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Halloween 2024 at Work!

21 Posts
10 Users
38 Reactions
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Posts: 29
Lady
Topic starter
(@bobbiann929)
Trusted Member     Ontario, Canada
Joined: 1 year ago

Hi girls!

I haven't posted in a while, but I'm still here and have been reading a lot of your posts and living vicariously through them.

I promised Ellie Davis a while ago that I would write about my transformation trip to Toronto, and I will.  I'm just so busy and I'm not a very social person (I usually make one or two facebook posts a year).

But while it's fresh, I want to tell you all about my experience at work this Halloween!

I work on the front desk at a retirement home.  This was the second year I've gone to work en femme on Halloween.  Last year I dressed in business attire including a black pencil skirt.  This year I was more daring, choosing a bright pink dress with a turtleneck and long sleeves.  On some women it may be a long dress, but on my six-foot frame it ends a fair way above the knees.  I matched it with a pair of bright pink shoes with three-inch wedge heels and ankle straps.  As they have open toes, I painted my nails (pink - can you tell I like pink?) and went bare-legged.

I have previously documented how my wife runs hot and cold about my dressing.  Lately it's been more cold.  She had said a while ago that she was fine with me dressing on Halloween, but I wanted to make sure she was okay with it.  So a week prior, I mentioned to her that a lot of the residents were asking if I was going to dress up again, which is true.  Even some whose memory is not good remember that!  I asked my wife if she was okay with me dressing again, and she said, "it's your life".  That has a kind of ominous subtext to it, now I think about it in retrospect, but at the time I was relieved she said yes.  A couple of days later, despite her not wanting my crossdressing to become public knowledge, she was telling her young adult nephew that I was going to be dressing as a woman again for Halloween and even sent him a picture of me from last year!

I had a day off work two days before Halloween and told my wife it was going to be a makeup practice day.  I hadn't been wearing makeup much lately so I wanted to make sure I wasn't taking too long to get ready on the day of the event.  She made a joke and went to work.  I spent the day reacquainting myself with the full routine, and even managed to attach false eyelashes for the first time.  I thought I looked pretty good, but I wanted to get my wife's opinion (and I didn't want to take it off - you know how that is!).  Well, when she got home from work, she didn't want to look at me dressed and made up.  I quickly went back to drab but she barely spoke to me the rest of the day.

The next day when we both got home from work, she said she never wants to see me dressed and it sharply decreases her attraction to me as she can't get the image out of her head.  I had planned to use that evening to paint my nails and shave my legs, hands and wrists so I wouldn't have so much to do the next morning, but I decided not to risk upsetting my wife.

Halloween day came and my wife went to work.  The party at work was mid-afternoon, and my shift at the front desk followed that until early evening.  I started getting ready after my wife left.  My nails took a fairly long time, what with having to wait for them to dry and putting on two coats.  And the false eyelashes weren't cooperating.  The outside edge on my left eye was sticking out so, bravely overcoming my fear since I was in a hurry, I added more glue with the eyelashes still on my face.

My makeup was ready a half hour before the party was due to start, but I still had to get dressed.  I messaged my bestie co-worker that I would be half an hour late.  I put on my recently-purchased waist cincher (very good investment!) and my silicone shorts with false vagina (another good investment although the sheath took a bit of getting used to) and some bum padding, inserted some hip padding into the shorts, black panties with more bum padding, silicone breasts in a pocket bra with a sports bra over that, and with my very thin body and the dress clinging to every curve, I had a figure to die for!  I chose a black wavy-haired shoulder-length wig, and added a black purse, pearl necklace and large silver hoop clip-on earrings, and off to work I went!

This account is longer than I thought it would be, so I will post the conclusion tomorrow.  I promise!  

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20 Replies
7 Replies
Ambassador
(@alexina)
Joined: 10 months ago

Famed Member     Fife, United Kingdom
Posts: 1742

@bobbiann929 

We'll be eagerly awaiting it, Bobbi. Thanks for this 😊.

Well done for bravely carrying on despite your wife's current disinterest!

Allie x

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Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@alexina Thank you, Allie!

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Duchess
(@loneleycd)
Joined: 5 years ago

Famed Member     Roland, Iowa, United States of America
Posts: 2033

@bobbiann929 Bobbi, like everyone else I am eager to read the rest of the story. I assume you loved the day, but I am wondering about everyone's reaction at work. Both your coworkers and the residents. 

Cassie 

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Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@loneleycd Oh yes, Cassie, it was good!  I will share the conclusion soon.

Reply
 Lea
Lady
(@lea-jhene)
Joined: 9 years ago

Noble Member     California, United States of America
Posts: 986

@bobbiann929 Wow, what an interesting post, ups and downs, this life is not smooth. That's great you still had the courage to dress even after your wife's remarks.

It hurts to hear negativity from our SOs. Every once in a while, a remark comes out from my wife and it feels like a setback. Then some alone time comes up, I get dressed, I feel good again. My goal to just be me seems to have its ups and downs.

Can we truly make our wives happy. I don't think so. Can we make ourselves happy. Only if we change what we value.

Can't wait to read how the rest of your dressed up time went.

 

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Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@lea-jhene I do so wish my wife was more supportive, Lea.  She has her moments, but seems to be going in the wrong direction.  I don't blame her, but I wish it could be different.

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(@denimwear)
Joined: 3 years ago

    Other, Alberta, Canada
Posts: 689

@bobbiann929 

Hi Bobbi,

That shows a lot of determination on your part to go ahead with your Halloween plans despite your wife's opposition. It shows a great deal of desire to follow your own yearnings as well. 

In my experience, when one's wife says, 'Fine', 'That's fine,' or 'It's your life' it is best to proceed with the utmost caution.

What I mean is that, speaking from experience, when they say that it doesn't necessarily mean they approve.

I'm sure you must have received some admiring looks on the day snd I am looking forward to reading all about it. 

Lynne   

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Posts: 667
 Erin
Princess
(@erinb)
Noble Member     Ohio, United States of America
Joined: 3 months ago

The suspense you sound stunning they way your described your outfit sorry about the SO I completely understand that situation cant wait to read the rest to come TC 

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2 Replies
Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@erinb Thank you, Erin!  I will post the conclusion soon.

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 Erin
Princess
(@erinb)
Joined: 3 months ago

Noble Member     Ohio, United States of America
Posts: 667

@bobbiann929 understand indeed

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Posts: 554
Duchess
(@jennconn)
Noble Member     Florida, United States of America
Joined: 2 years ago

Hi Bobbi.  I can’t wait to hear part 2 also.  I’ve always thought it would be so much fun to have dressed for Halloween when I was working, but I always knew I’d go too far with it and accidentally ( or on purpose) out myself.  Now that I’m single, I know there would be so many questions about who did your makeup and I can’t believe how realistic some of you looks.  So that’s why I’ll be interested in your next installment.

Oh, one other thing I’ve noticed, as far as wives go listening to my friends on chat, it seems that most women are ok with crossdressing except when it’s their man doing it.

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1 Reply
Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@jennconn Oh yes, Jennifer, people did ask who did my makeup.  Last year, I said my wife helped.  This year, I said I did it myself.  One person followed that up by asking how I knew what to do, and I just said I did research!

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Posts: 998
(@rebeccabaxter)
    Cornwall, United Kingdom
Joined: 11 months ago

and she said, "it's your life".  That has a kind of ominous subtext to it, now I think about it in retrospect

Not a good phrase coming from anybody, really; it's hardly encouraging at the best of times.

Still, at least you did your Halloween thing; I await the next instalment to see how much you enjoyed it (I'm presuming you did).

Becca

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1 Reply
Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@rebeccabaxter The subtext of the remark sailed over my head at the time, Becca.  She said it in a kind of "que sera sera" way.

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Posts: 3083
Hostess
(@ab123)
Famed Member     Surrey, United Kingdom
Joined: 4 years ago

The outfit sounds fantastic! I also await the resulting update.

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1 Reply
Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@ab123 I do love the dress and those shoes, Angela!  I never took a selfie, as I was running late.  Maybe I will post a rehearsal pic if I have a shareworthy one.

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Posts: 29
Lady
Topic starter
(@bobbiann929)
Trusted Member     Ontario, Canada
Joined: 1 year ago

Here I am replying to my own post.  Well, I also laugh at my own jokes.

Part 2 might not be today.  I had written about half of what I planned to in bed this morning and planned to finish when my wife went out.  But she's under the weather today.

And what I had written has disappeared, so I'm going to have to start from scratch and I have to go to work soon.  I might have a chance tonight, or it might be Tuesday.

Forgive my ignorance, but is there a way to save a draft here?

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Posts: 492
Duchess
(@gracepal)
Noble Member     South Carolina, United States of America
Joined: 3 months ago

I’m always struck by the sentence “Supportive SO with reservations.” Or as Bobbie says here “Hot and cold”. I recently updated my own profile to give my wife more credit. She has no reservations that I can’t reasonably talk her out of with some reassuring common sense.

Here’s what I don’t get with SOs: They’re only clothes. It’s not full time. It’s a hobby. It’s not a big deal so it shouldn’t be this huge “thing” in your lives. (Note to all my girlfriends on CDH here: Don’t share all your fantasies with her. They’re probably not gonna happen anyway so keep those in the vault.)

Last night my wife actually wanted to see my latest Grace photos. She asked ME. I had my 10 best all ready to go. And of course one of them I’m wearing a babydoll dress, short. She comments: You really are a little vixen aren’t you Grace?” I said, yeah, I guess I really am! Had no idea I was just two months ago🥰. We laughed and talked about it and had a great time. Since the dress was a size L I told her, you’d look way better in it than me…give it a try on! Now, I LOVED her in the thing and she HATED it…totally not her style. If fact, do any GG’s wear babydoll dresses or just us girls?

Bottom line here is it’s a total upside with an agreeable spouse. If she isn’t, turn her into one. It’s all in the approach. Try the humorous ones first, what’s funnier than you in a dress? (Probably me in a dress acting like a little vixen.) I think you can get your lady on board if keep reminding her of how great our hobby is: She knows where you are when you do it.  It’s not expensive. She already knows a lot about it. You’re not keeping secrets from her by sharing some stuff. (Would she rather you hide things? For most women that’s a big NO.) It’ll bring laughter into her day🤣. 

How do you eat the pink elephant in the room ladies? One bite at a time.

GP

 

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2 Replies
Lady
(@bobbiann929)
Joined: 1 year ago

Trusted Member     Ontario, Canada
Posts: 29

@gracepal Thank you very much for your comment, Grace.  I would love to involve my wife more; unfortunately she has made it clear that seeing me as a woman is a giant turnoff for her.

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Duchess
(@gracepal)
Joined: 3 months ago

Noble Member     South Carolina, United States of America
Posts: 492

@bobbiann929 That’s interesting Bobbi. My wife made it very clear that Grace “doesn’t do anything for her in the turn-on department.” I said great! Can I just get you to take a few snaps of her? Which she does. Now she’s starting to think it’s more fun having her around.

Have to keep telling them it’s nothing to do with sex if they can’t see that themselves.

GP

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