And now dresses...!

Okay…here’s a text I’ve just had from Charlotte:

“Thanks for the skirts Caitlin! Me and the girls had fun looking at your choices. Most enlightening - you actually have some taste… although I'm sure half the time you were as focussed on being the girl and wearing the skirt, rather than just the skirts. Interesting.

Now do the same with dresses - imagine you can choose any nine dresses you want, and let me know why. Put yourself in a girl’s position (can’t be that hard for you!). xxxxxxxxx"

The dresses I’ve chosen are below…

NUMBER 1
I love the sophisticated look of this dress. The waist-tie is so cute too. Very sleek, feminine and the thought of the silkiness on my skin...mmmmm



NUMBER 2
Imagine...my big day - all eyes on me. Looking stunning in this gorgeous wedding dress and girlie tiara...Charlotte as my bridesmaid...



NUMBER 3
I love the netting detail on the bottom of the skirt here. And the heels. I'm imagining wearing this as Charlotte gets married to a real man. She looks at me, smiles and whispers, "my pretty sissy".



NUMBER 4
More sophisticated look. I like the floatiness of the dress, the inner lining caressing my legs with the see-through overskirt floating above. Divine.



NUMBER 5
Much flirtier, and I love the feminine bow. Looks like a great dress for dancing in, although would have to mind no-one gets a peak up my skirt at my pretty panties...



NUMBER 6
A first-date dress perhaps??? I love the pink ruffles in the skirt. Very feminine. I adore pink!



NUMBER 7
The perfect dress for summer walks on the beach. Light, floaty and feminine.



NUMBER 8
Party dress. Oh why must real girls have all the fun. Charlotte has a dress just like this. I dream about wearing it from time to time.



NUMBER 9
A grogeous white dress for a ball. Imagine dancing up close against your partner, sily skirt flirting with your knees. Delightful heels. Stunning.

Favourite skirts...

After the skirt incident (see below, it’s now in my wardrobe!), Charlotte has asked me to list 9 skirts that I like. I told her that it's not that I don’t like the skirt (it’s just I’ve [hardly] never worn one before), but she said that if I don’t want to wear it now, I should pick some others so she has some ideas for the future.

This is difficult for me (because there are so many to choose from, but also because I feel slightly humiliated!), but here are nine skirts, and why I like them…

NUMBER 1
I just ADORE the preppy look on this skirt. The little ribbon tie-up just adds to the effect too.



NUMBER 2
Short skirts = flirty. Flirty = fun. This picture seems to epitomize this feeling. It's not a sexual thing (honestly Charlotte) - it's attitude. Fun and flirty. In skirts.



NUMBER 3
Okay. I admit. This one's as much for the girl as the skirt. But not for the reasons you might think. She's clearly having SO much fun with the skirt...wearing the skirt...feeling the skirt. She LOVES her skirt, and just the satisfaction of being a woman, in summer, wearing a gorgeous summer skirt. If this is my future, I need to adopt (or learn) this attitude.



NUMBER 4
I love the contentment in this photo. It's summer, she's being held by a genuine alpha male, feeling him press up against her...she looks so happy and relaxed. I love the simplicity of her knee-length white skirt.



NUMBER 5
I just adore this skirt. Is she thinking...is she happy...is she sad? It's not easy to tell, but the thought of spending my summers in this kind of attire...a pretty pink skirt...ok I admit it appeals.



NUMBER 6
Skirt shopping...I guess I'm going to experience this soon. I love the femininity of this skirt...pink, pretty, frilly...and I love the smile on her face as she imagines wearing it.



NUMBER 7
I just like the thought of going into work in a tight, charcoal, double pleated skirt. Walking into the office, the women wondering where I got it, and men adoring me...the eroticism of being a smart, sexy , intelligent woman. I adore smart, sexy, intelligent women, and this skirt speaks to me of those attributes.



NUMBER 8
Work skirt? I'm not sure. Certainly fun and flity, but also professional. I love the side pleats. If I'd ever worn a skirt to school, it would probably have been like this. I think I missed out!



NUMBER 9
Mmmmm...gypsy skirt, summer, flirty. I can imagine twirling around the park in this skirt. I love the skirt, and the smile together. Contentment, with her man. Adorable.

Charlotte's option 1

So Charlotte just sent me this message...

"I think we need to discuss the future. With so many options for your look, which do we pursue?...I'm going to send you some pictures over the next few days. Take a look, and let me know which one you like best...for your future.

This one's a bit 'Barbie', but we CAN get you there if you like. Your hair is already almost shoulder length, and you do have a slender frame (i.e. you make a pathetic male! But you have the beginnings of a cute female)



"Look beyond the cute denim skirt and tight breasts. Imagine how great this figure would look in PRETTY DRESSES and SKIRT SUITS for work, GORGROUS OUTFITS...being this pretty can really help you get ahead (it's worked for me) - let's face it, your career so far has been a failure as a man - turning you into a cute girl might also be a great financial move for us...think about it".

Charlotte says she's going to post some more soon...

I want to be...

The one in the green top...



I've always liked the denim skirt look on past girlfriends. Charlotte now says it'll be an option for me. Here's the empathy bit Charlotte asked for...

I love the look of the girl in the green. She's so pretty, and looks so at home and comfortable in her tight denim skirt. I imagine going out with my girlfriends, walking up to the bar in this outfit, and feeling multiple pairs of eyes on me...wanting me, because I'm such a cute, adorable girl.

A little humilation...

Because I didn’t wear her present, Charlotte’s asked me to post a picture of the panties I’m wearing today. She’s going to check later…

Here they are:



And yes, unfortunately, everything I have does fit in there (much to Charlottes amusement!)

Hopefully none of my workmates will see this...

Lovely blog...

I wanted to direct your attention to this quite brilliant blog!

Among so many others, here's a super-cute outfit that Charlotte and I adore...



Monika is GORGEOUS, and has a great sense of style - a real inspiration! Check her blog out here (cut and paste):

http://stylefilter.blogspot.com/

Does anyone else know of any similar inspirational blogs?

The Skirt...(2)

Charlotte just got back. She came through to the lounge, where I was.

“Hey babe! How’s my girl!?”

“Er…I’m okay” I replied. Charlotte was wearing a cute flowing skirt and fitted purple blouse. She looked amazing, as usual.

“Oh…Where’s your present?” she said.

Charlotte looked a bit disappointed. I left the skirt on the bed. Hadn’t even touched it.

“Er…upstairs”

“Okay Caitlin. I know you’re probably not ready for it…not quite yet”

“What do you mean, not ye…”

“Shhhh honey”, she interrupted. “It’s okay. Just pop it in your wardrobe. There’ll be plenty of room in there soon. There are a few things we need to do first anyway. But all in good time. What’s on tv?”

All in good time? And there’ll be plenty or room in my wardrobe soon…? What does that mean? And if I’m so worried (and I really am), why am I also a little excited?