Saturday, 26 June 2010

Charlotte's Perspective on the Life of a Sissy

I was talking with Charlotte a few days ago, about how she always seems to presume to know what I'm thinking and what I'm going through.

It's strange, because obviously she's closest to what's happening with my transformation from boy to sissy and closer to girl. Even so, despite her patience, I can't believe she could possibly know what I'm thinking.

Even though she disagreed, she did agree to speak to a psychiatrist friend of hers (Lorraine) who knows more about it.

When she got back, we sat down to talk.

"I think I understand much more about how you feel", Charlotte said, smiling.

"I don't think you possibly could, even after seeing Lorraine", I replied.

"Perhaps, but she was very enlightening. She took me through so much. What you want. What you need but don't want. And what's going to's SO cool"

"What is?" I said, a little shocked.

"That I can begin to understand you so well. My little ...sissy."

In the pause she looked me up and down, nodding and smiling. Charlotte chose my outfit this morning. Since I lost the extra weight I now fit into her clothes, and although I have my own wardrobe, I occasionally borrow hers. It's SO hot here today, so this is what I'm wearing...

No wonder Charlotte knows I'm her sissy.

"For instance", Charlotte said, "I know that you NEED me to call you...sissy...girl...pretty...small". She looked down and giggled as she said the last word. "Even if you don't WANT me to, at least not conciously".

"Charlotte. Don't..."

"Ok. But I bet I can read your past. Then I'm going to tell you your future."


"Yes. Really Caity darling".

She looked me up and down again, and smiled as I rearranged my skirt and now shoulder length hair. "Oh, how much you've changed", Charlotte said. I was still playing nervously with the hem of my skirt as she started.

"So. The life of a sissy" Charlotte said. "You've come so far. I mean...look at your cute dress and hair. So pretty. So feminine. But let's start at the beginning..."

I looked at her. It was obvious she was enjoying herself.


"Growing up...hmmm...I bet you looked at your older sister. Admired her. Wanted to be like her. I bet you...hmmm...wanted to borrow her clothes. I bet you looked at your wardrobe, looked at hers, and back at boring. How plain...but hers, how colourful, how fun! Did you?"


"I thought so", said Charlotte, nodding her head. "I imagine you looked at her pretty dresses, and wanted to be a girl, wearing those lovely dresses, those skirts. Ribbons in your long hair. Petticoats. How pretty you would look. How much more attention you would get, in those clothes...a gorgeous girl like your elder sister..."


"And what about that wedding you attended with your sister? I bet you we're happy were you?"

" know I wasn't", I replied.

"Yes...because of your page boy outfit, right?"

"Yes, exactly. I've told you this before"

Charlotte just laughed. "Yes. But according to Lorraine, there was probably more to it. At the wedding, was your sister there?"


"Was she the flower girl?"

"No", I replied, knowing where she was going. Because I knew the truth. "She was the bridesmaid. She's older than me". I swallowed, nervously.

"How was her dress?" Charlotte asked, looking right at me, assessing me.

"I don't remember."

"Oh I think you do. I bet you remember EVERY detail. Her smile as she tried it on for the first time and walked it through the house, getting so much more attention than you. The looks she got from the other guests. How feminine she looked. I bet you remember the colour, the detail of the skirt, the bodice...everything. Why?" Charlotte posed, accusingly.

"Because...I ...I don't remember" I said, looking down.

"Yes, of course you do sissy. You wanted the flowers in your hair, and in your hand. You wanted everyone looking at you, as you walked prettily into the room, the skirts caressing your pretty...and girly...a sissy". Charlotte looked at me, noticing me adjust my position. "And not only that...look at you know. You're aroused...aren't you?"


"Oh how cute. Aroused by the thought of being a sweet bridesmaid. There's plenty of time for that yet Caity. Despite, I'm not married yet. Perhaps you can be mine".


"Then there's your school. Mixed, yes?"

I nodded.

"Yes. Thought so. Lorraine said you probably longed for the girls in your school. Probably spent more time looking at girls than any other boy. But not for the same reason. Why?"

"Because I liked girls..."

"Yes, of course you liked girls. But Lorraine thinks it's for a different reason than the other boys. You ALL liked girls. But YOU wanted to BE one. You admired girls. You desperately wanted to be like all the other girls."

"You wanted to be like the other girls, didn't you? Prissy and preppy. Knee-length skirts, blouse and hair bands. I bet you longed to be away from the boys, to be together with other girls, talking about fashion, and hair, make-up...boys. I bet you dreamed of stepping into a school skirt in the morning, instead of your silly trousers...legs together, the lining of the skirt so smooth on your bare legs as you pull it and catch at the back... I bet you had so many girl friends, but no girlfriends!"

I looked at Charlotte, not believing what I was hearing. I'd never told her this stuff before...


"And when you finally got a old were you again?", Charlotte asked.


"Who was she?"

"Her name was Amy". I told Charlotte what she looked like. Petite. Long dark hair. Pretty. Slender, like a dancer.

"How did you get the date? Did you ask her?"

"No", I replied. "We'd been friends for years. It was just before the summer holidays. She asked me if I wanted to go to a movie. I said yes".

Charlotte smiled. "So SHE asked YOU out? Surely that's a guys job? I mean, I would expect that...never mind. So what was she wearing?"

"She wore a green long sleeved top and beige pleated skirt. She looked beautiful."

"Did you find her attractive?"

"Of course. She was...beautiful", I replied.

"What happened?" Caitlin asked.

"We went out. To the cinema".

"Did you make out".

"No. We held hands though. Through the movie".

"And you didn't make a move?"


"Why not? Surely she wanted you to?"

"Probably. It just didn't...feel right..."

"Did you see her again during the holidays?"

"Yes. At a house party the following week. She looked at me, smiled and walked away" I remembered, fiddling with the hem of my skirt. Charlotte smiled at me.


"She walked away, to be with someone else".

"A guy?, Charlotte said, clearly amused.

"Yes. They were kissing, and she looked at me over his shoulder. She broke off the kiss, and smiled at me. Then she turned back to another kiss."

"Do you remember what she was wearing?"

"Yes. She had on a pretty stripy dress".

"So you lost her. To a bigger, better man? I bet she knew then, you were a sissy. She knew you'd rather be...well...a girl. Trust you to remember what she was wearing!" she said, laughing again. "I bet she thought you'd make a cute sissy though. Maybe we'll have to get you what she got at the party. Maybe we'll have to get you a man".

She looked amused again, but there was something else in her eyes. There's no arguing with Charlotte in this mood. Even when she scares me.

"Some on", Charlotte said. "Let's take some photos of you in that dress for the girls at work...".


  1. Charlotte understands all, Caitlin, even the bits you may suppress in your mind.

  2. That dress you wore is so cute. I always go with dresses on the hot days too!

  3. Caitlin,

    Much of what Charlotte says resonates with me too.



Thank you for leaving a comment! xxx