First Time Dressing

I was at home, upstairs in the bathroom where the light is best at mid-morning. My hands shook slightly as I put on makeup, desperate not to smudge it or get one eye different to the other.

As I worked, I remembered online tutorials and the advice of girlfriends. There was so much to consider! From foundation skin tone to the amount to apply; from the right shade of blusher — which I’d learned should match my natural inner lip colour — to the way bronzer evens out the planes of my face. I was reassured by the realisation that applying makeup was like decorating, rather than a mystical talent women are born with.

More by luck than anything else, I did a decent job, and the smells and sensations that seemed so strange at first, from the woody scent of eyeliner pencil to the wet chemical feel of foundation on tender just-shaved skin, began to take on a more familiar aspect, is if they were friends.

Back then my hair was short, so I wore a wig — a little black bob of the kind I’d always dreamed of but never dared to have cut. I had on a tight blue one-piece dress and was delighted with the padding I’d added to feminize my figure. I feared the curves would look ridiculous, but they suited me so well I had an odd dizzy moment, as if I’d glimpsed true reality from a haze of confusion and denial.

I decided to take a photo, and as my hands fumbled with the phone there was a knock on the front door.

I froze, while my insides lurched as if they were trying to escape. Hopefully, whoever it was would go away. This was my secret self! No one could know!

There was another knock, and I remembered I had a parcel due — forgotten in the excitement of finally becoming who I wanted to be.

I could stay where I was and let the delivery get taken back to the depot for collection later, but the depot was in the next town. The delivery was a computer part for a work project, which I’d already put off so I could explore my feminine self.

My breath deepened and I felt a curious clutching around my heart — like panic, but without the thought-paralysing fear. Instead of scrubbing off the makeup I had so painstakingly and expensively applied, or grabbing a thick blokey dressing gown to cover my feminine body, I drifted out of the bathroom onto the landing.

I felt very at home in my pretty dress, and my lovely hair, and my girl’s face. There was no embarrassment, or shame, or fear. I stood at the top of the stairs in sunshine that glowed through the landing window, its warmth steadying me.

Through the frosted panel of the front door, I could see a tall male figure. He appeared to be scribbling on something — perhaps one of those cards that tells you what’s happened to your parcel.

I was almost out of breath, yet unusually calm. The dress moved against my skin as my chest rose and fell, the unfamiliar but totally natural sight of my breasts an unexpected source of balance. The blue cloth felt incredibly sensuous, as if it were stroking me.

My legs, seemingly of their own volition, began to carry me downstairs. My boots clattered on the wooden steps, loud enough to ensure the postman heard.

I was going to answer the door as myself, and it seemed like the most exciting and yet normal thing I could imagine. My chin came up and I moved differently, as if my body had been constrained for too long in the wrong position. I felt my hair tickle my jaw, and I savoured the gentle weight of the shining fringe across my forehead. I felt my eyes widen — no more pointlessly aggressive squinting for me, thank you!

At no time on this epic, transformational journey down the stairs did I stop and think, ‘What the hell am I doing?’. Instead, I reached the door and saw the postman look up. He must have noticed a woman on the other side of the frosted glass — tall for a lady at 5’8″, but slim, and with a full red mouth and a bold, sexy hairstyle.

I opened the door.

The postman was in his fifties with greying hair and silver wire glasses. He stared at me, and I gave him my most dazzling smile.

“Hi!” I said.

Confidence was like a bloom of hot energy in my chest, which seemed to expand and make me lighter.

“Do I need to sign for that?” I said, still smiling as my steady gaze met his wide eyes.

The voice that came out was still mine, but it sounded different — softer perhaps, with the defensive edges melted away, like the new arrangement of a well-known song.

“N-no, it’s fine.”

He handed me the parcel, and my fingers closed on the smooth brown wrapping paper.

“Thanks so much!” I said.

Closing the door, I couldn’t stop smiling. There had not been an almighty crack as the sky sundered itself for the end times, and no crowds of pitchfork-waving villagers had stormed over the hill to burn me at the stake.

I looked at the parcel. It seemed an ordinary object, for such a momentous event. But, really, all momentous events are made up of much smaller ones, in a cascade that changes everything. I walked into the living room, loving the feel of my feminine aspect. I almost felt held by it, as if it loved me so much it didn’t want to let me go.

The computer part took a while to fit — they always do. Despite following the instructions, I inevitably find some tricky bit unique to my computer that needs lateral thinking, or further research, or a tense call to Customer Services who will without exception say something like ‘Well, that’s never happened before’.

Throughout, I felt the thrill of doing something ordinary while presenting myself in completely different way. My hair swung forward as I leaned over the guts of the machine, and I was conscious of my exposed legs and the comfortable tightness of the dress. It was thrilling, yet wholly natural.

I was working from home — which was more unusual in those pre-pandemic days. I decided I’d make a cup of tea and then start work as myself! I was curious to see if I would perform better, or more efficiently, or get less riled up with bureaucracy now I was en femme, to the extent that I was excited about getting started on the project.

Stepping into the kitchen, I saw that the kettle already had water in it. I clicked the switch down.

There was another knock at the door.

Emboldened, I left the kitchen, strutted down the hallway as if it were a catwalk, and opened the front door.

The same postman stood there.

“Hi,” he said.

I blinked, then blinked again, conscious of my long, mascara-thickened eyelashes.

“Hello.”

I wondered if he had forgotten something, even as I realised instinctively that he hadn’t. I felt a surge of anxiety. What did he want?

But I knew from the way he looked at me what he wanted. I was thrilled, and scared, and delighted all at the same time. To cover it, I put my head slightly to one side and allowed my lips to indulge in a little pouting smile.

“You’re very beautiful,” the postman said.

“Why thank you,” I replied, with an ease that surprised me.

“I’ve just been driving around, thinking about you.”

“Well,” I said, and nodded, which was all I could think of to do.

“I wondered if there was any chance of a cup of tea.”

“I’ve just put the kettle on!” I cried, my confused feelings erupting in sudden good cheer that seemed crazy even to me. Fortunately, he smiled.

“Good.”

I hesitated, simultaneously wanting him to come in and yet also wanting him to go away. Innate politeness battled fear, and confusion battled lust — although whether for myself or for him I couldn’t say — until I was almost panting. His eyes widened hopefully.

Stepping back, I held the door open. He came in.

I felt no need to make nervy, banal small talk, and realised my new confidence enabled me to negotiate unusual situations far more easily. It helped that the novel sensation of being adored as a woman was so powerful I could feel it in my bones: a warm, delectable buzz, like electricity. My eyes closed and opened in a languorous blink, as if I had expected him to come back. I felt my smile change, becoming something that felt more mysterious, even to me, because I didn’t know what would happen next.

Deciding to continue with the pretence of making tea, I led him to the kitchen. I didn’t touch him, deciding to let him think it was just tea he was getting.

He stopped by the cabinet, and I paused by the worktop. We looked at each other, and then he put his hands either side of my jaw, tilted up my face, and kissed my mouth.

Sensations rushed me: his unique, pleasant taste that was almost herbal, the feel of his hands — which were hard but not rough — and a firm grip. He didn’t crush me, even though I did want to be crushed, and overwhelmed.

Nonetheless I felt slightly removed, as if this encounter was happening to someone else. Had I been wrong about it all? Or was it just so unfamiliar that my entire being was trying to catch up?

Then he held me closer, and everything felt perfect. I heard myself sigh as he kissed me harder, stroking the back of my neck, and my hair, although not hard enough to mess it up or move it. Instead, the touch was so gentle the wig felt like my own hair, and the silicone breasts like my own breasts, so sensitive I shuddered when he touched them.

He lifted me onto the worktop, and I wrapped my legs around him. I felt as if I was in a movie, and yet the sensations were true, and real — the strength in the way he held me, the hunger and impatience in him. Corresponding hunger grew in me, but more steadily, a wave of rising feminine desire rather than the more familiar shot of brute male efficiency. I felt the hard press of his sex against mine as the blue dress rode up, and I as ground myself against him shivers of pleasure ran through me.

“Your mouth,” he gasped in my ear, pulling himself free of his trousers.

“Condom?” I muttered.

He stared.

“I didn’t expect to…”

“No, of course…”

I tried to decide what to do. I wanted him, but I’ve always been picky about sexual health and was even pickier then. He didn’t let go of me, so I lifted my dress further and pressed my naked belly against him. His eyes widened.

“I can feel you –”

He started kissing me again, and the friction was as good for me as it must have been for him. He gripped me so tight I couldn’t breathe, and I adored being held and wanted like that.

He cried out, then shuddered against me as if the electricity in my bones had crackled out and seized him in its ecstatic grip. I felt a jet of wet heat all the way up to my breasts, and then another. Still he juddered on, but silently, as if sound had been burned out of him. Then he snarled with a fierce joy and inhaled the scent of my neck as his body calmed and he gasped for breath.

I was stunned with delight. Uninterested in coming, the experience and intimacy were everything. I felt them in my very cells, as if this joining had been the final part of my transformation. We stared at each other, shocked. There was a trace of guilt in his astonished look, and I noticed his wedding ring.

“That… was naughty,” he said.

I smiled.

“Will you be okay driving?”

He chuckled.

“I think so.”

He kissed me again, on the cheek this time. I saw him out, then closed the door.

Thoughtfully, I went back upstairs and looked at my reflection in the bathroom mirror. My lipstick was blurred on the upper lip. As I set about correcting it, I noticed my hands didn’t shake.

I realised I had changed once again, this time to accommodate a new erotic identity. This, then, is a woman’s life.

How I loved it.