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Epic Experiments in Crossdressing Volume One

by Jessica De Leon on February 15, 2010

Research, Development and Engineering Command Job OpeningsA few months ago my wife and I were talking about crossdressing and we approached the topic of underwear. Many, if not all, cross-dressers experience intense feelings — emotional and otherwise — when wearing women’s underwear. Everyone’s experience differs slightly but all in all wearing lingerie is thrilling, exciting, daring and amazing.

However, both genetic and trans women do not undergo the same adventure, because after all, it’s an everyday thing. Wearing a bra and pair of panties is just another step in getting ready for the day. We discussed this at length, comparing and contrasting the feelings I have versus what she experiences on a daily basis.

After our discussion I began kicking around some ideas in my head. I wondered what it would be like to wear a bra every single day until it became routine and even mundane. What emotions would I experience, how would my wife react and how much would our laundry bill increase? As I pondered these and other questions, I seriously considered this idea. Which brings me to. . .

The Experiment – Wearing a Bra Every Day For a Month

Starting today, February 15th, I will be wearing a bra every single day for exactly one month. Yes, that’s right. Whether I’m working, sleeping, eating, shopping, partying, gaming, exercising, worshiping, cleaning or doing anything else (and whether  I want to or not) I will be wearing the undergarment in question.

The Details

First and foremost, I proposed the idea to my wife and she is 100% supportive. With her blessing, I am venturing forward and will be documenting my progress and thoughts during the month-long experiment. Given my habit of cross-dressing only once a month or so, I only possess three or four bras. Because of this, I will need to purchase a couple more so that I am not doing laundry every few days.

I also must consider how things will show through clothing. Seeing that we are in Winter and temperatures are currently dictating outerwear, this may not be a problem during the first couple of weeks.

Why am I doing this for 30 days? Well, because many companies allow you to try products for thirty days, giving you ample time to really find out how you feel about it. Also, I fully expect that somewhere during this experiment, it will become habit.

What This Isn’t

I would like to emphasize one thing – this is absolutely not a joke or a mockery of any kind. For many of us in the transgender community, something as simple as wearing a bra can be life-altering. I am not condescending or parodying this in any way.

My Findings

Each day I will be recording my results – the what, why and how I feel during this undertaking. I will do this with a combination of note taking and audio dictation. I will update my status frequently, though I’m not quite sure what that rate will be as of yet.

Of course, the written word simply will not suffice for some people who will require additional proof to believe in what I am doing. Keeping this in mind,  I will be snapping discrete and tasteful pictures that I will share on this blog that will accompany my writings.

Questions I Will Consider

Here is a brief but ever expanding list of things I will consider during this month:

  • Will wearing a bra become boring, tedious and/or annoying?
  • Will wearing a bra irritate my skin?
  • Will I, at certain points, forget that I am wearing a bra?
  • Will doing the laundry take on new significance?
  • At what point, if any, will it shift from “crossdressing” to “habit”?
  • What feelings will my wife experience?
  • At the end of the trial, will I miss wearing a bra?

Also, following feminist research, I expect to be reflexive in these questions, therefore they will probably change and be expanded upon.

Any Suggestions? Join In?

If you are curious about anything, would like to suggest something or just want to cheer me on — feel free to express it in the comments section.

Also, if you’d like to join me in this experiment and share your findings and feelings, you’re more than welcome to!

Creative Commons License photo credit: RDECOM

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{ 33 comments… read them below or add one }

1 Petra Bellejambes February 15, 2010 at 9:09 am

Jessica – I really have to complement you. I think you plan is superb, and I greatly look forward to hearing your thoughts.

I do hope that that Mrs. De Leon takes notes throughout. Given that she is an observer of the experiment, I would encourage her to not prod you, or share notes or thoughts with your readers throughout the 30 days. This might have the effect of polluting the results. I would greatly enjoy reading her recap notes at the “trials” conclusion though.

Good luck! I do hope that the fastening of the clasp still feels as magic in mid March as it does for you today.

xoxo – Petra

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2 Jessica De Leon March 2, 2010 at 9:09 pm

Thanks Petra, I really appreciate your encouragement. Mrs. De Leon has been super busy, though, and hasn’t really been taking any notes. However, I will ask her about her thoughts when all is said and done :) .

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3 Misty February 15, 2010 at 11:11 am

I wear a bra most everyday now and always wear panties and hose I don’t own a pair of male briefs or boxers and haven’t in several years. But wearing a bra is just part of being dressed and yes sometimes I forget that I have one on.

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4 Jessica De Leon March 2, 2010 at 9:10 pm

Interesting, I wonder if I am going to feel the same way.

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5 Caroline February 15, 2010 at 11:54 am

Some thing which may cause a certain frisson of excitement by virtue of their transgressive nature can quickly become just normal and second nature, that’s where my vote goes.

I hope you’re going treat them carefully when doing the laundry, none of that just throwing them in the washer dryer and hoping for the best!

Looking forward to the results.

Caroline XXX

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6 Jessica De Leon March 2, 2010 at 9:10 pm

Yes, they are being handwashed (in a way) and being taken care of :) .

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7 Angie February 15, 2010 at 12:26 pm

I think that it is a great idea. You may like it so much that you keep wearing a bra beyond the 30 days.

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8 Jessica De Leon March 2, 2010 at 9:11 pm

Thanks! We shall see :D

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9 emma38c February 15, 2010 at 12:40 pm

Great Idea,
I have been wearing a bra and panties every day for about a year now.
As with anything else such as shaving or brushing your teeth somedays you don’t notice and other days it seems like a real bother.
It is defintly a learning experience at times you need to be aware of where you are and who might notice as in public or at work.
Most days I love the feeling of being hugged by my bra and at times have seen the knowing smile from a passing gg who notices a strap impression or some projection at certain angles.
If on certain days I don’t wear one such as a exam at my doctors, the answer is yes I really miss wearing one.
Addictive ? Definetly could be.
Why I underdress, after prostrate cancer radiation treatments need to wear protection from leaks was needed. and a Always pad and panties are much more comfortable than anything else I had found. Meds from the prostrate treatments seemed to enhance my breasts and a 38D fits well as prevents bounceing which becomes painfull after a while.
Best wishes with you grand experiment I look forword to seeing how it goes for you.

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10 Jessica De Leon March 2, 2010 at 9:16 pm

I am sorry to hear about your cancer, I hope that your recovery is going well. One year, wow, that is a long time, congrats! Sounds like you are enjoying every bit of it, and that’s admirable.

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11 Julie M Shaw February 15, 2010 at 7:02 pm

You are so adventurous, sweetie. Thank you for keeping this blog relevant, and also entertaining! Good Luck – and I might try it myself.

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12 Jessica De Leon March 2, 2010 at 9:18 pm

Aw, thanks for the compliments Julie. Let me know if you go ahead and try this.

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13 Anita February 15, 2010 at 9:15 pm

Good luck! All the best with your endeavor.
will enjoy reading the results of this experiment.

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14 Jessica De Leon March 2, 2010 at 9:18 pm

Thanks! So far, so good.

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15 Leslie Ann February 16, 2010 at 3:55 am

I have been wearing pantyhose nearly every day for two years. It generated a lot of excitement for several months. Gradually, though, it has become a normal thing for me. It doesn’t cause elation any longer, but I truly miss it when I can’t. In other words, the desire is undiminished, but I notice the absence more than the presence.

This is a great idea! Wish I could join the experiment, but I have insufficent brassierage.

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16 Jessica De Leon March 2, 2010 at 9:19 pm

Yea, my brassierage is lacking as well, but I’ve been doing a lot of laundry (something I wanted to avoid, heh).

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17 ranielle February 16, 2010 at 6:58 pm

Bravo..I have just started wearing mine everyday and it is just great. I don’t own any mens under shorts, I gues you could say I am steping it up a notch. I wish us both well in our experament.

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18 Jessica De Leon March 2, 2010 at 9:19 pm

Cool! All the best :)

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19 Leslee February 16, 2010 at 7:44 pm

Interesting idea. Ive been wearing panties since very young and I just accept the fact that that is normal for me. I only wear a bra when I go out dressed up but Ive done it so many times I never even notice it anymore. I guess Ive crossed this idea already and I know what my result was. Wonder if you come to my clusion also.

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20 Jessica De Leon March 2, 2010 at 9:20 pm

Yes, we’ll see if I come to similar conclusions. :)

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21 anna February 16, 2010 at 9:14 pm

I’ve been sleeping in panties & nightgown almost every night for several months now. It has definitely become less exciting, but it never became any less enjoyable.

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22 Jessica De Leon March 2, 2010 at 9:21 pm

Sounds like another great experiment ;)

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23 SheenV February 17, 2010 at 9:59 am

This is something that I’ve wanted to do – you’re lucky you have a very supportive wife. I look forward to reading your observations.

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24 Jessica De Leon March 2, 2010 at 9:21 pm

Thanks, I appreciate that. I am very fortunate that my wife is on board with all of this :) .

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25 Gaven February 17, 2010 at 6:43 pm

I look forward to hearing about the results. I have been thinking about buying a bra or two my self as I do not own any right now. I do not think I could wear one everyday with out changing the shirts I wear in my work life.

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26 Jessica De Leon March 2, 2010 at 9:23 pm

Gaven, you could try different types of bras such as racerback or wireless bandeau. Even sports bras would be a good way to be discreet. :)

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27 Veronica February 18, 2010 at 11:35 pm

I wear a bra almost everyday so I have gotten pretty used to it. The only day I don’t wear one is when I see my kids on Sunday. At first you might notice wearing a bra, but then you’ll get used to it. My wife laughs at me at the end of the day cause I’m happy to take off my bra just like her. :) I’m glad that your wife is supportive of your experiment. Good luck, Jessica. Can’t wait to see your updates throughout the month. =)

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28 Jessica De Leon March 2, 2010 at 9:24 pm

Thanks, Veronica. Though I have to say that I am mirroring my wife in her habits, and she sleeps with her bra on, so I am doing the same :) .

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29 Gigi February 21, 2010 at 5:51 pm

New to all of this. Still in the closet. Only person that actually knows is my gay daughter.

Thank you for this site. I will monitor it regularly and hope that my courage increases as I see yours has.

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30 Jessica De Leon March 2, 2010 at 9:24 pm

Welcome, Gigi. It’s nice to see you here. Thanks for commenting and reading. Keep in touch :D

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31 jarrod aka jenifer m. February 22, 2010 at 7:05 pm

oh yeah a bra really completes the feminine feel.ive gotten to the point that i wear a hanes sports bra most every day of the week.ive also noticed that when i dont have one on i can really feel my boobs bounce when i walk or move around.every thing just feels so snug and secure underneth a bra.im into a 38 b and i can fill it out perfectly,i like to wear tee shirts a lot so i wear sports bras cuz you cant see any bumps under my shirt,but if my wife and go out for the night i will always wear an under wire job that fits like a glove i do show two very distint bumps though,and have gotten some stares from people,but they problably think i have gyno mastica or something. i really dont care. i hope you will love your experience i do.

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32 Jessica De Leon March 2, 2010 at 9:25 pm

That’s awesome Jenifer :) !!

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33 Jean Ann June 27, 2010 at 1:39 pm

I think your experiment is great. A real life test of just what it would be like. Not only the physical part but also the emotions etc.
You should try it next with b or c forms
I think a good follow up experimet would be to wear short shorts in public ,perhaps someplace away from home. See just how it feels to have people look etc

Jean Ann

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