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Chapter 1: Cynthia’s First Outfit

"The very beginning of my Crossdressing adventure."

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It was playing on my mind all month. After returning to the single life, I spent the days wondering about the swift satisfaction I had wrapped in cute skirts and satin panties when I was living at home. Thankfully, I worked part-time in a cafe as a server in one of the local coffee shops, which allowed me to get some money for other expenses. 

It was around the month of June, and I was in my apartment finishing up an assignment. The Winter in Melbourne tends to be fickle, with rainy or cloudy outbursts followed by days of pleasant coldness. I put aside my notes and sighed, catching my ragged reflection in the mirror. A loose t-shirt and jeans that were way too tight held me in place, as irritatingly awkward stubbles blotted my face. 

I turned back to my laptop and begin to search up some porn. Before I know it, I’m watching a slew of trans girls, ladyboys, and crossdressers getting a good cock in them. It was such a turn on. I stroked my short four-inch cock vigorously to these videos, imagining more and more so that I am the one in their place: dolled up, exposed, and ravaged. Seeing their thong-covered asses getting fucked by amazing cocks made me extremely horny. 

After cleaning up, a realisation and urge overcame me. I recalled the websites that I used to use to buy clothes for my ex and briefly did fantasise about buying them for myself. It called to me more now, and I could not resist the urge to log on once more! 

My little clitty throbbed as I logged back on to the LoveHoney website and skim through their outfit choices. Although my ex had her tastes, I was always drawn towards a particular schoolgirl set. It was a short pink tartan mini skirt and a tie-up white top with matching knee-high socks. My heart leapt the second I saw this again. 

Without thinking too much I added the item to the cart, a medium-sized measurement. I felt so naughty thinking about it, but I now knew the set wasn't complete. I needed undies! I scoured the site, looking at scantily clad women modelling such delicate and attractive lingerie but the price points were just too high! As I browsed the listings, I became more and more infatuated with the idea of wearing the lingerie, and not actually seeing women in them. 

At last, I found my set: A simple, and cute white panties and lace bra set! It’s also one of the cheaper options, thankfully! Without skipping a beat, I hit the buy button and that was that! The wheels were now in motion, and for some reason, I felt a lot happier. 

The clock was set, and the parcel arrives in three days now. I was thinking about it over the weekend, while I bought a simple liquid foundation, mascara, eyeliner, blush set, and lipstick from a few stores. All that was left is to find a wig and shave myself clean. 

The wig was relatively easy to find. A quick trip to Creative Wigs landed me with a lovely dark brown wavy wig with bangs, much like my very own hair texture. It did cost a fair bit, but I simply knew it was a long term investment. I then spend the night shaving myself completely. It’s so liberating to see my smooth skin in the mirror. My ass and around the special bits were really tricky but so worth it once I walked out of the shower. 

I took a look at my smooth body, and despite never really having a masculine figure being shiny and smooth really brought out my mother’s fem figure. My shaved boobs were soft and lightly jiggly, my ass was fat and plump, and surprisingly, my hips were nice and thick. I only ever disliked my broad-ish shoulders. 

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It was finally Friday! I returned from a half day at Uni and brought the parcel up to my room. My heart was beating at the thought of what lies inside. As I opened it, looking at my very own lingerie and schoolgirl set, a rush of fire swept through my body. The outfit was extremely sexy. I physically could not imagine wearing it. 

Without skipping a beat, I headed into the bathroom and stripped naked. Using a razor, I got rid of any stray hairs on my face and body before applying some lotion, watching my skin glow. Then, after watching a quick video tutorial I began to apply my makeup rather amateurishly. 

(In retrospect it wasn’t too bad, but it was very cakey and plastic! I’m way better now)

Firstly, it’s the foundation, followed up by a setting spray. Then, I spent way too long with the eyeliner and mascara, followed by dark red eyeshadow and blush. Lipstick went on next. Lastly, I put my wig on, and simply marvelled at who the cutie in the mirror was! 

“Oh fuck!” I exclaimed. “I look good!” A smile appeared so wide on my face; true happiness! I finally looked so fem!

I rushed out to my bed and looked at my outfit neatly laid out. Slowly, I got my panties out and slid them up my legs. The smoothness of the cotton was so exciting, and watching my clit snugly placed inside them was a whole new experience. A gave myself a quick turn in front of the mirror, seeing my bubbly butt nearly absorb the panties! I then snatched up the bra and hastily fastened it on. Every crossdresser knows the trick of fastening them, then rotating them to put them on, which is what I did. 

Fully clad in my lingerie, I felt empowered! Like a sexy suit of armour encapsulating my now feminine body. In a heartbeat, I tied the top around my chest, feeling my small boobs shape out so delicately on them. Lastly, I took up the skirt and rode it up my legs. Feeling the fabric grip my waist and hang barely around my ass is such a rush. Without spoiling the surprise, I put on my stockings too and felt the soft silk clasp on above my knees. I was in heaven!

The reveal as I turned to face the mirror was very thrilling. My boy shape is no longer in view, and Cynthia stood in front of me. My hips were round and thick, my belly showed like lovely curves, and my face looked fem! 

“My God, I am such a girl!” I exclaimed and made a twirl to watch my panties flash in the mirror. “This, this is amazing.” 

I marvelled at Cynthia, and got giddy from excitement. It all just fits so well, that I fell back onto my bed and just lay there as a girl. The feeling of panties, the exposed top, the short skirt that is more accessory than garment, and the soft stockings were just thrilling. I started to let my hands run wild, as they explored the spaces under my skirt, and grabbed onto my lace-covered boobs. Just playing with myself in the manner set me on a roll!

As I lay there in bliss, I took up my phone and turned on the selfie camera. I hit record and did a quick scan of my face, down my chest to my belly, passing around my ass and back up. When I watched the video, seeing this girl in the recording, aroused me so much. The view was breathtaking, and so much was about to happen. 

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Written by CynthiaSissy
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