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 second chapter contains cross-dressing scenes and masturbation, but no sex just yet. We're getting closer though, so please stick with me!
All feedback is appreciated - email me: spaceboy_4192@hotmail.com
===== Amy's New Life: Part 2 by Spaceboy
Robert smiled when he saw me emerge. My hands were shaking as I passed a cigarette over the wall and then lit it for him. Up close he towered over me, despite my heels. Of course, I wasn't in any way tall, even with my heels I was barely 5'10". He must have been well over six foot.
"Thanks," he said, warmly, exhaling into the night air.
He looked me up and down one more time. "So tell me, do you often dress like this?"
"Um... kinda, yeah," I whispered, feeling a sensation halfway between excitement and relief. "It just feels nice, I guess."
Thinking quickly, I added with a nervous smile, "Do you... often dress like that? You know... without a shirt?"
Robert laughed. "You've got me there. I'm not usually quite so underdressed, but on nights like this I guess it just feels nice, too."
I couldn't help but giggle. I think I decided at that moment that I liked him. As I took another sip on my drink, I glanced down at his jeans and realised from the sizeable bulge in his crotch that he'd probably decided he liked me too.
"Have you finished unpacking all your things?" Robert asked. "If you need any help moving any heavy furniture, I'd be happy to lend a hand."
"Thanks, um..." I started, my mind racing at the thought of this guy in my apartment. "I'm pretty much done now, but I'll let you know."
You idiot, I thought.
"Uh... dressing like this is, um... my reward for getting everything done," I finished, still confused as to why I felt like an idiot.
"Looks like a very good way to celebrate," said Robert, smiling again with genuine warmth. "Speaking of which, have you any plans for a housewarming party?"
"I hadn't really thought about that. I don't really know anyone here."
"I'd say that's the very reason for having one. I tell you what, how about you leave it to me to organise. I'll introduce you to some of my friends. I'm sure they'll like you."
A buzz of excitement ran through my body, although I didn't fully understand what I was feeling. And why did he say "they'll like me" rather than "I'll like them"?
Sensing my hesitation, Robert stubbed out his cigarette and continued. "Well, the offer stands. Have a think about it and let me know. I promise it'll be fun."
"Yeah, okay, thanks, I will."
Robert reached out and placed his hand on my shoulder. His fingers were thick and heavy. "You look tired. You should get some rest after your weekend." His fingers gently moved down my arm, caressing my soft smooth skin. "I need to hit the hay as well, early start tomorrow. Maybe I'll see you tomorrow night? We can discuss it further then."
"Yeah, that sounds good." My voice was a whisper. All I could think about was his warm hand on my arm.
"Have a good night then. It was a pleasure chatting with you... Andy," he said, withdrawing his hand and stepping away.
Without knowing why, I said, "It's Amy, actually... when I'm... like this."
"Well, Amy, I hope we speak again soon. Oh, and next time, no need to be so shy, I think you look lovely like that."
I could feel myself blushing. I hope he hasn't noticed... Wait a second, what's going on? Why is he making feel so strange?
"Um... I like that you like that, too."
Robert gave me a wink and wished me a good night again, before walking back into his apartment. I remained next to the railing for a few moments, my cheeks still red, my heart still racing and my cock still hard.
I thought I could feel an extra sway in my hips as I walked back inside. Kicking my heels off, I got ready for bed and slid under the covers still clad in nightie and knickers. My mind continued to race as I rubbed my little cock and tight balls through the lace.
Images of Robert's smile, his hairy chest, the bulge in his pants, and his hands on my arm all filled my head. I pulled my hard cock free and began to stroke it, slowly at first. Measuring just 5-inches, I'd never felt insecure about the size of my cock. It was just the right size, I thought, at least for my small hands to wrap around. And the right shape, too: just a little bit chubby around the middle while the pink head didn't mushroom out too much. I was circumcised, albeit close to the head so I could still roll enough foreskin over the glands while masturbating.
Spitting in my right hand, I began to pump my cock faster, massaging my smooth balls with my left. Considering how horny I was from the events of the evening, it didn't take long before I was close to cumming. I kicked off the sheets and flipped my feet over my head in a half-somersault, my ass sticking straight up into the air with my panties clinging to my thighs. With my cock now positioned pointing down at my face, I spasmed as the first stream of cum hit my lips. The second traced an arc across my left cheek. The third landed inside my mouth. The fourth snaked down my right cheek and chin. I squeezed the final few drops out and they too fell into my eager mouth. I licked my lips, swallowed, and soon drifted off to sleep, cum still streaked across my smooth pink face.
(to be continued)