Femboy Executive Assistant

Jackie was sitting in the lobby waiting for his name to be called for his interview. He found the position online looking for an Executive Assistant for the owner of a marketing agency in his hometown. Being 22 and just graduating college did make him a bit nervous for his first real interview, but he was excited to start working.

Jackie showed up to the interview in different attire than most men as he dressed strictly feminine. He had very feminine features and was smooth all across his body with the only hair being that on his head, eyebrows and lashes.

He was currently wearing a skirt and a dress shirt tucked into the skirt. The skirt was a few inches above the knee to maintain a professional look but also show off the slightest amount of leg.

As he was holding his folder with his resume and proof of education, he heard his name being called.

"Jackie Bingal please head in for your interview with Tom McMillin."

Jackie stood up and went in through the double doors leading to Tom's office.

"Welcome Jackie, feel free to have a seat and we can get started on your interview for the position."

Tom was wearing a dress shirt and a pair of slacks as he sat at his desk and waited for Jackie to sit. Tom was 50 years old and stood about 6'1. He was a solid man with broad shoulders and a decently built frame. He wasn't ripped but he definitely kept in shape.

Jackie took a seat and handed Tom his folder full of his information and Tom took it accordingly before taking a look at his resume first.

"Well looks like you've done some other assistant jobs here and there while you were in school. Even though you don't have much experience, this resume is very well put together."

"Thank you sir. I just graduated with my Bachelor's so I wasn't able to get a whole lot of experience while in school but I did what I could to get some experience."

Tom continued to glance at the documents before him before looking Jackie in the eyes.

"Well I think you'd be a great fit but I do want to ask a question. On your application you stated you were a male but the way you are dressed is very feminine. I don't have a problem with it, I was just curious because you look more female than male at the moment."

Jackie chuckled nervously before deciding to just come out and explain it. "Well you see, I'm what some people call a femboy. I very much so identify as a male but I just prefer to dress feminine and I also happen to have a very feminine appearance as well. I am still male and like to be referred to as a male but I do primarily dress in feminine clothes."

"Interesting. Well it's not a problem to me. I definitely don't mind having nice people to look at so consider yourself passing the first portion of the interview. The rest of the other interviewees did not pass this portion so you are the first. I do have one other after you though but I'm pretty sure you are the best fit."

Tom leaned back in his chair as he eyed Jackie up and down and Jackie smiled as he was excited to pass the first portion of the interview.

"That's great to hear! I'm excited to start the second portion and prove why I'm the best candidate for the position!"

Tom chuckled as he readjusted himself in his chair. "That's great. Now tell me a little bit about what you know about Executive Assistants and the role they serve."

Jackie thought for a second and remembered what the job offering stated as well as a couple of other friends that he had that had the role for other companies.

"Well I believe the role basically means that I assist you in pretty much anything. That being running errands, screening phone calls, printing things out for you. I also know of one of my friends who picks up her boss's kids from school on certain days of the week."

"Well you pretty much got the gist of it. You will be assisting me with everything I need. Filing papers, screening calls, running errands, and other things in between. I don't have kids so you don't have to worry about picking mine up but I do have other things that I would require you to help me with that I need to know you are ok with."

Jackie smiled as she got the answer right and felt very confident. "Of course. Just let me know what it is and I can do it!"

Tom chuckled again as he smirked at Jackie. "That's good to hear. See I have needs that need to be satisfied. To be honest with you Jackie, I assumed you were a femboy right off the bat. I actually have another femboy who lives with me and satisfies me when I'm at home but I'm a pretty insatiable man and not being able to get release at work is really taking its toll."

Jackie's smile faded as he started putting two and two together.

"To get straight to the point, one of your most important roles as my Executive Assistant would be to make sure my dick stays drained and satisfied. I do want to reassure you that I will make it very much worthwhile for you. The pay is very good for an entry level Executive Assistant and I am very generous with letters of recommendations and I have a lot of connections if you were to want to pursue something else."

Jackie sat there pondering what he just heard. On one hand, he really wasn't expecting his first professional job to be servicing his boss's cock. On the other hand, Jackie was a bit of a slut so the thought didn't entirely bother him. That and the opportunity to be able to be in touch with Tom's connections on top of the very generous salary, it was almost too good to pass up.

"Just to clarify, I won't have to worry about satisfying you once I'm off the clock? Seeing as how you have someone at home for that, you'll only need me at work?"

"That's correct. Some Executive Assistants are on the clock 24/7, but with this position, you'd be here 9-5. I'm also very flexible and understanding. If I'm not here or don't need you, you can go home early once you have your other duties finished and you will still get paid per usual."

Jackie contemplated shortly before deciding it's something he wanted to do. "I'll do it."

Tom smirked before standing up and unbuttoning his pants and sliding them down to his ankles along with his boxers before sitting back in his chair.

"Excellent, why don't we run a trial period right now seeing as how I still have one other interview coming in after you. I want you to service my balls while I do this final interview. If you do a good job, I'll send them on their way and you will have the job."

Jackie was taken aback at having to satisfy him while other people were in the room but decided that this must be the final portion of the interview. Jackie stood up and straightened his skirt before moving to Tom's side of the desk and crawling under the desk.

Tom scooted his chair forward to keep Jackie hidden from sight and Jackie came face to face with Tom's balls.

The first thing Jackie noticed was the smell. Jackie had been face to face with some pretty musky balls before but Tom's were powerful. Powerful men must emit a powerful smell Jackie thought to himself.

Jackie scooted forward a bit and nuzzled his face into his massive balls and took a whiff before planting kisses all over them. Jackie then noticed just how big Tom's balls were and how large his cock was as well.

The balls were easily each the size of a baseball, maybe even a bit bigger. Jackie also noticed just how large Tom's cock was as it lay across his forehead and the top of his head. The cock didn't seem fully erect or even close to it and it had to be seven or eight inches without being hard.

Jackie was brought back to the task at hand when he heard Tom call for the next interviewee.

"Lisa, go ahead and send in the next interviewee in."

Jackie quickly started licking and sucking quietly on Tom's nuts as he set Jackie's paper's to the side. Jackie was worried that the interviewee would notice or hear him so he quietly sniffed the musky balls in front of him as he traced his tongue up and down the salty, wrinkled skin.

Tom sat still as his balls were getting quietly worshiped by the sexy femboy under his desk. His dick started to harden as he felt Jackie's tongue lap at his large cum factories and twitched slightly when Jackie popped one of his balls into his mouth.

Tom didn't give any sign that there was a cute femboy slobbering all of his fat nuts while he administered the interview. Jackie stayed quiet as well licking and sucking while he listened to Tom give the interview until he heard Tom finish and let the interviewee know that he'd be in touch.

Tom waited until the door to his office closed and he slid his chair back slowly to look down at the boy under his desk. Jackie looked up at Tom with his cheeks red, blushing from being down and working on his balls for so long.

"I think it's safe to say you got the job. My balls felt quite good during that interview. It was quite distracting how well you were doing. I'll let HR know that I chose you and you should get an offer letter sent to you by the end of the day. I want you to start Monday. That gives you a full weekend to get yourself prepared to be my assistant for the foreseeable future."

Jackie nodded and stood up as Tom also stood and pulled his pants up. Jackie was a little perplexed that Tom didn't have him finish him off but figured he'd get the chance at some point.

Tom and Jackie straightened themselves up before Tom led Jackie to the door and walked him out. "Have a safe trip home and looking forward to seeing you on Monday." Tom said with a wink as he playfully smacked Jackie's plump ass.

Jackie smiled as he exited the building realizing he just earned himself a pretty nice first job and all he really had to do was use his sexuality to keep it, something that he had no problem doing at all.

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Tom was sitting on his couch with a beer in one hand and one hand with the remote to the TV. Between his legs was a platinum blonde haired femboy bobbing up and down Tom's lengthy shaft slurping and sucking the whole length.

"I met my new assistant today. A cutie just like you slut. I had him sucking and licking all over my fat nuts to earn his position and he definitely didn't disappoint. I know how much you love my loads so I made sure to not let him finish me off. You are my number one slut after all and that comes with some perks."

The boy giggled as he continued sucking Tom's cock swallowing his entire cock and wrapping his lips around the base, sticking his tongue out to lick Tom's balls while throating his cock.

"That's right, work for that nut slut. Daddy's got a fat load backed up and you are gonna work it all out for me like a good cock sucker." Tom set the remote down and used one hand to grab a fistful of the boy's hair and began forcing him up and down his thick shaft fast and hard, enjoying the sounds of the boy gagging and retching all while feeling his throat spasming around his hard cock.

"Here's your reward slut, drink up." Tom pushed the boy all the way down the base of his cock and held him there feeling his cock start to erupt straight down the boy's throat. Tom loved cumming balls deep in a throat because he could feel the throat milk his cock every time the boy tried to swallow.

Tom held the boy down for a little while before letting go of his head. The boy slowly slid up the length of Tom's cock slick with saliva. The boy nursed on Tom's tip as he swallowed the remainder of the jizz that pooled out of Tom's cock.

"That was a good first load, my balls are nowhere near drained though."

The boy chuckled and lowered himself to Tom's large balls and began to worship them as he knew he was in for a long night of fun.