The Making of a Sissy Pt. 02

-recap-

Opa got a bulge watching me undress in front of him. This became our little secret.

*Part 2 starts here. *

A few weeks went past, and things continued as usual until my bed broke again out of the blue and this time the entire bed collapsed.

We were all in shock when this happened. Not again.

I snapped out of it and said, "It's okay I'll just sleep with Opa." I was really tired and just wanted to lay down and pass out.

We got into the master bedroom, only the small lamp was on. Opa opened his arms to hug me before bed, so I went in for a hug. He hugged me tighter as I hugged him back. Before letting go he gave me a small but quick grab on my butt and said, "Night-night."

It was the first time someone had ever grabbed my butt, but it didn't feel weird at all. In fact, I liked that feeling. So, I said goodnight back. He gave me a kiss on the cheek and we both went to bed.

Being 18 I was as horny as a horse during mating season. I often jerked off and wiped them with my pajamas and let them dry out before leaving the study. I never really thought much of it and never thought someone would find out. Sometimes when I feel adventurous, I would jerk off in the other rooms during the day.

One day I was jerking off in the garage thinking they would be busy baking and watching TV. I was fantasying about Opa fucking me, even though I've never seen him naked let alone his cock. Suddenly the side door of the garage sprung open and there was Opa staring at me. I had one hand on my cock and the other on my butt with my middle finger fondling my boy-pussy. He quickly closed the door behind him.

"Don't stop now. I saw you from the window and thought I'd come in and join you." he said jokingly.

I quickly pulled my pants up and said, "You weren't supposed to see me like this." with a huge blush on my face. I could feel the bloody rushing to my head as I was embarrassed.

"It's ok. I was young once too. I understand." he said calmly "But why was your hand on your bottom?"

"Uh I don't know. Don't worry about it." I quickly replied.

"Well, the cake is ready when you are! Come in. I'll make you a milo." he said while opening the garage door and gesturing me to go over. As I walked past him, he grabbed my butt again, only this time with more passion. I jumped a little and quickly went inside.

That night as we got in bed, I was still thinking about what happened so I kept turning and couldn't sleep. Opa noticed and turned to me and whispered, "Can't sleep?"

"No." I replied in a whisper.

*The reason to us whispering is due to their habit of sleeping with the doors of the rooms open when they sleep, and we didn't want Oma to hear our conversation. *

"What's on your mind kid?" He asked.

I turned around facing him "I don't know. I'm just really curious." I said.

"About what?" he asked again. I could see his face as the moonlight lit up part of the room.

"Everything." I said.

"That is hard to understand. Try to be specific kiddo." he said.

"I don't know if I like men or women or both. I mean I like girls but sometimes I think about guys. I even think about dressing as a girl." I said while covering my face with the blanket "I've never seen a man cum in real life before."

"Oh?" He said with a surprised expression "Do you want to see a man cum?"

"I mean yeah why not. I've never seen it in person. Only online." I replied.

He looked over to the door and turned back and said, "I can show you if you like?"

I was shocked but happy at the same time as soon as I heard him. Unsure but curiosity got the best of me.

"Rea...really? You show me?" I asked shyly.

"Yeah, it wouldn't hurt to show you. I don't even remember the last time I came so why not." he replied while smiling.

I sat up as he took his pajama pants off. I could somewhat see the shape of his cock in the moonlight, and it was big. It was only semi hard but as he kept stroking it became fully erect. It's about 6" and boy was it THICK. I consider myself to have a big dick for an Asian at 6" but it only half as thick as his!

I leaned in as I wanted to see clearly. His breathing became heavy as he jerked off in front of me. My heart was racing, and I could feel myself becoming wet from all that's happening. I was SO TURNED ON, but I kept my cool.

His hands started moving faster and faster and finally he whispered "oh...oh..." as his body tensed up. I knew he was going to cum. Right in front of me!

"I'm....Cuming!" he said. I got ready and had my eyes wide open as I didn't want to miss the first time seeing a man cum in real life.

White streams started to shoot out of his thick cock. Load after load after load onto his body. It felt like it wouldn't end! His body relaxed as his cock spits out the last load. He quickly grabbed a handkerchief and wiped everything down.

We both lay down afterwards.

"How was it?" he asked.

"I don't know. different?" I replied.

"Haha that's good. Now hopefully you can get a good night's sleep kiddo." he said as he reached out to my head and pulled it towards him to kiss me on the forehead.

I was shy. The feeling was different. Before he turned to the other side he whispered.

"I know you've been wiping cum with your pajamas. I see them in the laundry you know." with a cheeky smile on his face.

I was shocked.

The next day we pretended like nothing happened and got on with our day.

The bed wasn't going to be fixed anytime soon so I got used to sleeping with Opa. However, nothing happened after that night. We only talked in bed before falling asleep. Sometimes we'd have conversations about my curiosity, and I confessed to him that I would get in Oma's clothes and stockings while they're away for church on Sundays.

"So do you want to be a girl?" he asked one night as we got into bed.

"Sometimes. When I'm horny I guess." I replied.

"Very interesting. Why don't you show me next time?" he replied.

"When?" I asked.

"Oma is having a small surgery next weekend. We are going to be alone." he said.

"Oh, for her spine? Or foot?" I asked.

"Foot. She's been feeling pain lately and the doctors will look into it as she must stay at the hospital." he replied.

"Okay. We'll see!" I replied with a bit of joy, but I tried to hide it.

During the week I did some research on how to become a girl for a beginner. I shaved off the very little hair from my legs and armpits. I looked in the mirror and saw my pubic hair and thought to myself "Fuck it." and shaved it off too.

I have never felt so smooth in my life. I felt girly and tender. This is when I started to enjoy shaving myself all over.

Friday came. Opa and Oma were about to leave for the hospital when I got home. I hugged her and said "It's going to be fine. Love you." before they headed out.

As soon as the car left the driveway I quickly stripped out of my clothes and went for a shower. I then went into Oma's drawers navigating through her bras, underwear and stockings. I chose the white lace bra and underwear set and a pair skin tone stocking. I then took the white nail polish she had lying around and put them on my finger and toenails.

I'm experienced in putting on bras and tucking my cock back and hold it together with the panties. The feeling of the stockings on my skin was nothing I've ever felt before now that I'm fully shaven. I felt so sexy.

Next, I went into the closet and looked for an outfit. I picked out a white top with flower prints over it and dark brown knee-high skirt. Wearing a skirt for the first time felt weird but kinky. The only thing missing was a wig and makeup, but I didn't have time to do makeup and there was no wig in the house.

I stood in front of the mirror after dressing up. I looked fully passable as a girl except for the makeup and wig so I was a little conscious at the same time.

1 hour later I heard the car pull up to the driveway. I hid in the small room and looked out the window. Opa was back with Chinese takeaway in his hands.

"I'm home! Guess what's for dinner?" He said as he entered the front door.

"Where are you? Are you okay?" he said as I did not reply to him the first time.

"I'm in here. But I'm nervous." I finally replied.

"Why are you nervous? Come on, the food is going to get cold! It was a long drive." he said as he started putting dishes on the table.

"Promise you won't laugh if I come out?" I asked with a shaking voice.

"Are you okay? What happened?" he answered in a worried voice.

"Yeah, I'm okay. You promise?" I asked again.

"Of course! Don't worry kiddo." he replied.

I took a deep breath and slowly walked out of the small room into the kitchen.

He watched me as I crossed the hallway. His eyes sparked with a big grin on his face.

"You look beautiful sweetie." he said gently.

"Really? I don't have a wig or makeup. I don't look like a girl." I replied with my head down.

"Yes! You look amazing in that." He said as he walked towards me to hold my hands "I swear it."

"Thank you... I hope you like it?" I said quietly.

"I love it!" He said loudly "Now come on let's have dinner."

We sat down and began eating. He opened a bottle of wine, and we drank as we ate. We chatted and he complemented me throughout dinner and that made me feel comfortable dressed like this and gave me a bit of confidence.

As we finished dinner and 2 glasses of wine later, I started to feel a little tipsy.

"The show is coming on soon. Why don't we move to the living room and watch it together?" he said while holding my hand leading me to the couch.

He sat me down and went back to grab our wine. I was tipsy and thought this was the perfect opportunity to spice things up. I took off my top and skirt and sat there with nothing but my underwear and stockings on. Even though the panties were white it was kind of obvious that I was soaking wet down there.

He dimmed the lights as he came back with our wine. After putting the wine down, he turned around and saw that I was in lingerie.

"Wow." he said "You look amazing sweetie!"

"Thank you." I replied "I have an idea. Why don't you join me in your underwear?"

"Is that what you want sweetie?" he asked.

I nodded shyly. "Anything for my girl." he said as he went back to his room, and I could hear his belt hit the floor. Soon he was back, and I was amazed with what I saw.

He was well built with a medium sized belly, just the way I like it, and on top of all that he was hairy. He wore white briefs that day. I could see his bulge getting bigger the longer he looked at me.

"I guess we matched colors today." I giggled.

"Sure did!" he said as he sat down next to me.

"So, what should I call you sweetie?" he looked at me and asked.

"Call me Charlene, Opa" I replied as I placed my right hand on his left thigh. I saw a twitch in his briefs as I touched him.

"Ok Charlene, you look absolutely beautiful tonight. This is the best night I've had in a long time." he replied "And oh you should call me daddy."

"Okay Da... daddy."

*End of part 2*