “On your stomach now. Flat. I’m going to pin you down and finish what I started.”

I collapsed forward onto the mattress, legs straight and close together, my thick rear slightly raised by the natural arch of my lower back. The position pressed my soft chest mounds into the sheets, my delicate face turned to the side so he could see the tears still flowing from my large brown eyes. He climbed over me immediately, knees outside my thighs, and used one hand to guide his throbbing length back to my gaping entrance. With his full weight he pushed in, the angle completely different—straighter, deeper, pinning me utterly beneath him. My plush ass cheeks cushioned his hips as he bottomed out, the heavy balls resting against the back of my own sack.

He started slow, grinding in circles, letting me feel every inch lodged inside my soft, yielding body. Then the pace built—long, powerful strokes that drove me into the mattress, my voluptuous hips trapped, my chunky rear compressed and spread under his pelvis. Each thrust made my entire lower half jiggle, the extra softness amplifying every impact. He reached forward, grabbing a fistful of my shoulder-length hair and yanking my head back so my pouty lips parted in a constant moan-sob.

“Take it, you girly little bitch,” he snarled, free hand snaking under me to grope and knead my chest swells again, pinching the sensitive peaks until I screamed. “This smooth, curvy body was built to be ruined. That thick, bouncy ass clenching around me like it never wants me to leave.” His thrusts turned savage, the wet sounds of skin meeting skin obscene, my insides stretched to their limit around his nine-inch girth. The pressure on my prostate was constant now, forcing my own cock to leak in steady pulses onto the sheets beneath my soft belly.

He kept me there for what felt like forever, alternating between deep grinding and rapid pounding, spanking the sides of my trapped rear whenever he wanted to hear me cry louder. At one point he pulled almost all the way out just to slam back in, repeating the motion until my hole gaped openly between thrusts. “Look at that wrecked pussy,” he laughed cruelly. “So loose and sloppy already. But still gripping me like a good whore.”

My mind fractured under the onslaught—pain radiating from my stretched ring, pleasure exploding from every nerve inside, humiliation burning in my chest as he mocked my soft, feminine curves and the way my body betrayed me by pushing back for more. Fresh tears soaked the mattress. I was babbling incoherently, begging without words, my plush thighs trembling, my heavy ass rippling nonstop.

Finally his rhythm faltered. His breathing turned ragged against my ear. “Gonna fill you up, slut. Gonna pump this virgin hole full until it overflows.” One last brutal thrust buried him to the hilt, his heavy balls drawing tight. I felt the first hot pulse deep inside me, thick ropes of cum flooding my guts in powerful jets. He groaned long and low, grinding against my rear as spurt after spurt painted my insides white, the warmth spreading, the sheer volume making my soft belly feel bloated. Excess leaked out around his girth despite how tightly I was stretched, trickling down to coat my own full sack.

He stayed buried for long moments, twitching, letting every drop empty into me. Only then did he pull free with a wet, filthy sound, my ruined hole left gaping wide, cum bubbling out in thick white globs that ran down the backs of my plush thighs. He slapped my quivering cheek one final time. “Stay there. Let it drip. That’s what you earned with your thousand dollars.”

I lay there panting, body limp and trembling, tears still sliding from my wide doe eyes, the overwhelming fullness and emptiness warring inside me. My delicate features were a mess—hair tangled, lips swollen, cheeks flushed and streaked. The cash envelope waited on the coffee table, but every movement sent fresh aches through my wrecked rear and the soft curves he had claimed so completely.

After several minutes he stood, pulling on his sweatpants with a satisfied grunt. “Get dressed, whore. We’re done. You took it better than I expected for a first-timer, but that fat ass is ruined now.” His voice carried no gentleness, only the same cruel edge that had dominated every second.

Shakily I rose, cum still leaking down my smooth legs, my own untouched length softening against my thigh. I gathered my clothes in silence, the weight of the envelope in my hoodie pocket the only reminder of why I had come here. Every step toward the door sent jolts through my body, the thick, chunky rear he had destroyed throbbing with every movement. I didn’t look back. The door clicked shut behind me, the night air cool against my flushed, feminine skin, but the memory of his nine-inch cock and the way he had broken me so thoroughly would stay burned into every soft, yielding inch of me for days.