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. Please read the first two parts so you can fully appreciate the story.
All feedback is appreciated - email me: spaceboy_4192@hotmail.com
===== Amy's New Life: Part 3 by Spaceboy
This morning I slept in, waking up at just after 10am. I'd prearranged to take today off work in order to give myself enough time to finish moving. Today would involve a few chores, a few phonecalls and some shopping. Wiping away a piece of dry cum from under my eye, I figured I could get it all done before lunch then have the rest of the day to enjoy myself.
Time passes quickly when you've got the right incentive driving you on. I couldn't stop thinking about Robert and his offer. Of course, I didn't need to think over my decision at all, I knew I wanted him to organise a housewarming for me. What such an event might involve, I had no idea... but I was desperate to find out.
After scoffing down some sushi for lunch, I showered again, relishing the desire to abandon my boy clothes. Wrapped in a towel, I made a beeline for the third drawer of my bedside chest. Despite knowing what I wanted, the rows of lingerie still kept me entranced for a few minutes as I ran my fingers across them and savoured the way they felt.
My outfit was simple yet sexy. A slinky black halter top with a neckline that plunged just shy of my belly button, exposing my hairless chest and offering a tantalising glimpse of my nipples when I turned or leaned forward. A silvery pink mini skirt that sat low on my hips and yet barely covered my round ass. A black nylon mesh thong so skimpy it cupped my balls tightly and left the head of my cock peeking over the hem. Finally, a pair of pumps with light pink straps and 2-inch heels.
Sitting in front of the mirror, I applied a minimal amount of makeup: a touch of blush, eye-liner and lipstick. My dark fringe sat neatly in what resembled a overgrown pixie cut. I blew myself a kiss in the mirror. I knew I was hot.
It was a bright sunny day outside, but I had other plans for this afternoon. I switched on my laptop and started surfing for porn. Clips of large-breasted women sucking cock after cock left me aroused but ultimately unfulfilled. On one site I clicked on the "Gay" section and browsed the thumbnails, my cock growing harder with each page until I saw a clip entitled "My Two Daddies". I clicked on it and watched a young man, probably my age, servicing two older men as they sat on a couch.
The two men were at least 50. They both wore business suits with the shirts unbuttoned so I could see their hairy chests and bellies. The young man was on his knees, unzipping their flies in turn and wrapping his lips around the thick poles he found inside. Later, he was on all fours on the couch with one man fucking him from behind while the second fucked his face.
Watching these two, slightly overweight, slightly greying, but very masculine men fucking someone who could well have been me sent me over the edge. I came hard, shooting cum across my thigh and down my leg.
After cleaning up the mess, I logged into an old dating site I'd opened an account at a while ago. My profile was still active, listing me as interested in meeting up with girls aged 18 to 25 for "fun times". Previously I'd just flicked through the profiles, checking out girls who were brave enough to include nude photos. I'd never actually made contact with anyone on there.
This time would be different, I decided. I searched for "Men looking for Women" and filtered by height (6-foot and above) and endowment (over 8-inches). The results produced many pages of naked, well-hung men and I gazed longingly at their large cocks, especially any that were uncut, hairy and not fully erect.
Curious, I searched next for "Transgender looking for Men" and filtered by age (18-30), which returned fewer pages, but this time the profile pics showed a host of "girls" ranging from stunning shemales to ugly blokes in stockings to cute boys similar to myself. One profile caught my eye: "MissRachel".
"MissRachel" was a 22-year old Asian boy with long black hair (or a very convincing wig), smooth golden skin, a face that reminded me of Zhang Ziyi (from Crouching Tiger, Hidden Dragon), and a very sexy collection of lingerie. Most intriguingly of all, his profile expressed a desire for like-minded playmates.
Inspiration had struck. I returned to my own profile, changed my name to "Amy's New Life", edited my status to that of a "Transgender" and quickly typed up a new description of myself that focused on my urge to cross-dress. I then copied Rachel's description of her preferred partner to highlight just how like-minded we were.
Next, I turned on my laptop's webcam and snapped a few pics of myself in various poses on the couch: sitting with legs crossed; lying on my side; from behind while leaning over the back of the couch and offering a glimpse up my skirt; and lastly, the same position but with my finger pulling aside my g-string to show off my delicious pink hole.
With breathless excitement, I uploaded my new photos and activated my revised profile. I returned to Rachel's profile and, noticing she wasn't online, sent her a wink. The deed now done, all I could do was wait. I sat back on the couch and breathed deeply, my skin tingling with anticipation. Amy's New Life, indeed.
Blip!
My laptop speaker sounded an alert. I sat up quickly and saw that someone had messaged me on the dating site. "HardDude" had sent me a wink. I checked his profile and felt my cock stir again as I looked through twelve photos of his erection, each taken from a different angle.
He was 44, 5'11" and 100kgs. His dick wasn't as long as the ones I'd seen earlier (he said it was 7-inches) but it seemed very thick, perhaps twice the width of my own. He was uncut and his foreskin hung loosely from the exposed head even when fully erect before giving way to a dense tangle of brown pubic hair at the base. Within the cropped photos, I could see the hair reach out up over his large stomach (he had something of a beer gut) and down his legs. No face photo though.
I replied with my own wink, saying I was interested and he should message me. Within minutes he'd done exactly that: "Hey there sexy, I'd love to taste that sweet hole of yours. Are you ready for a real man, baby?"
Upon reading his lurid suggestion, my cock stiffened and leaked a drop of pre-cum. What would happen if I said yes? Do I really want to meet up with this random guy? His hairy dick was turning me on, but I couldn't see his face.
"Hi," I replied, "How did you guess I'm waiting for a real man? I love your big thick cock, but I wanna see what the rest of you looks like. Do you have a full body and face pic? It's only fair when you can see mine."
Again, it didn't take long for a follow-up message to hit my inbox. He'd granted me access to his private photo gallery, which I duly inspected. Inside he had a couple of pics of himself dressed in shorts and t-shirt, hanging out at what looked like a backyard BBQ with a beer in his hand. He was average looking and stocky, like a former Rugby player, and appeared for all the world like a typical Aussie bloke.
Clicking back to his profile, I noticed his preferred partner to be "Women" and his description implied he was married but looking to have some fun on the side. For some reason, the idea that this apparently straight, middle-aged man wanted to fuck my sweet smooth ass was possibly the most erotic suggestion my mind had ever entertained. I didn't care that he was overweight, barely taller than me and not particularly good-looking.
He'd clearly grown impatient with my lack of response - and fair enough, I'd been stroking my cock for about ten minutes now while looking at his photos. So he sent me a chat request.
Okay, now this was a big moment. I gasped as I accepted it. My palms were starting to feel sticky, and not just from the pre-cum running down my fingers.
"Hey there sexy," he said again. "U there?"
"Hi!" I entered, wanting to give the impression of confidence.
"Love ur pics ur so hot." Oh dear, I really hate txt speak.
"Thanks. I think you're pretty hot too," I lied. Or did I?
"Where do u live? Wanna have sum fun tonite?"
"The inner west, Newtown actually. How about you?"
"Cool i work in the city. R u up 4 fun now?" I suspected he'd be telling his wife he'd be working late tonight.
"Maybe." The critical moment was approaching fast. Could I really go through with this?
"Im free tonite. Can u dress up 4 me?"
"How about later in the week? I'm kinda busy tonight." I chickened out.
"I wanna fuck u so hard."
"I'd like that too. Are you free Thursday or Friday?" Surely by then I'd have summoned the courage to do this.
"Damn babe i wish i could have u tonite ur so sexy." He's definitely told the wife he's working late.
"Aww thank you!"
"Ur as hot as any girl on here."
I sent a blushing smiley. I'm pretty sure I could feel my cheeks get warmer.
"Maybe friday i can cum over n feed u my cock. U like to suck?" I'm betting his wife doesn't go down on him any more.
"I do. Especially thick hairy cocks like yours."
"Wow u know what real men like yea? U gonna wership my thick cock?"
"Oh I will. I'll worship your cock all night. Until I beg you to cum on my face."
"Damn baby i need u now! U swallow 2?" And I'll raise that bet that she never once swallowed.
"Of course, but only when you tell me to." I was warming to this now. Were men really this easy to tease?
He took a little longer than usual to reply. I'm guessing he'd... finished.
"Wow! i fkn luv u honey i cant wait for friday"
"Me too!"
"Gotta go now. C u later."
And with that he disconnected. Once again I slumped back onto the couch. I'd just made a man cum. Sure, it was just chat, but he was getting off on my photos as well as whatever lines I was feeding him. He really wanted to fuck me - at least in his cyber fantasy - and that had me so excited.
I was sitting back on the couch, heels resting on the edge of the coffee table, legs apart, and my little cock head was poking out from beneath my skirt. I touched my thighs and closed my eyes, gently stroking myself all the way up to my ass. My skin felt so smooth, so soft... so feminine.
Does a man like "HardDude" see me as a girl? Imagining myself kneeling before him, my tongue circling around the head of his fat cock, I wondered if I could pass for a girl. I imagined him lifting me up, placing his strong arms around my waist and pulling me in close to his body. I felt so small, so fragile... so safe.
As I looked up into his eyes, it was no longer "HardDude" holding me, but Robert. I felt the hair on his torso brushing against my nipples. I felt the bulge in his jeans pressing warmly against my tummy. He leaned forward and kissed me...
Blip!
Startled once more, my eyes flashed open. Oh, another message. This time from "MissRachel". I clicked on it and held my breath.
"Hi Amy! Thanks for your wink. Are you new on here? I hadn't noticed you before. And, trust me, I wouldn't have forgotten someone as gorgeous as yourself! :-D Seems like share at least one hobby. I'd love to chat with you or meet up. It's fun to dress up together, swap makeup tips, stories about boys, you know just regular "girl" stuff. ;-) Say hi any time, sweetie! Kisses, Rach"
Reading her message made me feel happy. Deep down I think I'd always wanted to find someone I could share my fantasies with, no matter how much I convinced myself I wanted them to remain secrets. Being sprung by Robert last night was one thing, but having a friend who felt the same way and had the same fantasies was more special.
I composed my reply quickly.
"Hey Rachel! I'm really glad you got back to me so quickly. And I really appreciate your kind compliments, although I have to say you are far more beautiful than I am. You're right, too, I am new - I've only just moved to the city on my own and I guess I'm looking for friends. Would you like to email me (spaceboy_4192@hotmail.com) and we can talk more there and maybe arrange a date? Love, Amy."
I hit send. After that I felt like I needed a drink and a smoke. In the kitchen I poured myself a vodka, lime and soda (my fave, in case you hadn't guessed) and then stepped out onto the balcony. The fading sunlight surprised me - had I really been online for that long? Then I thought about Robert. Maybe he'll be home soon. Settling onto one of my two deckchairs, I lit a cigarette and waited.
Soon it was night. I'd refilled my glass three times, smoked half a dozen cigarettes and received over ten winks and messages from horny guys before I noticed Robert's apartment lights come on. About 15 minutes later I heard his balcony door open and his footsteps approach, pause momentarily as he lit a cigarette, then continue to the wall divider.
"Good evening, Amy," said Robert, peering around the wall. "Mind if I join you?"
"Hey, not at all."
He placed one foot on the rail and vaulted over with ease. Like last night, he was naked from the waist up, with just jeans and sandals below.
I uncrossed and recrossed my legs as Robert sat down on the second chair. I just realised my skirt was so short it wasn't really covering any of my ass.
"You look just as sexy tonight as you did last night," he said. I was blushing again. I was putty in his hand.
"You look like you haven't even changed your clothes," I smirked. "I hope you're at least wearing fresh underwear."
"How do you know I'm wearing any at all?" Robert laughed. I shot him a look of mock horror.
"Can I get you a drink? Vodka? Scotch? Beer?" I stood up, feeling just a little tipsy after four vodkas.
"Scotch please. Straight."
My heels clicked across the concrete as I walked inside. My skirt was riding up from being seated and I knew my ass cheeks would be showing. With my backless halter top, I was virtually naked from behind. I was buzzing - and not just from the alcohol.
I refilled my glass - a double shot this time - and fixed Robert's scotch. When I re-emerged, he'd stood up and was looking out over the railing. I moved in next to him, feeling the heat of his body next to me. We each lit another cigarette.
"So, did you think about my offer?"
"I did. I think I'd like a party. I'd like to get to know you better... and meet your friends."
"Excellent," Robert touched the small of my bare back. His hand felt huge. I briefly pictured him holding me around the waist, his fingers almost wrapping the whole way around me. "I tell you what, I'd planned to have a barbecue on Friday night. Why don't you come and meet a few of my friends, then we'll have your housewarming party on Saturday. How does that sound?"
"Wow. That's sounds great!" His friends? Would I be meeting them as Andy or Amy?
"Is there anyone you'd like to invite along?"
"Hmm. I can think of at least one person." Rachel, of course. I'll have to message her again soon.
"Great. I look forward to meeting them. Amy, I'm going to make sure you have a party to remember."
With that, he stepped behind me and slid his arms around my waist. I leaned back into his body and closed my eyes as his lips brushed across my neck.
"God, you're so gorgeous," Robert whispered into my ear. His left arm wrapped around my body, while his right hand massaged my nipples. He kissed my cheek slowly. My cock strained the very limit of my panties. The feeling was incredible.
He spun me around and I was staring directly at his muscular chest. His hands moved down underneath my butt to lift me up off the ground. Leaning forward he pressed his lips against mine, his stubble tickling my face, and kissed me. I welcomed his tongue into my mouth and licked it, sucked it, tasted it. Our lips remained locked for what seemed like days.
Finally he broke away and put me back down on the ground. I looked up at his eyes and mouth with a mixture of longing and disappointment. I'd just kissed a man for the first time and I wanted more. No, I needed more.
(to be continued)