Sissy inspirations

I'll report back on my gym experience last night later in the week (I'm still working out what it all means - so humiliating), but I wanted to post the pictures I sent to Bess, my new personal trainer.

To remind you, these were the pictures she asked for, via Charlotte, that would help her design my training program. That is, in an ideal world, what would I look like to look like. Or more accurately, what would Charlotte like me to look like.

They also left Bess under no illusions on where I'm heading. That I'm a sissy, looking to take my body closer towards the ideal feminine shape. Just like her. Just like Charlotte.

To look great in skirts and dresses.

To look pretty in nice underwear.

To look attractive in strappy tops, high heels, strapless dresses or a bikini.

Here are my choices, and why...

Firstly, the look we're shooting for is, slender, toned, yet feminine. We're not interested in too many curves (unrealistic without padding or some hardcore hormone treatments), and definitely not the big breasted, buxom look.

Picture 1

The idea from this picture is to look good in dresses like this. The tightly fitted top and flowing skirt compliment my target shape perfectly. Arms are toned, waist is tight and the shoulder shape is perfect.





Picture 2

Once again, the inspiration comes from the outfit. The model is slender, but the shape is realistic from where I am now. I know from talking to Charlotte that I suit this dress shape well.



Picture 3

This photo is all about the proportion of the shoulders, chest and waist to each other. This is my ideal shape, and my goal is to look good in tight summer tops and little flirty skirts.




Picture 4

I have the office in mind here. Pencile skirts are a go-to item in most girls wardrobes, which is perfect for me with my boy shaped hips. Once again, she's in proportion, and her arms are toned without being too skinny.




Picture 5

Exactly the same here. I love the way her waist is accentuated by the choice of clothes, but in any case, creation of a nice tight waist compared to hip size is going to be my biggest challenge. I'm slender now, but I need bulking up in the hips and tightening up around the middle to reach my desred shape and look good in skirt suits.





Picture 6

Her arms are toned, but this picture is mostly about the flat tummy and shape of her body in the underwear. I imagine I'll be wearing stockings often for Charlotte under my skirts, and so I need to reach a shape that looks best with them.




Pictures 7 and 8

Her back is beautiful, and while her bum is small, it's nicely toned and carries off the underwear very nicely. Very cute.




Same from the front. You'd obviously expect it from an underwear model (duh), but what woman wouldn't want a body like this.




Picture 9

Pretty sure I've posted this picture before, but it's all about looking great in a cute shift dress, once again, likely to be a go-to item in my closet. For this I need a very feminine, but not too curvy shape, toned arms and toned legs.




Picture 10

I love this photo, because although slender, the model is very natural looking...not too toned on the tummy...a nice feminine shape and texture. I needd to look this good in underwear! She looks very desirable in this photo...




Picture 10

So Natalie Portman is OBVIOUSLY a sissy's DREAM. Although I think she was way too skinny in Black Swan (although amazing in the movie), I adore her petite build, slender arms and legs and tight waist. So what if she doesn't have big boobs (over-rated anyway)... I much prefer that look, and it's obviously more achievable for me with my boyish, slender frame.

Oh...I also love her dress in this photo! I want it! I adore the way the layers of skirt are wrapped around her legs.




Picture 11

This one is about her lovely slender legs and the way they show off her skirt so nicely. I'll be spending most of my time in skirts and dresses according to Charlotte, so I need legs that will want to see plenty of daylight, and are toned and slender.




Picture 11

She's a high end model, so perhaps the body is unachievable for me, but this is what I would love to look like in a bikini. The easiest bit of the photo for me to achieve is the bottoms, because I have a very small package and what I do have can be easily tucked away!




Picture 12

Hips are also going to be very difficult to sculpt from very little, but as a goal, this picture does nicely. When I pull my skirt up in the morning, I'd like to have something for the skirt to sit on nicely...i.e.some hips and a toned behind.




Picture 13

I adore the little feminine tummy in this picture...very sexy. Her legs are also perfect (the tops of her legs)...not too skinny, and very feminine.




Picture 14

Every girl dreams of her wedding day, but to look fantastic in a wedding dress takes a lot of hard work! I don't know what my future holds, but whether I get to wear a wedding dress or a bridesmaids dress, I'd like to aspire to achieving a shape similar to this pretty model.




Picture 15

Mila Kunis...the strapless look is going to be difficult for me to pull off without creation of a bust, which obviously cannot be acheived via exercise alone. However, as an aspiration, I would like to look this good in a pretty strapless sundress. I think she looks adorable!




Picture 16

Too skinny, but I love the way her hips are accentuated by the simple skirt. I need to be able to carry this look off.




Picture 17

Finally, Charlotte thought it would be funny to send this picture over to. Bess. We ordered this outfit for me for future gym sessions (when it gets very hot and sweaty, and a skirt would be more suitable), although it hasn't arrived yet.

I cam't believe I will be wearing this skirt in public soon! I'm going to feel like such a sissy... I hope the other girls in the gym don't think I'm a freak!

Basically, I need to look this good in a tennis top and skirt, not least because I may have to play the partners in Charlotte's firm once I'm ready for it.



In summary

I know what I want to acheive, but I'm really interested in any clothing advice anyone has for someone with my body shape, and what I should aspire to. I'm naturally slender, and am currently a size ten (UK)- that's a six in US sizes on the bottom, and a size 10-12 (UK, 6-8 US) on the top. So already pretty small. I have a chest size of 34A, working on getting up to a B!!! I'm 5ft 7...small for a man, and average to tall for a girl.

I'm particularly interested in dress styles that I should explore, who has nice items right now (as you know, I'm a big Anthro fan), and other advice for styles of clothing that might suit me.

Thanks for your help!

PS when Bess got my picture she sent me a text. All it said was, 'Thanks Caity. Looking forward to giving you the shape you deserve'. She's obviously a natural when it comes to sissy psychology!

Sissy workout

So, I've spent the last three months seriously trying to get in shape for the summer.

And I've lost a load of weight, but it clearly wasn't enough for Charlotte. It started last week with a prompt from Charlotte to join the gym.

"If you want to fit into some cute summer outfits you need to lose a little weight", she suggested.

"What do you mean", I responded. "I'm in pretty good shape".

"Hmmmm. Perhaps for a boy...a slender boy at least. But you're going to need some help with your arms and thighs...for...you know...your new clothes."

I knew immediately what Charlotte REALLY meant. She wanted me to tone them down...for them to less like a man's arms, and to look more like this...




That is, more like HER arms than his...







And for my legs to look good encased in a dainty skirt...



Or in some pretty lingerie...




But did I fight back when Charlotte suggested it?

No.

"Good. That's settled then"', Charlotte said, triumphantly, but also slightly disappointed, like she wanted me to fight back.

We headed for Charlotte's gym where began one of the most humiliating experiences of my life.

After signing up, making the most of the couples membership (Charlotte is already a member), we were asked by the gym manager if I wanted a personal trainer.

Before I could say anything, Charlotte smiled and said 'yes'.

The manager replied, "Great. Todd and Darren are both available later this week. Can I book you in on, say, Wednesday?"

I immediately thought of what Todd and Darren might look like. Real men. With six packs, muscles, and ... packing something extra...more than me...




Once again, Charlotte jumped in first.

"I think we might need someone...more...suitable...for ...his needs."

The manager retorted, "Todd and Darren are our very best madam. I can assure you they'll have your boyfriend up to scratch in no time".

"I'm sure they would. But I don't want him looking like one of those hunks on the wall. He needs...well...toning down. For the summer. For the beach".

By this time I was merely a blushing spectator.

Charlotte continued, "Is Bess free? She's been fantastic with me."

"Er...yes", the manager replied. "But Bess specialises in...er...women".

"Perfect. That's exactly the look we're aiming for. Isn't it honey?"

As you can imagine, by this time I was like a beetroot.

"Okaaaaay", said the manager, looking shocked. "If you want Bess, I can book you in for Tuesday. That's the only day she's in this week. Say 8pm?"

"That's fine", Charlotte said. "Although isn't 7 - 9 on a Tuesday ladies night?"

"Yes, but that's the only day she's in this week. And we can make a...er...special case", he said, looking at me. "Would you like me to change it for the week after next?" the manager suggested helpfully.

"No. It's fine. Tuesday it is." Charlotte glanced over at me, and smiled slightly.

After that I practically ran out of the managers office in embarrassment.As I left, I could hear him stifle a laugh, and Charlotte say, laughing, "I'd quite like a session with Todd..."

As I walked down the corridor I passed a photo of Bess on the wall. She looked remarkably similar to this girl...




She's stunning. Exactly the kind of girl I would have wanted to be with....not be like. Just my luck.

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I met Charlotte in the car five minutes later.

"Bess is amazing. And hot. She'll love you. You're going to look fantastic in a bikini...and that sundress I bought you". Charlotte was laughing now.

"Oh honey", she continued. "You're going to look so cute. We need to get you some workout clothes though".

"But I already have some", I said, meekly.

"Didn't you hear the manager dear? Tuesday is women only night. You'll need some more gym outfits...to fit in".

"What do you mean?"

I soon found out. When we got back home, it was straight onto the internet to look.

"Okay...just to ease you in, let's get these", Charlotte suggested. "My baby will need trousers and a supportive top..."

"But...these are for girls..."

"Exactly, my little sissy...don't cry babe, you're going to look super cute!"







"Plus a spare in case you get your purple one all nasty and sweaty..."



"Plus you'll also need some cute shorts for when it gets hotter..."




Okay...they don't look too bad. Almost unisex.

"And of course, a skirt for when it gets REALLY warm in there..."

"A skirt", I cried, "I can't possibly wear a skirt! Everyone will find out!"

"Find out what honey?", Charlotte replied, chuckling.

"That I'm .....a .....a..."

"What? A man? Someone who can look after me? Keep me? Support me? Make love to me? Go on...say it!"

"I'm a....a....a..."

"Say it babe", she whispered.

"A sissy..."

"That's right. You could have said a man. In which case I would have shut all this down and gone to a menswear outlet. But you said 'sissy'. And what do sissies wear?", Charlotte asked.

"Skirts".

"That's right babe. Skirts. Just like me. Skirts. You need some skirts for when it gets hot in there...when your legs get more toned....you're going to look so pretty."

"This set...this color is definitely you!"




"And the pleats on this are super cute..."




"A little ruffle skirt, to show off your new legs..."



"And another set...pink this time...so pretty."



"And finally a dress, for when you join me and the partners for tennis later in the summer..."

"The partners? How...how...can I wear a dress in front of the partners."

"Only the women partners first honey. Most of them know about you anyway...then once you get better, we can play the men! You need to look cute for them...". Charlotte laughed profusely, and chose this dress...




"You'll look SO pretty!"

That's where we left it.

With me completely humilited, taking my sissiness into public, again. Charlotte has already called Bess to let her know I'm coming, and Bess has said she's going to send over some more gym wear advice.

Plus I need to send her some aspirtional photos to help us design the workout program...Charlotte's offered to help.

At least there's no skirt ....yet

I'll update you later in the week, after my first personal training session with Bess.

Sissy daydreams...

Lace and ribbons. This dress could have been made for a sissy. Or a woman embracing her feminine side. I imagine blushing as Charlotte ties me into this dress ("my pretty sissy") after she's got ready for her date...she leaves me at home to think about the fun she's having with a real guy.




Or perhaps Charlotte leaves this dress out for me instead. It's approaching summer, which means shorts for the guys and sundresses for the girls and me. This is such a cute outfit...




Charlotte Chooses my skirt, lays me down on the bed and takes photos of her sissy. A very pretty skirt, for her sissy. Seriously though...is skirt is CUTE.




Daydreaming of one possible reality...I smile submissively as my man zips me into my figure hugging dress, the soft lining enveloping my body, screaming "sissy" with every caress as I walk hand in hand on my double date with Charlotte and her real man.




Why do I find it easier to concentrate in a pretty skirt. Does this also explain why boys are doing so much better at school these days? Answers on a postcard please!

Suggestion: all unruly boys to be put into cute skirts...




Strolling down the beach in a breezy, flirty skirt. Loving the feeling of my hair caressing my back, my skirt flapping at my legs. Having my photo taken...by Charlotte? By a friend? By a date?




Being held by a real man...pressed up against him in my tight, slinky dress. His manly hand covering the whole of my back, pulling me towards him. What's that I feel pressing against my tummy? Swoon.




Relaxing in the park in frills. Watching other people pass by. Other women in their pretty outfits. Couples arm in arm. Real men in shorts and shirts...and me in my pretty underwear and girly dress. Could I be like those real men if I wanted to? Not really. Not according to Charlotte, and she should know. She's seen me naked.




Choices...hmmm...which dress today? It's not hard to imagine opening my wardrobe to the sight of so many pretty clothes. To spend the day like every sissy should...in dresses.




To make out with a guy while I'm wearing a skirt...feeling him hold me...caress me...feeling every inch the sissy as I experience what Charlotte has experienced so many times before...conscious of the hem glancing me knee as his lips glide mine...




Such a romantic picture. All hope of me being the guy in the pic faded some time ago. Which leaves me in a beautful white party dress, gorgeous long hair, heels and a man to keep happy.




Such a pretty, fem pose to go with my pretty dress. I feel divine. I feel humiliated. I feel like a sissy.

The prettiest shorts...

This is exactly the kind of thing Charlotte would have me wear to remind me of the sissy I am.

So why do I find them so cute!?




Because I know they represent my future? And it's a future I'm becoming more resigned to every day.

Loving Ann Taylor right now...

Charlotte sent me a link to their website, with a message, "Hey babe! Lydia and I think this season's looks are very YOU. Xxxxxx"

Lydia is one of Charlotte's friends, who knows about my situation. Her boyfriend is a serious HUNK, and so she can't understand why Charlotte chooses to live with a sissy like me. Funny, because when I look at him, it's even more obvious to me (and Charlotte) why I belong in dresses...

Anyway, Charlotte asked me to think about work outfits, and I love the pieces below...





This skirt SHOUTS femininity with a capital F. I imagine what the girls in the office would say if I swished into the office in this! Very cute.





Smart and feminine, if I love the simple clean lines, and the dark colors go so well together. This look is very Charlotte (legal).




The detail on the blouse is very cute, and the leg hugging skirt is already whispering, "buy me...buy me".




A more casual knit and skirt look, this is definitely for a 'comfy' look day when you dont want to just slip on a top and skirt and not make that much effort.





Not so much for work, but I am a sticklet for a cute lace skirt. This is definitely the kind of skirt Charlotte and her friends would choose for me...





Apparently this dress sold out in 2 hours from the Ann Taylor NY store. It's easy to see why. Once again, not a work dress. More of a date dress I think...very cute.

I'd love to look like this woman!





I already own a dress a bit like this. A classic cut black dress with a cut that would never tire.




Okay...obviously not a work dress. However, I spotted it and I adore it. The bow really sets the rest of the dress off...a very cute bridesmaid dress.




Another pretty top and skirt combo, I'd love to dress like this to work...with a sassy pair of black heels...





Finally I wanted to add this as an option for how one could wear the skirt in pic one. I like the comtrast between the hard, masculine look of the jacket and the femininity of the skirt.

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BTW, as I was posting these, I thought "oh my god...I'd love to be one of these fashion models!"

Imagine if your job was to wear pretty tops, skirt and dresses all day!? Then I think, imagine if it was Charlotte behind the camera! I know the dieting would be hellish, but there aren't many women who wouldn't like to look like the women above and spend their time smiling into a camera looking pretty.

Then, think of the free clothes!

Caity
Xxxxxxxx