Her first day

It felt so different than usual. Walking into work was something you’d done a million times, but this time you were walking in together with your fiancé. A few of your coworkers seemed to look up and take notice at the new and unfamiliar addition to the office staff as you led Jill up to the door to Shaun’s office. As management, he had his own room that was well furnished and spacious while you worked in what was effectively a cubicle. “Here we are! You ready for this?” You asked her, noticing that the very edges of her hot pink bra were now just barely visible beneath her blouse with the way she’d unbuttoned her blouse a little more in the car. “I think so… wish me luck” she told you, sounding both nervous and maybe a little excited. She opened the door and you heard Shaun greet her. “Jill! There you are… good morning! You got my email about your dress code, right?” You heard him ask. “Yes… I hope this is alright… um… I-” she started to say, but then the door closed behind her. You wondered about what type of dress code Shaun might have insisted on. He was a strict boss, so it sort of made sense he would be particular about how his assistants presented themselves.

You went about your normal workday for a while until you eventually got up to see about getting a second cup of coffee. The company provided a coffee machine and the materials for it, and you enjoyed the fact that it was free even if the quality was mediocre. The one drawback was sometimes there was a line. Your coworkers Jeff and Henry were standing in front of you gossiping as they got their own coffee. Their desks were close to each other in the office, so they’d become quite chatty over the years.

“You see Shaun has some new secretary or something?” Jeff, the thinner and younger of the two asked.

“Yeah I did… kind of strange for him to be bringing on new people when he’s supposed to be slashing jobs.” The middle-aged and slightly overweight Henry replied.

“I don't know man… I know why I’d hire an assistant like that.” Jeff said with a smirk.

“Oh yeah? Why’s that?” Henry asked with an amused and expectant towards at his friend.

“Well… I saw two BIG reasons as soon as she walked in the doors” Jeff said with a grin, and Henry laughed.

“You might be onto something there! Shaun definitely knows how to pick them…” Henry agreed as they walked off sipping their coffee.

You felt a little embarrassed by the exchange you’d overheard. On the one hand, it was nice that other men thought you had a hot fiancé. But you hadn’t actually pointed out or explained that she was your fiancé yet. If anyone looked closely at the pictures on your desk they’d obviously work it out, but so far you hadn’t really drawn attention to the fact. And somehow interrupting Henry and Jeff’s crude banter didn’t seem like the opportune time for that. And wouldn’t sending out a mass email welcoming your own significant other be kind of cringe-inducing? Sooner or later it would come up naturally, you told yourself. It was getting to be close to lunchtime, so you decided to check on how Jill was doing. First you texted her, but she didn’t reply. After that, you walked over to Shaun’s door. As his new assistant, odds were good she’d be in there, unless she’d run to the printer or something to that effect. You listened at the door to see if Shaun was in a meeting, and when you didn’t hear any obvious voices, you knocked on the door.

For a moment, you thought you heard hushed and urgent whispers on the other side of the door, but then a much clearer and louder voice rang in. “Come in.” Shaun called out. You opened the door and saw Shaun seated at his desk with his fingers steepled on the table in front of him. He raised an eyebrow. “What is it, Andy?” He asked, sounding even more impatient than usual. You glanced around his office, and there was no sign of Jill. “Sorry to bother you, I was just looking for Jill… since it’s almost time for lunch.” You explained, hoping it wasn’t too stupid of a reason to bother in. Shaun sighed. “I have her taking care of a few things for me. It may take her a while, depending on her skill level.” Shaun told you, and he shifted forward in his seat. You heard something hard hit the back of his desk and you glanced down, wondering if he’d stubbed his toe against it. “Was that all?” He asked quickly, seeming tense. His hands spread out across his desk and you saw one tightly grip one of the arms of his chair. “Yes, sorry sir. Just tell her to stop by my desk when she has a minute.” You told him, moving to leave. “Close the door.” Shaun ordered you, and you did.

As soon as you’d left the room, Shaun leaned back in his chair and looked down beneath his heavy mahogany desk. There was Jill, on her knees beneath his desk. Her blouse and pink bra had been cast aside beside her, and her big tits were spattered with a few drops of her own drool. She had been giving Shaun a deep and sloppy blowjob when you had knocked on the door. She had been terrified by the situation, but Shaun had ordered her not to stop. Jill thought to herself that it had felt so wrong… she had been licking up and down your boss’ shaft while he was ordering you around. She couldn’t believe how much power Shaun had over you. Even still, this situation had been way too risky for her liking. “Can’t we at least lock the door?” Jill protested quietly, but she nonetheless took the head of his dick back inside her mouth. Each bob of her head on his big dick making her big tits bounce. Shaun’s hand tightened into a fist beside her, which brought a frightened expression to Jill’s face. “You don’t tell me what to do. And you’re going to need to do a lot better if you want lunch with your wimpy little boyfriend.”

Jill’s lips withdrew from Shaun’s cock with an audible pop. She gazed into his eyes and nodded. “I’m sorry. Please don’t be mad at him. I’ll make it up to you.” She promised, taking him inside her mouth and forcing herself to deepthroat his long and thick cock. She took inch after inch until she let out a pained groan and gagged on his dick. Despite **** and tearing up, she **** herself to keep taking his big dick that deep down her throat. She told herself it was all for you. It was only when she had pushed herself like this that she’d been able to make him cum last time. Sure enough, as she willingly choked on your boss’ thick cock under his desk, his body tensed and he once again clutched his armrests tightly. “Fuck yes… **** on that dick bitch…” he growled, and even though he was insulting her and she could barely breathe, she couldn’t help but gaze up into his eyes. When he couldn’t take anymore, he pulled back, withdrawing his cock from her warm mouth, and he urgently stroked his cock towards her face. Jill took her heavy breasts in her hands and squeezed them together, opening her mouth and sticking her tongue out. Giving your boss the perfect target to cover her face and tits with his cum.

Shaun groaned and his cock throbbed, shooting a huge load of his hot and thick cum across your fiancé’s face. She gasped as part of the cum rope splashed across her tongue, and she shuddered at the now familiar taste washing over her again. Another shot soaked her face further, but the next got less distance and instead splashed across her big tits. Once the last of the spurts had passed, Jill bit her lip and moaned. “Was that good enough for you Shaun?” She asked quietly, withdrawing her cum soaked tongue and loudly swallowing. “Good enough for now.” Shaun said tersely, and Jill nodded in silent obedience. “But I want you to stay late tomorrow.” Shaun told her. She looked up at him, and then, grasping what he was suggesting, she looked down at the carpet. “Yes sir…” she murmured, collecting the cum from her tits on her fingers before guiding it onto her tongue. The taste was intoxicating and so distinctly manly. She took a last glance at his long dick as he pulled his pants back on, briefly wondering if it could really fit.

You held off on taking your lunch break, still wanting to take that time together with Jill. Eventually she finally texted you back. “Coming!” She replied simply, and soon she exited Shaun’s office and walked over to you. “Hey! How has the first day been treating you?” You asked her. She blushed and looked at the picture of you two together on your desk. “Well… I don’t know…it’s going to take some getting used to…” she said, avoiding your gaze before she quickly changed the subject. “So… where do you usually eat here?” She asked. “Oh, there’s a few great spots to sit outside when the weather is nice. I’ll show you the ropes, don’t worry. You must be starving, you haven’t even eaten yet today, have you?” You asked her. Strangely this made her face flush and she hesitated. “Um… right, yeah, nothing at all…” she said. As you led her outside, she was a little quiet. “Is everything okay honey?” You asked her. She quickly nodded. “Yeah! I just- uh… with some of the trainings and stuff I have to do, it seems like I might need to work kind of late tomorrow…” she said. “Oh… well if we’re carpooling, should I stick around and wait for you then?” You asked, and her eyes widened.

“No!” She blurted out, and your expression must have looked pretty startled because she quickly continued. “No, I don’t want you to have to wait around for me… I could always catch a cab, or… maybe I could just have Shaun drop me off at home.” She said slowly. You raised your eyebrows at that. “I don’t know… I don’t think he’s the type that likes to carpool with the workers very much.” You said, and she gave you a look which was strangely sad, almost pitying. “Um… well… I think he might make an exception for me.” She said. “Really? Well it’s good you guys are getting along well so far. So you actually like his management style? A lot of people find him kind of stern and abrasive.” You told her, surprised by what she’d told you. “I could definitely see that, but…” She paused and looked into your eyes. “I like it a lot…” she said quietly.