Golden Globes Ch. 02

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A night with Jessica Chastain and Angelina Jolie continues.
4.5k words
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Part 2 of the 2 part series

Updated 06/08/2023
Created 01/19/2018
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The next few minutes were a blur as Angelina guided Jessica and I away from the ballroom ceremony and towards the hotel section of the Beverly Hilton. When my supervisor approached us she remained in control.

"Hello Miss Jolie, Miss Chastain," he nodded to them before continuing, "If you don't mind, I need to-"

"I was just..." I started to speak before feeling a hard pinch on the back of my bicep from Angelina.

"Giving us a tour," she finished my sentence for me, "We are having a wonderful evening." Her face lit up with a smile.

"I..." my boss continued, glancing back and forth between Angelina and Jessica, likely noticing her smeared makeup. Angelina took a sudden step forward and leaned in uncomfortably close to him. Her smile vanished.

"Is my evening going to continue to be wonderful?" her gaze pierced his eyes and sunk into his brain, "Or will I need to have a word with your boss?"

"N-no problem at all, Miss Jolie," he stammered out, shifting his weight onto his heels.

"Good," she produced a $100 bill as if by magic and stuffed it into his suit pocket, "good."

He got the memo and scurried off with his tail between his legs, and when he was out of sight we rounded the corner to the hotel elevators.

We bypassed the main elevators as Angelina led us to one that took us to the suites on the higher levels. After the doors closed, she started methodically removing her jewelry and placing it into her purse.

"You will do as you are commanded," she stated authoritatively, "or you will be punished," she finished with a soft smile.

"Yes mistress," Jessica replied immediately, her gaze fixed on the floor as we rose to the highest level.

"Yes mistress," I parroted, making eye contact with Angelina as she removed her second earring.

She stepped to me immediately and held level eye contact, her heels brought her up to my height.

"Take off your dress." Angelina commanded, without breaking our staring contest. The elevator dinged as we reached our floor.

"Wha-" Jessica stopped herself mid word, but sat frozen for a moment.

I reached past Angelina to hold the door open, and she extended her hand out to Jessica, not bothering to repeat herself.

I heard a zipper come undone, and a moment later Jessica's purse and dress were handed to Angelina.

I forced my eyes to stay still, I found myself eager to please Angelina.

"The last door on the right, walk slowly." she again commanded, and I heard the click of high heels on the floor as Jessica entered the hallway.

"Good boy," she purred a whisper to me as Jessica walked away.

She looped her free arm into mine and led me into the hallway, following Jessica.

We walked unbearably slow, trailing behind as Jessica obeyed Angelina. She swayed side to side slightly, putting on a show for us as we admired her from behind.

"Don't you think her ass looks incredible?" Angelina questioned loudly as we passed the halfway point.

"Yes mistress," I replied, I thought about continuing but she cut me off.

"Do you desire it?" Her commanding tone was having a massive effect on me, and clearly Jessica as well, as she turned her head to peer at us for a moment as she continued slowly forward.

"Yes mistress, very much," I answered as we neared the end of the hallway.

Jessica reached the suite and stood next to the door, peering at us as we closed the gap.

"Stay," she commanded simply, "follow me, boy."

Jessica had already been stepping forward, she stopped in her tracks and nervously shifted her weight, waiting for clarification.

"Strip," she instructed me further, before throwing her purse onto the couch and lazily gliding into her bedroom.

I didn't have to be told twice, I took a minute to fully disrobe and place it in a neat pile as Jessica watched me, holding the suite door open.

Angelina emerged again, this time wearing a plush robe instead of her awards gown. She knelt next to a bag in the hallway and took out a camera and a tripod.

She set it up just inside the suite door, jamming it open with a tripod leg. The camera faced outward, centered on a reddening Miss Chastain. Again, she looked beautiful with her fiery hair framing her angular face. Her continued embarrassment was visible all the way down her chest as she patiently waited.

"Put on a show for us," Angelina instructed while dragging a chair over to where I remained standing in the entryway, "or I'll send you back down the elevator just as you are."

On shaky legs, Jessica backed up into the opposing wall, bit her lip, and glanced down the hotel hallway.

I looked down as Angelina settled into the chair in front of me, but her eyes gleamed with anger as she met mine.

"It would be rude to look away from a show being put on just for you, wouldn't it." she asked without a question mark.

I looked back up just as Jessica slid her middle and ring fingers into her pussy up to the second knuckle, her legs splayed open as she leaned against the wall.

Her mouth opened idly as she slowly fingered herself. I shifted my weight and my cock bobbed out in front of me. It caught Angelina's eye and I noticed a small smile grow on her face from the corner of my vision.

I kept my eyes trained on Jessica, trying my best to keep up with the game. Her eyes grew hazy as her fingers slid in and out, agonizingly slowly.

"Are you enjoying the show?" Angelina asked, her face suddenly turned towards me.

"Ye-" I started, before being cut off.

"I think he's getting bored, I'm going to need you to spice it up," she instructed Jessica.

Jessica responded by dragging her fingers up her body, taking the time to do a slow, wet circle around her nipple, before bringing them up to her mouth to suck on her own juices. Her other hand moved down to play with her clit as she sucked on her fingers obscenely.

Suddenly, a door down the hallway opened, and Jessica jumped at the noise. Her head turned back toward us with panic in her eyes, but Angelina held her hand up, shaking her finger back and forth as a no before Jessica could make a sound.

Jessica's legs trembled as she stared straight ahead at us, her fingers frozen in her mouth. We all heard footsteps leading down the hall away from us, toward the elevators.

We waited a moment, then another. The elevator arrived with a ding, then seemingly as soon as it's doors closing echoed down the hallway, Jessica was begging to come inside.

"Please, Please, PLEASE, mistress," she begged, "Let me come in with y-"

"You really want to come inside before you finish the show?" Angelina slowly teased her.

"YES, please mistress, I'll do anything," Jessica continued.

"You know what I think," Angelina spoke softly, "I think you're a tease, and teases don't get what they want."

Jessica whimpered in the hallway, her legs again shaking.

"Do you know what teases get?" Angelina purred as she turned to me, signaling me.

"Teases get punished," it was like she beamed the words directly into my head.

"Correct, boy." She said as she turned back, but my dick started to get the best of me, and I took a chance to escalate.

"I think she should beg for her punishment." I followed up. Angelina's eyes snapped back up to me, filled with fire.

"Beg," Angelina wasted no time, she immediately affirmed my idea.

"Please mistress, please, take me inside and punish me," Jessica panted out, her fingers again sliding in and out of her pussy.

No longer feeling fully restricted, I moved forward to grab the camera. I paused briefly to look at Angelina for confirmation, but she only held my gaze in response.

"On your hands and knees," I commanded to Jessica as I moved the stand and took the camera.

She got the hint and dropped to the floor, then slowly started to crawl towards and into the doorway.

Now holding the camera, I framed both of them as Jessica entered, approaching Angelina in her chair.

Angelina said nothing, her legs spread slowly as Jessica inched nearer.

"Earn your punishment, prove to your mistress that you deserve it," I instructed, but Jessica was already on her way in. Her red hair settled between Angelina's pale thighs, framed by the purple robe.

Jessica gave no indication that she was going to be any less gentle on her than she was with me. Her head barely moved, as Angelina sank slightly in the chair, arching herself to give Jessica the best access to her pussy.

With the door shut behind us, I felt more free to move around and get different angles of the action. I framed them from behind, capturing the globes of Jessica's perfect ass all the way up to Angelina's steadily reddening face.

Jessica's head was still barely moving at all, the only sounds in the room were my footsteps and Angelina's slightly labored breathing.

Angelina's head turned to me, "Put that thing back up, I need your hands free."

I took a moment to reframe them with the camera on the tripod, and as i stepped toward them again she grabbed at me. I had hoped she was going to reach for my cock, but instead she grabbed and guided my hands.

She planted one hand firmly on the back of Jessica's head, interlacing my fingers in her hair, applying serious pressure. Jessica seemingly got the hint, I started to hear some wet sounds as her tongue worked Angelina like it had already worked me.

My other hand was brought up to Angelina's mouth, her eyes screwed shut as she took my thumb in her mouth and gently started to nurse on it. Her cheeks were fully flush now, I noticed her thighs tremble a bit as she got closer to the edge.

I wished that my hands were free to explore, I was desperate to feel Angelina up and squeeze Jessica's ass, but it was clear that I was not in control.

I kept firm pressure on Jessica's head, reminding her of her place. The room was eerily quiet considering our activities, the wet sounds from their mouths were barely audible.

My cock pointed straight out, seemily trying to beam a message into Angelina's head. As if on cue, she opened her eyes to meet mine, while continuing to worship my thumb in her mouth. My cock was jealous.

We maintained eye contact as her legs tensed up, and her eyes narrowed at me. She seemed to lose focus as she drifted over the edge into her orgasm. I wasn't going to let Jessica's head go anywhere, but I felt no resistance from her as Angelina's hips started to lightly buck forward.

Spit dribbled from her mouth into her cleavage, she slowly became more exposed as she trembled and shook through the waves of her pleasure.

Her mouth hung open as she reached her peak, and my thumb slipped out. She let out a slight whimper, and I took a risk and leaned in.

Her hands shot up and grabbed my neck, pulling me in as my lips met hers. She didn't hesitate to shove her tongue in my mouth as I attempted to clean up her spit and feed it back to her. We both moaned as she rode her orgasm down, she settled in as I still held Jessica's head between her thighs.

After coming down to earth, her hands stayed firmly on my neck, keeping me close. I involuntarily tightened my fingers in Jessica's hair as we continued to make out, and it became hard to tell where the wet noises were coming from as we got sloppier.

Angelina's kisses slowly grew more gentle, and after one last deep tounge she retreated and placed a final kiss at the coner of my mouth. Her eyes fluttered open and she gazed at me hazily.

"Time for punishment," the words fell out of her mouth and into my ears, bypassing my brain entirely and sending the signal directly to my cock.

I lifted Jessica up by her hair, she got the memo and shakily rose to her feet, panting as she did so. I took the lead and led her over to the bed, keeping her head tilted back with my hand still gripping her hair.

Angelina drifted past me into the walk in closet, I heard her rummaging around and few zippers opening up.

Jessica made eye contact with me, but I wasn't about to ruin our game. I reached down with my other hand and slowly traced along her slit, feeling her wetness and leaving a trail behind.

Angelina walked back in holding a tie and some silk rope. She got to work quickly, first by tying a blindfold for Jessica, and then walking around us and roughly yanking her hands behind her back. She wasn't tender at all as she restrained the beautiful redhead, forcing her arms backward as she tied her hands and forearms together as tight as she could.

Angelina disappeared for another short moment, this time buckling a strap on with a huge dildo onto herself as she reemerged.

"Relax, this isn't for you," she calmed me before I had a chance to say anything. She stepped up to Jessica and slapped her face, startling her.

"Ready for your punishment, whore?" She spat at her as she reached down and circled Jessica's clit with her middle finger.

Jessica trembled at the disparate sensations, and made a shocked humming noise before responding. Angelina's left hand shot up to Jessica's throat, startling her even further as she jumped slightly.

She squeezed lightly as Jessica gasped, seemingly unable to respond coherently. Angelina guided her by the throat sideways and then backward toward the bed, giving her a shove as they closed the distance.

Jessica bounced on the bed as she fell with her arms tied behind her. She made no effort to right herself, and her breathing grew audibly labored.

I turned to grab and reorient the camera as Angelina nodded at me, possibly having forgotten that detail in her lust. I quickly reframed the camera on the bed and walked to the opposite side as Angelia spun Jessica around by her legs.

"Bend this slut over," she commanded, before reaching down to toss me a previously unseen bottle of lube.

I caught it then quickly turned Jessica over onto her stomach and lifted her up by her hips. I knelt behind her on the bed, her head hung over the edge slightly as she balanced on her upper chest and shoulders.

The bed was high enough that Angelina hardly had to bend her knees at all, and she got to work immediately without giving me further instructions. I definitely didn't need any, the bottle of lube did all of her talking for her.

Angelina roughly shoved the dildo into Jessica's mouth, and quickly built up a rhythm as she started to fuck her face with it.

"I don't want to hear a word out of you, slut," Angelina instructed her with both of her hands in the redheads messy hair, "breathe out of your nose, bitch."

I snapped open the bottle as I raced to catch up. I didn't bother to lube myself up, I only squirted a healthy dollop of it into her ass crack before pushing the tip slightly into her asshole and giving another squeeze.

Jessica moaned around the synthetic dick in her mouth as I pressed myself into her asshole. I took it relatively gently, I didn't want to disappoint Angelina, but she seemed pretty preoccupied with attempting to get the dildo into Jessica's throat.

"Oh my FUCK, she's tight," I breathed out as my first few inches slipped in. Jessica's fingers contorted and her hands wiggled slightly as she tried to settle into her position.

Angelina was rocking Jessica's head back and forth as she tried to establish a rhythm. Jessica, to her credit, was hardly gagging, and started to moan as I sunk in deeper.

My hands both gripped her hips as I passed the halfway point, slowly pulling in and out, pushing a little harder and deeper each time.

"I don't care how tight she is," Angelina casually addressed me, "if she isn't limping when we're done with her I'll have your head." I immediately sped up, trying to catch up to the pace of abuse that Jessica's throat was taking.

It wasn't hot in the room but sweat was beading down Jessica's back. My fingers dug in and left marks as I ramped up to match Angelina.

Jessica's gagging had lessened, and soft wet squelching sounds came from both ends as we rocked her body between us.

"Good slut, learn to keep that throat open," Angelina said pointedly as she punctuated her words with harder thrusts, "I'm going to whore you out, call up everyone in your contacts list and have them come empty their loads in your mouth."

My dick swelled involuntarily at the thought, and Jessica squirmed harder. I reached for the lube bottle as I passed the 3/4 mark, but Angelina stopped me.

"No more lube, punish that fucking ass," she instructed. Jessica moaned loudly below us and seemed to sink into the bed a little more.

We had now established a rhythm, Angelina slowed slightly to match my pace, and I neared bottoming out as I slowly worked Jessica's asshole open a little bit more with each thrust.

Angelina's robe hung open and loosely slid down her shoulders. Not that I needed any extra visual stimulation, but I caught myself staring at her beautiful body as we pistoned Jessica between us.

"Speak," she commanded, catching me before I realized it.

"I want your body," I blurted out, pushing harder and deeper into Jessica as I did.

"Your wants are not my concern," she leaned in and gripped my face, her nails digging into my cheeks as her other hand forced Jessica all the way down on her strap, holding and choking her there.

"Let's both fuck her," I pivoted. Angelina was humping against Jessica's face now, forcing her back into me.

Seemingly pleased, Angelina released me and leaned back, getting back into her rhythm of fucking Jessica's face. I doubled down and gripped her hips harder as i willed myself deeper.

Jessica moaned low and loud as I entered her further, and Angelina had both hands gathering her hair into a ponytail as she sped up her assault.

My eyes wandered back up Angelina's body, taking in her bouncing tits as we rocked the bed back and forth. I grunted and found another gear, speeding up again as I finally managed to bottom out fully in Jessica's ass.

Jessica was shaking now, her back soaked in sweat as she twitched and moaned for us. I was starting to get into a rhythm again, and starting to think about emptying my load in her, when Angelina surprised me with a hand on my chest, shoving me hard.

She had pulled out at the same time and trotted off to the closet again without explanation. Jessica's knees gave out and she collapsed on the bed in a heap.

My nurturing side kicked in and I layed down next to her panting form, I kissed her lightly on her sweaty forehead and she mewed delicately back to me. I traced my fingers along her arms and back, following the goosebumps and eliciting a tremble from her.

A buzzing sound startled me and I turned back toward Angelina. She had in her hands a large black buttplug shaped dildo, and quickly closed the gap back to the bed.

With her hand on my chest again, she guided me back against the pillows. As I settled, she turned her attention back toward Jessica.

*WHAM*

Her hand connected with Jessica's ass so unexpectedly hard and loud that it even made me jump. Jessica made a yip noise then folded onto the bed.

"Mistress..." Jessica moaned out as Angelina brought her hand down again, "...please..."

"Please what? You fucking whore, you were begging for punishment a minute ago-" Angelina started.

"Please punish me," Jessica begged, "Use my body."

With that, I took the initiative again, and guided Jessica over on top of me. Apparently not rough enough for Angelina's liking, as she punished Jessica's ass cheeks with a few more slaps while I lined up beneath her.

I looked to Angelina for confirmation, and she nodded when we locked eyes. We were getting more in sync, though I was still more of a follower than an aggressor. With a hand on her hip, I pulled Jessica down and sunk into her balls deep, eliciting a deep groan in response.

Beside us, Angelina spread Jessica's asshole open. Her groan lifted in pitch to a yelp as the still vibrating dildo was roughly forced into her ass.

I started rocking myself in and out, both hands on her hips now, when Angelina mounted herself behind Jessica. I felt the strap on press down on my cock as she lined herself up. Jessica's body tensed in anticipation as it dawned on her what was about to happen.

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