Sunday, 14 November 2010

Maggy London dresses

I was browsing one of my favourite online stores earlier (Nordstrom) and I felt compelled to mention a designer called Maggy London. Some of the dresses she has on the site are simply divine!

I like to look at the dresses, pause, and just imagine what each one would feel like on. I think about being at a party where girls approach me and tell me how pretty I look...

Here are 5 I would LOVE to own...

Floaty, fun, and not too formal...

This feels like a second date dress, if the date is dinner in an upscale restaurant. I adore the feminine lace detail around the hem.

This dress is super sexy! Figure hugging tastic! The sleeves are great.

Pretty is the word I'd describe for the next dress. The contrast between the top and the taffeta skirt works beautifully, and the bow...another dress I just go weak at the knees thinking about wearing.

I really like the top part of this dress too.

I'd also like to put in a word for the two models. Both fantastic role models for my journey from man to sissy to girl (although I suspect I'll always be a sissy). I adore the way they look (I'd much rather be them than be with them) and while I almost have the hair length now, Charlotte and I are continuing to work on the rest.

Please let me know what you think.


Prettiest dress ever?

So for me, this is one of the prettiest dresses I've ever seen. I think about what it'll be like to wear dresses like this out with Charlotte when She deems me ready.

Not sure where I'd wear this one though...perhaps a party!?

In any case, just the thought of slipping this on makes me go weak at the knees...gorgeous. You never know...Christmas is coming...

Tuesday, 9 November 2010

True story

I went to a house party on the weekend.

I'd been having such a fun night. Talking to lots of people I hadn't seen in ages, and meeting new people too. Charlotte was away on some law firm team building weekend.

I got speaking to a gorgeous girl called Sarah. Sarah had natural blonde, long hair. She looked quite alot like this girl...

She was clearly the most attractive girl at the party, and was wearing a simple black skirt, vest top and ballet pumps. After about ten minutes of us talking and getting on famously, Sarah said, out of the blue, "Please don't take this the wrong way, but I want to ask you something..."

At this point I was completely unpurturbed. I mean, that's not an unusual thing to say in conversation.

She continued, but instead of asking me a question, she bent towards me and whispered in my ear.

"You're a sissy. I can tell."


The blood must have drained from my face, because she could tell she'd hit a nerve.

"I...I...don't know what you mean..."

"I think you do", she replied.

I looked around. No-one had heard a thing. Too busy in their own conversations. I paraphrase, but she went on...

"You see, I know, because my brother is a sissy too. I once caught him in my clothes. And since we've been talking, you've been looking at me the same way he does. You've been looking me up and down the way a girl would. Checking out my outfit, my hair..."

She grabbed my hand, and placed it on her leg, where her skirt met her bare flesh She looked me in the eye, all the while.

"You see, when I do this, I can tell you're aroused. But not like a real man would be."

Sarah smiled and looked sympathetic.

"You know, I think you'd look good in this skirt. I bet you have the legs for it. Just like mine. Sissy." She knew she was teasing me. "It's okay honey. You're secret's safe with me. Us girls must stick together."

Without another word, she got up, and I didn't see her again for the rest of the party, aside from one very knowing smile as she left.


When I got home, I called Charlotte, and told her. She giggled, dismissively.

"You're REALLY surprised!? Have you looked at yourself recently?"

It was true. I now have long, straight, conditioned brunette hair, shaped eyebrows, and have lost about a stone in weight in the last 6 months. I also have shaved arms (and legs, although not on display at the party), and practically no stubble.

Perhaps Sarah didn't have to be quite as perceptive as I thought.

Outed as a sissy. Could there be a bigger humiliation?


Sunday, 3 October 2010

Women I'd like to be...Rachel Bilson

The latest in my series of women I'd like to be, I don't know how this one has taken so long...

Rachel Bilson is a total fashion icon, and a real inspiration for someone like me.

Who else used to watch the OC and think, "I totally want to be this woman..."

Petite (5ft 2), feminine, beautiful, pretty and successful. Dark long hair, facially stunning, a perfect figure (for me at least, she's the ideal size). She especially suits dresses, and is as close to how I would like to look as I can dream of.

Here are some inspirational photos...

This has to be one of my faves of Rachel. I know this was taken a while ago, but Rachel has the 50s look going on (and three quarter length skirts are so fashionable right now). This one seems so fun and feminine to wear. Plus, what a smile....

Okay, which one of you wouldn't like to be dressed like this. She's so stunning. I lover her hair and the outfit, especially the petticoat...

This red party dress is a delight! Imagine hitting the dance floor in'd be sure to turn some heads.

I think this one is an early one of Rachel. Very cute, amazing legs. This could be a great second date outfit.

This photo is very Audrey Hepburn (another sissy inspiration!). I adore her dress. Imagine swishing through a party in this number.

Wow...that's all I can say. I'd love to wear this dress, perhaps on holiday with a hunky guy. Love the ribbon around her waist.

The flared skirt on this dress is just dreamy. When I look at this photo I think about Charlotte parading me through town looking like this, whispering 'sissy' in my ear.

Once again, Rachel pulls off this dress perfectly. So feminine, I love the lace underskirt. I bet this feels amazing on.

Just beautiful. I adore this woman. Imagine if Rachel was your roommate, and she helped you dress and be the sissy you are.

This pic makes me think how much I'd love to be Rachel...being helped into dresses, a full rail of amazing outfits to choose from...

I'd just love to look like this...this feels like a housewife shot...waiting for hubby to come home

Finally a pretty is this woman. I love her hair too.

So in short, Rachel Bilson, you are an absolute hottie! I aspire to look like you, and with Charlotte's help, I'm getting closer...


Sunday, 26 September 2010

Poll result

It's been SO long since I put this poll out, but I wanted to talk about the results of the first questions I ever asked on this blog.

The question was, "To sissies: what would you like your girlfriend to do to you?"

In reverse order:

  • Dress you up in a pretty skirt/top combo, then go out on a date, leaving you to imagine what she's up to... (6%)

I have to say, I'm not entirely surprised this polled so low. Most sissies seem to want to get in on the action...

However, this remains both a fantasy and a horror of mine. Sitting at home sissified while my girlfriend is doing who knows what with a hot guy...a real guy...I can't bear to lose Charlotte to someone else, but I can't help thinking it's inevitable. Women need real men.

I imagine Charlotte leaving out her sex toys and texting me frequent updates of what's she's thinking or actually doing. She asks me to recreate her actions on the toys...practice makes perfect.

  • Takes you shopping for skirts and dresses while dressed as a boy, telling all of the shop assistants you're a sissy (12%)

Well, this one has actually happened to me (see my earlier posts). I can tell you there is nothing more humiliating (or arousing) than facing the muted giggles and laughs of salesgirls in a department store as they help you with outfits. In my case it was skirt-shopping, with Charlotte joining in the laughter.

  • Get all her friends to donate their old skirts and dresses, then invite them around to dress you up and laugh (19%)

Unfortunately, another one that's happened to me. Charlotte's friends now all know about my dressing, and many of them have donated clothes for the cause. So sweet of them, although it's obvious they only do it to come around and laugh at me.

  • Dress you up in a cute Elle MacPherson babydoll nightie, take you to bed and reach for the rampant rabbit to show you what you've been missing (22%)

I can't see the sex toy part happening any time soon, but who knows? I don't feel ready for that kind of thing, although there is a part of me beginning to wonder what it would be like...

I mean, if I'm going to be a girl full time, are men part of my future? There is a huge submissive part of me that wants to know...taken...but right now, I still find Charlotte enormously attractive. Perhaps she will see this and get ideas.

  • Style your hair, put you in a flirty sundress and take you out on a double date, with guys who are on a promise (38%)

I'm not surprised this one won out. It's also my favourite.

I think about Charlotte dressing me before our dates...teasing me...telling me how pretty I look...styling my hair...giggling.

I imagine being out on the date...two hot guys...Charlotte and I sneaking off to the bathroom for her to tease me. Their eyes all over us in our pretty dresses.

Then I think about Charlotte making out with one of the guys in front of me, and the moment I realise I have to do the same with the other guy in front of her...wearing my pretty dress...kissing him...straddling him...feeling his hardness against me...touching him...

Somehow the thought of Charlotte there makes it more palatable. Having her witness first hand the sissy I am, pleasing her by being with him...

Her sissy.

It's been so long since I last posted.

Charlotte asked me to stop. To see if I could put my feelings behind me.

"Try being a real man for a while. You might like it".

Needless to say, it hasn't worked. Like just about every sissy I've ever heard from, it's not something you can bury. It's not just part of me. It IS me.

Deep inside, I desperately need to be feminine. A girl. A sissy.

Charlotte's sissy.

To celebrate my discovery (that there is no turning), Charlotte bought me this skirt, from Delia's...

I'm wearing it now. with my cute Elle MacPherson panties...

And before you ask, yes, everything I have DOES fit in there (much to Charlotte's amusement).

I guess you could say I'm back to my old self.

Wednesday, 18 August 2010

Charlotte and I in 10 pictures

As part of Charlotte's ongoing mission to understand me better, she's asked me to come up with 10 pictures that tell the story of our life together so far, and how I think things will pan out in the future. My hopes. My fears.

Here goes:

I meet Charlotte, the most stunning girl I've ever met. I'm attracted to her femininity, her intelligence, her prettiness, beautiful long brown hair, her love of dresses, the way she is...everything about her. She's perfect.

We spend all our time together, and fall in love. Charlotte looks at me strangely sometimes, but slowly and surely we get closer and closer. I love her so, so much. After months together, Charlotte finally makes the first move and takes me to bed. She lies on the bed waiting for me to make the first move. I get scared, and she comforts me.

When Charlotte finally sees me naked, she laughs hysterically. She's never seen anyone so small. Because she's so kind and loving, she tells me it doesn't matter, and we carry on making out.

When we finally get down to it, I don't last very long, and I don't get much bigger. Although she's hardly a size queen, it's clear to me there's a difference between being big enough, and too small to do the job. It's clear I'm the latter, and Charlotte is disappointed when she realises things aren't going to get any better in the bedroom. Things don't change in the coming months. I'm not satisfying her, and not providing for her as a real man would.

After a few months of trying to make it work, Charlotte has a eureka moment. She looks at me in a different way. She notices my soft features, my longish hair, slender frame and fine, almost hairless smooth skin. She sees the intrinsic femininity in me for the first time, and can't believe she missed it before. She looks right through me and understand what she's seeing. What I am. Where she was sad and disappointed, she is now amused and perceives a new world of possibilities.

She looks into my eyes, and tells me, "I love you. But you're never going to be a man. You're my sissy, and I want to help you".

Before long, my whole body is smooth. I grow my hair longer, have it styled, and get rid of most of my male clothes. Charlotte hands me dresses, skirts, lingerie and pretty shoes to wear, encouraging me in her own way. I can see that she's having more fun with me now than she ever would have had I been her real man. I'm truly her sissy.

She introduces me to her friends, Beth and Lydia, and we go on holiday together with them. Every day they see me in a new feminine outfit, and laugh. They are kind to me though, and once they see how convincing I am, they lend me new outfits, mostly pretty sundresses and flirty skirts.

As I become more feminine, we become better friends. Eventually, we are full time, live-together girlfriends. We still sleep together, but our love-making has a very different feel to it. Charlotte is teaching me. Preparing me. I now spend every waking hour as a woman. I'm still her sissy, and she lets me know what I am by teasing me every day.

Charlotte meets a guy, and falls head over heels for him. First it's lust, and I help her dress for her dates, choosing her lingerie, dresses, and even her nightclothes for her weekends away with her man. When she returns, she tells me about it, smiling and giggling at my arousal. She now has a real man, and I'm her sissy. When he asks about me, she tells him the truth. I'm her full time, live-in sissy, and she's helping me to become the woman I am. He just looks at me pitifully, and says "she's cute".

Eventually Charlotte's hunk asks her to marry him. She says yes, and asks me to be her chief bridesmaid. We have so much fun dress-shopping, but I'm so sad. Charlotte explains I will always be the most important person in her life...her sissy girl Caitlin. She also explains that she will still help me become the woman I am. On her wedding day, she teases me all day, telling me I'm her sissy bridesmaid, and that all of the ushers are looking at me. At the end of the day, she invites me into her bridal suite, and I get her ready for her man. She let's me stay as they make love. I'm no match for her husband, so he doesn't mind at all. I watch as Charlotte is taken by a real man. All the time she looks into my eyes, and smiles sweetly, a tear in her eye.

After the wedding, I dye my hair blonde to embrace my new found femininity and have fun being a girl. Charlotte calls me every day and I meet her at least once a week. I get a job at a dress boutique, where no-one knows I'm not a real girl. I make girlfriends, and start to date...guys. Charlotte's training comes in very useful. What the future holds, I don't know, but in the picture above, I'm trying on wedding dresses.



The truth is, the chain of events above scares me to death. It also excites me a little...I don;t know to think. Charlotte is beginning to understand me, what I want, what I need, and how those things can be very different. She knows how my sissy mind works. As she pushes me further to explore my feminine side, she always reminds me that I'm her sissy. Her weak, feminine, skirted sissy. And how much she loves me. The pictures above represent one possible path. I can't bare to lose Charlotte. Who knows what will happen.

Tuesday, 17 August 2010

New skirt/New life

Charlotte bought me a new skirt one the weekend. I adore the skirt. It was the manner in which it was bought which was so humiliating.

Here it is...

We were in Selfridges (London) browsing for clothes. Charlotte often asks me my opinion on clothes, usually for her.

This time she lifted the skirt on the hanger, and held it up to my waist.

Then she said, in a normal speaker voice, but chuckling, "What does my sissy think of this?"

I just turned bright red, and Charlotte said, "It's your length. It'd look cute on you. Why don't you try it on?"

At the same time a shop assistant approached, looked at us both (Charlotte was still holding the skirt up against my waist) and asked if she could help.

She looked at me, looked at Charlotte, and you could see the light bulb switch on in her head by the change in expression. Now I've never seen a shop assistant with a bigger grin on her face. Ever.

And instead of saying no, Charlotte simply replies, deadpan "What do you think of this skirt on her?"

At this point I'm practically dying of embarrassment. Her?

The assistant replied, with an enormous smile and a giggle, "It's obviously her length. Add a pair of heels and a pink turtle-neck and she'd be ready to go! Do you know her size?"

At this point the assistant took the skirt from Charlotte, and held it up against my waist herself. This was all in the middle of the shop (although it was quiet).

"Yes", Charlotte replied. "She's a 10 in skirts, and we'll take it. Thank you".

"Cute", the assistant said, as she removed the skirt from my waist and looked at me, smiling. "Follow me".

We followed her to the checkout, Charlotte paid, and the sales assistant handed my the skirt, grinning from ear to ear. "Enjoy honey!"

With that we made a sharp exit, Charlotte with a massive grin on her face, me red as a beetroot.

So, what happened was humiliating enough, right? But what was even worse is what this means for my future, and how feminine I must look to everyone else now.

I mean, the sales assistant was clearly amused. But she hardly questioned whether Charlotte was joking. She took one look at me, and assumed Charlotte was completely serious, even if the situation was funny to her.

And I can only the sales assistant, I look like the kind of guy/girl who would look good in that skirt. I look like the kind of guy/girl who would enjoy wearing that skirt. When she looked at me, she didn't see 'guy'.

She saw 'sissy'. She saw 'girl'.

My life is changing beyond recognition.


The post-script to this story of humiliation, is that I spent the rest of the day in my new skirt, a pink turtle-neck (borrowed from Charlotte), and a black pair of mules (low heeled).

And the truth is...I like the skirt so much, it was worth the humiliation.

That's how much of a sissy girl I've become.

Which leads me to think...if I'm such a sissy, where does this leave Charlotte and her future...? While she actively pushes my transition to sissy/girl, I can no longer help thinking I'm no longer the man of her dreams.

What if, while I slowly turn into a beautiful, attractive, pretty woman, like this...

Charlotte realizes what she really wants is a real guy, like this...

And as I become more feminine...moving deeper into womanhood, which will I need? Which will I want?


Monday, 16 August 2010

Amazing Blog

I wanted to introduce you to a blog I found recently. This is the blog of Marie Jeannette McGrath, from Panama.

She has a wonderful wardrobe and a great taste in pretty, feminine clothes.

The thing I LOVE about Marie, is that she describes the way she feels wearing her clothes.
Take these examples...

"I'm feeling very cute with my ribbon bow around my waist!"

"This outfit screams summer for me! I feel so colorful and happy that I can just jump of joy!"

"I was very happy wearing this sailor look for one particular reason: blue stiletto shoes!! I adoooore these blue stilettos, but I dont get to wear them too often. I also love the white ribbon tied around my waist because the bow gives the outfit a cute and girlie feel to it."

"I must say, I loooooooooooooooove my outfit today. I dont know why it makes me so happy, but it really does. I love the happy colors and I am wearing my new waist skirt. I love this outfit so much I dont want to take it off!!!"
"I felt extremely girlie in this outfit, maaaybe even a little too girlie... but I was happy wearing this to watch the new Harry Potter movie with my parents and my boyfriend. The pink top goes with the pink flowers in the skirt that arent very easy to see in this photo and the white accesories goes with the white border of the skirt... To make this even MORE girlie, I wore a white flower in my hair... jejeje maybe I should be skipping around everywhere I go :)"
Check out her blog. She's so cute!

Things I'm learning to LOVE...

It's been some transition so far, and the more I descend (or ascend) deeper into a state of femininity, the more my tastes change.

Anyway, to celebrate this, I wanted to share some things I found recently that I LOVE.

Here's the first one...

This is so pretty I could burst! I imagine wearing this out to lunch with the girls, or perhaps on a first date with a pink vest top, some sexy lingerie and strappy heels. So pretty...

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...".