Jesse's Dream Job

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 s****r. 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 k** 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 f***e. 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 scr****g 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 k**napped 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.

“Excuse me gentlemen. It seems that the bean burrito I ate last night and I are at odds.”

They laughed, the conversation resumed and everything seemed fine. At an opportune time Ms. Angel slipped her hand under the desk and flicked Jesse’s ear so hard it brought tears to his eyes. He wouldn’t make that mistake again.

The meeting was drawing to a close so Ms. Angel pushed Jesse off of her penis and pointed for him to put her partially hard cock back into her panties and pull down her skirt. Jesse immediately understood and had her back in order in plenty of time. Ms. Angel pushed away from the desk and stepped out of view. Jesse could hear the three of them passing pleasantries and Ms. Angel telling them she was definitely interested and would be in touch. Finally the door shut and a few seconds later Ms. Angel’s long legs appeared outside of Jesse’s opening.

“Jesse, come out here.”

Oh shit! It sounded like he was in trouble. Leaning forward he crawled out of the leg well of the desk and stood up. Before she could speak he blurted out.

“I’m so sorry I made that noise and embarrassed you! I guess I’m fired already?”

Ms. Angel smiled and started to chuckle.

“No silly. I don’t fire people because they make a mistake, at least not as long as they learn from it. Can I assume that you’ve learned from your mistake?” Jesse rubbed his still smarting ear and nodded. “Good! By the way you did a nice job of understanding what I needed when the meeting was wrapping up. I have a lunch meeting and will be out of the office for the next couple of hours. Here is a list of things I need you to do and you need to work in your own lunch during this time as well. When I get back you will resume your duties under my desk.”

She handed him the list and began to gather her things to leave. Jesse looked at the hand written list which said:

Pick up dry cleaning
Scripts from Kinko’s
Drop off packages at UPS
See Rika when finished

“Ms. Angel, this isn’t a very long list. Do you have anything else I need to do?”

“Oh don’t worry. That list will keep you busy until I get back to the office. See Rika if you need any directions before you leave.”

With that his new boss turned and walked out of the office and Jesse couldn’t help but watch her go. She was so beautiful and so curvy and so…so feminine. No one would ever guess that she was packing such a serious hunk of meat in her panties. She was nothing like the drag queens he’d seen. She was a woman, pure and simple. At least that was the way it seemed to Jesse.

He gathered his wits and went out to see Rika about his errand list. She squared him away. Gave him the boxes to deliver to UPS, directions to the dry cleaners, (he knew where to find Kinko’s and UPS) and suggestions for a quick lunch. She also told him to hurry back because she had a job for him as well.

An hour later he was getting off the elevator with Ms. Angel’s dry cleaning. Rika directed him where to hang it in her office and told him to come back out to her. When he got back to the reception area he said,

“That wasn’t so bad. How long have you been working for Ms. Angel?”

“I’ve been with her three years now, working on my fourth.”

“You must like working for her.”

“Oh yes. We’re one happy f****y and as long as we try our best she takes good care of us.”

“How many people work here?”

“Well, there’s Kara who directs the movies, Selena who works with the scripts, Janice does all the set work and general maintenance around the office, Carla does cameras, lighting and editing, and me. So counting you and Ms. Angel, that makes seven. I’m really enjoying our little talk and all, but I still have that job I need you to help me with.”

“Oh! I’m sorry, I totally forgot. What do you need me to do?”

Rika stood up and this time there was no missing the bulge in her slacks. It was now curving down her thigh. Pretty far down her thigh. She stepped back and motioned him toward the leg well of her desk as she unzipped her pants.

“You mean I’m supposed to help you with your stress management as well as Ms. Angel?”

Rika grinned as she pulled her swelling prick out of her slacks. She was dressed so nicely in her cream pant suit that seeing her hard cock sticking out the front of her slacks was a very erotic sight. Jesse thought to himself, ‘What the hell. I’ve had Ms. Angel’s penis in my mouth all morning, might as well take care of Rika too.’ He looked under the desk and sure enough, it was set up just like Ms. Angel’s. Jesse crawled in side and had just settled into position when Rika’s long chocolate prick came sliding toward his face. Jesse opened his mouth and caught her on the fly, swallowing her to the back of his throat just shy of where his gag reflex would kick in. Above him Rika let out a heavy sigh of satisfaction and then went back to typing.

Jesse started to work her over. Running his tongue along the underside of her, sucking on the head and swallowing her deep as he worked to control his gag reflex, he gave her the best head he knew how with his limited experience. After ten minutes of hard work by Jesse’s mouth she was still typing normally, almost as if he wasn’t even doing anything to her. Jesse was starting to get tired, but he knew he couldn’t give up. He took her deep over and over, pushing his gag reflex to the limit until finally he got all of her cock into his mouth. For the first time she stopped typing. She slid a hand under the desk and onto his head, holding him so close he could feel her pubic hair tickling his nose through the opening of her slacks. He needed to breathe and pulled back, but she didn’t let him. He started to struggle, putting his hands on her inner thighs he tried to pull back even harder. Her other hand came under the desk and with both of them on his shaved head she pulled him hard against her and exploded into his throat. It took an extra ten seconds for her to finish squirting her sperm before she let go of his head. She let go so quickly that Jesse bumped his head on the desk. Coughing as he gasped for air he heard Rika saying,

“I’m so sorry Jesse! Please forgive me I’m so, so sorry!”

She rolled back from her desk, her dark skinned penis shining from Jesse’s spit and still standing up from her crotch. Leaning down she asked,

“Are you OK?”

Jesse coughed a couple of more times and wiped his eyes where the tears were streaming from the corners.

“Yea, I’m ok, but why the hell did you do that?”

“I don’t usually come at all when Ms. Angel’s PA is working with me, but you had me so deep in you that I kind of lost control. I really sorry, I should have warned you not to deep throat me. That’s the thing that really puts me over the edge!”

“Oh. Dually noted.”

“You better get in Ms. Angel’s office. She went in about three minutes ago.”

“Great. Now I’m late for the boss.”

Rika gave him a sheepish grin as she adjusted herself back into her pants. Jesse scurried into Ms. Angel’s office to find her leaning back in her leather chair, reading a script with her skirt pulled up and her impressive boner standing up from her crotch.

“Ms. Angel I’m sorry…”

She held up a finger stopping him in mid sentence. Jesse couldn’t help but stare at the penis that had already spent so much time in his mouth. As he watched it the head swelled and it seemed to get harder. He could even see it moving with her heartbeat. She turned a page, reading intently, concentrating on what was in the script. Jesse’s fascination with her engorged prick heightened as he saw a pearl sized drop of pre come develop on the tip. Unbelievably, he found himself wanting to take her in his mouth. Before today he’d never considered sucking a cock and now he was almost salivating over his boss’s throbbing erection. He licked his lips eagerly as she focused on the script.

“You want to take me in your mouth don’t you?” She said without looking up.

“Yes.” He whispered.

“Come over here and kneel between my legs.”

Jesse did as he was told. Once he was between her long legs he was close enough to smell the honey and lavender and see the veins pulsing along her impressive length. He reached for her prick to take it into his mouth, but without looking away from the script that had her so aroused she said,

“Ah, ah, ah, not yet. I want you to look at it and see what you’re missing. Think about how it is supposed to be in your mouth right now and not straining all alone in the cold open air. Your number one job is to take care of my needs. You are my personal assistant and I come first. No…matter…what. Now, I know that Rika didn’t tell you I’d come into the office so you won’t be held responsible for being late, but I want to take this opportunity to impress on you how important it is that you attend to me. In this one regard I’m very selfish. Do you understand?”

“Yes Ms. Angel.”

“Good! Now let’s get to work, I’m getting to the really good part.”

Jesse leaned in and covered her with his hot wet mouth. He couldn’t believe how much he was salivating. He was extra wet and slippery, which worked out very well indeed. He swallowed most of her on the first attempt and then sucked and pumped his face along her cock. He bobbed his head and worked his tongue along the underside as he caressed her balls. He got some of the copious saliva on a finger and began to massage her rectum as he sucked her. He didn’t dip his finger in, only rubbed around the rim. It seemed like the right thing to do. After a couple of more pages her hand came to the back of his head to encourage him to even greater heights. She was breathing hard as she gripped the back of his round shaved head like an NBA star palms a basketball and pushed him down hard to erupt into him. For the fourth time that day a woman’s come shot into his mouth and he swallowed every drop. Never before had Jesse even touched a penis other than his own and now he was drinking come from two beautiful women like he’d been doing it all of his life. This morning when he left to come to the interview he would have been appalled at the suggestion that he would be sucking a cock. But something about it being attached to a beautiful woman helped it to go down easier, just as Mary Poppins said sugar helped with medicine. Jesse sucked the remaining drips and drabs from Ms. Angel’s softening penis as she finished up the script.

There was a knock on the door and he heard it open. Rika’s voice said,

“I have that contract finished.”

“Thank you Rika. Please bring it in and toss it on the desk. I’ll see to it when I finish this script.”

Jesse heard the soft brush of paper sliding across the desk.

“Uh Ms. Angel?”

“Yes Rika?”

“Uh, please don’t be upset with Jesse about being late today. It was my fault.”

“Yes I know, and I’m not upset. But don’t let it happen again! By the way don’t you have a hot date with that photographer tonight? What’s his name again?”

“Yes Ms. Angel and his name is Rico. I’m very excited! He knows all about me so I don’t have to go through all that agonizing over when to tell him about my cock. It’s going to be so much fun without all that pressure!”

“Good for you Rika. There’s only an hour left before quitting time. Why don’t you go ahead and leave for the evening to get a jump start on primping for your date?”

“Oh Ms. Angel! That would be great! Thank you so much!”

“You’re welcome! Have a great time!”

Rika didn’t wait for another invitation to leave. She scooted out the door and pulled it closed behind her. Jesse was sucking on Ms. Angel’s now semi hard penis as she finished the script and set it on the desk. Looking down at Jesse she said,

“You’ve had a busy day for your first day. Maybe I should let you go early as well, but in your case it would be to get some new suits.”

Ms. Angel picked up the phone and hit a speed dial number.

“Hello? Antonio? It’s Ms. Angel.”

Jesse heard someone with an accent talking excitedly. Then Ms. Angel blushed and said,

“Antonio, if you keep talking like that to me I’m going to take you with me the next time I go to Italy!”

There was a response on the other end and Ms. Angel laughed and said,

“I don’t care how old you are! We’ll go back to your old haunts and make all your ex-wives jealous!”

Another response and more laughter from Ms. Angel made her cock twitch in Jesse’s mouth as he gently attended her.

“Antonio! Stop it! Come on now, down to business. I have a new Personal Assistant and his suits need an upgrade. They are classic J.C. Penny and he needs something with more flair. I’m going to send him over. Please fix him up and put the suits on my business account.”

Custom made suits. Wow. Jesse was in a daze. This day was something he’d only dreamed of and he had to admit that certain parts of this job were things he’d never dreamed of, but they were working out fine.

Ms. Angel and Antonio passed a few more pleasantries before she set the phone in its cradle and picked up the contract. While she read over the contract her cock twitched and moved in Jesse’s mouth. It began to grow and swell again, rising up to its full stature it was now ready for more. She placed the contract on the desk and motioned for Jesse to get up from between her long legs. Ms. Angel took a moment to admire Jesse. He was a big guy, nicely muscled and his shaved head made him appear intimidating. Something that could come in handy during the occasional tense negotiations that unfortunately still took place. She motioned for him to look over the contract.

Jesse picked up the sheet of paper and read it over. It was basically the same language as on the hand written contract he’d read that morning, only now it included his salary and had some time limits written into it and one little clause about orgasm management.

“Does that look satisfactory to you?”

“Yes Ms. Angel. It’s a far more generous offer than I could have imagined. Thank you.”

“You understand that this is a one year employment contract and that we will renegotiate for the next year just prior to expiration of this contract. If you terminate the contract before expiration you will have to pay back seventy five percent of the salary paid to you up to that point. If I terminate the contract you will only have to pay back half of your salary.”

“Yes Ms. Angel, I fully understand the contract except the part about orgasm management.”

“That’s actually rather simple. I expect for you to only have one orgasm per week.”

“Excuse me?”

“I was surfing the net one day and stumbled across a web site that catered to wife led relationships. On that site they talked about controlling the man’s orgasms to keep him in the mood to serve his wife. It sounded like a great idea so I tried it with my personal assistant. It worked wonderfully. Sometimes he was exceptional at his job, other times he would drag his feet and be moody. Once we began controlling his orgasms all that smoothed out and he was exceptional all the time. So it’s a tool I use to help you excel in your work.”

“How do I control myself?”

“To begin with you will not touch yourself while performing any of your duties. If while performing your duties you have an orgasm without touching yourself then we’ll have to adjust how often you get to have an orgasm. This is something that we will have to adjust as we go along for maximum performance. At the end my last assistant actually found it made his job very enjoyable.”

“I see. If you’ve had good success with that process in the past then I’ll do it too.”

“Then you are willing to sign the contract?”

“Yes, yes I am. Today has been a very eye opening day for me. I’ve done things that I never would have considered doing before and found them to be…”

“Bearable?” Ms. Angel said with a smirk.

“Actually, I was going to say pleasurable, but didn’t know of that was acceptable in a business situation.”

“Jesse, our business is pleasure. Hence the need for your unique position in the company, you will help us all stay focused. Just don’t be so good at your job that you become a distraction!”

“I’ll do my best to be good, but not too good!”

They shared a chuckle and Ms. Angel said,

“Let’s get that contract signed. Drop your pants and bend over the desk with the contract in front of you.” Jesse gave her a confused look so she explained. “I’m going to enter you from behind and give you a signing bonus. When I begin having my orgasm and squirting my approval inside of you I want you to sign the contract. I believe this will bind us even tighter than the contract and in the best way possible.”

Jesse did as he was told. When he was bent over the desk and in position Ms. Angel opened a drawer and applied a liberal splooge of lubrication to her swollen prick. She was very eager to seal this deal and get things around the office back on track. Ms. Angel placed the slippery tip of her cock against his sphincter and nudged it into the hole. She told him,

“Relax Jesse.” He tired and succeeded a little, but was still very nervous. She pushed and the tip began to stretch Jesse’s hole open. Jesse was breathing hard and she could feel him shaking under her hands. She had to admit, she loved this. There was something about sliding into a guy for the first time that was simply thrilling. Often they would shiver and shake as she fed her big penis into them. Taking her for the first time was always a challenge for a man who’d never done this before and she could tell that Jesse was her type of virgin. She rubbed his back with her hands as she tried to soothe him and help him relax, the tip of her cock slid deeper and only the rim of the head was visible. Jesse let out a big sigh and she felt his sphincter ease up ever so slightly so she took advantage of it and popped the head inside him. He gasped and as she expected clamped down hard on her throbbing member. She loved how he gripped her with his ass. It took about thirty seconds before he relaxed again and she stood there during that time and watched his sphincter twitch and quiver around the head of her cock. She was enjoying every second of this to the fullest.

“It’s time to take the rest of me Jesse.” She said softly as she tightened up her ass cheeks and began to feed her rock hard shaft into him. She found watching her cock disappear into his ass to be very stimulating. She was so slippery he couldn’t have kept her out if he tried, but she still went nice and slow. Savoring inch after inch of her penetration into him until finally her hips pressed into his ass cheeks.

“There now, nice and full. You have a very entertaining sphincter. It’s so tight that this isn’t going to take very long. I could almost come right now.” With a strained voice Jesse replied,

“I’m glad you like it Ms. Angel.”

“Oh I like it a lot! Are you starting to get used to me? Am I still hurting you and stretching you out too much?”

“It hurts a little, but I’m adjusting to how big you are.”

She leaned up over his back and whispered in his ear.

“You know just the right thing to say to a woman that has her cock buried in your ass, don’t you.”

As she said this she pushed against him rolled her hips forward to press that extra inch of her eager cock into him. He let out a little gasp and replied,

“I do aim to please Ms. Angel!”

She rocked her hips back and forth as she short stroked him. Staying deep inside him she relished how he gripped and quivered around her swollen cock. She ground herself into him. She pulled him up off of the desk and pressed her breasts against his back. Never missing a beat Jesse reached back and gripped her ass in one of his big strong hands. He rubbed and caressed it as she slid back and forth inside him. This one small move pushed Ms. Angel up to the edge. He was showing that he was eager to please her and that turned her on immensely.

“I’m getting close, it’s time for you to sign the contract.”

Jesse leaned back over the desk and Ms. Angel held onto his hips. He picked up the pen and got ready to sign as her tempo increased with her breathing.

“I want you to come to work with me Jesse. I want you to be my personal assistant and work very closely with me each and every day. Jesse sign the contract because I’m coming inside you right now to confirm you as my choice! Oh…OH…OOOOH! OH…HELL YEA!”

Ms. Angel squeezed Jesse’s hips and pushed her exploding penis as deeply in him as possible. With each shot from the tip of her girl gun he could feel it flexing and moving inside him and he thought he could even feel each of her squirts as he shakily scrawled his John Hancock on the dotted line. They were sealed together now. Her creamy come was spreading deep inside him and his signature was drying on her contract.

After a few seconds she withdrew from him and took some paper towels out of one of her desk drawers to wipe up all of the lubrication. Jesse’s head was spinning as he came to grips with what had just happened. He was hers for the next year. Not just hers, but Rika’s also. She handed him a paper towel and said,

“You might want to clean up before you go to see Antonio.” She put her deflating penis away in her panties and straightened her skirt. As he wiped up she went on to say, “I need you to be here at 7 am tomorrow. We are going to have a quick staff meeting so everyone can meet you and get to know you. I feel that is important since you will be working as closely with them as you are me, at least when I’m not in the office.”

“You mean that all of the other women are…like you and Rika?”

Ms. Angel looked at him and smiled as she said,

“Of course. After all, I promote women like us so it only seems fitting that all I hire are women like me. You would be the only exception to that rule for the obvious reason.”

The full realization of just what his job was hit Jesse like a Mack truck. Ms. Angel could see the realization in his eyes and she put her hand on his arm as she said with a chuckle,

“Don’t worry. I’m sure you’ll do fine. Some of the women only take advantage of my assistant once a week or so, that is unless we’re heavily into the production of a movie.”

Jesse pulled up his pants as he thought about what he signed on to do for this company. He turned back to the desk and looked at the contract. More specifically the salary on the contract. Yep, he could do it for one year. Ms. Angel continued preparing him for the next day’s duties.

“After the staff meeting you will spend the rest of the morning with me. After lunch you will report to Rika until our newest prospect comes in for her screen test. She is 21 and brand new to the adult movie scene. I will need you to schmooze her and cater to her every need, no matter if it is getting her a soda or…well you know. I understand that she is a very horny young lady so please be on your best behavior, oh and Kara may need you to help out with the screen test as well. After the screen test you and I have a fund raiser we will be attending.”

“Ms. Angel, may I ask a question?”

“Why of course Jesse!”

“What happened to your last assistant?”

Ms. Angel smiled and shook her head. With a chuckle she said,

“He did an excellent job of managing his money and retired after only five years. And to top it all off he took my best and ‘biggest’ actress with him. They are somewhere in the Cayman Islands last I heard, on his sailing yacht, and if I know those two she is buried up to her balls in him right this second.” She glanced at her watch and said, “I need to get going. Turn off the lights on your way out and I’ll see you at 7 tomorrow.”

Ms. Angel picked up her purse and attaché case. Jesse watched as his strikingly beautiful and well hung new boss swayed out the door. This is going to be one hellva year he thought as he turned off the lights and followed her out.

End



NOTE:
THIS FANTASY OF MINE I SHARE WITH IS ALL THANKS TO AN EXSTREMLY TALENTED AUTHOR KNOW AS RUWILD WHO WAS KIND ENOUGH TO TAKE MY IDEA AND MAKE IT INTO AN AMAZING STORY!!!





97% (38/1)
 
Categories: Shemales
Posted by SCARFACE12
3 years ago    Views: 1,426
Comments (9)
Reply for:
Reply text
Please login or register to post comments.
2 years ago
Hmmm my manager is female...I think?
..you never know!

Great story!
candi0058
retired
3 years ago
wow i want a job like that you need to make the next chapter going through the adventures of Jesse and Ms. Angel would make a great book by the way i came in my panties twice and that was just reading this story
thanks
Candi
3 years ago
Best ever,would love to have Jesses job
3 years ago
great story
3 years ago
good story
3 years ago
nice stoy is der een 2nt part
3 years ago
awesome story
3 years ago
VEry well written story!
3 years ago
Great story ;-)