A Beautiful Assistant

"Jack, I'm so sorry to have to leave but this is a terrific opportunity and you know I've always wanted to work for a television network," Erica said with a somewhat pained but hopeful look on her face.

"Of course it is, Erica," Jack replied. "I would never do anything to hold you back. You know that."

Jack was going to miss Erica for many reasons -- not the least of which was when she wore that low cut sleeveless shirt that she was wearing today -- but he knew that it was time for her to move on. Besides, there are a lot of low-cut shirt wearers in this city, he remembered.

"Well, I just want you to know that you've been the best boss I've ever had, Jack, and I mean it. You know that I'd do anything for you," Erica continued.

What exactly does she mean by that, Jack wondered? He had always fantasized about his assistant Erica and was sad to see her leave. She was a beautiful woman, only about 25 years old. He remembered back to when he first interviewed her when she was about to graduate from college. Her hair was still long and brown, slightly curly. She still had beautiful Italian skin and a killer body. She must be a 34 C or maybe even a D cup, he thought. He really couldn't tell, but figured that either way she was more than adequately endowed.

He never made a move as he knew that office flings were always a bad idea, but as he sat across his office and saw Erica's stiff nipples poking through her shirt coupled with her ample cleavage, he did some quick thinking.

"Well, of course we have to settle up your exit paperwork as soon as possible -- probably tonight. You know the office policy. Once you decide to leave, you have to leave. There are very few exceptions," Jack said, noticing the look of surprise on Erica's face.

"Jack! I was hoping for at least two weeks. I don't start at the network until the end of the month, the new job pays a little less than what I'm making now, and I can't afford to go without an income until the end of the month . . ." her voice sort of trailed off as she looked down at the floor. Jack could see her concern and felt a little guilty.

"Erica, I can try to see if there is something I can do to help but you know how hard it is to get anything out of this company. You're asking a lot here. I've always tried to be a good boss to you but this is --"

"Oh, Jack, I know! I know how good you've been but I really, really need your help here. Anything Jack, please!" A tear made its way down her cheek.

Jack's mind was working overtime on how to handle this and he was taken by surprise to feel his prick harden as Erica started to plead her case to him. He watched her full lips as she said 'please' the last time, and then looked back down at her chest. He had always noticed that Erica's nipples seemed to harden whenever she was emotional – happy, sad, amused, whatever. But now they looked like they might rip out of her shirt. They were just huge. He'd never seen her this upset before. His only question now was how to play this out. It was very late on a Friday night at the office and no one else was around. This is a good thing, Jack thought.

"Well, Erica, this is going to be really tough," Jack was worried that he might be overplaying this one but he knew that Erica lived paycheck to paycheck and out of her league for the salary she was making, especially considering that she lived in one of the most expensive cities in the world.

"OK, well, just name it. And I really mean ANYTHING, Jack," Erica said.

"Hm, well, I'm thinking that we should have a drink and make a toast to your new future, first. This is exciting -- going to the land of television," Jack said, looking her in the eye, and then back down to her chest.

Jack walked over to the closet in his office and pulled out a bottle and two glasses. He put both glasses on his desk and motioned for Erica to walk over. She walked over and grabbed one of the glasses that Jack had just poured.

"What do we have here?" Erica asked, looking at the clear liquid in the glass.

"The finest vodka in the world, Erica. Got it in Russia last year on that trip I took, and I've been saving it for an occasion that warranted drinking a $500 bottle of Vodka . . ." Jack smiled.

"$500!" Erica looked back into the glass as if trying to find the dollar signs.

"Sure, you remember the deal we brokered for that Norwegian oil contractor over there last year? Well, this was a thank you gift from them."

"Cool. I never drank anything that expensive!" Erica said.

"Well, as they say in Russia when you are toasting their favorite liquid, Za Zdrovia!" Jack lifted his glass.

"Za . . . yeah, whatever!" Erica clinked her glass on Jack's and drank down about half of it. "Wow, that's the smoothest vodka I've ever had!"

"That's why someone had to pay $500 for it, I guess," Jack said, sipping his again. "And to your new job," Jack said again holding up his glass. Erica clinked it again and finished the glass. Jack refilled it right away.

"You can really put this stuff away for a small girl," Jack said, laughing.

"Are you kidding? I can barely taste this. It's delicious. Can I make a toast?"

"Of course," Jack said.

"Well then here's to you, for being the best damn boss ever," she drank it without waiting to toast. Jack watched her and wondered if this was how she dealt with stress. He took another sip.

"Mmmm, Erica said. This is soooooooooo good!" Erica giggled. Obviously this stuff took affect pretty quickly, Jack thought. He never knew Erica to be much of a drinker, so he figured that she probably wasn't used to something of this caliber.

Jack leaned against his desk and watched Erica attempt to lean against it with him. She tried to put her hand on the desk but missed, and Jack quickly caught her arm breaking her fall, but spilling some of her drink on her shirt.

"Oh, damn, that's like $20 worth of vodka I just wasted!" Erica giggled again.

"Well, there's another way you're costing me. First you say you're leaving, then you want me to go to the bulldogs upstairs and get them to keep you on the payroll for a month, and now you spill my expensive booze all over the place!" Jack kidded.

Erica had a look of shock on her face, exaggerated due to her rapidly declining sobriety. "Oh, no, I didn't mean to cause any trouble, I'm so horrible!" Erica said.

"Well, you really owe me know," Jack said, his heart rate quickening again. "There is something you can do for me, Erica."

"Oh, you know I'll do it. What do you want?" Erica finished what was in her glass and tried to put it on the desk but missed and staggered a little. Jack caught her and the glass. "Well, first, why don't you stand there in the middle of the room."

As Erica stepped into the center of the room Jack pulled his digital camera out of his desk drawer and snapped a picture of Erica standing in front of his desk.

"Ooo, cool, I'm gonna be in pictures!" Erica squealed and giggled some more. Jack took a few more and she struck a couple of glamour poses as she laughed.

Jack took a breath. Go with it, he thought. "Right, now, I need you to take off your shirt Erica."

Erica paused, looked at him, and then pulled her shirt out of the waist of her skirt.

"Slowly," Jack said as he took a few more pictures of her as she did as she was told. "Great, now slowly lift it up over your head and take it off," Jack said, sounding like a Playboy photographer. His dick was hard as a rock and was getting harder as he watched her lift her shirt up revealing a white lacy bra. Jack could see that it was obviously a little too small for her as her tits were pouring out from the sides of the cups. He walked around her and took several more pictures. When he was standing behind her, he reached over her back bra strap and took out the tag.

"Well, I was right, a 34 C. But it looks like you could use a little more 'coverage' there, don't you think Erica?"

Erica turned around and giggled again. Jack looked at her breasts showing through the white lace. They were bigger than he had even expected, and her dark pink -- almost brown -- areolas were showing through. Her nipples were gigantic, and he couldn't wait to see them. He took a bunch of pictures – close up, farther away. He figured he could probably make a lot of money on them if Erica made it big in TV someday.

"OK, now slip out of that skirt, slowly again, please."

Erica again did as she was told. She stumbled a couple of times trying to step out of her skirt. She was wearing a bikini cut pair of white lace panties that matched her bra. More pictures from the front, the side, and from behind, where he marveled at her beautiful ass cheeks poking out from her panties. She wasn't wearing any nylons, which was just perfect with Jack as he hated them.

"OK, well, let's get down to business. Do you want to take off your bra or panties first?" Jack thought it only proper to let her decide which way to go first.

"Well, you've been staring at my tits for years now, so how would you like to see them live and in the flesh, eh Jackie?"

"Sounds great," Jack blushed slightly at being called out. But then again, who DIDN'T stare at this girl's tits? She certainly knew how to display them.

Erica reached around her back. Her breasts strained against the tight confines of her bra as she reached for the snaps. Jack took more pictures. As Erica unsnapped the bra her boobs jiggled around as if they were trying to break free on their own. She let the bra fall to the floor. Jack looked at those two perfect hooters sticking out from her chest and couldn't believe his eyes. They were incredible. Not sagging, and her areolas and nipples were even more amazing than he had imagined they would be. The areolas were slightly puffy, and the nipples were rock hard and very long – maybe an inch and a half. He'd never seen anything like them before and must have taken twenty pictures of them.

"Quite nice, huh," Erica said playfully. She grabbed them both and pushed them together to form the cleavage he was used to seeing. Then she grabbed her right nipple between her thumb and finger and pinched it slightly. Jack was harder than he'd ever been in his life, and couldn't believe the pictures he was taking of his assistant pinching and tugging on her own nipples.

"Oh my God, Erica. I had no idea . . ." Jack's voice trailed off. He wanted to reach out and grab them, but held off as he continued to take pictures. "Why don't you slip out of those panties now?"

Erica complied, and bent over as she slid them down over her hips and down her legs. Jack watched as her breasts jiggled and banged together as she wiggled out of her panties. He was stunned by the amount of movement they made with every slight move.

He looked and saw that she had a neat, close-cropped bush on top of her pussy mound. As she kicked her panties off from her foot, Jack looked at her beautifully shaped ass. It was always nice watching Erica walk from behind, and now he could better see why. Her butt wasn't fat, but it was a good size (the Italian blood, he figured, contributed to that) and it was also nice and jiggly, just like her tits. Jack was busily recording as many images as he could on his camera that fortunately held about 100 high-resolution images. He thought he must be getting close to the limit, but knew that he had another memory stick in the desk drawer.

Erica seemed to be extremely happy and having fun, so he decided to go farther.

"OK, Erica, now I need you to do a couple of things here. Just go ahead and do whatever I say and do it slowly so I can get some good shots," Jack sounded somewhat authoritarian about it and Erica just smiled and nodded her head.

"Great. First, have you ever sucked your own nipples?" Jack asked. Erica cupped her right breast, lifted it up to her face, and worked her nipple into her mouth. She licked it first, then grabbed it lightly with her front teeth pulling it gently. Then she took it into her mouth and started sucking on it. As she sucked the right one, she grabbed the left one with her free hand and rolled it around between her thumb and forefinger. After a few pictures, she switched and sucked on the left one. Jack noticed that the right one was wet and red which made him think that she had been sucking on it pretty hard. Rather than grabbing her right nipple while she sucked the left one, she reached down and started to rub her clit. She began moaning softly.

"Whoa, you're moving too fast," Jack said, trying to keep up with the action. She slowed her motions down but continued to stroke her clit and suck her left nipple.

"OK, now you can stop sucking and just go crazy on your pussy," Jack said. Erica immediately dropped her boob, laid down on her back on the floor of the office, and used both hands to work herself into a frenzy. Jack took a bunch of pictures from just about every angle and saw that his memory stick was full so he quickly changed it out and put the new one in.

"Great, keep going," Jack said as Erica worked her clit with one hand and stuck her fingers on the other hand inside her pussy. He stroked harder and harder until she went into convulsions and started screaming with delight. He hoped that the building was actually empty by now but figured that at 9:00 P.M. the only people around would be the janitors.

"Let's see how many fingers you can get up there," Jack suggested. Erica lifted her head up to watch as she started with two, then three, and then put four up there. Her tits were laying on top of her chest and wildly jiggling around every time she thrust her hand into her wet pussy.

"How about the whole hand?" Jack asked. Erica cupped her small hand in a fist and pushed hard against her pussy lips until she was able to work her hand in up to her wrist. She was moaning again like before and started to have another orgasm. Jack took several pictures of her hand up her pussy and then focused on her face. He found that he was even more turned on by watching her pleasure herself than he would ever have imagined, and she really seemed to be enjoying it.

After the orgasm subsided, Erica collapsed back on the floor, breathing heavily. Jack sat entranced watching her chest heave with every breath, and amazed at her stamina. He couldn't believe that her nipples were still as hard as they were when they began. He just watched as she caught her breath and thought out his next requests. What a beautiful woman Erica was, he thought, as he watched her recover.

Jack felt his rock hard dick through his pants and decided to unbutton and unzip them to give his large rod a little more room to move around. Erica looked over and saw that Jack's pants were open so she moved over and reached inside.

"Oh my God Jack," Erica said as she gripped his erect penis. "You're huge!"

"So are you," he said, looking at her tits.

"Why thank you, sir!" she giggled as she took his rod out of his pants and immediately started to suck on the giant head. Jack couldn't believe his eyes, and put his hand on Erica's shoulder as she worked his unit into her mouth. He looked down at her chest and reached with the other hand to grab one of her swinging tits. He was amazed at how soft, smooth, and warm it was, and how hard her nipple was poking against the palm of his hand. He reached down with his other hand and grabbed the other nipple, pinching it slightly and rolling it between his thumb and finger just as Erica was doing to it before. She started to moan again, this time a very muffled moan as she had Jack's massive cock stuffed into her mouth.

When he felt like he was going to cum into her mouth, he pulled his rod out of her mouth and told her to get on her hands and knees on the floor and turn around. She got down on all fours with her ass facing Jack. He looked down at her perfect ass and laid his rod down between her ass cheeks, then down between her legs against her still warm and wet pussy. She reached down and shoved Jack's prick into her cunt, and moved her hips up and down taking eventually taking in every inch of his rock hard monster.

Jack leaned down and watched her amazingly active tits sway back and forth with every thrust, and reached around to cup them as he shoved his cock as far as he could inside of her. Erica let out a loud groan and began her moaning again as he pounded it in.

Feeling like he was going to cum again, Jack looked down at her perfect ass and saw her tiny, tight asshole. He slowly pulled out of Erica's pussy and then pressed his cock's large head against the puckered flesh softly at first, then harder. This made Erica turn around with a surprised look on her face alerting Jack that this was probably a place that no man had gone before. Her expression was priceless so he quickly took a picture of her looking back at him as he pushed against the hole. This got Erica worked up again so that she started pushing back so much that her asshole quickly enveloped the head of Jack's dick. Then Jack slowly pushed the rest of his cock in until his balls were resting against her ass. Once fully in place, he gently worked his rod around inside of her and she reached up and started fingering her clit, which drove him wild.

As his cock was ready to spew, he pulled it out and Erica quickly got up on her knees and grabbed Jack's erupting dick, pointing it toward her face, taking a shot across her forehead, then her eyes and nose, then another couple of shots directly into her mouth. She then took the rest of his surprisingly large load onto her tits. Jack pulled his camera out and took several pictures of the cumshots from his unique vantage point, catching in midair the cum landing on her face and her tits.

Erica immediately started rubbing Jack's cock across her cum-covered breasts, and then rubbed the rest of the sperm in with her hands. She wiped the cum away from her eye and looked up at Jack for another 'money shot.' Then she rubbed the rest of the cum off of her face with Jack's cock, and licked his cock clean.

Jack couldn't believe it when he saw that he had burned through another 100 picture memory stick on his camera as he took the last couple shots of Erica laying on her back, breathless, with cum in her hair. He sat next to her, noticed that her nipples were finally relaxing, and gave her breasts one last massage before getting up and putting his package back into his pants. Erica got up and collected her clothes from around the office and slowly started putting them back on. She was still a bit tipsy from the vodka so Jack offered to give her a ride back to her apartment which she readily accepted.

After dropping her off, Jack went straight back to his place and crashed. As he laid down on his bed, he thought again about Erica's massive nipples and the amazing collection of porn he created before drifting off to sleep.