The Making of a Sissy Pt. 06

*recap*

John gave Charlene the best cum she's had before sending her back home to Opa. He also promised to take Charlene on his yacht for a 2-day-cruise the following weekend.

*Part 6 starts*

As I walked home from John's house, I was filled with satisfaction but guilt towards Opa. My legs are weak from what happened earlier with John and walking in heels became a mission.

As I made my way to our house the front door opened as I approached it.

"Heard you walking sweetie." Opa giggled as he led me inside.

"How did it go? Did you enjoy yourself?" he asked with his arm around my waist. He had nothing but shorts on.

"It was good Opa. John said you wanted that to happen. Said that you asked him to show me things?" I asked with guilt.

"Oh well. I figured you can have some fun with someone who can show you something different." he explained with a smile on his face.

"I still love you sweetie." he added.

I nodded and turned to him for a hug.

"Thank you Opa." I mumbled.

"Anything for my sweet little girl!" he said while caressing my back.

"Now, let's have dinner." he led me to the dining table.

"Why don't you get out of your clothes and join me at the table?" he asked.

I stripped off everything right then and there except for my wig, stockings and high heels. They made me feel girly and I didn't want to take that away.

Opa was the best cook. I absolutely loved his food. We chatted over dinner about what happened after he left. He smiled and said, "Sounds like you had an amazing afternoon sweetie."

"So about next weekend. He said we are to spend the night on his yacht out at sea. I'm kind of nervous." I said.

"Oh, don't worry about that sweetie. I'll get you ready." he replied with a big smile on his face. "Why don't you take the afternoon off on Wednesday and I'll pick you up from school and go shopping at the mall?" he added.

"Really?" I said with my eyes wide open with a big smile, "But how?"

"I'll just tell Oma I'm going to visit my brother and pick you up on the way home." he said, "I have it all planned out."

I was super excited and gave him a kiss on his left cheek. "You're the best." I said in his ear.

Oma was home the next day I got home from school. I had my nail polished removed the night before. Everything went back to normal. All my girly things were hidden in the garage, where she would never check. It felt kinky knowing that Opa loves me the same way he loves her.

Came Wednesday. I got a call from Opa at 11:30 right before lunch break.

"Hello Reese, it's me. I'm leaving the house soon. See you at 12?" he pretended it was his brother on the phone.

"I'll be waiting outside the gate." I replied quietly then hung up.

"Who was that?" my friend overheard and asked me.

"Oh, my host father is coming to pick me up at lunch. I'm taking the afternoon off to help him out with stuff." I replied.

"Lucky you!" he said.

"I sure am lucky!" I replied with a giggle.

I was waiting outside at 12 o'clock sharp. Opa arrived shortly. I got in and said, "Hey Opa. You're on time!"

"Hop in the back sweetie." he said. I climbed to the back and saw the white sundress with rose patterns he bought me. My wig, makeup, a red thong and heels were in a separate box also. "Get dressed sweetie. We have around 20 minutes before we reach the mall." he said as he looked at me through the rear-view mirror.

The car windows in the back were slightly tinted so I quickly stripped out of my school uniform and got dressed. "Did you forget the bra Opa?" I asked as I couldn't find it inside the box.

"No. I don't want you to wear one." he giggled.

"You naughty old man!" I smiled and replied.

I quickly put everything on and moved back to the front seat. Put on my seatbelt and pulled the mirror down from the sun visor to put on my makeup. The dress was short. So short that my thighs would show while sitting down. I would be lying if I said I did not like it. I am a flasher after all lol.

Opa put his left hand on my right thigh as he drove. Gently caressing it as I put on my makeup. I was quick this time as I didn't have time to make it fancy.

We stopped at an outlet carpark. It was far from our place.

We got out of the car and made our way into the mall. It wasn't packed on a Wednesday. Opa had his hands in his pockets as he walked, and I decided to cling my arms around his as if we were a couple going shopping. It felt right.

We stopped at Quiksilver first and went straight to the women's swimsuit section.

"Hey guys! I'm Natalie. Do you guys need any assistance?" one of the girl staff approached us.

"Hi there. We are just shopping for some swimsuits for my granddaughter here." Opa replied, "Can you show her around? I need to run to another store. Will be back to pay."

"Sure!" she replied.

"Pick out what you like sweetie, I'll be back in 15 minutes." Opa said to me and left.

I wondered where he was going.

"So! What sort of style are you looking for?" Natalie asked nicely.

"I'm not sure to be honest." I replied, "A bikini and a one piece maybe?"

She eyed me up and down and picked out a teal bikini. "I think this color really compliments your skin!" she said, "And this one!" she held up another burgundy one piece.

"They're so pretty!" I replied as she handed them to me, and I went to look in the mirror, "I'll take both!"

"Nice choice!" She said, "Anything else you want to try on?"

"Do you guys have denim shorts?" I asked.

"Of course!" she replied in a cheerful voice and turned around as she said, "You like this pair I'm wearing? They're on sale!"

They were very short and 1/3 of her butt was showing.

"Perfect!" I replied.

She measured my waist and picked out my size and led me to the changing room.

"Try them on! Give me a shout if you need anything." she smiled and said.

I quickly stripped out of my dress and put them on. They fit perfectly. I turned around to look in the mirror and saw half of my butt was showing through the jeans. I absolutely loved how I looked. I couldn't stop admiring the girl I became in the mirror.

"I guess I'll take them too!" I said as I came out of the dressing room.

"Perfect!" she smiled.

"I'll take a look around the store and wait for my grandpa." I said.

Opa returned with a small bag in his hands.

"All ready?" he asked me.

"Yeah! I'm done here Opa." I said as he walked over to the cashier and paid.

He came back with my clothes and as we walked out of the store I asked, "What do you have there, Opa?"

He pulled me to the side and opened the bag to show me. I was surprised with what I saw. Inside the bag were a new set of wigs, long and curled up blonde wigs, butt plug with a red heart shape in the end, a 6" dildo and a big bottle of lube. Finally, I saw a white piece of cloth and a small box in there. I didn't pay too much attention right then as I was too excited.

"You need to be ready for the weekend, right?" he smiled and said.

"Thank you Opa!" I jumped onto him out of excitement. Clinging on his neck with one leg curled up like a girl would.

"Now, remember we're outside." he hugged me back and said, "Let's keep going."

Next, we went to the pharmacy. "Can we get some sunscreen for my granddaughter here?" Opa said to one of the staffs and turned to me, "Go and pick out a perfume you like."

I rushed to the perfume section and started to test out everything. I picked one that smelled of roses and handed it to Opa at the counter.

"Now two more stops." he said.

We walked in the dollar shop, and he picked some tattoo stickers. There were small hearts and roses and one big tramp stamp sticker. I knew where he was going with this.

Final stop was at the shoe store. He asked the staff to show us the wedge heels. I tried on a few and picked a pair of 4" cork wedge sandals. I've always loved showing my feet and toes.

It was 2pm by the time we got back in the car. Before entering I asked, "What's the white cloth and box in the bag for Opa?"

He smiled and took out those 2 items from the bag and handed them to me as he got in the car.

"Open it up!" he said while laughing.

I held up the white cloth first and I put them down immediately. "Oh my gosh!" I gasped. It was a mankini. The one Borat made famous in the future, which we didn't know at the time. I went on and opened the small box. There were small metal rings in them and a tiny key.

"What are these for Opa?" I questioned.

He laughed loudly and said, "I'll show you later."

It was a 40-minute drive home. I had plenty of time to remove my makeup and put everything away in the car. We got home close to 3pm. We put everything in the trunk except for the white box, which I put in my school backpack.

"You're home early today!" Oma said as she welcomed us home.

"Yeah, school finished at 2:30 today. Opa picked me up!" I replied.

Opa swiftly got everything ready for dinner and put them on the stove. He asked Oma to keep an eye on the things and came in the study to ask if I wanted to go for a walk in the woods with him.

"Bring the small box with you." he whispered.

We made our way to the woods. It became cloudy and it was obvious we were the only ones on the tracks. We walked for about 10 minutes while chatting jokingly slapping each other's butts. I pulled out the white box from my shorts pocket and handed it to Opa. "Will you tell me what this is for Opa? Why did you ask me to bring it?" I asked.

Opa pulled me off the tracks and we were in the woods surrounded by trees and bushes.

"Take off your pants sweetie." he said, "I'll show you what it's for."

I took my shorts and briefs off and Opa kneeled down in front of me.

I watched as he put my clitty and balls through one metal ring and a put another small metal cage with some holes on my clitty head pushing it towards my body and finally securing both pieces with a lock. My clitty was locked!

He stood back up and said, "This is a chastity sweetie. To make you a girl you need to stay small. Now you need to learn to cum without touching your clitty."

My mind was blown. This is some next level training.

Opa pushed me against the tree and started kissing me passionately. I answered by opening up my mouth to receive his tongue and wrapped my arms around him.

We kissed for about 3 minutes, and I reached down and felt he has made a tent down there. I started unbuckling his belt and jeans and pulled down everything as I kneeled in front of him. His cock was in my face. I started stroking it and smelling it to tease him. It's been a long day of walking, and the smell of his cock was stronger than ever. This turned me on so much.

I began sucking him and playing with his balls. I got super horny and started to feel my cock being locked in place and I wasn't able to get hard at all!

Opa gently put his hands on my head and guided my movement. I opened up wide and went as deep as I could until I felt a gag. I pulled back and coughed while Opa laughed, "Go easy now." he said.

I continued to suck him until he pulled me in and shoved his cock to the tip of my throat. He let out a big moan and came. I felt his cock pulsing on my tongue as he shoots his cum directly down my throat. It made me so happy knowing that he needed and wanted me. He slowly pulled out as I sucked the last drops of cum from his mouth and savored it in my mouth. We have made our mark here in the woods. This later became a usual thing for us. This was our spot. We even carved our initials on a big rock nearby in a heart shape. T and S. It was something very special.

I kept the chastity on me from that day and learned to pee like a girl would. It didn't take me long to get used to.

The week flew by, and I got home fully excited for the weekend to come. Opa noticed and teased me in front of Oma, "Someone is excited for the yacht cruise." he said.

"It will be fun! Wish I was young again." Oma giggled.

"It will be so much fun!" I replied and gave Opa a subtle wink.

*End of part 6*

*Part 7 coming soon*