My VideoChat Error Ch 31

My life seems so complex.

I am being blackmailed.

I have a boyfriend.

I have a girlfriend.

I have a wife.

Who apparently is a domme.

She has a boyfriend.

She has been cuckqueaning his wife

She has been cuckolding me.

My penis is in a chastity device,

I am being feminized.

I seem to be more Shauna than Shaun with all of them.

Except when at work.

Monday afternoon.

2 pm.

As I stood there in the hallway outside of the conference room I suddenly could feel all the lingerie I was wearing underneath my man clothes. I could feel my lingerie clinging to smooth skin of my hairless body. I was clad in pink today - lacy bra and garter belt, cotton panties and sheer stockings.

I was glad that no one could see through my business suit.

That would have been humiliating.

Very humiliating.

I was glad I still felt that way.

John Harding and my boss, Terrance, were in the conference room chatting. I had been lost in thought when I arrived for our meeting to see what John Harding and his company thought of our proposal. John and Terrance were reliving the old days so I stayed outside and kept my train of thought going,

This past weekend, heck this past week, threw me for a loop. Let alone the past month. I was thinking back to Friday night when I was at the bar with my boyfriend, done up as Shauna. I could feel him holding me with his muscular arms while we danced slowly. His large bulge pressed against me. I could feel the same muscular body as he draped over me while frantically fucking my ass in the staff room of that bar.

My breathing picked up.

My penis began to fill my cage.

Suddenly images of Saturday night came to mind. Of my wife Emma being pleasured by her boyfriend Jacques' large, thick cock. Of his flat chested wife, Teri, wearing a steel chastity belt, not allowed to get off while her husband fucked my big breasted, blonde wife Emma. In our marital bed. Of Teri seeming to be arousal at all of this.

I was breathing faster.

My penis got stiffer.

Of the revelation yesterday that Nick would continue to fuck Denise. My girlfriend Denise. Of learning that I would be attending Emma's company picnic on Saturday at the home of her boss, Dave, the man who has been breeding my wife. Of—

A young secretary, with her brunette hair tied back in a ponytail suddenly passed me by as I stood there a few feet from the mostly closed door.

My face felt flushed.

My breathing almost shallow.

I was glad she could not read my thoughts.

"Good afternoon Mr. Jacobs," she said with a smile before taking some coffee into the meeting room.

"Hello," I replied as I smiled back.

She left the door open behind her as her hands were full.

"I'm glad you have a man for the lead. There should be at least one man in the room when anything is discussed," John Harding stated. Their conversation was harder to tune out with the door much more open now.

"I concur," my boss Terrance said with a bit of a huff.

"Thank you Ellen," he mentioned to the young girl.

"You are most welcome Mr. Jones," the brunette secretary replied cheerfully.

Ellen smiled again as she passed by me on her way back to the Vice President's office. Ellen was Vanessa's secretary. At the last minute Terrance decided to leave Vanessa out of this meeting as he said that John Harding preferred doing business with men than with women. To say that Vanessa was not happy was a total understatement. She had put a lot of work into our proposal. More than me in fact. But she bit her lip and stayed in her office.

More like fumed in her office I figured.

"So I hear that a woman is heading up the project on your end. That's new for you John," Terrance said bluntly.

"Yes, my wife insisted that Rachael get the lead," John replied.

His wife insisted? Why?

"Your wife is involved in the company now?"

"Yeah, about six months or so ago she decided she wanted to take a more active role in our company. Since she technically owns half, it has been hard to keep her happy and work around it. Rachael has helped in that regard. Rachael—"

Just then Rachael arrived. I lost my focus on the conversation in the room and focussed on my former secretary.

My hot looking former secretary.

She was clad in a baby blue blouse and skirt that looked great with her long, red hair and green eyes. Her heels were also baby blue and contrasted well with her much darker blue stockings. She looked so amazing in that outfit.

Part of me wished I did not have to fire her earlier this year. She had been a good secretary. But then I would not have needed to hire Denise. Well, actually, then the company would not have hired Denise to be my secretary, And that was after I had several temps.

Rachael looked at me with a bit of a scowl on her face.

"You're waiting outside? Why?" Rachael asked in a demanding and more than slightly condescending voice.

Her lips looked so luscious coated in red gloss lipstick.

Much like Denise's often looked.

I was taken aback by her commanding presence and by her snippy comment. I had not known what to expect. I thought she might be not the happiest to work with me, but I did expect that she would at least feign professionalism and appear friendly towards me on the outside.

I certainly did not expect her to come in like a harpy.

My heart sank.

It did not bode well for our proposal.

"Hmm?" Rachael added impatiently and with some disdain as I had not responded to her yet.

"Well, I could hear that they were having a conversation, and I thought I might interrupt it," I stammered out still taken aback by her.

Rachel rolled her eyes at me, turned and strode into the conference room.

I followed her.

"Here is Rachael," Mr Harding said. "She is the great asset to our company that I told you about," he added.

"I certainly hope that John only had good things to say about me," Rachael stated with a professional smile as she reached her hand out to my boss.

My boss took it and shook it.

"Yes he did. And my, you look just as lovely as I had also heard," Terrance complimented the hot looking redhead.

She just smiled in return. I thought I caught a glimpse of an 'I am more than just a pretty face' look on her.

Or maybe I just imagined that.

"And this is Shaun," Terrance said as he introduced me.

I followed suit and shook Mr Harding's hand.

"I am honoured to be meeting you in person Mr. Harding," I said.

"You can call me John. I have been hearing good things about you, and not all from your boss or Rachael," he replied with a slight wink.

Good things from Rachael?

"You always were one to check out your dance partners before offering them your hand," Terrance said with a chuckle.

Mr Harding chuckled a bit too.

"I know you two know each other, so no introductions needed," John Harding said as he looked from Rachael to me and back to Rachael.

"Shall we begin?" Rachael asked sounding very professional and not at all warm.

We all sat down. Us on one side, them on the other of the heavy, oak boardroom table. It was wide and a bit taller than most tables. I think it was bought to seem a bit intimidating. I heard that the first CEO and most of the board were rather tall and large.

Or so the story goes.

They had their folders of documents and we had ours. Both Terrance and John were old school. We brought files to meetings, not laptops. It could have been a long meeting.

Fortunately or unfortunately, that wasn't going to be the case.

"Let's cut to the chase," John said. "We like your proposal."

A broad smile spread across Terrance's face.

"But," John Harding started and stopped.

"But what?" Terrance said sounding a bit concerned.

"Is Shaun the man you want to head up your end of the project?" John Harding asked with a dead serious look on his face.

"Yes, he is our man," Terrance replied. "Why do you ask? You just said you heard good things about him?"

"As you know, Rachael will be our lead. That's not changing. That may be a conflict, knowing their history."

Terrance looked like he was broadsided for a second or two before his poker face returned.

"You knew he was our lead for this awhile ago. We have the best proposal and you know it. You wouldn't have come all the way over here if you did not think so."

John and Terrance looked at each other for a long moment.

"You are right, it is very good. I was hoping to see better chemistry between Rachael and Shaun in person though. I might have been mistaken in that regard," John stated flatly.

"Shaun has assured me he can work with Rachael," Terrance stated confidently. "I assume Rachael is just as professional as he is."

"Seeing them here, together, today, has me wondering," John Harding replied.

"Well what do you suggest? We are both here, ready to shake hands on the deal. I would not like to think that we both wasted our time," Terrance said.

They both looked at each other for another long moment.

"Maybe they just need to talk it out. See if they can find a way work together. Not just work together, but work well together. They would likely be more candid if we left them alone to do that don't you think?" John Harding mentioned.

"Ok. We can go upstairs to my office and have a few drinks, go over the old days some more and let them get re-acquainted again. I even have some scotch in my office. Old scotch. What do you say?" Terrance suggested.

"That would be good," Rachael chimed in still wearing her professional smile.

"Can we talk openly Shaun?" she asked as she gave an almost icy stare to me.

"Um, yes. Yes we can," I said as confidently as I could.

"Then lets be off," John Harding said.

John and Terrance got up and left the room, closing the door behind them.

Rachael turned to me. The cold look I had seen hints of had not left her eyes.

"So, I realize that things might be a bit rocky since I fired you and —" I began.

"The party," Rachael interrupted and paused.

My eyes opened wider. Why was she bringing that up here?

"You were there as a feminized cuckold. I know that Naughty only invites certain cuckolds with their wives. Naughty is very choosy. John Harding gets in because it's his mansion and his wife wants him there, as her cuckold. It's part of their arrangement with Naughty that gets the party to be hosted there," Rachael explained.

A truly professional look returned and replaced her cold expression.

"What are you getting at?" I asked more than a bit confused and trying to find my footing.

Rachael hesitated. She sat up straighter and leaned forward towards me. Her pretty green eyes bore right into me.

"Ok, lets cut the crap. All I care to know is if you will submit to me sexually. And more. If so, then we can work together. Nothing else will get in the way. It's a good project for your company and we don't have your expertise. But if that arrangement does not work for you, then we will pick a different proposal. Period." Rachael stated assertively.

It was my turn to hesitate. I did not know what to say. I did not have a good poker face. I was sure Rachael could see that she had taken me aback.

Terrance and the board wanted this contract.

I needed this contract.

A smile broke across her pretty, glossy, red lips.

"I know that you are sexually submissive. I know that you like cock. And dressing as a woman/feminized or at least being trained to like it or Naughty would not have picked you. I like sexually submissive men. I like fucking their asses. And more. That brings me deep sexual satisfaction. I get off on it." Rachael declared.

My penis was stirring in my chastity device unbidden.

Again.

I thought back to when she had come on to me as my secretary. She had only mentioned wanting my penis. Wanting me in her. Wanting my seed. No mention of her, me and a strap-on, or?

"And how does this relate to our proposal?" I queried more meekly than I had intended. At least I had found my voice though.

Rachael smiled once more.

She then licked the inside of her upper lip a bit.

Her eyes sparkled again.

"If you agree between us to submit to me during our contract, I will ensure your firm gets the contract," Rachael stated.

I gasped lightly. I was not expecting this.

My heart began to beat a bit faster.

No, more than a bit faster.

"Yes?" Rachael pressed.

"I have to submit to you sexually. Can we negotiate that?" I asked quietly with my head tilted down towards her.

"No Shauna," she replied with a wicked looking grin. "What else would interest me," she semi-asked rhetorically.

My career seemed to flash before my eyes. Terrance telling me how important this project was to our company. Vanessa wanting the project lead instead of me. My upward trajectory in the company. The importance of getting this right. To me in this company. Of having my own office. Of having my own secretary. Of me making good money. Of-

"So?" Rachael queried.

I had been lost in thought.

My hands had become sweaty.

My heart was beating even faster now it seemed.

My mouth was dry.

I needed to make this right.

How could I given my situation?

"I have to talk to Naughty first," I explained.

Rachael was still looking directly into my eyes.

"Oh, so you are one of Naughty's subs. Even more interesting," she said with a knowing grin.

I looked away from her stare and down at the floor.

"Contact Naughty. I will go freshen up and tell the men that we need more time to work things out," Rachael said firmly as she rose from her chair.

The men?

Was I not a man?

She straightened her skirt. She looked at me like I was her butler. Or maid. Then walked past me.

She was much more confident than when she was my secretary. She also had an air of being in control.

Like Miranda.

But colder my gut told me.

Well, at least towards me I surmised.

I heard the clack of her shoes on the hardwood floor as she walked purposefully to the door.

I picked up my phone. I hoped that Naughty would be able to respond. We had to get this contract. I had to get us this contract. I was feeling a bit shaken, if not a bit frantic.

As I began to text Naughty, Rachael exited the room and closed the door behind her. I explained what Rachael had wanted.

Sent.

I waited.

One minute.

Two minutes.

Three minutes.

Four minutes.

Five minutes.

My heart was racing now. I needed to get ahold of Naughty.

Six minutes.

Seven minutes.

Should I contact Miranda and ask her to get Naughty for me?

Eight minutes.

Message read. I breathed a little bit better.

Naughty was typing.

"Are you willing to submit to Rachael?"

I was taken aback by a question rather than an answer. And by that bluntly pointed question at that.

My heart began to race again.

It sounded like I was not just going to be tasked with worshipping Rachael's pussy. Did Naughty know something I did not know?

I had needed an answer. Now I had to answer.

"Yes," I reluctantly typed.

Immediately Naughty began typing something more.

"Rachael is good at breaking husbands. She can help with your training, in fact she will be the next part of your training." Naughty typed. "Submit to Rachael when you are with her. Miranda will talk with her. Chat later."

Breaking husbands? What could that mean? Did she do that to John Harding?

I felt so nervous.

Next part of my training? Was Rachael to be part of the plan before I even asked?

I sat there for a few minutes mulling over what I had just agreed to. Mulling over what might happen.

My penis began to stir again for some reason.

The door opened and Rachael came back in.

Good timing.

I would not have the time to continue pondering these thoughts.

She strode back in and came over to my side of the table. She sat down and crossed her stocking covered legs.

Man did they look good in her dark blue, sheer stockings with four inch light blue pumps. She was just as good looking as when she was my secretary. She wore more expensive clothes now though. John Harding must be paying her well.

"So what did Naughty say," Rachael asked looking me directly in the eyes.

I drew in a breath.

I was about to submit to this dominant redhead.

I had butterflies in my stomach. And it was knotting up at the same time.

Rachael looked at me expectantly yet confidently.

"Naughty agreed that I can submit to you," I stammered out.

A wicked smile broke across her face.

Her eyes sparkled.

"Naughty said that Miranda would talk with you," I managed to add.

My phone dinged.

I looked at it.

Jason.

His message was something about tomorrow night. I would have to look at it and get back to him later.

"More from Naughty?" Rachael queried.

I guess I did not have to tell Rachael about him now. But she would find out eventually. Better to get it over with.

"No, it was my boyfriend," I admitted feeling very embarrassed at telling a hot looking woman that.

"Boyfriend. I was not wrong about you. Miranda too. You are one lucky or unlucky girl. Now prove your worthiness to me if you want the deal to go through," Rachael declared firmly with a hint of arrogance as she uncrossed her legs.

I sat there a bit dumbfounded.

Did she really mean for me to service her here?

Now?

"On your knees Shauna," Rachael commanded.

"Huh?" I uttered. This whirlwind turn of events had me reeling.

"Was I not clear?" Rachael asked with a hint of anger in her voice.

I got off my chair and onto my knees in front of Rachael.

"If you want to submit to me, you need to ask."

I looked up at her.

She seemed so dominant sitting there in her boardroom chair, dressed so smartly.

Part of me felt so aroused for some reason.

My penis was confirming that.

"Miss Rachael, please let me submit to you. I will do whatever you ask," I said plaintively.

Rachael looked down at me and likely on me.

Her wicked smile was back.

"I accept your submission," she said huskily.

Rachael hiked her skirt up to her waist revealing lacy garters attached to the top of her stockings. And milky white flesh above them.

"I need servicing. Great servicing," Rachael clarified.

My heart began to race again.

My penis stirred in its cage.

"Here and now?"

"You are questioning me already?"

I was so nervous. We could get caught. I had agreed to submit to her though. I knew I had to do what she asked.

"Maybe this deal won't work out," Rachael stated.

I started to move forward to do her bidding.

"No, get up and bend over the table. You need to learn your place Shauna," Rachael commanded.

I felt even more anxious. Was she going to fuck my ass right here? Right now? She would see my lingerie, my butt plug, my chastity device. I would be even more humiliated.

My breathing picked up.

My heart was racing still.

My penis betrayed my arousal.

Nervously I did as I was told.

Rachael came up behind me. She reached around my waist and unbuckled my belt and undid my pants. She pulled them down to my ankles.

"Nice lingerie Shauna," Rachael declared almost derisively.

"Nice pink lingerie. The right colour for a girl."

She pulled my panties down as well.

"Nice. Very nice," the hot red head said as she stood back and gazed upon my rear end. My butt plug and chastity cage were now fully on display for her.

She reached under and caressed my locked up balls.

"Nice but small," Rachael declared and squeezed them a lot more than just a little.

I winced in pain. I gasped and leaned instinctively into the table.

Small? Why does every dominant woman say that?

She laughed a little at my discomfort and released them.

She then took hold of my butt plug and twisted it around a little.

That made my ass quiver.