Diana

A big thank you to gina_b_33 for taking the time to apply her editing talents to my story.

*****

I first met D via her blog. She caught my eye with her fun and inventive pictures, beauty with a sense of humour-that and a crazy fine ass, of course. We'd exchanged messages, which lead to flirting, which lead to . . . well, let's leave it at "creative sexting". D had a thing for role play, and I was excited and a bit shocked when she suggested taking things to a whole new level and playing out one of our scenarios for real.

I booked a suite at a fancy hotel in town, dressed in my sharpest suit and took my place at the bar. I patted my jacket pocket to reassure myself that my toys for the night were safe, and then I ordered drinks. Tonight, D would play the role of Diana, a high class escort for hire. We agreed that I'd publicly pay her for any services provided that night, and I had a few things in mind about what some of those 'services' would include. She'd teased me with a photo of the dress she was planning to wear that night. As I cradled my single malt at the bar, I scanned the room for her.

I needn't have worried. There was a palpable buzz in the room as she entered. Out of the corner of my eye, I could see heads turning. She knew how to make an entrance. She was wearing a black knee length dress that clung to her hips as she sashayed through the bar, long legs striding, and her feet in gold strappy heels.

Clearly braless, her firm breasts gently bounced with each step, straining against the plunging neckline, barely contained. Her black silk clutch bag complemented her dress. To complete her character, she was wearing a blonde wig. Tonight she was Diana, the huntress in pursuit of a good time and my cold hard cash.

As she drew up next to me, I could feel a dozen jealous eyes burning into me. I placed my hand on the small of her back, only to discover the dress was also backless, giving me an additional adrenaline shot of desire. Diana air-kissed both my cheeks and slipped one hand down to my crotch, resting it over my cock as it twitched to life. She slipped her hand lower and gave my balls a gentle squeeze while giving me a wink. This was our first prearranged meeting, and as agreed, I took my wallet from my jacket, peeled out a fifty, and discretely slipped it to Diana. She deftly slipped it inside her clutch bag and kissed my cheek.

"I got you a drink, dry martini, extra dirty, just like you tonight", I said with smile, sliding the v-shaped glass along the bar to her waiting hand. She picked out the cocktail stick, held it to her mouth and slowly drew off an olive, holding it between her pouting red lips and letting it linger before theatrically making it vanish. The tone was set for the evening as we drank, chatted and flirted, awash with the glamorous atmosphere of the glitzy bar. As she finished her drink, it was time for Diana to perform another service. Swirling the last of my drink around the melting ice, I leant close and whispered, "Why don't you order another round of drinks and give the barman a good look at your nipple?"

Another fifty disappeared into her clutch bag. Diana raised her right hand to get the barman's attention as her left reached across her chest and drew back the side of her dress. Her hard nipple stood proud and erect, just sneaking out the side, three quarters of her puckered pink disk of areola exposed. As the barman approached, she withdrew her hand and leaned forward, holding his eye as she calmly ordered another whisky for me and an expensive cocktail for herself. The barman visibly blushed, unable to help himself, his gaze drifted back to her bare nipple as he mixed her drink.

"Hope you liked your tip" she purred to him, slipping her dress back into place as she took the drinks from him.

We clinked glasses and surveyed the room, speculating on who was having an affair, and making up stories about the other customers. "See that older guy with the grey hair?" I asked, sotto voce, "the one who looks like the senior partner in a lawyer movie. He's been checking out your legs all night. Why don't you flash him? Give the old fart a thrill."

Diana giggled, tapped her bag, which was my cue to once again pay for services rendered, and swivelled her bar stool round to face him. As she fiddled with the hem of her dress, I could see him watching, trying to be discreet, but his eyes were magnetically drawn to her legs. I gave her a nudge and she opened her legs, lifting her dress dangerously up her thighs, giving him a clear view, as well as the half dozen others who were watching her. His eyes widened and then he hurriedly looked away. Mission accomplished; we touched glasses again and took a celebratory drink.

Emboldened, I slipped my hand in my pocket and wrapped my fingers around my surprise for Diana. I let my hand warm the cold steel before placing my hand on hers and carefully palming it to her. "Here's your next challenge, I want you to slip this in your pussy, right here at the bar". I said, fighting back the tremble in my voice. This wasn't going too far, was it?

Diana glanced down at the contents of her hand, back up to my eyes and raised a delicately shaped eyebrow. "You've got to be kidding, mister", she said, rolling the steel of the princess plug between her fingers, its red jewel glinting in the spotlights from the bar.

I replied, "When I booked you, you said satisfaction guaranteed. You came highly recommended", I said, sliding another fifty across the bar. She snatched the note, spiriting it into her bag as she tapped the plug on the bar top. Discretely, she popped it in her mouth, tucking it into her cheek, warming it, moistening it. Making sure she was facing the bar, Diana bent down, idly fiddling with the straps on her heels. Her hand slipped to her mouth, retrieved the plug and it quickly disappeared between her legs. I put my arm round her, providing a shield as she wiggled on the bar stool, sat up, and downed her drink.

"You owe me a big drink for that one. I'm having champagne, seeing as I'm a princess now".

She clicked her fingers and the barman was there in an instant, no doubt secretly hoping for another look at her pert, hard nipples. "A champagne and another scotch later", she told him in a sexy purr.

I had one more job for Diana. "Is your princess plug all warm and wet now?" I whispered, tipping my head towards her.

"Mmmm hmmmm. You wouldn't believe how wet", she smiled.

"In that case, I'd love you to pop it in your ass for me" I replied as I took a small vial of lube from my jacket and placed it in her clutch bag.

She gave me THAT look, pursing her full red lips into a pout, eyebrow arched. "That, mister, is going to cost you double! Just give me a few minutes in the ladies room."

Taking her bag, she glided off the bar stool and strode out of the bar. All eyes followed her, drinking in her exposed back, her swaying hips, as her golden heels clicked on the marble floor. I watched her elegant ass, imagining it swaying with the plug buried snugly inside. I reached into my jacket pocket for the last of tonight's props. I fingered the blue diamond-shaped pill, thinking "I'm going to need this tonight for sure", and then I washed it down with a big draw from my glass. I reflected on the evening so far. Diana may have been playing a role, but she was genuinely funny, witty and engaging. I'd had a great time, and not just because her nipples had been straining against the fabric of her dress all night.

My thoughts were interrupted by a text on my phone. Diana: "Now you owe me 100!"

I waited for her to walk back to the bar, watching the gentle sway of her breasts with each step. When she stood next to me, I placed a hand on her hip and let it roll down over the curve of her ass. My fingers traced the outline of her thong through her dress, following it down between her cheeks. I could feel the warmth of her ass on my palm and then the cool steel of the plug on my index finger. I caressed the raised outline of the gem gently in a circular motion, feeling the facets below the layers of dress and thong, making it wiggle in her ass.

"Well done", I said, kissing her cheek as I peeled two more notes from my wallet. "You've passed all my tests. Would you care to accompany me upstairs to my suite. Maybe a nightcap while you enjoy the view?"

"I thought you'd never ask". Smiling, she linked her arm in mine and we slowly walked out towards the elevators. I could feel the blue pill start to work its magic. I gave the grey haired lawyer guy a knowing wink as we walked past. Diana had her catch for the night, and I was ready for the challenge.

We stood, waiting at the elevators, a palpable sexual tension between us. Diana's hand strayed to my crotch, her fingers tracing the outline of my chemically enhanced erection. "Fuck, mister, I'm having some of that!" she said eagerly.

We were alone while waiting for the elevator. Our suite was on the 7th floor; finally, the bell dinged, the doors slid open and we stepped inside. Before the door was fully closed, Diana was on her knees, her fingers wrestling with my zip. I was wearing thin mesh trunks, and I could feel that they were already sticky with precum. Her hand slipped inside, pulling down my trunks and unleashing my cock. In one swift movement, her hand rolled back my foreskin and gripped me firmly at the base of my shaft. And then her lips devoured me, hungry and eager, bobbing and slurping me deep into her willing mouth.

I placed one hand on her head, feeling the rhythm of her sucking, revelling in her attention. I kept one eye on the action below, another on the elevator numbers as they ticked upwards. The danger of being caught, coupled with the exquisite sensations running through my cock, made me catch my breath. I had to lean hard against the wall as I saw Diana's cheek bulge in and out as she consumed me. Four ... five ... the elevator continued its inevitable climb. I let out a low moan, unable to contain myself. As the lights passed six, I felt Diana's lips on mine, pressing softly, giving me a taste of my own briny precum.

"Shhh, mister, that's just the appetiser" she whispered, tucking my cock back into my suit trousers.

I fumbled with my zip. In my engorged state there was no way I was getting my cock back into my trunks; I just had to conceal it as best I could until we got to our suite. Diana's lipstick was smudged across her cheek. If anyone had seen us, it would have been obvious what we'd been up to as we walked arm in arm towards our room. Diana was cool, calm, professional, yet underneath we could both feel a maelstrom of lust that was about to explode. We made it to the door, and stepped inside. As the door clicked shut behind us, time seemed to stand still, if only for two heartbeats. Our bodies were like coiled springs, ready to spring free.

My hands cupped her face, fingers spread wide across her soft cheeks. We kissed, hard, deep, tongues fighting for supremacy. Her lips pulled at mine, drawing out my lower lip, and making me tremble. My hands slid to her shoulders, then to her upper arms, holding her tight. I ran my teeth lightly across her neck, and then I kissed her throat. The heat of her body, mixed with the smell of her skin, was intoxicating. I had to consume her, all of her.

As I kissed her neck, I slipped my hands inside the bodice of her dress, filling them with the soft swell of her magnificent breasts. I'd experienced a tinge of jealousy when the barman had such a great view of her nipple, but her boldness had overcome that feeling. Cupping a breast in each hand, I moved my hands apart, peeling her dress away to reveal the soft fruit beneath. I gazed down at the pale globes filling my hands, my thumbs gently stroking the puckered brown disks surrounding her bullet hard nipples. Flushed with desire, I bent my head down and began to feast.

I squeezed and pushed her breasts together, my mouth latching onto her right nipple, suckling hard. I took her full in my mouth, cramming her in, lips sucking, tongue flicking over her aroused peak. Hungry for more, I turned my attention to her left breast, my tongue rolling up her nipple and forcing it against the back of my teeth. I gripped it between my teeth and pulled, gently at first, then harder. Diana's fingers twisted in my hair. She moaned softly as pleasure mingled with pain. My hands kneaded and squeezed, my mouth alternating between her nipples, pulling, licking, sucking, ravenous for her body.

"Fuck me, Matt! Give me your big cock!"

No man could ignore such a command from Diana. I slipped off my jacket, undid my belt, and dropped my suit trousers. My trunks, still pulled down from Diana's oral exploration, clung to my thighs. I gripped her thighs just under her ass and pressed her hard against the wall, lifting her up. Diana wrapped her arms round my neck and her legs circled my waist. I pressed my cock against her thong and probed, seeking entrance. Her skimpy triangle was slick with her juice, and my bulging helmet eased it to one side. The sensation of her warm wet lips hit me like an electric shock as I slipped inside her.

"Oooohhh Matt," she groaned as I lowered her down onto my shaft, filling her. Diana's breasts were crushed against my chest, her heat permeating through my shirt to my skin.

Her pussy was silky smooth inside, wet, warm and very tight around me. I rotated my hips, thrusting up into her, penetrating her depths, her legs spread wide were still wrapped around me. As I slipped in and out, I could feel the swell of the princess plug, still safely buried in her ass and making her feel even tighter around me. My lips sought her neck, kissing her throat as her fingernails dug into my back.

"Mmmm mmmm make me cum."

Holding her tight, I turned around and carried her to the bed. I kicked off my shoes, stepped out of my trousers and knelt before her. I pushed her dress up above her waist and peeled off her sticky thong, tossing it over my shoulder. I gazed at her pussy for the first time. I'd seen it in her sexts, but the reality was even better. Her pussy was smooth as a mirror and glistened with juice, her lips standing proud and erect. My left hand reached up for her breast while the right slipped under her ass cheek, my thumb resting on the jewel of her butt plug.

I breathed in her scent, rich and intoxicating as it filled my lungs. I tipped my head to one side, my lips sucking on her left labia, pulling it into my mouth. I worked my way slowly downwards, my lips kissing and sucking hers as my tongue traced circles inside her. Diana tasted of a heady cocktail of her own sweet musk mixed with my salty precum. The tip of my tongue flicked over her tight cunt hole, teasing and probing it.

I drew my fingers and thumb up and over her exposed breast, focusing on her nipple. At the same time, I pressed on the jewelled end of her plug, pushing it deeper into the secret recess of her ass. As she gasped, I plunged my tongue in deep, tasting her rich nectar. I worked her nipple and ass together, synchronised with the thrusting of my tongue.

"Mmm Matt, yes, don't stop," she purred, resting her feet on my back and pulling me in. Her high heels acted like spurs, bidding me to eat her pussy harder, faster. My tongue slipped form her tight hole and wended its way upwards, a serpentine path from lip to swollen lip, pausing just below her engorged clit. I nuzzled her clit with the tip of my nose as my lips and tongue teased her vulva, lapping up her juices.

I kissed her full on her clit, my lips enveloping it, my tongue exploring every fold of her skin, edging around her hard pearl of pleasure. I could feel the tremble in Diana's body. It was time to take her over the edge. My thumb rotated on her plug, making it twist and thrust like a jewelled piston in her ass. My lips devoured her pussy as my tongue pressed hard on her aching clit, alternating between rapid flicks and long slow circles.

"Haaah! Hahhhh! Mmmmm! Ohhh! Ohhh!"

Diana's heels raked across my back as her body twisted, pushing her pussy deeper into my face as she sought her climax.

"Eat me Matt! Faster! Mmmm! Ohhhhh!"

Her back arched as her body convulsed with her breaking orgasm. Her hands gripped the sheets, clenching them tight as her feet forced my face to her harder. Her cunt was gripped by spasms as she flooded my face with her juices. I was anointed with her cum.

"Cum inside of me, Matt. Fill me up with your cock," she moaned, her neck and breasts flushed pink with pleasure. I stripped off my shirt, finally naked before my goddess. I took hold of her dress and lifted it over her head, revealing her full beauty. My cock was bulging, the effects of the Viagra and the taste of her pussy combining to make me harder than ever. I rubbed my purple helmet over her clit, gliding each ridge around her hard nub.

I slowly worked my cock down, gliding it between her swollen lips, glazing myself with her juice. The heat of her cunt hole drew me in like a magnet. I gripped her thighs, holding her legs wide open and easing my cock into her. Diana's hands reached forward to touch my belly as I gently started to thrust, pivoting my hips.

"Fuck, Diana, I'm so hard for you," I gasped as the warm tightness of her cunt sent a wave of pleasure up my spine. I gazed at her slowly undulating breasts, our bodies moving in harmony. My mind could think of only one thing: how to make this woman come again, filling the room with the sounds of her pleasure, feeling her quake and tremble while my cock is buried deep inside her.

I leaned forward, supporting my weight on my arms, her legs spread by my thighs. Diana held my shoulders as she hooked her ankles over mine, locking us together. I could thrust more freely now, my heavy balls swinging, slapping on her soft ass cheeks.

"Haaaah! Hahhh! Fuck me harder, Matt, fuck me harder! Harder! Deeper!"

My cock obeyed, pushing up hard, flexing, making my helmet bulge and throb against her cervix. I could feel her butt plug making her cunt even tighter, more inviting. Diana craved more cock. I was her slave. I had to go harder than ever before. I rolled my elbows under her knees and forced her legs up, spreading them wide. Her high heels waved in the air as I pounded hard, giving her every inch of my cock.

I lay flat on her chest, pining her down, her fingers clawing at my back. Driven by lust, I gave her everything I had. I was possessed, my body commanded to pleasure her, to fill her. I kissed her neck hungrily as the room filled with the sound of our passion.

"Mmmm! Mmmm! Oh yes! Haaah! Haaaah! Yes!"

As her orgasm ripped through her body, I continued to thrust hard, stretching her tight hole with my engorged cock. Her fingers raked my back, the pain mixing with my pleasure making me gasp. I could feel every shake, every twitch, as our bodies were meshed together. Her climax washed over me, her waves breaking on my skin. Her pussy clenched and pulsed, massaging my shaft, pressing my bulging veins into her flesh.

I needed badly to cum. The fire in my cock was unstoppable. My balls were full and throbbing. I stood at the edge of the bed and pulled her close, sliding her across the crumpled sheets. My right hand clenched my shaft, its swollen length filling my hand. My left hand grabbed my ass, helping me balance as I worked my cock, fast and hard. My fingers were covered in a sticky mix of precum and Diana's cunt cream, which frothed as I stroked my cock furiously.

"Cum for me, Matt! Cover me with your cum!"

I was abandoned to lust. My chest was tight, my breath ragged and urgent. I gripped my ass hard as I jerked my cock, flooding my body with sensations.

"Ohhh! Ohhh! Fuck! Yes, yes! Ahhhh! Ahhhhh! Yesssss!"

My orgasm tore through my body, making me a juddering, twitching puppet. My face flushed red as a deep animal roar burst from my lungs. I was still thrusting and stroking as my balls erupted, sending a sine wave of semen through the air. Still it came, my balls tightening, forcing every drop out, a second and a third, and then I stood there, spent and gasping.