Crossdresser – The first step out

This is a work of fiction.

Please do not break the law or attempt any of the stunts in this story.

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After cross dressing in secret for a long time. It’s finally time to step out of the shadows.

There are no sex scenes in this piece, but because certain body parts were mentioned, it’s still classified under erotica.

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It all started with some clothing donation.

You know, those bags of old clothes that you leave outside your door for the different organisation to pick up for recycling or donation.

I remembered I just came back from school and I walked past my neighbour’s place.

Mr and Mrs Tan.

They were a young couple who just moved in next door and they just had a baby.

With the new addition in the family, Mrs Tan, then, a sweet looking 29 year old, had to get rid of some of her old clothes. 2 bags full of them outside her flat for the recycling company to pick up.

Perhaps it was because of the thunderstorm, the man never came.

The clothes remained outside her door.

I reminded them that the clothes were getting drenched in the rain as the wind swept the heavy shower onto the common corridor.

Mr Tan was trying to make a bottle of milk while Mrs Tan was busy trying to pacify the crying child.

Mrs Tan : James… can you be a dear and help us bring it down to the bin…. Just throw it away… or leave it there for whoever wants it…. We’re a little overwhelmed …

James : ok sure…

I didn’t think much of it.

I carried the 2 bag of clothes into the lift and while it descended down to the ground floor, I looked at it.

I looked at the clothes in the bag.

And I saw the glimpse of a bra strap.

In a colour different from the usually white straps I saw on my classmates in school.

My heart started beating faster.

That must be Mrs Tan’s old bra.

I don’t know what came into me and I immediately hit the level 3 button, bringing the lift to a stop just before it reached the ground floor.

I brought the 2 bags of clothes out to a corner of the landing and I put them down.

I was nervous.

I’m not stealing, these are clothes Mrs Tan don’t want.

She wants to give them to anyone who wants them.

I’m not doing anything wrong.

I kept repeating that to myself in my head. I undid the knots on the bags and when I opened it, I felt I opened the first treasure chest in my life.

T-shirts. Pants. Work tops, pants, bras, even panties and towels.

Everything that Mrs Tan used to wear.

I could feel the erection in my pants as I quickly opened the other bag. It too contained more of Mrs Tan’s clothes including some old lingerie.

I looked around the quiet and dark landing.

I can’t bring it back up just like this, Mr and Mrs Tan would see me entering the flat with the clothes in hand. My mind immediately worked out another route I could take.

My block is a horizonal block with 3 staircases. 1 in the middle 2 at the side.

I just need to take the lift back up, stop one floor before my level, and walk along the corridor to the other staircase which I can use to access my flat.

Brilliant.

I did just that, bringing for the first time women’s clothes into my room.

My parents work long hours and I’m the only child.

I have all the privacy I need when they are not around.

I took a shower and change out of my school uniforms.

I went over to the 2 bags of clothes I salvaged and I started to go through them piece by piece.

I could remember some pieces which Mrs Tan wear before.

I spent 30 minutes picking out the items I want to keep before I discarded the rest into the refuse chute.

I removed all the clothes from my body.

I don’t know what was going on in my head but I was excited. I was feeling this excitement I could not describe. It’s really weird.

I picked up Mrs Tan’s pink and lacy panty and I put my leg through the hole. As I dragged that panty up along my hairy legs, I could feel my cock getting harder and harder.

The panty felt tight against my erection but it was not uncomfortable.

I picked up a bra that is black in colour. This one had no lace but it had a small fake diamond in the centre where the 2 cups meet.

I slid my hand into the strap and with a few tries, managed to buckle the bra onto my body.

I looked in the mirror and adjusted the lingerie on my body.

Then I picked out a grey sleeveless dress that I have seen my neighbour wear frequently before she got pregnant. I slipped it on, covering the bra and panty underneath.

The satisfaction that I derived from dressing in Mrs Tan’s clothes gave me my first mental orgasm.

I sat down and opened my books and homework.

It’s my ‘o’ level year.

While I would usually get distracted easily, I found that I could concentrate more when I am wearing women’s clothes.

I was on fire.

I could memorise better, I was accurate in my math, and I could write better composition.

You must be laughing at how silly this is but it’s true.

It’s psychological I know, it’s all in the mind but what’s important for me was that it worked.

It worked for me.

That was the first time I crossdressed, but it was not the last.

It marked the start of my crossdressing journey.

I have salvaged enough of Mrs’s Tan’s clothes to wear something different every day without having to repeat for 2 weeks.

I used to head to the arcade, to hang out with friends, to play basket ball abut after that day, I started to yearn to go home more.

Because the moment I went into my room, I can be who I want to be.

No I’m not gay.

I don’t like men.

I still like women, I still fancy the girls in my class. I still get excited seeing the occasional upskirt when going up the stairs or oogling at the fancy bra straps my classmates wear to school.

I just liked the feeling of wearing women’s clothes.

Unknown to anyone around me, not even my closest friend, I wore panties into my O level papers.

Mrs Tan’s panties.

And I went a step further.

I bought sanitary pads, put them onto the panty and I wore them.

I wore them and sat through all the papers.

Did I get 7 distinctions ?

Well, a total of 7 A2 for a student that has been getting Bs and Cs his whole life. That’s a major improvement.

My teachers and parents were over the moon.

They thought I finally grew up. From promises of a new game console to holiday trips, they offered me everything.

I went into Junior College and seeing my classmates in their short skirts and ankle socks. It drove me to buy a set of female uniforms. When I head back home after school, that would be what I wear for my revision.

I would be wearing the skirt, the blouse and ankle socks as I do my homework.

No one knew, not even my parents. I kept all the female clothes separately in a different compartment in my wardrobe. I wash them on my own, and I hang them out to dry in the afternoon sun, making sure to collect them back in before my parents came back from work.

I got into a relationship with a really sweet girl in the 2^nd year of my JC.

Alicia.

We kept the relationship a secret from everyone in school.

Alicia has her long line of suitors, but I was the lucky one. We just clique instantly.

We kissed in school. We held hands in the cinema and we first made love after our last ‘A’ Level paper in my room.

It was the first time for both of us.

Neither one of us came but we just enjoyed the feeling of each other’s body.

I like the feeling of my dick inside Alicia’s privates. I craved for that feeling everyday after.

It took us close to 6 months after that before we learnt how to have sex properly and we were doing it like bunnies whenever we had the chance to.

I went to the army shortly after that while Alicia waited for her university term to start.

On weekends when I book out, I would meet my girlfriend. We would date like every other couple, we go to the movies, we eat, she stays over, we have sex.

On days she can’t stay over, and when I have time alone, I would crossdress again.

No longer do I have to content with Mrs Tan’s old clothes.

I have a wider selection now.

Alicia’s clothes.

Yes. Alicia leaves quite a bit of her clothes at my place. From sleep wear to lingerie. I would crossdress in them.

Why ?

Why wear your girlfriend’s clothes and lingerie when you can have sex with her as and when you like ?

I can’t explain.

It’s different.

I just feel alive when I do it.

I have no intention of changing sex.

I love women. I surf regular porn.

I masturbate to beautiful friends.

And I love to crossdress.

To feel the sensual material of lingerie on my skin.

I like the feeling of being feminine, but not to the point of being a sissy.

Alicia and I stayed as a couple from JC all the way till we enter the workforce.

And at 26, I proposed to her.

She said yes of course.

We bought a resale flat together.

With our own place, I have greater control over my cross dressing hobby.

I don’t know why but after I proposed, my crossdressing fetish got worse.

A lot worse.

I have never ventured out of my room before when I dressed up but I was suddenly hit with this urge.

This feeling that I need to leave the room, to appear in public.

To show everyone that when I crossdress, complete with a wig and all, I looked just like a girl.

I started to plan for it. I started to look forward to that day when I would finally step out of my house in full female clothings.

That day finally came when Alicia went overseas for work for a few days.

I had already shaved all my body hair and told Alicia that I did it because I swim and cycle frequently. Something to do with aerodynamics.

I put on light makeup, I pulled on an expensive wig I bought online.

Slipping on Alicia’s lingerie, I put on a dress she usually wears for work.

Alicia’s heels were too tight for me but I managed to squeeze into a pair of her Melissa.

And I ventured out for the first time in the wee hours of the morning.

Dressed like a girl.

The thrill cannot be described.

The thrill of getting caught, getting spotted.

No one saw me of course. It was 2 am in the morning.

It felt like a drug and I craved for that excitement.

I brought clothes and heels to my office too. I would go back to work during weekends in the empty floor.

No one ever comes in on weekends and I have my own room even as a junior staff.

It’s totally safe.

How do I know that ?

My parents own the company.

I would go back early in the morning on weekends, dress up, slip on panty hose and heels, put on wig and makeup, and then I would do my work.

When I got tired, I would stage my own photoshoot in the office with a tripod.

I posted my pictures online and the praises I received spurred me on further. Even the females think I looked more like a woman than a man.

My confidence grew.

I don’t just want to sneak around in women’s clothes.

I want to live and experience what it is like to live like a woman.

With my girlish features and boyish looks, I am confident I can pass off as a female as long as I don’t speak.

In the midst of planning my crossing dressing escapade, I was hit with a sick thought.

A really sick and bold thought.

I have never broken any law throughout my years of crossdressing.

I never stole any clothes. I bought them all with my money.

And I could feel myself shaking in my skirt and heels as the idea of breaking so many laws altogether at the same time hit me.

The excitement.

I cannot describe it. That exhilarating feeling started in my stomach and started to shoot straight into my brain.

I know I can’t keep doing this.

I cannot cross dress forever. I need to stop eventually after I get married but before I do, I must do something big.

Something that I will never forget.

And I made a list.

A crossdressing bucket list.

And it starts with me going into the female toilet, dressed as a female of course.

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5900+ words

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