Milking Assistant Ch. 02

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Milking Assistant

Chapter 2

Jack stared at the computer monitor; his mouth partially open. He reread the email that Jess had sent to him, just to make sure that he hadn’t imagined her words.

I’m going to need you to work late every day this week.

Jack slowly shook his head, letting the implication of her words sink in. There was only one thing that she could have meant. Jess wanted him to help her with her milk again.

Or maybe even more.

Jack reached down and rearranged himself, his cock becoming uncomfortably hard while thinking about the email. He quickly closed the window and looked around the office, confirming that no one had been looking at his screen, potentially seeing Jess’ message. His stomach fluttered, both excited and nervous about the new relationship in his life. If it could even be called a relationship.

His love life left a lot to be desired these days, but only since moving to the city. Jack’s last relationship, with Amanda, had lasted the better part of three years, the longest relationship of Jack’s life. They loved each other, had similar interests, even liked the same movies; but within the first few months Jack knew that it probably wouldn’t work out.

They were completely incompatible sexually. Jack liked to be active in the bedroom, exploring new ideas and dynamics; Amanda liked the lights off and missionary.

Helping Jess with her engorgement was the first truly kinky thing that Jack had ever been allowed to participate in; and it had been with an incredibly hot woman. Jack closed his eyes, remembering the taste of her milk, the feeling of her nipple in his mouth, and the way her milk dripped from her breasts as he jerked off.

Jack rearranged his pants again; at this rate he would need to go and let off some steam just to concentrate on his work. He put his headphones into his ears and selected some music to listen to. His theory was that if he focused on his work, his erection would go away, and the end of the day would seem to arrive sooner.

His plan had worked, before long he checked his watch and saw that it was almost lunch time already, the end of the day getting within reach.

Jack pushed himself away from his desk, taking his headphones out as his chair rolled across the floor. He stood and began walking towards the kitchen when Jess suddenly appeared in front of him.

“Oh, hi.” Jack said, willing his cock to stay flaccid.

“Have you been doing work on the Smith file?” Jess said, firmly.

“Uh, yesterday I did. Why?” Jack replied, nervously.

Jess’ shoulders slumped as she let out a sigh.

“Well, that file is a mess, we need to have a chat. My office, please.” Jess said, her arm raising and directing him across the office floor.

Jack’s face flushed, he thought he had done good work on the Smith file, he couldn’t think of anything that could be wrong. Definitely nothing that would require a telling off. He walked through the doorway to Jess’ office and took a seat in front of her desk. Jess walked in a moment later, closing the door behind her.

“Jack.” She said, as she stared closing the blinds between her office and the rest of the building. “I wanted to thank you again for helping me last night.”

Jack watched her pulling the blinds closed, still unsure if he was actually in trouble of not. He watched her reaching for the cord, her blue dress rising up the back of her legs each time.

“Ah, that’s okay.” Jack replied, confused.

“And I want you to know, what happened is completely between the two of us.” Jess said, sitting in her chair on the opposite side of the desk. “You don’t have to worry about being treated differently to the rest of the staff.”

“Oh, sure, that’s fine.” Jack stammered.

“That arrangement is completely separate to work. Are we on the same page?”

“Absolutely.” Jack said, nodding with enthusiasm.

“Good to hear.” Jess said, leaning forward. “Because I was wondering if you’d be interested in helping me again.”

Jack’s cock sprang to life instantly as he realized why Jess had closed all the blinds.

“This isn’t about the Smith file, is it?” He said.

“No, Jack, I don’t care about the Smith file in the slightest.”

“You want help now? In here?”

“That’s right, this piece of shit is still broken.” Jess said, pushing her breast pump with the back of her hand. “I fed on my left breast this morning, but my right one is engorged; and without a pump I’m kind of stuck.”

Jack shuffled in his seat, his erection trying to form a tent in his pants. He couldn’t believe what he was hearing. This sexy, busty woman was asking him to suck on her nipple again. He was trying to calm himself down, hoping not to reveal how excited the prospect made him, while sounding eager enough to show interest.

“Absolutely!” He blurted out. “If that’s what you want.”

“It’s not what I want, but what I need, Jack. I need you to know that if you say no, nothing bad will Anadolu Yakası Escort happen to you, this is completely up to you.” Jess said, trying to reassure him.

“No that’s fine, I’m happy to help. But what if someone comes in?”

“No one will, they think you are in trouble, they will steer clear.” Jess said, smiling. “And the door is locked.”

Jack looked around the office, trying to see if there was any other way for people to see them, but came up empty. His hands shook slightly, quivering with excitement.

“Okay, sure. I’m in.” He said, smiling across the desk.

“Thank god, I’m bursting here.” Jess said, returning his smile.

“How should we do it?” Jack asked, looking around the office once more.

“Well, I don’t have a couch here, so we are going to have to improvise.” Jess said, slowly unbuttoning her shirt. “I think if I sit here, and you kneel on the ground next to my chair, we will be close to the right height.”

Jack stood up from his chair and walked around the desk, more than ready to help his boss out. He watched Jess’ hands make their way down her shirt, picking away at each button, revealing more of her chest with every movement.

“Well then.” Jess said, looking at the tent in Jack’s pants. “I guess you’re telling the truth about wanting to help.”

Jack quickly and unsuccessfully tried to cover the bulge in his pants. He was so swept up in the moment that he had forgotten about his cock.

“Shit, sorry.” He said.

“Don’t be, it’s only natural. I thought he would be a bit more subdued after last night, but it looks like he is relentless.” Jess said, chuckling.

Jack watched as she finished with her last button, before pulling the white fabric aside, revealing a white bra with thick black trim around the seams. Her breasts looked fantastic, her thick nipples poking through the fabric of the bra. Her cleavage plunged downwards, a dark shadow cast between her engorged tits.

Jack’s cock strained against his pants, begging to be set free, as he knelt down next to her chair.

“Is here okay?” He asked.

“Only one way to find out.” Jess said, unclasping the bra from the front, her breasts falling free.

Her nipple stood firm, white dots of milk forming on the tip before dripping off. She leaned forward, turning her body in the chair to bring her nipple closer to Jack’s mouth.

“You might have to sit up a bit higher.” She said.

Jack straightened his back, leaning forward to meet Jess’ breast with his mouth. The arm of her office chair pressed into his chest, stopping him from leaning forward any further. Jess placed her hand underneath her breast as she leant forward, pushing her breast towards him.

Jack opened his mouth and tried to take the nipple in, but he was a few inches short of where he needed to be, the arm of the office chair impeding his ability to latch onto her nipple. He stuck his tongue out, gently licking the milk from the end of her nipple, before she pulled away, sighing as she did so.

“This isn’t going to work, come sit in front of me. You can get closer.”

Jack shuffled on his knees, moving to in front of Jess. He looked up at his boss, her breasts swaying slightly as she moved forward in her chair. Jess sat at the edge of her seat and opened her legs, her knees going on each side of Jack’s body, as she rolled the chair forward.

Jack glanced down, looking at her stocking covered thighs as they passed by him, her blue skirt riding up, a hint of white panties showing.

“Eyes up, Jack.” Jess said, chuckling.

Jack lifted his head and was immediately met with a breast pressed against his face. He opened his mouth and took Jess’ nipple into his mouth, sucking eagerly as the first flow of milk hit his tongue.

“That’s it.” Jess said, breathing a sigh of relief.

Jack felt the milk pouring into his mouth, covering his tongue as it flowed freely from her stiff nipple. He thought is tasted sweeter today, less metallic, almost impossibly warm.

“My letdown is coming.” Jess said, whispering sensually.

Jack was ready for it this time, sucking firmly on her nipple as he felt the increase in volume come pouring out of her breast. He managed to avoid the jet of milk hitting the back of his throat, swallowing quickly to try and keep up.

Jack lifted his hand, gently holding the bottom of her voluptuous breast as he suckled away at her nipple. Jess inhaled sharply for a moment when his hand made contact with her skin, surprised by his tender touch.

Jack noticed goosebumps spreading across her chest as he rolled his tongue across her nipple, purposely trying to arouse her. He looked up at her while he sucked and saw that she had her eyes closed. Her mouth was slightly open as she breathed quickly, lost in her own word.

Jack felt her legs close slowly, her thighs pressing against his sides as she held him. Jack took it as a sign that he was doing a good job and began sucking slightly harder, trying to settle into Bostancı Escort a rhythm of on and off suction, intentionally trying to pleasure her.

The flow of milk had started to ease off, a few drops coming out with each suck instead of a free-flowing stream.

Jack knew that the session would come to an end soon.

He prepared himself for Jess to pull away, or to relax her legs from around him, but neither happened. She remained still, the nylon of her stockings rubbing against his ribs, breathing deeply.

He could see that she was enjoying herself, the situation turning from functional to erotic. Jack knew that he wanted to take it further but wasn’t entirely sure what would be acceptable.

His free hand began to move, running on auto-pilot, tracing gently over the skin of her stomach. He slowly reached out for her free breast, taking the weight of it into the palm of his hand.

Jess took another sharp breath, flinching slightly as Jack touched the flesh of her other breast. He looked up and saw that her eyes were still closed, her legs were still holding him tight, a signal that he could continue.

He sucked at nipple while his hand gently rubbed her other breast, her breathing quickening further as he rolled his fingers over her nipple. It responded to his touch, stiffening further, becoming moist as milk began to form on the end of it. Jack felt the milk roll down his thumb as he rolled the nipple between his thumb and forefinger.

“God…” Jess whispered, her legs tightening against him again.

Jack realized that there was hardly any milk flowing into his mouth anymore. He continued to slide his tongue across her nipple, gently flicking it back and forth.

Suddenly, Jess’ legs opened, releasing Jack from her hold. Jess sat up straight and pulled her nipple from his mouth.

“That…that is enough.” Jess said, panting gently.

Jack removed his hands from her body, leaning away from her as she rolled her chair away slightly.

Jack took in the sight of the woman in front him. Jess’ eyes were still shut, her enormous breasts still bare, milk slowly dripping from the side that he wasn’t sucking on. Her skirt had hiked up further, revealing that she was wearing thigh high stockings, white lace panties covering her most private of places.

His cock throbbed as it strained against his pants. He desperately wanted to take his cock out and jerk-off, but he needed Jess to be the one to bring it up. He didn’t want to assume that he was allowed to do that in front of her, even after what they had just done together.

Jess slowly opened her eyes and looked down at Jack. A smile started to spread across her face; beautiful white teeth showing behind bright red lipstick.

“Well…” She said, mostly whispering. “That did the trick.”

A knock at the door rang through the office, making them both jump and turn to look in that direction.

“Jess?” A voice called through the door.

“What is it?” Jess replied.

“We have that client meeting; it was supposed to start five minutes ago.”

“Shit.” Jess said under her breath. “I’ll be done in a moment!” She called back, scrambling to button up her shirt.

Jack stood up, giving her the space to straighten her clothes out. Jess chuckled as she finished buttoning her shirt, looking down at the bulge in Jack’s pants.

“We can take care of that later.” She said, pulling her skirt into position.

Jess passed a clipboard to Jack, a piece of paper clipped to the front.

“Sit at my desk and pretend to fill this in until your boner dies down.” She said.

Jack understood, though he thought it might be a little while before his cock decided to cooperate.

Jess moved towards him and gave him a gentle kiss on the cheek, before reaching down and grabbing the shaft of his cock through his pants.

“Thank you, I owe you one.” She said before swiftly walking to the door and leaving the office.

Jack quickly sat down, hiding the tent in his pants as best as he could while pretending to fill in paperwork. The sounds of the rest of the staff had returned now that the door was open, people rushing about their day, completely oblivious to what had happened in this office.

Jack waited patiently for his erection to start to soften, struggling to push images of the last thirty minutes to the back of his mind. After a while, the rumbling in his hungry stomach pushed the images of Jess’ beautiful breasts away and allowed his cock to soften.

Jack stood up and walked to the kitchen, wanting to reheat his lunch and retreat to his desk, but as soon as he walked in, he was greeted by a familiar voice.

“Jacky-boy!” Vince called out, his mouth half full of food. “I heard you got dragged into the Ice-queen’s office, you get fired?”

Jack retrieved his lunch and placed it into the microwave before engaging with Vince.

“No, not fired, just clearing up a few things.” He replied.

“Lucky, usually she clears things up by clearing Ümraniye Escort peoples desks out.” He said, chuckling at his own joke.

Jack feigned a smile, not wanting to upset Vince but also not wanting to bad-mouth a woman that he was lusting for so badly. He grabbed his lunch and left the kitchen, giving Vince an awkward wave on the way out.

He wanted to tell Vince to shut-up, but he knew that it would create too much attention. He had a great thing going with Jess at the moment and he didn’t want to take any chances that might ruin that.

He sat at his desk, placed his headphones back in and started eating his lunch. Hoping that the end of the day would hurry-up so he could get the release that he desperately needed.


Jack couldn’t concentrate on his work, he spent the majority of the afternoon shuffling emails into different folders in a futile attempt to look like he was busy. He couldn’t get the images of Jess out of his mind. The way she smelled, the way she tasted, the lacey white underwear that he saw under her skirt.

His cock had been growing and shrinking all afternoon, driving him crazy with the pressure in his pants. Finally, the last few people in the office had packed up their belongings and said their farewells. Jack stood up while he packed his things into his bag, making sure that he couldn’t see anyone else in the office.

He took a short walk around the cubicles, finding no signs of life, before heading towards Jess’ office. He didn’t know exactly what to expect tonight. Jess had said that they would “take care” of his erection, she’d even touched it, but he didn’t want to assume anything. If she needed his help, he would assist her in any way that he could.

He approached the open door of her office and knocked on the doorframe.

“Hey, Jess?” He said as he poked his head around the corner.

He was met with an empty office, Jess’ desk sat unoccupied. Jack’s heart sank for a moment, desperately upset that Jess had left without telling him.


Jack spun around and saw Jess calling him from down the hallway, outside the meeting room that they had used last night. Her shirt was already half unbuttoned as she slowly motioned with one finger for jack to come down the hallway.

“I thought you’d gone home.” Jack said, making his way to her.

“With this level of engorgement? No chance.” She said, her hands lifting and dropping her breasts as she chuckled.

Jess walked into the meeting room and took a seat on the same couch as last night. She unbuttoned the remaining buttons of her shirt and patted the couch next to her.

“Come on, I need your help.”

Jess opened her shirt and unclasped her bra, letting her breasts fall free once again. Jack’s cock responded by becoming firm as he walked across the room and laid down on the couch. He rested his head onto her lap and looked up from below Jess’ swollen breasts. Her nipple was already starting to leak white milk as she lowered it to his mouth.

Jack greedily took the nipple into his mouth, starting with gentle sucking motions, letting the milk flow into his mouth immediately. Jess let her head fall back as she let out a small groan, clearly getting a great amount of pleasure from the situation.

Jess’s body tensed up slightly, indicating that her letdown was about to hit. Jack sucked slightly harder, rolling his tongue across her nipple as milk started to gush into his mouth. He eagerly swallowed Jess’ letdown as it filled the front of his mouth, trying to keep up with the volume that was flowing in.

“That’s perfect.” Jess whispered, her hand running through the hair at the back of his head and pulling him closer to her breast.

Jack took her lead and sucked harder, pulling as much milk out as he could, trying to emulate the rhythm that had worked for her during their previous session. A moan escaping Jess’ lips let him know that he had succeeded.

Jack watched from below as the pace of her breathing picked up, his tongue flicking back and forth across her nipple as he continued to suck at her breast. Jack’s pants crushed his cock as it hardened in his pants, becoming almost painful as it pressed against the fabric.

Jess’ hand suddenly grabbed hold of Jacks wrist slowly guiding it to her free breast. Jack immediately began playing with her nipple, feeling it harden between his fingers.

Jack used his hand and mouth to pleasure her, milk dripping into his palm as he gently played with her free nipple.

“Swap sides.” Jess whispered, letting go of Jack’s hair.

Jack stood up, his obvious erection pointing at Jess from behind his pants. Jess didn’t seem to notice as she stood up and pulled her white shirt off, before removing her bra completely. Jess stood in front of him, her bra falling to the floor.

“You don’t mind, do you?” Jess asked, smirking.

“N…no” Jack stammered, taking in the sight of his beautiful, topless boss.

“Good, because I don’t want to get milk stains on my skirt.” She said.

Jess reached for the small button at the top of her blue skirt, unclasping it and pulling down at the waistline. Jack watched her wiggle her backside as the skirt fell free, revealing her white lace panties, followed by her black thigh-high stockings.

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