"How romantic. What changed your mind?" His voice was casual, but the tight grip of the hands squeezing my ass told a different story. He really wanted to know. Why does he care? My mind seemed sluggish, thoroughly distracted by the feel of his strong hands on me, and the wicked explorations of his tongue. Words tumbled from my mouth without thought.
"I caught my boyfriend with his room-mate." I tried to be matter-of-fact, but the pain of that discovery colored my voice, and his hands loosened, caressing my bruised flesh. "He was gay. No wonder he didn't... We never..." My voice trailed off. I'd loved him whole-heartedly, had planned to marry him, but he'd used me as a disguise, a shield between his true desires and the world's disapproval. He'd never really wanted me. The cold of that betrayal dissipated the warm cloud of physical pleasure I'd been floating on, and I shivered.
"So why the auction?" My buyer's next question drifted up from below and I almost laughed. Here I was, naked, with a stranger face-down between my legs, and now he wanted to talk. It was surreal. Somehow that made it easier to be honest.
"Money, of course." He slapped my ass in remonstrance to my off-handed tone, and I yelped, and then shrugged. "Well, what did you expect? I finished college but couldn't find work. I'm in graphic design, but nobody wanted my skills, not even free-lance. It seemed like the only value I had was between my legs." I tried to keep the bitterness out, without much success. I'd been on the edge of homelessness, but the real kicker had been when my family called... but he didn't need to know about that.
My brooding thoughts were lost as his hot tongue finally slid over my tender asshole, and I moaned as liquid heat flooded through me again, driving out the cold. "Maybe you should learn some new skills." His voice was muffled as he pressed his face against my ass. My biting rejoinder to this helpful bit of advice was lost as the pointed tip of his tongue gently probed my puckered ring. Wicked pleasure spread through me from that forbidden touch and I squirmed underneath him as he licked and teased my asshole. He gently stretched me with his tongue and then began to tease me with a finger, nudging against that virgin territory.
He shifted to kneel between my legs, one hand on the flat of my back pinning me to the bed. His fingertip slid gradually slid deeper into my ass as he rhythmically penetrated, each thrust sinking a bit further. A strange, stretchy pleasure began to spread through me, knotting in my belly, and I moaned, rocking my hips against his hand as his finger flexed deep inside of me. As the tight ring of my asshole loosened around him, he added a second finger, gently working it into my ass along-side the first.
My asshole burned as it was stretched, but once more the fiery pain transformed into a sharp-edged pleasure. I shoved harder against his hand as a desperate tension began to grow inside of me, panting for breath. He responded by thrusting more forcefully, sinking his fingers deeply into my ass with each gliding stroke. His free hand rubbed gentle circles on my back, a confusing bit of tenderness, even as his fingers sank roughly into my loosened asshole, shoved in as far as they'd go again and again, bruisingly deep. I quivered and shook under him as the muscles of my legs and belly tightened, clenching from the twisted pleasure filling me.
He suddenly pulled his fingers completely out of my ass, leaving me empty and moaning with need. Then he tugged on my hips, raising me to my knees before him. He pulled me back against him and I felt the broad head of his cock press the tight ring his fingers had loosened. His cock felt huge, much larger than the fingers it was attempting to replace, and I shuddered in sudden fear. "Try to relax, darling."
The firm head of his cock shoved against my asshole, the closed ring resisting the growing pressure until it painfully gave way. I gasped as the head of his cock suddenly sank into my ass, stretching the tender flesh as never before. The burning pain of his intrusion drowned any chance of pleasure, and I clawed at the sheets, panting. Ignoring my whimpers, he shoved his cock deeper into me, inch by inch, until he had fully sheathed his hard cock in my aching ass.
He paused there for a long moment, hands comfortingly rubbing my back as I sobbed for breath, nearly in tears from the searing pain. Gradually it faded into a dull ache, an uncomfortable feeling of fullness. I made a tentative motion to pull free of him, in the dim hope that he was done, but he chuckled, his hands on my hips holding me still. "We're not finished yet, darling."
He slowly slid his cock out of me, before sinking it deeply back into my ass. I clenched around him reflexively, and he shuddered, gasping. "Easy, darling." As he stroked in and out of my throbbing asshole, gradually gaining speed, the dull ache of his cock stretching me transformed into pleasure. Each thrust sent a wave of sharp-edged sensation through me, tension once again knotting in my core. It built more quickly this time, tightening my body around his pounding dick as I moaned and shoved my ass against him, urging him to fuck me harder.
He reached one arm around me, jamming a rough finger against my clit. I gasped as pure pleasure rippled out from that grinding contact. The coiling pleasure inside of me tightened even further, leaving me nearly crazed with desperation. He fucked me roughly, slamming his cock into me faster and faster, his finger on clit pulsing in time. I clawed at the sheets, moaning and panting, until one last thrust of his cock into my shuddering ass finally fractured the knotted tension inside of me.
I froze, gasping, as an intense wave of pleasure swept through me, wiping away all thought and reason, whiting out my mind. Rippling aftershocks followed that first surge, repeated lesser peaks that left me moaning, my legs and feet tingling in their wake. He groaned too as my ass clenched tightly around his cock with each surge, thrusting wildly into me as I quaked in the throes of my first orgasm. As the over-whelming pleasure faded into warm bliss, he stiffened over me, jerking and shaking, groaning as his swollen cock pumped its hot load deep inside my throbbing ass.
He leaned into me, panting, his hard cock buried deep in my ravaged ass. After a few moments to catch his breath, he pulled free and rolled over onto his back, tugging me in close under his arm. Adrift on a sea of warmth, mind utterly blank, I quickly fell asleep with my head on his chest.
The morning light woke me painfully early, and I pried open bleary eyes, staring up the rich velvet canopy. Utter confusion reigned for a long moment before I recalled the auction, and events of the previous night. Well, at least it's over now. My buyer still lay sleeping, one arm over his eyes to block out the encroaching day, but as I scooted away from him, he grunted and rolled onto his side. Sharp recognition slammed through me as I saw his face in full light for the first time. Miles Sinclair. The programming wizard who had revolutionized the computing world with his innovative search algorithms, forever changing the very nature of the Internet. A reclusive billionaire, he had rarely been seen after losing control of his company in a bitter divorce.
I must have made some sound, as he suddenly awoke, blinking and yawning. Spotting me, he smiled and reached out to tuck a strand of loose hair behind my ear. I just stared at him, still struggling with the realization that I'd been so thoroughly fucked by one of the wealthiest men in the nation. His hand fell away and he frowned at my rudeness, eyes narrowing. Before he could say anything, though, I scrambled off the bed and out of his reach.
The towel I'd gone to bed with was on the floor, and I snatched it up, wrapping it around myself with trembling hands. My thoughts were a jumbled mess and I babbled off the first thing that came to mind. "I need clothes." As the bright light glinted off the metal shackles circling my wrists, I added. "And that key."
Miles sat up slowly, the covers falling to his waist. A handsome man in his late thirties, he was trim and fit, his thick dark hair just starting to silver at the temples. I looked away, ashamed at the surge of lust that flickered though me. An awkward silence built, as he frowned thoughtfully at me and I avoided his eyes, staring at the bedspread instead.
"Why?" His deep voice was oddly gentle. But his question baffled me. Was he joking? Taken aback, I met his eyes, searching for some hint of amusement. He seemed serious. He swung his feet off the bed and stood, totally naked and completely unbothered by it. I looked away, blushing hotly.
"So I can go home?" My voice quavered with unshed tears. In the broad light of day, our encounter the previous night was revealed as the shameful, cheap transaction it really was. I'd prostituted myself to this man, exchanging my very first sexual encounter for cold hard cash. Self-disgust flooded through me, leaving me feeling nauseous and dirty. Wrapping my arms around myself, I turned my back to the bed. He was a genius, a self-made man, respected around the world for his intellect and business sense, and I was a whore. I wanted to run and hide.