Corporate Sissy Ch. 03

Corporate Sissy - Chapter 3 - Sissy learns more about how she got here

Except for the turning of the pages of the contract, there was not a sound in the room. I'm sure I didn't even breathe during the time it took me to read the words on the pages in front of me. When I was done, I read it again to make sure this wasn't a dream or hallucination.

I looked up after the second reading and looked into those stunning green eyes again. My mouth was open and the power of speech seemed to have left me. My head was both exploding with the implications of what I had just read and foggy with the magnitude of the decision I was being forced to make.

Not that it was hard to spot but Ms. Taylor saw my consternation and began to speak. She gave me a narrative of all that had happened to bring us to this point. The type of surveillance her company had pursued and the events that had led me to be here at this table at this moment. I listened with great intent and a growing sense of inevitability that made me believe that I was destined to be here.

She outlined how they knew that I had begun wearing my older sister's panties when I was only 9 years old and that how over the years that love of panties had blossomed into a love of lingerie. She described the many times I wore stockings and camisoles while attending graduate school and the names of the women with whom I had shared my fetish. She knew how each of my past relationships had ended and how each loss had driven me further into a world of exploration of cross dressing and the research into the lifestyles of being a sissy and even transgender reassignment.

There was a list of the experimental sexual adventures I had experienced and the outcomes of each. Some had been successful like the 8 weeks I had travelled in Europe with Bret and how we had slowly peeled back the layers of hesitation about a same sex relationship. I was informed that pictures and videos existed in the company vaults showing the first time I had sucked his cock right through to how we would dress for each other.

It brought back the memory of the first night he had asked me to dress for him and be his "date" for the night. I had spent a lot of time shaving and preparing for this moment and had chosen black stay up stockings, frilly pink panties, a black see-through camisole, pink bra stuffed with some rolled up pantihose, a plaid mid-thigh length skirt and pink sweater. I finished the outfit with 4" heels and some makeup and of course shiny deep red lipstick. As this was really my first attempt at a complete transformation, I'm sure I didn't look anything close to what he had hoped but we had our date as planned.

He took me out to a quiet place for a drink and some food. We talked about what was happening between us and what that meant. We had been travelling together for a month and the tension between us had grown to the point we couldn't ignore it any longer.

As we came to the end of the dinner he asked me if I'd very been collared? I didn't quite understand what that meant so he explained that to be collared is to offer a gift of submission and the collar is the sign that the gift has been accepted and is respected and honoured by both of us. In the ensuing silence we looked at one another across the table and I slowly nodded that I would be accepting of that arrangement.

He reached under the table and pulled out a beautiful white leather collar with the single D ring on the front. Without breaking eye contact he stood and came around the table behind me. I held my breath as he placed the collar around my neck and clicked the lock in place. He bent and whispered in my ear that for the next month I was his to command.

All during this exchange my cock was pulsing in my panties. Not only was I living a life-long fantasy as dressing as a girl out in public, but now I had offered myself completely to someone I trusted and who wanted me. I stood and looked him the eye and whispered "I'm yours Master".

That night as soon as we entered the hotel room he forced me to my knees and told me to proceed. I reached up and undid his pants. His cock, which I had seen many times over the past month but hadn't touched, was hard as a rock as I pulled it from his pants and underwear. I felt the hot smooth skin in my hand and instinctively began to stroke him gently as I massaged his tight balls with my other hand.

With my face close to his cock I could smell his warm scent of soap and man sweat. He knew better than to rush me but with my heart pounding out of chest I slowly opened my mouth and for the first time let a man's cock enter my mouth. I closed my eyes and knew within seconds that this was something I wanted to get really, really good at doing. His cock had a slightly salty taste and the skin, as hard as he was, was unbelievably smooth and soft. Knowing how my cock responded when I I was being sucked or when I stroked allowed me to suck and stroke him in the same ways I enjoyed.

After a minute or two he began to thrust a bit deeper and finally I was taking most of him into the back of my throat. He placed his hands on the back of my head and began to throat fuck me hard eventually pushing his entire length into my mouth and throat. It had been weeks since either of us had cum so I knew he would not last long. With his cock wet from my saliva and one hand wrapped around him and the other cupping his balls he began the swell even more.

He looked me in the eyes and told me to take his load and show him before I swallowed. He began to cum and my brain exploded with the pleasure of serving this cock. His thrusts became stronger, and I could feel rope after rope of cum splash into my mouth. Finally, he stopped moving and as he caught his breath, I gently sucked the last of his cum into my mouth.

He pulled out of my mouth and looked down to see my red lipped mouth wide open showing his cum covering my tongue. He nodded and said softly, "Swallow slut and remember who owns you." By now my own cock was swollen to the point of pain in my panties and as I swallowed my very first load of cum my cock twitched and I felt pre-cum leak out.

For the rest of our time together that summer I was his submissive sissy slut and experimented with as many aspects of a D/s dynamic as we could. I became even better at sucking his cock. We played with anal sex and I found it possible to experience a hands free cum when being fucked in a certain way. And through it all we spent a lot of time learning how best to dress me as his sissy. By the end of the trip I was able to dress and do my make up in such a way that I was passable in most situations and for all intents and purposes, I was his girlfriend.

On a deeper level I discovered that under the male façade I had presented to the world was a seething need to live as a shemale, enjoying all the luxuries of a woman and still the pleasures of having a cock. It was the joy and satisfaction I felt from my submission, and to my need to be used and to serve someone I trusted that had led me to this moment in a boardroom face to face with a beautiful woman and the need to make the single most important decision of my life.