My Trans Journey

Staring into the lens of the camera, I psyche myself up and press the record button.

“Hello, and thanks for clicking on this video,” I say to the camera, with a big smile and a flick of my shoulder-length hair. “I thought I’d talk a little about how I’ve got to this point in my transformation and how I knew this was the right step for me.

As I look down at the small script I’d prepared, I felt confident about what I wanted to say.

“Since starting my journey, I’d had such an outcry of support and well-wishers,” I explain. “Of course, I’d received the negative comments you’d expect too.”

Tucking my fringe behind my ear, I give a smile at the camera.

“I’m recording this video in hopes that it might be helpful for someone else in my position. Deciding to start your transition is never easy. You know it’s a long road to walk.”

Rubbing at softening feminine skin, I let out a long sigh as the memories that are flooding back.

“Let's start at the very first time I knew I was ‘different’,” I say, gesturing inverted comma’s

Giving it a second or two, I look down at my notes and reminisce about my childhood.

“So I have an older sister,” I state, as I look back into the camera. “For most of you who are crossdressers, I’m sure this sounds all too familiar. That unexplained interest, in the frilly outfits our sisters got to wear. My first instance of crossdressing was with my sister. Being from a family that didn’t have the money to buy Halloween outfits, she decided I’d dress like her little sister that year.”

Looking away from the camera, I take a moment to remember the feeling. The excitement of wearing one of my older sister's summer dresses out in public.

“Being quite young at the time,” I continue, as I look back into the lens with a wide grin. “I don’t think anyone really thought anything of it. They just thought we were having fun! Little did they know how thrilled I was to be treated like a pretty little girl.”

Rubbing my forehead, I try my best to remember what the dress looked like.

“I think I wore a yellow flowery dress,” I tell the camera, with no real confidence. “I deffo remember wearing the dolly pumps and tights. The tights were amazing. I couldn’t believe just how different they felt and made me feel.”

Brushing loose strands of hair away from my face, I give the camera a silly smirk.

“If any of you are wondering,” I giggle. “That night was the first time I was referred to as Penny. Now you guys know where that comes from!”

Allowing my face to become more serious, the tone in my voice soon dropped.

“Well, I guess for my early childhood, that was the peak,” I say in a dour tone. “After that experience, I wanted to do it more and more. When I kept asking my sister, if I could dress up again, she became more and more freaked out with every time I asked. That’s when my crossdressing became secret and a deep one at that”

Looking down at my notes to compose myself, I take a moment to breathe. I hated feeling so isolated back then. Feeling like something was wrong with me, it still kinda hurts to this day.

“So it became,” I say looking back at the camera. “My deep secret. Something I was afraid to talk about with my family. Something I had to do in complete privacy.”

“Like most closet trans folk,” I continue, but now fiddling with my hair tie. “I’d wait until the family was out of the house and I was alone. At first, it started with just wearing my sister's underwear. As I started experimenting with outfits, the more fun It became. I started researching outfits for girls my age. It became like an obsession.”

Pinging my hair tie against my wrist, I then look back up at the camera and give a wry smile.

“I remember this one time,” I say with an awkward smile. “When I was a teenager, and out with my friends. We’d always go to the mall and try to talk to girls. That was when I started feeling so out of place. They always talked about how each girl had a lovely this or a lovely that. I saw those girls completely differently. All I could think was how was how lucky they were and how I was jealous I couldn’t dress as they did.”

Still looking into the lens, my smile becomes wide, as I think about myself back then.

“When I look back on it now,” I giggle. “The things I used to say to fit in with the other boys!”

With a shake of my head, strands of my hair cover my eyes. Brushing the strands aside, I give the camera a playful look.

“I won’t share those silly childhood comments with you here,” I chuckle. “Maybe in another video, we can talk about the things boys do to be macho in front of their friends!”

Tucking any remaining loose hair behind my ear, I refocus and look at the camera, with a serious expression. “So I guess I should also tell you all about when I got caught.”

Letting out a long sigh, I look at my ceiling and prepare to tell the story.

“I can’t quite remember how I came to be in the house alone,” I admit, as I slowly bring my face back down. “I’d been working on an outfit for months. I’d managed to buy a pair of heels, from eBay, and I was a little too eager to try them out.”

With a quick turn of my head, I look over at my closet. “I think I’ve still got them somewhere……”

Turning my head back to the camera, I give it an awkward smile.

“So I’d been through the usual process,” I continue. “I’d shaved what little hair I had. I brushed my wig straight. I applied my makeup as best I could and I laid out several outfits from a selection of my sister's clothing.”

Thinking about what I was saying, in front of a recording camera, my face began to blush.

“So there I was,” I say, with a smile. “Standing in my sister's bra, knickers, and tights. With a long blonde wig, cascading down my back. Complete with a face full of makeup, trying to decide on what outfit I wanted to wear!”

Letting out a small giggle, I look off to the side.

“I was soo engrossed with deciding if I wanted to wear jeans or a dress!” I bashfully laugh. “I didn’t hear her come home!”

Throwing my hands out, I mouth the words bang.

“I’m sure you guy can imagine the panic!” I exclaim as start shaking my hands like a jazz musician. “The look on my sister's face…..I will never forget it!”

Bring my hands down, I look away. Nervously, I look down again at my notes.

“I think in some ways,” I say in earnest. “When Suz’s found me that night, I think it was a godsend.”

Now playing with my necklace, I stare out of my bedroom window. Seconds pass, as I replay the memories in my mind.

“Now as you can imagine,” I say, refocusing my attention on the camera. “Suzzy did not let me off easy. For months and months, she’d threaten to tell mom and dad about what she’d caught me doing. On many occasions, she blackmailed me into doing her chores.”

“I also lost access to her room.” I swiftly continue. “Thinking about it, maybe that was a good thing. It made me realize how much I missed dressing as a girl and acting like one. I think those months of not being able to be myself, really planted the seed in my mind.”

With a pause, I look down at my phone and open the pictures app. Showing the pictures to the camera, I scroll down and giggle.

“Now,” I say joyfully. “Like most women, I liked to take pictures of myself when I thought I was dressed pretty.”

Turning the phone, I look at some of the images I had saved.

“I’ve got thousands of pictures of me,” I giggle. “At different stages of my transformation. Different outfits when I was crossdressing. Millions of different poses!”

“I’ve even got some naughty ones!” I admit, winking at the camera.

Placing the phone back on the table, I brush the hair from my eyes once more.

“It’s those naughty pictures,” I say, glancing down at my phone. “That was the catalyst for my decision to transition.

Tapping my finger on the desk, I give the camera a sideways glance.

“Now I bet you’re wondering,” I say with a straight face. “How do naughty pictures lead to such a life-changing decision!?”

I lean in, closer to the camera.

“Let me tell you!” I exclaim. “I’d been talking to a boy for months on a crossdressing dating site. Those pictures had garnered his interest in me. Let's say his name is Frank.”

Moving back from the camera, I slouch.

“Frank was,” I say, as I nervously itch the back of my hand. “He was my….first.”

Looking down at the table, I try my best to keep myself talking. The unbelievable urge, to switch the camera off, was intense!

“I’d got…..,” I say, but cut myself short. “I think it’s important to mention. At this point, I’m eighteen.”

Looking up and forcing a smile, I do my best to continue telling the story.

“We’d decided to meet at a hotel,” I explain. “Not being able to dress at home, thanks to my sister's embargo on her stuff, I planned to get dressed at the hotel. Frank had kindly offered to buy me clothing.”

“Now, you might be thinking,” I say as I glance away. “Something really bad happened to me that night. I can tell you, that wasn’t the case. Frank was a complete gentleman. Although I was terrified about my first time, it was a delightful experience for us both.”

Turning over my hand, I begin to pick at my nail varnish.

“Over… the…. year,” I explain, with drawn-out syllables. “We continued to see each other every weekend. We even took several long weekends away and I was dressed the entire time. I remember thinking it was a dream come true! We used to pretend to be a married couple. It was kinda cute.”

Pulling a satisfying large piece of my chipped nail varnish off, I look back into the camera lens.

“I thought things were great!” I cheer, then immediately frown. “Turns out, Frank had a wife. Said wife then proceeded to catch us on one of our weekends away.”

Pulling a sour face, I look out the window.

“I want to spare everyone the details,” I groan. “Basically, it ended with me being thrown out of the hotel, still en-fem, with no way of getting home.”

With an angry huff, I look back at the camera.

“The first man I loved!” I growl. “Drove away and left me at the side of the road, like a piece of trash!”

Anxiously looking away, I wipe a single tear from my cheek.

“Left with no option,” I sniff. “I called Suzzy and asked her to come to pick me up.”

Wiping away another tear, I put my smile back on and turn to face the camera.

“Obviously, having caught me dressed before, it wasn’t a shocked to her,” I explain. “It only really got awkward when she pointed out cum stains on my dress.”

Letting out a small, but nervous chuckle, I clear my eyes of any tears.

“I’m sure you can imagine the questions Suzzy's hand,” I say, with a smirk. “What should have been an extremely embarrassing car journey, turned into one of the most important moments of my life. As Suzzy lectured me about being safe, I realized there had been a change in her attitude and demeanor towards me.

Not being able to look away from the lens, I wanted to make my point.

“The way Suzzy treated me,” I continue. “It had changed! No longer was she treating me like an annoying little brother, but like a younger sister who needed protecting!”

Opening out my body, to look down at my transition, I give a wide smile.

“It felt right!” I cry out. “To be treated like a woman, it just felt normal. It just felt like me!”

Putting a thumbs up to the camera, I give a wide-eyed grin.

“Thank you, Suz!” I yell. “If it wasn’t for you’re encouragement and support, I would have never had taken this step. I want you to know, I’m the happiest I’ve ever been with myself and I owe that all to you!”

As those words echo around the room, I sit staring at the camera. The only sound to be heard was the whirring of my laptops fan.

“Penny!” Suzzy shouts from downstairs.

“Yeah….!?” I scream back as I turn to face the door.

“You’re boyfriend is here!” Suzzy yells back.”

“ Super!” I cheer, as I turn to face the camera with a beaming grin on my face. “Ok guys! Speak soon. Luv ya!”

Slamming my laptop closed, I end my recording.