Bucket List – Boxes Yet To Tick – Part 1

Now let's see what Dee is planning in the near future!

I wrote last week about my original bucket list–manicure, makeover, trying on dresses, and buying a wig dressed–and how I thrust Spaceship Dee into warp speed and accomplished a whole list of things I would have never thought possible. That list included the boxes I have ticked. 

This week–and next–the boxes yet to tick–the list of things I’d like (probably more accurately, dream about) to do.

In our house, we rate movies on a scale of ten (well, we did when we actually went to movies in pre-pandemic times), with ten being a high score and one the dud score.
For my list, I’m going to give two scores, a desirability score (how much I’d like to do it) and a probability score (how likely it is to happen). These are MY scores; your mileage may vary.

Face it; if you are reading this, you have your own list (seeing lots of nodding heads all throughout the interwebs).

Here’s my list, in no particular order, but just in the order I jotted them down.

1. Attend a wedding

I can almost guarantee that every CD who attends a wedding sees at least one dress they would have loved to wear to the wedding, as opposed to the drab clothes they are actually wearing. It’s not only attending the wedding, it includes going shopping for THE dress to wear to the wedding, preferably with a girlfriend to help you chose.

But most of all, if you would be invited to a wedding as your femme self, it means the bride and groom WANT you at the wedding as your femme self.

Plus, dancing in a dress and heels would be tremendous. 

Desirability: 8; Probability: 1 (very small population of friends to have this be possible)

2. Get my ears pierced

Pierced ears opens up a wide variety of cute earrings to wear, and ones that don’t pinch or fall off like clip-ons.

The downside is explaining for two months why you are wearing studs while the piercings heal.

Desirability: 5 (not that big of deal for me); Probability: 1 (see downside above)

3. Date night with a man

This is more a fantasy than a bucket list item. The idea of being asked out, getting dressed up, getting picked up, yada, yada, yada, is very appealing. Who doesn’t want to be wanted? A night out, dressed nicely, to a suitable location? Count me in.

The reality is I’m not into guys and I’m not attracted to them. I’m aware there are admirers (including possibly some readers here) who WOULD be interested, but I would have little interest in any post-date “activities”. I don’t know any admirers. I’m also aware I could hire an escort, but I’m not sure how that would change the mental dynamic for me.

Plus it would be a hard sell to my better half, or I would need to cover my tracks really well.

Desirability: 7; Probability: .001 (can’t ever see this happening)

4. Dressing full-time seven days in a row

As I wrote last week, I have spent at least part of a day dressed for seven days in a row. This would be full time for a week.

Day one would be a salon day (get ready, Michelle): manicure, pedicure, waxing, more waxing (brows, and tinting brows, nose, ears, etc, but no bikini waxes). I love getting my fingernails done, and I’m sad when I have to remove the polish. Plus having painted fingernails–or getting acrylic or gel nails, a step up–means you are “pot committed” to dressing full time until the polish or nails comes off.

The reality is that it’s a lot harder being a pretend woman. Dressing as a woman takes at least an hour, versus about five minutes as a guy. You need a daily close shave. Makeup every day, maybe more than once a day. You have to figure out girl things to do for a week. You need a suitcase large enough for a week plus of outfits (plus the additional stuff you are going to buy).

The other reality is that all these “problems” are definitely worth it.

Desirability: 9; Probability: 7 (I have the free time and funds to make this happen)

5. Have a boudoir photoshoot

What’s more feminine than lingerie? What’s one of the first items that young CDs try on? What fun things to wear under your guy clothes to remind yourself what you’d like to be wearing?

The reality is a lot of CDs prefer clothes that hide our guy flaws (including the equipment that makes us guys). With lingerie, there is a lot less there to hide those flaws. What we see as sexy on a GG is not quite as sexy on one of us. There is also a ton of body hair to deal with, and suddenly showing up a lot less hairy may cause some uncomfortable conversations. 

Nonetheless, I’m all in on this one (and there are services that can make this happen).

Desirability: 10; Probability: 9.75 (Michelle would probably enjoy this almost as much as I would, and she would lend me her frillys)

6. Going to church on Easter Sunday

This one popped into my head a while ago. Now I have the dress to wear!
Michelle is a regular church goer (Catholic) and she dresses very nicely to attend Easter Services. The last several years, she attended in a lovely Calvin Klein rose colored dress, one that she looked great in. As of last month, that rose colored dress is now mine, as Michelle gave it to me. 

I am, to put it mildly, not a church goer. The last times I was in a church were either weddings or on my last European trip in 2019.

But the idea of putting on a beautiful dress and attending a Catholic service with Michelle (and her family) is irresistible, even though she would know EVERYONE, and she would proudly introduce me to EVERYONE, because that’s who she is and what she does. 

Desirability: 9 (don’t ask me why, it just is); Probability: 7 (some logistics to work out, but Michelle is hard to say no to)

7. Publish a crossdressing story on a story website

I have always preferred the written to the visual. Back in the day, I preferred the letters in Penthouse over the centerfolds in Penthouse, especially the letters that dealt with crossdressing.

If you haven’t figured it out by now, I also enjoy writing. I guess I should have added to my boxes ticked post about writing–and posting pictures–regularly on a blog. However writing these blog posts was never on my bucket list–it just happened.

With tons of time spent running or biking, I have lots of time to mentally compose stories, most of them centered around crossdressing. I’ve had the basis for a story kicking around my head for at least five years, and I’ve even committed most of it to paper (which in 2021 is a Word document). But I find reasons not to finish it, or more accurately, lack motivation to finish it, and then take the steps to post it on the interwebs. 

It’s not going to be the great American novel, and it’s a pretty basic crossdressing story–and most stories in the crossdressing categories tend to be more “exotic”, to put it mildly–but I’d like too see whether people like it or not.

Of course, the irony would be the same as these blog posts. I write these weekly, yet I can only tell a literal handful of people that I know–the handful that know Dee. I can’t tell the friends who know the guy me, “looky here what I wrote”. That’s not going to change any time soon. For the record, my wife doesn’t know I post here, much less publish my pictures–and she only knows about a handful of my outings, and none of the details.
It would be the same for any stories I publish; I could tell only a small minority of those who know me.

But hopefully there would be someone out there who read my story and liked it, and that would be good enough for me.

Desirability: 9; Probability: 9.99 (I believe I will eventually get it done,, procrastination notwithstanding).

Hope you enjoy my list. More next Sunday.


3 Responses

  1. Dee, this is a well-thought-out list, the detail about each one is evidence of your desire. Here’s my take, using your scale, on these items:

    1. Desirability: 8, Probability: .1 I don’t know enough people as Tina for this to be realistic.
    2. Desirability: 7, Probability: 4 It’s been discussed but never acted upon.
    3. Desirability: 0, Probability: 0 Not even as a fantasy.
    4. Desirability: 9, Probability: .1 I’ve done 4 straight days although I didn’t go out each day, but there are no opportunities for this in my life right now.
    5. Desirability: 4, Probability: .1 I have enough worries about how I look without stripping down to lingerie. I love lingerie but it’s just for me.
    6. Desirability: 7, Probability: .1 I’d consider any church visit dressed, not just Easter. Again, no chance that it will happen any time soon.
    7. I’ve actually done this, although it does fall into the more “exotic” category.

    Hugs, Tina

  2. I’m not sure I’ve got a bucket list but I did go on a 7 day cruise and was in girl mode the entire time
    It was amazing and yes the prep was the tough part but I was welcomed on the ship even with male ID and such things
    Now Admittedly for certain parts I was a bit more androgynous but I was mostly a girl.
    I had two photo shoots from the ship folks and I’ve still got those pictures
    I know that going full time would be a chore but for 7 days I loved it

  3. Thanks ladies!
    I hope my list (and the following items next week) stimulated some list making among others.

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