Dirty Dealings with my Step-Mom

My father is a very wealthy man. He's worth millions, but he's always said he's never felt richer than the day I was born. Well past fifty and on his third wife, he had begun to suspect that he would never have a child and he was so pleased that it was a son. His wives have come and gone, but he and I have always had a happy life together.

During my second year of college, he turned 75 and had a huge party. I came down from Harvard to spend the weekend at his Connecticut estate. He suggested I bring some friends my own age, but truth be told, a shy biochemistry major has few friends. This is what left me in his study at the height of the party, just tired of mingling with people more than twice my age. I plopped down in Dad's plush leather chair and undid my bow tie.

I was contemplating spending the rest of the party hiding in here when Olivia walked in. Dad's sixth or seventh wife, she was possibly his most attractive. At 27, she still managed to convey an experienced air, lithe, cat-like. Her eyes were so heavily lidded, she seemed almost sleepy in her confidence. However, her smile shot out at the most inopportune times, disarming you mid-sentence and reducing you to a babbling freak. She took great delight in teasing men, though my father insisted she was totally loyal to him. As she was nearly six feet tall, with a perfect figure and long curly brown hair, I never minded her teasing me.

"Hiding out, Rick?" She strutted over toward me, looking incredibly slinky in her sparkling blue gown.

I laughed nervously. "Just trying to find a comfortable place to sit."

She laughed knowingly. My father's chair was notoriously the most comfortable in the house. She hopped onto the desk and leaned back luxuriously. I couldn't help staring as her back arched slightly, pushing her C cup breasts out. The open sides easily revealed she wasn't wearing a bra. As she crossed her legs, the sit in her skirt opened, giving me an eyeful of her gorgeous taut legs. Dad really knew how to pick them.

I looked up to catch her watching me over the rim of her champagne glass. "See anything you like?" I stammered for a second and she just laughed again, her breathy, throaty laugh that sent chills up my spine. "Relax." She gently pushed me so I leaned back in the chair. Then she opened the box of Romeo y Julietas on my father's desk and offered me a cigar. She lit the cigar for me and I relaxed a little bit, enjoying the quiet moment.

"You know, Rick. It's unfortunate to say, but it's not long until you'll be the man of the house." I nodded, puffing on the cigar, wondering where she was going. "Your father and I have an arrangement." Here it comes. It had happened before: Dad's wife trying to tell me exactly how they were supposed to be provided for. I knew it was bullshit. Dad had shown me his will. Other than a life insurance policy benefiting his current wife, the whole fortune was left to me.

Olivia paused before launching into her speech. She bit her lip slightly and I could see it trembling between her teeth. "You see Rick, I fuck your father and he keeps me looking the way I deserve to." This was different. "The clothes, the jewelry, the personal trainer. All of it. I live the good life by keeping him happy."

She was trying something and for once, I felt like I had the upper hand. "What exactly are you saying here, Olivia?"

She raked her manicured fingernails across the exposed part of her chest. "It's an arrangement I hope to maintain after he's gone."

I coughed. "What?"

Her tongue ran across her lips, painting to a high glossed red that reflected the lights from outside. "If you keep me here, I'll start fucking you."

I was in shock. I simply did not know how to react. Somehow, with living in this big empty house and being so involved in my studies, I was still a virgin. And now a gorgeous woman was trying to sell herself to me.

Before I could say anything, Olivia slid off the desk. She kneeled on the floor in front of me and reached up between my legs. "I could make you so happy, Rick," she purred, squeezing my cock where it was growing inside my tuxedo. "Please. Don't you want me to make you happy?" Her hands quickly opened my pants and my cock quickly rose out into the dark study. She grabbed it in both hands and kissed the tip gently, taking away a bit of pre-cum. "Don't you want me to?"

Before I could answer, she engulfed my cock with her mouth. Her wet mouth quickly took me in up the hilt. I could feel her tongue lightly tracing the underside as she dragged her lips back up to kiss the tip again. I squirmed in my chair, finding this sort of teasing maddening. She looked at me, her eyes all conspiracy, secret pacts and most of all, pleasing me in every way.

And suddenly I felt like the million bucks I was worth. I leaned back and closed my eyes and her head started bobbing. Her breathy sighs were music to my ears even as they blew across my swollen member. I puffed on the cigar and picked up her champagne, feeling as though I was king of the world. As her bobbing increased, my balls started to tighten and I grunted.

And she stopped.

My eyes flew open and she was standing in front of me, hands on her hips and a wicked smile on her lips. "Do we have a deal, Rick?"

"Do I have to marry you?"

She grinned at me and took the cigar. She placed it between her pouty lips and took a long drag. "Wicked boy. Want to keep your options open?" She blew the smoke over her head. "Well, you can have all the other women you want and maybe I'll have all the men I want." She climbed onto the chair, her legs on her either side of me, grinding her ass into my tortured cock. "Would you like that?"

"God, yes," I moaned. I had just realized she wasn't wearing any underwear.

She rubbed her swollen pussy lips along the length of my dick. "So? Do we have a deal?" I hesitated. I wanted to think clearly. She put my head right at the entrance. I could feel her juices running onto me. It seemed that at any second, her cunt would swallow me whole, without warning. "Do we have a deal?" Her cunt was pulling me in.

"Yes. Olivia. Yes. We have a deal."

And she let go of the chair's arms and dropped onto my cock without any resistance. I slammed deep into her and she yelped. She held me there for a minute, puffed on the cigar again, then started riding me. She rocked in a steady rhythm, dragging up and down my cock in maddeningly slow strokes. I reached around to grab her ass, but she forced my arms down. "I'm in charge here."

I nodded and gulped. She kept up this teasing, watching me closely, getting off on the way my hands shook and my teeth chattered. "You are just so big," she purred. "Even bigger than your father." My cock twitched slightly with pride. "Mmmmmmm. I love the way you fill me up."

"God, Olivia. I've wanted to do this for the longest time."

She smiled at me, her eyes glimmering slits, her face clouded with the smoke from the cigar. "Have you? You bad boy. Wanting to fuck Daddy's wife. Do you masturbate thinking about me?"

"Yes." I did the first time I saw her, when Dad brought her out sailing with us and she wore a skimpy bikini. Later that night, in my own cabin, I could her screaming while he fucked her.

She started to increase her pace, her purrs becoming coos. "Have you ever spied on me?"

"God, yes." I had. The summer after I graduated from high school, I hid in her closet and watched her dress and undress repeatedly, trying on designer dresses.

She moaned and her wrapped her arms around me, the cigar dangling from her lips. "This has been a long time in coming. Is it everything you dreamed of?"

"Better." I reached around and finally grabbed her ass, sliding my hands up inside the material of her dress, running my hands along her cheeks. They were soft and smooth and I could feel them flexing as she pumped. I squeezed them tight and started bucking against her, jamming deep into her.

She stared screaming. "Oh God. Fuck me. Fuck me hard, Rick. Fill me with every fucking inch of you. I need your cock buried in me. I need it."

I did my best to comply, half rising out of the seat to bang her harder. Her ass clapped against me, and her nails started digging into the back of my neck. Here we were, fully clothed for a formal event, hundreds of people filling the house around us and I was fucking me step-mom for all I was worth.

She was literally howling, her eyes clamped shut and cigar smoke pouring out of her mouth. "Oh my God! It has been way too long since I fucked a young man like you. You stud. Fuck me Rick. I'm cumming. I'm cumming. I'm cumming . . ."

Her pussy clamped around me and I felt the hot rush of her orgasm on my cock. I started shaking uncontrollably. I felt like my entire body was going to explode.

"Yes, do it, Rick. Cum inside me. Fill me up. Cum inside me."

I let go and blasted her pussy walls with wave after wave of semen. I felt as though I'd never stop cumming, my cock spasming and twitching uncontrollably buried deep inside Olivia.

Finally, after what seemed like hours, we both slumped into the chair, my semi-erect projectile still buried inside her. Olivia barely managed to catch her breath.

She sighed contentedly. "I am looking forward to making good on our deal. I haven't been fucked like that since college." I nodded tiredly. She puffed lightly on the cigar and finally put it out. "It's a shame. It almost makes me want him to die sooner."

"What? Why?"

"Well, tiger, you can't expect me to cheat on your father, can you? And certainly not with his baby boy."

"What do you call that?"

"A sample to ensure that both parties are satisfied with the arrangement."

She stood up and my cock dragged out of her with a wet smack. I drained the champagne glass and said, "I'll be very satisfied."

"Good. But when I leave this room, I'm going back out to be a faithful wife to your father again."

"Agreed." She started for the door, strutting again in her high heels. "Where do you think you're going?"

"I just said—"

"You're not leaving this room until I bend you over my father's desk and fuck you from behind."

She laughed and sauntered back over to me, an eyebrow raised. "I may have met my match."

I grabbed her and bent her over, my cock poised right against her lips. "I am more than my father's equal." I plunged inside her, her delighted screams echoing off the walls.