After hours of pouring over the Smithson account, there came a gentle knock at Jake’s office door. Looking up from the paperwork, he called out, “Come in.” The door swung open and a woman in her late twenties strode in. Her hair was long and wavy, cascading down her back in loose curls that bounced with each step. The light brown locks catching the soft filtered sunlight, giving it a golden sheen. Jake’s attention was immediately drawn to her belly, round and protruding, showcasing the miraculous life growing inside. Despite being pregnant, she carried a stack of files with ease, her swollen belly adding a slight waddle to her step.
“Hi Jake,” she greeted, her deep brown eyes sparkling with warmth as she gave him a brilliant smile, “I’m Shayla Winston, the client relations manager.” She chuckled adding, “Although, manager is a funny title, since I work alone.”
As she approached his desk to deliver the files, he couldn’t help but notice how her large swollen breasts delightfully jiggled with each step and how a neatly trimmed patch of matching pubic hair peeked out from between her legs. He found himself smiling at her natural beauty. When she dropped the files on the corner of his desk he noticed her gold wedding band. “I saw Jessica in the hallway heading your way with these files and I offered to bring them to you myself. I wanted to introduce myself, although I feel like I already know you after having dinner last night with Em and Rachel.”
“Nice to meet you Shayla,” Jake replied, his eyes flitting across her nude form before coming to rest on her cherub-like face. “Should I be worried about what was discussed during dinner?”
Shayla laughed, the sound melodic and carefree. “Oh no, not at all! I just needed to see you for myself,” she winked playfully, “so stand up and let me have a look.”
Feeling slightly self-conscious being completely naked in front of her, Jake slowly stood up from his desk. “Very nice,” she exclaimed appreciatively, taking in his toned physique and slightly swollen penis. “Now turn around so I can see that cute little butt.”
Jake obliged, feeling a tinge of embarrassment at being ogled like this. As she walked by him heading to the sitting area, she playfully slapped his butt with a giggle causing his cock to twitch. “Looking good,” she teased then sank into the soft leather sofa cushion with an audible sigh. “Feels good to be off my feet for a bit, you don’t mind, do you?” she asked.
“Not at all,” Jake replied as he walked over and sat down beside her, “feel free anytime.”
“How far along are you?” he asked looking at her heavy breasts and rounded stomach, feeling a tingling in his groin.
“Seven months and it’s been quite the journey,” Shayla answered, her hands gently cradling her belly as a tender smile played on her lips. “I can’t believe how fast it’s going.”
Jake nodded, his eyes traveling over the curve of her stomach, entranced by the visible signs of life within. “It must be an incredible feeling,” he commented, his voice a mix of awe and curiosity.
“It really is,” she agreed, her large eyes gleaming with enthusiasm. “Every kick and flutter feels like a little secret shared between me and the baby.” She paused and then, with a cheeky grin added, “But it also comes with its share of challenges. Like keeping my balance with this extra weight up front.”
Jake laughed, appreciating her humor. “I can only imagine. But you seem to be handling everything beautifully.”
Shayla’s face softened with gratitude at his words. “Thank you, Jake. That means a lot.” She shifted slightly, making herself more comfortable on the sofa. “So tell me about yourself. How are you finding things around here?”
“Well,” Jake began, shifting to face her more directly, “it’s definitely been an… interesting experience so far. The work culture here is quite… unique.”
With a playful raise of her eyebrows, Shayla agreed, “This is true. It’s not every day that you witness a heavily pregnant, naked woman waddling into your office wanting you to fuck her.”
Jake stared at her in disbelief. He knew the dynamics in the office but she was pregnant and married. He looked at her with a stunned expression on his face as he processed her blunt proposition. His initial shock soon gave way to a cautious curiosity. “Is that something you’re comfortable with?” he asked, his voice laced with concern yet tinged with intrigue.
Shayla giggled, the sound rich and unburdened. “Of course,” she assured him confidently. Her eyes held an impish glint as she continued, “To be frank, pregnancy has made me super horny, and I find the freedom here… liberating.”
Jake felt his pulse quicken as he absorbed her words. He watched as Shayla shifted again, her movements deliberate, showcasing the fullness of her breasts and the curve of her belly in a way that was undeniably alluring. “What would your husband think about it?” Jake asked skeptically.
“Brian? He knows the basics of my job and where I work, but not the more… unconventional parts of the office environment. I adore my husband, but I believe it’s best to keep my professional life and personal life separate. Understand?” she answered.
“I see,” Jake murmured, his gaze fixed on her. The lines between professional and personal blurred further in that moment, the unconventional atmosphere of the office making this conversation seem almost normal.
Shayla smiled at him warmly, reaching out to touch his arm gently. “Don’t feel obligated,” she said softly. “I know my condition might not be a real turn on but I just thought… hey, why not extend the offer?” Her touch was light but sent a flush of heat through his body.
“It’s not that I don’t find you beautiful or don’t want to have sex with you, I do, it’s just…” Jake hesitated.
“What?” Shayla asked running her hand down his arm and into his lap lightly grazing his stiffening member. “Don’t be shy.”
“I’m a little nervous,” Jake admitted, fidgeting with his hands. “I’ve never been with a pregnant woman before. Will I accidentally hurt… the baby?”
Shayla’s expression softened with understanding. “Well, she might grab at the tip if you’re in really deep.”
Jake’s eyes widened in shock, his face paled. “What?!”
Shayla couldn’t contain her laughter. “Oh my god, Jake,” she snorted, “that was a joke! You won’t hurt the baby, you goofball. Now stand up.”
Shayla perched on the edge of the couch, her legs spread wide. Jake rose from his seat and positioned himself between her legs, peering down at her. She placed her hands on the back of his thighs, her fingers slowly sliding up until she firmly gripped his buttocks. She pulled him in closer and began to lightly kiss his flaccid member, coaxing it back to life. Jake’s breath caught, his heart beating wildly as he felt her lips trace a slow and deliberate path from the base to the tip. “You seem to be enjoying this” she murmured between kisses, looking up at him with a twinkle in her eyes.
“Oh, yes,” Jake gasped, his voice barely a whisper. He watched, mesmerized, as Shayla took him into her mouth, her tongue swirling around the head of his penis before taking him deeper. Her hands continued squeezing his bottom drawing him into her, sending pulses of pure pleasure through his body.
As Shayla’s movements became more fluid and confident, Jake’s hands found their way into her hair, gently guiding her rhythm. The sensation was overwhelming; the warmth of her mouth combined with the occasional flick of her tongue was driving him close to cumming. But he didn’t want to rush this; he wanted to savor every second.
After a few moments, she slid his cock out of her mouth with a soft pop and stood up, her desire evident in the pink flush of her cheeks and the rise and fall of her chest. “I really need to be fucked,” she confessed, her voice husky with longing.
Jake wasted no time, guiding her to the side of the sofa, pushing the coffee table aside, and haphazardly throwing the cushions onto the floor behind him. With a swift motion, he pulled on the handle and opened the sleeper sofa, revealing the cozy mattress inside. “Well that’s a pleasant surprise,” Shayla remarked, as anticipation tingled through her body.
Jake took her hand and guided her to the bed laying her down gently in the center of the king-sized mattress. She looked up at him, her eyes filled with desire. “I really need this,” she whispered, reaching up to pull him closer.
Jake responded by planting a soft kiss on her lips, savoring the taste of her mouth before trailing kisses down her neck and across her collarbone. He paused to admire her swollen belly, brushing his hand tenderly across the roundness that seemed to electrify Shayla with primal lust.
Lowering himself further, Jake began to kiss around her breasts, taking special care to arouse her with gentle licks and nibbles. Shayla moaned softly, tangling her fingers in his hair and pulling him closer. When Jake’s mouth finally captured one nipple, sucking lightly at first and then increasing the pressure, Shayla arched her back off the mattress, whispering urgent encouragement, “Yes Jake, suck my titties.”
Encouraged by her reaction, Jake moved his hand between Shayla’s legs, finding her already wet and ready. His fingers dipped into her warmth as his mouth continued sucking on her swollen nipples. Shayla gasped at the dual sensations, her body beginning to writhe under his touch.
She let out a desperate exhale. “Please fuck me, Jake,” she pleaded.
Jake positioned himself between her legs, lifting them up and gripping her ankles. He slowly entered her with his hard length, causing Shayla’s eyes to widen with the sensation of being completely filled by him.
Jake started moving in slow, deep strokes, watching Shayla’s expression shift from intense pleasure to overwhelming bliss. With each thrust, he felt more connected to this incredible woman who had opened herself up to him so completely. His rhythm intensified as he sensed her nearing the edge. Shayla’s moans became louder, her body trembling with each movement. Her hands clawed at the sheets, gripping tightly as waves of ecstasy cascaded through her.
“Harder, Jake… please,” she gasped, her voice cracking with urgency. Jake obliged, his movements becoming more forceful, driven by the raw primitive desire he saw in her eyes. He leaned forward and her swollen belly rubbed against him provocatively with each thrust, reminding him of the life within her and adding an intoxicating sense of awe to their coupling. “Don’t stop,” she panted. Jake let go of her ankles and leaned back feeling the tension building within him, his thrusts growing erratic as he neared his own climax. He reached down and circled her swollen clit with the pad of his thumb, determined to bring them both over the cliff together.
Shayla’s response was immediate and intense; she arched her back and let out a loud cry, “Cum in me Jake, cum in my pussy.”
As she convulsed beneath him, he was in awe of the sight of her in such euphoria. Her vaginal walls tightened around his cock, flinging him over the edge. With one final deep thrust, he gave in to the immense sensation and released his seed inside of her. Shayla lifted her head to look him directly in the eyes, her expression unbelieving. “Did you just cum on my daughter’s face?” she asked, a hint of disapproval in her tone.
Jake, his cock still buried inside her, looked horrified, “Oh Jesus, Oh fuck… I am SO sorry, but you said…” he pleaded.
Shayla burst into laughter, her breasts and belly jiggling with each convulsion and pushing his softening, slippery cock out of her. “Oh Jake, you’re too easy,” she chuckled as she gasped for air and tears ran down her face.
Jake started laughing and collapsed beside her on the bed, his heart still racing from the rush of their fuck and the shock of her joke. “Ok, you got me,” he admitted, catching his breath as he nestled closer to her.
Shayla wiped the tears of laughter from her cheeks and smiled, her eyes softening with affection. “Even though you’re really gullible, you sure know how to please a woman,” she giggled, her hand lightly stroking his chest.
After a moment of comfortable silence, Jake spoke up, his voice thoughtful. “I never imagined working here would be like this… It’s mind-boggling but also incredibly freeing.”
Shayla was quiet for a beat then spoke, “It’s not just about the sex, Jake. It’s about trust, respect, and exploring your boundaries in a safe environment. We’re all here because we believe in this philosophy.” Jake nodded appreciatively, feeling reassured by her words.
“Thank you, Shayla. I am really happy that you decided to deliver those files for Jessica.” They lay in silence, the only sound in the room was their synchronized breathing.
Shayla propped herself up on one elbow, her belly pressing against his body, and looked down at him with a playful gleam in her eye. “Mr. Thompson,” she said, “would you mind escorting me to the shower and assisting me in getting cleaned up? I can’t exactly go back to my office with your cum seeping out of my cooter.”
Jake grinned, “No, I suppose not.” He got up from the bed and took her hands, guiding her to the bathroom. He turned on the shower and adjusted the temperature, making sure it was just right before helping Shayla step under the warm spray. The water cascaded over them to wash away the remnants, but not the memory, of their sexual encounter.
As Shayla stood under the flowing water, Jake gently began to lather soap over her body. His hands moved with care, sliding over her curves and paying special attention to her bloated belly. Shayla closed her eyes and leaned into his touch, savoring the feeling of his fingers gliding across her skin.
“You know,” Shayla murmured, “there’s something incredibly intimate about being bathed by someone else. It’s not just about being clean; it’s about being cherished.”
Jake smiled, continuing his ministrations. “I can see that,” he replied softly. He poured some shampoo into his hand and began to massage it into her hair, his fingers skillfully working through the strands.
As he rinsed the soap and shampoo from her body and hair, they continued to chat quietly about life, work, and their personal philosophies on love and intimacy. The shower became less about cleaning and more about connection, each moment enhancing their bond.
Finally clean they stepped out of the shower and dried off with the fluffy white towels. Jake couldn’t help but feel a sense of contentment wash over him as he looked at Shayla.
Shayla caught him staring and laughed gently. “Go on, get out of here, I need to dry my hair and make myself presentable.” Jake playfully slapped her bare ass and left the restroom, leaving the door open.
As he walked into his office he noticed that Emily was there folding the bed back into the sofa, replacing the discarded cushions, and repositioning the coffee table, “I see you met Shay,” she said, with a grin, as she sat down.
Jake chuckled, drying his hair with a towel. “Yeah, she’s quite the character,” he replied, still feeling the warmth of their earlier encounter.
Emily gestured to the empty spot next to her on the sofa. “Come, sit and tell me everything.” Her playful tone was mixed with genuine interest. Jake could feel her gaze on his swinging cock as he walked over and took a seat. He could sense the change in the air as Emily leaned in closer, her curiosity apparent.
“It was intense,” Jake admitted. “But she also taught me a lot about what this place is really about. It’s not just physical, it’s… deeper.”
Emily smiled knowingly. “Yeah, it can be pretty amazing when you connect with someone on that level. So,” she nudged him playfully with her shoulder, “do you think you’re starting to understand our little company?”
“I think so,” Jake said thoughtfully. “It’s different, but there’s a sense of freedom and acceptance here that’s really refreshing.”
“That’s exactly it,” Emily agreed, her hand touching Jake’s thigh and giving it a gentle squeeze. “We’re all about exploring and enjoying without judgment.”
“Oh, hey there Em,” Shayla said as she entered the office from the restroom and walked over towards the sofa.
“You are absolutely glowing,” Emily replied.
“A good fuck will do that to a girl.” she said as she winked at Jake. Jake blushed slightly then stood and offered Shay his seat next to Emily. As she walked by him Shayla playfully squeezed his genitals causing Emily to snicker.
“I need to look over those files that Jessica sent over, I will give you two a chance to talk.” Jake said as he headed towards his desk.
Shayla sat down next to Emily, the two friends very comfortable being nude together as they chatted and laughed, sharing stories and details of their individual adventures from the day. Shay placed a hand on Emily’s inner thigh in a casual display of intimacy between friends. Emily turned to Shayla, lowering her voice slightly. “So, how was he?” she teased, nodding towards Jake who was now absorbed in his work.
Shayla’s eyes sparkled as she leaned closer to Emily. “Oh my god, Em, he made me cum SO hard.” she confessed softly, her voice tinged with genuine admiration. “He’s attentive and curious – exactly what you hope for in this kind of environment.”
Emily nodded knowingly, looking at Jake at his desk across the room. “I thought you would like him. He has a really nice cock.” she said with a smile.
Shayla giggled, squeezing Emily’s thigh playfully. “And he sure knows how to use it,” she replied.
Emily leaned forward and tenderly caressed Shayla’s pregnant belly. “So, Jake,” Emily spoke up talking to the back of Jake’s desk chair, “Are you enjoying your first day of work?”
Jake swiveled in his chair to face the two stunningly beautiful naked women, his voice taking on a distant and dreamy quality. “It has been… enlightening,” he responded, recalling the vivid memories of being sucked off by Rachel as Emily masturbated for him, and more recently, fucking Shayla’s pregnant body. The memories sent a rush of warmth through him and his penis responded, starting to stiffen. Shayla and Emily’s eyes widened slightly at the sight of Jake getting hard again and they exchanged a knowing look.
Shayla walked over to Jake, her hips swaying naturally with each step. “Looks like you’re ready for more,” she teased as she reached down to gently stroke his penis, glistening precum forming on the tip.
Emily, came over and knelt down in front of Jake’s chair, looking up at him as she wet her lips seductively with her tongue. As Emily leaned forward, Shayla bent his pulsating cock towards her face and Emily deftly slid it into her willing mouth. Jake groaned at the pleasure of being ensconced in Emily’s warm, wet mouth. Shayla released his member and gave him a kiss on the forehead, “I need to head home to my husband.” she whispered.
Emily mumbled a goodbye with Jake’s swollen cock filling her mouth. “Bye Shayla, see you tomorrow,” Jake said with a small wave.
After Shayla left the office, Jessica entered to see how Jake was doing on his project. The only sounds in the office were the guttural moaning and slurping coming from behind Jake’s desk. Jessica silently approached the desk and stood next to Jake’s chair watching Emily blow him. Jake had his head resting against the back of the chair and his eyes closed enjoying the delight of Emily’s mouth. Emily looked up at Jessica, Jake’s cock going in and out of her mouth, and winked. Jessica smiled and gestured that Emily should continue what she was doing.
“I would like to get your thoughts on the Smithson account, now that you have had the day to look it over,” Jessica said looking down at Jake. Jake’s eyes flew open and he struggled to focus, his breaths shallow and erratic as Emily’s warm mouth continued to work wonders on him. He stretched his memory, trying to grasp the details of the Smithson account amidst the intense waves of euphoria.
“Uh… yeah… um, the Smithson account,” Jake managed to stammer, his voice trembling. “I think we have a… a solid approach. Their interest in expanding into the European market could be key.” Emily’s cheeks hollowed and she began rapidly bobbing her head on his shaft. “Oh, fuck,” Jake breathed and then cleared his throat. “We… uh, might want to leverage our connections in Germany and France.”
Jessica nodded thoughtfully, her hand resting on Jake’s shoulder. “That’s an excellent strategy,” she praised, her eyes glancing briefly at Emily who was now slowly swirling her tongue around the head of Jake’s cock. “And what about risk mitigation? Have you given that any thought?”
Jake swallowed hard, trying to gather his thoughts. “Yes, we should… um, definitely propose some contingency plans. Perhaps hedging foreign exchange exposure and considering local partnerships could reduce potential risks.” His words trailed off as Emily took him all the way into her mouth, her nose pressed against his pubic bone as she locked eyes with Jessica, sharing a silent communication.
“Excellent suggestion,” Jessica agreed, her tone all business. She leaned closer, her breath warm against Jake’s ear as she placed a hand on his chest, feeling his rapid heartbeat, and seductively whispered, “Emily’s a good little cocksucker, isn’t she?” Jake nodded breathing rapidly.
Emily suddenly intensified her efforts, drawing a deep moan from Jake that filled the room. Jessica straightened up watching Jake’s slick cock completely disappear into Emily’s mouth and nodded her approval. The room reverberated with the sounds of wet suction and Jake’s increasingly labored breathing as he edged closer to climax. Jessica watched intently, her eyes filled with a mix of professional admiration and sensual desire. “Cum, Jake,” she encouraged, her voice a soothing caress in the heated atmosphere. “Cum all over Emily’s pretty face.”
The tension in Jake’s body built to its peak as Emily’s techniques became even more focused and precise. Her hand cupped his balls gently squeezing, while her tongue flicked rapidly across the sensitive underside of the head. Jake’s response was a guttural groan as he surrendered to the rising bliss. His back arched slightly off the chair, pushing himself into Emily’s eager mouth. His mind was a blur of erotic pleasure intertwined with the strategic points of the Smithson account, creating a surreal blend of professional achievement and sexual fulfillment. With one last skillful twist of her tongue, Emily pulled him out of her mouth pointing his member directly at her face just as Jake erupted. As Emily stroked, ropes of thick white ejaculate shot out, landing on her glasses, nose, cheeks, and lips. She looked up at him grinning through her cum covered face. “Very well done, Jake,” Jessica said as she reached down and wiped a thick glob off Emily’s glasses and slid her finger into her mouth tasting his semen. “You handled that beautifully. Both the presentation and your release.”
Jake, still catching his breath, managed a weak smile. “Thank you,” he gasped out, looking down again at Emily whose face was completely covered with his sperm.
Emily stood and Jessica took her by the hand leading her out the door.
Jake laid back in his chair completely drained and overwhelmed by the intensity of the experience. The room was quiet now, the air still thick with the scent of sex. Jake sat in quiet for a while before his mind slowly shifted back to the room. He spent the last part of the workday glancing over the Smithson account again.
—oOo—
After leaving Jake’s office, Emily and Jessica walked quietly down the hallway until they were out of earshot. Jessica spoke, “Boss lady wants to see us.” Emily responded gesturing to her face, “Maybe I should get cleaned up first.”
“No time,” replied Jessica, “we’re already late.” Emily shrugged her shoulders nonchalantly, Jake’s semen sticky on her face.
Jessica and Emily approached Margaret’s office door, its polished wood gleaming. As they entered, their eyes were drawn to the large conference table that dominated the room. Seated around it were Margaret, Rachel, and Shayla, their bodies nude but their faces serious and focused. The two women took their places in two open chairs, joining the group as they settled into the meeting. The air was tense with anticipation as they waited for Margaret to begin.
Margaret adjusted her glasses, the light reflecting off the lenses as she surveyed the women around the table with a stern yet expectant gaze. “Ladies,” she began, her voice clear and authoritative, “I want to hear your initial thoughts on Jake.” Her eyes flicked momentarily to Emily’s cum covered face, a small smile tugging at the corners of her mouth. “He seems to be just what we needed in the office, wouldn’t you agree?” A quiet chorus of consensus passed among the group at the table.
Shayla leaned forward, her enlarged belly touching the table edge, her expression one of calculated interest. “He also has quite the stamina.” She ran a hand through her thick hair. “I think we should explore how far it can extend.”
Rachel’s soft voice added, “I have to agree with Shayla. His performance today, both with Emily and me, and then again with Shayla, was truly exceptional. We should make use of his cock as much as we can.”
Jessica, quietly absorbing every word, finally spoke up. “Emotionally connecting with him through these experiences is just as important. We can use our ‘training sessions’ to not only explore his physical boundaries but emotional ones as well.” Her motherly figure shifted, her expression thoughtful.
“Emily, what are your thoughts?” Margaret inquired. Emily beamed at being addressed directly, the drying cum on her face flaking off with her smile. “I think he’s genuinely curious and open to new experiences,” she said enthusiastically. “I think today was intense for him,” she smiled remembering, “But he handled it well. I am sure we can bring out deeper aspects of his desires, maybe push him a little more on the emotional side as Jess suggested.”
Margaret nodded appreciatively at Emily’s input, her eyes thoughtful behind her glasses. “Very good,” she replied. “Making sure Jake continues to feel engaged while we explore these boundaries will be key to him being willing to delve deeper.”
Shayla, couldn’t resist jumping in with a mischievous smile. “And we can’t overlook the sheer pleasure it brings us. It was a real treat to have him ravish my pussy this afternoon.” The room filled with nods and laughter as the women agreed with her.
“Ok, It sounds like we’re in agreement, Jake’s a keeper,” Margaret declared, her tone resolute as she surveyed her team. “Before we adjourn, I want to mention one more thing. My granddaughter, Kiera, is on her break from high school and will be starting an internship with us for the summer. She will be joining us on Wednesday. I have discussed our unique environment with her, but she may still be a bit shy. I ask that you all make her feel welcome and utilize her in any way you see fit.” The women all expressed their understanding and agreement before standing up and heading towards the door.
“Jessica, please remain a moment.” Margaret requested. Once the others had left the room and closed the door, she continued, “My granddaughter is quite inexperienced when it comes to sexual matters. In fact, I believe she’s still a virgin. I realize that our office environment will be a lot for her to take in. I feel for the good of the work environment, she will need to experience sex and I would like it to be with Jake. I want you to facilitate it happening.” Jessica felt uneasy about the request but nodded slowly before leaving the room.
—oOo—
Jake glanced at the clock on his computer screen and decided it was enough for the day. He carefully arranged the papers and folders on his desk, aligning them in neat stacks before turning off the lights. As he left his space he noted that the office was quiet and seemed almost deserted, which felt odd. In the locker room, he retrieved his clothing from his designated cubby, wondering in his solitude as he dressed in silence. With a sense of accomplishment and anticipation for what tomorrow would bring, he made his way home, ready to relax after completing his first intense day on the job.
Thanks for reading. Likes and favorites are greatly appreciated and your comments are always welcome.
