Feminization of Little Bro Ch. 01

It was one of those lazy days, when you don't even want to go out of bed. Also, it was a Friday and there are still six hours of online school between me and the weekend freedom. Not like there would be much else to do as I am stuck at home anyway because of that Covid pandemic. Well - at least I will be able to just lay down and watch some Netflix, I thought for myself and I got out of bed.

My first steps led to the bathroom, just to wash my face and brush my teeth. Once I got there and I was done with basic hygiene I looked into the mirror and noticed how messy my hair is. So I decide to comb them a little.

"Wow, I didn't even realize how long your hair is already." I heard my sister's voice behind me.

"Yeah, since the pandemic started and all the barbers and hairdressers got closed I didn't even have a chance to get them shortened."

"I am also kinda jealous of your nature blond... it's not brown like mine."

"Don't be.." I looked at her in the mirror and smiled "Your hair is nice too."

"Well, thank you" she told me and got one step closer to me and took the comb out of my hand. "I can see you are already done here... so if you excuse me, I would take the bathroom for myself."

"Sure thing." I told her and left..

When I was about to close the door she turned on me and said "Oh by the way, Mark called me and canceled our weekend. His brother needs help with moving or something... so I thought maybe we can get some drinks and just chill."

"Not a bad idea... we didn't have many opportunities for a talk, only like a few words every now and then."

"Exactly. So I will buy some wine and beers and be home around six."

"Perfect, so see ya in the evening." I told her and finally closed the door.

After that I just grabbed something to eat in the kitchen and went back to my room to connect to my online class.

Maybe it is a good time to introduce myself. My name is Joe and I am 19 years old, currently finishing last year in High school. My sister is six years older. We were a little bit distant as a children, since she was always picking on me. But I guess that's what older siblings do. Also, the fact she is higher than me makes it even worse.

She is currently working as an accountant and she also met her boyfriend there. His name is Mark and even when he is almost ten years older than her, he still seems to be a a cool guy.

We currently live alone in our family house, in a small town near London. Dad left us shortly after I was born so we were raised only by our mother. Few years back, she got a huge promotion as a manager in a large corporation and had to relocate to the United States. But she is making sure that I am doing okay, so she at least supports us with money every month.

The day went quite fast. I finished my school and then went for a short walk around the neighborhood. I was always enjoying those walks around, since I grew up like a little bit of a loner. Also, my only two friends from school lived at least thirty miles away, so I haven't seen them in a while.

After I finished my walk I went back home and cooked some lunch. Then I just watched Netflix for the rest of the afternoon, until my sister arrived. She bought some wine and beers for our evening. And with that, also a bottle of gin.

"So, let's start with a few shots... I need it after this horrible day in work."

"Sounds good, let's do it!" and with that, each of us finished three shots.

I grabbed one of the beers and sat on the sofa. She poured a glass of wine for herself and sit in the armchair in front of me. We talked for a few hours and it was really nice. She spoke about her job and how he is happy to be with Mark. I told her about the highschool and other things happening in my life, even though there was not much to talk about.

Suddenly she asked: "By the way, how about you and girls? Do you have any?"

"Well, you know how it is... it is hard to start dating someone in your current situation. I mean, I tried Tinder and other dating apps, but I am not very good at chatting and flirting there."

"Ah, I see." She smiled. "Speaking of that, I have another and quite personal question to you. Are you still a virgin?"

She caught me surprised. I always hated those questions. People around always bragged to have sex as soon as they could, some of them even before they could legally do that.. and yet, there was me who never even hold girls hand in his life...

"Ye..yeah, I am to be honest."

"Well, there is nothing to be ashamed of, you still have time. I was just curious. So, let's change the subject now..."

We kept talking and our conversation went more and more deep and intimate. She told me how much she love the mark and how she puts a big effort into making her looks as good as possible with all the makeup and sexy lingerie. Also she described how awesome is sex with Mark.

Also how I look good as well and I should not be worried to find someone to love as well one day.

Then she suddenly looked at me and said. "You know, all this talking is great and it is so nice to be fully open with you. But I am getting kinda bored."

"Well, we can turn on the playstation or Wii and play for a while, I am sure it will be fun.."

"No, that's not what I am talking about... I would like to try something else. You know.. don't take it wrong, but you look so nice and little bit of feminine with those long hair and literally no beard."

"What do you mean? Are you just making fun of me?"

"No no, not really... I would just like to try something. I wonder what you would look like with some makeup on your face. I am sure you would look nice with makeup as well.. maybe if you let me try it..."

"Wait, no, this is really not a good game to play... I don't want any makeup on my face."

"Come on, just to try it! Beside that, there is nobody around who would see you like that."

"I mean.. I guess you have the point. Well, alright, if you want to do it, suit yourself.. but don't expect anything from me. I will be just sitting here, drinking beer and you can do whatever you want."

"That's exactly what I wanted to hear... now wait there for a moment"

She went to her room for all that makeup stuff and then she started applying some of that to my face. It took just ten minutes before she stood and said "It is done."

"okay.. so let's check the damage." I laughed and grabbed a small mirror from the table and looked into it. And I must say that I was really surprised. With those longer hairs and well done make-up I really looked like a girl.

"Wow, this looks actually pretty nice.. but don't you dare to tell this anyone or to even take a photo!"

"I would never do that, you know that. It's just fun, between us. You can do some makeup to me as well if you want to"

"Hehe, don't ask me for that.. you would look terrible."

"I probably would." she laughed. "Maybe one day I will teach you how to do proper makeup as well." she said and finished her glass of wine. "Anyway, I am starving.. do you know if the local pizza place is still open?"

"Yes, they are doing delivery until midnight or so... feel free to call them. I can use some pizza as well."

She took her phone and did the order for us. As soon as she finished her call she looked at me. "They will be there in twenty minutes, so let's just wait."

Then we had one of those silent moments, both staring just to our phones, but then, after like fifteen minutes she suddenly said. "By the way, I have an offer for you."

"Uh.. offer? What kind of offer?"

"Well, since you already look so good.. I thought we could use that. What if I borrow you one of my dresses, and you would open the doors with them when pizza arrives?"

"Wait, nono, I disagree. Beside that, I am not really into crossdressing or any of this gay stuff and I dont really need anyone to see me like that."

"This doesnt mean you are gay. It is just some sort of game. Also, if you do that I would take care of all chores around the house for the next three weeks! Come on, it will be fun!"

"Hmm.. that sounds kinda good.. but still, I am not sure... I mean, alright, if you would take care of the house, then sure. But please, give me just your hoodie or tshirt, not the dress or anything."

"Deal!" She smiled and ran to her room to pick up some clothes. She has chosen a black t-shirt and one of her ripped skinny jeans. I had no problems putting them on, since I was even smaller and about the same wide as her.

As soon as I took the cloth on and adjusted them a little, the doorbell rang.

I went to them, took a deep breath and opened the door

There was a guy standing there, about the same age as me, but at least a few inches higher than me. I slowly walked to him with my head down and exchanged the paper bill for pizza, which he was holding and said silently "tha-thank you".

"You are welcome, beautiful. Enjoy the night." I looked at him and he gave me a little wink. I smiled a little and turned myself back to the door.

I immediately went through them and closed them behind me with a simple "Bye."

My sister was watching me all the time, holding back her laughter. Then she bursted. "Oh man, you were so shy and cute. And that guy had no idea."

"Yes, looks like I make a good girl, maybe even prettier than you." I smiled back at my sister.

"Hehe, I don't think so. But this was good, I haven't laughed that much in a while. Also, please, take off my clothes before eating this pizza... I don't want to have it dirty immediately.

"Sure." I changed clothes back to mine and we ate pizza. After another beer or two we have decided to call it a night. I just washed the remaining makeup from my face and fell asleep almost immediately.

Next day I woke up with a hangover. I experienced worse in my life, but still, the headache was killing me. I climbed out of the bed and went to the kitchen for some painkillers. On my way I noticed that my sister's room was open and she was nowhere around the house. They probably called her to work. This was not too uncommon as her department lost few people recently and she had to take care of quite a lot of stuff.

After I took the painkillers I have decided to take a bath. This usually helps me to get through this first hangover phase much more smoothly.

I have filled the tub with hot water and dived into it. My brain was trying to get through all the stuff we discussed with my sister yesterday. Overall, it was a really nice discussion between me and her. With the exception of that time, when my sister gave me makeup and her clothes. I still had that picture in my mind.

After I left the shower I noticed that there were my sister's panties laying on a shelf. She usually cleaned after herself, but maybe she was in a hurry and simply forgot them here after she took a shower.

And then I remembered that Last night I got the idea.

I ensured the doors were locked and I grabbed the panties from the shelf. They were black, barely covering the front. Rest was just made of the strings.

I have decided to give it a try and put them on. Surprisingly, they fit just perfectly to cover my penis, which starts growing immediately after the panties touch them. Since I was rather below average in size, they were covering the whole thing just fine even after I became erect.

I put my hand into them and started slowly stroking my penis. It would not be a problem for me to finish myself in a moment, but I have decided to stop.

Sister is not home, so maybe I can go to her room and try some other clothes as well. If she leaves for work, then it will take at least a few hours before she will be back...

And so I did. I went to her room and opened a big wardrobe where she had most of the clothes.I have noticed the red skirt and matching red top and since I was already really horny I put them on without thinking much about it and looked into the mirror and I was stunned. My body looked quite feminine by itself as I had wider hips than most of the guys and almost no body hair. And now, with those clothes on I looked really girly. With the same makeup like yesterday I would easily pass as a girl.

I put my hand in my panties and started masturbating. It felt amazing. I was almost about to cum but then suddenly I heard the noise, which made me freeze on spot. The noise, which phone is doing, while taking a photo.