Sissy Bridesmaid

One of Charlotte's friends, Ruby, is getting married this summer. To a man. A real man. You should see how the women in the room react when he enters a room. They're all smiles and fluttered eyelashes. Including Charlotte.

Anyway, Charlotte's been asked to be bridesmaid for Ruby, which makes it about the twentieth time she's been a bridesmaid.

We were in bed last night, both of us in our Elle MacPherson nighties, her snuggled up behind me, when Charlotte brought the subject up...again.

"Maybe if you ask Ruby nicely she'll let you be a bridesmaid too", she whispered in my ear gently.

Ruby knows about me. Most of Charlotte's friends know.

In response, all I could do is reach for the hem of my nightie, and blush.




"Just imagine", she continued. "You and I, in our pretty dresses...helping the bride get ready....she wouldn't mind...it's not like there would be any men in the room. Just us girls. You'd like that, wouldn't you?"

At this point I knew she was teasing. I wanted her to stop. I also wanted her to go on.

"And then, at the ceremony...gliding up the aisle with our flowers...all eyes on the bride and us bridesmaids. The women admiring your dress. The men admiring you and I...wondering if we're single...available."

"Please Charlotte, stop messing".

"I'm not messing around. This could happen...this summer. You, in the cutest, prettiest bridesmaid dress...the envy of the other guests..."




"Can you imagine watching me dance with the best man afterwards...sitting on the edge of the dancefloor...with you cutesy dress and pretty flowers in your hair...on your wrist? A real man would stop his girlfriend. But you're not a real man, are you?"

"Charlotte..."

"Shhhhhh honey. It's okay. I know. You could just watch, as we danced close...cheek to cheek...weddings are so romantic...as he moves in for the kiss...his lips brushing mine...holding me tightly...a man, giving me what I need...the attention of a real man."




While you just sit there, watching...hands in the folds of your skirt...looking down at your pretty skirt and flowers...while I kiss him...and think about later...what I want to do to him...with my lips...my tongue...what he might do to me...with his...his...mmmmm"




"A sissy...while your girlfriend makes out with a hot guy in front of you...you know what could happen next... What will happen later...but you do nothing...why?"

"Please...pl..."

"Why Caitlin...why?"

"Because you deserve a real man...not a sissy..."

"Shhhhh...don't be upset. You said it Caity...my sissy....my pretty girl. You'd make an excellent bridesmaid".

I would. Her sissy.

"I'll let Ruby know". And with that she rolled over to sleep.

Gulp.

Women I'd like to look like

Since starting this blog Charlotte has always asked me to look for role models and post pictures of them. I've always admired and identified with strong, independent women (the opposite of me). However, this post is almost solely about looks, and lists some beautiful pictures of women who inspire me with their looks...

Erin Heatherton...firstly I love her hair. I'm a natural brunette, but the idea of going blonde for a short while appeals. And I adore her cute nightie...




Mila Kunis...there were so many pictures of Mila, so I chose one thatnwasn't posed. When I look at Mila, there's an internal battle going on...do I want to be with her, or do I want to look like her. I guess you can imagine which wins...?

I think she's elegant and incredibly sexy. I love her outfit (I want that skirt, and the shoes) and just her entire look. I watched Black Swan a couple of weeks ago, and I suspect we're going to see alot of this lady.




Sarah Chalke...an unusual choice perhaps. However, it's the picture that does it for me. The combo of a beautiful woman, intelligent and sexy...I LOVE her dress, and the pose. If I close my eyes I can imagine the dress hugging my body, shoes clicking as I walk to my next appointment. I want that dress!




Julia Restoin Roitfeld...I have no idea what this girl might be famous for, other than the way she looks...which is divine! The leather pencil skirt is amazing...completely unpractical, completely hot. I think she's facially gorgeous too...




How can I write this post and not include Natalie Portman? I would love to own the dress she has on in the photo below. It's so flirty and it seems to lap around her legs deliciously. She has a body to die for... So petite and feminine. Incredible, and an inspiration to sissies everywhere...

Anthropologie Wish List

Charlotte's decided that I need to take my wardrobe more seriously.

I've been following quite a few Anthropologie blogs for a while now, but now that my future as a woman is decided, I've taken a deeper interest.

I honestly think Anthropologie clothes would make any boy with even slight sissy tendencies want to throw away all their male clothes and spend forever in cute, pretty dresses, skirts and cardigans.

Anthropologie clothes are SO pretty and feminine, Charlotte thinks they're perfect for a someone like me. And she loves them too (and already owns a fair few outfits).

So she's asked me to share a few items with you...clothes that she's picked for me to wear in future perhaps. We haven't bought any of these yet, but they're certainly on the wish list.

Firstly, the Latticed Weekend skirt, based on a simple pencil skirt. This skirt is so cute. Charlotte lovew the pocket detail, and told me she would wear it on a date. Cue lots of blushes. Anyway, I adore this skirt. Very simple, flattering and feminine. I bet it feels gorgeous on.




Next, the hot Dusky Dunes skirt. I love the colour, and the figure hugging shape. It think the layers work really well, and it I can already imagine it encasing my legs as I walk down the street towards my office. I think this skirt is a dinner date with the girls item, an experience I might have to get used to (I've already been invited).




Soft Sakura pull-on style skirt, with chiffon underlay. I like the way the underskirt pokes out (so pretty) and I think the flower detail is really cute. Definitely feels like one for the summer...possibly walks in the park, or in the city. I'm sure this skirt would attract lots of attention, and envious glances from other women who'd approach me to ask where I bought it...




Love the pretty detail...





Tied Down dress with a pretty cowlneck feature. Charlotte says she can already imagine me in this one. I adore the neck detail. This dress is SO feminine. Lovely with pair of heels, my hair down and some cute jewellry. Maybe this will be my first Anthro purchase...




Canopy Lookout dress, with cute eyelet hem detail. Another very cute dress, probably a holiday dress. The eyelet detail around the hem and neckline set this off, but what makes this dress for me is the flash of colour on the belt. I imagine wearing this walking along the beach, hand in hand with a special someone. Its a very romantic dress...







Quiet Blush dress, shirtdress style with a hint of feminine pink. Blushing quietly is exactly what I'd be doing wearing this dress. Probably the cutest shirtdress I've ever seen. Very pretty. I think this is a dress I'd wear shopping with the girls on a hot day. Or maybe to the office...







Pezza dress. Very romantic, another cowlneck dress. The bust and waist detail looks very flattering, and it just looks like a very cute, submissive, demure dress to wear, which appeals to someone like me. I imagine wearing this on a double date with Charlotte, which Charlotte's just read and thinks is hilarious!




Sunday Shopping skirt. A line cut with a very cute bow. This reminds me of a grown-up version of a skirt you might wear as a little girl. Very feminine. I love the bow - it really does make the skirt. Another skirt I imagine wearing on a shopping trip, or to pack for a holiday in the sun. Charlotte thinks this one is very 'me'...




Verdant Stitches skirt. The lace detail is very cute on this skirt. I can easily imagine myself sitting next to Charlotte, wearing this skirt and playing with the hem as she teases me for being such a sissy...




Washi Wrap skirt. This feels like the kind of skirt I would wear to the office. And get lots of compliments from the other women. The wrap style is very appealing...showing perhaps a flash of suspender as I cross my legs and readjust my position. Another very cute skirt...




Finally, this seriously pretty Anthro slip. Charlotte's already teasing me about buying it for my birthday to lounge around in. And asked if she can borrow it for her next lawyer weekend retreat. Another lawyer in her firm aked her out last week...I can't stop thinking about Charlotte wearing this slip in bed, making out with a real man. His hand rising up her leg... A thought that terrifies me, but would also validate my true sissy nature. Charlotte can only smile at that idea.




In summary, super cute clothes from Anthro. There are two stores in London, and we're apparently going to both on the weekend. I'll report back next week. Hopefully Charlotte won't humiliate me by outing me to the sales assistants (although I'll be sort of disappointd if she doesn't!)

Later...

Outed by women

I think a lot about how Charlotte spotted my 'hidden' side. How did she know that I would be more suited to a female lifestyle? A life as a woman.

Some things are obvious.

Our sex life was good, but without being graphic, I could never please her the way you'd expect a man to please his wife. I simply wasn't well endowed enough (and for those of you that would say it doesn't matter, it definitely does to many women...for Charlotte it's psychological rather than physical). I could please her in other ways.

But there's always more to it than sex.

There were other subtle signs for Charlotte too. But more of that I will cover another time.

What's particularly interesting, is that other women picked up on it, even as far back as school. There are three instances in school that spring to mind:

1. My Ex-Girlfriend and the Skirt

One of the prettiest girls in my class used to fancy me at about age 14 (like I said, I am good looking in a kind of teen-boy sort of way). We went out for a couple of weeks, but she ditched me for another guy very soon when nothing physical happened between us (I'm talking kissing here!).

About a year later she came up with the idea that for charity, for a single day, boys and girls should wear each other's uniforms. For the boys, that meant an above the knee, dark school skirt, like the one below.




Now one indication of my true nature was that this idea aroused me. Fascinated me. But she could never have known that, when she looked at me and said, without missing a beat, "you'd like that, wouldn't you? Maybe you could borrow my skirt." We were the same size. It would have fitted.

People laughed, but no-one ever mentioned it again.

But she knew. Even if it was deep down...she knew. Perhaps it was because I was too afraid to kiss her when we went out. In any case, she could sense that I wanted nothing more than to go to school in her skirt, even before I did.

2. Sexy Legs

The second incident was in a mixed games lesson. We were playing basketball in the gym, boys and girls. I was 16.

There were several mixed teams, but only two playing at a time. While the other teams were waiting for their turn to play, they sat around the outside of the court.

After playing, I sat down next to the hottest girl in year, and her friend (also hot). She was on my school bus and I knew her well. We'd been friendly in the past. They were both looking hot in their short games skirts.




As I sat down, she said, "we were just talking, and you have the sexiest legs in this room".

I was really pleased. Two hot girls in my year both agreed. My legs were REALLY sexy.

I just said, "thanks".

Then she said, with absolutely no effort to be funny, "I'd love your legs. So slender and toned".

To which the other one said, "next time we play, you should wear a skirt too. Your legs are so pretty".

Of course, being a submissive male, I just smiled and turned beetroot red with embarrassment. All I could think about was me, my femiine legs...in a cute skirt...




Neither of them gve much thought that I was a man...just that my legs were objects of desire...for two already attractive women who wanted legs like mine.

3. An Opportunity Missed

A few weeks or months later, I was on the school bus sitting next to the same girl. The one who told me my legs were great.

We always got on well...talking and laughing on the bus, but with never a hint of romance. I definitely fancied her.

All of a sudden she just turned arond (completely out of context) and said, "I'd love to dress a boy up as a girl. There is no way my boyfriend would let me though."

Her boyfriend was a hunk.

Then she looked straight in the eye and said, "would you let me dress you up as a girl? Will you?".

If this was merely a fantasy served up for this blog, next I would have answered 'yes', and the next evening I'd be in her room, with her picking out clothes for me and telling me how gorgeous I looked in her favorite dress.




Instead, I just said meekly, 'no'. She looked disappointed for a moment, put her hand on my knee, squeezed it, smiled and said, "of course not". Then she changed the subject.

That night she went home to her boyfriend...a real man. And probably never gave me a second thought.

----------------

So that got me thinking...what is is that outed me as a sissy to these women?

I got the sense it was subsonscious...pheremones or something. I didn't move or act effeminately. I was certainly the opposite of an alpha male, but not as clear cut as you might think. Some women actually found me attractive, but these hot woman spotted me for what I am...a sissy destined for skirts, lingerie, long hair and makeup.

Regardless of my experiences, I think women are amazing...they know, often before we do...they knew before I did...hence my experience with Charlotte, and at school.

Outed as a sissy. Marked for womanhood.

Telling people about my situation...

First of all, thank you for all the messages of support I've received since returning. From people in a similar situation to me, but also quite a few real women who are interested In my transition (thank you in particular to Rachel and Katie for the compliments on my clothes, although most of them are chosen for me!)

I had no idea so many of you actually looked forward to my posts. It's really sweet. Thank you

Reality is dawning.

I had awful nightmares last night (although I had the consolation of waking up in my cute Elle MacPherson nightie that Charlotte bought for me - see below) - about what people who don't already know about my journey will say when they find out what I'm working towards...well...a life in skirts and dresses.




The people who know so far are female friends of Charlotte (to whom I'm a complete novelty, and after the initial wariness, am sort of endearing to) and some male and female colleagues of Charlotte's at the law firm.

Charlotte told me her male colleagues think it's funny (one has already hit on her after finding out). Her female colleagues (most of whom have never met me) are completely intrigued, and ask her about me every day.

But what about MY friends?

I have lots of guy friends who have no idea what's going on. You would think my hair might give them a clue, but loads of guys have long hair these days, and it's always tied back when I see them, so they never see the styling.

Plus I have a few female friends who I'm sure would properly freak out if I told them.

The reaction from Charlotte's friends when they find out is ALWAYS the same.

Firstly shock and surprise...




Amusement, especially when they meet me again...




Curiosity, while trying to hide amusement...




Acceptance, which is always at the same time they realise you're no longer a threat...not a man, but a woman, like them...





Lots of questions, once again, with smiles and stifled laughter...




Then always a desire to help. An overly keen desire to help, particularly with clothes (especially dresses and skirts) like I'm a dress-up doll for their amusement...




Plus lots of questions for Charlotte...everything from her future plans ("are you going to date men?"), my past performance in the bedroom ("what was he like...?") through to simple emotional support for her ("are you okay?").

I think it says so much about how fantastic most women are that they always seem to end up wanting to assist in some way.

However, those responses have come from Charlotte's friends, many of whom don't know me very well. I'm sure my friends will react very differently.

So I guess the point of today's post is to ask for help...

Have any other sissies told their friends? How did they find out, and what was their reaction? How do you think I should break the news, sensitively (I don't want to just jump out in a little black dress and yell "surprise!").

My new skirt and dress

I had to share this with you.

To celebrate my return to sissidom, Charlotte bought me a present from. Anthropology...




I'm wearing it now, as we watch a dating show together on the television (lots of pretty girls...with real men) with my fluffy lilac sweater from Forever 21. I also have a flower in my hair (it is Saturday night after all!) and some light make up on.

It feels strange, us BOTH on the sofa wearing skirts again after all of this time. Nice though. Charlotte's in a simple black jersey skirt and white vest top, looking effortlessly stunning as always (I know she'll read this later!).

Anyway, I mentioned a skirt AND a dress...

Charlotte's friend Sophie popped around earlier with a present of her own. I'm pretty sure Charlotte put her up to it. Sophie works in a boutique dress shop, and gave me this...


"It's for work...when you're ready", she giggled. "It's not new. I bought it last year. But it's not worn, and it's super cute. Your colleagues will love it".

I told her that I'm not wearing dresses to work...I've not even thought about it.

"It's fully lined and it'll complement your shape". It's true, Sophie and I are actually now the same size, and a similar shape.

Most of Charlotte's female friends know whats happening now, and lots of her colleagues have known for ages.

"You'll have to start being yourself at work soon too. We have so many lovely work outfits in at the moment. You should pop around with Charlotte...when you're ready."




I couldn't say much in return. Just play with the hem of my skirt and look grateful. Sophie used to fancy me...look at us now...discussing dresses and skirt suits!

Like girlfriends...So humiliating.

The last time I went clothes shopping with Charlotte I was completely humiliated (see an earlier post).

But I know this is the real me...before long I'll have to face some changes at work...

Charlotte and I

Now that my future is settled, Charlotte has been letting some more of her friends and colleagues know about our, or my, 'situation'.

You have to idea how truly humiliating it is. I've heard her on the phone laughing with her friends...always behind a closed door (never in front of me).

The most obvious question you might be asking is, "why is she laughing? Hasn't she just had it confirmed her man is a sissy. Even after making a massive effort to be a man for her. What woman wants a sissy for a boyfriend?"

That's true. Charlotte is SO beautiful. She's always attracted...well...alpha males before we were together. But I was always called a pretty boy. Pretty like her.

The reality is that Charlotte is exactly like 99% of women out there. Physically and sexually attracted to real men. Not wimps.

She needs this...





Certainly not me. Not in that way.

What woman wants a sissy as a boyfriend?

Some perhaps. But not Charlotte, that's for sure. The longer we've been together, the more it's been obvious to me I've never been Charlotte's usual 'type'. Our relationship has always been so much deeper than merely physical.

We're so close.

It was Charlotte that helped me explore my submissive nature. She spotted it before me, and together we've taken it through it's natural course. She's uncovered the real me. Someone so much better suited to being a girl, than a dirty, hunky man. With long hair, pierced ears, a pretty smile, dresses...humiliation...peace in myself.

Not a big, grizzly, hunky man.

Then there's our sex life. I've never been able to satisfy her the way a real man would. I've always been smaller than most. Much more likely to elicit a reaction like this...




Amusement, sometimes disappointment, embarrassment but most of all, laughter. And sympathy. And friendship. Whereas Charlotte needs someone with a package that can elicit this reaction from her...flirtiness...




Or sheer lust...




So moving forward...

I love Charlotte with all my heart. I'm 100% committed to her. And I know she loves me too. And is committed to my happiness. We live together, and we're still together. And we plan to remain together on many levels.

But I can't hope to keep her happy in every way.

I'm more of a girlfriend. An adoring, loving, girlfriend. A submissive, embarrassed, adoring sissy in pretty dresses...




A woman like Charlotte needs to be wanted by a MAN. She needs masculine, alpha male attention to be the woman she is. And above that, SHE wants a man. She needs to be dominated, to be desired, to feel submissive, to be taken...



I desperately want to be that man, but it's clear from Charlotte that I will never be the type of man she needs to fulfil her needs.

From time to time, she'll need someone like this...



The scary thing is...to continue on the road I'm on, Charlotte's convinced that from time to time...to be a true woman...I'll need a man too.

To be wanted...to be desired...to please...to treat me like the woman I need to be. To be truly happy.

Charlotte and I are still talking about the future. There's no doubt she wants to see me have that experience. That she wants to see me fulfilled. as a woman.

And what do I want?

I want Charlotte.

But there HAS been a switch in my mentality. The way I see myself. My role in the world.When I see pictures like the ones below, I have a new reaction...in my mind, I'm no longer the man in the picture.

The are two alternatives...

1. Charlotte is the woman in the picture. She is desired...loved... adored...submissive...I love her so much, I need heed to be fulfilled. I am the one taking the pictures. She loves me...she needs him.

2. I am the woman, with Charlotte taking the picture. Which I find scary, humiliating, and arousing.

Picture 1

In sweet lingerie, snuggled up to my man..close to him...his manhood brushing my cheek...him playing with the lace on my panties...Charlotte encouraging me...smiling...instructing..."undo the button...slide your hand in...take it out...that's it...gently kiss the tip...run your fingers along it...open your mouth...wrap your lips around it...taste it...good girl..."




Picture 2

Wearing a dress Charlotte bought for me. Being sophisticated, wanted...a kept woman...playing the role of housewife, keeping my man happy...Loving him...needing him




Picture 3

On a double date. Charlotte in the row behind, making out with her date...in between her kisses, whispering to me as I kiss him back, his hand moving up my leg towards my skirt...Charlotte gently whispering in my ear..."sissy....sissy...my sweet girl...just do what I do...let him touch you...kiss him gently..."




Charlotte will read this later and laugh.

And then she'll decide what's next for me...for Caitlin.