My bros story by Crazzy via Misterpolls

This story happened two years ago when I was 17. I had waist length light brown hair, green eyes and an average looking body. My 15-year-old brother was the same height as me but not the same body shape for the simple reason I am a girl and he wasn't

I had my 5 closest friends round for a slumber party, Becky (17), Mary (17), Alison (15), Laura(16) and felicity (flick)(15). (the ages are how old they were at the time). It was around midnight and we were watching a film that Laura had brought round, cant remember what it was now. And we got into this conversation

  • "Your brother sure looks like a girl, facial features I mean".
  • ME "Yes I know we got him to dress as a girl for Halloween one year, I took pics for blackmail"
  • F: "What did you do with the pics?"
  • ME: "I never used them for blackmail, they are here somewhere"
  • Ã: "Oh, lets see them
  • ME: "Alright"

I search and quickly found the pictures and showed them to the other girls. We had managed to make him look like a real girl alright, even buying a corset and everything just so that he would have more of a female figure.

  • Me: I think we still have the corset around here somewhere, I could dig it out I suppose.
  • Meh, there's no point, let's just watch the film.

And that would have been all that happened that night if certain things happened about half an hour later. It started when I heard a creak outside my door and we crept up to it and opened it suddenly, finding my bro was sitting listening at the door.

  • Me: You perv! Right, come in here right now.

He slowly entered my room looking sheepish, and I guided him over to my bed and had him sit down. "You were listening at the door, spying on us, We'll need to do something to punish you. I still have that picture of you I took of you from last Halloween, I'm calling in the Blackmail and we're going to give you a makeover right here and now".

  • Bro: "You mean your going to dress me as a girl? No, please, come on, I'm sorry I won't do it again".
  • Me: "No, that's it! We're going to turn you into my little sister".
  • A: "I don't think that's really fair, let's at least give him a chance to get out of this".
  • B: "Like what?"
  • A: "Well, how about a bet? He's always bragging about how much better he is at playing Playstation games compared to everyone else. Him ans Laura should have a tournament. If he wins, well I know he has a crush on me so if he wins i'll french him and perform a strip show for him but only to my underpants. However if he wins then he has to allow all of us to dress up up as a girl with a corset (to give him a figure), and put on everything else, and He has to ware it for the rest of the night."
  • Bro: "And if I refuse"
  • A: "Then we just dress you up the same anyway, it's your choice. At least this way you have a fighting chance"
  • Bro: "Alright, I accept, but how about we make it double. If I win you have to french me anytime that I ask you for the next two year. You also have to strip naked anytime I want when were not in public, strip completly naked."
  • A: "No way! Not unless you also agree that if we win, you have to agree if anything that I come up with".
  • Bro: "Well, what sort of stuff will you be making me do if I win?"
  • A: "No, first you have to agree. If you agree then I get to come up with anything I want you to do, a part from public nudity. If you agree then there is no going back and you'll just have to do it.
  • Bro: "Alright then, I agree.
  • ME: "I'm going to go and get Mom to witness this agreement because I don't really trust you to stick to it if you loose.

I then walked out of my bedroom to find my Mon who was elsewhere in the house. I found her downstairs and told her about the bet and what the terns two parties had agreed to so far. She said to give her 25 minutes and she'd come through to see us. When she did come upstairs she had a document which she got him and Alison to sign. She then took Alison out of the room and got her to tell her what she would have my brother do. She laughed when she heard Alison's terms and said she thought it was a good idea and that she would be back in another 25 minutes.

Mum came back and said "Since I'm a lawyer, I know about these kind of contracts, now the signing of this document by Alison and Sam is a legally binding agreement which ill outline what will happen. Now if you are serious about doing this Sam you must sign this"

Him took the document and signed it without even reading it. If he had bothered to read it, he wouldn't have signed it at all. After Alison signed this second document as well she asked my Mom to read out the terms if you won the bet.

"Ah, ok then. I've told you time and time again Sam to always read things before you sign. This document is legally binding until you turn 18, at which point you will be a adult, because I've already given my full permission as your legal guardian. Why? Because I've always wanted you to be nicer to woman and now you will be."

Mom continued "The terms of bet are outlined that during the game tournament you may only play with one hand, Laura may use both. If you win then Alison will have to comply to the conditions you set, but because she felt sorry she agreed that if you win she will also be your completely willing slave for two weeks."

"However now we come to what happens if you were to loose. You have to become a girl for the duration of this contract which is until you become 17. You will have to do whatever your sister and her friends decide, her friends being the one present tonight. I've called your school principal just now, I know its late but she didn't mind, and she will allow you to attend the school as a girl for the next two years, with you wearing the full girls uniform. But the worst clause in this document for you is that I, as your legal guardian, have decided that if you were to sign this document, you would be started on a course of hormone treatment that will turn you into a girl."

"If you behave yourself over the next 9 months till your 16th then I may consider not allowing a hormonal treatment. As part of the document you have given permission for the girls to glue breast forms onto your chest using a glue which will last for a full year before needing to be replaced, what this means is that the breasts will remain fixed till 3 months after your 16th, if the hormones have started then they will not need replaced, but if I have shown mercy, then they will be, meaning that they will be their till 3 months after your 17th. You do however have the chance to challenge a week after your 16th. If the challenge ( the nature of which will be decided by me) is won by you then you will be freed and this will cease. If you lose however, the hormones will start regardless of my wishes

Wow, after she was finished we all sat there with out mouths hanging open in shock apart from Alison as it had all been her idea. The gaming tournament went ahead and guess what, he lost and we started getting him ready for his new life. We got the Corset out and told him that he had to wear it and that the only time he could take it off was for his Bath. We give him a padded bra to use until next week when we bought breast form and glued them on to him. When attending school he had wear: Black tights, a knee length black skirt, it cam to an inch above his knees when he sat. he had to where a white blouse and a red blazer, as well as the school tie. In the summer he had to where the same but instead of black tights he had to where white knee high socks. For both seasons he had to wear a pair of girls dress shoes with a 2 inch stiletto heel and a buckle.

What he was forced to wear outside of school was even more fun. He had a wear the following items at all times: White normal knickers and the corset and a bar. He had shoulder length black hair which we grew till it reached his waist like mine. He also had to wear makeup all the time. Outside of school he wore general stuff but for going out he wore: Knee high Black leather boots with 4 inch stiletto heels which zipped up. He wore red tights with that and a black leather skirt, 1 inch from his knees, and a red corset, fully working like his normal one but worn on the outside as a piece of clothing. With makeup and the long hair and the corset and the forms he looked like a girl. At the beginning he would always try to take any high heel shoes off when we weren't looking so we ended up buying him a pair with an ankle cuff at the top which locked with a padlock.

He ended up looking very attractive and we coached him on things like his his voice and his walk so if you didn't know that he was a boy you would never have guessed by looking at him. He got hit on when out, but we didn't make him go with a guy. We made him were a thing which would press his genitals against his body and kept them cold preventing him form getting an erection and making down there look right, he would were tight jeans sometimes and you wouldn't know.

Now its over though, mom never made him take the hormones, and he is now a guy again, well almost. Because of our evilness, we used a super super glue last time we glued his forms, it lasts three years so he will have them for another 2 years, also due to our strict tightening we used the corset to give him a permanent girly figure, we worked him on the workout machines in the gym In our house, my mom earns a lot and my dad left for another woman 5 years ago.

He now has a permanent girl figure, permanent girly legs and breasts for the next two years, he has decided that for the next two years rather than look silly he is going to be a girl. This is really for the next two years.Interestingly enough, it turned out that his feelings towards Alison were not unrequited, she quite liked him too.

Now they are together and getting on fine. We reckon that she gets off on the whole thing, and he is madly in love with her, I mean madly in love. She dominates him a lot just around and we think she does it more when they are together and we think his decision to stay a woman for the next two years was heavily influenced by her.

He has a whole new respect for woman, and although he didn't find the experience sexually exciting he thinks that in some ways it was good because he can see where it made him a better person. A lot of his so called friends abandoned him soon after it began, but he made new understanding friends soon after, he reckons now that he is better off without his old friends, and since all his new friends are girls I don't think he is complaining.