The Education of Holly Fogg

When she called to inquire about the Personal Assistant job she'd seen in the Sunday paper, the man who answered informed Holly that the position was fairly demanding and required some unusual duties. Holly assured the man that she was up for the challenge. He also explained that position would require a certain type of dress -- skirts only -- which Holly didn't see as so unusual and again assured the man that she could fulfill that part of the job with little difficulty. He gave her the address and asked that she be on time.

Holly stood on the front steps of an incredible sprawling estate in a part of the city she rarely saw being young and broke. She was wearing her nicest interview outfit, a second-hand soft pink blazer with a short, flowered print skirt that she struggled to keep down under the breeze. Under the blazer she wore a white silk camisole with no bra. She hated being confined and her breasts were such that she could get away with not wearing one if she kept the blazer on during the interview. Hopefully Mr. Bennington's house would not be too warm.

She was ushered to a study and told to sit while she waited. Mr. Bennington arrived only moments later. He was young, maybe 33, and relatively attractive. He walked across the room without saying anything to Holly and sat in a wingback chair in the corner.

“You are here for an interview, I know, but I have some paperwork that I'd like you to sign before we begin. Please come here and review it. If you do not agree to sign it then I will have my aide show you out.”

Holly perused the paperwork. She was no legal expert, but it was something to do with sexual harassment. She understood she was waiving any rights she had and would be unable to press charges or file a complaint. He must have been burned by another employee, probably some young girl who was all hot for him and got pissed when he didn't return the feelings. Holly didn't think twice about signing. People were so overzealous about sexual harassment these days...plus, she wouldn't mind a little flirting with her boss.

“Excellent,” he said. “I take it you read the paperwork fully before signing?” Holly nodded. “Please take off that blazer and stand here in front of me, then.” He motioned to a spot just in front of where he was standing.

Holly stood in front of Mr. Bennington. This was a weird way to start an interview.

“I asked you to remove your jacket, Ms. Fogg. Please take it off and put it on your chair.”

Holly, remembering she wasn't wearing a bra, took her jacket off, placed it on the seat and crossed her arms in front of her chest to hide her lack of lingerie.

“Please put your arms against your sides. Ooohh... I see that you're not wearing a bra. Is this how you interview for all your jobs?”

Let the flirting begin, Holly thought. “Uh, no sir, I just didn't think I'd have to take my coat off. My clothes generally don't go flying so soon.” Holly chuckled. Mr. Bennington did not.

“Please remove your shirt, seeing as how you're not hiding much anyway. I would like to get a good look at your tits,” he ordered.

Holly was starting to get a little nervous. This was a little over the top. Could he get away with this? She supposed he could so long as he didn't touch her...that would be assault. Clearly this was why he had her sign that form to begin with. She removed her silk shell and placed it on the seat with her blazer.

“You are very attractive. That's what I require of my personal assistants, Holly. I explained to you that the job was of an unusual nature. Please turn around so you're not facing me and slowly slide your skirt down to the floor. Bend slowly to pick it up before putting it with your other garments.”

Okay, this was getting ridiculous. He wanted her to take her fucking skirt off? No way. Screw this job. He was hot and all, but she wasn't going to be ordered around by this whack job. She walked over to get her clothes.

“Excuse me, Ms. Fogg, I gave you an order. If you're forgetting, you did just sign an agreement, a contract, if you will.”

“All I signed was a waiver to my rights under the Sexual Harassment law...that's it. I didn't sign anything about taking my clothes off. Fuck you.”

“Oh, if you come here for a moment, Ms. Fogg, you did sign a contract with me. Part of that contract, it's true, waives your right to file any complaints about sexual harassment. However, if you had read the entire document - as you said you had - you would have seen that, in addition, you are now bound into a contract as an indentured servant to me, belonging to me, for the next two years in return for food and lodging. It's all on pages two and three. I know you wouldn't want me to call the police because I did do a little investigating and you have a warrant or two for drug charges, do you not? It appears as though you've been evading the law. “

Holly grabbed the contract and reread. It was true. She was fucked.

“If I'm already hired, then why are you calling this an interview? Why are you making me take my clothes off? I've been a personal assistant before and never had to take my clothes off.”

“You are to be my personal sex assistant. You are essentially my slave. You will do whatever I ask of you or you will be punished. Now, please resume your position in front of me and remove your skirt as ordered. I will not give you another chance.”

“Fuck that. I'm not your fucking slave. If you want my clothes off, you're going to have to take them off yourself.”

With that, Mr. Bennington rang a bell and two large gentlemen came into the room. One grabbed her and held both arms tightly while the other removed her skirt and shoes. Holly kicked and spit and attempted to bite the men, but to no avail.

“Thank you, Jake and Tony. Please help yourself to Ms. Fogg for your help.”

Mr. Bennington sat in the chair and watched as Jake pulled down his linen pants to reveal a throbbing cock standing at attention. While Tony held Holly's hands behind her back and forced her to her knees, tears streaming down her face, Jake brushed the tip of his swollen cock on her lips, smearing precum as he went. “Open your mouth, slut. This is what you get.” Jake barely waited and jammed his dick in her mouth violently. Holly was gagging. The men smiled. Jake pumped away, playing with his balls as he fucked Holly's mouth. “Wow, boss, she gives great head. Can I blow on her face?”

“No Jake, I want her to eat it all. Cum in her mouth,” Mr. Bennington replied.

Jake did has he was told and Holly started coughing. Tony forced her onto her feet and walked her over to the arm of the couch. He bent her over the arm, spread her legs open wide while Jake held her hands and fondled her tits. Tony fingered her pussy from behind. “Man, you're awfully wet. I think you like sucking cock, don't you? Feels like you want to be fucked to me. Tony's cock was poking through his pants and he quickly undid his zipper to release it. He rubbed the tip of his cock up and down the crack of her ass and over her pussy lips. Holly screamed a bit when she realized which hole he was favoring. She had never had anal sex before because she heard it hurt. Before she could protest, Tony's huge throbbing cock was almost entirely filling her asshole as he began to pump her.

“Pll...easee stop. It hurts. Please, I'll do anything. Owww...”

“oooh...that's right. Oh, you're so tight, baby. You need to do what you're told, don't you? I sure hope you don't, though. I could fuck this little asshole all day long.” Tony reached forward and grabbed Holly's tits as he thrust into her a few more times. Tony pulled out and came all over her pussy lips and ass and watched it drip down. Holly lay slumped, whimpering.

“Thank you, Jake and Tony. Please be sure the door is locked on your way out,” Mr. Bennington said when the men were finished.

“Now, Ms. Fogg, the punishments can get much worse. I would like to think that Jake and Tony have taught you a bit. It excited me very much to watch you. Please sit on that chair just across from me.” When Holly hesitated, “I don't want to have to ask you again.”

Holly stood and walked to the chair. There she sat, cum all over her ass and pussy, cum in her mouth sitting naked across from this man. What did he want her to do now?

“Please touch yourself. I want you to feel as good as Tony and Jake do. Make yourself cum the way you did this morning before arriving here.” How could he have known that she fingered herself on her sofa this morning before arriving?

“If you're wondering how I know...I watched you. After you called last week, I had a camera installed in each room of your house while you were out shopping. I've been watching you ever since. It's good that you like to cum because I'll be expecting that while you're in my employ. I haven't had a girl that's been as active as you. Why, just Tuesday, you masturbated seven times after getting home from work. I like when you lie on your belly grinding against a pillow or your hand, but for now, just spread your legs and do what you will.”

Holly was astonished. He'd been watching her? Fearing another intrusion from the Beef Patrol, Holly closed her eyes and tried to imagine something that would make her hot. She started rubbing her clit slowly with two fingers. Her neighbor, that older guy, she knew he wanted her. That made her hot. When he had broken his leg in a car accident, she'd gone over, dressed very slutty and made him dinner. He had an erection all night. At one point, Holly sat on his lap in his rocking chair and grinded against him for a few minutes, pretending to rock, but really, it was turning her on to feel his hard cock rubbing against her ass.

She had listened as his breathing became labored. And just before she thought he would blow his load in his lap, she hopped up in such a way that her skirt was positioned to show she she had no panties on. She made a long time of staying bent over, as though she were examining something on the floor. Then she kissed him goodbye on the cheek and went home to fuck herself with a dildo. She made sure to do it in her room, which shared a wall with his room and she came so loudly, even she was surprised.

Now, she was really into it. Two fingers were in her pussy and her other fingers rubbing against her clit.

“Open your eyes while you cum for me, Holly. I want to watch you.”

Holly opened her eyes and began to cum loudly. She could feel Tony's cum dripping down her ass crack now mixing with her juices.

“What a good little slut you are. I like when you behave for me. Now I want you to tell me the story that just got you all hot while I jerk off. Normally, I would make you jerk me off, but you've had a trying day and I'll do your job for you today. So, as I get my cock out of my pants, what was it that you were thinking about while you fingered yourself? Don't leave out any details.”

END PART ONE