Stepping into the Shadows: Nearly Caught Moments as a Crossdresser

Unlike most crossdressing stories that developed gradually, my desire for crossdressing was spontaneous.

 

Although I was drawn more to girls and enjoyed playing with them throughout my childhood, the thought of dressing up had never crossed my mind.

 

Plus, having been born into a religious family, the idea that it is taboo for a man to wear or behave like a woman had taken root in me.

 

 

 

Here’s my story and what I’ve learned throughout my crossdressing years.

 

 

Discovering My Identity

 

 

 

My first crossdressing moment came during my last year in high school. It came as a fictional character in a play in high school.

 

In the play, I was a house help who, according to the script, had queer behaviors.

 

One of these “queer” behaviors was role-playing my employers when they were not around.

 

In one scene, I had to mimic the mistress, and wearing her outfit was a part of it.

 

In the play, crossdressing and playing my mistress was quite strange.

 

But it wasn’t for me. In reality, I enjoyed it. I didn’t see anything odd with that.

 

Throughout the scene, you could tell I was enjoying role-playing as much as the audience was enjoying the play.

 

 

 

All through practice, some of my drama club mates would complement my appeal in my “boss’s” dress, saying that the dress made me look girly and cute.

 

In a way, they unknowingly encouraged me to crossdress.

 

I have always thought that that moment triggered my long-forgotten feminine energy.

 

The Guests

 

There is this one time we had to entertain some guests (my parents included) with that same play.

 

Later that evening, the scene was the talk of the day.

 

I still remember my dad’s “you really were a model on the stage today…” complement later that day.

 

And mom’s “maybe God changed his mind right before you were born” comment.

 

The talk must have awakened my alter ego.

 

And my desire and curiosity for what it feels like to be a woman was born.

 

 

 

In the later days, although I knew what I desired was supposed to remain a fantasy, my imaginary model (my dad’s creation) was not ready to leave.

 

Every once in a while, I would sneak into my sister’s dresser when she was away and…you know what…

 

These were moments of mixed feelings: curiosity first, then came excitement, elation, and all the euphoric feelings you can imagine.

 

And finally, shame, self-hate, and reprehension.

 

This cycle continued until I went to college, and I had to make a decision.

 

I decided to stop that “nonsense” and focus on my education.

 

Embracing My True Self

 

 

 

As you already know, stress and anxiety are a part of most college life.

 

One day, feeling depressed, I skipped classes and visited my girlfriend, Kate (she was also a student).

 

That afternoon, she left for class, and I had the whole of her room for myself, and curiosity took the better part of me.

 

I knew she would be away for hours, so I had more than enough time to try my old trick.

 

That is, I shaved my facial hair, bathed, and slid into one of her panties, bra, and a black floral knee-length dress.

 

I put makeup on and splayed myself with some perfumes…

 

It was the time I tried it all.

 

I was, however, unlucky as for shoes.

 

But it didn’t matter; everything else was perfect.

 

Every piece I put on came with some kind of thrill.

 

And finally,

 

Goodness, Gracious! It worked!

 

 

What I expected came to life. Excitement filled my soul, and the anxiety dissolved.

 

This time was different, though.

 

The negative feelings were never felt, which left me high on euphoria and a light mood.

 

Soon, a feedback loop was created.

 

And now, whenever I felt low, I’d always find a way to get into Kate’s room alone.

 

If you could ask me why, I couldn’t give a satisfactory response.

 

The truth is, I don’t know why.

 

All I do know is that it is just a feeling I have.

 

A strong desire that I cannot easily suppress and it somehow feels wrong to dismiss it. So I choose to give in.

 

The interesting part is it feels pleasurably right to do it.

 

When I do it, it brings an unmatchable excitement, an ecstatic feeling.

 

It calms me and helps me beat stress and anxiety.

 

Building My Wardrobe

 

 

 

After a while, I decided to build my wardrobe to eliminate the risks of getting caught.

 

By then, deciding what to buy wasn’t much of a problem.

 

The problem was where to buy and how to approach the process to ensure I bought the ideal stuff.

 

Online stores were not an option as I had had a bad experience with online shopping.

 

After a few thoughts, I decided to use my GF’s bestie, Samantha.

 

I used the narrative of surprising for my girlfriend to get her to go shopping with me.

 

Fast forward back home. I had a strange experience when I put on my garments.

 

Although I was satisfied with my choices, I felt happy and calm but discontented in a way.

 

Something was missing.

 

 

 

I yearned for the excitement I always got from wearing my girlfriend’s outfits.

 

It took me a while to realize I needed a full femme outfit, including underclothing.

 

So I had to go shopping again. I had to go alone this time since calling Samantha again would raise suspicion.

 

Shopping for feminine clothing on my own was an adventure in itself.

 

Shopping for femme outfits, especially undergarments, was a real challenge.

 

Trying on outfits in the store’s dressing room was quite a strange adventure.

 

Generally, navigating these situations required quick thinking and nerves of steel to deal with those scary, staring eyes – some judging and others commending.

 

Acquiring my outfit was a relief and an indication that I had found and embraced my unique proclivity.

 

The most interesting thing is that I lived alone in a small apartment a few miles from the campus, meaning I was free and would do what I pleased.

 

Nearly Caught Moments

 

 

 

Throughout my crossdressing period, I’ve had over a dozen close calls – at my parents and in my apartment.

 

I still remember most of them. There are two most embracing near misses that I recall quite vividly.

 

The first was at my parent’s house.

 

That day, I was alone at home.

 

My sisters had gone shopping, and Dad and Mom were at work.

 

My curiosity kicked in, and I went to my sister’s room.

 

I chose my outfit and headed back to my room.

 

I stripped off, dressed up, and went downstairs.

 

Dancing was my other favorite activity when I wore femme outfits besides cat walking.

 

That day the mood was on dancing, so I put on loud music and started doing my thing.

 

A moment of confusion hit when I saw the front door open after a few minutes into my dance.

 

My sisters were home. I didn’t hear them arrive, and I didn’t expect them so soon.

 

 

 

My younger sister was the first to enter.

 

I froze briefly after seeing her but regained consciousness soon enough.

 

Then, I dashed into my room, locked the door, changed, and sat on my bed to cool off.

 

I was sure she had seen me.

 

Returning downstairs, I was surprised to learn she had not seen me.

 

The TV must have somehow distracted her, so she instantly looked at the television’s direction upon entering the house.

 

Phew! That was close, but hey, lucky me.

 

The other moment was when I was in college.

 

Back then, crossdressing was my secret passion that I couldn’t tell anybody about, not even my closest friend Samantha (my girlfriend).

 

I can, however, assure you it was stupid not telling her.

 

One evening, she paid me a surprise visit.

 

It was one of the days I dressed up, put on dance music, and practiced my dance moves.

 

That day, I decided to wear underclothing only – my favorite panty and bra, and black stockings on top.

 

As usual, she didn’t knock.

 

Considering I didn’t want her to know about my crossdressing, I had to hide and stripe off as soon as I heard the front door open.

 

Well, the easiest option I had was the bathroom, so…

 

I succeeded, or so I thought. I preferred she sees me naked than in female wear.

 

Navigating Public Places

 

 

 

Typically, going out in public as a woman requires energy and dedication.

 

And for a long time, I lacked the courage.

 

The fear of confrontation and exposure had taken the better part of me.

 

But I needed it. Indoors CD was not quite fun anymore.

 

I started by strolling in the neighborhood in the evenings.

 

All I had to do was avoid risky places or bumping into someone who’d recognize me.

 

 

 

First day in a public place

 

I put on my favorite white satin panty (padded butt enhancer panty) and bra.

 

I then stuffed the bra with some pads to enlarge my boobies.

 

Afterward, I slid into my floral knee-length pink dress and matching heels (I’ve had a thing for pink and white for quite a long time, BTW).

 

I then applied some lipstick and headed out.

 

I felt so alive walking down the streets to the neighborhood public park.

 

The breeze through my naked legs and stares from my admirers complemented the sensation.

 

After a few walks to the park, I decided to make it a bit more interesting.

 

I decided to try going to a local nightclub but considered doing it on the weekend when clubs were full, as the chances of someone recognizing me in the crowd were slim.

 

 

 

The following Friday evening, I asked Kate to go clubbing with me.

 

I had opened up to her earlier on. She agreed after some resistance.

 

That evening was the moment of transformation.

 

Kate came home and helped me with dressing up and doing my makeup.

 

It was like she had waited for that moment for so long.

 

She put all her makeover expertise on me, which resulted in the creation of an entirely new me.

 

My male persona was surely intrigued by the beauty I saw in the woman looking back at me from the mirror.

 

You would have to pay close attention to recognize me (my male persona).

 

 

 

On the way to the club, hundreds of thoughts crossed my mind.

 

What if someone recognized me?

 

What will I do when someone notices and confronts me?

 

How will I answer if someone asks me why I wore female clothing?

 

I couldn’t stop the train of thoughts that consumed my mind.

 

I almost backed out, but I eventually got there with Kate’s support and encouragement.

 

The club was packed, as I anticipated.

 

However, several clubbers (some familiar) noticed and approached us.

 

And although I was hard to recognize, a few of my college mates recognized me.

 

Some of them confronted me, while others just assumed.

 

I tried to explain myself to those who confronted me.

 

Still, I knew it didn’t make sense to some.

 

The majority of my friends understood me.

 

What surprised me most was the support I received from some of them later.

 

More surprise!

 

Two of them even wanted to hang out with me more when dressed up.

 

Lessons Learnt

 

 

 

Throughout my crossdressing, I have learned two vital lessons.

 

First, embracing oneself is the most crucial thing to do as a crossdresser.

 

It makes life pretty easy, and most importantly, it enables you to enjoy every moment of your crossdressing sessions.

 

The other thing I’ve learned is that there is strength in vulnerability.

 

Crossdressing is often regarded as a sign of weakness.

 

And growing up in a society that discourages it, you can be sure you will feel the same.

 

However, fighting your desires does not make things right. Instead, it suppresses our mental health.

 

Embracing that vulnerability, on the other hand, enables us to live authentically.

 

And that fosters our emotional and mental well-being.

 

Additionally, it helps us find and build a strong connection with people who accept us for who we are.

 

Conclusion

 

 

For a long time, I dressed up discreetly. However, every once in a while, I would wear my tight panties and tights under my male outfits when going out.

 

The tightness under my male outfit kept my feminine energy alive, which I almost always found quite comforting.

 

Still, I have to admit that opening up comes with a whole different experience.

 

Yes, you will lose a few friends. But who cares.

 

Eventually, you will gain more – supportive – friends. I am still attracting more.

 

That’s what matters.

 

That’s a wrap.

 

However, I’d like to hear your story.

 

Tell me; How did you overcome the fear of getting caught?