A New Life Ch. 02

I closed my eyes and took a breath, which was far from easy. The steel boned corset, which I was made to purchase and learn to lace myself, was quite tight and pulled my body into the curvy shape that both Mistress Sally, and the men who have been encouraged to watch me on Skype, all enjoyed. The cursor moved across the screen as Mistress Sally's Skype call continued to ring, and I clicked accept. She immediately noticed my lack of makeup and was furious.

"You have to be kidding me, Cinnamon!" She yelled through the computer screen. "Not even a shred of makeup? Not even lipstick?"

"I'm so sorry, Mistress," I said, knowing full well that Mistress Sally was not going to accept my excuse. "Work kept me late. I didn't have a choice but to stay at the office and finish the day's project."

"Cinnamon, you know full well that I understand that life sometimes gets in the way of your ability to put yourself on display as I require, but this is the third time this MONTH than you have failed to be prepared at the required time," Mistress Sally responded.

I could only lower my head in shame. Shame that I had not feminized myself to her specifications. Which made my head swirl again. What was I doing? I'm essentially on call to this woman twenty-four hours a day and I have to be in a constant state of readiness to not simply be online, but be dressed to the nines as a sissy. A man decked out from head to toe in lingerie that would make a hooker shake her head.

"Fortunately for you, your punishment for not being ready will have to wait," Mistress Sally continued. "I have a busy night prepared for you, because I follow through with what I say."

"Yes, Mistress," I said meekly.

"There are a half dozen men lined up for your sissy performance tonight, Cinnamon. They all know all about you and have been sent a dozen or so pictures of you in your sissy bitch finest," she said with authority. "Each one of them has been given permission to splash your sissy ass...and face for that matter...across the internet should you disappoint them."

"Mistress! No!"

"No is not a word that is in a sissy's vocabulary, so I can only assume you are trying to be a man again. Is that why you don't have your make up on, you sissy tart? Are you a man today?" Mistress asked with a smile on her face.

"Mistress, I apologize for using words that are not meant for me." I once again lowered my head in shame.

"That's what I thought. Now, finish getting yourself ready, and if I get a single bad report from any of the men that message you for performances tonight, you are going to be quite the popular little whore at the glory holes next weekend," Mistress stated emphatically.

"Yes, Mistress Sally," was all I could mutter as I got up from my chair and hurried back to the bathroom. I could hear her muttering to herself as I walked away. She was clearly upset with my lack of respect by showing up partially ready.

I opened the top drawer and pulled out my small makeup kit. It had the basics from foundation to blush to lip liner and various colors of lipstick as well as eyeshadow to create that smoky eye look that I was still terrible at putting on. I took the liquid foundation and rubbed it all over my face. The slight color of my facial hair was immediately gone, replaced by wat appeared to be smooth creamy skin. I had been taught to start with my eyes and so I did. Using the various brush sizes to apply and blend the blues and greys to complete the look Mistress Sally wanted me to master.

As I worked on my eyeshadow, my gaze kept moving across my own body in the mirror. I wasn't allowed body hair any longer, and the corset managed to push my little A cups up and create a very real cleavage, especially as I bent forward and gravity did its part. The nipple clamps still held tight on my hyper sensitive nipples that poked through the fishnet bodystoking, and the little puff balls swayed as I moved my body. I finished my eyes and stood back up and looked at what I was turning myself into.

Long hair, makeup, black lingerie which included that damned corset that gave me a very real girlie shape, and garters and stockings that were all black with hot pink accents. I couldn't take my eyes off myself. What had she done to me? What had I done to myself? How did I allow her to get so much control of me? Just then, I heard the familiar sound of Skype again. The ringing signified my first audience member had arrived, and I still hadn't finished my makeup.

I moved back to the computer as quickly as I could in my high heels, bringing my portable mirror with me so as to continue making myself up as I talked to this man on the computer. I looked at the screen name and didn't recognize it. Good news and bad. The good is he was new and I could type and chat and buy myself a little more time...hopefully. The bad news was that I had no idea what to expect from him. He could be an admirer who just likes to see a sissy prance and pose or he could be a sadist who likes to make a sissy cry. I took a breath and answered his call without opening the video, hoping he'd be willing to talk for just a little bit. As I did, I thought back to how this sissy life truly began for me.

Talk for a bit. That's all I was trying to do a year ago when I stumbled across Mistress Sally in a random chatroom. I had been a sissy/crossdresser on and off for most of my life. I had purged a few times but always returned to it. After that night, purging would never be an option for me again.

Mistress Sally was her screen name. And, as it turns out, her actual name as well. I sent her a private message looking for a little sexy chat for the night, and one minute later she replied and our relationship began.

It began as most chats do: How are you? ASL? What's new tonight, and so on. We seemed to hit it off, as she was interested the idea of making guys wear girl's clothes and photograph themselves or perform on web cams and the like for a little fun. I had taken pictures of myself before and sent them to people, so I wasn't really against the idea. When a sissy is dressed up and engaged by a creative man or woman, we tend to fall into a bit of a horny haze that expels our normal inhibitions as we, for some reason, believe we can trust these strangers with our intimate thoughts and overly personal and potentially damaging pictures of ourselves.

But she was kind and engaging and I played her game. I let her lead. I had a habit of doming from the bottom from time to time, but I let go with her and allowed her to guide me towards wat she wanted. It was intoxicating. It was extremely rare to find a woman interested in sissies, much less one that seemed to know exactly what I was hoping to get out of the exchange while still getting what she wanted.

After a few minutes I readily turned on my web cam and allowed myself to follow her instructions. Knowing a woman was watching me and directing my every move was an incredible feeling and I fell totally and completely into the satin trap. I was told to play Britney Spears music and show her how I can dance like a pop star. I did my best, but I was simply not a dancer. I could hear her laughing, and I could feel that wave of embarrassment starting to creep in. When the song was through, she critiqued me harshly and told me to do it again...and do it better. I did as I was told as I swam in her sea of domination.

Four times I danced to the same song before she was at least somewhat satisfied. I had learned a few moves through her coaching, and wasn't totally ridiculous anymore, though she had mentioned twerking for future lessons. She then had me strike a feminine pose like a little pop star slut and hold it. Then a new pose from behind...and hold it. I didn't understand what was happening, but I also really didn't care. I could feel my cock...my clit...growing in my panties. Not rock hard to be sure as I was extremely nervous, but it was stiff enough to notice. She told me to come back to the computer and sit down, and so I did, while trying to wiggle my hips along the way. Sissies in heat always act up for their audience.

She told me to take a break and catch my breath. She then playfully began to ask me more personal questions. Like where I lived and what I did for work, simple things that new friends ask each other. I gave her the answers she was looking for and she was pleased. She then told me to sit still and give her a sissy smile...once more, I followed instructions. She then told me to go freshen up my makeup while she worked on something for a few minutes, so away I went to add a new coat of red lipstick.

I was enthralled with this woman. I was excited beyond belief to have found someone as fun as her. I touched up my red lips and pulled my garters tighter and wiggled my shoulders as I looked in the mirror smiling at myself. I was really getting hard now in anticipation of being given permission to jerk off and cum for her. I rubbed my cock/clit over the front of my panties like a girl, just feeling the stiffness and the warmth of it. I had never been so horny, and a couple minutes later, I heard Mistress Sally call me back to the computer...that's when I knew I was in trouble.