Affairs Assistant Ch. 04

School had started up again. My friends were planning dates for homecoming. Most of them were fucking older college guys so it took a lot of persuasion to have a date to the dance. While everyone was sliding on dress-code appropriate gowns, I was sliding the zipper of a skin-tight cocktail dress up my side. My boss, Mr. Rob Sterne, had bought it for me along with a new car and standing appointments at an expensive downtown hair and nails salon. I felt sexy and sophisticated, even though I was just barely eighteen and I was, in fact, a virgin. My boss didn't know that, though.

I was nervous because I was on my way to my first "work party" at Mr. Sterne's lavish home. My search history was full of orgy porn and frantic questions about what to expect with group sex. Since I had gotten the job, I realized that I was going to have to part with my virginity. I was scared, but the image of my boss's face would float into my head each night as I masturbated. It's what kept me coming back to work. I was curious. What would it be like to be used by him?

I pulled into the dark driveway in the middle of the night. The pathway to the home was lines with dim, orange lanterns. The large country home had lights on in every window and I could hear party chatter as I approached the front door.

Mr. Sterne's daughter swung open the door to greet me. She was the same age as I was and seemed to be more involved with her father than either of them had told me.

"Hi Jamie," she giggled.

She was wearing the exact same dress as me, but in a slightly smaller size as my cleavage was slipping out of the top of my dress and she barely had any.

"Hi Lynnae," I breathed nervously.

She led me inside.

The house was full of men and women, all my parent's age or older. They were wearing black tie clothing and holding champagne and wine in sparkling glasses. As I entered the foyer, several smiling faces turned to face me.

"Welcome, Jamie," said Mr. Sterne walking down the marble stairs toward me.

"Good evening," I said. My pussy suddenly felt wet at the sight of him. I glanced at his pants, hoping to see his hardness and gauge his dick size.

He noticed my gaze and his face became stern. "Come with me, you two. Our guests are waiting." He did not take my arm but I felt his forcefulness in the way he walked past me. I immediately turned and followed him, his daughter by my side.

He led both of us into his office and closed the door behind him. He reached into the drawer of his desk and began placing objects in front of us. "And you both are wearing the garters and brassier I provided to you for tonight?" he asked, his voice void of emotion.

I nodded. Lynnae looked at me and smiled.

"Is that a yes, Lynnae?" said her father.

Lynnae's smile faded and nodded at Mr. Sterne. He walked around the desk and took the objects in his hands to us. He clasped a leather collar around my neck and clipped a long leather leash to the collar. He did the same to his daughter.

He held up a swat and said "Your job tonight is to excite my clients. Everyone in the sitting room are new clients and you two are going to represent how desperate my business competition is. It's very important to stay in character during this. It's an acting job. I'll be watching to make sure I don't see any mistakes."

My mouth was dry and I cleared my throat uncomfortably. "Mr. Stern, this collar is really tight, can I loosen it?"

Rob turned furious eyes on me but said nothing. Instead, he touched the swat to my exposed breast, bulging from my dress. The touch was soft and delicate. Almost loving. It did not match his angry glance. Then, he used the swat to slap my skin in the same spot, my body jumped and his eyes were fixated on my breasts.

"Dad, don't make her red. They might do that to me if they know you can do it to her," complained Lynnae, her hands clasped behind her back as if standing in a formation.

Rob raised the swat and then lowered it, deciding at the last moment not to share the stinging pain with Lynnae.

He yanked our leashes in his hand and lead us into the foyer once again. We walked through the fascinated crowd of men and women. I couldn't help but notice their knowing grins and their whispers as we passed. Two men opened glass French doors into an ornately decorated sitting room. On the plush velvet sofas were six men and two women, all in business clothes and holding cigarettes or glasses of brandy.

The adults looked astounded, but smiles crept over their faces.

"This is my assistant," Rob said, yanking on my leash. I tripped on my stilettos and fell to my knees. "She's like my competitors. She's powerless. She's nothing. All she does is follow my lead because that's all she can do to survive. If I interact with her at all, she's thankful for it." She'll do anything," he said. His voice was firm but casual, as if he was describing his day. He leaned over my kneeling body and pulled hard on my dress, forcing it below my breasts, exposing me.

One of the man whistled. Another one tugged at his crotch and looked at my hanging breasts in amazement.

My leash was yanked again, urging me to my feet. I did so and Mr. Sterne led me to the sofas, forcing me to stand in front of each person but keep my eyes on the ground.

After I had stood in front of each person, He pulled Lynnae to her feet. "This is my second assistant for the day." He stared at her and she looked back up at him. "This is my daughter."

One of the men whistled again. The others made perverse sounds.

"She'll do anything I say. Not just because I'm her father. But because of who I am. Everyone in my business is the same way."

"Pull her dress down," called one of the men.

Instead, Rob yanked the leash, knocking her sideways a few steps. She reached up to her side and unzipped her dress. It fell to her feet, revealing her slim, tanned body dressed in see-through lace lingerie.

"Oh my fucking god," said one of the men.

Our leashes were handed to the two women clients. At first they sat in embarrassed silence but started laughing as the men reached over to squeeze my breasts or touch Lynnae's underwear.

After a dare from the men, the woman holding my leash leaned forward and put her mouth around my right nipple, sucking as if he was desperate for milk from me.

I had never felt this before. My mouth opened and an unexpected moan escaped. At this, one of the men positioned his body behind mine and used his hand to spank my ass as hard as he could. My body jolted and the woman pulled her head back, releasing my nipple from her mouth in laughter.

I felt the man behind me push the bottom of my dress up around my hips. His hands eagerly pulled at my skin, squeezing lewdly and breathing hard into my ear. "You're such a hot piece of ass," he breathed into my ear. I felt his tongue against my skin and I shifted uncomfortably. He reached over my shoulder and took my leash from the woman. He pulled it hard so that I fell onto my hands and knees in front of him.

I looked up and noticed Rob sitting in a chair in the far corner, watching me.

Lynnae was being braced around the room by one of the men. He was pulling her leash and telling her to dance. One of the women stood up and danced with her, grinding against Lynnae's young body.

The woman reached around Lynnae's body and unclasped her lacy bra, exposing her small but perky breasts. Her nipples were a delicious brown color against her skin. She seemed proud of them. She smiled as her lingerie was ripped off piece by piece.

I stared at her, watching as her fully waxed pussy became visible. Her slit was visible as she faced forward. My hiss jerked at the sight of it. So beautiful.

The man holding my leash pulled me to my feet when he noticed I was staring. He took everything but my pantyhose off.

One he had done this, he got to his knees and ran his tongue up my legs, wetting the pantyhose. He pushed me backward and I fell onto the velvet sofa. Clothes were coming off left and right. The women sat opposite us, rubbing themselves. Their faces were rosy from drinking.

The men had their dicks in their hands occasionally putting them close to our faces.

Lynnae looked over at me and I could barely make eye-contact, she was so gorgeous.

She leaned over and kissed me, her tongue curving around mine.

"Oh fuck," said one of the men standing in front of us. They all started to masturbate together as we continued to kiss.

I eagerly moved my body close to Lynnae's as we made out messily. I moaned into her mouth and she moaned back into mine. The men were rubbing their dicks and occasionally reaching over to pull their neighbor's cock or rub the heads of their cocks together to share the wetness that was beginning to appear from their tips.

Two of the men started to kiss and Mr. Sterne fixed his eyes on them, watching as they fondled eachother excitedly.

The two women on the opposite couch were watching as well. Their fingers were sliding into their pussies, mimicking the thrusts that the other four men were giving to their hands in front of Lynnae and I.

I felt one of the men's bodies lean over me, his groin in my face. His dick bobbed in front of me and he pushed it against my wet mouth. I could taste his salty pre-cum. He forced his dick in between my breasts suddenly and I could feel it pulsing against my skin. He spit on my skin to make it slippery and started to fuck the deep cleavage between my breasts.

The three other men were closing in on Lynnae. They pulled on her leash to pull her to her knees on the floor. Two men had their dicks dangerously close to her mouth while the other one's hand found her bare pussy.

Mr. Sterne suddenly objected. "Enough. Just use the first assistant. You can't have my daughter."

The men backed up except for the one touching her between her legs. He kept his hand in her slit and rubbed slowly. "Come on, Rob. You want to see how she does." He pulled her leash and began to kiss her like I had.

"Enough," warned Mr. Sterne.

Lynnae moaned, whether out of pleasure or discomfort it was impossible to tell.

The man's hand then flew to his cock and he forced himself into her slit, his dick disappearing in the deep fold of her pussy. His mouth was open in complete obsessive compulsion. He almost drooled. He pulled Lynnae's leash again, making her thrust her hips and take in the tip of his dick.

At this, Rob got up and threw a brandy glass at the wall. It shattered into a million pieces and everyone froze.

"Out," he said, angrily.

The man stood up quickly and collected his clothes. But not quickly enough. Mr. Sterne walked over and punched the man hard in the jaw.

At this, the room dissolved into chaos. The clients got dressed and left the sitting room.

Lynnae, still naked, reached over and took my leash in her hand.

She led me out of the room as well. We could hear more punches being thrown by her father as we ascended the stairs, toward her bedroom.