Experimenting With Different Cross-Dressing Styles in One Day

In most of our cross-dressing sessions, we tend to wear a single outfit for the duration of it.

That’s because dressing up takes a lot of time, and changing outfits can ruin our makeup.

Many of our sisters have limited time for their cross-dressing sessions.

It is unpractical for them to try different styles.

The result is slow progress in their journeys and the growth of curiosity.

Because of that, I’ve decided to try out different styles in a single session.

I wanted to see if it was possible. In a day, I had spare time and nothing else to do.

It wasn’t easy, but I did enjoy the results.

If you want to know more about this experience, keep reading, as I’ll explain everything here.

1. A context for the day

Since I came back to college after the lockdown (due to COVID), I’ve been cross-dressing more than ever.

However, I had to do so in short sessions as my classes and assignments took a lot of my time.

Well, the end of the semester is close. Some of my classes have been over since last week.

Besides that, my two roommates were away, so I had the whole apartment.

I couldn’t think of a better thing to do than use this time and privacy to cross-dress!

Besides that, I’ll spend my college vacation in my hometown.

Thus, I’ll have fewer opportunities to cross-dress than at my apartment.

Thinking of that, I wasted no time and invited my girlfriend over and told her to bring some makeup that she had borrowed.

2. Deciding upon the different styles

Well, with all that time to dress up, it was hard to decide what I wanted to look like.

I brought three of my wigs with me and bought two more since then, so I had to choose my hairstyle.

I wasn’t going on a date like last time, but the weather was nice, so I could get creative with the outfits.

I spent quite a few minutes deciding when it occurred to me that I could try more than a single style.

With so many options and time? So I was determined to dress up in more than one outfit that day and take as many pictures as possible.

Everything was in my favor, and my girlfriend even said she would help me change clothes.

So why not give it a try? Maybe this experience will serve as a way to exemplify things to some of our sisters.

3. What did I want to try?

Well, as I’ve said before, there were some outfits I had acquired recently and wanted to try out.

I got a few things from Shein months ago and have gradually tried some combinations.

Still, I had a new wig as well and have been letting my natural hair grow to style it more femininely.

I also haven’t been wearing my breast forms due to having limited time, but I was eager to show some cleavage.

I knew I had to dress up as soon as possible to calm down and hold my excitement during my vacations.

Maybe that would be my last opportunity to dress up for a whole month!

I wasn’t going to waste it, so I set apart those items I wanted to try out that day to make sure I would wear them.

4. Getting ready

Once my girlfriend arrived, she told me to go get ready, and I didn’t want to waste a second.

I grabbed my shaving cream, razors, and moisturizers to take a  nice shower and shave as much as possible.

I spent a whole hour in the bathroom, but the results paid off.

My skin was smooth, and my legs already looked feminine, if I might say so.

The shower felt terrific; shaving is like freeing my skin from undesired body hair.

Mine grows back fast, and I hadn’t shaved in weeks.

But now, I was ready to be Elise again, so I had to put some effort into getting rid of all that hair.

Armpits, legs, forearms, and even my crotch, so I could feel more comfortable in my panties.

I also did wash my hair, which is something I don’t do too often when I shower before cross-dressing.

That’s because wearing a wig right after a shower is harmful to our scalp, as it doesn’t let our hair dry properly.

But I really wanted to see how I looked with my natural hair, so it was time for some shampoo and conditioner.

Besides that, I was planning on wearing a lot of shapewear and doing elaborate makeup.

This would take some time, and my hair would have plenty of time to dry before wearing a wig.

The next step was shapewear, and I wore all I had to get the best curves I could.

It included a pair of waist cinchers and a tummy control bodysuit.

The results were decent, and I concealed everything with my Roanyer breast forms.

This silicone vest goes down to my belly and has a neck piece that hides my adam’s apple.

As for underwear, I went with my usual combo of black panties and bra, as I like how they look on me.

And for the first outfit, I wore some of the stuff I bought from Shein.

Including some bodystockings, a black shirt, sheer black pantyhose, and black shorts.

Footwear was a pair of converse all-star shoes in their classic black and white.

It was more of a goth look, and my girlfriend did the makeup.

She’s good with eyeliner. My skills are still no match for hers!

To complete the look, I wore my newest wig with a fringe.

5. Spending sometime en femme

My first look was ready, so I spent a good part of my day dressed like that.

I cooked lunch for us, then spent some time with her watching some stuff.

I also played video games and got some work done.

A little photo shoot was also mandatory to keep a register of such a special moment.

It felt amazing, and I couldn’t resist looking at myself in the mirror every now and then.

At first, I wasn’t satisfied with my curves. It’s a dysphoria thing, I guess.

Maybe some hip pads will help in the future.

But after a while, I couldn’t see anything but a good-looking girl whenever I looked at my image.

It made me happy, even though my back was starting to hurt.

Maybe too much shapewear was an exaggeration after all.

Nonetheless, it’s always a pleasant experience to spend a whole day as a girl.

I didn’t tuck that day, so going to the bathroom was easy.

6. Changing clothes

The hours passed by, and I knew I would have to change clothes soon if I wanted to accomplish my goal.

It was time for it, I decided, since the shapewear was hurting a lot by that time.

The only issue was makeup, as I didn’t want to smudge it. I had to be extra careful.

I started by removing the wig and releasing my natural hair, now properly dried.

Then I stripped my clothes until only underwear and shapewear were left.

The difficult part would be to remove my silicone vest without damaging the makeup.

To my luck, my girlfriend was there to help.

She held it while I carefully pulled the silicone up, sneaking my head through the neck hole.

It was a success, and in a matter of seconds, I was only in underwear with my makeup intact.

After resting a few minutes, the second look I chose was my regular college outfit.

I wore the class t-shirt and regular pants, once again carefully so as not to damage the makeup.

It was also a success, and even without shapewear, I felt feminine enough.

I tried to style my hair in a more feminine way, and although it was convincing, I still needed a more feminine haircut.

7. How I felt afterward

Most of the experience was positive, as I felt really feminine during the entirety of it.

When the time came for me to go to sleep, I wished I didn’t have to go back to boy mode.

But I know that sleeping with makeup on is a bd, as it harms our skin.

I reluctantly removed it but felt fulfilled after managing to do so much in a single day.

The only thing I didn’t like was how the excessive shapewear felt.

It hurt a lot, and after comparing pictures of me with and without my waist cinchers, I felt that wearing two of them was unnecessary.

I’m glad I used my silicone vest, as the cleavage was very realistic, and I managed to cover my shapewear.

It allowed me to take some pictures that I wouldn’t be able to without it.

Cross-dressing demands time, skill, and patience. Even more, if you plan on wearing different outfits in a single session.

But I recommend you do so, as the experience is quite pleasant.

Beginners should try it on a day that they have plenty of free time, as I did, but our more experienced sisters can try it anytime.

Keep practicing! What different cross-dressing styles would you like to try out? Let us know in the comments!

Quiz:

What demands the most time from cross-dressers?

A. Shaving body hair


B. Choosing the right outfits


C. Doing elaborate makeup

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Written by Elise