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Caitlin's Diary

After five loving years of trying to give her what she deserves and needs, my girlfriend Charlotte finally suggested some changes in our relationship. Radical changes. Charlotte is pushing me towards my new self, including a newly found appreciation of fashion, cute hairstyles and femininity. In turn, my priority is to do what it takes to make Charlotte happy. To help her be the woman she is. My journey is humiliating, revealing, humbling, exciting and terrifying.

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Caitlin's Diary | caitlinsdiaries.blogspot.com Reviews
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After five loving years of trying to give her what she deserves and needs, my girlfriend Charlotte finally suggested some changes in our relationship. Radical changes. Charlotte is pushing me towards my new self, including a newly found appreciation of fashion, cute hairstyles and femininity. In turn, my priority is to do what it takes to make Charlotte happy. To help her be the woman she is. My journey is humiliating, revealing, humbling, exciting and terrifying.
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1 caitlin's diary
2 sissy inspirations
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9 picture 9
10 i want it
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Caitlin's Diary | caitlinsdiaries.blogspot.com Reviews

https://caitlinsdiaries.blogspot.com

After five loving years of trying to give her what she deserves and needs, my girlfriend Charlotte finally suggested some changes in our relationship. Radical changes. Charlotte is pushing me towards my new self, including a newly found appreciation of fashion, cute hairstyles and femininity. In turn, my priority is to do what it takes to make Charlotte happy. To help her be the woman she is. My journey is humiliating, revealing, humbling, exciting and terrifying.

INTERNAL PAGES

caitlinsdiaries.blogspot.com caitlinsdiaries.blogspot.com
1

Caitlin's Diary: Charlotte's Perspective on the Life of a Sissy

http://caitlinsdiaries.blogspot.com/2010/06/charlottes-perspective-on-life-of-sissy.html

Saturday, 26 June 2010. Charlotte's Perspective on the Life of a Sissy. I was talking with Charlotte a few days ago, about how she always seems to presume to know what I'm thinking and what I'm going through. It's strange, because obviously she's closest to what's happening with my transformation from boy to sissy and closer to girl. Even so, despite her patience, I can't believe she could possibly know what I'm thinking. When she got back, we sat down to talk. I said, a little shocked. For instance", Ch...

2

Caitlin's Diary: To be (a sissy), or not to be (a sissy)

http://caitlinsdiaries.blogspot.com/2010/04/to-be-sissy-or-not-to-be-sissy.html

Sunday, 25 April 2010. To be (a sissy), or not to be (a sissy). Imagine someone could assure you that in just a few months you could be living the rest of your life as a woman? Feminine, pretty, delicate, divine, happy and free. On the face of it, for a sissy, absolutely. But if you start to piece all of the implications together.anything but terrifying. For instance:. Would they be supportive? Would they laugh at me and call me a sissy, or just smile? 5 And this is the big one.losing the girl that I...

3

Caitlin's Diary: April 2011

http://caitlinsdiaries.blogspot.com/2011_04_01_archive.html

Sunday, 24 April 2011. 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. I'd love to look like this woman! I alrea...

4

Caitlin's Diary: Sissy workout

http://caitlinsdiaries.blogspot.com/2011/05/sissy-workout.html

Monday, 2 May 2011. 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". That is, more like HER arms than his. And for my legs to look good encased in a dainty skirt. I immed...

5

Caitlin's Diary: October 2010

http://caitlinsdiaries.blogspot.com/2010_10_01_archive.html

Sunday, 3 October 2010. Women Id like to be.Rachel Bilson. The latest in my series of women I'd like to be, I don't know how this one has taken so long. Rachel Bilson is a total fashion icon, and a real inspiration for someone like me. Who else used to watch the OC and think, "I totally want to be this woman.". Here are some inspirational photos. Okay, which one of you wouldn't like to be dressed like this. She's so stunning. I lover her hair and the outfit, especially the petticoat. The flared skirt on ...

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Caitlin's Diary

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