My Brothers Little Problem

by

A Happy Wife

 

When I was eighteen my father remarried. I just loved my new stepmother and was glad that dad had found someone. In a short time Martha had changed my father from a rough and tumble typical macho dad into a kind and sweet gentleman. I thought the change was best for all concerned. He had lost his beer gut, had improved his posture and had become very respectful of women.

Martha had him cleaning the house, cooking meals and doing personal tasks for her and I. My father had even offered to shine my shoes and boots for me. Well it was really Martha who had offered his services but he didn’t refuse. He did look a little embarrassed about it, but when Martha said "Eliot, ask her if you can take care of her shoe wardrobe." He asked and once a week he checks to see what needs care. He polishes and cleans any shoes that need it, cleans the soles and powders the insides. What’s really cute is the little apron he wears when he is working at home.

My little brother Mike really has a problem with Martha. He hates her and thinks she is turning Dad into a sissy. I tried to tell him that her and Dad’s marriage is their business and not his, but he won’t listen and just will not be nice to her. I have told him to be careful around her "she isn’t going to take your crap Mikey". He just laughs it off.

Mikey is just fourteen and a bit of a brat. Our mother and I both spoiled him. He is used to getting his way and has always been able to manipulate the women around him. Martha is different she seems to be able to run the men in any direction she wishes. I had the feeling my father had already learned this and eventually Mike would also.

I was eighteen and lived at home but as an adult I pretty much can come and go as I please. My father had objected to my freedom but Martha told him "She is a young woman, and as a woman in this house she will do as she pleases!" I couldn’t believe it when my father said "yes ma’am" So I was free to stay at my boyfriend’s house on the weekends, and often did. I was in college and was working part time so I wasn’t home all that much.

I was just leaving one Friday night when I heard Mikey and my stepmother really going at it in the kitchen. Martha had assigned Mike some task that he thought was beneath his worth and they were discussing it. I could see that Mikey was going to lose this argument. I just waved by-by to them and left. My weekend didn’t go well I had a fight with my boyfriend and returned home Saturday afternoon.

When I walked in I was surprised to see my father and stepmother talking to a girl of about twelve. She sat next to Martha on the couch. My father sat in a straight chair across from Martha and the girl. The young girl was dressed in a pink party type dress she was nervously crossing and uncrossing her pretty little ankles. My eyes were drawn to her white ankle socks with the pink trim, on her feet were a pair of black patent Mary Janes. She sat with her hands folded in her lap her head was bowed down as if she was looking intently at her hands. She never even looked at me when I walked in.

"And who is this charming little thing?" I said. Martha smiled and said, "This little cutie is your younger brother." "Oh my GOD" I said, "It is him, oh he is adorable. How did you do it?" Martha said it was easy and it was the best way to train an unruly male. Then she said "It has worked wonders on your father." I looked over at my father and he was busy looking at his folded hands also. Then I noticed that my dad was wearing what looked to be a pair of ladies pant boots and judging by the cut of his pants ladies slacks.

"Stand up dad" I said. And my father dutifully stood. He kept his eyes down, as I looked him over. I fingered the zipper on the side of his slacks, felt the fabric of his almost a shirt blouse and traced the line of his bra across his back. I heard his intake of breath as my hand felt the smooth panty line of his posterior. "Nice" I said. "Now you Mikey stand up sweetie pie." Sweetie pie stood and he too kept his eyes down, must be a guy thing. I took Mike’s hand and pulled him to the room’s center. I stepped back and just looked.

The dress was the focal point. It was pink with white ruffled trim. It was as feminine as a nursing mother. The puffed sleeves were short with a ruffled edge. The hem was well above the knee and the stiff white petticoats stood almost straight out. I reached out and felt the boys leg, "Oh Mikey, you shave your legs." "That’s so sweet". He blushed from; I swear his legs to his ears. Martha had styled his boyish hair into a mostly feminine style a large pink ribbon was pinned to the upper side of his pretty head. He wore soft make up and was about as humiliated as a boy could be. I turned to Martha and asked her if I could borrow the new girl for a while. She said, "Of course dear, enjoy her." I turned and started up the stairs to my room. I looked back at Mike and said "get my bag dear and follow me."

Mike seemed glad to get out of the living room and the dominating presence of his stepmother. In my room he broke down, "you’ve gotta help me sis." I said "your smart mouth got you into this fix my pretty one. You had better keep it shut or GOD knows what she will do next." Now lets talk. "You better face it girl, you are going to be in dresses for a while. The best deal for you is to get to dress your age. You really are quite pretty and dressed like an early teen you will be a very pretty young girl. Dressed like you are, well you are a very pretty sissy." He sobbed and said "But I can’t dress like a girl. What will my friends say?" "What will they say when they see the outfit you have on now?" I asked. He just shook his head and sobbed quietly. Now listen Mikey, "you look really cute this way, and I like the why you behave much better than you did when you wore pants." "If you behave like a nice little girl maybe you can be in clothing that suites your age." "I will talk to Martha if you promise to be a sweet girl, if not then, well I guess you know what will happen when your friends see you." "Here you can read this copy of Cosmo, we can get you some Teen Beat or Seventeen later, when we go shopping." "Shopping?" was all he said. "Now Mikey, let’s teach you how to do girl." "Stand up sweet heart, oh that is so precious, you are just the most darling little sissy ever." "Ok girl, walk for me, walk in front of the mirror." "Watch me, hold your hands down, keep your upper body straight, take shorter steps." "The main thing is to remember your are a young lady now, carry yourself as one." "You practice for a while and I will go and talk to Martha."

I got downstairs to find my father at Martha’s feet. He had a very complete pedicure kit out and was in the process of doing a spa pedicure on her. "Ooh that looks yummy," I said. "Maybe your foot girl could do me later?" I asked. "Of course dear" was Martha’s response. I sat next to her and brought up the subject of Mike. "Martha I have convinced Mike that you intend to keep him dressed like a girl child and send him to school in a party dress." "I also convinced him that it would be best for him to dress as a girl his own age, since he will be staying as a girl." A big smile crossed over Martha’s face. "You devil you." She said. "I was only going to embarrass him a little over the weekend."

"Well we can’t pass up this opportunity to help the boy become a better person." "Can we?" "I will need to take him shopping." I said. Martha said, "use your fathers credit card." "Get the new girl everything she needs." Oh and dear keep her in the party dress for the shopping trip." It will help her remember to behave."

It was a very contrite little girl that made the trip to the mall that day. Mikey was the picture of embarrassment as we walked to the car. He sat quietly and sobbed gently as I drove the car through town and eventually the mall. Mike hesitated getting out of the car. I held the door for him and handed him his little black patent purse. I almost couldn’t go through with it when I saw the look of terror in his eyes.

The mall was filled with teenagers I knew Mike must know many of them and that he was in abject terror of being seen. Mikey’s little shoes made a darling little girlish click clack as he walked along. I know that the feminine sound must have been horror to his ears. I remembered how much I loved the sound of my shoes when I was a little girl. I smiled at the thought of my bratty little brother hearing his hard little heels screaming "sissy" in his ears. He moved over to my side in an effort to not be seen by the group of girls hanging out in front of a shop called Rave.

Rave seemed to be just the kind of shop the new Mikey should check out, so I guided the thoroughly humiliated boy into the confines of this bastion of teen-age femininity. We heard it at the same time, "Mikey?" "Oh my God, it is you." I turned to see a grinning pair of teen-age girls. "What gives Mike?" "Did you lose a bet or something?" Before Mike had a chance to make up a story I said, "Mike is being punished, and will have to spend a few weeks, maybe even months as a girl." "She needs a new wardrobe, do you think you girls could help us shop?" "She will need panties, bras, skirts, shoes and make up for a girl her age." The two teen girls were just jumping at the chance to add to the humiliation of Mikey.

By know we had drawn the attention of a couple of sales clerks and two more girls who were being filled in on Mikey’s plight. It seems Mike had a reputation as being a hellion around the girls at school, the group of girls thought Mikey’s punishment was fitting his crimes just fine. I gave one of the girls the credit card and said "Have fun." "I am going for coffee and I need some shoes myself." "Meet me at the makeup counter over at Macys when she is all fixed up."

I found a darling pair of flats for myself and was on my second Latte when Mikey and his new best girlfriends showed up. Mikey no longer had on the pink dress. He did have on a pink short all outfit with a white tee under it. The tee was all girl though with dainty lace at the neck and sleeves. He still wore his Mary Jane's and ankle socks and carried his little girl’s purse. The finial indignity was the pink ribbon Martha had pinned in his boyish hair. The girls carried bags and bags of things from Rave, Wet Seal and Forever Young all the new miss needed now was make up and some shoes. Macys had a great shoe store for a girl like Mike and I just knew that a nice sit down make over in full view of the store would be the ticket to remove the last vestiges of Mikes manhood.

"Did you girls find suitable underwear for her?" "Oh yes, in fact she is wearing her first bra and the clerk at Victoria’s Secret gave her something special." Mike was turning beet red. I leaned in real close and said "Tell me what she gave you sweet heart." "A ribbon" he said. One of the girls whispered in my ear and told me that the girl at Victoria’s Secret and tied a wide pink ribbon around Mikes penis and pulled it back between his legs, for a nice girly panty line. She showed me how the ends of the ribbon were just visible at the hem of his darling shorts. We took Mike to the make up counter and left him to the mercy of the make up consultant while the girls and I had a coffee and watched the crowd form around Mike and the make up girls.

With in thirty minutes Mike was finished and the girls and I could not believe the transformation that had taken place. Mike was lovely, he was no longer a boy even the girls who had teased him so much seemed to accept him as a girl. They hugged him and held his hand as we all went upstairs to the shoe shop. The girls had engaged him in the secret world of girl talk and their whispers and little girly asides were designed to include him. I knew Mike was aware of this change and that he realized he had crossed a line.

I watched as Mike and his new group of girlfriends squealed in delight at the adorable cross strap sandals Mike was trying on. I saw the disbelief in Mike’s eyes as he heard his own words "Sis can I wear them home, please." "Sure sweetie but we need to get you some nice school shoes too." The group of girls ran to the next display and I could see that my little brother was in a discussion with his friends about the merits of a pair of clunky-soled Mary Jane's as opposed to the burgundy loafers. "Honey get them both." "Oh sis you are the best." Mikey was now a girl and the enormity of his new situation was just beginning to hit home. My little sister had a problem.

A Happy Wife

 

 

 

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© 2002 by A Happy Wife. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.