The Getaway: Jessica Chastain

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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.

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AnonymousAnonymousabout 2 years ago

Could you please continue the #GangbangChallenge series? Even if it's just one or two more stories, at least it could be wrapped up.

DarkSwordsmanReturnsDarkSwordsmanReturnsabout 2 years agoAuthor

Thank you for your feedback. I do plan on making this a series but focusing on other celebs, not just Jessica. I do plan for her to return at some point though, along with a couple of the women you mentioned. Watch this space.

AnonymousAnonymousabout 2 years ago

This was so fucking hot. PLEASE PLEASE PLEASE make this a series! There are definitely more installments to be written about Jessica and Tyler. For example, in the next one, she could come back wanting to be treated like a nasty whore, with slutty lingerie, more cum all over her face (with polaroids taken for both their subsequent viewing pleasure), and anal sex. The installment after that could feature Jessica bringing one of her actress friends (e.g., real-life friends Jess Weixler, Anne Hathaway, Lupita Nyong'o, Gugu Mbatha-Raw, Emily Blunt, Diane Kruger, etc.), and in the installment after that, Jessica could bring one of her male actor friends (e.g., Oscar Isaac, Sebastian Stan, James McAvoy, etc.) for DP.

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