This story is a work of fiction intended for adults only. It tells the tale of a young man who discovers a new life as a transvestite when he moves out of home. This opening chapter contains cross-dressing scenes but no sex just yet. Future installments will include depictions of sex between men of various adult ages. I hope you like it.
===== Amy's New Life: Part 1 by Spaceboy
Moving into my first apartment had been an exhausting experience. Late on Sunday night, after two full days of unpacking boxes and rearranging furniture, I knew there was only one way I could feel fully relaxed.
With steam pouring from the hot bath and filling the room, I slipped out of the day's clothes. Jeans, polo shirt, boxers were discarded; my naked body was soon covered in the sweet luxuriousness of lavender and tea tree oil.
I lay back against the tub and closed my eyes. I'd finally done it. Just a few weeks shy of my 21st birthday, I finally had a place of my own. It wasn't that living with my parents had been particularly miserable - they were both generous and loving - but it felt so good to now have my own space. A new chapter in my life had begun.
Snapping out of my reverie, I took the opportunity to shave the few areas of my body that weren't already smooth. I was kinda lucky, I guess, in that I never could grow much hair on my arms, legs, chest and wherever else a guy usually sports some fur. Even the concept of facial hair was foreign to me.
Out of the bath and wrapped in a clean towel, I paused in front of the mirror. I like to think I'm cute, my slender frame and fine features lend me something of an angelic boyishness. I've a nice smile, although kinda shy at the same time, short and messy dark hair, grey eyes and pale skin. Oh, and my name's Andy...
But on nights like tonight, I'd prefer it if you called me Amy.
Tiptoeing from the bathroom to my adjacent bedroom, I headed straight for my chest of drawers, the third drawer from the top, to be precise. Inside lay my favourite clothes: rows of pink satin, white lace, red silk and black sheer. A wicked grin lit up my face as I considered the possibilities.
Eventually I decided on a fairly simple combination, removing a baby doll nightie (sheer black with pink lace trimmings and a pretty pink ribbon tying it together on the chest) and matching French knickers (black lace with pink hems). As I sat on the bed I slowly drew the lace knickers up my smooth slim legs and then stood up to ease my rounded butt inside the tight material. They felt amazing.
My semi-erect cock stretched the lace front, so I adjusted myself, easing my 5-inches to rest across the top of my right thigh. I preferred to not tuck it away between my legs. Instead I loved to see the outline of my hard cock straining against my panties. Already I could see a slight damp patch near the head...
Next I slipped inside the baby doll nightie before fastening the ribbon at the front. It exposed my taut tummy at the front and barely covered half my butt at the back. I touched my nipples through the sheer material and sighed with pleasure.
Last but least were the shoes. I knelt down beside my bed and peered underneath, making sure my ass was poking as high into the air as possible. There they were: I snatched my two-inch black heels, stood up again and eased my feet under the tight leather straps.
I turned to face the mirror, posing with one hand on hip and pouting as seductively as I could. My hair was still messy, the fringe would soon be creeping down over my eyes, but I liked it that way and - truthfully - felt too lazy to drag out a wig. If I thought I looked cute in the towel in the bathroom before, then I thought I looked hot now.
I had moved to the inner west of Sydney and had been lucky enough to find myself a rooftop apartment (one bedroom). The balcony was huge, wrapping around the western and northern sides of the building. At either end, there was a diagonal wall from balcony railing to roof that divided my apartment from the common rooftop area to the east and my neighbour to the south.
Fixing myself a drink (vodka, ice and lime) on the way, I stepped out onto my balcony to admire the city skyline at night. To the north I could see the city lights, a thick constellation of whites, blues, yellows and reds. It looked beauitful. Lighting a cigarette, I walked over to the western railing and - looking away from the city - was able to make out the stars above. I felt liberated.
Just then a noise startled me. It had come from behind me to the left. A door sliding open. Then footsteps. My neighbour had stepped out onto the balcony. I tensed up.
I'd seen my neighbour a couple of times already this weekend. Once when he arrived home while I was holding my front door open for the removalist men. Then once again when we shared the lift ride down all five floors as we'd both decided to grab our Sunday morning coffees at the same time. He seemed nice enough from the few seconds of small talk we'd exchanged. Tall, broad-shouldered and probably twice my age.
What if he sees me? I thought. If he walks to the railing and looks over he'll see me, for sure (thanks to the peculiarly sloped divide between the two properties). Dressing in lingerie was my secret, no one else knew. It was something I did - and had done for about four years now - because it turned me on. It turned me on like nothing else could do, certainly more than the sex with my old girlfriends had ever done.
I considered myself straight. I mean, I'd only had sex with girls, a mere four in total. But I loved dressing in lingerie. And I loved watching straight porn while doing so. And every time I would imagine I was the girl. It wasn't that I necessarily found men attractive; it was a fantasy. Which is why I had to keep it secret. I guess I was scared about what would happen if anyone found out
I held my breath, standing there against the balcony railing. Maybe it was the feeling of being somewhere new. Maybe it was the liberation I felt of being untethered from my childhood. Maybe it was the vodka. But I didn't move.
Out of the corner of my eye I caught movement and the footsteps were silenced. He must be standing at the edge of his balcony now, maybe ten metres from me. I remained focused on the stars in the western sky, in my left hand a glass, in my right a cigarette. The cool night air breezed through my nightie and tickled my skin. I could feel my nipples harden. Another drag on my cigarette as I tried to remain calm. My cock - previously flaccid - was now stirring under tight lace.
"Hi..." came a deep voice to my left. Somewhat uncertainly, he added, "Is that... Andy?"
His name was Robert. I was pleased I'd remembered that and surprised he'd remembered mine. I turned his way, swallowed nervously, and when my eyes met his I quickly took another drag on my cigarette.
"Uh...", I mouthed. "Yeah."
"Hi..." he repeated. His eyes were still wide as he looked me up and down. He had the slightly weathered tan of someone who enjoys the outdoors. Short sandy brown hair gave way to well-manicured stubble along his jaw. As I studied his masculine features, I could've sworn his gaze kept flicking between my bashful eyes and my crotch. Understandably so, I guess.
"I'm sorry if I scared you," he continued, rightly assessing that I was too dumbstruck to speak. "I heard you opening the balcony door, so I thought I'd come out and say hello."
If he couldn't take his eyes off my crotch - and the outline of my gradually stiffening cock - then I couldn't look anywhere but his chest. He wasn't wearing a shirt, just a pair of jeans. Thick brown hair covered his well-defined chest and most of his stomach before the trail disappeared beneath denim. He was in extremely good shape for someone of his age.
"I, uh... could also smell your cigarette," he laughed, "and thought I might be able to pinch one from you."
He'd already stepped up to the dividing wall at the limit of his balcony before I realised what to do.
"Oh, sorry," I gasped. "My pack's just inside."
Tottering in my heels towards the apartment, the reflection in the glass balcony door enabled me to see him lean forward and watch me disappear inside. I ducked into the kitchen and fumbled for my cigarettes. All alone now, I suddenly realised how quickly my heart was beating. I'd been sprung. My secret was out now. My neighbour knows it. He was leering at me. He just checked out my ass. What should I do?
My cock was now fully erect. Again I adjusted it so it lay flat across the top of my right thigh. I poured myself a shot of vodka and downed it in one gulp. I breathed deeply, picked up the packet of cigarettes and went back outside.
(To be continued)