Feminization of Little Bro Ch. 02

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Joe is caught, sister offers help.
2.2k words
4.5
58.1k
75

Part 2 of the 2 part series

Updated 06/10/2023
Created 05/02/2021
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Writie
Writie
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"Well well well, what do we have here?" I heard my sister's voice. I turned around and saw her standing in the open doors with phone in her hand.

"Please... it is not how it looks like..."

"I think it is exactly how it looks, you little pervert. It seems you liked it yesterday."

"Noo... I mean... we were drunk and quite excited from it. But I really don't know why I did it today..."

"You did it because you liked it... and the temptation was too strong. But don't worry, what kind of sister would I be to not help my little brother?"

"Help? What do you mean?"

"You will see... Now, take off the skirt immediately. "

So I did and stood in front of my sister only in her red top and black panties.

"Great, at least the skirt will not be full of cum now."

"Full of cum? What do you mean by that?"

"Well, you are going to masturbate for me, my little brother. Or should I say sister?" and she starts laughing.

"What? What are you talking about? Please, let me just change my clothes and we can talk about it..."

"Let me rephrase it... I caught you in my room with my clothes on and I have your picture... please, do as I told or I might accidentally send it to someone... or perhaps post it on Instagram..."

"No, stop... anything but that." and then I put my hand on penis and started masturbating.

"Not that hard! I don't want you to finish immediately, just stroke it slowly and nicely, so I can enjoy the look. Also, turn around and look at yourself in the mirror while doing it."

I just nodded, looked into the mirror and continued stroking just very very slowly.

Although I have never masturbated with anyone else looking at me, it felt amazing. Whole four inches of my penis were rock hard, bumping into the panties with its head.

I really started enjoying myself, when she suddenly grabbed my hand and took it off the penis. "Now listen, you have to decide - either you will immediately stop what you are doing, get off all my clothes and we will never talk about it again. And if I ever catch you again, this photo goes directly to Facebook, Instagram or anywhere else I want."

"Or you will continue and I will show you the kind of pleasures that you never even dream of. The kind of pleasure you can achieve only as a girl. As my little sister... "

I have just stood up there and didn't know what to do. Sure, we can just stop and never return back to it. But at the same time, this excitement and pleasure which was filling my body was irresistible. And if my sister is right, it can be even better. I mean, what can go wrong?

"Well... it might be weird, but i never felt so good like I am feeling right now. And I don't want it to stop..."

"It is not weird at all. And perhaps this is what you really are. And if you allow me to help you with exploration, you can find whether you really like it or not."

"Well, it might be worth a try. But please, if we do it... do you promise me to not tell anyone? Will this stay just between you and me?"

"Sure. As long as you want, it will be only between us."

"Do you promise?"

"Yes, I do."

After that, she took the phone and deleted the photo taken previously.

"See? I don't even have that picture anymore. Do you trust me now?"

"Th-thanks, I do. So, since we have a deal now, can I continue?" And I looked down to my penis.

"Ah, come on, you are so horny... actually, before that I have one thing which you need to know. You have to realize one thing - I might be pushing your boundaries, physically and also mentally. And some of that might be uncomfortable at first, but if you let me you will experience more pleasure than anytime you ever dream of in your life. And don't worry, I swear I will never do anything to hurt you. And also, you can say No anytime and if you do, I will consider that and maybe change the plans a little. But you have to be obedient of what I will tell you to do, otherwise you will never truly explore yourself."

All this sounds terrifying, but at the same time so exciting. I couldn't think straight from all that excitement and hornines going through my body - and all I wanted was to finish myself.

"Yes, yes, I agree. Please, will you let me finish myself now?"

"Of course", she smiled and let my hands go. I immediately put it in my panties and started masturbating again.

It took only a few strokes and I finished with an exploding orgasm. The cum was soaking through the panties and was flowing down on my legs. Before I even realized what just happened my sister took a big chunk of the cum on her fingers and stuck it to my mouth. "Now, swallow it."

Unable to speak, I just gave her a frightened look. She looked seriously. I remembered what she told me a few moments ago about pushing the boundaries. This has to be it... I slowly licked the cum out of her fingers and swallowed.

"Good boy. Now, go clean yourself and get some rest. We will continue later this evening."

I took a quick shower and changed the clothes. On the way to my room I noticed that my sister was gone again. I didn't think much about it and just went to my room. Here I was, just laying on bed, staring into ceilings and thinking about everything that just happened. It felt kinda weird, but at the same time really great and exciting. But why? I am not gay or anything, I like girls. So why was this so exciting to me? Maybe seeing myself as a cute girl was the trigger?

I didn't know that. But perhaps what will happen this evening will help to answer more of my questions.

I didn't even have a will to do anything except lay there. And as I did, I slowly started falling asleep.

"Wake up Joe! You slept the whole afternoon!"

I opened the eyes and saw my sister holding a bag full of some stuff.

"I was in the city and brought you something. We will use some of this stuff today and some of that later. Now please, get up and put yourself together. We have a lot of work in front of us."

I stood out of bed and stretched myself. "Alright, so what are we going to do now?"

"Well, for now, please take off your clothes and go to the bathroom. We have to prepare your feminine yourself."

"Really? I mean... last time we talked in a kinda pressure situation... what if we would just forget about the whole thing..."

"No, you promised something to me and so I did to you. Please, don't make me regret trusting you."

"Alright, you got the point..." I said and took off all the clothes. "Can you at least tell me what we are going to do?"

"Hmm, maybe some of that... We are going to shave all of your hair from nose to your feets. I mean, the few you have. And then I am going to give you nice makeup and clothes which I bought to you. Then we will see"

"Fine." and I went to the bathroom. She came there a few moments after me. I was standing in the shover, waiting for her. She took the rubber gloves and some sort of tube with cream.

"I will help you to get rid of those hairs with the depilation cream. It is painless and it would last you for quite a while." she said and starts spreading the cream across my body. While she was doing my pubes she gently touched my penis. It immediately twitched and got a little bigger.

"Somebody is really excited here." she laughed and continued. I didn't even have what to say. I felt a little bit embarrassed but at the same time it was nice to have someone taking such good care about me.

She had spreaded the cream anywhere where it was necessary and let it work for a moment. After a few moments she decided it was time to wipe it down and she showered me.

I looked really smooth after that. There were only a few small spots which she easily finished with a razor.

After the shaving, I was told to sit down on a tub and she started applying makeup on my face. This time she did it much more precisely and it took almost twice as much as yesterday.

"Don't you dare to look into the mirror, I will be right back with the clothes." She said and left the room. I wanted to see myself so bad, but at the same time I didn't want to disappoint my sister. So I rather just sat there and waited.

She came back in a few minutes and handed me nice lingerie panties, pushup bra and red dress.

As soon as I took the panties on my penis became rock hard.

Sho looked and it and said "I can see this makes you really excited. Now, please took the rest of the clothes"

I was struggling a little bit with the bra, but she helped me to put it on. Then I took the dresses and stood in front of my sister.

"Wow, you look really stunning."

"May I see it as well?"

"In a moment, let me just fix your hair... and that should be it. Please, come to my room, there is a bigger mirror to look into."

I followed her into the room.

"Please, don't look into the mirror yet, just close your eyes and stand up in front of it."

I did what she told me.

"Great, now you can open your eyes!"

So I did and I was stunned from what I saw there. It was not me who was standing into the mirror, it was some sort of sexy blonde girl, who looked like just someone who is prepared to go to the party.

There was nothing that would remind me of my real gender. Even my hard penis was well hidden by panties and the dresses.

"So what do you think? Do you like it?" she asked.

"This is really good. I would never have thought this is possible."

"That sounds like you like it." she said and smiled.

"Yes... it is really nice, thank you."

"You are very welcome. This was to really show you the potential, what you can achieve as a girl."

"And I think it worked well... but what are we going to do now?"

"Well, first of all, I would like to take a picture of you - and don't worry, we can use your phone. This picture will serve us later on, like some sort of reminder."

"Sure, if it would be on my phone only, then please take the picture. I have a phone in my room."

"Great, I will be right back."

As soon as she left I put my hand to my crotch and started slowly rubbing it, when still looking at myself in the mirror. It felt so amazin..."

"Ah, I am not behind you for a moment and you have to start with that again."

"No, sorry, it was just so natural."

"Yeah yeah, i know, it is hard for such a young and horny boy like yourself... you have to promise me to not masturbate without my permission."

"Uhh... I guess I will try."

"Very well. Now please, make some nice poses for me, I will take some pictures."

I have tried a few of those sexy poses which I saw girls doing on dating sites or their instagram pictures. After a few first awkward photos it started to be really fun. Sister encouraged me to do more sexy poses, with the dresses slightly raised to show my ass and panties.

After we took like thirty different photos she handed me phone and said: "Great, I think we are done for today. You can stay in dresses as long as you want or you can change to your normal clothes. But in any case, keep the panties on. Oh, and one more thing - while you will have any part of woman clothes I will be referring to as Joanna, so please get used to that."

"It's kinda weird, but that's the whole situation...so sure, you can." I said and took off the clothes.

"I think that would be it for the day. Please, keep the panties on and you can take rest of your normal clothes with that. And if you excuse me, I have some work things which I need to do right now."

"Sure", I said and took off all the clothes except for the panties and left the room. Before I closed the door I heard - "and remember - don't you dare to masturbate before I allow you to do so!"

Writie
Writie
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AnonymousAnonymous6 months ago

Darren, that's so sexy I'd love to be him

AnonymousAnonymousabout 1 year ago

Are you gonna continue this? Please?

dreamer31adreamer31aabout 1 year ago

i could wait to cum poor guy hurry up with part 3

AnonymousAnonymousover 1 year ago

And he went right into the bathroom and jacked off.

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