Stepmother's Smorgasburg of Sex #3

Stepmother's Smorgasburg of Sex, #3

Billionaire boss has a final sexually inappropriate requests for Vanessa for money.

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Author's Note:

This story is dedicated to Vanessa for allowing me to write her story. She's brave to have revealed all that happened between her stepson, Brett, and her billionaire boss, John. Unless this had happened to her, she never would have believed this had happened to anyone.

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Stepmother's Smorgasburg of Sex, continued from Chapter 2:

Vanessa agreed to have paid sex with her billionaire boss while pretending that she was the reincarnation of his deceased mother.

Stepmother's Smorgasburg of Sex rewritten and continued from Chapter 2:

"He'll give me five-hundred-thousand-dollars in cash if," I stared at Brett while he stared at me.

My stepson stared at me with his mouth open and his eyes bugging out of his head.

"Five-hundred-thousand-dollars? Wow," said Brett!

He waited for me to continue reading my boss's email. Then, when I paused too long, he asked me what was on the rest of the email.

"If what, mom? What does he want you to do now for him to give you that huge amount of money," he asked?

I stared at Brett before answering him.

"He wanted me to have sex with him," I said reading my boss's email to my stepson.

I stared at Brett in the way that he stared at me. He looked at me with excitement mixed with concern. Yet, I could tell that he wanted me to do it. In addition to receiving the money, I could tell that he wanted to watch me having sex with my boss.

"That's a lot of money, mom. How do you feel about having sex with your boss," he asked? "Can you do it?"

I shrugged and made a face as if I was about to vomit.

"I'd feel embarrassed to have sex with him. Prostituting myself, I'd feel ashamed to whore myself for money," I said. "I'd feel sick to my stomach for him to have sex with my naked body while he imagined that he was having sex with his mother."

I looked at Brett looking at me.

"Yet, it's just sex and it's just the one time. Especially for that amount of money, I can do anything once," I said with another shrug.

I continued looking at my stepson.

"How do you feel about me having sex with my boss," I asked? "Just in case of anything, I'd want you there," I said before he could answer.

He returned my embarrassed shame with a look of sexual excitement.

"That's a lot of money, mom," he said again but not answering my question.

Then, he paused before looking up at me.

"If you're okay with it, I'm okay with it, too," he said.

He paused as if he imagined me having sex with my boss. With Brett wanting me to go ahead and do it, he made my decision for me. Not worried about my boss paying me all the money that he promised, he was an honorable man. That significant amount of money meant nothing to him. With him a multi-billionaire, unbelievably, he made much more than that in a day.

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Stepmother's Smorgasburg of Sex, Chapter 3:

The next day, we arrived at my billionaire boss's high-rise condominium. The man at the desk ushered us to a direct express, private elevator where he inserted a special key. With him working from home, having never been inside of his condo before, I never made it past the front desk when dropping off his messages, his mail, and picking up my instructions for the day.

Unaccustomed to living life so lavishly, I was impressed that the elevator opened to his residence.

'This is it,' I thought. 'I'm here to pretend that I'm my boss's reincarnated mother. I'm going to have sex with him while Brett watches. I'll be needing therapy after this,' I thought.

When he hired me as his personal, executive assistant, I never thought that I'd be having sex with him. When he could have had sex with any twenty-something or thirty-something-year-old woman why would he want to have sex with me?

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It all started when he gave me money to buy expensive, sexy lingerie. I should have known then. Yet, surprised that he gave me money to buy sexy underwear, and not wanting to disobey him, I was confused. Then, with me in his private office behind his closed and locked door, he wanted me to show him what I looked like wearing what I bought.

Making me sick, he asked me to unbutton my blouse. He wanted to see my bra. Then, he asked me to pull up my skirt and spread my legs wide open when sitting across from him on his couch. He not only wanted me to show him my low-cut, sexy bra but also, he wanted me to show him my sheer panties, too.

If that wasn't enough, while I continued flashing him my sexy lingerie, he shocked me as much as he disgusted me. He unzipped himself, pulled out his cock, and exposed himself to me. My boss flashed me his erect dick.

"Look. Look at me," he said while stroking himself to an erection. "Watch me masturbate myself. I want you to watch me cum."

Then, it wasn't until he called me mommy when masturbating himself and I saw his mother's photo on his desk that I made the connection. With me looking much like his mother, I realized why he wanted to see my lingerie, why he wanted to dick flash me, and watch him masturbate himself. I looked like his mother in the way that she looked 40-years-ago. He wasn't masturbating for me. He was masturbating for his deceased mother.

Now I knew why he hired me instead of hiring a woman half my age. In his twisted mind, he masturbated in front of me, as if dick flashing and masturbating for his mother. He stared at my bra as if he stared at his mother's bra. He stared at my panties, my pussy mound, my camel toe, and my pussy slit as if he stared at all that he could see of his mother's cunt through her sheer panties.

'He's such a sick bastard,' I thought.

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As soon as we entered his penthouse condo suite, my boss greeted us warmly and politely.

"Come in. Come in," he said, waving us in with an extended arm of hospitality. "Welcome to my humble abode."

'Humble abode, my ass,' I thought. 'As if I had suddenly died and passed through the gates of heaven, this place is as beautiful as it's huge.'

Yet, with all that he wanted my stepson and I to do by tempting us with vast amounts of money, he was more like Satan than he was like Saint Peter.

Something that I had expected him to do, he surprised me that he didn't kiss me on the mouth. I figured he would have parted my lips with his tongue, and French kissed me while reaching around to feel my ass through my short skirt and panties. Yet, with me supposed to be his mother, he had more respect for me than that. No doubt, he'll be doing all that he wished he had done with his mother later. Instead, he leaned to me to kiss me on the cheek and shook Brett's hand.

"Nice to meet you," he said to my stepson. "I've heard so much about you from Vanessa," he said to Brett.

Then, my boss stared at me while undressing me with his eyes as if I was already naked.

'Here we go,' I thought. 'This is it. This is really it. I'm about to prostitute myself and have sex with my boss for half a million dollars.

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Truth be told, John wasn't a bad man. He was just twisted. He had an unrequited sexual attraction to his MILF of a mother. Had his mother had sex with him when he was a younger man, none of this would have happened. Only, clearly, his mother was a lady. She wasn't an incestuous whore in the way that I am and in the way that he was a perversely perverted, dirty, old man.

With him not going into details, I knew that his father had died early, and he lived alone with his mother and with the servants. With him unaccustomed to anyone saying no to him, I imagined that he wanted to take his father's place in his mother's bed. In the way that he exposed himself to me and masturbated while demanding me to watch, I imagined him exposing himself to his mother. I imagined him masturbating himself in front of her in the way that he did with me.

Only, I imagined his mother not watching him stroking his cock and refusing to watch him masturbate. I imagined her not wanting to watch him cum. I imagined her forcing him to have therapy because he had an unhealthy, sexual attraction to her. Then, when he saw how much I looked like his mother, his renewed, sexual frustration filled his head with lustful desires to have sex with me.

Yet, this was my boss and not some guy that we happened upon on the internet. More than that, now, I was as much of a whore as my boss was a pervert to agree to have sex with my boss. I prostituted myself by accepting money for sex. Now, with him filled with regrets and missed opportunities, he wanted to have sex with me while pretending that I was his mother.

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Difficult not to notice, distracting my attention from his enormous condo, there was a big, black duffle bag on a table by the door. No doubt, having watched enough crime shows on television, that was the money. Not even a day's pay to him, our huge payout meant nothing to him but would change our lives for the better forever.

He unzipped the bag to show us stacks of neatly banded and arranged hundred-dollar-bills, marked with $10,000 in each bundle. As if we were drug or arms dealers making a cash deal, he had nine-hundred-thirty-five-thousand dollars in one-hundred-dollar-bills stuffed in a duffle bag, about twenty-five pounds of cash. I knew he'd not renege on his promise to pay us, and this was the proof. After seeing all of that money, I felt better about having sex with him.

Acting socially cordial instead of sexually perverted, he invited us into an open space decorated with oriental rugs, paintings on the walls, and filled tables, overstuffed chairs, and couches. Light, bright, and airy, the entire condo had floor to ceiling windows with panoramic views. We could look out but no one could see in. I've only seen such luxury penthouse suites in architectural magazines.

We had a drink in the expansive living room, a room that could easily fit a hundred guests. We drank our drinks while looking out at an incredible view that overlooked Central Park. He had a spread of food, crackers, cheeses, fruits, and small cakes. We tried some of those, too.

"I gave my staff the day off. I have two maids, a chef, a driver, a personal butler, and a bodyguard," he said. "New York is a dangerous place, and I don't go anywhere alone and unprotected without security. With him licensed to carry, Bruno is always with me."

He smiled smugly.

"My driver is a retired New York City police detective, and my bodyguard is retired special ops Navy SEAL. Highly trained, they're both armed and dangerous. With a three dan black belt in Judo, my personal butler is no stranger to self-defensive maneuvers also," he said. "I'm well protected."

He looked around the room and up at the ceiling.

"In case someone is foolish enough to break-in, I have alarms and surveillance cameras all over," he said. "There's also a security gate that my staff pulled close and locked whenever we leave the condo. Should someone get the key and access to my private elevator, they'd still be unable to enter with the security gate in place," he said.

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We chatted with him for about twenty-minutes as if we were old friends instead of employer and employee. It was an awkward meeting while knowing that I'd soon be having sex with my boss. After having already seen his erect, naked prick while being forced to watch him masturbate himself and cum, I wasn't looking forward to seeing that again. Yet, willing to be bought and soon to be paid for me being the whore that he wanted me to be, the money was my motivation to go through with whatever he wanted me to do.

With me looking so much like his deceased mother when she was in her prime, he'd be having sex with me while imagining having sex with his mother. Where most men must satisfy themselves by watching porn, reading, or writing erotic stories, he's fortunate that he had the money to play out his personal perversions. Instead of thinking about having sex with him, all that I could think of was the money.

A penthouse suite, he had the entire floor. I'd guess that he had 10,000 square feet of room, if not more. As his private, personal executive assistant, I read that he had paid $150,000,000 for the condo several years ago that was now worth $250,000,000. With real estate prices in New York and everywhere else skyrocketing, $100,000,000 wasn't a bad return on his real estate investment.

Never have been in a place as magnificent as this. While wishing that I lived here, I couldn't imagine living with him. I thought of my boss asking me to marry him because I looked so much like his mother. Yet, much like asking his mother to marry him, he'd never ask me to marry him. Besides, I'd never abandon my stepson for my boss. I loved him as if he was my son.

While sipping our drinks, we stood to walk to the massive windows to stare out at the view. If I lived here, never leaving the condo to venture outside, I'd stare at the view all day while having all that I needed delivered. Then, once finished with our drinks, with him not wasting any more time with formalities, he showed us the way to his bedroom.

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'This was it. This was really it,' I thought again while panicking. 'I'm about to have sex with my boss. I can't believe that I'm doing this.'

Instead of him dick flashing me and masturbating in front of me while I flashed him my bra and panties, I was about to have sex with him. Hard to wrap my head around having sex with him, I couldn't believe that he was willing to pay me half a million-dollars to have sex with him. I couldn't believe that he had already promised us four-hundred-thirty-five-thousand-dollars to watch us having sex with one another while imagining his mother having sex with him.

As perverted as this was convoluted, I couldn't believe that I was humoring him by agreeing to have intimate relations with him. Yet, doing it for the money, how many women would turn down a monetary offer that would make them set for life? Besides, it was just sex. As long as I close my eyes while imagining Brett having sex with me, I can do anything once.

Nonetheless, I dreaded him kissing me while touching and feeling me through my clothes. I was sickened by the thought of him undressing me and stripping me naked. Just as bad as that, I'd have to undress him and strip him naked, too.

Then, there was the sex. No doubt, he'd want to make love to me in the way that he wished he had made love to his mother. He'd want to fuck me in the way that he wanted to fuck her. He'd want to finger and lick my pussy in the way that he wanted to masturbate and eat his mother. Finally, he'd want me to suck his cock, allow him to cum in my mouth, and watch me swallow his cum.

'I'm going to be sick,' I thought.

Controlling myself from doing so, I wanted to vomit.

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As if walking to my execution, I walked with him and my stepson to his bedroom that was bigger than the interior of my entire house. He had Brett sit in a chair that faced the huge bed. Then, with him eager to begin, as if I was my boss's mother, something that he, no doubt, yearned to do with her, while fulfilling his sexual fantasy and having no more regrets, he did with me.

He wrapped one arm around my waist and his other arm around my shoulders. Then, he kissed me. As if I was his wife, his girlfriend, his lover, or his mother, he parted my lips and French kissed me. Having no choice, forcing myself to quickly get in the mood, I returned his French kiss with my long, wet kiss.

'Yuck,' I thought. 'I kissed my boss. Gross. He stuck his tongue in my mouth.'

I closed my eyes while imagining that I was kissing someone else, anyone else, instead of my boss. My boss kissed me with wild, animal lust and wanton desire. As if his mother was Sleeping Beauty, while trying to awaken his deceased mother from the dead, with him trying too hard and forcing something that wasn't there, he kissed me too hard.

To be honest, I dreaded having sex with him. My skin crawled to think of him seeing me without my clothes while touching, feeling me, and fondling my naked body. Feeling as if I was being raped, I couldn't wait to take a long, hot shower after having had sex with him. Yet, with that kind of money that he paid me to have sex with him, I'd never have to do anything that I didn't want to do ever again.

No doubt, getting drunk, I'll be drinking lots of alcohol later to help me forget having sex with him. Yet, my reward was him giving us as much money that I earned in more than ten-years. Instead of thinking of my boss having sex with me, I thought of that big, black duffle bag filled with money. After taxes of around 37%, nine-hundred-thirty-five-thousand-dollars is like earning nearly 1.5 million-dollars before taxes. Many people don't even earn that in a lifetime.

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As if he was my son and I was his mother, he continued kissing me while feeling and fondling me everywhere through my clothes. Then, he slowly undressed me. Again, I controlled myself from being sick to my stomach. I didn't want to ruin everything by vomiting on him. Again, while hoping to trick my mind, I imagined someone else undressed me and stripped me naked instead of my boss.

'I can do this,' I thought. 'I've already shown him my bra and panties at work. I'll feel better once I'm home with all of that money.'

At that moment, a crushing blow to my ego, I realized that my position as his personal, executive assistant meant little to him. All of the work that I did for him was for naught. It didn't matter all that I had done for him in my job responsibilities. He didn't hire me because of my twenty-years of professional experience. He hired me because I looked like his mother.

A time when I should have refused but not wanting to lose my job by not doing what he asked, I couldn't believe it when he gave me money to buy sexy lingerie. If that wasn't enough, I couldn't believe it when he asked me to show him my bra and panties. I couldn't believe it when he dick flashed me and wanted me to watch him masturbate while he called me mommy.

I thought that was it. Not just crossing the line but leaping over the line of what was sexually inappropriate, I never thought he'd give me this kind of money to allow him to watch me having sex with my stepson. Then, from the time that he hired me, it took him a year to build up the courage to arrange for this sexual scenario of me having sex with him.

I undressed my employer and he undressed me, too. I stripped him naked and he stripped me naked, too. This is why he gave us the money. He wanted to recreate what he wished he had done with his mother. No longer having regrets and missed opportunities, a luxury that few men could afford, while he imagined that I was his mother, he wanted to do everything with me that he had wished he had done with her.

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"Call me, Johnny," he said.

He unbuttoned and removed my blouse while I unbuttoned and removed his shirt. He unbuttoned and unzipped my short skirt while I unbuckled, unbuttoned, and unzipped his trousers. I stepped out of my skirt and he stepped out of his pants.

Then, as if he stared at his mother in her sexy lingerie, he took a step back to stare at me in my bra and panties. Mortified, as embarrassed as I felt ashamed, he stared at me as if I was already naked. Only, he wasn't looking at me. Looking right through me, he stared at the imagined image of his mother, Mary.

He took a step forward to feel my breasts and finger my nipples through my bra. With my nipples sensitive to the touch, as soon as he fingered my nipples, they erected. Then, he reached around me to touch, feel, and squeeze my ass through my panties. Finally, he cupped my pussy through my panties, while sliding a slow finger along my pussy slit.

Then, he reached around me to unhook my bra. Taking his time, he removed my bra straps from my shoulders. Then, he removed my arms from my bra straps while I held my bra cups in place. Finally, I removed my bra and tossed it on his bed. He stared at my naked breasts as if he stared at his mother's naked breasts.