Tuesday, 22 March 2011

At work...in a dress

Sometimes I can't help thinking about things that have to happen in the future.

My future. As a sissy.

One scenario I keep coming back to, is daydreaming of my first day at work dressed as a woman...


Charlotte gets up from bed and walks over to the wardrobe. She opens the door, turns around and says, "time to find you some pretty clothes...hmmm...a dress or a skirt and top? You're goimg to look so cute!"

I get up, shower, do my hair and slip on my underwear. I wear a corset and some cute panties. As I pull up my panties, I start to feel like a proper woman...I already have small breasts, and the front of my panties is completely flat.

I apply my make up. "You have to look pretty on your first day honey...", Charlotte teases.

I try on a few outfits. First some dresses...

Then after a change of panties to avoid a VPL, a skirt...

As I slide the skirt up my smooth legs, the silky lining reminds me of the sissy I am. It feels delicious, but I also feel humiliated in front of Charlotte. I should be her man...not her sissy girlfriend. I fasten the skirt, before Charlotte says, "Stop, I have the perfect outfit".

I take off the skirt, and Charlotte hands me a pretty dress...Perfect for a sissy...

Charlotte holds the dress in front of me, and I step into it. Holding eye contact, Charlotte looks amused and reassuring at the same time. I feel the dress hugging my body as Charlotte zips me up and ties a pink bow around my waist. She hugs me, her wearing a cute black sheath dress from Calvin Klein...

It feel strange as she hugs me, the skirts of our dresses touching each other. It's the kind of hug a girl gives a girl...not the kind I used to get.

"Perfect! Take a look at yourself". I move over to the mirror, and can't believe what I see. I see myself, as a woman. Encased in a pretty dress. I touch up my make-up...

...and together we leave for work.

Charlotte drives, and as we pull up to my office she can barely contain her laughter.

"Remember Caity...try not to worry. Most of the office already knows after my email. Pretty much all the girls know...the only people wo'll be surprised are the guys. Have a good day honey!"


My heels click as I approach the office. Every click is a reminder that I'm no longer a man...

I nervously walk into the corridor. Sarah is waiting for me. She looks serious. "So it is true!"', she says, arms folded. "I always knew. You look very cute. An appropriate dress for someone like you...follow me, sissy...I mean Caitlin".

As I follow Sarah, everywhere I look people are covering their mouths nd laughing. I can hear whispers as I pass...

"Oh my God...what a wimp..."

"To think...I used to fancy him..."

"Aaaaawwwww. So sweet. I have a dress just like yours".

"I always knew you were a sissy...let's catch up later and you can tell me all about it!"

"So Charlotte was right... He is a sissy".

All I could do is smile sweetly and follow Sarah. We head towards Lorraine's office. Lorraine is my boss. She's also friends with Charlotte...

"Come in Caitlin...now let me take a look at you. You'll do nicely".

"I...I...". I try to get the words out, but they won't come out.

"It's okay Caitlin", Lorraine said reassuringly. "You look divine. Such a pretty dress. I love your shoes too."


"Charlotte told me what to expect, and why. From what she says, you'll make a much better girl than a boy...and I can she that she's right. I mean, she told me that you're rather...um...underdeveloped...AND that you look great in dresses..."

All I could do is stare back. I can't believe Charlotte had told her about my ...problem.

"Come on. Let's get you to HR and get your contract amended. Follow me."

I follow Lorraine through two doors, and into Abigail's office.

"Abby...here's Caitlin".

As I walk in, I notice Abigail grinning a me. I can't tell if she's being friendly, or is stifling laughter.

"See you later, Caitlin", Lorraine says, letting out a chuckle as she leaves me in front of Abigail, looking amazing in her black shift dress.

"Let me take a loom at you...hmmmmmm...pretty dress, and I love your hair. How does it feel?", Lorraine asked.

"S...s...sorry?" I reply.

"How does it feel? To be a girl? To be one of us? Long hair...pretty dress...make up...a pretty girl...a sissy? How does it feel?"

I feel so small, standing there in my dress. I'm suddenly aware of my bra...may tight panties...the skirt of my dress skimming my legs.

"I...I...". Still can't get the words out.

"It feels good doesn't it? To find your place. To be a woman. Standing in front of me...in pretty lingerie...cute dress...thinking of Charlotte, in her office, in her cute outfit...she told me she was wearing the Calvin Klein dress today...the one the Managing Partner at her firm bought her...James."

I just blush, but inside I'm terrified. How come charlotte hasn't mentioned James before? And he bought her a dress!? That's the sort of thing...a...a...boyfriend migjt do. All I can think about is Charlotte...in the office at her firm...staying late...being kissed by James...

While I'm stuck in my office...in a pretty dress...a sissy. No match for a real man...

I feel humiliated. I feel terrified of losing Charlotte. I feel scared. I feel more aroused than I've ever felt...

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