Tom was nervous as he approached the tall building downtown. Just as he had at every other step of this journey, he hesitated at the door. Was this really the place? Why would such a rich place want him? And for the millionth time, he considered his few alternative options. He took a deep breath, straightened his jacket, and entered.
The lobby was very fancy, as he’d expected. One of the biggest law firms in the city, and he had the privilege to meet one of the partners. He had applied for the position of personal assistant, half as a joke and half out of desperation, and had been very surprised when he got a response. Even more when he got an interview with one of the partners.
He approached the only other person in the very large room, who was sitting at front desk clacking away at her computer.
“Hi, I’m Tom L-“
“Mr. Larson?” she said, without looking up from her monitor. “3 o’clock with Ms. Kenley?”
“Um, yes, that’s me.”
The lady continued to silently click at her keyboard. Just as he was about to speak up, the printer behind her whirred to life and she rolled her chair over to it. Out came a keycard with his name and the company logo, which she handed to him on a lanyard.
“Head down the hall and use the card to get past the turnstiles. You’re gonna take the fancy elevator. Don’t hit any buttons, just swipe the card again. She’s expecting you.”
“Thank you,” Tom said, but her attention had already returned to her computer and she gave no response, so he headed down the hallway.
Again he performed his ritual of second guessing at the turnstile before heading through. the elevators were easy to find, and the “fancy elevator” was unmistakeable.
The elevator faced the outside of the building, so Tom had an amazing view of the city as the elevator took him all the way to the top. He’d always thought that the city would be his escape, but it turned out to be just as oppressive as it was back home. At least here Tom could be himself.
The elevator slowed to a stop and dinged to mark his arrival at the 39th floor. The doors opened, revealing the fanciest waiting room he’d ever seen. This time there were a few secretaries and they were chatting, but their conversation stopped short as Tom walked in. One of them whispered something to the others that elicited some giggles, then turned and came up to Tom.
“Hi, you must be Mr. Larson.”
“That’s me. I have an appointment with Ms. Kenley?”
“Lucky you. She’s expecting you. I hope you do well, we haven’t had a cute boy working here in a while. She’s the room on the right.”
Tom blushed at being called cute but bristled at being called a boy. He was almost thirty.
“Thank you, I guess?”
“You’re certainly welcome. Best not to keep her waiting.”
He went to the door she indicated and heard more giggles. When he looked back the woman who greeted him gave him two thumbs up and a smile. Once again blushing, he opened the door and got his first look at the woman who invited him.
Lena Kenley, as the placard on her desk indicated, was a tall woman even while sitting. She had raven black hair tied tight into a ponytail, angular features, and dark eyes behind a pair of sharp looking glasses. She was wearing a charcoal pantsuit with blue jeweled cufflinks and matching earrings, and her nails were painted the same blue shade. Her attention was on a stack of papers she was writing on.
She gestured but did not look up. “Sit.”
Tom took a seat in one of the chairs across from her. The office was intimidating; floor to ceiling windows made up the right wall, and the left wall was bookshelves filled with what he could assume were mostly law books. The wall behind her had a very large portrait of a scantily clad woman seemingly in the throes of ecstasy. Tom tried not to stare at it.
After a minute of silence, Lena finished whatever she was writing and put her pen aside. She looked at Tom and he felt her gaze pierce into his very soul. He was now terrified of this woman. He would’ve gotten up and left right then if he had the courage.
She wordlessly turned her gaze to her desktop and started clicking. Tom let out a sigh of relief, then hoped it wasn’t loud enough for her to hear.
“Tom Larson.” He froze. She was still looking at her screen. “Your resume is… disappointing.” Lena pointed her gaze at him but he said nothing in response. “High school graduate, five years of college before dropping out, three other attempted career courses you abandoned. No work of any kind to speak of, other than a few months in retail. It’s honestly pathetic.” Her eyes once more met his. “Care to explain?”
“Yeah, I- um.” All the excuses in his head melted away. “I struggle with… well, almost everything. The tasks themselves aren’t hard, and when I can do them I do pretty well. It’s just that I… I just can’t do them.”
“And you’re on medication for this?”
“Yes. I’ve been on several for almost a decade now. It helps, but it can’t get me over the final hurdle. My therapist recommended applying for disability, but I was rejected.”
“And now you’re penniless, living out of your car, unable to afford the medicine you need just to complete basic tasks. Is that correct?”
“I…” How did she know he was living in his car? “Yes, ma’am.”
“My lady.”
“Oh… um, yes, my lady.”
“Tell me, Tom. What would you do if all your needs were met? Assuming you were unable to waste your hours away with video games. What would you spend your time doing?”
“I’d probably write.” When she didn’t respond, he went on. “I’ve got lots of ideas for stories in my head, and the thing I want most in this world is to get them on paper before I die. If I could, I’d spend my time doing that.”
“And what’s your sexuality?”
“I’m… I’m pretty sure you’re not supposed to ask me that.”
“If it’s a problem for you, then leave. Otherwise, answer the question.”
“Oh… um, I’m bi.”
“Now Tom, I ran a background check on you and it seems that you do have family not too far away. Why don’t you live with them?”
“It’s… complicated. I couldn’t be myself when I was with them, so I left.”
“Are they supporting you in some other way?”
“Also no.”
“And why not?”
“I’d rather not talk about it.”
“Again, if you’re uncomfortable with my questions you may leave. at any time”
Tom took a deep breath. “They disowned me for religious reasons. We’ve been no contact for a few years now.”
Lena nodded. “Very well. Now, about the job…” She turned the stack of papers in front of her and pushed them across the desk. “I imagine you’re looking for an office position.”
“The posting was for a personal assistant?”
“Yes, it was. That at least tells me you can read. However, I’m not sure that alone qualifies you for such a position.”
“I’m… sorry?”
“You should be. Your experience is abysmal. It’s no wonder you’re where you are now. Out of pity alone I’d offer you an unpaid internship just running coffee, but quite frankly I don’t even have faith you can do that properly.”
“Oh…” Tom blinked back tears. Why was she being so mean to him? “I thought you responded because you had something for me, but if you’re just gonna abuse me-” He got up to leave.
“I didn’t say you can go anywhere. Sit back down.”
He hesitated.
“Mr. Larson, if there’s one thing you should know about me it is that when I give orders, you’ll regret not listening. Now sit.”
He withered under her glare and sat.
She nodded. “Enough foreplay then.”
Lena took the papers in front of her and put them beside her desk, where it made a grinding sound as it went through the shredder. She then opened a drawer and pulled out another, much larger stack of papers, and set that down in front of him.
“This is the position you are applying for. Not a personal assistant, but a personal servant.”
Tom was confused. “Huh?”
“You will receive full benefits. Room, board, medical, dental. Every other weekend you will have off and you may do whatever you like during this time. You are guaranteed a minimum of four hours every day to yourself, as well as two hours that you will set aside for writing or other productive activities. You will have access to my services as a lawyer. or any other lawyer of your choice. You will also have access to one of my credit cards, although any purchases will not process until I approve them, which I may or may not do at my discretion. The remaining eighteen hours a day will belong to me. During that time you will have at least six hours of sleep, although it is not guaranteed to be consecutive nor regular, depending on my demands.”
Tom was almost salivating as he heard all this. He wouldn’t have to worry about anything ever again. Although something did bother him…
“So, essentially, I’ll be your slave.”
“No. You will still have a say in your activities, however, failing too many will result in the contract terminating. And remember, you will regret not following my orders. Think of it more like a roommate situation where you do all the chores and don’t have to pay rent.”
“What kind of chores?”
“Normal housekeeping. Washing dishes, keeping the place tidy, laundry, whatever else I may ask of you.”
“That’s it? Why not just hire a maid?”
“That brings me to the next, and primary obligation.” Lena straightened herself and looked him in the eyes. “I’ll be blunt with you, Mr. Larson. This arrangement will also exist to serve my sexual gratification.”
Tom had heard the word “dumbfounded” before, and while he thought he knew the meaning of it, he’d never truly understood until this moment.
” ‘Above all other responsibilities, you will provide me with sexual relief whenever and however I so demand it. You will be provided with a safeword, should it become too extreme for you, and other responsibilities will be waived should a particular session be too taxing.’ All this is in the contract.”
Seeing him still frozen, she continued.
“If at any point you decide you are unsatisfied with the job for any reason, you can end the contract by declaring so in writing with three signatures, each one written and dated no less than a day apart and no more than two. On such an occasion, you will be granted payment for your services equal to $5,000 for every full week spent under contract.”
“FIVE thousand a week??”
“However, I may also end the contract at any time, if you have either failed or refused too many tasks. If I choose to do so, you will be compensated with only $1,000 per week instead.”
“Is this a joke? There’s no way you’re serious.”
“Mr. Larson, I’m a very busy woman. I don’t have time to entertain vagrants, and even if I did, I don’t do jokes. Would you like me to keep going?”
“How do I know I’m not going to get screwed over? For all I know, I could be selling my soul, or something.”
“You will not be signing this today. If, at the end of the interview, we would both like to consider the contract, you will receive a copy to take home, as well as a stipend of $10,000, which should be enough to hire the services of any lawyer of your choice. Is that to your satisfaction?”
“You’re gonna give me 10k just for being here?”
She sighed. “No, Mr. Larson, I will give you ’10k’ for being a good boy and letting me finish. If we are both satisfied with the interview at its conclusion and you choose to take the contract home with you, the money will be in your account before you leave the building. Understood?”
Tom closed his mouth and nodded.
“Good, Now as I was saying, the contract will also expire naturally one year after signing. If this comes to pass, you will be given the choice to sign again. If you decline, your compensation will be $10,000 per full week served, for a total of $520,000.”
She looked up from the papers, as if expecting him to have another outburst at the amount. However, the number was too outrageously large for him to even consider, and he was left with a blank face.
She continued to drone on in legalese as he still processed that huge number. The things he could do with that kind of money… he’d completely turn his life around. Get a nice apartment, pay off his car, fix his wardrobe.
“So, Mr. Larson, what do you think of all that?”
“Let me get this straight. You’re going to pay me a ton of money just to have sex with me?”
“Oh, Tom. We won’t be having sex. I’ll be using you sexually. There’s a big difference.”
“And that is?”
“Whether or not you enjoy it is not a factor. All that matters is my pleasure.”
“So… free use, basically?”
“I see you’re familiar. Yes, essentially.”
Tom wanted to jump at the chance, but he played it cool. “I’ll have to think about it.”
“Of course. You’ll have two weeks to decide before the offer expires. Should be plenty of time to discuss it with your lawyer.”
“And I will.” He stood up and grabbed the contract, but she quickly slapped her hand on it. “Um. Is there more?”
“Yes, there is. As I mentioned earlier, in order to earn this contract, you’ll have to let me finish.” She tapped her desk.
“Okay…” She tapped her desk again. “Finish what?”
“Finish.” She more obviously tapped her desk with a pointing motion, and he hesitantly looked underneath it. “Consider it a test drive. I have to make sure I’m getting what I’m paying for, and it’ll be good for you to understand what to expect from me.”
Tom gaped. “You want me to…”
“Under the desk, if you please.”
“Right now? What if someone walks in?”
“Perhaps I haven’t been clear. If you’re uncomfortable, you may walk out now. Just keep in mind you’re walking out on ten thousand dollars.”
This was tough. Ten thousand could really make a difference. Not to mention the half a million if he just kept up with it. And it’s not like he’d never had sex before, even if his experience was limited. He honestly wasn’t too far from whoring himself out anyway. He knew he was pretty, it was probably his best asset.
“Okay,” he said, finally getting to his knees.
She just nodded as if she had fully expected him to give in. “Let’s see what you can do.”
He crawled under the desk. it was big enough that he had space, and it had an open front so he didn’t need to go around, although that meant he was easily visible from the door. He thought of the giggling women outside and almost lost his nerve, but the sound of a zipper took back his attention.
From this close, it was obvious that the bulge in her underwear was no pussy. He was taken aback by its size; flaccid in the blue panties, it was almost the full length to her hip. There was barely enough room for it, and her balls took up even more space. His first thought was that it must be uncomfortable, and he should free that beast.
“Don’t stare too long. You don’t want me to get impatient.”
He looked up at her and blushed, suddenly remembering where he was. He reached out and ran his fingers along the length of it. He felt it start to harden and grow, stretching the panties almost to the point of ripping before it finally poked its head out.
Tom pulled it out and measured it with his hands. It was easily almost ten inches long, and he could only just barely wrap his fingers around its girth. The pink tip glistened with precum which leaked steadily enough for him to lube his hand and her shaft.
He was mesmerized by its size and fell into the pattern of stroking it up and down, each upstroke gathering more of her pre, each downstroke letting that monster bob towards his face. It was beautiful, and he wanted to taste it, but its size scared him off every time.
“That’s good, but I’m not paying you ten thousand just for a handjob.” Lena’s voice broke his trance once again and he blushed.
He stammered “I- its- I haven’t-“
“Don’t be shy. Here, let me help.”
He felt her hand reach the back of his neck and pull him in. Suddenly he was being smothered against that hot steel-hard rod. He was forced to breathe in her scent – perfumed to smell like cinnamon, but this close he could smell her musk. It was intoxicating.
“Why don’t you start a little lower, if this is too much for you. Give my balls a smooch.” She pushed his head further down and used her other hand to free her sack from its cloth prison. His face was pushed against them until finally he relented and opened his mouth for a taste.
It tasted like it smelled, but here the sweat was more obvious. Her cock pulsed against his face and he felt its dribble run down his brow as he took one of her balls into his mouth. He tried every trick he knew; he sucked, licked, nibbled and kissed every inch of them, and before long he was making his way upward again.
Once again,as he ascended the size of her mast was impressed upon him. He kissed and licked and sucked and every inch he rose he thought, “surely i’ve almost reached the tip?” And every inch he was dismayed to find more waiting for him. He suddenly understood why she was willing to pay so much for a blowjob; the monster was enough to scare anyone off. The only things keeping him here were the promise of money and her hand on his head. He was halfway up the shaft when that hand suddenly pulled him away.
“I think that’s enough of that. Why don’t we move on?” She pointed her cock at his face and gave him a nudge from behind. “Open.”
Tom opened his mouth as wide as he could to get the head of her cock in. The salty taste of her precum assaulted his tastebuds as the monster pushed its way past his teeth. In an instant it was pressing against the back of his mouth, causing him to gag.
“You know how to deepthroat?” She asked.
His eyes bulged, then he tried to nod. “Mhm.” He’d practiced on a dildo a few times, but only tried on a real dick once. Though none of them were this big.
“Good, because I can’t cum until i’m balls deep. you ready?”
He tried to pull back to ask for lube, but her grip on his head stayed firm. Panicking, he started licking as much of her cock as he could, trying to wet the beast before it could ram down his throat.
“Oh good, I like an eager bitch. Here goes.”
With that, she pulled his head in. Tom had just enough time to clench his thumb in his fist – a trick he’d learned to turn off his gag reflex. Or lessen it anyway. Even so, he choked as it reached his throat. He took a deep breath in and tried to relax as she pushed into his gullet.
There was a sigh of pleasure from above him. “Oh, that’s nice and tight. And look at this, you can see my cock stretching your throat.”
He felt her hand on his neck stroke up and down. It tickled, making him squirm. She pulled his head back and he gasped as his throat was freed, but the cock didn’t leave his mouth.
“I think we’ll go all the way this time. Gag if you agree.”
He tried to protest, to get a little more time for air, but she pulled him in again, and the only sound he could make was choking on her rod.
“My, so eager. You must really want that money. Fine, I won’t keep it from you. Take it.” She pulled him in further.
This time she did not stop halfway down his throat. She kept pushing until his nose pressed against her trimmed pubic hair.
“Mmm, that’s good. But I hope you don’t expect me to do all the work. Let’s get going.”
She pulled him back a little, then pushed him down, slowly fucking his face. After a few back and forth, she stopped pushing and watched him do it on his own. Tom could hold his breath for a while, but it was getting towards his limit. His vision started to fade and he thrashed, and she let him pull out enough to breathe. After a few breaths, she pushed him back down.
This time, she wrapped her legs around him. One went over his shoulder and pressed against his back, pulling his body in, while the other folded across, resting her foot on her other knee, effectively locking him in place. He had just enough room to pull back enough to breathe, but no sooner had he reached it that she was pushing him back down again.
He kept going. In and out, stretching his throat on this beast. Every so often, she would loosen her legs enough for him to take a larger breath, but never for long. As he settled into a rhythm, Tom was able to sense things other than the cock stretching his gullet. Her hands had left his head, and he heard typing on the keyboard above him. She must be looking at porn, hopefully to speed things up. She wasn’t moaning or sighing anymore, though. The only indication she even realized she was being sucked off was her legs controlling his breathing.
This went on for what seemed like hours. The typing didn’t stop, and he didn’t hear any sex noises coming from the computer, so he had no idea what she was doing.
There was suddenly a knock at the door, and the sound of it opening. Tom was in the middle of a downstroke and scrambled to pull off, but Lena’s legs didn’t let him. When he realized she had no intentions of freeing him, he folded his body deeper under her desk and chair, hoping the intruder wouldn’t notice him.
“Ms. Kenley? Your 4 o’clock called, they’re hoping to move up the time.”
“Oh, good, I was just finishing the report. You can put them through.”
“How’s Mr. Larson doing? I see he’s trying to hide himself.”
“Yes, he is. He’s going to have to learn some things, it seems. I’m still deciding whether he’s what i’m looking for.”
“He looked cute. Anyway, I’ll go out the call through. Enjoy!”
“Thank you, Cassie.”
Tom finally heard the door close. He tried again to pull off, but she didn’t budge. She looked down at him.
“I have to take this call. They’ll be on speaker, so I don’t want to hear a noise out of you. Understood?”
Tom tried to mumble a response, which just came out as humming and gagging on her cock.
“It’s a yes or no. Just nod your head.”
He tried again to pull back, but to no avail. Finally, he nodded.
“Good boy. I’d hate for your interview to have to end after you’ve gotten so far.”
The phone rang and she answered it. Was she seriously doing work? He stopped moving, but she pushed him to keep going, so he did. She seemed to be getting off on it, as she started bucking her hips and pulling him during the call. He couldn’t make any sense of it, and doubted he could even if he wasn’t concentrating on sword swallowing, but he didn’t need to. Once he realized that, he turned his full attention to sucking her cock.
He sucked and licked and hummed on her rod. This was his job. This was what he was being paid to do. He didn’t have to worry about anything else, and so he didn’t. He focused on pleasuring it. He even started petting her balls with his hand. He breathed when she let him and just continued when she didn’t. She always seemed to know when he was about to run out of air, so he stopped worrying about that as well. All that mattered was her cock in his throat.
It seemed like forever when he heard her hang up. She pulled her chair back, dragging him with her from under the desk.
“You’ve done very well. I think It’s time to wrap up this interview.”
She stood up, and he prepared to get up as well, but her hand was on his head again and she didn’t let him off her cock. Instead, she pushed his head back so it was resting on the desk, not letting her cock leave his throat.
“Closing deals always makes me horny, so you’ll need to be ready to take care of it. I don’t want to take up too much of your time, Mr. Larson, so forgive me if I rush.”
With that, she started to fuck his throat. This was no longer the slow pace of occasionally bucking her hips, this was full on rutting. Her hips began to slam into his face as she slid her cock in and out. She held his head and moaned, ramming into him over and over again. Tom felt his head bruise and his throat was on fire, but she didn’t relent.
At a certain point, she stopped pulling out far enough for him to breathe. She had him pinned down and was fucking his face as hard as she could. He felt the air in his lungs get stale and try to escape. He struggled to pull away, but there was nowhere for him to go. He thrashed and slapped his hands against her hips, but she just grabbed them and pinned them to the desk, not letting up for a second. His lungs started to burn as she kept rutting against his mouth.
Finally, she sunk in hilt deep and let out a sigh. He felt her cock pulsing, depositing her load directly into his stomach. He tried to endure, knowing it couldn’t be long before she pulled out now that she came. He hummed on her cock to try and get her attention, but she seemed to be focusing too much on the orgasm to notice. Her cum was still pouring into him, and he felt his belly fill to the brim.
His vision started to blur and darken. He started to worry that she would never pull out and just stay there until he passed out. He began thrashing again, weakly, to get her to free him. She looked down at him and nodded, then pulled out.
Gasping, choking for air, he crumpled to the floor, finally released from suffocation. He almost vomited, but managed to hold it down. He doubted she would be pleased if he ruined her pretty blue heels.
She grabbed his arm and pulled him to his feet. “Thank you for coming in, Mr. Larson. You’ll receive payment shortly.” She walked him to the door, or more dragged him, as he was still in a stupor. “I have your number and email, so I will be in contact if I’m considering you for the position, and then you may respond.” She shoved a handful of papers into his hand and opened the door. “This is your copy of the contract. You may have your lawyer analyze it, and contact me when you’re ready to accept.” She pushed him out the door. “Have a good rest of your day.”
With that, she shut the door behind him. He blinked, not quite sure what to make of what just happened. He stumbled forward, trying to break out of his confusion.
“Oh, Mr. Larson! Tom, is it?”
Tom looked at the source of the voice and slowly managed to process it. It was one of the giggling secretaries. Cassie, he thought?
“It looks like Ms. Kenley approved your stipend, so you’ll be getting it… one second… now. She looked back up from her computer. “How was the interview? I know she can be rough, but it seemed like you handled it, huh?”
He tried to speak, but it came out as a cough, before he rasped “Yeah.”
“Good, good. I do hope you come back. Ms Kenley could really use you.” One of the other secretaries giggled, and the third shushed her, but held back a smirk.
“You may want to skip dinner. You can also use one of our bathrooms to clean yourself up before you go. Looks like you’ve made a bit of a mess,” she said, with a quick glance down.
Tom looked and found, to his surprise, he’d somehow managed to cum during that ordeal. He blushed and left as fast as he could.
In the elevator down, he was finally able to clear his thoughts. This was insane. He’d just been practically raped in the throat, and he came from it? And those secretaries knew, and acted like it was normal. What kind of place is this?
He checked his phone. Sure enough, there was an alert from his bank app telling him of a deposit. 10,000, as promised. Well. At least he could get a motel room for the night.
Tom sighed. This was all too much for him. He’d have to turn this position down. The money was alluring, but he couldn’t handle being broken like this. Although part of him did enjoy it. He’d never really done anything kinky before, and remembering how it felt to be on his knees with his mouth stuffed… it wasn’t as scary in retrospect as it was in the moment.
He dick twitched at the thought, and he suddenly realized how sensitive it was. How did he cum so hard without even noticing? Will it be that good next time? What even made him finish?
Wait. Next time?