—

The job market was incredibly harsh. Henry had been without a job for over six months and was becoming increasingly desperate for work as he emptied the remainder of his savings. Rejection letters continually poured into his email, and that didn’t even include the multitude of no-responses. He stared blankly at the screen, contemplating just working in fast food like he did in college. Something was better than nothing, he reasoned. Then, as though the world could sense his defeat, an email with the title “First Interview” popped into his email. Almost immediately he opened it and began reading the contents within. 

“To Henry,

Thank you for applying to the role as executive assistant! We’d like to extend an invitation to you for the first interview. As a  sign of dedication, we expect you at our office immediately after reading this email. Please wear business attire and come ready to speak with the executive who you will be assisting. All candidates are encouraged to put their best foot forward in the running for this exclusive role. The annual salary is typically $150,000 but may vary depending on the candidate.

Hope to see you soon,

Starlight Inc.”

Henry couldn’t have ripped out of his chair any quicker to throw on his suit. He checked his watch to find the time to be a tad past 2:30. He fixed his hair, brushed his teeth, and quickly started up his car. This was going to be his lucky break. 

—

“Hello there,” he greeted the woman at the desk. “I just received an email for the executive assistant role and I came here as quick as I could.” The woman smiled, looked back at her computer screen, clicked the mouse a few times and dialed the phone.

“Yes, Henry is here to see you.” She informed, before giving a slight pause. “Sure thing.” 

The phone clicked as she returned it back to its cradle. “She will be waiting in her office down the end of the hall,” she directed while pointing over her own desk.

Henry followed her finger, straightened his tie and approached the door. He timidly peeked around the corner of the door, feeling slightly awkward to enter without knocking. His eyes spotted the back of a woman’s chair who twirled around at the sound of the opening door. Henry prepares himself to greet her, when she finally stands up and begins walking towards him. With each step, her size become more and more apparent until finally she is looming over him. An enormous hand reaches out to meet his own.

“Well aren’t you a tiny little thing,” she noted before grabbing his hand and part of his arm. “I like you already.”

Henry was so rattled by her size, he couldn’t even mumble a response. Yes, he was definitely small at 5’2’’ but she was… huge. His neck craned up to meet her smiling face, and it must have been obvious what he found so shocking because she quickly jumped to inform him of her height.

“I’m 8’1’’ before you ask.” She stated. “Or maybe you weren’t going to ask, since I have apparently scared you into being mute.” 

The towering woman turned from the encounter and rounded her desk and then gestured for Henry to sit. “Come take a seat. We’ll go over your resume and you can tell me about your experiences more in-depth. I’m Miss Pointe by the way. 

“Sure Miss Point, I’ll take a seat. Sorry for my poor introduction. My name is Henry and I’m very excited to be here.” 

She side-eyed Henry and let out a small grin as he sat in the chair. Almost immediately she began parsing through his resume, seeking something to discuss or elaborate on. At the conclusion of her quick scan, she became very aware of Henry’s skill set… or more so, what was lacking.

“So I see you don’t have any prior experience as an executive assistant.” She began, now raising an eyebrow, “Why is that?” 

“Well Miss Pointe, I must say, I just really need a job right now, but as you can see there, I’ve held many corporate jobs and can’t see why this would be much different.” 

“I see.” She muttered while continuing to scroll through the resume. “Do you have a problem doing anything I may require of you, even if it is not to your liking? I need to be able to trust my executive assistant to handle a lot of important tasks that impact my day to day.” 

“Yes, absolutely I can.” Henry confirmed, feeling more confident than before.

Miss Pointe stopped scrolling, spun her chair 90 degrees, and looked Henry straight in the eye. She leaned back, causing her chair to creak from the immense weight, and then lifted her long legs to set two giant heels onto the table. The red bottoms reflected in the light.

“Well what other skills do you bring to the table, little Henry?” She questioned, now fiddling with her perfectly manicured nails.

“Well,” he began, now unsure of how to sell himself for the position, “I… uh… I have the ability to organize calendars, I can write up documents for you, or make spread sheets for any meetings you have. I’ve made a ton of PowerPoints and can leverage…” 

“Oh wow! “ she interrupted. “That all sounds fantastic. But…” she paused, “I need to know how good you are at… sucking toes.” 

She lifted her eyes from her nails to see him squirm for a moment before responding. “Sorry, did you say, know how good I am at sucking toes.” 

“Yes that is exactly what I said.” She affirmed, now somewhat annoyed. 

“Well I have never really sucked anyone’s toes,” he admitted, now fearfully eyeing the enormous set of feet before him. 

“Oh… so you’re a toe sucking virgin?” She asked emphatically.

“Yeah I guess you could say that.” Henry answered, knowing all too well how much he needed this job.

“Well if you don’t mind, “ she started, her eyes darting to her heels, ”just take those off and you can show me your natural god-given talent.”

Henry watched as she wiggled her feet back and forth on the desk to emphasize their presence. “You want me to—“ 

“Yes, I want you to take my fucking shoes off and suck my toes like you need this fucking job.” She said slapping the table with a balled fist, now exploiting his desperation.

Henry looked up at her stoic face and then again back down at the awaiting heels, which eagerly clicked together. He reached a hand out and fiddled with the back of her heel, managing to pop it free. He slid his fingers into the musty opening before carefully prying away the rest of the shoe, exposing her giant sole. The reddened skin actually seemed clean for the most part, which was a relief. On the other hand, this woman had some long toes. 

“Hmm that fresh air feels wonderful on my feet. Look at how pretty my toes look.” She stated while wiggling them for her own enjoyment. “I bet they are just as long as your little fingers. Do me a favor, try and wear that little toe ring around your finger.”

Henry looked to meticulously painted black toes and spotted the ring in question. It was secured to her second toe, and hung out about halfway down the lengthy digit. Henry maneuvered himself closer to her foot, and was about to pry her toes apart to snag the ring when she interrupted again. 

“Whoa now, little man.” She cooed with an evil grin. “I need you to suck it off.”

Henry’s fingers slid down between her toes to create some space for his lips. Her claims about her toes being longer than his fingers seemed very real now as he finessed them apart until his mouth was able to insert her second toe. The pad of her toe hit his tongue first, leaving a subtle pop of salt as his mouth wrapped around the remainder of her toe. He slid further and further down until the ring finally surpassed his lips. Like a suction cup, his lips pursed firmly around the toe before pulling upwards and removing the metal ring. 

“Got it” he exclaimed, somewhat excited from the achievement. 

“Now put it on.” 

Miss Pointe was rather interested in seeing if the ring fit. Henry fumbled with it until finally sliding it over his pinky. Too big.

Then he slid it over the next finger. Too big. Then the next, and the next and the next until no more fingers were left to try. 

“Wow, you are so petite. Can’t even use my toe ring.” She laughed. “Now don’t forget my other toes.”

Miss Pointe enjoyed tormenting her new little assistant. The little guy was really giving it his best effort. But she knew there was still more to give and she was gonna take it.

Henry looked at her foot once more and sighed. He set the ring on the table and leaned in towards her foot to finish the job. This time he grabbed her foot a bit more aggressively and plunged the biggest toe straight into his mouth. The large toe was quite a mouthful and gave his tongue a workout as he lapped at the underside of her salty digit. Then he snuck her next toe into his mouth, filling it completely. The mouthful of toes wasn’t entertaining enough for the giant woman and she promptly extracted her foot. She patted his cheek briefly, admiring the size of her toes against his face.

“Mmm. Now stand up. I need a pic for the others to see.” She commanded.

Henry was happy to be done and quickly stood straight. Miss Pointe extended her legs fully, which easily cleared the desk, kicked off her remaining shoe and dug her heels deep into Henry’s little shoulders just beside his head.

“Say cheese!” She exclaimed while opening the screen to her cellphone. “Or maybe say footboy!” 

The empowered executive squeezed her feet together, pinching Henry’s much smaller head in between. Even with his neck included her feet soared the length of his head and then some, leaving her toes dancing overhead. He smiled for the camera in hopes it would all be over soon and Miss Pointe quickly angled the camera to capture the moment.

“Wow, you make my feet look HUGE.” She said, now looking through the pics she had snapped only seconds ago. “So, Henry, do you want the job?” 

Henry couldn’t say no, he needed the money. “Yes, I do. I really do.” 

“Mmm, that’s good to know. I have only one more ask of you.” She said, placing her feet back down under her desk. “But I need you over here,” she said, gesturing him to come closer.

Henry circled the desk until he was standing before the seated woman. Even so, she was still over a head taller than he was and she giggled at his diminutive presence. The towering woman placed a heavy hand on his shoulder and looked down at him. “Make me cum and the job is all yours.” 

Miss Pointe grabbed him by the throat, her fingers easily overlapping around his tiny neck, and ushered him to the ground. She forced him to his knees, and quickly used her giant hand to palm his little head like a toy crane at an arcade. With her free hand she slid her panties to the side, then gleefully thrust his pathetic little face deep between her legs. She planted each of her feet onto his lower legs, tucking her heels against the back of his knees and smiled. She could feel the tips of her toes extending past his little heels, making it apparent that her foot alone was bigger than his entire lower leg, making it rather easy to pin him in place. His head was swallowed in her grasp, which firmly cupped the back of his hair while his tongue semi-willingly slid deep into her lady parts. She was in complete ecstasy over her dominance.

“Mmm. Good boy, little Henry.”