My VideoChat Error Ch 23

Trapped.

Earrings.

Lingerie.

Butt plug.

Chastity device.

Girlfriend.

Boyfriend.

Cuckolded.

Everything that had happened recently had built this feeling up in me. All I could think about was how trapped everything has made me feel.

I am not in control.

"Hold still, almost done," Denise said, breaking my train of thought as she peered intently at the eyeliner she was applying to my second eye.

Oh, and by my makeup.

Denise has been training me to apply my own makeup so I could truly appear as Shauna to the world. Tonight however things needed to be perfect. It was my first date with my boyfriend Jason.

Yes my boyfriend.

My forced boyfriend.

The nervousness and anxiety had been weighing on me all day.

The butt plug that had been vibrating away in my ass since 9 am, mostly on setting 2 didn't help. That and the penis cage which kept my erections in check, were constant reminders of my blackmail situation.

I was to satisfy my man.

As a woman.

My stomach was twisting up again.

My penis was trying to grow in it's locked cage.

It couldn't.

It was trapped.

Just like me.

Again I felt every piece of lingerie on my body, the wig on my head and the makeup on my face.

And the new earrings in my ears.

This morning my wife Emma complimented me again on those same earrings, before reminding me to keep them clean.

"They look so good on you, you are sure to turn your boyfriend on," she had complimented me with a knowing smile and a twinkle in her eye.

Like we were two girlfriends chatting about our men.

That felt so weird.

Later, when holding me tight and hugging me goodbye, Emma whispered naughtily into my ear "You're going to have so much fun with your man tonight." Then she planted a warm, wet kiss on my lips and with a twinkle in her eye, sent me off to work.

My wife seemed so cool with me being out overnight. With me being out with a man. A Real man. As a woman. Knowing what we would be doing.

Almost like she wanted it that way.

No matter what, it still felt awkward, even though she had made it a bit less so.

At work Denise seemed oddly excited by my upcoming date too.

"Ready for your big day? Er night, as it may be?" She had greeted me gleefully with a wide grin.

That put me off kilter.

I hesitated for a second, then I smiled in return.

Denise had followed me into my office as usual, and very eagerly helped me shed my man clothes for our video chat with Naughty. The chat was short with Naughty spelling out what I needed to do, well more like reiterating how I was supposed to act. Naughty left the exact deeds up to me. The day was already feeling kind of surreal.

Denise must have sensed the apprehension I felt. After we finished our morning video chat with Naughty behind closed doors, Denise was supportively affectionate with me on my leather couch.

When she kissed me she seemed more like the Denise I knew. The affectionate, caring woman who was so much more than eye candy. True she was a 10. Brunette, average height, ample cleavage, super pretty face with blue eyes, perfect makeup, gorgeous red-nailed fingers, and as always impeccably dressed: feminine light blue blouse, navy blue pleated skirt, navy blue stockings and heels. But to me she was so much more than met the eye.

After several minutes of making out, Denise broke our embrace, took my hands in hers and tilted her head forward a bit.

"Whether you want this or not," Denise began "its going to happen. You can either hate every minute of it or make the best of it. You might be forced but you may as well allow yourself to enjoy it," she added in a slightly resigned yet cheerful voice.

Enjoy this? I wasn't going to enjoy this.

I didn't want this.

I knew that I could contact Naughty and ask to not have to take a boyfriend. But if he/she allowed it that would break our deal and gang bangs for Denise would be back on the table.

That I couldn't accept.

I didn't want this but I had to do it for Denise.

My Denise.

Trapped.

Something felt off, or was it just me? Nevertheless, my protective feelings for her swept over me. I felt my resolve again.

I would do anything for my Denise.

When I didn't rebut her comments she continued.

"Do exactly as Naughty said. Submit to his cock. Give yourself to him. Surrender your ass to him willingly. Eagerly. Be his woman. Passionately do all the slutty things he always dreamed of," my hot brunette secretary whispered huskily to me. Her eyes seemed to sparkle and her enthusiasm seemed to be oddly high.

'Surrender myself to him?'

'Eagerly?, willingly?'

Those sound like Naughty's words.

Miranda's words.

Even perhaps Emma's words.

Why was she telling me this? And so eagerly herself?

Her tone of voice.

Her mannerism.

Her choice of words.

The look in her eyes.

What has happened to Denise?

My head felt like it was spinning.

I felt like I was in another dimension.

The small knot that I had felt in my stomach filled it and became very tight.

Denise did not seem like Denise.

My Denise.

Then she proceeded to kiss me tenderly several times.

Has she maybe just given up hope?

or

Did she want-

"You will be more convincing if you are eager and you will turn him on much more. You need him wanting more from you to keep Naughty happy," Denise added. Then she continued kissing me.

"Besides, this won't last forever. We will get out of this. Together. Might as well see the glass as half full rather than half empty," she added before pressing her luscious, wet, lipstick covered lips to mine again.

Any apprehension I felt from her seeming eagerness melted away with that hot, hot kiss.

She was right.

Not only did I have to pretend to like it, I would have to turn him on.

A lot.

Turn him on with my lingerie, makeup, wig, earrings and by how well I performed. I would have to be eager, willing and wanton.

I would truly have to 'perform' to be all that.

I didn't want a man, but he had to truly believe that I did.

The knot that I had in my stomach tightened and turned over.

Could I really see the glass half full?

To allow myself to enjoy it?

I shuddered at that thought.

"Done!" Denise announced as she pulled back to get a better look at me.

The memory of our conversation from earlier today faded as I snapped back to the here and now.

The knot in my stomach was still there though.

Not a memory.

I turned to look at the mirror.

Once again a beautiful brunette was staring back at me.

She had curly, shoulder length brown hair. Pretty eyes framed by dark eyeshadow and curled lashes. Reddish blush and bright red lipstick highlighted her face. Her white stud earrings glistened in the light. She wore a white blouse open just enough to reveal the white, lace of her bra.

White lingerie.

Just like a virgin bride.

Emma's choice today. Instead of the pink she had been picking up to now.

I breathed in sharply at the woman's beauty as if I had never seen her before. As I did I saw her chest rise and fall. As I did I felt the lacy bra clasp onto my chest.

I was her.

I had truly become Shauna again.

Not just in name but in look.

My penis tried to get hard but instead filled my cage. I noticed the vibrating plug in my ass. Every fibre of my being seemed to come to life.

I shifted in my chair and felt the sheer white stockings on my legs. They tugged lightly at my garters. Instinctively I adjusted my white pleated skirt to cover them with my red nailed fingers.

Instinctively.

I was getting used to being attired as a woman,

That sent a shiver down my spine.

The full weight of what was going happen tonight hit me once again as I looked at the hot brunette sitting in front of the mirror.

I was going to copulate with my boyfriend.

As his woman.

Rather, he was going to copulate with me.

The other hot brunette, the one standing behind me rubbed my shoulders. She could sense my apprehension.

Again.

"You'll be fine," Denise reminded.

"He will treat you like the lady you present yourself to be Shauna. The lady that you are as Shauna," she added.

The lady that I 'am'.

Denise was confusing me again.

"He is taking you to a nice cozy dinner spot. I have been there. If he treats you well there, he will also at the motel after. It's out of your hands so relax a little. Enjoy being the one wined and dined. Let him take the lead and make you feel special."

"Then I make him feel special later," I added. My stomach churned once again at the thought.

My penis stirred.

Denise cracked a bit of a smile.

"Exactly."

"Now, he should be here any minute. Let's get your heels on and make sure your purse and overnight bag have what they need," Denise instructed.

I would have to do my best to turn him on, to make it special for him. Even if sex with a man was not my thing.

Images of me making my boyfriend feel special sprang to mind. I imagined his big black cock in front of my face. The feel of its soft skin as I stroked it. I could smell it's musky odour as I leaned forward to take it in my mouth. The weight of it on my tongue. I salivated as I tasted his seed in my mouth. Then I felt his strong hands holding my hips as he thrust himself into me.

"Shauna," my Denise was saying as she stepped in front of me and took hold of my shoulders. "Did you hear what I said?"

"Huh?"

"You zoned out. Remember to text me when you can and tell me about dinner," Denise's luscious red lips said.

"Yes, yes I will," I replied.

I realized I was breathing harder, faster.

Even though Denise shut off the vibrations in my ass, my penis was straining in its cage.

I shuddered inside at that realization.

Just then my phone dinged.

He was here.

My heart leapt into my throat. I was actually going to go on a date with My boyfriend.

Yes My boyfriend.

I shuddered at that thought.

My penis still strained in its cage.

My ass clenched my buttplug.

My stomach filled with butterflies.

"It'll be fine, it'll be fine," Denise repeated as she escorted me to the entrance of the apartment building.

Denise took me by the hand, our fingers interlaced and led me towards my evening.

Even though it was not my first time going out in public as Shauna, it might as well have been. I felt just as nervous. Every fibre of my being felt alive. I felt every piece of white lingerie that clung to my body, from the sheer stockings on my legs, to the lacy garter belt that kept them up, to the lacy white bra under my blouse.

I felt as though every eye was on me as we exited the apartment. That everyone knew that my painted face was actually that of a man.

My red lipstick tasted so strong as I bit my lip.

My penis strained in its locked cage in my panties under my skirt.

My ankle twisted a bit in my heels as we stepped out the front door. I realized again that Denise was holding my hand as she squeezed it and tugged me to a stop.

"Calm down, take your time. You can do it. You will be fine," Denise reminded me with a reassuring smile.

"You've got this," she added confidently.

I looked up and saw a large black man leaning on a modern day Mustang by the curb at the end of the walkway. He smiled as our eyes met and waved at me.

It was Jason.

My boyfriend.

I felt my penis try again to get hard and my ass clenched onto my plug as I walked. Several young men were looking at us and smiling.

"They wouldn't be gawking like that if they didn't see two hot looking women," Denise whispered assuredly to me with a smile.

Denise led me down the walkway towards my waiting man. Ironically it was much like being led down the aisle to the altar. I was even wearing white clothing and lingerie.

Just like a bride.

"Good evening ladies," Jason greeted us as we neared his Mustang.

He was dressed as sharply as me. A black blazer hung from his broad shoulders. He had a white dress shirt on, unbuttoned at the top revealing his well developed chest. Black dress pants and black leather shoes rounded out his look.

It didn't hide the bulge in his pants.

My eyes kept going back to his manhood.

I salivated as I tasted his cum in my mouth.

My stomach twisted a little at that thought.

We said hello in reply. I cracked a slightly nervous smile.

When we got closer he took my right hand from Denise, raised it to his lips and planted a light kiss on it.

I blushed and looked down from his eyes.

I felt so submissive in that moment.

"And who is this pretty lady Shauna?"

"Uh," I began in my best girly voice. "This is Denise."

He then turned to her and kissed her hand as well.

"You didn't tell me he was quite this charming Shauna," Denise mockingly admonished me with a smile and a girly giggle.

He chuckled deeply in response. "I am always a ladies man."

"Shall we Shauna?" he asked as he moved to open my door.

I could have thanked him for his time, turned and gone back to Denise's couch. I would not have to go out as this man's date. I would not have to satisfy his carnal desires.

Then Naughty would force me to pick a different boyfriend. Maybe one not so seemingly gentlemanly. Or worse and say that I reneged on my part of the deal and...

I felt embarrassed.

Naughty had not given me this man, I had chosen him. Naughty had forced me to pick a man, but made it my choice of man.

My choice.

My stiff penis had betrayed me. Looking at pictures of Jason and his thick manly cock and I became hard. He was an obvious choice.

Even now my penis was straining in its locked cage. I felt my pulse on the plug in my ass.

I felt ashamed.

I felt just as trapped as my penis.

The knot in my stomach twisted and I felt butterflies as well.

"Yes, lets," I replied femininely.

"Cheer up and have fun," Denise whispered to me as she gave me my goodbye hug by the car. "You will, but only if you let yourself, only if you allow yourself too," she added with a chipper sounding whisper.

When we broke our embrace Jason took me by the hand and helped me into his car. After he closed the door I noticed that Denise was still standing there. With a wink, a little wave and a girly smile she turned to go.

I glanced around and saw that several young men were still eyeing Denise.

And me.

As I shifted in my seat my butt plug felt so big. My ass instinctively clenched on it. My penis still wanted to be stiff. I looked at one of the men openly smiling at me behind the closed door of a real man's mustang, then-

The driver's door opened and broke that train of thought. Jason stuffed his large frame in.

"You sure are an attention grabber Shauna." He noted with a friendly smile. "I am one lucky man," He added sounding a bit nervous.

He turned the key and the engine hummed to life. Before I knew it we were several blocks away, then more. Neither of us spoke at first. It was awkward. Then he made light small talk.

We pulled into a parking lot and found the last spot several rows over from the door.

We parked and were flanked closely on both sides by raised suspension trucks.

As I peered straight out the window.

They seemed like walls.

On both sides.

Walling us in.

Together.

As Jason turned off the engine he turned to me.

"Look Shauna, as you could maybe tell from my voice, I am a bit nervous about this. Well more than just a bit nervous. I want this to go just right. I want you to know what type of man I really am, and hope you like who -"

"I am nervous too," I interjected and breathed a bit easier. It felt like we were two kids out on their first date. "I want this to go well too," I added.

He breathed his own sigh of relief and took my left hand in his right. I saw my red nailed, white skinned fingers disappear into his larger, masculine, black hand.

His hand engulfed mine.

I felt so feminine to be taken like that.

I felt so odd inside.

Jason gently held my hand for a few moments then he got out and like a gentleman, opened my door for me.

Fresh air blew into the car.

A much needed breath of fresh air.

Sometimes the small things in life make all the difference.

Surprisingly I felt less anxious.

The gentle breeze also blew over my stocking covered legs as Jason helped me out of his Mustang. My upper inner thighs felt oddly exposed by the wind. I was getting used to having my legs constantly covered by stockings.

I was getting used to wearing sheer stockings.

Correction.

I was used to wearing sheer stockings.

That sent a shiver down my spine.

As I gained my footing on my heels, Jason took my hand in his again. His face beamed as we walked hand in hand to the restaurant. Several people looked over at us, but went back to what they were doing.

Still I felt as though everyone was looking at me. That everyone knew I was really a man.

I blushed constantly.

I felt my butt plug in my ass with every step I took. My penis was having trouble in its cage again.

The place was dimly enough lit that it took our eyes several moments to adjust. When they did, I realized why he felt so open about being with me as a married man - the clientele was mostly mid 20's.

The blonde hostess seemed to be sizing us up. Her smile seemed genuine though.

"Do you two have reservations?" She queried politely.

"Yes, under Jason," He replied.

She looked down at her list. "Ah yes," she said momentarily. She grabbed two menus and began to turn to her left. "Right this way," she said continuing to smile.

Once again I blushed as I felt that all eyes were on me. I realized though that most just glanced. No more.

A big black man with a white "woman", and we barely were noteworthy. Then I realized, there were several interracial couples. And I was sure that I saw several "women" as well. This was definitely not his wife's crowd, nor that of her friends.

My stress level dropped several notches.

We had a booth.

It's closed in nature seemed comforting.

I hadn't noticed my butt plug as much in recent days. Now I was constantly aware of its presence in my ass. Especially as I slid into the booth.

When we sat the hostess left us with menus saying "Your server will be with you shortly."

I was perusing the menu and trying to decide what a lady would order when Jason spoke up.

"I'll take a beer," he said.

I looked up and saw a waitress, whom I did not hear approach our table, turning towards me. She was young, blonde and wore a pleasant smile on her face.

"And for you m'am?" She asked without hesitation.

M'am. She called me m'am.

She was fully accepting me as a woman. I felt weird inside. Weirder than I already felt.

"Ummm," I responded after a bit.

She just smiled pleasantly and waited patiently.

"A vodka and sev' please," I finally managed to say in my best girly voice.

She nodded, wrote it down and trotted off.

There was an awkward silence as I just stared at my menu.

"What looks good to you?" I started in order to break it.

"Hmmm," he replied tilting his head. "I am leaning towards the roast chicken. You?"

I looked down at the menu again. I had not expected his reply even though anyone with half a brain would.

"The chicken salad I guess," I stammered out.

I would have liked a steak but knew that a girly salad would better suit Shauna.

Just then our drinks arrived and we placed our orders. We made some small talk until our food arrived. We both began to feel more at ease. That and he had another beer and I had 2 doubles.

I needed them.

We made conversation throughout dinner. To my surprise he was interesting to talk to. We really hit it off. I had not thought about that when I was forced to pick a boyfriend. I just thought of the sexual aspect. I did not realize that he might actually want more.