Jesse's Dream Job

byruwild©

Jesse sat nervously in the waiting room of the opulent office. He was there for a job interview as a personal assistant. Now at six foot tall with 220 lbs of football hardened muscle he did not fit the description of a personal assistant, but the advertisement on line had been pretty specific about the qualifications for the position and they were looking for a guy with his build. It was even listed first in the qualifications and typing was considered a 'bonus' ability. Go figure.

When he had arrived the receptionist called his potential employer on the phone and told him that Ms. Angel would be with him in a few moments. While those moments dragged on Jesse had time to consider how badly he needed this job. The rent was past due, the final notice for the phone bill was lying on the table and the refrigerator was woefully empty. If he could just land this job things would finally turn around.

"Ms. Angel will see you now." The receptionist said with a big smile.

"Oh. Thank you." Jesse said with a nervous smile.

They stood together and she opened the dark mahogany office door. Her milk-chocolate skin created an interesting visual bridge between her cream colored pant suit and the rich dark red of the wood door. She had high cheek bones, close cut dark hair and a brilliant smile. The name tag on her jacket lapel read Rika and she looked like she could be Haley Berry's little sister. But most of this was lost on Jesse because he was so nervous. He even failed to notice the proudly displayed bulge in the front of her suit pants as he passed her and stepped into an office that personified soft power.

The floor was covered in a deep cream colored carpet that contrasted with all of the dark mahogany wood work. Small bright halogen lights glinted off metal accents of brushed pewter, expensive yet understated, and both outside walls of the corner office were made of glass. The view was breathtaking. Sitting diagonally in the corner where the two walls of windows met was a massive wooden desk. Behind the desk, with her back to the view, was a strikingly beautiful blonde woman. Her head was down and she was writing as Jesse approached the desk.

"Please take a seat. I'll be right with you."

Her voice was smooth and confident with a smokiness that would have been comfortable on late night radio. Jesse tried not to stare as he settled into one of the two seats across from her desk. He attempted to look out the window, but her commanding presence kept drawing his eyes back to her. The room was so quiet that he could hear the pen moving across the paper. She was wearing a dark pinstripe suit jacket over a white business shirt that was unbuttoned just enough to reveal some modest cleavage and a gold cross lay against her smooth tanned skin. The suit was expensive. You could tell by the way it was made. All of the lines were precise and the corners sharp. The cloth had the sheen of suits you see in stores where there are no price tags. If you have to ask, you can't afford them.

"Do you like what you see?" Startled out of his observations and feeling guilty to be caught ogling his prospective boss. (How had she known he was looking at her?) He nervously asked,

"Excuse me?"

"Do you like what you see? Most people are very pleased with the view and comment on it. You only seem to sit there and stare at me."

"The view? Well, I...uh...yes. It is very impressive. But not as impressive as you." Mentally he slapped himself as he tried to figure out where the hell that had come from and began to back pedal. "I uh mean, well it's..."

She looked up from her writing and what he saw in her blue eyes stopped his lame attempt to explain in his throat. It was like looking at a tigress. A very hungry tigress. He swallowed and was prepared to be ordered out of the office. She glared at him a moment longer then broke into a smile that lit up the room.

"Sucking up are we?"

"No Ms. Angel." He said with a sigh. "I apologize if I have offended you. I'm very nervous and sometimes my filter doesn't work well when I'm nervous."

"Please don't apologize for complementing me. It's nice when a young man tells me he thinks I'm attractive...or at least impressive."

Jesse let out a huge mental sigh of relief. At least it didn't look like he was going to get kicked out before he got to complete the interview.

"So tell me Mr...."

"Just Jesse please Ms. Angel"

"OK. Jesse, please tell me how much you know about my company."

"I Googled the name TransArt but I'm afraid all that came up was a movie company. From your on line job posting I couldn't tell if that was your company or not."

"Did you read up on the company that did come up on the internet?"

"Yes. They make movies that involve Transgendered subjects."

"Well that is my company. We make movies both for education and entertainment."

"Oh. I guess that I should have read more."

Ms. Angel laughed and asked,

"Why? Would knowing what we do have kept you from interviewing with me?"

"No, but it would be nice to have been better informed."

"I see. Tell me Jesse, are you open minded? Can you step outside of the stereo types imposed by society if it means a good job at an obscene wage?"

"I'm fairly open minded and stereo types don't concern me, but I'm not sure I know what an obscene wage is."

Ms. Angel circled something on the page she'd been writing on, turned it around and pushed it across her desk to Jesse. When he looked down at the page what was circled was a very large number with six figures in it and no decimals. Wow.

"Oh! That's what an obscene wage is!" He took a moment to read the page which said,

I the undersigned agree to be on call as needed up to 24/7 and willing to perform any and all functions and tasks as requested of me by Ms. Angel or other persons in the employ of TransArt for the duration of the next year. In compensation for these duties the undersigned will receive full medical insurance including a required physical each month, a 401K retirement plan that is vested after one year and the salary indicated at the bottom of this page. Bonuses will be paid on the percentage of profitability of the company each quarter. At no time is the undersigned allowed to disclose the nature of this offer.

"Are you offering me the job?"

"Not just yet. I'm offering you the opportunity to try out for the job. If you want to try out for the job then all you need to do is agree the you would be willing to sign a contract such as the one outlined before you. If at the end of the day I decide to hire you it will be typed up into a more presentable contract that we will both sign. Are you interested in trying out for the job?"

Jesse looked at the figure at the bottom of the page. That was more money than he could have made in five years at his old job. But the job 'description' was still pretty vague.

"Ms. Angel I'm very flattered that you are willing to let me try out for the job, but I've never been a personal assistant before and to be truthful I'm not sure I can do it."

Ms. Angel lit up the room with another one of her smiles. She stood up and walked around to the front of her desk and partially sat on the edge. Her long legs protruded from under a snug skirt that matched her jacket. The skirt came to a stop a few inches above her knees and her feet were clad in a pair of red soled black pumps. Jesse couldn't help but look at her incredible legs and feel a stirring in his undershorts. Ms. Angel's blue eyes twinkled along with her smile as she said,

"Honesty. I appreciate that in an employee and I would want them to expect no less from me. Let me take a moment to lay out your typical job duties as well as other possible duties that may be asked of you."

She took a moment to smooth her skirt and collect her thoughts. This was the delicate part of hiring a personal assistant. Jesse had promise and she didn't want to scare him away.

"Here at TransArt we make movies. We make very erotic, pornographic, movies about Transsexuals, T-Girls or as most of the media refer to them Shemales. Our niche is that we deal with any situation where the t-girl is dominant. I have a good eye for what the submissive person likes in a dominant t-girl and I've been very successful in putting that idea into video form and marketing it over the internet. So at any time during the day there are a multitude of sexually charged situations going on around this office and our studios. This creates a lot of sexual tension, which has proven to be counterproductive to our daily operations.

This is where you come in. I need a personal assistant that can do the usual things a PA does, such as run errands, organize meeting material, help keep me on schedule and prepared for those meetings and get me my tea. Those types of PA are everywhere. My PA has to be willing to go above and beyond all of those regular duties by attending to my sexual needs."

She waited for a moment to allow what she'd told him so far to sink in.

"So you'd be paying me to have sex with you?"

Ms. Angel smiled and leaned forward allowing Jesse a nice long look down the front of her shirt. She knew he would look, after all they always did, and he would see her tanned breasts cupped in a lacy white bra. Jesse did look and as he did she touched his arm and said,

"Don't misunderstand me. This is not sex in the passionate sense; so much as it is service. The same as if you were cutting my hair or giving me a massage as I write reports and answer phone calls. We would be working together and you would be under my desk taking care of me and helping me with stress management issues."

"Under your desk?"

Jesse wasn't sure he'd heard her correctly. After all he was sort of transfixed by the view down her shirt. Ms. Angel stood up and motioned for him to follow her around to the back of the desk. She rolled her leather chair out of the way and when he looked under the desk he could see that the area had been developed into a comfortable work area. There was a small saddle seat similar to a bicycle seat, but more comfortable looking with a padded area on either side down into the floor for someone's legs to rest. There was also a small refrigerator for drinks and a couple of shelves built into the desk. While Jesse was assessing this potential work area Ms. Angel made as if to tuck in her shirt and quickly slid her hand down and popped her cock out of her panties. Just in case.

"Why don't you see how well you fit? After all if you can't fit in the area there is no reason for continuing this interview."

Jesse returned his attention to the striking woman that was standing before him. She looked like she could have stepped out of a high end clothing catalogue. She motioned for him to crawl under the desk and with a final thought about the dollar figure at the bottom of the page she'd shown him moments ago he turned and did just that. Jesse felt like he was little kid again hiding under the teacher's desk all those years ago in elementary school in hopes to see up her dress. Once under the desk he settled onto the seat pushed his legs into the holes provided. There was plenty of room once he was in place and he had to admit that his face was in the exact location needed for 'stress management'. All in all it was very comfortable.

"What do you think? Could you spend several hours at a time in there?"

"Yes, I think I could. It's much more comfortable than it looks."

"Let's see how things are for you with me in my seat."

She didn't wait for his reply as she sat in her chair and rolled into position. Spreading her legs as they neared Jesse she ended up with a thigh on either side of his shoulders. Her thighs were long and smooth beneath the stockings and as she rolled into position Jesse got a hard on. Ms. Angel reached under the desk and pulled her skirt up which allowed Jesse to see her cock for the first time. It was swollen and hard. Twitching with her heartbeat, it was eager to plumb the depths of his mouth. Jesse jerked back and hit his head with a thump on the desk. Pushing forward Ms. Angel grabbed his head and pulled his face close to her throbbing penis. Jesse was a big boy and she knew that she wouldn't get her cock in his mouth by sheer force. It would take some erosion of his will first.

"Jesse, think about that figure on the bottom of the page. Think about all of your money worries going away by simply opening your mouth and letting your inhibitions fade away."

Jesse's struggles slowed as he listened to her words.

"Just open your mouth and step into a world were a special kind of professionalism is handsomely rewarded. Try it and if you find it so repulsive that you cannot bear it we can end the interview."

Ms. Angel could feel his heavy breath washing over her engorged cock and the anticipation was excruciatingly delicious. Jesse could smell her. She smelled of lavender and honey. A similar scent to what a very special ex-girlfriend had smelled like some years ago. It was an odor that made him think back to all of the fun times they'd shared between the sheets. It was a smell of sex and arousal.

Ms. Angel was still pulling on Jesse's head and keeping a steady pressure on him. His neck muscles were getting tired and his will was weakening. Pursing his lips he allowed her to pull him forward and he kissed the head of her penis. It was soft and warm with a touch of pre-come on the tip. Above the desk he heard Ms. Angel give a little MMMM of pleasure as she pulled even harder on his head. Eagerly pushing the tip into his full soft lips until it bumped his teeth.

Jesse's neck was getting tired and his wallet was empty. He was tired of barely scraping by and knew in his heart that he needed this job. Jesse opened his mouth.

Ms. Angel felt the wall of teeth part and wasted no time filling the opening. She pulled Jesse onto her aching prick till she felt him gag. Only then did she let up a little. Jesse hadn't been prepared for such enthusiasm from her and his eyes were watering from gagging. Now that she was in his mouth he realized that she was much larger than he'd anticipated. His jaws were stretched as wide as they would go and she wasted no time getting down to business. Holding onto his shaved head she pumped him up and down over her throbbing cock and it didn't take long for Jesse to realize that at least for this orgasm he was just along for the ride. Ms. Angel was pumping his mouth with complete abandon and fully focused on having an orgasm. Jesse was reeling from her fucking his mouth. His nose was running and he was drooling like a dog with a bone, but instead of a bone he had a boner in his mouth. He gave himself over to her and let her do as she wanted. Time swirled and he had no idea how long she'd been using him when suddenly she held him tight and he felt her thick cock begin to pulse. Shot after shot of hot come squirted against the back of his throat. He coughed and swallowed reflexively with each shot as he tried to steady himself by holding onto her thighs. Just when he thought she was never going to stop coming she relaxed her grip and leaned back in her chair to look at his face.

Ms. Angel let out a long sigh of satisfaction and said to him,

"You look very nice with my cock in your mouth Jesse and that's a view I want to see more of, so I'm offering you the job. You're by far the best feeling guy I've interviewed and even though you were reluctant you still stepped up to the plate by allowing me to do what I needed to do."

Jesse looked up at the beautiful blue eyed blonde that was dressed so smartly and wondered for a second what his buddies would think if they knew that he was under her desk and between her legs with her big cock in his mouth. All his life he'd been a pretty big guy, so the thought of submitting to any woman, let alone one with a big penis, had never crossed his mind. He had to admit, he liked it. He wanted to be her personal assistant and fulfill her every wish.

"Well what do say Jesse? Will you come to work for me and be my personal assistant?"

He started to pull off of her penis, but she caught him with a hand and pulled him back onto her.

"You don't have to speak. Just nod your head and I'll have the contract written up and we can sign it at the end of work today."

Jesse nodded his head and Ms. Angel broke into a big grin.

"I just knew that you'd join our little group and I'm so happy that you have! The other women will be thrilled to have you on the job. Now things can finally get back to normal around here! No more grumpy T-Girls!"

Ms. Angel looked at the clock on her desk and said,

"Oh my! I've got a meeting in a few minutes with two gentlemen that want to pitch a new story line to me. You stay under there and keep me in your mouth, but don't make any noise."

Ms. Angel was obviously very pleased as she sat up at her desk just as the phone rang. With her large penis still lodged in Jesse's mouth she picked up the phone and began to talk. To Jesse there was something very electrifying about having her cock in his mouth as she talked on the phone.

"Yes Rika? That's fine, I'm ready for them so you can send them in. Oh and please get the employment contract for Jesse ready. Yes, he's joining our team today. I'm very excited too Rika!" Ms. Angel said with a laugh. "Why yes he is, but that is not why I hired him. No, the reason is because I believe that he has the potential to be a top performer. Rika! You're incorrigible! Please send in the gentlemen."

Jesse couldn't help it and smiled around her cock. She could feel him smile and playfully reached under the desk and slapped him on the side of the head as she mumbled.

"Now don't get the big head. You've still got a lot to learn."

The door opened and Jesse heard Rika announce.

"Mr. Goodman and Mr. Shorenstein."

"Thank you Rika. It's nice to meet you gentlemen. Please have a seat and let's get right down to business."

Jesse heard something that sounded like what he thought people sitting in chairs should sound like.

"Very well Ms. Angel. We think we've come up with a story line that would work well with your special touch. You seem to be able to make even mundane situations become very erotic."

The second man said,

"Yes we are big fans of your movies!"

The first guy cleared his throat and continued.

"As I was saying, our story is about a rodeo where your girls ride unwilling males that have been kidnapped off of the street. The men are all bad men that have been chosen specifically for their aversion to being 'ridden' and their need for punishment...."

Jesse kind of lost interest at that point, because Ms. Angel's penis began to stir. As she listened to the plot line and how the camera angle would show maximum penetration, she began to grow larger in his mouth. He took a bit too long to get started for Ms. Angel who slid her hand under the desk and pulled him down onto her growing member until he gagged again. Instinctively he pulled back and she answered by pulling him down again. That was when the ah-ha moment struck.

She finished hardening in his mouth and he began to suck on her with gusto as he pumped his face along her generous length. He was getting into it and she spread her legs to allow him full access to her turgid member. Jesse could hear the men talking and Ms. Angel giving non committal uh-hums and the like. He was paying more attention this time and when he was pretty sure she was getting close to an orgasm he doubled his efforts. He sucked harder and worked his tongue around the head, then took her as deep into his mouth as he could. He could feel her legs shaking as she neared her second explosion of the morning. Once again without warning she exploded in his mouth, but he was better prepared this time and easily swallowed everything she pumped into him. Jesse was turned on now and he was getting into giving this incredible woman head so much that he accidentally made a loud slurping noise. The room went silent.

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byruwild© 18 comments/ 106826 views/ 70 favorites

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