Jack walked through the large glass doors of the office building, swiped his access card and called the elevator. He scrunched his face up as he sipped at his coffee; he was still trying to find a decent café close to work.
Jack had moved to the city just over two months ago, taking a well paying I.T job with Trig-Corp. It wasn't anything glamourous, but it paid a lot better than his last position and gave him the freedom to explore a new city.
His shy personality wasn't particularly conducive to making new friends, but the office had slowly warmed to him, inviting him out to drinks on a regular basis. He'd made new friends; he enjoyed the work.
He just couldn't find a decent coffee.
"Jacky-boy!" A voice called from behind him, just as the elevator door opened. "How was your weekend?"
Vince had become a good friend to him. He was loud and energetic, but he had a certain charisma that drew people to him.
"You know the wicked witch of the west is back today, yeah?" Vince said, putting a hand on his shoulder.
Their boss, Jessica, had been on maternity leave the entire time that Jack had been working for the company. He'd never met her, but from all reports, she ruled the office with an iron fist. Jack had worked for some pretty tough bosses in the past, he usually just kept his head down and completed his work, staying out of office politics as much as possible.
"Well, rest in peace, buddy." Vince said, slapping him on the back as the doors opened.
Jack stepped off the elevator and walked in the opposite direction to Vince, dropping his lunch into the fridge on the way to his desk. He sat down and booted his laptop up before noticing that no one else was sitting in his area. Jack stood up and saw that almost the entire office was congregated at the opposite end of the building, chatting and laughing away.
Jack immediately assumed that they were all welcoming Jessica back, and even though they had never met, he should probably show his face and welcome her too. Jack stood and walked the length of the office, joining the group at the back.
"Well, we are all happy to have you back." A voice said, a few halfhearted claps followed.
"It's nice to be back, now let's all get to work."
The crowd began dispersing, Jack let them pass, knowing that he should stay and introduce himself to the woman that signed his paychecks.
As the rest of the workers shuffled past, Jack got his first glimpse of the woman that was so feared around the office. Jessica was taller than average, her long legs covered in nylon, poking out from under a tight pencil skirt. Her blonde hair cascaded over her shoulders, coming to rest at the top of her plentiful breasts, the buttons of her white shirt straining to contain their volume.
Jessica pivoted and looked in his direction. Jack quickly snapped his vision away from her curves and lifted a hand to gesture hello.
"You must be Jack." She said, walking towards him, hand outstretched.
"That's me, nice to finally meet you, Jessica."
Jack took her hand and shook it, immediately shocked by the strength in her grip.
"Call me Jess, please."
"Nice to meet you, Jess."
"You too, management tells me you've settled in perfectly. I saw the work you did on the Craig file, keep up the good work."
Jack was taken aback, from all reports, Jess was supposed to be terrifying. She'd been described as an office dictator, but from first impressions, she seemed lovely, professional, and absolutely gorgeous.
"Back to it." Jess said, turning and walking to her office, closing the door behind her.
Jack returned to his desk, slightly more optimistic about his future with the company now that he had met Jess. He had told himself that he would play it by ear until she returned from maternity leave, and if they clashed, he would simply quit and move back home.
Now his future suddenly seemed much simpler.
The need to find a decent coffee place grew more urgent, however.
Jack plugged his headphones in and started listening to music, working away on his new portfolio until his alarm went off. He had developed a bad habit of getting lost in his work and missing his meal breaks, his phone was now in charge of reminding him to eat.
Jack walked to the kitchen to heat up his leftover pizza, signaling to the world that he was indeed a single man. Vince sat at a table, chatting with a few colleagues, he motioned for Jack to join them.
"Jacky-boy. Did you meet the ice-queen yet?" He asked, chuckling away.
"I did, she didn't seem so bad." Jack said, diplomatically.
"She always seems like that at first, you just wait."
Jack didn't respond, he didn't like talking about people behind their backs, especially not in a workplace.
"She gets more breaks than the rest of us too, did you know that?" Vince asked, addressing no one in particular. "She closes the blinds in her office and pumps milk out. Whenever she wants, isn't that unfair?"
Jack grabbed his pizza from the microwave and walked out of the kitchen, not wanting to get involved in the drama.
"Where are you going, Jacky-boy?" Vince called.
"Work, Vince, I'm flat-out today." He called back.
It wasn't a lie, he was busy today, but mostly he just didn't want to sit listening to people gossip. He returned to his desk, put his headphones in again and slowly munched away on his rubbery pizza.
About an hour later an email from Jess came through. It outlined some improvements that he could make, constructive criticism and suggestions. The email had a small picture of Jess in the top corner. Jack saw that she had brown hair in the photo, it must have been from a while ago.
He then noticed how small her breasts were in the photo, having a child must have tripled her size, possibly even more. Jack was amazed at just how much difference between the woman in the photo and the one he met today.
Jack felt a stirring in his pants when he thought about the size of her breasts. He thought about her in her office, blinds closed, pumping milk out from her huge tits.
Jack shook his head and took a mouthful of water, trying to expel the images from his mind. The last thing he needed was to be known as the new guy, who got a boner at his desk.
He put his head down and started working again, telling himself that the faster he got his work done, the faster he could get home and jerk off to relieve the pressure.
He focused on a large project and put his mind to work. It wasn't until his stomach started growling that he realised the sun had set. Jack looked around the office and saw that everyone had left for the day. Feeling pretty stupid, he packed his desk up and headed for the elevator.
Just as he was about to press the button, he heard a voice coming from across the office.
"Just fucking work!"
Jack recognized Jess' voice straight away. It was full of frustration, rasping at the end of each word. He reached for the button again but stopped just short. Part of him just wanted to leave, but if there was something that he could help Jess with, he wanted to show his value.
Jack put his bag down and began walking, the light coming from Jess' office acting as a beacon.
"Fucking piece of shit!" Jess shouted, followed by a bang.
"Jess?" He called out as he arrived at the half open door.
"Who's that?" Her voice called back.
"It's Jack, the new guy, are you okay?"
Jack heard Jess let out a breathy sigh, clearly upset with something. He was starting to wish that he had just left the building.
"Yes, Jack, I'm okay. You can come in."
Jack pushed the door open the rest of the way and entered her office. Jess looked flustered, something had made her angry and Jack was hopeful that it wasn't him.
"Why are you still here? It's past eight o'clock." She asked, her frustration audible.
"Sorry, I get carried away sometimes."
"Your wife must be a very patient woman." Jess said, smirking.
"Oh, I'm not married, it's just me and the T.V at home." Jack replied, trying to lift the mood.
"Still, you shouldn't work so late, it's not healthy."
"Well, you're here late too." Jack said, jokingly.
"That's different." She said, her smile fading slightly.
Jack wasn't exactly sure what was going on with Jess, he decided that he would offer his help and try and get into her good books.
"I heard you yelling, is there something I can help with?"
Jess looked embarrassed, she clearly thought that the office was empty when she had shouted earlier. Her head turned to a small, yellow object, laying on the ground at the opposite end of the room.
"If you must know, my breast pump stopped working." Jess said.
"Oh, right." Jack said, now convinced that he should have taken the elevator and gone home.
"It takes me nearly two hours to get home and I'm already engorged." Jess said, her hands gently rubbing across the top of her voluptuous breasts. "So now I have two options; ride the train home in pain, leaking the whole way. Or sit here, manually expressing myself for another hour before I can leave."
Jack stood in the doorway, completely stunned by Jess' frank words. He felt a stirring in his pants, his cock reacting to the image of her manually expressing in her office. He needed to leave as fast as possible to avoid Jess seeing him get a full-blown erection.
"Damn, that sounds horrible. I'll head off so you can have some privacy." Jack said, turning towards the door.
"Wait." Jess called, stopping Jack in his tracks. "Wait, there is one other option."
"What's that?"
"Well, you said you're single right?" Jess asked.
"Uh, yeah." Jack replied, confused.
"Well, maybe, you could help me out with this?" Jess said, her hand moving under her heavy tits.
"Help you out?" Jack replied, trying his best not to imply anything that would get him fired.
"Look, I wouldn't ask if I wasn't desperate. I'm sore here." Jess said, her eyes pleading with him. "It would be just between us. Never mentioned again."
Jack took a step back, completely shocked by what she was asking him.
"Wait, you want me to..." Jack's words trailed off.
"You don't have to; it would just help me out a lot." Jess said.
Jack's brain was busy with different scenarios, most of them ended with him getting fired for trying to grope his new manager. But, as per usual, his cock was telling him that this might be his one chance to do this.
He hadn't been with a woman in nearly a year, the stress of looking for a new job and moving cities took the fun out of dating for him. In front of him was an absolutely stunning woman, practically begging him to touch her breasts, and he was considering turning down her advances. He had to decide if it was potentially worth his job.
"So, you want me to...milk you?"
"Well, Jesus, I'm not a cow, Jack." She replied sternly. "I want you to help me express."
"I've no idea how to do that." Jack said, wanting to be perfectly honest.
"It's not hard, you just suck, Jack."
"Suck!?" Jack repeated. Up until now, he assumed he would be using his hands to help her.
His cock started swelling in his pants, letting him know what it thought of the conundrum.
"Yes, suck, Jack."
"What about your husband?" Jack asked.
"I'm not married, I'm a single mother." Jess said, wincing as she rubbed the top of her breasts. "Now I need you to make a decision here, Jack. If you're not going to help, then I need to get started on my own."
Jack was shocked to hear that such a beautiful woman was single, and a working mother too, Jess continued to impress him. He was becoming more convinced by his cock with every passing second and had basically made up his mind to help her already.
"Okay, but this stays between us, right?" he asked.
"Absolutely." She assured him.
"Okay, how do we do it then?"
Jess immediately stood from behind her desk and approached Jack. Her right hand unbuttoning her top as she walked.
"Quickly follow me." She said.
Jack followed her as she led him to a meeting room around the corner and walked to a long couch inside. She sat at one end and unbuttoned the rest of her shirt, exposing her white bra to Jack, his cock instantly springing to life. Jess unclasped a small hook nestled in her cleavage and let her engorged breasts fall free, swaying gently as they came to a rest. Her light brown nipples stood firm, small white drops of milk forming at the end then rolling down her tits.
"Lie down here." Jess said.
"Lie down?"
"That's the only position I know how to do this in. Now hurry, I'm sore." Jess pleaded.
Jack didn't hesitate, he approached the couch and laid down on his side, facing Jess. His head fell into her lap naturally and he looked up at the gorgeous sight above him. He could smell her perfume now that he was closer to her, his cock making a tent in his pants as he absorbed her in with all of his senses.
"Okay, open your mouth." Jess said.
She put one hand on the back of his head and leaned forward, placing her hard nipple into his mouth. Jack took the breast between his lips and sucked, immediately receiving a gush of milk into his mouth. It didn't taste like regular milk, it was sweeter with a slightly metallic aftertaste, but definitely wasn't offensive.
"Ahh, that's it." Jess said. "You're going to trigger my let down, keep going."
Jack wasn't exactly sure what she meant until a stream of breast milk hit the back of his throat. He spluttered a bit and pulled away from the nipple, only for jets of milk to shoot him in the face. He quickly put the breast back in his mouth, not wanting to be completely covered in breast milk and continued sucking.
"That's my let down, you're doing great." Jess said, encouraging him.
Jack's cock was growing uncomfortably hard in his pants, the situation far more arousing than he had expected. He knew that lactation porn was a thing, but he'd never had any interest in the genre. Now, within a few minutes of sucking at Jess' nipple, he knew why it was such a popular kink. It was incredibly erotic; there was something so feminine about the way Jess held the back of his head. He knew that their friendship, and their working life, would be changed completely by this.
"Are you ok?" Jess asked.
Jack nodded his head, not wanting to take his mouth off her tit.
"Good, you're doing great, that one already feels so much better." She said, leaning her head back against the couch. "A few more minutes and we can change sides."
Jack looked up at her, captivated by the way she controlled the situation. She was stern, but kind, gently guiding him through this new experience.
He continued to suck her for a little while longer before she let go of his head and started pulling her breast away.
"Okay, stand up. I'll move to the other end of the couch and you can do the other one."
Jack hesitated for a moment realizing that he had no way of hiding his raging erection from his new boss. He quickly decided that he had no real choice in the matter and stood up.
Jess noticed the bulge in his work pants immediately.
"Oh, well, I guess that makes sense." She said.
"Sorry." Jack apologized.
"Don't be, I won't tell a soul." She replied, moving down the couch.
Jack laid back down, her hand guiding his head to the fresh breast.
"That's it, drain me, Jack." Jess said, her voice hushed and breathy.
Jack suckled at her nipple, trying to savor every drop. His cock ached in his pants, wanting to be set free and touched, but he didn't want to ruin what he had going for him.
Jess' head fell back against the couch as her hand ran through Jack's hair. He watched as her breath quickened, a slight moan escaping her lips.
"She's enjoying this." Jack thought to himself, as he increased the pressure behind his suction.
Jess gently played with his hair, moaning gently, in a trance like state. Jack took a mental picture of this moment, not knowing if he'd ever have this chance again, with anyone.
"Nearly there. Just a minute longer." Jess said in a whisper.
Without realizing what he was doing, Jack lifted his hand and gently held the side of her breast. He felt the weight of it in his hand, the soft skin sliding under his fingers. Jess looked down at him, her eyes initially confused, before letting her head fall back into position on the couch, a smile on her face.
Jack gently groped her breast as he sucked firmly, rolling his tongue across her hard nipple. Jess shuddered, goosebumps forming across her chest, before she suddenly sat forward, taking her nipple out of his mouth.
Jack watched as milk dripped from her nipple, now twice as long as when he had started sucking.
"Okay, gosh. That is probably enough for tonight." She said, using the inside of her bra to wipe at the excess milk dripping from her breast. "Thank you so much, Jack. You really helped me out."
Jack got to his feet, his erection still bulging out the front of his pants. Jess was arranging her bra when she looked up and saw his predicament. She looked at her watch and pondered for a moment.
"I've got about five minutes before I need to leave and catch my train." She said. "If you can finish in that time, you can look at them while you take care of that."
Jack took a moment to comprehend what she was offering, but as soon as he had grasped the concept, he started undoing his belt. He let his pants drop to the floor and pulled his cock from his pants. His raging erection pointing directly at Jess.
"Well then." She said, looking at his cock. "It's always the ones you don't expect that have the big packages."
Jack had always been happy with his cock size, it wasn't porn star massive, but he'd never had any complaints about it.
Jack began stroking his cock with ferocity. Not only was he incredibly horny after draining Jess' milk, but he was also on a time limit. Jess lifted her huge breasts, pushing them together for Jack to view as he stroked his cock.
"This is a one-time deal, so take them in." Jess said.
Jack could see white drops forming at the end of her delicious nipples as she pressed them together.
It took only a few moments and he could feel his balls swelling, getting ready to come. Jess smiled her beautifully white teeth at him as they made eye contact, sexuality emanating from her. That was enough to push him over the edge.
Jack took a step back, his balls contracting as his rock-hard cock erupted with cum. He hadn't thought about where he was going to ejaculate, he just let the thick white ropes of cum fall onto the floor between them. His abdomen convulsed as pleasure ran through his body, his eyes clenched shut.
He stood there for a few moments, basking in the afterglow of his orgasm, until Jess interrupted him.
"Well, you're cleaning that up." She said.
Jack opened his eyes and saw her buttoning up her shirt, her breast hidden from his view again. She stood up and straightened her skirt, pulling her stockings up her legs a few inches.
"Thank you very much, Jack, but I need to make my train." She said, walking to the door. "And remember, not a word of this to anyone."
"No, of course not." He replied.
"Good." She said walking out of the office. "You've got a lovely cock, Jack, but clean up that mess before you leave."
Jack stood alone, his pants around his ankles, trying to come to terms with what had just happened. If it weren't for the taste of Jess' milk in his mouth, he would have thought that he had dreamed the whole thing. He reached down and pulled his pants up, tucking his still firm cock into his pants.
Jack found some paper towel from the kitchen and wiped his load of cum from the office floor, disposing of the towel in the bin on the way to the elevator.
Jack left the building and walked to his car. He spent the whole trip home reminiscing about what they had done, how her breasts felt in his mouth, the sweet taste of her milk. As soon as he got through the front door of his apartment, he took his pants off and sat on the couch.
He opened his phone and immediately searched for "lactation porn", finding thousands of results. He watched them for the better part of an hour, stroking his cock again as he watched women squirt milk from their nipples.
Some drank their own milk, others poured glasses and fed them to men. He especially liked watching women lactate while they were orgasming, there was something so sensual about it. Just as he was about to finish himself off, a notification came through on his phone.
It was a text from an unknown number.
Jack, this is Jess. Just wanted to thank you again. I got home without any pain thanks to you. See you at work tomorrow.
Jack smiled at his screen, pleased that he was able to help her out so much. He began typing another message to her when Jess sent a picture through to him.
Jack's jaw dropped, his cock springing to life. Jess sent a picture of herself, completely topless, milk dripping out from both of her breasts.
This is to show my thanks.
Jack started stroking his cock again, looking at Jess' massive tits. He couldn't believe that he had been sucking on them just hours ago. He felt the familiar sensation of his balls tightening up, preparing to come, before leaning back and spraying his work shirt with cum. It wasn't a huge load like the one earlier, but it was more than he expected.
Jack slowly recovered from his orgasm and removed his cum covered shirt, before picking his phone up and replying to Jess.
Thank you! You look amazing in that photo. See you at work.
Jack laid back on the couch and slowly drifted to sleep, completely exhausted by his day.
He was slightly concerned about how tomorrow would go; he didn't know if it would be awkward between them or if it would just be fine. Her sending him a picture of her breasts was probably a good indicator that everything would be fine.
Jack fell asleep thinking about Jess' nipple rolling across his tongue.
*
Jack walked through the doors of Trig-Corp, swiped his access card, and pressed the button for the elevator. He sipped at his coffee and was pleasantly surprised, it was pretty decent. He wasn't sure if it was the new café he had tried or if he was just in a good mood.
"Jacky-boy!" Vince called out. "Ready for another day of fulfilling work?"
Vince slapped him on the back, laughing loudly at his own joke. Jack was beginning to wonder if being friends with Vince was more effort than it was worth.
"You know it." Jack mumbled as the elevator opened, the two walking in opposite directions.
Jack approached his desk and began setting up, saying hello to his colleagues before heading to the kitchen to put his lunch in the fridge. Just as he was about to enter the kitchen, Jess appeared in the doorway. She was wearing a white top again, this time with black lace around the collar, a blue skirt covering her stockings. Jack's cock started to stir in his pants, just at the sight of her.
"Oh, hi, Jack." She said. "I sent you an email that I need you to take a look at first thing this morning."
"Oh, Sure thing." He replied.
Jess walked past him, leaving him to put his lunch in the fridge. Jack was shocked at how professional she had acted after what had happened last night, but he was also thankful that there wasn't any awkwardness between them.
It was a one-time thing, just like she had said. He helped her in a time of need, and he was rewarded with a picture of her amazing breasts. Now their relationship had returned to a completely professional one.
Jack sat back at his desk, a little deflated by the knowledge that their fun was over, but also thankful that he experienced it, and had gained a new fetish to watch online.
Jack opened his email and clicked on the urgent mail from Jess.
His eyes opened wide as he read the message, his cock becoming hard in his pants instantly.
Jack, this project is taking longer than expected. I'm going to need you to work late every day this week.
------X------
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 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 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 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.
"Hey!"
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.
Jess picked up her skirt and placed it on the meeting table, then took a seat at the other end of the couch.
"Does that thing ever go down?" She asked, pointing at the bulge in his pants.
"Not around you." Jack said, taking in the sight of the gorgeous woman in front of him.
Jess simply smiled and patted the couch again, inviting him to start on her other breast.
Jack happily obliged, placing his head down on the top of her stockings. The lace of her panties only inches away as she lowered her breast into his mouth.
Jack opened his mouth and took her other nipple in; it was already leaking from him playing with it. An immediate rush of milk filled his mouth, spreading across his tongue as he started swallowing. He couldn't believe that she had undressed in front of him so casually, letting him rest his head against her almost naked lap. She smelled different without her skirt on, more raw, more natural. It made his cock twitch, aching in his pants again.
Jack suddenly felt a hand on his cock, Jess seemingly sensing his discomfort.
"Let's give this guy some fresh air." She whispered, unbuttoning his pants and lowering the zip.
Jess reached into his underwear, her smooth hands sliding over the shaft of his rock-hard cock. She wrapped her hand around it and pulled it free from his underwear.
"Now that is a nice cock." She said, slowly sliding her hand up and down the length of it.
Jack's eyes rolled back in his head as he reached for her other breast, immediately stimulating her other nipple as he continued to suck milk from her. Jess started jerking him off, her hand firmly grasping his cock, her nails occasionally reaching out and stroking his balls.
"Does milking me turn you on this much?" Jess teased.
Jack nodded his head, refusing to unlatch from the nipple.
"Well, I guess I'll just have to make you my personal milking assistant." Jess said, picking up the pace of her hand around his cock.
Jack moaned with her nipple in his mouth, her words sending shivers up his spine. He was so incredibly turned on by the situation, he could feel his balls beginning to tighten, preparing to come.
Jack felt a hand slide past his head as Jess slid a hand down her panties. He watched as she slowly started to rub her pussy underneath her white lace panties.
"Are you going to come for me?" Jess whispered.
That was all that Jack needed, his balls hugged tight to his body as he started to convulse. His eyes clenched shut as his cock began to erupt with cum, spraying rope after rope against Jess' hand and the couch. He turned his head involuntarily, a loud groan falling out of his mouth as he exploded with an enormous orgasm.
Milk ran out of Jess' nipple, dripping onto his face and running down his cheek as he twitched in the aftermath of his orgasm.
Jack's world went dark for a moment, nothing outside of that office existed for a few moments as he processed his climax.
When he opened his eyes, he looked up at Jess, her breasts still dripping onto his face. She was casually licking his cum from her hand, smiling at him while she did so. Jack's cock twitched again, the sight of her tasting his cum was enough for it to start to harden again already.
Jess' other hand began to move as she removed it from her panties. She gently placed her wet fingers across Jack's face before sliding them into his mouth. He smelled her aroma and tasted the juice from her fingers, eagerly sucking at them, trying to memorize the flavor.
"Only fair that you get to taste me too." She said, pushing her fingers deep into his mouth, then sliding them all the way out.
Jack looked up at her, in complete awe. There was something so deeply sexual about her, everything she did was dripping with sexuality, and Jack wanted to lick all of it up.
"Okay, you're on clean up duty again." She said, shifting her body weight to stand up.
Jack lifted his head, letting her stand up. He looked at the mess that he had made on the couch and knew that he needed to clean it up quickly. A puddle of his cum sat on the cushion of the couch, more of it dripped slowly down the back cushion.
Jess pulled her skirt over her panties, her bra and shirt followed soon after.
"I need to make my train." She said, straightening her hair. "I had a wonderful time though."
Jess moved towards him and kissed him passionately, her tongue pushing its way into his mouth. She reached down and grasped his shaft one last time, squeezing it firmly.
"Thanks again." She said, turning and leaving the room.
Jack heard the elevator door shut as she left the office, leaving him with his cock out and a couch covered in his cum.
Jack put his cock away and went to retrieve paper towel again.
He gathered his things and headed to his car. It wasn't until he was driving that the reality of the situation hit home. A smile spread across his face, his cock twitching as he thought about Jess sliding her pussy covered fingers into his mouth.
He couldn't get her off his mind for the rest of the night.
Jack knew he was falling for Jess already, and he didn't care.
------X------
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.
"What?"
"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 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 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 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.
"There he is." She said grabbing his shaft firmly. "He's been very patient."
Jess pushed Jack backwards, making him sit on the couch again. Jess fell to her knees and moved between his legs, holding his cock the entire time. Without hesitation, she leaned forward and took Jack's hard cock into her mouth. Gently moaning as her tongue rolled across the head of his member.
"Jesus, Jess." Jack whispered, taken by surprise.
He was expecting to help her with her engorgement again, maybe get a hand job, but here was this incredible woman between his legs, with his cock in her mouth.
Jess took his cock deep into her mouth, sucking firmly, before bobbing her head up and down rhythmically. Jack felt his balls tighten immediately, the events leading up to this blow job already making him need to cum. Jess sensed this and slowed down, taking his cock out of her mouth and kissing the shaft gently.
"Mmm, it's been so long since I've had a cock." She said, taking the head back into her mouth.
Jack's eyes rolled back in his head, completely overwhelmed by the sensation. Jess' body rocked back and forth, thrusting her head down onto his rock-hard cock. Jack watched her, she was clearly enjoying herself as she sucked him, her head bobbing up and down. She looked up and made eye contact with him, the lust in her eyes exciting him even further.
Jess took his cock out of her mouth and leaned back, revealing her dripping nipples.
"Want a taste?" She asked.
Jess stood up, not waiting for an answer, and mounted Jack's lap. Her knees resting on either side of him, his hard cock pressed up against her stomach. Jess leaned forward and placed a breast in his mouth, a jet of milk instantly filling his it. Her hand grabbed hold of his cock and began stroking it while he nursed at her nipple.
"That's it, drain me." She whispered.
Jack reached up and started stimulating her other nipple, milk covering his fingers as he gently rolled it between his thumb and forefinger. Jess' hand picked up pace rubbing his cock against her stomach now. She let out a deep, primal moan as he sucked firmly on her thick nipple.
Jess sat up ever so slightly, her nipple still in Jack's mouth, and began rubbing his cock against her clitoris. Jack could feel the ball of her piercing against the head of his cock as Jess quivered with pleasure.
He looked up the beautiful woman that he was only an inch away from being inside. She looked so sexy and so powerful riding above him like that. Jess looked down at him and their eyes met.
They didn't need to say anything, they both knew what was about to happen.
Jess smiled as she angled Jack's cock a little bit further back, then lowered herself onto it taking his rock-hard cock into her wet pussy. She moaned deeply as she slowly slid down his thick shaft, her lips gripping him tight.
"Jesus." She moaned, "It's been too long."
Jess pulled her breast from his mouth and leaned back, focusing on riding him. She started slow, grinding against him while she took the entire length of his cock. Then she sat up and started bucking her hips, fucking him as deep as she could manage.
"Fuck me, Jack." She hissed, her pussy becoming wetter by the second.
Jack thrusted into her, pushing her hips down onto his cock, driving it deeper into her. Milk started dripping from her swollen breasts, flicking around and splashing them both while she rode harder and harder.
Jack reached out and held them, teasing her nipples as he drove his cock in and out of her. He knew he wouldn't last long; he wasn't sure if he ever could with such a sexy woman, but especially not today after such an intense session at lunch time.
"I'm going to come soon." He said, panting slightly.
"Cum in me, Jack." She said.
"Are you sure?"
"It will be fine, I'm still breast feeding." Jess insisted.
Jess started bucking harder, Jack's cock slipping in and out of her soaking wet pussy with ease. He felt that familiar feeling in his balls, the feeling that told him he was at the point of no return. Jess must have felt him swelling too, she leaned forward and planted a deep kiss on him. Her tongue meeting his in a moment of intense passion.
"Do it for me, Jack."
Jack felt the words flow from his ear, through his body and into his cock, which promptly erupted with cum. Jack convulsed as wave after wave of orgasm washed over him, cum pouring out of his cock and filling Jess' pussy.
"That's it, come in my pussy, Jack." Jess whispered, nibbling at the lobe of his ear.
Jack's vision blurred for a moment as the climax of his orgasm hit, his cock shooting out one last thick rope of cum inside Jess.
His limbs went limp, and his eyes shut, nothing else existed except for Jess and her wet pussy enveloping his cock. He felt her gently kissing his neck, her breast still dripping milk onto his chest and stomach.
"That was so good." She whispered, sitting up and letting his cock fall free.
Cum poured out of her as she stood up. Jess put a hand between her legs to catch some of it and licked it from her fingers.
"Tastes better when it's both of our juices." She said winking at him.
Jack's cock started twitching again at the sight of her licking his cum, but it had started to soften already. He couldn't believe what had just happened. He couldn't believe that he got to do these things with such a sexy woman.
He couldn't believe he had just cum inside his boss.
"I've missed my train." Jess said, looking at her watch. "Any chance you could give me a lift home?"
Jack's mouth wasn't working, he was still recovering from his orgasm, he simply nodded his head.
Jess leaned forward and kissed him, the taste of both of their fluids filling his mouth.
"I'll make it worth your while."