Wednesday, 4 May 2011

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!


  1. omg Cait you must feel soo humiliated and yet so compelled.. charlotte is amazing!.. oh how I envy you and yet I can only begin to imagine the knots that must be turning in your stomach.

    The idea of having a personal trainer dedicated to giving you a better girls bodyshape.. oh thats a superb idea! And she sounds like she is going to love really making you feel like such a girly girl. 'The shape you deserve....sissygirl'!

    These posts are very exciting.. I can't wait to find out how you got on in your first gym session.

  2. Thanks for your comment in my blog. I love your blog, is really sissy and femenine, your stories are very, very hot and the photos are fantastic. I amswer your comment in my blog. kisses.

  3. Caitlin,
    Those are all beautiful dresses, but what about your looks?
    Have you got a feminine haircut? Are your eyebrows plucked? If not, perhaps Charlotte should accompany you to her hairdresser. It wouldn’t surprise me if she already knows all about you and can’t wait to help make you the most beautiful of sissies!
    Are you wearing makeup to the gym? Please tell us all about you workout experience!

  4. Caitlin,
    These are all wonderful clothes, but what about your looks? Have you got a feminine haircut? Are your eyebrows plucked yet? If not, maybe Charlotte should accompany you to her hairdresser. It wouldn’t surprise me if she already knows all about you and simply can’t wait to help make you a most beautiful sissy.
    Are you wearing makeup to the gym? Please tell us all about your workout experience!

  5. Anonymous said...

    You'll look great in a PE type skirt, Caitlin.
    sissygurl belinda

  6. Love how you're working out... and your inspiration here! I'm inspired now, too (sigh!)!! Keep it up!

  7. Caitlyn: I absolutely love picture 3. I would give anything to be her and wear that cute, sexy top and skirt for just one day. She is exactly who I would want to be if I could get my wish and be a girl. Thanks for the wonderful posting you do...

  8. I really, really, really hope you come back to finish your story! I just love your blog!

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