Jesse's Dream Job

"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 family 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.