Sunday, 31 January 2010

Women I Would LOVE to be...

While I continue with the story of my first real exposure into the world of dresses (yay), Charlotte has once again asked me to post pictures of more women I would like to be, and why...

I admire high-powered, feminine businesswomen. Why shouldn't a woman be feminine and powerful at the same time. Such a potent combination. I would love to be this woman, in her smart skirt and jacket. Sexy, pretty, and clearly a woman who knows what she wants. I love it. I like to think what it would be like to be dressed like this for a meeting, the gorgeous feeling of crossing my legs in that skirt, the slip soft up against my thighs... KNOWING I look so beautiful.

I think seeing women looking so happy and content in a dress is amazing. I mean, who wouldn't want to be this woman!? Outside on a summer's day, in a sundress. YAY FOR SUNDRESSES!!! She's stunning. I think about being her, and walking around all day dressed like this, skirt softly caressing my legs, receiving admiring glances from girls and guys...So pretty, and I love her hair too.

The thought of skirt shopping...for the attraction here. It looks as though she's just tried the two skirts on in the background, but has settled for the floral option. She's having her photo taken because she likes her skirt so much. She looks so proud. I love skirts. I would love to spend all day in skirts and dresses (it's already happening I guess) however much I protest that that's not the case. I would love to be this girl.

So here's a key fantasy of mine. My mother recognises I'm a sissy, and tells my girlfriend. My girlfriend starts seeing other guys, because she doesn't want to be with a sissy, although she still loves me. She encourages me, with my mother's help, to be the girl I should always have been. This culminates them marrying me off to a cute guy. That's me in the wedding dress, and my ex-girlfriend as bridesmaid. She lovingly teases me throughout the ceremony, about what a sissy I am and the pretty girl I've become.

So this one's about a lost opportunity. I feel genuinly cheated that I didn't have a prom...never had the opportunity to dress up in a beautiful white dress and be taken out and treated like a lady for the first time. I adore her dress and tiara, and this photo encapsulates her excitement...texting her friends and looking so happy and girly. A lovely picture...if only this could have been me!

There's absolutely nothing wrong with women dressing a little flirty if they feel like it. I mean, girls just LOVE to have fun, and clearly wearing short skirts and looking good, catching attention etc is part of the equation for many women. Good on them. I like to think that this is me, changing for a second or third date, admiring my skirt, thinking about how much my boyfriend will like me in it. I imagine sitting on his lap later, up close, kissing. Pleated skirts are fantastic!! She looks fab!

Definitely the closet businesswoman coming out in me again. To spend all day dressed like this, in smart shoes, skirt just below the knee and a red top...I love her hair too, and her smile. I would kill to look like this for the rest of my life. I love the feel of fully lined skirts up against my legs...slightly restrictive and keeping my stride length feminine and dainty. Silly I know.

She is content and wearing a skirt. Definitely a theme developing here!! Need I really say more. Okay, I will. I would love to be posing in a knee length smart skirt, having my photo taken because I am a beautiful girl. Do you girls realise how lucky you are to have the opportunity to dress like this all of the time!!!??? Hmmmm...skirt, dress or trousers....WHY would you ever choose trousers!??? Skirts and dresses rule! If only I was born a girl. She looks so happy.

And finally. The excitement on her face is thrilling! I can't help thinking what it would be like to choose my wedding dress, to have my hair done, to be made up, and then slip into the dress on my wedding day. To look so divine, so pretty, in my dress, while all the guests realise what a sissy I really am. Humiliated, and a sissy. Looking so cute...

What do you think of my comments???? Please let me know which women you identify with, or just like, and why...xxxxxx

Friday, 29 January 2010

I'm in dresses...continued (2)

"Why don't we style her hair first", suggested Beth.

"Great idea! Come here Caitlin" replied Charlotte. "Your hair's grown so much in the last 6 weeks. I'd almost call it long...what can we do with it?"


"Oh shush can we style it before you get changed into your FIRST dress! So exciting! Here are some options", said Beth, showing me the magazine pictures...

"Which is your favourite Caitlin?"

"I don't know...I'm not sure I'm ready for..."

"Oh don't be such a girl..." cried Charlotte, causing Beth to fall into fits of laughter.

"Why don't you get changed first Caity. Here...". Charlotte handed me the dress. It felt so soft in my arms. "Here's the first one...let's see how you look in it before we try the others."

"The others...?"

"Oh silly...You've wanted to get into dresses for ages, haven't you. Did you think we wouldn't buy you some more dresses to go with your skirts? Wait until you see what else we've got you..." said Charlotte.

"But first try the pink one on" suggested Beth. "You can get changed front of us"


"Oh don't be shy. We're all girls here!" said Charlotte.

"Yes, definitely no guys here." added Beth. "Go on...take off yor clothes"

I took off my top, and lowered my trousers, exposing my panties.

"Oh..." said Beth, starting to giggle. "I have a pair of panties just like yours. Adorable. Come on. Put the dress on. I'm sure you know how."

I held the dress out in front of me, and stepped into the skirt. The silky lining brushed up against my smooth legs. I was instantly aroused. Beth moved behind me, and guided my arms into the dress. Charlotte started to button me up in front.

"Oh my....don't you look gorgeous....just like a real girl. Let me arrange your hair."

Beth was openly laughing now..."oh...don't you make a cute much better than you were as a boy...the guys are going to LOVE you..."

The feeling of the dress on my legs and body was overwhelming. But I also natural. I've always loved dresses on Charlotte. Now I was wearing one. The first of many I suppose.

"You look LOVELY Caity! Let's go out!" cried Charlotte.

"Yeeeeeeeeeeesssss", Beth agreed.

What would happen next....?

Thursday, 28 January 2010

I'm in dresses...continued

I had my feet up on the sofa when Charlotte came home, relaxing in a pair of jogging bottoms and t-shirt (with my Elle MacPherson panties on underneath, which I love[pictured below])

"Hey Caity! How're things"

"Okay. What have you got there?"

"LOADS of lovely things from our shopping trip. Beth's just parking the car. She'll be up in a sec". Charlotte was wearing her pink jumper and knee length black skirt. She looked lovely.

"Beth's with you?" I was worried. Beth had been kind enough to give me some of her old skirts. She used to fancy me. But now she knows. SHE KNOWS I'M A SISSY. And I hadn't actually seen her since she found out.

Beth walked through the door.

"Hi...C...Caitlin", Beth smiled, and could hardly contain her laughter. Beth was wearing a gorgeous brown shirtdress. She looked better than ever.

"Hi Beth", I replied, cautiously.

Charlotte turned back to me. "We bought some things...we bought you some things".

Oh my god.

"Me and Beth have been talking, and it's time you smartened up a little. We..."

"...we got you some dresses!" Beth finished off Charlotte's sentence for her. "You're going to ADORE wearing them ...Caitlin"

Both Charlotte and Beth were laughing now. Noy uncontrollably. But they were clearly having fun.

"You do like dresses...don't you?" Beth asked.

"I...but...well yes...but "

"Then that's decided. Here's the first one". Charlotte reached in the bag, and pulled the dress out..."

"Do you like it", Beth smiled at me. "We thought you could wear it for work".

"Why don't you try it on...and show us" Charlotte suggested, helpfully. "Your legs are smooth now. It'll look perfect".

"Yay!" added Beth "It's dress time for Caitlin! Let's see how much of a sissy you really are! I bet you already have some panties on."


"Of course she does", said Charlotte. "She always wears them now".

So humiliating. My girlfriend and her friend, the girl who used to fancy me, shopping for dresses for me...Is this really happening!??

To be coninued.

Tuesday, 26 January 2010

It's Official. I'm in dresses

Ok. I know there are worse things that could happen to a sissy like me. I mean, I adore dresses, but to wear one...most of the time...that's another matter altogether.

I feel belittled. Humiliated. Feminine. And excited.

I know it's been a while since I posted. Things really developed last weekend, when Charlotte and Beth went shopping.

I thought they were shopping for themselves. But then I got the call...

"Hi Caitlin! I have some exciting news!!!"

"Hey Charlotte. What's happening"

"Well you know me and Beth are out shopping? Well we've found so many lovely things!"

"Sounds great".

"Super. We'll be round later to show you."

"okay. See you soon."

Little did I know...

Tuesday, 12 January 2010

Dresses and skirts for work

I just had this message from Charlotte...

"Hey Caity! Hope you're good. I hope you don't mind, but please take a look at the following items that the girls and I put together for you.

Every girl needs some staple items in their wardrobe...let me know what you think, and maybe we can go shopping on the weekend and keep building your wardrobe.

Imagine yourself wearing these, and let me know your favourites for guidance.

I love you honey! xxxxxxxxxxxxx"

Some smart work dresses...

My favourite dress of this selection...

Some skirts for work and after work...

My favourite skirt of this selection...

And two skirts for fun!

And then I got this message from Charlotte's friend, Rachel...

"I hope you liked the last two skirts Charlotte sent over! I own two just like them, and I'm donating them to you because they're too small for me (Charlotte tells me your figure's coming along nicely). I can't wait to see you in them, my lovely sissy. Just don't forget to cross your legs when you sit!!!"

I can't believe how embarrassing this is getting (although I love the outfits Charlotte - thank you).

My favourites are the last dress (the flared shift dress - I think it would feel wonderful on) and the last skirt (the hip-hugging one - looks so comfortable and stylish)...what do you think???

Sunday, 10 January 2010

Charlotte and her friends.

Something that's REALLY been on my mind.

A few times recently, Charlotte's told me that lots of her friends know what's happening to me. I imagine her whispering to friends, and them giggling along with her in a mixture of shock and amusement.

This scares me.

It's one thing to be on this journey towards spending the rest of my days as Charlotte's girlfriend, in pretty skirts or dresses, make-up, long hair etc. It's another thing to think that she's already discussing this with her existing girlfriends.

Two of her friends have now even donated items to my new wardrobe. Sophie (who used to fancy me!! What must she think now?) donated these skirts...

,,,with a little note, "Dear Caitlin, I know you used to love the pink flirty one on me, but there's also a smarter skirt for the office, when you're ready. Can't wait to see you in them soon! Adorable. Charlotte says you'll be joining us on our girlie nights out before long! Remember, if you need any guy advice, call me."

I mean, guy advice!? What's Charlotte been saying to her!?

And then Karen donated this dress...

No note, but Charlotte's already teasing me about wearing this to work once I "grow into it". She also said that when Karen next comes to the flat, I should wear this for her!

The thought of all her friends knowing, AND contributing. It's too much to take. They KNOW I'm a sissy. They know and they're helping it happen.

Women I would LOVE to be...

...for a day, a week, a year...forever!

I dream about attending office meetings dressed and looking like this...what a different, feminine world it would be!

Love her slinky dress and smile. This dress must feel wonderful to wear, and it suits her so well. This is one of my favourite looks I've seen on a woman.

I adore the pink skirt and the dainty pose. To spend my days dressed like this, looking so adorable...

Is this a before, or after shot? Judging by the smile, I think after...

Just's your wedding and all of your girlfriends come round to get you ready. I'm imagining this is Charlotte, Beth and their friends dressing me...

"Oh Caitlin, you're such a sissy, but you will look wonderful in your dress. Shame you didn't come up to scratch as a man, but what a pretty woman you've become. Tom's going to love you in this dress..."

Loving the delightful pink dress. I bet she turns so many heads, all of the time. I like to think she's an intelligent, beautiful, powerful and feminine woman.

I love the way she's being held by her man...feminine and happy in her long summer skirt and beautiful hair. So secure and satisfied

Monday, 4 January 2010

More photos from Charlotte...

After her last comments about the dresses, Charlotte sent these over with a text message...

"I love this photo...don't you? How would you like me to help you into a dress like this..."

With this comment...

"...hmmmm...I wonder what the occasion would be!? Party? Work function? First date...perhaps someone will be undressing you later...before you kneel at his your pretty bra, panties and suspenders...looking into his eyes...needing...wanting..."

"Or maybe this one...oh what a gorgeous dress you're, let me help you into it, my little sissy girl. He's going to love it!!"

"Regarding your dress choices...."

Just spoke to Charlotte…she called from work. This is how the conversation went.


“Oh hi Sweetie…Caitlin. Aren’t you a suprise!!??”

“What do you mean”

“I didn’t know you’d take this so seriously…I mean, I didn’t think you would really try and put yourself in a girl’s position! We loved the dresses…didn’t we girls?…but the comments as well…wow!”. Charlotte chuckled, and I could also hear laughter in the background.

“You asked me to …”

“Oh Caitlin. Of course I asked you. But we have some talking to do. I mean, your comment for the wedding dress, the last one…’Imagine…my big day! All eyes on me.’…so cute.”


“Oh it’s ok honey. We loved it. And the other comment talking about a first date…with who!? You like boys now..?”

“No…I mean…no…”. I was stuttering.

“You’re already imagining yourself on your wedding day…cute dress…hair…pretty lingerie….”


“I guess it’s only natural for a girl to fantasize a little…isn’t it Caitlin?”

“I don’t like boys!” I cried.

“Hmmmm. I think the lady doth protest too much. What do you think girls?”

I heard a ‘yeeeeeessss’ and laughter again in the background.

“Anyway, have to go. Work to do. We can have a girlie chat tonight, and you can tell me all about it.”


“By the way, I thought the little pink number would look just darling on you”.

“Shhhh Charlotte. Your friends at work will hear”.

“Oh honey, they know everything! Everything!” she giggled. “In fact, Beth and Sophie want to help you out with some of their old clothes. We’ll have that wardrobe full in no time, to add to your skirt…so exciting. Speak to you later” Click.


What do I do!? Before I got together with Charlotte, Sophie used to fancy me. What will she think now!? And Beth, she’s gorgeous. The thought of Sophie and Beth AND Charlotte getting involved. AND giving me some of their clothes. This is moving way too fast…although I do like the knee length pencil skirt Beth was wearing the other da….WHAT’S HAPPENING TO ME!

I don’t know what to do!

Sunday, 3 January 2010

Charlottes Options 2

Message from Charlotte...

"Here's another lovely option for you..."

"Notice she has longer, brunette hair, not like my last suggestion. A more intelligent, gentle and feminine look...I'm sure you'd love to be sashaying around in that pretty dress, looking so cute and appealing to the opposite sex...if you looked like this, we could go on girly nights out together...maybe find you a cute guy toflirt with..."

Oh my ... Charlotte's now talking about guys...

I want to be...Rachel McAdams...

I adore this woman. I want to be her...wear the clothes she are some photos that explain why (self explanatory)

My favourite quotes from Rachel McAdams...

Talking about the clinging print dress above..."In the best dresses, you can move the way you always do. This is one of those dresses" "I love it when a dress seems to cling to you but not in an uncomforable way. This dress is very comfortable but sexy. It sort of looks like an oil painting. I'm usually in a comfy sweater and a really casual skirt."

I love it when women talk about their relationship with skirts and dresses...gorgeous.