Katie's New JobbyBigMeanie©
It was just another Friday. Katie sat at the desk near the front door of the gallery, IMing with a "Master wannabe." Bored, she played along with his demands to play with her clit. A little self-pleasure was better than sitting and doing nothing. After a few minutes, Katie looked up and noticed someone heading towards the front door.
"Customer. Gotta go," she typed with one hand as she pulled the other out of her knickers.
With a courteous smile, Katie greeted the striking, very tanned blonde as she entered the gallery. "Good morning! Welcome to the gallery. How may I help you?"
"Good morning. I'm Cynthia, the new owner. Are you the only employee here?"
"Very good to meet you, Cynthia. I'm Katie, and yes, I'm the only one here."
"Any customers here, Katie?"
"No, afraid not. It's been a very slow day."
"In that case, please lock the door and hang the 'closed' sign on it. When you've finished that, please come to my office. Um, where is my office?"
Katie gave her the directions to the main office and then set about locking up. While she wondered what was about to happen next, she also thought about the tall, very buxom woman she'd just met. She began to fantasize about being forced to undress and then to crawl on her knees to Cynthia as she waited in her chair. She thought about having her hair pulled and being made to lick Cynthia's pussy. When she realized how wet she was getting, she stopped fantasizing and continued on her way to the office.
When Katie arrived in the doorway to the office, she paused to observe the new owner as she bent over the desk sorting through some papers. Cynthia was a little shorter than herself. Although very athletic looking, she had quite large breasts that appeared ready to fall out of the plunging neckline of her black dress. Katie could see the edges of the black bra that prevented that from happening.
Katie knocked softly.
Cynthia looked up, smiled and invited Katie to come in and sit down. "Make yourself comfortable, Katie. I have a few things I want to ask of you."
As Katie took a seat in the chair directly in front of her, Cynthia sat down in the plush leather chair behind the desk.
"I'll get right to the point, Katie. I'm going to be making a lot of changes here at the gallery and I need someone I can count on to help me do all kinds of things. I need someone who is familiar with what's been done in the past and who is willing to help make changes for the future. I need someone who is attentive to my business needs as well as my personal needs. I need a personal assistant and I want you to be that person. Before you say anything, let me say that I've had my eye on you ever since I saw you at the company holiday party. I know what a dedicated worker you are. I know you keep up with the latest styles. And I must say I'm very impressed by you.
I know you're married and have children, so I took the liberty of calling your husband to see if he'd approve of your going on overnight trips with me, often with very little notice. Jamie said that wouldn't be a problem as long as all of your expenses are covered. I assured him that all expenses for any trips you take will be covered, you'll get bonuses, and you'll get a few additions to your wardrobe, too.
Before I get your answer, I want to make it perfectly clear that in addition to arranging meetings, handling papers and other normal business related activities, you'll also be running errands for me and doing other things that may seem menial or maybe even a little humiliating to you. The plus side, though, is that you'll get to meet all of the artists that will be exhibiting work here. You'll go to parties with me. We'll go shopping together. And, if you do everything you're told with enthusiasm, you'll make me happy, you'll make plenty of money, and you can become an integral part of the success of the gallery. Oh, and you'll get a company car. I think you'd look good behind the wheel of a metallic storm red Mercedes SLK300 roadster, but you can pick any color you want. Actually, you can pick whatever car you want that doesn't cost any more than one of those, but I happen to know there's one available at Worrells if you want it.
Oh, my! I'm getting a little ahead of myself. I haven't even gotten your response yet. One more thing! If you accept the job, you'll have to go to Castlemaine with me tonight to speak with a new artist. What do you say?"
Katie was thinking about a new car and wondering what Cynthia meant by "a little humiliating." After remaining silent for several seconds, she asked if she could ask a few questions first.
"Certainly, Katie. Ask whatever you want. I want you to be comfortable with every aspect of the job."
"Well," Katie began, "I don't have a lot of business experience. If I don't know how to do something, I don't want to disappoint you. Are you willing to help when I need it?"
"Not a problem, Katie! In the beginning, you'll be doing a lot of small tasks, going to pick up things for me, and just generally being a companion for me on the trips. As time goes on, I'll give you a little more to do, but not without giving you whatever support you need. Next question."
"You said if I do everything I'm told with enthusiasm, I'd make you happy and make plenty of money. You also mentioned something about doing things I might think are a little humiliating. Can you give me some examples of what that might entail?"
Cynthia laughed before saying, "It's not as bad as you make it sound, Katie! But since you asked, I'll give you an example of what might happen this weekend in Castlemaine. I want to sign an artist who specializes in photorealistic fetish paintings. All of the works I've seen are of her girlfriend in bondage. She says it's her girlfriend, but I swear she's got to be her slave - the things she has to do! Anyway, in some of the paintings, her girlfriend is performing oral sex with another woman, or she's being fucked with a strap-on, or having all sorts of things stuffed into her pussy or arse. Lesley, the artist, says she likes to get new acquaintances to do things to her girlfriend. She then photographs whatever is done and later paints from the photos. It's conceivable that you'd be asked to do something kinky to or with her girlfriend. If you do it and act like you're enjoying it, it could help to get Lesley signed on with our gallery. Does that explain it better?"
"Um, yes, yes it does," replied Katie. "If I accept the job, you said we'll go to Castlemaine tonight. I have no idea what clothes to pack, or even if I have the right clothes to take."
Cynthia interrupted. "If you say you'll take the job, I'll take you shopping right now and buy you everything you'll need for the trip, all the way down to a toothbrush. And don't worry about deciding what kind of car you want. We'll take care of that after we're back. I'll let you drive my car until you get a new one. It's not as sporty as the SLK300, but it does have room for luggage. It's a black, ML350 SUV."
Katie's mind was racing, thinking about a new Merk roadster, free trips, free clothes, making more money, and the possibility of having some kinky fun. "I'd be a fool not to accept the offer," she told Cynthia.
"Great! Fantastic!" shouted Cynthia. "Now let's go shopping so we can be ready to leave early. You call Jamie and tell him the good news. Here, use my phone."
Katie took the phone and called her husband. As she started to explain about the trip she had to take that evening, he interrupted and said he knew all about it. He assured her he'd take care of everything until she returned, wished her a great time and told her to do everything asked of her.
As she was saying her good-byes, Cynthia patted Katie's bum and said, "Come on, girlfriend! We've got shopping to do!" She handed the keys to Katie, grabbed her hand and pulled her towards the door. "I'm so excited about having you as my personal assistant!"
After both were in Cynthia's car, Katie asked, "Where to?"
"I know this boutique that has the perfect clothes for this trip. Take a left out of the car park and go straight until I tell you to turn."
Katie did as she was told, driving carefully so as not to cause any harm to her boss' vehicle. Cynthia talked a lot, telling Katie of her vision for the gallery. Every now and then she'd ask what Katie thought. Mostly, Katie simply agreed without any explanation.
When they arrived at their destination and entered the store, a salesgirl greeted Cynthia by name. Katie was impressed. "Do you shop here often?" she asked.
Laughing, Cynthia said she probably kept them in business. "We need to look at some sexy, slinky dresses. The kind that leave very little to the imagination! You know I want a black one, but for my new assistant, I'm thinking a deep red would be right."
The salesgirl showed them several different styles before Cynthia picked a black one and a red one off the rack. "Come on. Let's go try these on."
To Katie's surprise, Cynthia followed her into the dressing room. She didn't say anything as she started to remove the dress she was wearing.
"You know, Katie," Cynthia said, "There are so many times I wish my breasts were smaller like yours." Cynthia unhooked Katie's bra and pulled it off. With both hands, she gently squeezed Katie's breasts. "Oh, those are perfect! I'll bet Jamie loves to play with them. I don't know why you hide them under a bra. When you're with me, you won't. I want everybody to know what perfect breasts you have - not like these huge things! I have to admit, though, they do get me a lot of attention." Cynthia removed her bra and let her breasts bounce free. "I mean, really," she continued. "They get in the way when I try to use a water fountain. Whenever I have to wear a bikini, I have to get a custom made top to keep them under control. That's one reason I prefer going to clothing optional beaches, but look at the tan lines they cause." Cynthia raised her breasts up to show the pale skin beneath them. "And feel them. Go on, Katie. Give them a squeeze."
Katie blushed a little. She could feel a rush of warmth through her pussy as she cupped her boss' breasts in her hands and fondled them. Even though she was amazed at what she was doing, she kneaded them and eventually gave both nipples a firm squeeze.
Cynthia smiled and pinched Katie's nipples. "Look how pretty your nipples look - perky and hard. Not mine. You really have to torment them to get them to look good." Cynthia demonstrated by pinching, pulling and twisting her nipples until they stood up like Katie's. "Damn! I'm getting horny! I'd better stop or I'll be forcing myself on you soon!" She laughed out loud before telling Katie not to worry.
"When you wear a slinky dress like this, Katie, you can't wear anything underneath it. Let me help you slip off your knickers so we can see how you look in it."
Cynthia kneeled in front of Katie as she pulled down the silky smooth panties. "Beautiful!" she exclaimed. "But you'll have to shave off that little wisp of a bush before we leave for the meeting. In the future, I'll take you to the girl who waxes me and she'll get you really smooth."
Cynthia helped Katie put on the dress, took a step back and stared. After shifting her head from side to side, she reached forward and pinched Katie's nipples. "Oh, yeah - now that looks great! Lean forward and let's see if you fall out." Katie did as instructed. "Oh, almost. You'll have to be careful if you must bend over in public. Turn around and let me check out your bum." Katie shifted her position and for fun, wiggled her bum at her boss. "Damn, girl! I may have to take you for real!" Katie giggled and wiggled some more. A moment later she felt the hem of the dress rise and then received a sharp hand smack on her butt cheeks. "You fucking tease! I'll have that arse before the night's over!"
"I have to wait?" Katie asked playfully.
"I'm afraid so," replied Cynthia. "We've got to buy a few more things for you and then head to Castlemaine for our meeting. But as soon as I get a chance..."
Cynthia paid for the dresses, some shoes and a few other accessories and then whisked Katie on to the next store. Within another couple of hours or so, Katie had new luggage, dresses, shoes, lingerie, toiletries - everything she needed for the trip, including a purple Feeldoe®! Once everything was packed, Cynthia handed the keys to Katie and told her it was time to drive to Castlemaine. "Hop into the car and pull the hem of your dress up so the truck drivers can get a peek at your bits. It'll be fun. Go on!"
Katie pulled her dress up around her waist and got into the driver's seat. Turning to Cynthia she said, "Don't you want me to sit on a towel or something? I'd hate to leave a spot on your seat."
"Why? Are you wet, too?"
Cynthia turned and reached her hand between Katie's thighs. "Let me feel." She easily slid a finger inside Katie's sex and began rubbing Katie's clit with her thumb. "Don't worry about it. I had all the seats treated with a stain repellant." Cynthia pulled her finger out of Katie's pussy and placed it into her own mouth. "You horny slut! Jamie told me you fantasized about being with another woman. Looks like he was right! I'll wait until we get to our hotel in Castlemaine to find out just what all you've been thinking about. But right now, you need to concentrate on driving."
Cynthia turned on the GPS navigator, entered the address of the hotel in Castlemaine and then sat back in her seat with her legs spread and her own dress pulled up. As Katie followed the driving instructions, Cynthia gave more details about the artist they were going to meet, where they'd meet, and what Katie was expected to do. Occasionally, as a big truck would pull up alongside their car, Cynthia would wave at the driver to get his attention and then point at Katie's crotch, or if the truck was on her side, she'd wave and then finger herself. There were several near wrecks as the drivers tried to watch the show and keep driving.
When Katie finally arrived at their destination, Cynthia went to the check in desk, completed the registration form and got the room keys.
"I guess I wasn't clear about how many rooms I wanted. There's only one room available. It'll just give us more time to get to know each other."
The two women handed their luggage to the hotel porter and followed him to the room. When he opened the door, Cynthia walked in first and, seeing only one bed, asked if there was another. There wasn't.
"Well, Katie, it looks like we'll have to share a bed! We'll really be getting to know each other well, Katie, not that another bed would mean we wouldn't. Tell you what. Let's get a shower before we change into our new dresses. I'll even shave your pussy for you!"
Feeling more bold than usual, Katie responded, "Only if you eat me first!"
"Race you to the shower!" exclaimed Cynthia.
Both women quickly undressed and hurried to the shower. Acting like a couple of horny college girls, they exchanged gropes and pinches before Cynthia kneeled, spread Katie's pussy lips and started licking up and down the juice soaked slit, pausing to probe deeper with her tongue and then massaging her clit with a circling motion. After many minutes had passed, Cynthia pushed two fingers inside Katie's sex, rotated her wrist so her palm faced upwards, curled her fingers up and then began slowly stroking her fingers back and forth.
"Oh, fuck!" moaned Katie. "I think you've done this before!"
"Just showing you what I like," replied Cynthia. "Remember it and repeat it, and you'll do well in your new job. But right now, just enjoy it."
Katie enjoyed it. She enjoyed it through multiple orgasms, pressing her boss' face hard against her pussy and rubbing her juice all over Cynthia's face. "You nasty slut!"
"You think that's nasty? Turn around, girl!"
As soon as she turned around, Cynthia spread Katie's butt cheeks wide and pushed her tongue into the puckered rim.
Katie bent forward more, pushing her arse into Cynthia's face. "Eat it, bitch! I'll show you who's the boss." Katie reached back, grabbed Cynthia's hair with both hands and pulled her face tight into her crack. Normally Katie would never do anything like that, but she was enjoying this new sense of power, not to mention the probing of her arse.
Cynthia reached between Katie's thighs and shoved three fingers into her pussy. Katie orgasmed almost immediately. Cynthia responded by pushing another finger inside her pussy, stretching it even more.
Moving her feet a little farther apart and pushing her bum back more, Katie cursed her boss. "You fucking ass wipe!"
As quickly as Katie said that, Cynthia forced her thumb inside Katie's pussy, pushing her hand inside up to her wrist. As she wiggled her fingers inside and rotated her hand back and forth, Katie's body shuddered with another powerful orgasm.
"Fuck! Fuck! Oh, fuck!" Katie yelled over and over. Her body trembling, she leaned against the wall of the shower.
"I thought you'd like that, girl. It was worth burying my tongue in your arse. Next time, you may not be so lucky, but you can count on getting fisted again. That's one of my favorite things to do." Cynthia tickled the walls of Katie's pussy another few seconds before making a fist and slowly withdrawing her hand, stretching Katie even wider. "Time to shave off that bush and then get ready for the meeting."
"You're not stopping now, are you?" asked Katie.
"Don't worry. Later on we'll pick up where we left off. Right now we need to tend to the real business."
After Cynthia expertly removed all of the hair below Katie's waist, both women rinsed off and got out of the shower. As they took turns drying each other, Cynthia gripped Katie's nipples tightly and told her, "I hope you aren't too tired for our meeting. I have a feeling Lesley will want you to do something with her girlfriend."
The two women went about drying and styling their hair, applying their make-up and dressing. Cynthia wore a plain bra but nothing else under her dress. Katie wore nothing at all under hers. It was obvious, the way the dress clung to her body, revealing every subtle curve. Smiling broadly, Cynthia pointed out the rounded outline of the recently fisted pussy. "I ought to give your clit a tug so it'll show, too." She reached under Katie's dress, squeezed her pussy hard and worked her clit until it protruded like a tiny, erect penis. "Hmmm, pull on your clit and your nipples stand up, too! And try not to get your dress wet, girl."
"After what you just did, I don't know if that's possible," Katie replied. Jokingly, she continued, "Bitch! Just you wait!"
"Yes, I suppose I'll have to wait. It's time to go and meet Lesley. I'll drive this time."
They went out to the car, got in and Cynthia drove away. In just a few minutes they arrived at Lesley's cottage. Once they were both out of the car, they checked each other's appearance. At the door to the cottage, Cynthia gave Katie's nipples a quick squeeze. "I just love the way those stand up! Eat your heart out, Lesley - she's mine!"
Shortly after ringing the doorbell, the door was opened by a totally nude girl. Her nipples were pierced and stretched by decorative metal shields that held the barbells taut. Her clithood piercing was vertically oriented. The silver-colored barbell must've been a 2 gauge and had an even larger ball on the bottom of it. It appeared to press tightly against her clit at all times, causing a steady flow of pussy juice down her thighs. As Cynthia and Katie entered, the nude girl told them Lesley was waiting for them in her studio and to please follow her there. When the girl turned to take them to the studio, they saw a large pony tail protruding from between her butt cheeks, swaying to and fro as she walked. Quietly, Katie and Cynthia pointed at it and poked each other playfully. Cynthia whispered into Katie's ear, "I may have to get one of those for you. I'm not so sure about the huge VCH, though."