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Bucket List – Boxes Yet To Tick – Part 2

Our trip through Dee's bucket list ends, but not without more surprises!

I’ve written the last two weeks about my bucket lists, the first week about the things I’ve done, and last week the first half of things still on my list–the boxes yet to tick.

As I did last week, 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), both on a scale of ten. These are MY scores; your mileage may vary.

Here’s the continuation of my list in no particular order, but just in the order I jotted them down (the first seven were last week).

8. Fly pretty

If you are a CD (likely, or you wouldn’t be reading this), you know exactly what this means.
The term (in our circles) is generally attributed to Kimberly Huddle from her blog Traveling Transgender. She wrote about traveling around the country in a variety of outfits, generally while schlepping various testing equipment in heels and a skirt, regaling her readers about interactions with airline desks, TSA agents, car rental clerks, and hotel front desks. 

For many of us, it made the idea of flying while dressed a viable possibility. Others in our community have followed the trails that Kimberly blazed, and written about their travels, and how the TSA is trained to handle the issue professionally. 

Reading these stories makes it another case of “I can do that”.

Moreover, I WANT to do that.

Desirability: 9; Probability: 9

9. Visit Renee

I’ve written often about my GG friend Renee, a long time ago FWB, and about how we reconnected via Facebook. She helped introduce me to dressing all those years ago (I dropped some pretty broad hints) and she bought me my first pair of heels. We text on a regular basis, talk on the phone occasionally, and she is my sounding board for a multitude of outfits and thoughts (yes, she loves seeing pictures of me dressed).

She lives in a college town (think of a couple of big NCAA hoops rivals) about 800 miles away. Yes, there is plane service there (see item 8 above). She has mentioned the possibility of a visit if we can figure out the right time, but we would both enjoy face-to-face time instead of just communicating by thumbs and photos. And we might find time to do something else fun (see number 10).

I need to find a good race to do in her area as a cover story and hit the friendly skies (likely another airline so I can carry two suitcases of girl stuff instead of one).

Desirability: 10; Probability: 7 (coordination of schedules might be tough).

10. Formal night with Renee

A couple of years ago I was trying on a strapless blue turquoise dress and trying to decide whether to buy it. Renee texted “buy it and then figure out a place to wear it”–and I did. Good advice.

Lately I’ve tried on more formal dresses at stores, because they are fun to try on and dream about where to wear them–and I send Renee the pictures.

Renee dresses more for comfort, and doesn’t do dresses, skirts, or heels. She wore them (reluctantly) 35 years ago when we met, because of work requirements. One time when I dressed up for her I wore a floral suit of hers, and she said I looked better in it than she did. But she does favor the Marlene Dietrich look. 

Recently, I sent her the following text:
<<Logistics aside, it would be a lot of fun to attend a formal event with you in the tux and me in the gown. There might be a slight height discrepancy, with me in 3 inch heels and you in tennis shoes (gotta wear tennis shoes with the tux, right?). And part of the process will be shopping for my gown. A girl’s gotta dream, right?>>

I’d say we’d both be all in on this one.

Desirability: 10+; Probability: 4 (hard to find the right event at the right time).

11. More GNOs (Girls Night Out)

I’ve been out a few nights with my GG girl friends, some dinners, a ball game, a few times at a local bar, Hooters (Michelle loves Hooters).

But I want more. My GG friend Falon wants to go out at night (we haven’t yet). Michelle and I had a memorable night out and we’d like to do it again.

This is one I want to tick off time and again, but it’s just difficult to make the arrangements and make them work (especially when you’re wife doesn’t know anything about these friends).

Desirability: 10; Probability: 10 (eventually, but it could be a long time coming).

12. Drag makeover 

I’ve never been to a drag show. Michelle wants to take me to one, as she has been before, and if she wants to go, I will certainly tag along.

This list item started about 6 months ago at a local bar called Hemingway’s. I was with Michelle, and she introduced me to her friend Patty. As it turns out, Patty’s gay son was engaged to a drag performer, and Patty showed me pictures of the fiancée. I loved the look.

I immediately realized it would be fun to get a drag makeover, to see how I would look. Of course, I would then need to figure out someplace to go with my drag makeover…

Desirability: 8; Probability: 5.

13. Hit the beach

Last summer, with the wonderful assistance of Michelle, her pool, and her variety of suits, I did a bathing suit/bikini photo shoot. It involved Nair, a lot of shaving, and spray tan to blur my tan lines, but it was a dream come true.

My wife (an Aussie) and I own an apartment in a suburb of Melbourne, and the apartment is about a block and a half walk to a nice beach on the Bay of Philip. There are also other beaches a bike or train ride away. I generally (non-pandemic years) spend mid-January to mid-March (their summer) at our apartment. The opportunity is there.

Going out in the summer wearing a wig (and makeup) and hitting the beach is (admittedly) not the brightest of ideas. I do have a one piece swimsuit (my wife didn’t want it anymore, and I did), but it has to be a bikini, right? 

I also now have three covers to wear over my swimsuit/bikini, courtesy of (who else?) Michelle. 

Desirability: 8; Probability: 10 (gotta buy a bikini).

That’s my current list. Everything is subject to change, but these are things I’d like to do. I’m sure you have your list too, but I hope you enjoyed reading mine.

[As your editor, I completely enjoyed the ride Dee!]


5 Responses

  1. Dee, your extensive bucket list is wonderful. I will add my responses for most items, as one is very specific to you and your friend.

    8. Desirability: 9.9, Probability: 3. My opportunities are so limited to achieve this one, but it is still the most likely of those I haven’t done!
    10. For any formal night, desirability: 8, probability: 2. Again, the lack of opportunity is the issue here.
    11. Desirability: 9, Probability: 5. I’ve had multiple times out with a close CD friend and would happily do so as often as possible. It would be even more meaningful to go out with a GG friend (if I had one).
    12. Drag show desirability: 7, Probability: 1. Drag makeover desirability: 3, probability: .1. The over-the-top drag look does nothing for me, but seeing a show would be a lot of fun.
    13. Desirability: 6, Probability: .1. I don’t have a swimsuit and probably will never get one, although I’ve thought about it over the past couple of years. But I would have to lose a bit of weight before I felt comfortable even in a one-piece.

    My CD bucket list has grown from seeing other’s lists like yours!

    1. Thanks Tina! I hope others got a few ideas too.

      These type of lists are often what keeps us going.

      I like to say I need lots of carrots at the end of my stick. The boy me signs up for running races or triathlons, which then means I have to go out and train to do them (run, bike, swim), otherwise race day is zero fun.

      The side benefits of doing the work is a healthier and slimmer me, one that can play multiple hours of tennis or walk 18 holes of golf. It also means good looking legs in heels and slinkier girl clothes to wear.

      Make your list, find your carrots, make it happen. If I can, you can.

  2. Dee, I’m new here and have totally enjoyed your bucket list. Here’s how your list works for me:
    1. Desirability 10 Probability 0 …. no opportunities
    2. 10 / 3 …. love to just couldn’t explain it to my redneck family
    3. 10/2 … date yes, but nothing beyond after dinner drinks
    4. 10 / 6 … if the opportunity ever arises … but I’d need a lot of shopping to start
    5. 4 / 1 …. not that into the idea
    6. 8 / 5 … maybe not Eastern but have thought of welly services often
    7. 10 / 4 … working on a crossdressing spy tale but procrastination will likely win out
    8. 10 / 7 … done it a couple times just don’t fly much anymore
    9. 3 / 0 …. seems like a personal one for you
    10. 9 / 2 … would love to attend a formal event just not too many in my circles any more
    11. 9/ 4 … need to find some new girls sinice we moved last year
    12. 5 / 1 .. been there done that
    13. 9 / 7 …. but probably in a one-piece…. at 65+ it’s hard to sell a bikini
    I’d also love to do a cross-country train trip, and attend a major sporting event en femme both of which are 10/5s. Thanks again for the thoughts

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