Private Dick pleases his sexy boss quickly and often
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The breath lozenge tasted like wintergreen and desperation - the kind of flavor that makes you acutely aware of your own grime. Gwen’s nose wrinkled slightly, but her smirk never wavered. She just patted my cheek like I was a misbehaving dog she found charming.
“Hop in, hero,” she purred, sliding into the driver’s seat with the practiced ease of someone who’d spent too much time in cars worth more than houses. The leather groaned under me as I climbed in, still half-convinced it was a hallucination brought on by bad dumpster food.
After a satisfying greasy cheeseburger, we stopped at a gas station. She ordered, “Fill her with premium. I’ll get condoms.”
Once we climbed back in, she pressed “Inizio”, the start button. The quad-turbo V16 engine snarled to life again. “You’re staring at my chest,” she noted, without looking at me.
I lied with a playful accusation. “I wasn’t. You’re crazy.”
She laughed, loud and unguarded. “So I’ve been told.” She stomped the gas pedal, flinging the car downroad with the acceleration of a popped balloon. In barely a block, the speedometer hit triple digits! It’s amazing what half a million bucks and two thousand horsepower can do. She piloted the aspiring aircraft between a pair of trucks with only inches to spare! Her driving was scary as an opposed beach landing, and more dangerous!
The hotel wasn’t just fancy, it was the kind of place where the doormen wore gloves and judged you with their souls. Gwen tossed the valet her keys. His smile changed to a frown as his gaze moved from her abundant cleavage to the filthy bum escorting her.
I was quite uncomfortable wearing a torn T-shirt and dirty jeans. All the employees and most guests wore suits or fancy designer clothing. Three with nametags stared with suspicion in their eyes. She grabbed my hand. “Relax. They’ve seen worse.”
The elevator ride up was silent except for the hum of machinery and the sound of my heart trying to escape my chest. Gwen leaned against the mirrored wall, studying me like an unfinished puzzle. “You’re not what I expected.”
I asked, “What did you expect?”
“A man who’d take the money and run. Or rob me. Or fuck me right there against the dumpster.” She touched a fingertip to the corner of her mouth and sighed. “Shove me down on a pile of trash, and rape me to a three-hole creampie. Or grab my hair and give me a pearl necklace in public.” The smile and the longing tone in her voice surprised and aroused me. She stroked my thigh, inspiring a slow growth. She giggled and continued, “You did the heroic thing, though. That was… surprising.” The elevator dinged. I couldn’t tell if she meant it was a good surprise or bad.
Her suite smelled like roses, jasmine, and money. She kicked off her expensive high heels, so I untied and pulled off my worn work boots. The shower was glass-walled and big enough for eight. Gwen didn’t bother with preamble. She peeled off her dress in one smooth motion, dropping it to the bathroom floor. No bra. Just those red panties, with a dark moisture streak down the middle.
“Your turn,” she said, nodding at my rags. I hesitated. She rolled her eyes. “Oh, please. You already flashed me. Don’t pretend you’re shy.”
I wasn’t. But the sudden shifts from street fight, to traffic terror, then luxury seduction left my emotions dizzy. Still, I stripped.
Gwen whistled. “Damn. Even soft, you’re impressive!”
“You, too!” I gently grabbed a weighty breast and led her into the shower. The hot spray was more relaxing and comfortable than I expected.
Gwen lathered her hands with some fancy shit that smelled like raspberry, lemon, and lust. She soaped most of our bodies, then lightly dragged her sharp nails down my chest. “So,” she murmured, her breath warm against my shoulder. “You’re really a Marine?”
“Was.”
“Hmm.” Her fingers traced a scar on my hip, the one from an AK-74 bullet. “Explains the reflexes.” Her touch wandered lower, making me groan. She laughed against my skin. “Oooh, that’s the sound I wanted.”
We kissed, washed, and fondled each other a delectably long time.
She tickled my belly and made another offer, "I'll pay for every orgasm you give me, if you don't cum tonight. Can you avoid dumping a wad, for a big wad of cash? Five grand a climax, if you don't ejaculate?"
I desperately wanted to breed her, but the promise of abundant money when I had none...
"What do you say, stud?" The numbers fizzed in my skull like champagne. Five thousand a cum! Gwen's greedy little smirk told me she thought I'd blow a load after just one or two, maybe even pop first. Her fingers circled my cockhead, thumb rubbing the tip like she was sealing a deal.
“Sure!”
"You're betting against biology," she growled. I palmed her ass hard enough to lift her. Water sluiced between us. "Women can go multiples. Men? You get one shot."
"But if my one shot is a cannon blast through the heart…"
Gwen giggled and ripped open a condom pack, quickly rolling it on me. She ground her pelvis against my thigh, her wet womanhood painting my leg. I teased, "Marines have discipline, but you?" Her teeth grazed my earlobe. "You’re desperate, craving oral and a big dick. You look ready to drown me in your needy pussy.”
She laughed and asked, “Can you control yourself and get me off half a dozen times? Ten grand extra if I cum six times and you don’t. Think you can do it? For forty thousand dollars?” The challenge lit up my nerves brighter than the hotel's chandeliers.
I spun her around, her tits flattening against the chilled glass as I bracketed her hips. I dragged my thick cock through her slick folds. I said, "Enjoy it. I know I’ll enjoy your money. Aaah! And fucking your superhot body.”
Gwen's laugh turned into a gasp when I shoved in, filling her fully, totally, touching her cervix. She was the first White girl I ever screwed, and one of the tightest! I smiled seeing I had four inches left over. Her back arched, red nails scraping condensation off the shower walls. "Fuck - yes, that's - Oh GAWD! Right there!"
I fucked her slowly, repeatedly penetrating at the same angle, grinding deep on every thrust. Her thighs trembled. The orgasm ripped through her so violently her knees buckled. I caught her by the waist as she convulsed around me. "One," I panted against her shoulder. She slumped against me, chest heaving. "I’m not even fully hard yet," I lied, my cock sliding back inside her.
Truth was, I was halfway to blowing. Her greedy little cunt kept milking me even after she came. I wanted to empty myself, but five grand would cover food and a small apartment for three or four months. Ten would get me half a year, plus a permit and a cheap gun, just in case. With FORTY…
Gwen twisted around, her blue eyes glittering. She demanded, "Bed! Now!"
I carried her dripping wet body across the suite, tossing her onto silk sheets that cost more than her fancy phone. She spread her lower lips, offering an erotic feast. "Make me scream this time."
I had to ruin her for other men, make her as desperate for my dick as I was for her money. The sheets smelled of lavender body oil and perfume, something expensive, something wasted on a man who slept in a box under a bridge. Her fingers tangled in my hair as I buried my face between her thighs, licking her slow at first, then faster when her hips jerked. She tasted of salt, tartness, and indulgence; like an excellent savory dish and a glass of fine wine. I was broke and frantic for cash, but would have devoured her deliciously muff for free.
“You - fuck! You’ve done this before, a lot. Damn, that’s good!” She gasped again, and her ankles locked behind my head.
I didn’t answer. My tongue circled her clit, pressing just enough to make her fingers claw at the sheets. She came with a shudder, her body arching off the bed, her moan loud enough to wake those across the hall. She shouted, “YES!”
I lifted my head, grinning. “Two.”
Gwen’s chest heaved. “No point counting.” pant pant “You’re great, but you can’t win.”
“I made you cum twice. Pay up.”
“When you leave.” GASP “Assuming you can hold out.”
Her hand slid down my stomach, nails dragging lightly, before wrapping around my cock. She stroked me slow, her thumb brushing over the tip. “You getting close?”
I smiled and swallowed a groan. “Nope.”
She smirked. “Liar!” She rolled me off and jumped on top. Soon her mouth was on me, hot and wet, her tongue swirling around the head before she took me deep. Amazingly deep! Nobody had ever deepthroated me before, and I thought nobody could. It felt AMAZING! Euphoric! My hands fisted in the sheets. Fuck! She was good - too good. Her lips tightened, her head bobbing, and I had to bite my tongue to keep from thrusting farther into her throat. When she pulled back, she gasped and tears formed at the corners of her eyes. She asked, “Close?”
I exhaled hard. “Uh! Oooh! Maybe.”
She straddled me, sinking down onto my cock with a sigh. I gripped her hips, flipping us over so she was beneath me. She gasped as I pushed back in, her legs hooking around my waist.
I fucked her deep, with my lowest abdominal muscles grinding against her clit with every thrust, until she was clawing my back. Her pleasure cries were muffled against my shoulder. She came with a whimper, her body tightening around me.
I kissed her, swallowing her moan as I rocked my hips. “That’s the idea.” I kept thrusting, screwing and fucking her, in out, fucking and screwing, up and down, in and out. She groaned and cried out, “UHH! SO GOOD!”
And then - because I was a Marine, because I was bankrupt and starving, I pulled out before I lost control.
Her eyes widened. “You - you stopped?”
I grinned, wiping sweat from my brow. “Four so far.” I gasped in precious oxygen and exhaled. “Twenty thousand bucks!”
She stared at me, panting. Then slowly, she smiled. “Only if you win.” She reached for me again. I had barely caught my breath when Gwen twisted onto her stomach, arching her back in deliberate invitation. Her fingers dug into the pillows as she glanced over her shoulder, eyes half-lidded, lips parted, and uttered two breathless commands:
"Put on a fresh condom” GASP “then FUCK MY ASS!"
The demand punched through me like a sniper round. The way she ground against the mattress, how her fingers spread her own cheeks to show the tight furl of her slightly fuzzy buttflower, already glistening with lube from the nightstand.
FUCK! She'd planned it!
But instinct was too strong… I dragged a new condom over my aching cock, barely recognizing my own ragged breathing. Gwen whimpered when I pressed my penis against her tightest hole, her body resisting for one delicious moment before yielding. She gasped my name like a curse as I sank in, her muscles fluttering around me in a rhythm that felt like drowning. “Butt fuck me, Richard! Pound my pooper!”
I was more than happy to obey. I reached beneath her and rubbed her vulva as I packed her fudge, pumped her poo hole, driving my dick deep inside her. She complained as she climaxed again, “AARGH! You beautiful bastard! Not again! UGH!"
“Five," I growled, but the count was soon meaningless. Gwen's moans dissolved into incoherence as I fucked her bottom with slow, grinding thrusts, each one wrenching another choked cry from her throat. When her sixth orgasm hit, she sobbed into the sheets, her nails tearing at the fabric.
I was close myself, so painfully, deliciously close!
All eleven of my man inches were in her. My balls bounced against her butt with every thrust. My cockhead was most of the way up her colon! Before I could pull out, her body clamped down on me like a vise. I verbalized my torment, “Not yet! Not… yet!” I lost control, spilling into the condom with a groan that sounded like surrender instead of victory. "NOOO!"
Gwen's laughter was muffled by a pillow. "Told you!” GASP “Women always win!"
I didn't argue. I didn’t have the oxygen or energy. I panted rapidly, thinking, “Forty grand! I lost $40,000! SHIT!”
The sexiest woman I’d ever touch smiled and lit a cigarette, as sleep swallowed me.