This story was influenced by the work of KeyesLodge on Literotica. Go read his stuff if you haven’t already.
Starring: Jessica Chastain
I’m not quite sure what the images were that were flickering on my giant plasma screen, but whatever they may have been I wasn’t paying them much attention. Truth be told there was only one thing I was watching on that warm Wednesday evening and that was the clock on the wall behind it. To say I was excited about my newest visitor would be putting it mildly. I’d never had a celebrity guest before and I’d barely been able to contain my elation since she’d phoned to book a stay at my establishment the previous Saturday.
Up until then it had been a perfectly ordinary day. I was sitting here watching TV, just like I am now, waiting for one of my regulars to arrive when the phone rang. Nothing strange about that. I’m running a thriving business here, after all. So I answered and the caller greeted me with a warm ‘hello’. It was a woman. Nothing strange about that either. I don’t get many men ringing this place, save for the odd jealous husband whose wife has been caught in the act.
Anyway, the woman said she was interested in booking a stay, and asked me if I had any slots available that coming week. Now, I wouldn’t call that strange per se, but it’s not exactly a common occurrence. In fact, midweek bookings are rare. I’ve run this place for nearly a year now and I think this was maybe my tenth. Why, you ask? Well, there’s a very simple explanation for that. People work during the week. Not many people work on weekends, except for nurses, shopgirls and bar staff, and I think it would be fair to say that a stay at this place would be a little out of their price range.
So that’s why I was able to fit this woman in so quickly. Usually guests have to book a weekend stay months in advance, but those lucky few who have weekdays free pretty much have my calendar at their disposal. So I told the woman that my entire week was free and she could take her pick. She said she’d like a stay from Wednesday evening, through to Thursday. Pretty standard for a first timer. Regulars often booked Friday to Sunday, and for the ones who could come during the week…well, it wasn’t unheard of for them to book Monday to Friday.
I told her that was fine and asked her for her name, clarifying that it had to be her real name for billing purposes. New guests often tried to use pseudonyms. She told me her name was Jessica and I jotted her name on the calendar. Jessica Chastain. I stopped in my tracks, actually breaking the nib of the pencil, the way actors do in comedy films. I was stunned. A famous actress. And not just any famous actress. A freakin’ Academy Award-winning actress. And a drop dead gorgeous one at that.
OK, I should probably start from the top here, right? Hi. My name is Tyler. I’m 24 years old and I run a hotel of sorts (in all honesty, I don’t have an official name for it) catering solely to women. Wealthy women. Usually older. Late 30s to early 40s is my typical age range. Why just women? Well let’s just say that, as a heterosexual man, the kind of services I provide are ones that I have little interest in extending to males. Am I an escort? Nope. Visitors pay only for a stay at my establishment. Any other services they seek are strictly pro bono.
So how did this all begin? Well let me take you back to when I finished college. Two years ago. I bummed around that summer- partying, having casual sex- enjoying the last few months of freedom before I faced the real world. I got a job at an accountancy firm in West Hollywood (I’m an LA boy, born and bred) in September and worked there for a few months whilst living with my parents. Now, it was around this time that my grandfather, quite a wealthy man, very sadly passed away. He was a great guy and I miss him dearly, but I’d be lying if I said I wasn’t pleased when I learned that he’d left me his holiday home in the LA suburbs.
I’d been looking to move out of my parent’s home and this was the perfect opportunity. No mortgage. No rent to pay. I was at the bottom of the pile at the accountancy firm so my pay was pretty much shit, but it was enough to feed myself and pay the bills, so I moved in right away. The commute to work was a bitch but I loved having my own place. And what’s more, it was friggin’ huge! I’d been here a few times when I was a kid and I’d forgotten quite how large it truly was. Eight bedrooms, two enormous lounges, garage, huge driveway, swimming pool. The whole nine yards.
And to say it improved my luck with the ladies would be an understatement. I’m a good looking guy and I’m in great shape, so I wasn’t exactly starved for action to begin with. But when I got a girl back to this place she never wanted to leave. What would have been simple one night stands during my college days soon turned into full weekends of non-stop sex, and barely a Friday night passed without me bringing a woman back to what was quickly becoming an archetypal bachelor pad. But it was a visit of one woman in particular that transformed my life into the near 24 hour sexathon that it is today.
That woman was Heather, my mom’s best friend and what I’d always considered to be an absolute textbook MILF. She said my mom had told her about me moving to this place and she dropped by unannounced to pay me a visit in my new digs. Unannounced, but certainly not unwelcome. She was a little younger than my mom but they’d been friends for years. I’d known her more or less my whole life and I’d always had a crush on her. As I’d gotten older, I started to expect that she had a thing for me too. And well…I was right.
What started as a brief visit to check out my new home quickly evolved into one of those all weekend sex marathons that I talked about earlier. I couldn’t believe it. I’d jerked off to this woman countless times during my teenage years, and there I was, less than ten years later, banging the life out of her for two days straight. It was fucking incredible! Anyway, that’s enough bragging from me. Now onto the important part. During a brief break in our weekend-long fuck session, Heather took a moment to gush about how incredible the house was. And how incredible I was too.
“You know, you could probably make a business out of this,” she suggested, her head on my shoulder, a finger tracing a line in the grooves of my pecs.
“What? Bring women back here and fuck them for money?” I laughed, thinking that either she was joking, or I’d grossly misunderstood.
“Yeah,” she said. “Think about it. A place to have no strings attached sex with a hot guy who knows how to fuck. This is exactly what women have been looking for.”
“It is?”
“Uh huh.”
“But wouldn’t that make me a…manwhore?”
Heather laughed. “I believe the term is ‘escort’. But no, it wouldn’t. Women would pay to come and stay here. To relax and unwind. To get away from the stress of their jobs. To escape from their husbands and kids. What they do when they’re here is up to them. And up to you.”
I was intrigued, but I’ve gotta say, it sounded fanciful. “And you think women would want to do that?”
“I know I would. I know a bunch of other women who would too. I’ll put them in touch with you if you like.”
I was still a little sceptical, and really couldn’t see how anything that sounded so great could actually work out in reality. But hey, it was worth a try, right? And well, it turns out that Heather was right. Women
were interested in staying at my new home for the weekend. And hot ones at that! Most were high powered business women who, just as Heather said, wanted to unwind after a week in the office, and escape the monotony of a weekend with their husbands and kids. It started with a few and soon my phone was ringing off the hook with horny MILFs looking to book a stay at the hottest hotel in town.
My schedule was filling quickly, and it wasn’t long before prospective visitors were being made to wait up to two months for a booking. It was around this time that I got my first visitor on a weekday. One of my regulars called me up and after being hit with the two month wait, desperately blurted out “well, how about a weekday then?”, in a way that suggested she was booking first and thinking second. I knew full well that she worked during the week, as did I, so a weekday stay wasn’t exactly convenient for either of us.
The best I could offer her was a one night stay and a lift back into LA the next morning when I drove to work. She accepted, but it got me thinking, maybe I could have a go at doing this full time. Bookings didn’t come cheap so I was making decent money from my weekend guests alone. Three or four weekday visitors a month and I’d be pretty much set. After a week or two of hemming and hawing, I decided to give it a shot and I gave in my notice at my place of work.
My notice period was a month, and much of it was spent worrying that the bottom was going to fall out of the fucking-women-for-money-but-not-really game, and I was going to find myself jobless with bills up the wazoo, despite still making bookings on an almost daily basis. Well needless to say, my fears were irrational. Like I said before, weekday bookings weren’t exactly common, but I was getting enough to live on and even found myself with some spare cash to get the pool running and repurpose some of the empty rooms.
One I turned into a gym, which saved me having to keep driving to the public one 30 minutes away, and also allowed long-staying guests to get in a morning workout. Another I turned into a massage room, which provided its share of fun with happy endings aplenty. I don’t have any formal training or anything, but several guests find my technique to be great for relieving tension.
And that is pretty much that. Now that you’re all caught up, let’s get back to Miss Chastain.
“OK,” I said, after probably too long a pause. “Lovely to meet you, Miss Chastain.”
“We haven’t met yet, honey,” Jessica laughed. “Though from what I’ve heard about you, I’m very excited to. And please, call me Jessica.”
“Certainly, Jessica,” I replied, hiding my nerves as best I could.
I almost never got nervous around guests these days but I had to admit that my first celebrity caller was making me a little flustered. Growing up in LA, I used to see famous people out and about all the time, but this was my first time actually conversing with one. What’s more, I was trying to fathom how such a big name star had found out about my little establishment in the first place.
Being so close to Hollywood, I had my share of visitors from the entertainment industry- producers and the like, so I figured it had come through one of them. One of my regulars was a big player at HBO, and Jessica had recently worked on a miniseries for them with Oscar Isaac, so that seemed like the most logical connection. I made a mental note to thank said regular with a generous discount next time she made a booking.
Usually with new potential visitors I would arrange a Zoom call to check if we were the right match and to see if they had any special requests for their stay. Or at least that’s what I told them. In truth, it was an opportunity to see if prospective guests possessed the physical attributes to which I’d now grown accustomed. Shallow? Maybe a little, but I was now getting so many booking enquiries that I could afford to pick and choose.
Anyway, there was obviously no need for that with Jessica so I completed the preliminaries over the phone. I asked her if there was anything in particular that she wanted to do during her stay and she filled me in on a fantasy she’d had that got my heart pumping with excitement. Once all that had been taken care of, we settled on exact times and I gave her the ZIP code for her GPS. Turns out she actually lives in New York, but she was in LA for filming and had a couple days off. And what better way to spend them than at my place? I signed off formally, biting my tongue to keep from calling her Miss Chastain, and told her I’d see her on Wednesday.
“I can’t wait,” she replied.
Neither could I.
The doorbell rang at 5.15. Jessica was a little late, but I’d gotten used to that with LA traffic. I switched off the TV and went to answer the door. Jessica said she would freshen up when she got here so I figured she’d be arriving in casual mode. I opted to match her with shorts, a t-shirt and a pair of flip flops.
I answered the door and there she was, my very first celebrity guest. She looked even more stunning in person than she did on screen, even in sweats, minimal makeup and her hair in a bun. My greeting was standard fare. Hug. Kiss on the cheek. How was the drive? Did she find the place OK? Once the pleasantries were done with, I took command of the suitcase she was wheeling and gave a quick tour of the house, allocating a room in which she could freshen up.
I went to my room and took a shower, sprayed on some cologne and styled my hair. I picked out some clothes- a pair of skinny fit suit pants, a freshly pressed white shirt and a neatly buffed pair of brogues. I was ready some time before Jessica, as I’d expected, and waited in my room as per our arrangement. Jessica was in her room for a while and I was dying to see the vision she was crafting in the ensuite mirror.
Finally the door opened and I heard her stilettos thud down the hallway as she headed for the front door. The door slammed shut and now I was in fantasy mode. She waited a minute or two then rang the doorbell. I took a quick look in the mirror then went to answer it.
“Tyler?” she said, making a show of taking off her wedding ring and slipping it into her handbag. Undoubtedly part of her fantasy.
“Jessica?” I replied, ushering her inside. “Great to finally meet you in person.”
“Great to meet you too.” We hugged again and I got a whiff of her perfume as she kissed my cheek. “You’re even more handsome than your profile.”
“Thank you,” I said, playing along as best I could.
It was difficult to pretend that I was seeing her for the first time, considering we’d just met not more than an hour ago, but telling her how beautiful she looked didn’t require much performance. She looked absolutely stunning in a long black dress that was split almost up to the pantyline, entirely barebacked and tight in all the right places. It was jaw dropping. As was the rest of her. Her makeup had been applied to devastating effect and that gorgeous red hair of hers had been lightly curled, hanging gracefully over one of her shoulders.
Her fantasy, as you’ve probably already guessed, was meeting a man on a dating app for a night of no strings passion. That might seem a little vanilla for us mere mortals, but this is the kind of thing that famous people just can’t do. Especially ones with a husband and two children waiting for them at home. What’s more, our ‘first date’ was at my house- a serious no-no for any woman, but for Jessica Chastain it was a surefire way to end up tied in a stalker’s basement for days on end. For someone of her fame and beauty, the only way to engage in something like this was with a guy like me.
I took her to the bar and she picked out a bottle of wine. I poured us both a glass and she accompanied me to the kitchen while I got started on dinner. My famous chicken stir fry. I cooked, we drank, we chatted, both of us in character. Jessica had made it clear to me in advance that she wasn’t going to be movie star Jessica Chastain in this little scenario, but had kept me in the dark about what her character was going to do for a living. Turns out this evening Jessica was going to be Hollywood talent agent Jessica Chastain. Which made a lot of sense. Right about what you know, and all that. She talked for a while about her ‘job’, about difficult clients and high-profile roles that she’d booked them in. I tried to workout if she was referring to anyone in particular, but quickly came to the conclusion that it was entirely fictional.
Another thing, Jessica hadn’t told me what my ‘job’ was going to be either and I kind of assumed I’d get to pick my own. I was wrong.
“So you’re a masseur, right?” she said, a tiny character-breaking smirk suggesting that she’d thought of that earlier when I gave her the tour of the house. Perhaps in hope of a free sample of my ‘professional’ talents. “How long have you been doing that? Not long I’m guessing,” she added, a clear reference to my tender age. Something that I’m beginning to suspect might play quite a sizable part in this fantasy of hers.
“Five years. I started training right out of high school,” I said playing up to the fantasy.
Jessica briefly broke character again, flashing me a second grin that told me I was right to do so. “I see. This is a lovely house by the way. How many people do you have to rubdown to afford a place like this?”
I laughed. “I get some good tips.”
“I bet you do,” Jessica quipped and I received a flirty smile from both the actress and talent agent alike.
Dinner was ready and I served us up a couple of plates. We took them through to the lounge and I refreshed our drinks. Our mealtime conversation continued in much the same vein- extremely flirtatious and you could cut the sexual tension with a knife. I was dying to get my hands on her and it was clear that the opposite was just as true, but there was something about having to wait which made it all the hotter. Most guests would be all over me before I’d even closed the front door, which of course I had no complaints about. But part of me actually preferred it this way. And there was little doubt that letting the tension build to such intolerable levels would result in some of the best sex that either of us had ever had.
We finished up dinner and I offered her dessert, but Jessica declined. I should have known that a woman with her figure wouldn’t go in for sweets. I poured out the rest of the wine and we took our glasses to the couch where the conversation continued. Jessica might not have been a casual dater in real life but she played the part very well. Unsurprising for a woman of her talent. She had been flirtatious from minute one and only became more so as the evening progressed.
Soon, the playful dialogue was accompanied by light physical contact. A touch of my arm. A pat of my thigh. Draining the last of her wine, Jessica kicked off her stilettos and curled her legs up onto the sofa, draping an arm across my shoulders. Suddenly no more needed to be said. This was the moment and we both knew it. We both leaned in, slowly, until our lips touched. It should come as no surprise to learn that Jessica Chastain is a phenomenal kisser. Not overly aggressive, but forceful enough that I knew I was in for a hell of a time. Her lips were perfect- soft and full with expert application of her shiny pink lipstick. Not enough to smear but enough to leave a pleasant taste tingling on the edge of my mouth.
Tongue was applied as things heated up and a hand returned to my thigh, trailing along the seam of my pants. I reciprocated with a hand on her back, lightly stroking the exposed flesh. My cock was growing stiffer by the minute and soon the hand that was snaking along my thigh made contact with the tip. The kissing intensified, and Jessica started stroking me through my pants, traversing the length of my shaft with her palm. She got up onto her knees and her hands moved to my belt, unbuckling it smoothly as our lips stayed fastened together. Unzipping my pants, her lips moved down to my neck as she reached inside. Sliding her fingers through the hole in my boxers, she fed my dick through my open zipper and her lips formed a perfect O as she laid her eyes upon it.
“Wow!” she said, raising those neatly plucked brows.
Oh, yeah. Did I forget to mention that I’m hung like a Shire horse? Well, I am. Eight inches to be exact, and I could tell from the look on her face that I’m the biggest that Jessica had seen. I’m guessing my HBO regular informed her of my size, but I could tell from Jessica’s reaction that picturing an eight inch dick and seeing one in person are two very different things.
“My God! Erica said you were big, but holy shit!”
And there it is. Looks like a certain HBO exec is getting a discount coming her way.
Jessica slid back a little on the couch, pushing up that gorgeous ass, hugged tightly by the fabric of her dress. Her head dipped down and those lovely soft lips pressed against the tip of my penis and slid down past the crown. I let out a soft moan as my head slid into the warmth of her mouth, her tongue against the base as she started sucking. She’d only just started, of course, but I could tell already that Jessica gave fantastic blowjobs. Spit was already sloshing around her mouth, drenching my crown, and each and every suck was performed with optimum pressure.
A hand rested on my thigh and the other crept beneath the hem of my shirt, getting a feel for my six pack abs. She bobbed her head slowly and her pretty pink lips started to glide up and down the shaft, sinking a little lower each time. I was fully hard now and throbbing a little against her tongue as it writhed and flicked at the underside. Not only that, but I was starting to leak and Jessica gave little muffled groans as my precum started to trickle across her tongue.
The pace quickened and soon those full lips were edging towards the base, saliva coating a good six inches at least. Not many women could handle my size but Jessica was taking it in stride, swallowing me down with effortless grace. Her ass was thrust up higher now and I couldn’t help but reach and grab it, squeezing the firm muscle that made up each rounded cheek. Another pass or two and she reached the bottom, her nose disappearing into my open pants as her lips touched the cotton of my boxer briefs.
“Aww, fuck!” I groaned, feeling my crown twitch somewhere deep in her oral cavity.
She held me there for a few seconds before finally retracting, leaving a faint pink mark on my underwear.
“Damn!” I exclaimed, shocked by what I’d just witnessed.
Jessica grinned back at me and threw a leg over my thighs, kneeling on the leather as she straddled me. An arm draped across my shoulders and a hand found the back of my head, fingers combing through my hair as she leaned in to kiss me. Her mouth was wetter now after sucking my dick and her tongue writhed against mine with greater ferocity.
Her free hand reached back and gripped my cock, and it was only then that I realised she’d gone commando for our little date. I felt myself pulsing harder at the thought of that alone, and I could feel the heat radiating from her naked crotch. She rubbed the tip against her slit, and it twitched as I felt her wetness; she was absolutely sodden.
Our mouths separated and a breathy gasp escaped her lips as she eased down onto it, swallowing my swollen crown. The first thing that struck me was how tight it was, and it really was hard to believe that she’d spat two kids out of there. The snugness of her pussy and the width of my cock seemed like a mismatch on paper, but the moisture lining her inner walls allowed me to slip in with ease.
Her left arm joined her right, and now both were wrapped tightly around my shoulders as she started to ride me. It was slow to begin with but she quickly gathered momentum, working that hot pink pussy up and down my pole. Her lips returned to mine and we moaned softly into each other’s mouths as she rode me harder. My hands migrated from her lower back and down to her ass, and I gripped two handfuls through the material of her dress. Soon that ass was bouncing off my thighs, generating clap sounds that were softened slightly by the twin layers of fabric. Each and every pass was executed to perfection, assisted by yours truly as I squeezed her ass, guiding her from bottom to top.
It was a great way to start and banging out here in the lounge like this felt very hot and spontaneous. But I was starting to find the limits of the couch a little restricting, and to give a woman like this the fucking she deserved I was going to need a lot more room. Without word, I pinned her body to mine, keeping a firm grip on her ass as I scooped her up into the air.
“Ahh!” she yelped, surprised by the sudden move.
I grinned and kissed her again as I walked us through the lounge and carried her to my bedroom, remaining inside her every step of the way. I crossed the threshold and finally pulled out of her, holding her bride and groom style for a moment before tossing her onto the bed.
“Oooh! You’re a bad boy, huh?” she said, purring like a cat as she laid back across the mattress, propping herself up on her elbows.
I returned a simple nod, still grinning from ear to ear as I quickly unbuttoned my shirt, kicking off my shoes as I tossed it aside. My pants were already coming down and I pushed them the rest of the way, keeping my eyes on Jessica as she watched me undress. My dick was still protruding from the hole in my boxers, and I pulled the waistband past my rock hard shaft, making it flop and down like a diving board, much to Jessica’s amusement. I pulled off my socks, eyes still fixed on my guest as she stared right back at me. Biting her lower lip, she enticed me towards the bed, beckoning me to join her with a manicured finger and one of the prettiest pairs of come-to-bed eyes I’d ever seen.
I climbed onto the bed and crawled on top of her, laying my naked form atop her fully clothed body. Well, not
quite fully clothed, but you get what I mean. The kissing resumed and a hand returned to the back of my head, the other already going for my cock. She wanted me back inside her straight away but I made her wait, taking a moment to enjoy that body that I hadn’t even seen in its entirety yet.
I moved to her neck, kissing her pale flesh as I undid the clasp on her dress, lowering it to her waist. I kissed past her collarbone and down her chest, taking a hard nipple between my lips and suckling like a famished babe. Gathering those perky mounds in my hands, I caressed them tenderly as I switched to the other, enjoying the light moans that I coaxed from between her lips.
The hand at the back of my head suddenly moved up to the top and a gentle push signalled that she wanted me lower. Clearly we were on the same wavelength, ‘cause that’s exactly where I was going next. I kissed slowly along her tummy, enjoying both her impressive muscle tone and the movements beneath me as I made her squirm. I hooked my fingers under her dress and tugged it past her hips. I knelt on the edge of the bed as I inched it down her legs, and soon that sexy dress had found a new home on my bedroom floor.
She spread her legs and I crawled up between them, getting my first look at the delicious pussy that I’d already been inside. And I’ve gotta say, it looked just as good as it felt- pink and puffy, and topped with a thin strip of fiery red pubes. The carpet matched the drapes, no doubt about that. Sliding a hand underneath her right knee, I lifted her thigh and kissed along it slowly- tortuously, even- finally settling at the gap in between.
My tongue came out and gave a long, deep, broad lick along the length of her slit, scooping up the nectar that had gathered there in copious volume. She tasted like heaven and the sweet, sweet flavour set my taste buds ablaze as I went back for seconds. Licking along her labia a few more times, I finally moved up to her clit, hooking my arms around her thighs and laying them on her stomach as I smothered her pinkest pleasure point.
I’ll never forget the sound she made when my tongue touched her nub- a loud carnal hiss that she propelled towards the bedroom ceiling as her head tipped back, face lit up in the throes of passion. She collapsed back onto the bed and her head hit the pillows, red hair spilling all around her. A hand reached down and gripped the top of my head, fingers vanishing between locks of hair as she held me in place, exactly where she wanted me. My tongue was quick and nimble, gliding across her clit in long, wet, fluid strokes. I could feel it throbbing against my tongue, and warm, sticky residue started to seep from her molten snatch, smearing across my lips and chin.
“Oh, God!” she groaned, her voice so soft I could barely hear her. “Fuck, you’re good at that.”
This I already knew but I never tire of hearing it, especially from a woman as gorgeous as she. My tongue rolled smoothly across her clit, and I continued at the same pace with which I’d started, seeing no reason to change a winning formula. Jessica was clearly loving every second of it and the tightening grip on the back of my head was a clear indicator of that. Her abdominal muscles began to tighten and the chorus of moans and whines that fluttered from between her lips were music to my ears.
“Oh, yes! Keep going. You’re gonna make me cum.”
Again, of this I was well aware, and having given her a sample of my God-given talents, it was time to bring it home. Swirling my tongue around her pulsing bud, this sudden change in technique proved decisive and my efforts were rewarded with a hot gush of fluids that drenched me from the nose down. Fingers dug into my scalp and her thighs tightened around me, not relinquishing their grip until the violent tremors rumbling through her had finally begun to recede.
“Wow!” she panted, her body sprawled limply across the king size bed. “I owe Erica a drink or something!”
“So do I,” I quipped, beginning the return journey across the expanse of her body.
I kissed along her torso, making a brief stop at one of her breasts before I reached my final destination. We kissed again and her tongue found mine, tussling with the instrument that had given her so much pleasure. I gripped my cock and pushed it up against her pussy, steering it inside her for the second time. She felt even wetter this time around and I slid right down to the balls with the slightest push. Our lips came apart and she uttered another soft moan as she felt me throb inside her. She wrapped an arm around my neck while the other went down to my ass, clutching my tight buns as I started thrusting.
I fucked her slowly, rolling my hips in a steady rhythm and delivering hard, unhurried thrusts into the woman beneath me, making sure I gave her evey inch. A hand clawed at my upper back, the other digging into my buttcheeks as they moved back and forth, propelling me deep inside her. Occasionally we’d kiss or she’d nuzzle into my neck or I into hers, every action accompanied by a pair of impassioned moans.
Her hand moved up from my ass, joining the other at my shoulders and we separated slightly as I propped myself up with my arms, starting fuck her at a quicker pace. Her head stayed buried in the pillows, allowing me to see the expressions on her face, those gorgeous features reacting to each and every thrust. I could feel her arms tremble as they locked around my neck and it was clear that she wasn’t used to a dick of my size. But the actress took it with aplomb and there was nothing but pleasure plastered across her face as I rowed in deep, sheathing myself to the hilt.
Her pussy was warm and receptive, gleefully accepting each stroke and responding with an appreciative squeeze. She felt amazing and already I was starting to notice my crown twitching as it vanished inside her, my balls churning with a cumload that had started gathering from the first moment I saw her.
Laying down onto her once more, I wrapped my arms around her back, taking her with me as I rolled back onto mine. Now we were in the cowgirl position, just as we were on the couch, except this time I was in control. Keeping my arms folded tightly around her, I held her body against mine and our lips found each other once more as I drove my dick up inside her. The thrusts were harder now, coaxing sounds of greater volume and pitch to spew from between her lips.
“Oh, fuck!” she yelped, staring down at me with wide, unblinking eye contact as I bounced my ass off the mattress. “Yeah, yeah, yeah! That’s it! That’s how I fucking want it!”
My hands moved down to her ass, enjoying the flawless shape as I banged her from beneath. The tryst was altogether louder now. Not just the yelps from Jessica, but the smacking together of bodies, the squeak of the mattress and the rattling of the headboard had all kicked up another few decibels. It was raw now, sweaty and intense, and neither of us could hide the pure lust that we felt for the other person. Every so often our lips would engage, moans merging as one as our mouths locked together. Or I’d move a little lower to latch onto one of her tits, guzzling with greedy intent.
Her body was tensed all over, and nowhere was that more evident than inside her vagina, her inner walls seeming to grip me tighter each time I thrust inside. It drove me even wilder, and the harder her pussy clenched, the harder I fucked her. Every thrust sent my dick in deep, and I could tell from the pitch of her voice and the look of ecstasy etched across her face that I was hitting all the right spots.
“Oh, God!” she squealed, her sweaty face mere inches from mine. “Yeah! Keep going! I’m gonna cum!”
One more thrust and she delivered what she promised, screaming toward the heavens and squeezing my dick harder than ever as a powerful orgasm rocked her entire frame. I wasn’t far behind and my dick was throbbing so violently now that putting my intentions into words was entirely unnecessary. Jessica knew exactly what was coming and her light and breathy tones enlightened me as to exactly where she wanted me to do it.
“Cum in me,” she said softly, those three simple words a delight to the ears.
We hadn’t discussed it prior but I guessed she was either set or at a stage in her life where protection was no longer required. It was hard to believe that a woman that stunning could be menopausal, but at 45 it was definitely possible.
Pinning her body against mine, I buried myself to the balls, finally giving into the sensations that had been building within me since minute one. I felt myself stiffen even harder and then I unloaded, dumping an impossibly thick load deep into her piping hot pussy. My eyes never left my guest’s and the look of delight on her face when she milked my gonads dry was one I will never forget.
Her hands went to my face and we kissed several times as I remained inside her, cum starting to drip down my shaft. Recovery time was minimal and all it took was a quick polish of my cock from Jessica’s mouth to instigate a second session that was just as passionate as the first. We fucked twice more before we finally ran out of energy, and we passed out together as I cradled her in my arms.
*
I awoke first the following day, my blurry morning vision slowly coming to focus on a mass of tangled red hair. I rolled over onto my back, eager to take care of my morning breath before the goddess beside me roused from her slumber. Morning sex was popular among my guests so I kept a bottle of mouthwash by the bed. I sloshed a refreshing mouthful around my stinking trap and spat it into an empty cup.
The sound of the bottle plonking down onto my nightstand woke Sleeping Beauty and she turned to me with a tired groan. She still looked as stunning as ever, even in the remnants of last night’s makeup. Her eyes fell upon me and she gave me a lazy smile.
“Morning,” I said.
Even an angel such as her wasn’t immune to the scourge of morning breath, so I retrieved the bottle from the nightstand and offered her a minty gurgle. She rinsed her mouth, and I offered her the cup to spit into. She put her hand to her mouth and sniffed her breath, happy that the crisis had been averted.
“Good morning,” she finally replied, laying a fat smacker on my lips. “Did you sleep well?”
“Like a baby.”
“I should think so after the night we had. By the way, mouthwash by the bed.” She did a chef’s kiss. “Ingenious.”
“Professional necessity,” I said with a grin.
“Oh, yeah? I thought you were a masseur, not a dentist,” Jessica replied, still committing to the fantasy, so many hours later.
“Oh…er…yeah. Sometimes clients like to have a rinse after a massage. Their mouths can get kinda dry, with all the candles and incense and stuff.”
“I see,” she said, returning a grin that was clear in its meaning.
Good save. “Speaking of clients, are you working at all today?”
“Uh uh. All yours.”
“All mine, huh,” she said, tracing a finger across my chest. “So you’re not in any hurry to…say, get out of bed then?”
“I’ve got all the time in the world.”
And with that we got straight back to it. Our minty fresh mouths mingled as one and I rolled on top of her, pressing my body to hers. I was already sporting a semi from that good morning kiss, and my half-mast member slid into the gap between her thighs, rubbing up against the slit of her pussy. I retrieved my tongue from down her throat and set off on the same journey down the span of her body that I had taken the previous evening. Except this time I took the scenic route- down past her right breast, across her ribcage and over her hip.
Pushing her leg up, I licked along the bottom curve of her ass and up to her slit, gathering the morning dew with a long, slick swipe of my tongue. Her pussy was nice and fresh, having showered the night before, but all the action it had seen the previous evening had left it a little pungent. But I didn’t mind one bit, and happily feasted on that little slice of heaven like it was the last thing I’d ever eat.
Her hands came down to my head, clearing a familiar path through my hair as she gripped me tight. My tongue settled on the nub of her clit, swirling around it in concentric circles. Jessica responded to this second bout of oral in much the same way as she did the first. Sharp, laboured breaths puffed out from between her lips, and it took just the briefest display of my oral prowess to coax drops of gooey arousal from beyond her labia.
My hands were rested on her toned little tummy, gently caressing her feminine abs. Yet there was another use for my upper extremities that I was sure would better suit the both of us. Popping my lips briefly from around her clit, I slid two fingers into my mouth, wetting them with saliva. Teasing her slit with the tips of both digits, I guided them in with a gentle push, sinking right down to the knuckle. Curling them upwards in a hook-like fashion, I returned my mouth to her clit, whirling it around her swollen nub with renewed and relentless vigour. This new move elicited quite a reaction, and Jessica’s head jolted up from the stack of pillows, flinging auburn locks in every direction.
“OH!” she yelped, letting me know, in no uncertain terms, that her g-spot had been located.
I repeated the action on an endless loop, hooking my digits towards her navel and prodding at her hidden pleasure spot. She was leaking copiously now, and my fingers were glistening with her juicy arousal as I sunk them into her coochie. Moans and groans were pouring from her lips and her hands began to shake as she clawed at my thick locks of hair. I had her on the edge, teetering on the precipice of another mind-blowing orgasm.
I buried my fingers inside her one last time, massaging her g-spot with the tips as I tongued her aching clit. Moans turned to screams, and I didn’t stop licking until she reached her crescendo, following it up with a pleasing encore of sharp, heavy breaths that gradually returned to their normal rhythm.
I emerged from between her thighs and kissed her panting mouth, my lips still sticky with arousal. Our mouths sealed shut and she tasted her sweet juices as our tongues did their familiar dance. I pried my lips from hers and she gave a cute little squeal as I rolled her up onto her side, making her the little spoon. A little fumble down below and I was all up inside her, filling her right from the off.
I wrapped my arms around her and held her against me, our arms entangled as I thrusted slowly, feeding her every inch I possessed. She turned her head and I leaned over her, kissing her ravenously. She held my hand to her chest and I could feel her heart beating harder, muffled groans getting louder as she directed them into my mouth. Her legs so close together made her pussy even tighter and I could feel her squeezing me each time I thrust inside.
I wasn’t going to last five seconds in that position, so I lifted a leg and held it upwards, using her thigh for leverage as I pulled myself into her. I could go at her harder now and the thrusts started to quicken as I pointed her leg towards the ceiling, clawing at her inner thigh. Brushing away her hair, I nuzzled into Jessica’s neck and sucked on her pale fresh, being careful not to leave a mark that would incur the wrath of her husband. She was mewling incessantly now, and I enjoyed the increase in volume that accompanied each thrust.
Soon I was giving her everything, slamming into her with the kind of tireless energy that only the morning horn can provide. The bed squeaked and rattled, and the soundtrack was completed by a series of deafening smacks as my thundering pelvis clapped against her ass. Jessica’s face sunk into the pillow beneath her and she unleashed an animalistic scream that was muffled by the expensive stuffing. Her body was on fire and I could feel the inferno spreading through her body as I pinned it against my own. She was about to erupt and so was I, and I sought to squeeze in one last position before the quake of orgasm shook us both to the core.
Moving my hands to her waist, I held her tight and flipped up onto my knees, bringing her with me as I switched from spoons to doggystyle in a single, seamless motion. Gripping her hips, I drove into her with all I had, watching her asscheeks ripple with each thrust. The switch in stance delighted her, and matted red hair swished through the air theatrically as she looked back at me, lust burning in her bright blue eyes.
“Yes, come on! Fuck me! Gimme that good hard dick!”
I moved my hands down to her ass and dug my fingers into her cheeks, feeling them jiggle as I clattered against them. My hips were hammering now, balls swinging back and forth and cannoning against her clit. Those very same balls were crying out to be emptied, and I wanted nothing more than to bury myself to the root and explode into her womb. But I was providing a service here, and the customer’s needs always came first. I wasn’t gonna cum until she did.
My hands returned to her hips and I folded my arms around Jessica’s torso, pulling her up until her body was flush against mine. I put one hand to her throat- not applying any pressure, just holding it lightly- while the other went to her clit, strumming it wildly as I continued to thrust. The extra stimulation had her screaming louder than ever and my motions slowed to a series of steady, hard thrusts that sent all eight inches rocketing into her vagina.
She was trembling in my arms now, her body going limp as I drove my dick into its furthest reaches. She threw her arms back and gripped the back of my head, holding on for dear life as her body took the brunt of each slam. The pleasure was spreading and I could almost feel the waves of euphoria coursing through her like electric jolts. Sweaty red hair whipped across my face and my mouth muffled the last few throaty squeals as she turned back to face me, locking her lips against my own.
Sinking to the base one final time, I kept it deep inside her as the pleasure took over, her body lost to the powerful sensations now engulfing her every inch. Squeezing me tighter than ever, I lost all semblance of self-control and Jessica was still in the midst of climax as I finally let loose, firing an ungodly volume of bubbling jism deep into her balmy insides. The squeals faded and my grip on her loosened, our tongues slowing from a fierce grapple to a soft embrace, accompanied by panting breaths and moans from myself and my guest alike.
Cradling her lightly in my quivering arms, I returned us to our previous position. We laid like that for a while and I remained inside her as I held her in my arms, our fingers gently entwined. Her tousled red mane hung over one of her shoulders and I left soft kisses on the back of her neck. Neither of us spoke, both happy to bask in the afterglow of breathtaking, passion-feuled sex. What a way to start the day!
After several minutes, our bodies began to regain function, and I suggested we take a shower to wash away the various residues. Jessica agreed and after one last tired kiss, I leapt up off the bed, thin drops of cum dripping from my still-hard cock as I headed for the en suite. I went inside and closed the door, emptying a bladder that was full to the point of bursting. I opened the door, signalling to Jessica that she could join me whenever she wanted, and fired up the electric toothbrush.
Moments later, hands were on my torso and my guest's lovely chest was pressed against my back, kisses delivered to the nape of my neck. I finished brushing and rinsed thoroughly, turning to face her and returning kisses with my now very mint-tasting mouth. I lent against the sink and she laid her arms across my shoulders. We kissed several more times then I got in the shower, leaving the toilet and sink at her disposal.
I closed the glass door and turned on the water, fiddling with dials until I found the right temperature. The water pummelled me, its soothing warmth reviving my aching frame. I soaked my sweaty hair, exchanging grins with Jessica as she brushed her teeth. She signalled for me to face the wall and I did, washing my hair as she perched on the toilet seat. Rinsing out the last of the suds, I heard the door squeak open behind me and in just a few seconds those dainty, toned arms were wrapped around my torso once more.
Kisses were left on my back and shoulders as I doused my body in shower gel. Jessica assisted, spreading the fragrant foam across my tummy and pecs, making sure my dick got a thorough going over. My morning wood had just begun to soften when she started stroking, lathering my member from bellend to base. I turned to face her and a hand glided through my slicked back hair as we started making out. The other found my cock and the jerking commenced, restoring my full rigidity in a matter of moments.
Our mouths stayed together as I gripped onto her ass, hoisting her into mid-air. I slid my hands to her thighs and held her against the glass, leaving a back and ass print in the condensation. Her right arm joined her left, linking securely around my neck, and I took hold of my cock, guiding it into her as I kept her suspended. No slow build up this time, and despite having cum not 15 minutes ago, I was giving it to her hard from the very beginning, every thrust going straight to the hilt. Her lips left mine and she moved to my ear, directing sharp breaths into my eardrum as she nibbled at the lobe.
She gripped me tight, both inside and out, and her pussy was as receptive as ever to the eight inch log being propelled into her darkest depths. My dick was throbbing and I didn’t let the painful tingling of my latest climax stop me from giving this woman the fucking she deserved. Water beat down on my back, pounding the muscles already under siege by her manicured nails.
I took a few steps back, slacking my grip slightly and allowing Jessica to swing back, leaving some space between her body and mine. Her fingers interlocked around my neck and she clung to it precariously, leaning back so far that she was practically hanging from my shoulders. Now the water was raining down between us, soaking us both in equal measure. The thrusts continued and I watched those perky tits jiggle up and down as I slammed into her, driving into her gorgeous body with all the force I could muster.
I’d given her countless orgasms since she’d arrived at my place and was well on my way to claiming another when an idea struck me. Clutching the shower head, I removed it from the bracket on the wall and held it to her clit. Jessica clearly approved and she tipped her head back, staring at the ceiling as high velocity water was fired at her aching nub.
“Oh, WOW!” she yelped, squealing in delight as I turned the shower head into a makeshift sextoy.
My grip loosened and with just a single arm supporting her entire frame, I was unable to go in on her with my usual pace and power. But it mattered not, and the water jetting against her clit had whipped her into such a frenzy that she probably wouldn’t have noticed if I’d slipped out altogether. She came in seconds, screaming at the top of her lungs and squeezing my rod so hard I thought it was going to break off at the stem. I gave her a few more thrusts just to remind her I was there, then lowered her to her feet.
I returned the shower head to the bracket and Jessica grabbed a bottle of shower gel, still panting heavily as she dropped to her knees. She looked up at me with a filthy grin, squeezing a thick dollop of gooey blue liquid into the palm of her hand. Rubbing her hands together, she worked it into a lather before winding her foamy fingers around the width of my rod. One hand clutched to my hip, the other slid smoothly along the length of my shaft, the slick coat of shower gel assisting in a handjob technique that I had no doubt was world class to begin with.
Jessica gazed at me with gleeful anticipation, eagerly awaiting the violent eruption that was destined to follow. She didn’t have to wait long, and a few more wet, soapy jerks was all it took to drain my swollen gonads for the second time that morning.
“Uhh! Fuck!” I yelled, throwing my head back and getting a faceful of water as a long, thunderous orgasm hit me like a ton of bricks.
It wasn’t as explosive as the first, but it was still more than enough to leave a hot streak of spunk plastered across Jessica’s face.
“Mmm, yeah!” she purred, grinning at me as she stroked my rod. “That’s what I wanted.”
She put her lips to the tip of my prick and tongued at the slit, licking up the final few drops. Rising to her feet, she stepped under the shower head, letting the water wash away the cum from her lips and chin. I gave her a kiss and stepped out in search of a towel, leaving her to finish up in the shower. I dug out a couple of towels from the linen closet, wrapping one around my waist and leaving the other on the rack in the bathroom.
I stepped back into the bedroom and closed the door behind me, drying myself with the towel. I was nearly dry when the pitter patter of the shower came to a sudden halt. Jessica emerged from the steamy en suite, running the towel through her soaked red hair.
“Ah, that’s better,” she said, gathering her damp locks over one of her shoulders.
“Feeling refreshed?” I asked, returning the towel to my waist as if I rifled through my closet.
“Mmhmm,” she replied, coming up behind me and pressing her still wet body against mine. “And re-energised.”
Lips pressed against the nape of my neck and a soft pair of hands roamed across my torso. A slight tug at my towel and it hit the floor, landing in a heap at my ankles. She dropped slowly to her knees, kissing along the length of my spine as she took my cock in her hands, fingers curling around the shaft. It had just gone soft for the first time that morning, but Jessica soon took care of that. By the time her knees touched the carpet, my dick had been restored to its former glory and was jutting from my groin like a long steel girder.
Hands on my hips were my signal to turn, and my dick flopped about every which way as I spun around to face her. Gripping my cock at the base, she gazed up at me with those seductive blue eyes as she wrapped her lips around the head. She sucked me slowly, sensually- which was just as well given the tender state of my genitals. After two such powerful eruptions, I wasn’t sure I’d be able to cope with much else, and every dose of pleasure came with a little side helping of pain as she slid those plump lips up and down my tender shaft.
A hand led the way, stroking and jerking with all the pressure I could handle, while her lips followed closely behind, soaking my shaft in saliva. Before I knew it, her hand was back at the root, the tip of my dick pushing deep into her oral cavity. She moved her hand to my hip and her lips went the rest of the way, sliding down smoothly until they puckered at the base of my shaft.
“Ugh! Shit!” I groaned, my tender helmet twitching against her tonsils.
Jessica held me there for as long as she could, sucking out what little precum my overtaxed balls were able to generate. I could feel the warm spit sloshing around her mouth, soaking my every inch as I throbbed against her tongue. Soon that throbbing was more than she could handle and her gag reflex finally got the better of her, just when I was starting to wonder if she had one at all. She pushed against my hips and her lips made a hasty retreat, sliding up the shaft until the crown popped out from between them.
Taking it in her hand, she gripped it tight and started stroking, showing little sympathy for my delicate state as her knuckles shuffled from bottom to top. Pointing it skyward, she turned her attention to my scrotum, slowly starting to inflate after being utterly voided two times over. Her pouty lips enveloped a testicle and she sucked it seductively, switching to the other and dousing both gonads in spittle.
A ball fell from between her lips and she rose to her feet, kissing me hard on the mouth. She threw her arms around my neck and practically leapt up onto me, wrapping her legs around the small of my back. Holding her up with a hand on her ass, the other went straight for my cock, steering inside her for the third time that morning. The grip of her pussy sent shudders down my spine, and it soon became abundantly clear that a hole that tight was no place for a dick as delicate as mine. But I didn’t let that stop me, and honestly, I’d still have found a way to fuck her if it had been lopped off at the base.
Holding onto her asscheeks, I guided her along the length of my shaft, easing her down it slowly until there was nowhere left to go. Our mouths divided and I held her there, enjoying her change in expression as I bottomed out inside her. The intense snarl of passion she’d worn when she jumped up onto me had given way to a wide-eyed gasp of stunned disbelief, and it was clear that, even after five bouts of tempestuous sex, she still hadn’t gotten used to my size.
The gasp turned to a smile and I kissed her once more, proceeding to fuck her the way she wanted, the way she desired. This time I let my arms do the work, gripping onto her peachy buttocks and sliding her along my pole. It started slow and our mouths stayed together as I pulled her up to the ridge of my crown, holding her there for a few agonising seconds before I lowered her back to the hilt. Her pussy remained snug and each embrace of her soft inner walls seemed tighter than the one before.
The pace quickened and soon my biceps were getting quite the workout as I lifted and dropped her repeatedly, impaling her on all eight inches. She threw her head back dramatically, damp red locks tumbling down towards the floor as an eardrum-rattling scream flew forth from the bowels of her throat.
“Oh, GOD! Yes! Like that!”
The reaction pleased me and I repeated the action for quite some time, eliciting a similar response with each deep plunge to the balls. My arms began to tire, but luckily for me she was almost there, closing in fast on yet another tumultuous orgasm. Fingers digging into her cheeks, I pulled her into me and held her there, practically dangling off my long flesh pole. Her face remained skyward, screaming in ecstasy as her body was overcome by violent convulsions. I held her tight as she came, allowing the gush of fluid to wash every inch of my junk.
The grip on my cock had tightened to intolerable levels and as the final notes of her deafening scream were propelled towards the ceiling, I turned her solo into a duet, unleashing a roar of my own as I detonated inside her. By this stage my ejaculate was pretty much nil, but the orgasm that accompanied it was no less intense, rumbling through my body like an earthquake.
Jessica sighed, wettish locks spilling about her shoulders as she brought her head up, a satisfied smile stretching from cheek to cheek. We kissed as I let her down and I returned to the closet, finally picking out something to wear. It was a warm day and I’d already worked up a sweat after my morning shower, so I went for a tank top and shorts.
Jessica dried her hair and hung the towel on the rack next to mine. She asked me if I had a t-shirt she could wear as she didn’t have a change of clothes.
Still in full on fantasy mode. Actually, it was a good job she brought it up ‘cause the fantasy I was supposed to be fulfilling had completely slipped my mind. I dug her out a t-shirt and she pulled it on. She didn’t even have any underwear to change into, so as far as her outfit went, that t-shirt was the full extent. She did her makeup quickly with the few cosmetics that she had in her handbag and we went to the kitchen to get some food.
Breakfast time had been and gone so we skipped straight to lunch. I fixed us a salad with the chicken I had leftover from the stir fry, and Jessica poured us both a glass of iced tea. We fooled around a little in the kitchen while I sliced up the veggies, and knowing she had nothing on under that t-shirt made the urge to pull her up onto the worktop and pound it out right there and then extremely hard to resist. But I managed it, just about, and we took our plates outside to eat in the afternoon sun. She still didn’t have any panties on, but my home is extremely secluded so there was no danger of one of my neighbours spotting a glimpse of an Oscar winner’s hoo-ha.
We ate and talked, and she asked me a few more questions about my fake job. I had no idea if the responses I gave gelled with the ones from the previous evening, but I answered them as best I could. We started talking about massages and Jessica informed me of a particularly relaxing one she’d had a few weeks before.
“Do you get massages often?” I asked, piercing a cherry tomato with the prongs of my fork.
“Occasionally,” she replied. “My job’s pretty stressful and they’re a great way to unwind and relieve some tension. I’d like to get more but I don’t really have the time.”
“Well, like I said, my schedule is free today. Maybe we could relieve a little tension right now.”
Jessica chuckled. “Isn’t that what we did last night?” She took a swig of her drink. “And this morning.”
“True,” I said with a grin. “Then maybe we oughta give those muscles of yours a little TLC. Shift some of that lactic acid.”
“Hmm, well I don’t have any cash on me. Unless, of course, you accept types of payment,” the actress declared, a bare foot running along the length of my shin.
“I’m sure we can work something out.”
And with that we went back inside, returning our plates to the kitchen on our way to my massage room. I led her inside, lit a few candles and burned some incense, closing the window shutters to create the perfect atmosphere.
“OK,” I said, patting the padded top of my massage table, “lose the t-shirt and climb aboard. Would you like a towel?”
Jessica laughed, pulling off her (my) t-shirt with an impish grin. “Don’t really think that’s necessary, do you?”
“Probably not.”
I plucked a hair band from a drawer on my dresser and tossed it to her. Such items were essential for any good masseur. Even a pretend one like me. Jessica tied up her hair and climbed up onto the table. She laid on her front to start with, making use of the face hole that had been cut into the padded surface.
I fetched a bottle of oil from the dresser and poured out a palmful, warming it with a rub of my hands. I started at her feet, smearing oil across each of her soles and using my thumbs to apply some pressure. My hands worked wonders on her dainty feet, undoubtedly aching after years teetering up and down red carpets in all manner of perilous stilettos. The pressure clearly met her approval and a breathy coo of appreciation tumbled down to the massage room floor. A trained masseur I am not (despite what I’ve been telling Jessica for the past 20 or so hours), but I’ve given my fair share of rubdowns over the years and have learned a thing or two along the way. It’s a service I provide at no extra cost, and my guests enjoy it greatly.
I left her feet behind and moved up to her calves, shining them thoroughly with the scented oil. The backs of both legs were perfectly toned and my hands enjoyed the layers of muscle as they glided across her silky smooth skin. After her calves came her thighs, which is where the things began to heat up. Literally. I ran my hands along the creamy insides, feeling the warmth start to radiate from the space in between. The tips of my fingers edged closer to the apex, stopping just short of the heat source and drawing a groan of frustration from my ‘client’. I enjoyed teasing her and moved up to her ass, watching her squirm against the tabletop.
“I’m going to have to ask you to remain still, please, ma’am,” I said with a grin, now playing the part of an on-duty masseur, within my part as an off-duty one. A role within a role. Real wheels within wheels shit.
Jessica raised her head and shot me a playful glare. I disarmed it within an even more playful smile, getting one in return as she sunk back into the face hole.
“And keep your head against the table, please. Thank you.”
I was pushing it now and received a swat to the back of my thigh as I continued the massage.
Her ass was a delight. I’d gotten my hands on it numerous times by this stage, of course, but I gained a new appreciation of it in my role as masseur, being able to enjoy its feel and shape for prolonged periods of time. It caused a stir in my nether regions like never before and there was a noticeable lump in my shorts as I moved to the head of the table. I rounded out the first half with her shoulders and neck, then asked her to flip over.
Jessica rolled over onto her back and her lips curled up in a grin as she spotted the semi stretching the fabric of my shorts. I refilled my hands with oil and returned to her feet, moving up her shins to the tops of her thighs. Her legs were slightly parted and I teased her again, in much the same way as I did before. My hands slid along her inner thighs, inching tantalisingly close to her vagina but not
quite touching it. I had no idea I could be so callous.
I returned to the head of the table and got to work on her shoulders, quickly moving down to the pert twin mounds of her breasts. I’d teased her long enough now, and honestly they looked too good to resist. They didn’t feel too shabby either, and I spent more time there than any real massage client would have deemed appropriate. But I needn’t have felt guilty, for as my hands continued to squeeze at her fabulous breasts, a dainty paw rose from the tabletop and responded in kind, grabbing at my dick through my shorts.
“Ma’am, please return your hand to the tabletop, or I’m afraid I’m going to have to ask you to leave.”
She grinned at me, placing her hand back on the table, and I stifled one of my own, doing my best not to break my character within a character. Finally managing to pry myself from the lure of her chest, I moved down to her midriff, being sure to lean over her as far as I could as I ran my hands across her ribcage. Now my cock was mere inches from her face, covered only by two thin strips of fabric. Jessica’s lips came open and I felt her tongue slide across the tip of my bulge.
“Ma’am, this is a professional establishment, and I do not think that kind of behaviour is appropriate.”
I looked down at her and her smirk had turned into a giggle. This time I couldn't keep from grinning right back at her and I kept watching as she licked along the length of my shaft. I went around to the side of the table and she flashed me a cute little pout as my dick moved out of her reach. But she wasn’t disappointed for long and as I felt and caressed her toned little tummy, a hand finally,
finally inched down between her thighs and started rubbing her pussy.
Her mouth opened and a sharp hiss of satisfaction fluttered out into the ether. I slid my fingers along her slit, feeling the wetness, before settling on her clit, strumming it with two twin digits. She went for my cock again and this time I didn’t stop her, happily allowing her to feel me up as I frigged her throbbing clit. My dick was fully hard now and properly recovered after our much needed break. Not content with merely feeling me up through my shorts, Jessica reached under the waistband, freeing it from the constrictive garments. Winding her fingers around the shaft, she jerked me steadily, cooing and groaning as I returned the favour.
I looked up at the clock on the wall. It had just gone 3pm; her time was almost up. But there was no way I was letting her go without tasting her one last time, and I climbed up onto the table so I could finish her properly. Kneeling on the edge of the massage table, I pushed her legs a little further apart and all but dove in between them. The long and teasing massage had worked her into a lather, and my third helping of pussy came with an extra dose of sweet and creamy sauce. My tongue slid along the length of her slit, mopping up the delicious goo that tingled each one of my taste buds. Then, I focused on her clit, smothering it with my lips and performing a deep tissue massage with the tip of my tongue.
I wrapped my arms around her thighs, a hand coming to rest on her midriff, feeling her muscles clench, a thumb trailing softly through her thin batch of pubes. I licked her studiously, with intent and purpose, determined to make my final bout of oral pleasure the most explosive of the lot. Jessica responded in the manner I’d come to expect, a steady refrain of soft, satisfied moans pouring out from between her lips. A hand clutched the edge of the table, manicured fingers scratching at the padded surface as the other took up its usual position at the back of my head. Fingers scoured my hair, grasping a palmful of locks to ensure my mouth remained right where it was.
My tongue was a tornado, twisting and twirling around her stiff nub of pleasure, and I could feel her arousal start to coat my lips and chin. Soon, the telltale sounds of impending orgasm were flooding my eardrums, a delightful cacophony that I could never grow tired of hearing. Her moans grew louder, increasing rapidly in both volume and pitch. Her breathing quickened, and I enjoyed the sight of her oily tits rising and falling as I tongued her towards the inevitable.
One final swirl of my tongue and the dam burst in spectacular fashion, a hot rush of fluid pouring across my tongue. It tasted delicious and I didn’t stop licking until I’d extracted every drop. Her hand came free from the back of my head and her arms hung limply off the side of the table as she lay there in a state of bliss. She remained like that for close to a minute, whispering thankful exaltations to whichever higher power had brought her to my front door.
“Oh, my God! Sweet Jesus!”
I hopped down off the table, sporting a sticky grin as I emerged from between her legs. Jessica willed herself up from the surface and scooted along to the edge of the table, throwing her arms around me in a way that was now so familiar. Our mouths embraced and her legs curled around the small of my back, ankles locking just above my ass.
I unbuttoned my shorts and let them fall to my feet, kicking them aside as I hoisted her into the air. I took hold of my cock and lowered her onto it, entering her suspended frame for the third time that day. Standing was quickly becoming our position of choice and the two of us had all but mastered the art of aerial intercourse. Positioning my hands beneath the tops of her thighs, I gave my biceps a further sculpting as I worked her up and down my dick. Each ascent was immediately followed by a death-defying plunge to the hilt, and she screamed out in ecstasy as I packed her pink pussy to the brim.
I kept this up for as long as I could, sliding her along my shaft, almost jerking myself off with her pussy. But her walls were too tight, her insides too warm, and soon the urge to slam into her with everything I had was simply too great to ignore. Moving an arm to the small of her back, I proceeded to do just that, holding her up with the other as I started thrusting. Jessica swung back in my arms, just as she had in the shower, her hands around my neck as I drove up inside her.
We both knew this was our last fuck (probably) until she could come back, so both of us were giving it our all. Jessica was on top of her game, gleefully inviting each pelvic slam. Her eyes stayed glued on mine and each thrust was met with an appreciative squeal, letting me know just how good it felt when I was inside her. Her hair remained tied, robbing her of the angelic quality it provided when it tumbled about her shoulders. But she still looked stunning all the same, and I was able to focus solely on the lust in her eyes and the words on her lips, without the distraction of her flowing red mane.
“Yes! Come on, baby! Give it to me. Yes, baby! Just like that!”
Nails dug into my neck as her arms began to shake, a look on her face of pure, unadulterated bliss. Another orgasm was close at hand, the latest in a long line of earth-shattering climaxes, each more powerful than the last. I buried myself to the balls one final time, remaining there as I felt her cum. Previous orgasms in this position had resulted in her throwing her head back, directing loud screams towards the heavens. But this time she remained upright and her eyes never left my own, allowing us to share the moment when her climax hit her. Her body quaked in my arms, and her grip on my neck loosened, leaving herself at my mercy. I moved an arm towards her shoulders and held her against me, the last few tremors reverberating against my chest as the waves of orgasmic pleasure finally began to subside.
We took a moment to catch our breath then I walked us back to the massage table. Spinning us around, I parked my ass on the edge and scooted back, bringing the redhead with me. Her thighs rested against my own and I kept my arms around her to take her weight. Her legs stretched out and she crossed them together behind me, arms around my neck, dick still embedded inside her. Our mouths connected and her fingers combed through my hair as her writhing tongue explored the inner contours of my mouth.
We remained this way for several minutes, bodies entwined, kissing each other with untamed passion. Then, she hopped onto her feet and my hands went to her ass, offering assistance as she started to ride me. The kissing continued, now accompanied by a duet of amorous moans that were swapped back and forth from my mouth to hers. Our lips came apart as she rode me harder and my hands moved up to her hips, allowing her juicy ass cheeks to clap against my thighs.
Breasts jiggling, I caught a stiff nipple between my lips, suckling like a babe in arms. Switching to the other, I licked all across her chest and back to her mouth, kissing her deeply as she bounced up and down my dick. The massage table creaked and shook, wobbling so violently that I thought the legs might buckle. Our tongues untangled and she gazed into my eyes, cooing instruction as our bodies collided.
“Lay back.”
I did as directed, happily relinquishing all control and permitting her to use me however she pleased. Returning her knees to the padded surface, she leaned back slightly, balling her hands into fists and planting them behind her feet. Now she could ride me even harder, those strong thigh muscles powering her up and down my shaft. The extra tension only tightened her further, and the pressure she applied as she sank to the base was almost too much for me to handle. My head wedged into the face hole and I had no choice but to stare at the ceiling, powerless to resist as this sexy older woman made my dick her personal property.
I was throbbing uncontrollably now, blood surging through my shaft at a mile a minute. Jessica noticed and her squats suddenly came to a halt, her ass sitting flush against my thighs so she could feel me pulsing inside her. I pried my head from the hole in the table and looked up at the woman above me, a truly glorious image awaiting me that will be burned into my memory forever. Her lips were puckered in a gorgeous, seductive pout. Real old school sex kitten stuff. The kind Marilyn Monroe would have been proud of. While her eyes gazed at me from beneath her fluttering lashes, informing me all on their own that she was going to milk my testes dry.
And she was going the right way about it. Hands rested on my thighs, she started to grind her pelvis against my own, her insides squeezing me like a soft, warm vice. My body tensed all over and my crown started twitching in her skinny pink passage, yearning to fire its goo into her darkest recesses. But when it came to orgasms, I adhered to a strict policy of ladies first. I didn’t cum until she did. So with that in mind, I reached shakily for her furry red groin and started rubbing my thumb against her clit. That set her off almost immediately and her eyes clamped shut as yet another fiery orgasm ignited from deep inside her.
Her pussy clenched tighter and all it took was the slightest squeeze to tempt out the load that had been swirling around my balls since the start of the massage. My head fell back into the face hole and I held her tight, pinning against me as I filled her trembling body to the gills. An ear-splitting squeal flew forth from her pouting lips and I responded in kind, emitting a deep, savage roar that almost shredded my vocal chords. The break in play had restored my fire power, and I spewed into her insides for what felt like an eternity, filling her womb with every last drop.
Jessica slumped forward, and a simple ‘ugh’ was all she could bring herself to say as her worn out body collapsed on top of my own. Hardly Shakespeare, but it was more than I managed to get out. In fact, I’d gone off so hard I could barely think straight, and it took all the brain power I could muster just to wrap my arms around her back.
Jessica flopped down onto her side, laying an arm across my chest and we found it within ourselves to brave an occasional kiss. But mostly we just laid there, listening to each other breathe as we basked in our collective warmth. Nothing needed to be done. No words needed to be said. Which was just as well, ‘cause I was in no position to do so. How long we stayed like that, I couldn’t say for sure, but I knew it would be a while before either of us could even contemplate any kind of movement.
Eventually, we willed ourselves off the massage table and back to my room for a shower. Did we have sex in there again? I’m not at liberty to divulge, but suffice it to say there was a lot more than just massage oil that had to be washed from our bodies by the time we were done. We towelled ourselves dry, and in what was quite possibly Jessica’s staunchest commitment to her sexual fantasy, she slipped back into the very same dress that she’d worn the night before. She gathered her stilettos and I led her across the hall, giving her a hug ‘goodbye’ (she’d be back in a minute for the rest of her things) as we stood in the doorway.
“Thank you for a great night,” she said, her arms around my shoulders. “And a great day.”
“Thank
you for a great night and great day,” I replied, my hands sliding slowly to her hips.
“Call me?” she asked, giving her eyelashes one last flutter. “That was too good for a one-and-done, right?”
“Just try and stop me,” I said and my hands went to her cheeks, giving Hollywood agent Jessica Chastain a lingering farewell kiss.
I stayed in the doorway as she headed for her car, even opening the front door for show as she blew me a kiss and waved goodbye. I waved back and went back inside, waiting in the hallway as I closed the door. There was a knock a minute later and I opened back up.
“Hi!” said Jessica,
finally returning to the world-famous movie star that she’d been when she first arrived. She took my face in her hands, landing a big, wet kiss upon my lips. “That was amazing.
You were amazing.”
“So were you.”
“Oh, I know,” she said, that familiar grin still tickling her lips. “Help me with my things?”
“Of course,” I said, and we went to ‘her’ room (seems wrong calling it
her room when she spent about an hour in there her entire stay) to collect her suitcase.
Jessica changed from her dress and into some casual attire while I gathered the few belongings that she’d dispersed around the room. In truth, her luggage had gone largely untouched. I wheeled her suitcase through the hall and out the front doorway, to her car. She popped the trunk and I stowed it inside. She gave me a goodbye hug (a real one this time) and we shared a final few kisses.
“Come back soon?” I asked, getting one last feel of her body against me.
“Just try and stop me.”
Her grin grew wider and her lips touched mine for the final time. I opened her car door and she climbed inside. We said our goodbyes and she blew me a kiss through the open window as she pulled out of the driveway. I followed her out onto the road, watching as her luxury car disappeared into the suburban abyss. And there she went, my first celebrity guest. But if word of my establishment continued to spread, she certainly wouldn’t be the last.
END
Topic: The Getaway: Jessica Chastain (Read 12450 times)