My VideoChat Error Ch 16

"Come," Denise suggested as she took me by the hand and began down the stairs.

I felt so feminine walking in my lacy lingerie with a skirt, blouse and accessories. So feminine. Every fibre of my being was alive. I expected everyone would look at me. Everyone would see a man wearing woman's clothing. My face felt flushed. I felt so ashamed. I felt like I was in a trance.

Both Denise's and my heels clacked on the stairs. To my amazement I walked much better than before, even going down stairs in heels. It was becoming part of me to walk as a woman in heels.

That sent a chill down my spine.

As we approached the landing by the front door, a thirty-ish man entered. He was casually dressed in jeans and a t-shirt. Average height and build with light brown hair.

His eyes washed over my body. I felt so embarrassed walking in woman's clothing.

"Hi Denise," he said with a smile as he turned his gaze to my companion.

"Hi Leonard," Denise replied with just as friendly a smile.

"And who is your friend?" Leonard asked was he sized me up from head to toe. My heart began to race. My embarrassment climbed to another level.

"This is Shauna," Denise mentioned as she nodded her head towards me.

Butterflies welled up in my stomach. Now I had to meet people as Shauna. Not just in name, but in look as well. I was truly becoming Shauna.

"Hello Shauna," Leonard stated as he extended his hand to me. Instinctively I shook his hand with my right. The two bracelets that matched my red nails clattered lightly.

"Hi," I mustered in my best girly voice in response.

He looked me in the eye and smiled warmly.

I felt so embarrassed. I knew that I was blushing, even if the makeup likely covered it up.

"We should get together for coffee sometime," Leonard announced as he turned back to Denise. "And maybe you would like to join us Shauna," he added with a smile to me.

"Yes, that sounds good," answered Denise for both of us. "Have a good evening!" she added as she turned and continued down the stairs, pulling me along behind her. I managed a slight smile as I passed by him.

"See you both later," Leonard replied.

A wave of relief washed over me as we got to the bottom of the stairs. Denise leaned back to me a little.

"You see? Nothing to worry about. Leonard accepted you as Shauna," she whispered loudly to me. "He even was hitting on you," she added with a giggle.

When Denise opened the door to the small underground parkade another rush of air went through me. Over my stockinged legs and under my skirt. It felt cool and gave my legs a silky, sensual feel.

The parking stalls were tight as it was not a big building. Four stalls on the front wall and two by the entrance by the back wall.

"I am lucky to have one of the underground stalls. I feel safer in here at night than in the parking lot out back for the rest of the tenants," mentioned Denise. We got into her car and soon we were passing by the back lot and into the alleyway. Afterwards we passed by the front of the building.

I felt so relieved that I didn't have to go out the front door dolled up like this. I thanked Denise for not making me walk the two blocks to the coffee shop. She smiled and squeezed my hand in reply.

Traffic was light and before I knew it, we were parking right by the door. The coffee shop was a large place and we picked the dim lit corner I had told him to meet me at. At least I had the luck that neither the tables there nor the leather easy chairs and couch were occupied.

There were a fair number of people there. Several looked our way. Yes, two women in skirts and heels usually do draw attention. Attention that I did not want.

Again I felt so embarrassed. Again my face felt so flushed. My heart had leapt into my throat when I had stepped out of the car and out into the public for all to see. Now I felt it thumping away in my chest under my bra and blouse.

I felt as though every eye was on me. That all would know I was a man in drag.

I looked down and avoided the gaze of the men we had to pass by to get to the far corner. Even then I felt their eyes on my legs and my skirt covered ass. I knew they would be looking at us, how could they not? I overheard one whisper "What hot legs they both have," and another quietly added "I wish I were with them."

My heart beat faster and I felt warm all over. I also felt flattered to my surprise. Luckily we were soon out of earshot of them and made it to the corner.

Nervously, I sat down on the leather couch. It felt cool on my stockinged legs.

"You're doing great," Denise commented as my heart began beating slower. But only a bit. "Stay here, I will get us something to drink. It will be ok."

Denise got us decafs then sat at a table nearby. My hands shook a little as I took a sip of the hot beverage. The men kept ogling us. I averted their gaze. I remembered why I was here and I started up an audio recording program on my phone and placed it in my slightly open purse. Naughty wanted to listen to the date. And likely record it for posterity.

Ugh.

Time seemed to go so slow. I was sure that those guys were still looking at us. A quick glance confirmed that. I began to wonder if they suspected that I was actually a man.

After a few minutes a black man entered the shop. It had to be him. My heart began to race again. He looked around, as if it were his first time here, then came over.

It wasn't him.

"Hey don't I know you from somewhere?" He began with a smile, obviously a bad pickup line.

"No, I don't think so," I replied nervously in my best girlish voice.

He sat on the same couch kind of close to me. He was obviously checking me out. I was beginning to feel scared. This was not part of the plan.

Suddenly he leaned over to me.

"Look, I'd like to get to know you," he began, "we could become-" he continued as he was reaching for my thigh.

I was mortified. What to do? I began to shake. How do I get out of this situation? How do I not draw attention to myself? At least not more than my look already has.

He didn't reach my leg as another man grabbed his arm. I looked up to see the man from the dating site.

"She's with me," he stated firmly. "I suggest you find some place else to sit," he asserted commandingly. I felt a wave of relief wash over me. The first one since I entered the coffee shop.

The first man looked up, startled. Then he withdrew his hand and got up to leave. My date stood firm and smiled a confident smile. He was built. The other man not.

As soon as this man was on his way out of the shop, the man I was here to meet turned and offered his hand to me. I smiled and reached mine out. To my surprise he didn't shake it, rather he gently took my hand in his larger one and brought it to his lips.

After he kissed it, he smiled and stated "My name is Jason."

"Shauna," I offered in reply in a bit of a shaky girl voice.

My stomach was full of butterflies.

"May I sit down?" Jason asked very politely.

"Yes," I replied about to get up.

He motioned for me to stay sitting as he sat down beside me. He turned to me and only half sat on the soft leather couch.

"You are even better looking than in your pictures, I am so glad we've met up," he said with a smile.

I sized him up without thinking about it. He was wearing a black business suit, with a white shirt and a red tie. His body seemed to be ready to burst out of it. His chest was broad and even his neck looked muscular. He had a friendly looking, clean shaven face and short hair.

"I played middle linebacker in college," he added as he noticed me checking him out.

"I'm sorry," I responded, "I didn't mean to stare." I said regaining my best girly voice and some of my composure.

"You look handsome," I found myself remarking.

"Thanks," he replied. "Look, I'm not good at this," he began. "I have never stepped out of my marriage. My wife does not like sex much anymore it seems, nor does she seem to want to go out a lot, other than social affairs to be seen at. What I need is someone who can satisfy my needs in bed and spend some time together. I'm not looking to get divorced, I just need someone to make my life complete. I hope I'm what your looking for."

I did not know what I was going to say either but I thought there would be more small talk first. I was glad I did not have to suffer through that. But then again, it would have delayed what I would have to say.

I felt so nervous. Like I was on my first date. His presence made me feel so - so not manly. I felt so feminine. So submissive.

"I," I began tentatively, "am also married." I added trying to gather my thoughts. I glanced down where my wedding ring should have been. I had taken it off as I always did when dressed as Shauna. I suddenly felt so naked without it.

"I too am lacking something in my marriage. I love my wife, but need something more," I paused. I really did love Emma. I really didn't want more. Images of my wife Emma flashed through my brain. My busty, blonde, good looking wife.

I wished I could be sitting on my couch, resting my head on her big, soft chest while watching some inane television show with her. Any television show. Like we have often done in our pyjamas. Her large chest looks so good in a bra but feels so pillowy when out of one.

"I need a man in my life, I need a man to worship sexually, as I declared in my profile," I hesitated as that was hard for me to say.

It was hard to hear me say.

The butterflies turned into a knot.

The next was even harder. "I need a man to satisfy me sexually, on a regular basis. Not as a man but like a woman. Something that my wife can't do."

My stomach churned.

This brought a big smile to his face.

"I also need discretion, as my wife can never find out," I added.

This felt so humiliating. So utterly humiliating.

"I do too," he replied. He then placed his large hand on my knee.

A shiver ran up my spine.

This was really happening.

The next part took all my courage. I reached out and put my hand on his leg in return. He smiled back at me. My heart began to race again.

Jason removed his hand from my leg, took my hand and placed it on his crotch. He had a nice sized bulge. It felt semi firm.

My face felt totally flushed.

"You like?" He said with a smile.

"Uh, huh," I mumbled softly, knowing that I had to.

"Would you like to see it?" He suddenly asked.

Things were moving so fast. My heart pounded in my chest. Another moment of truth.

"Uh, huh," I replied submissively not meeting his gaze.

"Let's go to my car." He suggested and reached out his hand to me.

"Uh, huh," I responded feeling the blood leave my head as I put my hand in his and let him help me up to my feet.

I blushed.

I glanced over at Denise who smiled and slightly nodded her head.

Unsteadily on my heals I let him lead me out of the cafe. A few of the other patrons looked me up as we passed by. Some smiled. That made me blush even more. The guys from before grinned knowingly as we approached. I looked down at my feet in shame.

Thankfully we got to his car fairly quickly. It was a modern mustang. He opened the door for me and folded the seat forward so I could get in the back. In heels it was more challenging than I had imagined. He stuffed himself in beside me. I placed my purse at my feet.

My heart was racing. I had just willingly gotten into the backseat of a car with a horny, hunky man. A thrill ran through my body at what might happen.

A thrill? My stomach turned in knots. I felt full of mixed emotions. Horrified at what might be about to happen. Thrilled by the obvious sexual tension.

"I have not done anything like this," Jason began with a smile, "since I was first dating my wife."

I readjusted myself in the seat as it was awkward to sit here in heels. As I did so I moved into him. He reached his arm around and in behind me and I wound up nestled under his left arm.

"Is this comfortable for you Shauna?" He asked politely.

"Yes," I replied nervously.

"I would be s bit more comfortable if you would help me with my belt buckle," he professed sounding a slight bit nervous himself.

He began fumbling with his belt with his right hand and I shifted a bit to reach across with my left. This pressed me even more into him. I could feel his muscularity through his clothes. he was truly built and seemed to be in as good a shape as he likely was in college. As I started helping him with my nailed left hand I looked up at him.

He leaned down and brought his lips to mine.

Both a chill and a thrill ran down my spine. I still was turned off by the thought of kissing another man. Really turned off. But Naughty was forcing me to do this.

I opened my mouth and let his tongue enter my mouth as I kissed him. Hesitantly at first but the more we kissed the more he got into it. I knew I needed to reciprocate so I forced myself to be just as eager.

At least his mouth tasted good. He had brushed his teeth before we met with a minty toothpaste.

After a bit more fumbling on both our parts, his pants were open and his mostly erect cock sprang out.

"I have needs. Can you satisfy them Shauna?" He asked quietly, barely pulling his lips from mine.

"Uh huh," I replied as lustfully as I could.

Immediately he guided my nail clad hand to his erection.

It felt very warm in my hand and I could feel it throb in my light grip. He was as big and about as thick as Mike Brown. His balls were as hairy as in the pictures.

He moaned lightly as I began to stroke him.

"Mmmmm, I like that," he moaned quietly as he resumed kissing me.

My stomach churned as here I was making out with this muscular man.

My penis was rock hard in my panties.

Once again it betrayed me.

After only a few strokes I could feel some sticky pre-cum on my fingers. He hadn't been touched like this in awhile. I could feel his excitement.

I broke from our kiss and looked down at his dark manhood.

I had to admit to myself It was a hot view. A neatly manicured feminine hand, replete with red nails was wrapped around a big, thick, black cock. And was stroking it.

My stomach still turned over as it was My hand stroking this man's cock.

"Your cock is so nice," I asserted huskily. I cringed inside as I said it.

"Your soft hand feels so good," he replied.

It was now or never, I told myself as my heart still raced. This man seemed like a not bad choice. I could definitely get worse.

I leaned over his big, thick cock. The muskiness of his manhood wafted into my nostrils.

I licked the tip of his cock. It tasted slightly salty from his pre-cum. He gasped then moaned in response. I kept stroking his now completely stiff cock.

I wrapped my lips around the large head of his manhood. I sucked lightly as I licked it. He moaned even more.

I began stroking faster and taking more of him in my mouth as I began to bob up and down on his big manly cock.

He moaned more and breathed faster.

"That feels so good Shauna, too good," he exhaled between moans.

He was almost ready to cum, I could tell.

Then all of a sudden his cock throbbed and his body stiffened.

"Uhhhhnnn!" He exclaimed as his cock exploded in my mouth. I slurped, sucked and swallowed as he kept cumming.

After taking his big load in my mouth i was still sucking on his manly cock when he lightly motioned me to stop.

"It feels sensitive," he explained.

"That was the best blowjob I have ever had," he said with a smile as he looked into my eyes. "My wife does not do that anymore."

It was definitely a fast one, I thought to myself.

I licked the dribble of cum from my lipstick smeared lips and smiled in return. His taste did not turn my stomach like I wanted it to. In fact his seed tasted better than most that I had swallowed.

"I would like us to start dating," he stated firmly.

This was moving fast.

My mind raced. I had just blown a man I had picked up through the internet. Naughty was forcing me to take a boyfriend. I didn't want one. I am a man. But made up like a woman. But, if I must have my own boyfriend - I guess he would probably be a good choice.

The man inside of me screamed no! Faintly. But I knew I needed to say yes.

"I would like that too," I replied. He drew me into his arms, we hugged briefly and I agreed to meet up with him next week and to take the ad down.

I had my boyfriend. That made me feel so weird. No, much more than weird.

Soon I was passing by Denise's apartment building and then back inside where she returned me back to Shaun from Shauna.

Just after she finished, I got a text from Naughty.

"Great job tonight. You are progressing well," typed Naughty. "You have now chosen a boyfriend that you can service and be satisfied sexually by," he/she added.

I could still taste his seed in my mouth. I knew I would be tasting it on a regular basis as I satisfied his carnal desires. But I would be satisfied by him sexually?

"Remember to have the kids looked after for the weekend as you two will be attending my party this Saturday," typed Naughty.

That redirected my thoughts. Party. More sex. Anal and oral. A chill ran down my spine.

"Yes all is set, " I replied.

The party. I had been trying to forget about that. Maybe I would get to meet Naughty? That thought perked me up.

My heart leaped into my throat. I had to find out.

"Will you be there?" I asked hesitantly.

There was a long pause.

"Yes," typed Naughty.

Denise's face brightened as we looked at each other.

"But I won't reveal myself as Naughty to you. Not yet," Naughty added.

Maybe not. He/she should be at his/her own party. Maybe I will at least figure out who you are I thought to myself.

Denise and I had no time to discuss this as I had to get home. We kissed and I left. As I was crossing the street to my car I noticed that a man in a parked car seemed to be watching me. I dismissed it as paranoia. Would I look at someone crossing the street after dark? Probably.

My thoughts returned to the event filled day and the upcoming party.

Would I meet Naughty at the party?

Would I know it?