Milking Assistant Ch. 03


Chapter 3.

Jack sipped on his coffee as he walked towards his office building. At this time of the morning, he was usually still trying to wake up and process the concept of a full day of work. Today was different though. He walked quickly and confidently through the doors of Trig-Corp, wanting to get into the office as soon as possible and see Jess.

He hadn’t stopped thinking about her all night, giving himself a few more orgasms while he relived the events of the previous evening. How she smelled, tasted, and how her hand felt on his hard cock.

Jack couldn’t get the image of her licking his cum off her hand, her nipples still dripping with milk. His cock began to swell in his pants as he entered the elevator. He moved his lunch bag in front of his crotch to hide the bulge that was forming. A smile spread across his face, he felt like he was a teenager again, lusting over a beautiful woman and getting erections at inappropriate moments.

The doors opened to the office and jack immediately heard raised voices, not what he had expected first thing in the morning.

“No one gives a shit, Jessica!”

Jack immediately recognized the owner; Vince was yelling at the top of his obnoxious voice.

“You can’t just walk back in here and expect people to fall in line, you’ve been gone for three months!” He yelled.

“You can either fall in line, or you can leave the building, Vince. I don’t really care which one you choose.” Jessica replied, crossing her arms.

“If I leave, all of these people will come with me.” Vince said, turning around and making eye contact with Jack. “Isn’t that right, Jacky-boy?”

Jack’s eyes opened wide as Vince singled him out, the enthusiasm for the morning sucked out of him in an instant. Jess stood firm; her arms crossed just below her breasts. Jack could see the outline of lace on her white business shirt, telling him that she was wearing a lace bra today. He struggled to maintain eye contact, his vision constantly dipping to admire her curves.

He turned back to Vince and shook his head slowly. Even if he and Jess weren’t getting up to their lust driven milking sessions, he still wouldn’t have agreed with Vince. Jess had been nothing but great to him as a boss, and as far as he could tell, Vince was the only one that had an issue with her.

“Jacky-boy?” Vince pleaded.

“Sorry, Vince. You’re on your own here.” Jack said, sheepishly.

Vince looked around the office, trying to find other supporters as everyone tried to avoid eye contact.

“Fine, fuck you all.” He said.

Vince grabbed his bag and walked towards the elevator, bumping past Jack as he huffed and puffed.

“Anyone else have an issue?” Jess called out.

The entire office simultaneously turned and returned to their desks, not wanting to be part of Vince’s tantrum.

Jack tried to make eye contact with Jess again, but she had already begun walking to her office, slamming the door shut behind her. Jack turned and walked to his desk, he wasn’t sure what had started the argument, but he wanted to leave Jess alone while she dealt with it.

He went about his usual routine, setting his desk up and choosing music to play before he started working.

“Jack.” A hushed voice called from behind him. Tristan had wheeled his chair over to the edge of his working area. “Did you hear all that this morning?”

“I arrived at the end of it, what happened?” Jack asked.

“Turns out, Vince hasn’t been doing any work while Jessica was away.” Tristan said.


“Yeah, his portfolio hasn’t been touched. Jessica found out today.”

Jack suddenly understood why Jess was so upset. There would be a lot of work to catch up on if Vince hadn’t been doing anything for three months.

“Good riddance.” Tristan said, wheeling his chair away. “That guy was a pain in the ass anyway.”

Jack returned to his work, worried now that Jess would have a lot more on her plate. It wasn’t long before an email from Jess popped up on his screen.

Come and see me when you get a chance.

Jack’s cock jumped simply from reading the sentence, he stood from his desk and started walking, not wanting to waste any time.

He knocked on the office door that had been slammed not that long ago and waited for a reply.

“Come in.” Jess called.

Jess sat behind her desk, furiously typing away at her keyboard. Jack couldn’t take his eyes off her as he walked closer. The hint of lace under her shirt showed again as she sat with her back straight.

“Sit down, Jack.” She said, sternly.

Jack complied, watching her finish typing. Her white shirt struggled to contain her breasts as they stretched the fabric across her chest, straining the buttons. He still couldn’t believe what hey had been getting up to. Their lust filled evenings on the conference room couch, the sexting, all of it seemed so farfetched. He admired Jess from the other side of the desk, soaking in her beauty, her sexuality, her power.

“Okay.” Jess said, hitting asyalı escort enter one last time. “That’s done. Now we need to talk.”

Jess opened a drawer and began pulling things out onto the desk. Jack immediately recognized the breast pump.

“I’ve gotten my pump fixed; do you mind if I pump while we chat?” She asked.

“No, not at all.” Jack replied.

He was slightly disappointed; she wouldn’t need him to be her milking assistant if the pump was fully functional. His disappointment turned to arousal as she started to unbutton, revealing the white lace bra that he had seen through her shirt.

“I’m sure you’ve heard what happened with Vince?” She asked, unclasping her bra cup and folding it down to reveal her thick, pink nipple, standing to attention on her engorged breast.

“I did, yes.” Jack replied, mesmerized by what he was watching.

Jess took the cup of the pump and placed it over her nipple, before starting on the opposite bra cup.

Jack’s cock spang to life, forming a tent in his pants as he watched the incredibly arousing sight in front of him.

“That idiot is going to cause so many headaches, not to mention the amount of work we need to catch up on.” Jess said, fixing the other suction cup into place and pressing a button on the main unit of the breast pump.

The machine kicked into action immediately, a rhythmic rumbling sound coming from it. Jack watched as Jess’s nipples were sucked into the funnel of the pump repeatedly, milk squirting from the end of her nipples with each pump. Her nipples grew thicker, and longer with each suck, milk flowing freely.

“Jerks like that drive me fucking crazy.” She said, clearly still furious about the encounter.

“Can I do anything?” Jack asked.

“Do you think you can take on his portfolio?” She asked, casually chatting with her breasts exposed.

“Sure, if that’s what you need.” Jack replied.

“What I need is a foot massage and a drink but taking his portfolio would help too.” She said, smirking.

“Well, I could help with the other thing too.” Jack offered tentatively.

“What other thing?”

“The foot massage.”

Jess smiled across the desk, her nipples still being pulled in and out of the pump.

“Are you sure?” she asked, her smile growing bigger.

“Absolutely, if it will help you.” Jack replied, thankful that he was going to be able to touch her again.

“Sure, it will take the stress of the morning away.” Jess said turning her chair.

Jack stood up and walked around the desk, his erection bulging against the fabric of his pants. He watched as jess leaned back in her chair, her shirt falling open to further reveal her amazing body. Jack kneeled down on the floor in front of her and reached down for her foot. Jess was wearing a black pair of stilettos over the top of her usual black stockings. He gently grabbed hold of the shoe and slid it from her foot.

Jess shuffled in her chair as she reached under the hem of her skirt, unclasping her thigh high stockings from her garter belt. Jack reached up and slowly pulled the stocking down, catching a glimpse of her white panties as she unclasped the other side.

“That will make it easier.” She said, leaning back in the chair again.

Jack rolled the other stocking down, pulling the lace over Jess’ delicate feet. Her toenails were painted a bright purple, standing out beautifully against the pale skin of her feet.

Jack placed the heel of her foot onto his lap, just below the bulge in his pants, and started sensually massaging the sole of her foot, pressing his thumbs into her arch.

“Mmm, that’s the spot.” Jess said, leaning back further and closing her eyes.

Jack gently pressed into the bottom of her foot as he soaked in the sight of Jess. Her shirt had fallen all the way open now, the breast pump working away on her nipples. Splashes of milk squirted out into the funnel as her nipples were pulled in and out. He could see her white lacey underwear under her skirt, covering her most private of places.

“That’s really nice.” She said, biting her lip. “You’ve done this before.”

She was right, Jack’s last girlfriend enjoyed a foot massage, but this seemed vastly more sexual than any massage he had given before.

He moved his hands upwards, his thumbs pressing into the ball of her foot, brushing the underside of her toes. Jess shifted in her chair, sliding down more and pressing the heel of her foot against his cock.

“There he is.” She said, grinning, her eyes still closed.

Jack’s cock was already rock-hard but responded by growing again, threatening to burst out of his pants. He couldn’t believe how lucky he was to be allowed to touch Jess like this.

Just when he thought it couldn’t get any sexier, Jess lifted the front of her skirt, giving him a full view of her white lace panties, and slid a hand down the front of them.

“Sorry,” She said. “I hope you don’t mind.”

“Not at all.” Jack replied, enthusiastically.

He watched as ayaş escort her hand started moving, rubbing her pussy underneath her panties as he tried to concentrate on massaging the sole of her foot. Her nipples seemed to grow even thicker and longer as her breathing quickened, she was clearly enjoying all the sensations that were happening at once.

“Jesus.” She whispered. “That’s perfect.”

Her hand started moving faster, moving in small circles underneath her panties. Jack responded by pressing firmer into her feet, trying to arouse her as much as possible. Her chest rose and fell faster, approaching a climax quickly.

“Jack,” She whispered. “Suck my toes.”

Jack didn’t hesitate, he immediately pulled the foot to his mouth, stuck his tongue out and licked at the bottom of her big toe, sliding it into his mouth and gently sucking it.

“Oh, God.” Jess hushed, her hand moving faster.

Jack had never sucked a toe before, he had expected that it would taste bad, but Jess’ feet had a pleasant, flavor. Jack loved the way they tasted in his mouth as he rolled his tongue over her toe.

Jess shifted in her seat, lifting her ass and sliding her panties down to her knees, giving Jack his first look at her beautiful pussy. It was clean shaven, not a hair in sight, soaking wet and perfect. What took him by surprise was her piercing, ball at the top and bottom of her swollen clitoris. Jack sucked at her toe while watching her vigorously rub her pussy, flicking the piercing back and forth.

“Keep going.” She whispered, her body beginning to shake.

Jack took all five of her slender toes into his mouth, running his tongue alone the underside of each one. This pushed Jess over the edge, her body started to convulse, her legs quivering as her orgasm approached quickly.

“Jack.” She whispered sharply, as her abdomen contracted over and over.

Jack could hear how wet her pussy was as her hand rolled around her clitoris vigorously, her body writhing with pleasure. Her orgasm washed over her, wave after wave causing her to spasm violently.

Jess let out a deep groan as her body started to relax, her hand slowing to small gentle circles on her clit. The breast pump continued to suck at her nipples, even though no milk was coming out anymore.

Her whole body went limp as Jack removed the toes from his mouth, continuing to gently rub the arch of her foot. Taking in the sight of the stunning woman in front of him. Jess slowly opened her eyes and looked down at him, a large smile forming across her face.

“Thank you.” She whispered.

“Any time.” Jack replied, smiling back at her.

Jess reached across and pressed the off button on her breast pump, the machine coming to a halt. She pulled the pump cups free from her breasts and used her bra to wipe the excess milk from her skin.

“I got a bit carried away there.” She said, clipping her bra back into place.

“That’s fine by me.” Jack said, still looking at her wet pussy.

Jess saw him looking and opened her legs slightly.

“What do you think?” She asked, seductively.

“You look amazing.” Jack replied. “I didn’t expect that you’d have a piercing there.”

“No one does, it’s my little secret.” She said, winking. “A secret that feels utterly amazing.”

Jess ran her fingers over her pussy again, making gentle circles, before standing up and pulling her panties back into place.

“We should finish up before anyone gets suspicious.” Jess said, “I’ll leave first and put this milk in the fridge. You can sit here until our little friend calms down.”

Jess pulled her stockings up, buttoned her shirt and stepped into her shoes as she picked up the two bottles of freshly pumped milk. She walked around the desk and headed for the door, stopping in front of Jack.

“Did you want a taste first?” She asked, shaking the milk in the bottles.

“Sure.” Jack said, excitedly.

Jess unscrewed the lid on one of the bottles and instead of offering it to Jack, she lifted it to her own mouth and took a big sip. She then reached forward and grabbed the back of Jack’s head, pulling him in close and giving him a deep kiss. Milk flowed from her mouth to his as her tongue explored his mouth, taking him by surprise. Jess’ fingers gently pulled at the hair at the back of his head as she pressed against him.

Jess then broke away, the kiss ending just as fast as it had begun.

“Mmm, tasty.” She said, biting her lip.

Jack couldn’t reply, in complete shock with what had happened in the last twenty minutes.

“Sit down and let this go down.” Jess said, squeezing the shaft of his cock through his pants, then turning and leaving the office.

Jack took a seat at the desk, pretending to look at his phone while he waited for his erection to die down. His rock-hard cock throbbed, begging to be touched, aching for release. Every time he thought that it was beginning to subside, the image of Jess pierced pussy would pop into his head. Or, her perfect breasts, or the aydınlıkevler escort way her toes had felt in his mouth. What ever it was, it meant that his cock stayed hard, refusing to surrender.

Several minutes had passed and he was no closer to being able to leave the office. People would surely start to wonder what he was doing in there alone. Jack was beginning to panic when the door opened, Jess walking back into the office.

“What are you still doing here?” She asked in a hushed voice.

“Sorry, it wont go down.” Jack said, embarrassed.

“Why not?” Jess asked, closing the door.

“Why do you think? Because that was one of the sexiest things I’ve ever seen, let alone participated in.”

Jess looked shocked for a moment, before a smile spread across her face.

“You think I’m sexy?” She asked.

“Are you kidding me?” Jack said, laughing. “I’ve never met anyone as sexy as you.”

Jess looked genuinely flattered, her hand resting across the top of her breasts. Jack was telling the truth; he was falling in love with Jess at an alarming rate.

“Well, that’s very nice of you to say, Jack. It really means a lot.” Jess said, her voice still hushed. “But people will definitely start talking if you spend much longer in here.”

Jack looked around the room, trying to find way to leave the office. His eyes settled on the wastepaper bin at the end of the desk.

“I’ve got an idea, when I open the door, tell me to empty the bin.” Jack said.

“The bin?”

“Trust me.” Jack said, standing up and walking to the door, awkwardly adjusting his cock. He opened the door slightly and nodded to Jess.

“Jack, can you take this bin with you?” Jess called out, purposely loud.

Jack walked back in, picked the bin up and covered the bulge in his pants with it. He winked at Jess who mouthed a silent thank you to him and left the office.

Jack moved quickly through the office, using the bin to disguise his aroused state. He passed the lunchroom and turned down the corridor towards the toilets. He put the bin down in the corridor and entered the toilet, quickly taking a cubicle.

Jack quickly undid his pants and retrieved his swollen cock from inside his underwear, stroking its length as he imagined Jess’ wet pussy. He was sure there was no one else in the toilet but was being as quiet as possible, just in case.

His cock was aching, his balls already starting to tighten, when his phone buzzed.

He reached down and fished the phone from his crumpled pants, opening the message that Jess had sent him.

Don’t cum if you can help it. I want to do it for you.

Jack gritted his teeth, he desperately needed to relieve the pressure in his balls. He was close to spraying cum all over the toilet cubicle already. He took a moment to consider her request, wondering if his cock would ever go soft without release, when a second text came through.

I’ll make it worth the wait.

Jack sat down on the toilet seat, frustrated but excited by the prospect of what she meant by that. He decided that he would sit and wait until his erection died down of its own will. He replied that he would try his best, then opened up the stock market app on his phone, hoping to bore his cock into a slumber.

Ten minutes later he emerged from the toilet and returned to his desk, his cock wasn’t completely flaccid, but it was enough to walk without drawing too much attention. He plugged his headphones in and resumed working, pretending that nothing had happened.


The hours passed extremely slowly, the images of Jess distracting Jack from his work. The pressure in his balls not helping the situation either. He watched as the sun started to sip closer to the horizon and his colleagues started filtering out of the office. A few stayed late, probably trying to catch up on work that had been left by Vince’s laziness, but eventually, the last person had stepped into the lift.

Jack stood from his desk straight away and quickly walked to Jess’ office, checking each section on the way to assure everyone was gone.

Jack walked through her open door, seeing the woman he lusted for still working at her desk.

“Are they all gone?” She asked, never looking away from the monitor.

“I just checked, looks like it’s just us.”

“Good, I’ll be a few minutes. Wait for me in the meeting room.” Jess said, typing quickly.

Jack left her office and walked to the meeting room, taking a seat on the couch that had hosted many of their sexual escapades.

He was reading his phone, patiently waiting for Jess, when he heard footsteps coming down the hall, the unmistakable sounds of Jess stilettos clicking on the floor. He looked up just as she turned the corner and entered the office, completely naked except for her stockings and high heels.

Jack’s jaw fell open as he gawked at the curvy, voluptuous woman in front of him. He could hardly believe his eyes, her engorged breasts hung perfectly and her frame, swaying gently as she walked towards him.

“Pants off, now.” Jess commanded.

Jack stood up and frantically started pulling at his belt, his hands shaking with excitement. He pulled it free and dropped his pants, kicking his shoes off at the same time. Jess reached out and pulled his underwear down, his cock springing free.

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