The Making of a Sissy Pt. 01

*This story, the names of the characters are all fictional and are over the age of 18"

*This story consists of characters from different ethnicities and age group. Viewers' discretion is advised."

Hello! My name is Eddy, an occasional Crossdresser going by the name Charlene. Born in a middle-class family somewhere in Asia. The story takes place on different parts of the continent therefore I might split it up into multiple parts. Hope you enjoy!

*Story begins here* Starts slow to get you to really get in my character and gets steamy later*

The year was 2002. I was 18 and in my final year of high school in a boarding school somewhere in Asia when my parents suddenly decided to send me off to New Zealand to study. This didn't really bother me as I've always been a "drifter" (I will get back to this somewhere in the other stories). We have some siblings over there and they helped set up things for my stay. For those who don't know, being an International Student meant you had to find a host family, to help settle into the new environment. (This was because I chose a different city from my siblings as I wanted to be alone and start fresh).

A little bit about me. I was still 5'4 when I was 18 (but later grew to 5'11) and weighing in at 150lbs. I was skinny but I've always had some round ass thanks to genetics. For real.

A few days before departure the school emailed me information about the school and my new host family. They were an older Dutch couple in their early 70s. Their smile put all my anxiety away as I've been told some host families can be very shitty and mean to their students.

My mom brought me to the airport and kissed me goodbye. I teared up a little as I turned around but soon filled with joy and excitement from the adventure I'm about to embark on. 12 hours later I arrived at Christchurch airport. My English wasn't good. Even though I've had English lessons since I was 8 this is the very first time to actually be in an English environment and I was a bit overwhelmed going through customs.

Finally making it out to the arrival hall I noticed my new (host)family. Turner and Joanna (unusual names for Dutch maybe but I had to change the names), or as the family calls them, Opa and Oma (Dutch for Grandpa and Grandma). Opa is about 5'8 and 176lbs, wearing his signature Ivy Cap with a checked shirt under his cardigan. They both gave me a big welcome hug and kiss on the cheek. I got to say this was when culture shock really hit lol.

We arrive where I would call home for a while after a 30-minute-drive. I loved everything about New Zealand. The weather, the air, the scenery, the architecture and so much more. Our first place was a 2-bedroom house filled with beautiful European decorations. Now it wasn't a fancy or rich household, but it felt like home as soon as I stepped foot in it. There was a queen size bed in the master bedroom and 2 singles in the other room. I quickly learned that they had to sleep separately due to a condition in Oma's spine that she needed a special bed. So, I had to sleep in the same room as her. I didn't care too much as I won't be the one suffering from hearing loud snoring at night haha.

We lived across a small park and next to a preschool on a quiet street in the Northeast suburb of Christchurch. The house came with a rather large garden and Turner LOVED gardening. He perfected his craft in the garden. It was the most beautiful garden I've ever seen in a home. He did all the cooking in the house also. I still miss his cooking to this day. Joanna was a fantastic baker. Loved her cakes and biscuits with the perfect cup of hot Milo.

Times goes by and we got closer. Much closer to the point where they started to treat me as their own grandson. I too started to see them as my grandpa and grandma. One of Turner's hobbies in the afternoon was to drive to a nearby forest trail and go for a walk. I would sometimes join him after school or on the weekends to explore the beauty of nature, as I too came from a rural area and loved nature.

I would get 1 hour of computer time after dinner every day on their computer, which was in the study, and dial-up internet. I was a teen so I loved gaming and going through forums (much like Literotica) but my fetish was always older women back then. I would read erotic stories online about sex with milfs or even with moms. These forums were all in my language of course so they wouldn't understand if they ever checked the browser history.

One day I was going through the categories of stories, and I noticed something called "Crossdressing" and I was curious to what it was about. I clicked in and began reading through stories after stories and it blew my mind away. The thought of dressing as a girl and be touched by another man felt so weird, but yet so kinky. I would often jerk off and cum while reading. Sometimes twice a night. Being 18 and somewhat naive (I was still a virgin) I would wipe my cum with my pajamas top, which I thought was a good idea back then. This would go on for months before things started to take a turn.

It was one night we hugged and kissed each other before heading to bed and as i laid down two of the wooden boards supporting the mattress broke causing the end of my bed to drop to the floor. Opa heard the noise and quickly came to our room as me and Oma stood in shock. Where was I to sleep? I suggested the couch, but they loved me too much to let me sleep on the couch.

"Jump in my bed then" said Opa "We'll fix the bed tomorrow when you're at school."

Me and Oma didn't think much and nodded. I left the room and made my way to the master bedroom. It was my first time being in here at night and to be honest I was kind of nervous as I got in the bed.

"Don't worry about it. I'm not gonna bite ya, my teeth are out in the bathroom" said Opa while laughing. I laughed as I looked at his gums as both his top and bottom teeth were fake. I was relieved. This was the first time in bed with another man and I was a bit nervous but knowing it's the loving and caring Opa next to me I felt somewhat at ease. He wouldn't hurt me.

The bed was fixed the next day I got home from school. Everything went back to normal for the school year and I went back home during the summer holidays.

I was back and ready for school 2 months later. Nothing changed. But during the holidays I've been digging so much into crossdressing and eventually started fantasying about and older man fucking me. I knew I wasn't gay but imagining myself as a girl was totally different and turned me on so much.

I started seeing Opa differently sometimes. I started to notice that his hands are so much bigger and thicker than mine to the point where he cuts his nails with big pair of scissors. His hugs started to feel different from a year ago as I would hug him tighter than before. The light smells of tobacco on his face and stubble on his jaw and chin was something I never noticed before.

When I said we got close, we really got close. I was 18 but my dad was always away for work, so I never really had a father figure. This led to a lot of questioning within me and Opa became that father figure I never really had when I was little. I've always been scared of ghosts and monsters and crazy people like burglars, it became common in the area we lived in, so the night scares me. a lot.

One night when they were watching TV after dinner, I decided to go shower. It was pitch dark in the house except the living room, so I started to get scared. What if someone snuck in the shower through the open window? What if there's a ghost? All these ran through my head, and I was dead scared now. I thought about turning on all the lights in the rooms, but they did not like wasting power.

"I got it! Why not get Opa to stand in the bathroom with me while I'm in the shower!" This was the perfect idea. "All I have to do is to get in the shower before he comes in and ask him to leave before I come out to dry myself!"

I walked next to the couch and shyly asked Opa while scratching my head "Hey can you come in the shower with me? I'm really scared, and I don't think I can shower alone with all the news about burglars..."

They both looked up in shock and disbelief. "Beg you pardon?" They both said almost simultaneously.

"Yeah, I'm honestly scared, and it would help if Opa can talk to me in the shower, so I know I'm safe," I replied slowly.

They looked at each other and Opa being the man he is decided to help his Asian grandson.

"Let's go kid. Make it quick. I don't want to miss the show you know." Opa said. Oma just turned back to watching TV.

Nothing special happened in the shower but it did comfort me. We would chat and crack jokes. It also kind of turned me on knowing I'm butt naked so close to a man. This thought excites me a lot and I loved it. I was done in 5 minutes and asked him to leave before I got out.

This went on for a few weeks until one day I decided to try something new to see his reaction. We were in the shower as usual as he stood leaning to the wall talking to me. I turned off the water as I finished showering. I heard him started to move towards the door to go out. I opened the shower door before he reached the bathroom doorknob, revealing my naked body to him.

I was rather skinny back in this time, and I don't have much body hair, everything was smooth except down south.

He turned his head as he heard the door open and saw my naked body. Almost hairless, skinny, kind of like a girl but not quite.

"Are you okay?" he asked with a smile on his face. I noticed he was eyeing my up and down.

"Oh, I thought you went out already" I replied "Sorry. I'm gonna grab the towel now."

"Okay as long as you're okay. I'm gonna go back to TV now. Don't catch a cold boy!" he said while laughing and exiting the bathroom.

This was the trigger to start it all.

The next day went by as usual. Got home from school and had dinner. I was ready to shower and noticed Opa was waiting at the dining table while Oma was watching TV in the living room.

"Ready to shower? Let's go!" he looked at me and smiled. I didn't think much and started to walk towards the bathroom. Only this time Opa was following me in.

My heart started racing and the thought of undressing in front of him turned me on so much.

We both got in the bathroom and looked at each other. He smiled and said "It's okay. Do your thing. I'm not gonna bite you" His smile was one of the most comforting things in the world and that made me felt peace.

I turned my back on him and started undressing. I was turned on but this time i didn't get hard. I could feel pre cum slowly coming out of the head of my cock but i was still soft. I tried to mimic a girl undressing to hopefully give him a show while he watched me get butt naked.

"I'm really doing this!" I thought to myself.

I turned around and saw him eyeing my up and down but this time i saw a spark in his eyes. "Is he turned on by this?" I thought to myself as I saw something that blew my mind. I saw a small bulge in his khaki pants. "Am I turning him on?!" I screamed in my head.

"Go on! Go shower. I have a show to catch on TV" He rushed me in a playful tone.

I didn't ask him to leave when I came out this time. I let him watch me dry myself. He left before I got fully dressed again. I think at this point we both had an understanding that we keep this secret to ourselves.

*End of part 1 *