Put simply, my girlfriend Charlotte needs more than I can offer. I've tried being manly, but it's not worked.
After years of trying to give her what a woman needs and not succeeding, three weeks ago she finally suggested some changes in our relationship.
Originally a joke, she now calls me Caitlin pretty much all the time. I don't own any male underpants any more, just panties (not hers - I had to go out any buy my own).
I don't know where this is going, but Charlotte's asked me to keep this blog as a diary...Caitlin's diary. And she's going to check it once a week, and use it to determine the next steps in our relationship.
So who knows where this is going…it’s all up to Charlotte I guess, and she's already told me there will be plenty of suprises in store...
Call from Charlotte
Just spoke to Charlotte…she called from work. This is how the conversation went.
“Hello”.
“Oh hi Sweetie…Caitlin. Aren’t you a suprise!!??”
“What do you mean”
“I didn’t know you’d take this so seriously…I mean, I didn’t think you would really try and put yourself in a girl’s position! We loved the dresses…didn’t we girls?…but the comments as well…wow!”. Charlotte chuckled, and I could also hear laughter in the background.
“You asked me to …”
“Oh Caitlin. Of course I asked you. But we have some talking to do. I mean, your comment for the wedding dress, the last one…’Imagine…my big day! All eyes on me.’…so cute.”
“I…I…”
“Oh it’s ok honey. We loved it. And the other comments talking about first dates…with who!? You like boys now..?”
“No…I mean…no…”. I was stuttering.
“You’re already imagining yourself on your wedding day…cute dress…hair…pretty lingerie….”
“B..But…”
“I guess it’s only natural for a girl to fantasize a little…isn’t it Caitlin?”
“I don’t like boys!” I cried.
“Hmmmm. I think the lady doth protest too much. What do you think girls?”
I heard a ‘yeeeeeessss’ and laughter again in the background.
“Anyway, have to go. Work to do. We can have a girlie chat tonight, and you can tell me all about it.”
“Er…okay…”
“By the way, I thought the little pink number would look just darling on you”.
“Shhhh Charlotte. Your friends at work will hear”.
“Oh honey, they know everything! Everything!” she giggled. “In fact, Beth and Sophie want to help you out with some of their old clothes. We’ll have that wardrobe full in no time, to add to your skirt…so exciting. Speak to you later” Click.
—————-
What do I do!? Before I got together with Charlotte, Sophie used to fancy me. What will she think now!? And Beth, she’s gorgeous. The thought of Sophie and Beth AND Charlotte getting involved. AND giving me some of their clothes. This is moving way too fast…although I do like the knee length pencile skirt Beth was wearing the other da….WHAT’S HAPPENING TO ME!
I don’t know what to do!
Gorgeous dresses
Okay…here’s a text I’ve just had from Charlotte:
“Thanks for the skirts Caitlin! Me and the girls at work had fun looking. Most enlightening - you actually have some taste… 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…
Here you are Charlotte. As you asked. Please don’t show the girls in work…
After yesterday’s skirt incident (it’s now in my wardrobe!), Charlotte has asked me to list 9 skirts that I like. I told her is not that I don’t like the skirt (it’s just I’ve 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, but above are nine skirts, and why I like them…
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!)
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 an outfit just like the one above. Flats with a cute flowing skirt and fitted purple blouse.
“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 aroused?
![Charlotte left early this morning for work, and left a skirt exactly like this one on the bed. I just got a phone call from her…
“It’s me”, she said.
“Hi Charlotte”
“Hey honey…Caitlin” [giggle]
“Charlotte! Do you have to call me that?”. I was so embarrassed.
“That’s your name silly. Have you chosen my dress for Saturday yet?”
“Not yet. Getting there though.”
“Good girl” Charlotte replied. “Did you see the present?”
“What present?”
“The one I left on the bed”.
“The skirt? You bought yourself a present? It’s nice”.
“You like it????” Giggling from Charlotte, and then fainter, “He likes it!”. There was a soft sound of laughter in the background.
“Who’s there with you?”
“Oh no-one…just some of the girls in the office. Nevermind that. Back to the skirt. You like it?”
“I guess so. It’s nice”.
“So …you like the present?”
“Yes. You’ll look nice in it.”
“I would, I know. Exceeeeept…..it wasn’t for me…”
“What do you mean?” Could this mean…
“It’s for you silly!” More female laughter in the background…
“What do you mean, for me? And why are people laughing…are they listening to this????” I cried.
“Don’t worry about that. Let’s talk about your present later…I need to get back to work”
“Er…okay…Charlotte, I’m scared”.
“Oh, don’t be honey. It’ll be okay”. She sounded sincere.
“Okay. S…s…see you later. Bye.”
“Bye Caitlin…enjoy your present [giggle]”. Click.
And that’s how the conversation went. What do I do now!? She’s home in one hour. I’ll update you later.](http://25.media.tumblr.com/tumblr_kvf825MKiW1qac4quo1_400.jpg)
Charlotte left early this morning for work, and left a skirt exactly like this one on the bed. I just got a phone call from her…
“It’s me”, she said.
“Hi Charlotte”
“Hey honey…Caitlin” [giggle]
“Charlotte! Do you have to call me that?”. I was so embarrassed.
“That’s your name silly. Have you chosen my dress for Saturday yet?”
“Not yet. Getting there though.”
“Good girl” Charlotte replied. “Did you see the present?”
“What present?”
“The one I left on the bed”.
“The skirt? You bought yourself a present? It’s nice”.
“You like it????” Giggling from Charlotte, and then fainter, “He likes it!”. There was a soft sound of laughter in the background.
“Who’s there with you?”
“Oh no-one…just some of the girls in the office. Nevermind that. Back to the skirt. You like it?”
“I guess so. It’s nice”.
“So …you like the present?”
“Yes. You’ll look nice in it.”
“I would, I know. Exceeeeept…..it wasn’t for me…”
“What do you mean?” Could this mean…
“It’s for you silly!” More female laughter in the background…
“What do you mean, for me? And why are people laughing…are they listening to this????” I cried.
“Don’t worry about that. Let’s talk about your present later…I need to get back to work”
“Er…okay…Charlotte, I’m scared”.
“Oh, don’t be honey. It’ll be okay”. She sounded sincere.
“Okay. S…s…see you later. Bye.”
“Bye Caitlin…enjoy your present [giggle]”. Click.
And that’s how the conversation went. What do I do now!? She’s home in one hour. I’ll update you later.
Saragirl Sissy Confessions →
Charlotte sent me this link…is this where things are heading???
Photoset with 1 note
So Charlotte has a New Year’s party at her firm next week, and she’s asked me to help choose her dress. She’s never asked me for this kind of thing before. No partners allowed (it’s actually on Saturday night, not NYE), so I think she’s trying to involve me.
Some of the options are above. Charlotte asked for a brief commentary on each dress…
Which do you think? Usually Charlotte is more conservative, but I think some of them are a little…well…risque…
Imagine…
Coming to terms with who Charlotte seems to want me to become is exciting and absolutely terrifying in even measure. I would love to try on this outfit for fun, but what do these feelings mean? Where might they lead? Who will find out?
The thought of someone discovering my panties underneath my trousers at work…but what if Charlotte takes it further?
I’m sure this is how Charlotte wants me to look. Yesterday she told me she wants me to grow my hair long. When I asked her what she means, she showed me this photo.
“Long but easy to maintain”, she said.
“What about about the rest of the photo? Surely you don’t want…?”
“Oh, silly! One thing at a time!” she giggled.
I’m very worried by this development.
Oh my! Look how happy this girl looks in her pretty dress…floating skirts cascading over her legs, tight bodice, slender arms… so pretty.
I bet this fitted sundress feels dreamy to wear! I love her whole look - hair is stunning. I would love to be this girl, and have girly chats with Charlotte. I wonder if her boyfriend is taking the photo? I wonder what she’s thinking…
“Hmmm…skirt or dress? Skirt or Dress?”
Charlotte says one day this will be my morning choice, every morning…I’m scared…
Whoops…has my heel broken? No?
To go to work dressed like this would be heaven. Smart black skirt, fitted blouse, heels, new haircut…I bet she feels wonderful!
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