Becoming Amy! Ch. 01

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A young man discovers the ladyboy inside him!
1.7k words
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Part 1 of the 5 part series

Updated 07/12/2023
Created 06/14/2023
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My name is Amphai Blom. I'm half Swedish (dad's side) and half Thai (mom's side). I'm an only child and just graduated from high school. I'm still living with my parents, staying in the same room I grew up in and going to the local community college in the fall. Hopefully, that way I can save enough money to finish up at the State college for my junior and senior years of school.

I'm sure you can't tell from my name, but I'm a boy. Probably not masculine enough for my dad, but a boy, nonetheless. Think 'Thor' from the movies if you want to get a good idea about what my dad looks like. If you've ever heard of Areeya Chumsai (Miss Thailand, 1994) that's who my mom looks like.

Unfortunately for me, I look way more like my mom than my dad. I'm 5' 9" tall, slender, maybe 135 pounds. I'm dark complected and have baby smooth skin. The only nod to the Swedish side of me are my sparkling, crystal blue eyes. I've always worn my raven black hair long, yet one more thing that annoys my dad although he's kind enough not to say anything. He doesn't have to, I can tell.

My parents met when my dad was on a trip to Thailand. He was helping a company in Bangkok implement a new IT security system, my mom was the local in charge of the company's side of things. They hit it off almost immediately and when my dad came back to the States, my mom came with him. I was born less than a year later.

We'd just gotten back from a funeral. Our next-door neighbor, Tom Mason, had lost his wife, Colette, unexpectedly. She'd been involved in a terrible car accident and never regained consciousness. They had been our next-door neighbors for a few years. They moved in just before I started high school. Despite being much younger than my parents, the four of them had become fast friends and were always doing things together. Tom and Colette didn't have any children, they said they wanted to wait a little longer.

Our family was there for Tom. We made sure he had all the support he needed. I was constantly taking meals to the house for him that first week afterwards. Tom was very appreciative and kept telling me if there was anything I needed to let him know.

The next weekend, my parents were flying to Vegas. Nothing special, they just liked to take weekend getaways together ever since I'd been old enough to stay at the house by myself. Plus, they had the added assurance of Tom and Colette being right next door.

As soon as they left, I hurdled up the stairs, two at a time, to the bathroom. I began to run the hottest tub I could stand and added Opium bath oils. I luxuriated in the bubbles, the feel of the oils on my already baby-soft skin and the wonderful feminine smell. I used Opium shampoo and conditioner on my hair twice. I wanted it to be as glowing and lustrous as possible.

If you haven't figured it out yet, I'm a crossdresser. I had been teased relentlessly at school about being a 'ladyboy' because of my feminine features. I had no idea what that meant the first time anyone called me that, but thanks to the internet I was able to figure it out right away. Curious, I was stunned when I saw the incredible beauty of Thailand's ladyboys. I looked at myself in the mirror. "No way I look like that, no way I could ever look like that!" I thought to myself.

Of course, being an only child and having lots of alone time in the house, I began to explore my mother's wardrobe. In the beginning, it was only underwear. The first time I slipped into a pair of my mom's French-cut satin panties, I came almost before I had my raging hard-on settled inside them. That was it, I was hooked. It wasn't long before I was dressing head to toe and shortly after that began to experiment with makeup.

Thanks to all the online tutorials, my makeup skills were excellent in no time, if I do say so myself. I chose Amy as my femme name. Now I was both beloved and beautiful!

I hopped out of the tub, toweled myself dry and powdered myself from head to toe with Opium body powder. I ran to my parents' room, searching for the outfit my mother had worn to the funeral last weekend. It was a black silk skirt suit with a black satin blouse. I found it quickly enough and took it back to the bathroom and hung it from the shower rod.

I went back to their bedroom and raided my mother's lingerie drawer and shoe tree. Returning to the bathroom, I slipped into a pair of black satin and lace panties with matching bra. I slipped my mom's breast inserts into the cups. Aided by the inserts, my breasts filled them up nicely. I rolled the sheerest black thigh high stockings up my legs; the electric feeling that ran through my body was incredible.

I put on the blouse, pencil-skirt, and jacket and then stepped into black silk open-toe stilettos with 4" heels. I sat down at my mother's makeup table and expertly transformed myself into Amy. I had chosen to go with a crimson makeup palette and finished it off with ultra shiny crimson lip gloss.

I went back to my parents' bedroom to look at the results. They had the only full-length mirror in the house. I was walking around, modeling for myself, admiring the way I looked. I was near the window and happened to glance down. Tom and Colette's bedroom was on the first floor of their house; they could see into my parents' room from their room. There had been good-natured teasing from both sides about making sure to keep the blinds closed. I hadn't made sure.

I was looking right into Tom's eyes. I stepped away from the window and stayed out of the line of sight as I left my parents' room. I turned their lights off as I did.

"Shit, shit, shit!" I thought to myself. "Did he see me? Does he know it was me? Shit, shit, shit!" I went to the bathroom, stripped out of my mother's clothes, took a long shower, scrubbing all the makeup and feminine smelling products off my body. It took a long time for me to fall asleep and even then, I only slept in fits and starts.

I was doing yardwork in the back the next morning. I had promised my mom to prune and water her garden while she was gone. "Howdy neighbor." I heard Tom's friendly greeting.

"Hey Tom, how's the weekend going so far?" I tried to sound as nonchalant as possible.

"OK, nothing special. Trying to clear some stuff out of the house. Why not come and take a look, see if there's anything you want before I haul it off to Goodwill?"

I couldn't begin to imagine anything I'd want that Tom was going to give to Goodwill, but I was trying to maintain my cool. "Let me wash my hands and I'll be right over."

He smiled and went back into his house. I washed as much dirt, grime, and sweat from my face and hands as I could get without taking a shower. I knocked on his door. "Come on in. Can I get you anything to drink? Water, soda, a spritzer, beer, wine?"

"I'm good, thanks. Where's the stuff you want me to look at?"

"It's in the guest bedroom, down the hall and to the right. Most of it is on the bed."

I stopped in the doorway and just stared. There was nothing but women's clothing of all kinds piled on the bed. My heart sank into the pit of my stomach.

I walked back into the kitchen. "You saw me last night; I know you saw me. What do you want? Please don't tell my parents, please. Especially my dad, he'd be heartbroken."

"Amphai, I don't want anything. I'm offering you all of Colette's things, everything. I've been going through her stuff all week, planning on getting it out of the house. Then when I saw you last night, dressed up in your mom's clothes, I got this wild idea. You can keep all Colette's things in the guest bedroom, even her makeup and stuff, it has its own bathroom. You can dress up whenever your schedule, or your mom and dad's schedule permits. I just want to be around. I just want to have some female companionship. I miss Colette terribly. I miss the feminine smells, the feminine sounds, the feminine looks around the house and in my life."

"Tom, that's crazy! You want me to be your wife? I'm not gay."

"No, Amphai, no! I'm not asking you to have sex with me. I want a female presence around the house, someone to talk to, someone to share dinner with, someone to just be here occasionally. That someone could be you. It would be a win-win for both of us. You'd get access to an almost unlimited feminine wardrobe without fear of getting caught. And I wouldn't be so lonely all the time."

Tom had the most heartbroken look on his face. I thought he might burst into tears any second. I had to admit, as crazy as it sounded, there was a lot of appeal to what he was proposing. Anything I ever wore belonged to my mom. My style was her style. I had no choice. And I had to be extra careful to put everything back exactly the way I found it.

Tom could see me wavering. "I'll tell you what, I know your parents are still gone. Why not try it out, just for today? If anything about what I'm suggesting doesn't sit right with you, if anything gives you creepy vibes, then you can just say no and call it off."

"This is crazy but.... alright. Is everything of Colette's already in the guest bedroom and guest bathroom?"

I saw Tom smile for the first time in more than a week. "Yes, yes it is."

"It's going to take me a while. I'm not going to be out in 15 minutes!"

"You forget who I was married to. It took Colette forever to get ready! But she was always worth the wait. After seeing you through the window last night, I'm betting you will be too."

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8 Comments
AnonymousAnonymous8 months ago

Very lucky boy the man wants just to have somebody with him hopefully it only continues that way and he doesn't force himself on to the boy

AnonymousAnonymous10 months ago

Lovely descriptions of getting dressed up

AnonymousAnonymous10 months ago

beautiful teaser

AnonymousAnonymous10 months ago

Great start to an intriguing story, we hope to read ch 2 very soon and from a selfish view I need much longer chapters to read from you!! Can I also tell you that I really enjoyed the love story between Carmen and Josh.

Dare

KatiwantsKatiwants10 months ago

A wonderful start!! Next chapter please!!

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