A story of a teenage boy with desires to become feminine. He gets busted wearing his best friend’s, sister’s cheerleading uniform. And she always wanted a sister...

A boy in a girl’s cheerleader outfit was staring back at me. My hair was long, but just not, well, styled like a girl. I opened her drawers and found some tie-backs and barrettes. I had no clue of what to do with them. Just then, I heard a soft knock on the door.

“Brian, is that you in there?” It was Britney!

“I’ll be right out,” I whispered.

“Brian, you have been in there for a half hour! What is going on?”

I had to think fast. I told her that I was sick. She did not believe me. I heard her try the door. Then I heard her use a tool to unlock the door. It was opening! I threw my body against the door and pushed.

“Please don’t come in Britney!” I pleaded. It was too late. She was part of the way in pushing back on the door when she saw my reflection in the mirror. Her eyes got big.

 
 

From Brian to Brianna
By Angela Renee Rineheart
 
CAUTION! Explicit Sex Scenes Contained Within!

 
My very first recollection of an orgasm came while squeezing my legs together while climbing a pole in third grade. Even though I did not understand what was happening to me, I knew that I loved the feeling and wanted it again and again. So it began, that the way I could derive sexual pleasure, had very little to do with stroking my penis, and everything to do with manipulating my lower region without using my hands.

As I reached puberty, the masturbation was very frequent and I soiled many pairs of underwear just by fantasizing about a pretty girl, and the lovely things that she would wear. There was no need to even touch myself. All I had to do was think of beautiful clothing, and I would ejaculate into my underwear. I had a hard time getting a girlfriend, but longed to be close to girls. So, I started getting interested in the next best thing. I had access to soft, feminine things through my mother, and sister’s clothing. I was deathly afraid of getting caught, so I did not get into their things until later. The first time I can remember actually putting on something that felt remotely feminine was when my father bought me sanitary socks for my baseball uniform. I can remember the soft, thin material against my leg. They went really high, almost over my knee. As I looked down at my feet, I thought that if nobody really knew, they could be mistaken for girl’s feet and legs. This thought excited me. I would wear them every chance I got. Little did I know that this was just the beginning of an obsession that would stay with me forever.

By the time I turned 15, I became bold and looked for excuses to stay home whenever the family would leave. As the time approached for all family members to be out of the house, my heart would start to race. My mother and sister both had huge dressers full of underwear and pantyhose. They also had lots of pretty dresses in their closets just waiting patiently for me. I would always start with pantyhose. By the time I got the sandals and dress on, I would usually have to run to the bathroom because I could not hold back ejaculating. After a while, I became better at holding back, so I could take the fantasy further before making a mess. As time went on, I became even bolder. The laundry hamper was my heavenly getaway. Not only at home, but at neighbors while babysitting. I became well known as a willing babysitter in the neighborhood, which opened up quite a few opportunities to enter the laundry hampers of many young mothers (Some with absolutely wonderful lingerie). It became like a drug to me. The more I dressed, the more I masturbated, which in turn lead to my wanting to dress more often. As I dressed, I found myself looking in the mirror and not being happy with seeing a boy dressed in girl’s clothes. I wanted to see a girl staring back at me in the mirror. I started thinking about putting on makeup.

I can recall spending the night at my best friend, Mark’s house on Friday nights in the winter time. I would spend most of my summer days at his house playing ping pong all day. His home was my home away from home. Mark and I were not what you would consider “typical friends.” He was over 6 feet tall, muscular from working out with the football team. I, on the other hand was a lot shorter at 5’5”, and slim. Had we not met at age seven, we might not have ever become friends. Somehow, we always found many things in common and did not let our “popularity status” affect our friendship. Mark had girls lining up to date him. I, on the other hand was his “cute little friend” that no one really wanted to date. “You’re too good of a friend”, was the line I always got from girls when I asked them out. (Whatever)

He had a sister named Britney. She was a vision. She was everything I fantasized about looking like. She was 17, a cheerleader, prom queen, and had a wardrobe to die for. She was one of those girls that could be mistaken for a snobby little princess, but nothing could be further from the truth. She had everything she could ask for, but seemed very down to earth. I fantasized often about getting into HER laundry hamper. Unfortunately, Britney’s room was upstairs and Mark’s was downstairs, so when I had to use the restroom, I would probably be questioned if I used the upstairs bathroom. It was getting to be about 10:30PM and Mark and I were just watching the end of a movie on TV. There was a scene involving a drag queen. I became a little restless in my chair. She was beautiful and I found myself hypnotized and dreaming that I could be that cute if I just had some help and applied myself. Mark must have noticed because he woke me out of my trance.

“Brian! Hey buddy, didn’t you hear me?”

“Huh?” was all I could say.

Mark looked at me really strange and said,

“Dude, that’s not a real girl you know.”

“You could have fooled me.” I blurted out.

We then had a short conversation about how women have such a different way of looking at things than men do.

“Wouldn’t it be cool to have a girlfriend with a thought process and interests like a guy?” I felt my lower region stir as that comment came out of Mark’s mouth.

I looked at him and smiled. “Well, she is probably out there, don’t you think?”

Mark returned my smile and for a second, I felt him look me up and down before responding. “Is she?”

I felt my face get red. At that moment, the front door was opened. It was Britney. Her boyfriend just dropped her off after the football game. She was still wearing her cheerleader uniform. I could hear her walk down the stairs. She entered the room in which we were sitting. I must have still been beet red.

“What have you been up to, Brian?”

Once again, “Huh?” was all I could get out as I drooled over her beauty.

“Have you lost weight, Brian? You look so skinny! Are you eating Ok?” Britney always seemed to kind of like me. Not like as a boyfriend, but she always seemed to be kind of looking out for me.

“Let me look at you. Please stand up. She smiled and seemed genuinely concerned. Little did she know that I had secretly been taking all natural hormones for about two months. My breasts had become very tender and I had FELT a lot softer, but did not think it was that noticeable.

“Your face looks nice”, and then she hesitated and walked closer. “Are you wearing makeup?”

I was mortified! I experimented with my sister’s mascara, but that was two days ago and I had washed it off! Did I get it all off?

“No way, what are you talking about, Britney?” I did my best to play it off, but she could tell that I was uncomfortable.

She gave me a big smiled and turned to walk away. “I’m sorry Brian. It almost looks like you might make a better Brianna, than Brian. It’s just an observation. I’m going to take a shower and go to bed.”

I did not even have a chance to respond and she was gone. “What was that all about?’ I asked Mark trying to hide my excitement of her observation.

“Well, don’t take this the wrong way Bri, but Britney has a point. You have been losing a lot of weight lately. You don’t look unhealthy…just kinda... well, ya know….uh, feminine?

I just stared at him. This was my chance to confide my secret desires to a friend. “Well….Mark, uh….I guess….I just….uh.”

I chickened out.

“You guys are seeing things! Are we going to sneak that bottle of wine in here or not?”

He seemed to snap out of his daze and said. “Oh yea, it’s in the car. I’ll go get it."

Mark snuck out to the car and came back in the front door after getting two wine glasses from the kitchen. He seemed really excited as he poured the wine. “Cheers to you, Brianna!” he whispered while half laughing.

“Knock it off, Mark.” I whispered back, half smiling. Mark and I polished off the whole bottle and were very sleepy. Mark drank three quarters of the bottle, easily. Maybe even more, so he was getting ready to doze off. He looked up at me as he put his head back on his pillow. He was clearly drunk. He looked me up and down, smiled and whispered, “You know, Brianna, you might want to try a little makeup and some lipsti……….zzzzzzzzzzzz.

This might be my opportunity, I thought. As Mark was dozing off, my heart started pounding. He started to snore and I was headed upstairs tiptoeing and being as quiet as possible. I was so excited that I walked down the hall shaking my hips like a sexy girl. I quietly opened the door to Britney’s bathroom. As I closed the door, I switched on the light and took a deep breath. It smelled of Britney’s perfume. My heart felt like it was going to come out of my chest. I locked the door and turned toward the laundry hamper. I opened it and it squeaked. “Damn!’ I whispered. Then I saw it. It was right on top of the pile. Britney’s cheerleading uniform. I just stared at it.

“What am I doing?” I said to myself. “C’mon Brianna, when are you going to get another chance like this?” I reached in and grabbed the pile. It was cold that night, so she had worn suntan pantyhose underneath her skirt. She had also worn her mock turtleneck body liner under her shell top. It was a complete uniform and I was about to try it on! I quickly disrobed and got completely naked. I needed to get the pantyhose on first. I rolled up my socks in a ball in order to make some nice fake boobies to place under her sports bra. I sat on the toilet and rolled the pantyhose and slid them up my leg. They smelled heavenly! I could feel my whole body tingle. As I pulled the hose over my member, I almost came, but managed to hold back. My feet looked cute and I pointed my toes. The baby blue bloomers hugged my butt perfectly. It felt like it was molding my bottom into a female shape. The sports bra was next, and then the skirt. I was able to zip it up! The diet has paid off! Britney’s skirt actually fit me! It was soooo cute and short. It had pleats. I twirled, but did not want to look in the mirror until after the body liner and shell was in place. The body liner was baby blue and fit like a second skin. It clung to my arms and torso like it was meant to be there. God! This just felt so good…so right!

I LOVED feeling like a girl! After pulling the shell top on, I looked in the mirror.

Shit! A boy in a girl’s cheerleader outfit was staring back at me. My hair was long, but just not, well, styled like a girl. I opened her drawers and found some tie-backs and barrettes. I had no clue of what to do with them. Just then, I heard a soft knock on the door.

“Brian, is that you in there?” It was Britney!

“I’ll be right out,” I whispered.

“Brian, you have been in there for a half hour! What is going on?”

I had to think fast. I told her that I was sick. She did not believe me. I heard her try the door. Then I heard her use a tool to unlock the door. It was opening! I threw my body against the door and pushed.

“Please don’t come in Britney!” I pleaded. It was too late. She was part of the way in pushing back on the door when she saw my reflection in the mirror. Her eyes got big.

“I knew it! Brianna, LISTEN!” She suddenly got stern. “If you do not let me in, I will tell the whole school about you wanting to be a cheerleader.”

I let up on pushing the door shut. I stood there, mortified, head down.

“I am so sorry, Britney.” Please let me close the door so I can take your uniform off. This is really embarrassing.”

She looked me up and down, smiled and said, ‘It fits, doesn’t it?” I just nodded.

“Come into my room, Brianna. I want to show you a few things. Oh and don’t change, ok?”

I just did as I was told. Walking down the hall, I was aware of the silky pantyhose rubbing against my legs. I couldn’t help myself, and starting slightly shaking my hips. Britney entered her room, and asked me to shut the door. Her room was everything I had imagined it would be: lots of pink things….extremely feminine. She picked up her vanity chair, and placed it in front of me. She asked me to sit in it and sat on the bed opposite me.

“You have nice legs, Brianna.”

“Please stop teasing me”, I pleaded.

Britney just smiled. “Do you not remember the conversation we had about two hours ago? I really meant what I said. You…Brian… Brianna, whatever name you wish to be referred to, can pass as a pretty girl. You just need some assistance. NOW, do you want to be a girl?”

I looked down at my nylon clad feet.

“Why are you doing this?” I asked.

She smiled again and replied. “Well, Brianna…oh, may I call you Brianna?”

I looked up and half smiled, then, nodded.

“Great. Ok Brianna, I have three brothers and love them all. But I have always longed for a sister. My current crop of friends, well yeah, they could kind of be my sister’s, but….well...they are so caught up in bullshit. You, on the other hand, well, you could be my, my...well, my project!”

Her smile and eyes got real wide.”Brianna, will you allow me to transform you into my sister?”

I tried to hide my excitement. After all, I was still very embarrassed. I never imagined anyone ACCEPTING my secret! I mustered as much courage as I could find inside of myself and asked her, “Do you really think that I could look like a real girl?”

As she smiled and nodded, I was already asking my next question. Before long, we were chatting quietly just like two girls at a slumber party. Britney encouraged me to act and move like a girl while talking. It all seemed to come so natural for me. She showed me how to sit properly with knees closed, and the right way to cross my legs. She sat me at the vanity mirror and showed me how to use clips in my hair to style it more feminine.

It was nearly 3:00 when she said, “Listen, if you get caught in here, we will both be in a ton of trouble. So why don’t you get back downstairs and get some sleep. We will talk more tomorrow, ok? Oh, and by the way, here you go.” Her outstretched arm was holding a pink satin camisole and panties. “Would you like to sleep in this tonight?”

I smiled and threw my arms around her. “How can I ever repay you, Britney?”

She kissed me on the cheek and said, “I will think of something, little sister.” Then she grabbed her perfume bottle and gave me a little spritz on the neck.

I took the pretty camisole and panties and headed back to her bathroom. I really did not want to change out of the uniform, but knowing that I could sleep in a pink camisole was a wonderful alternative. I snuck back downstairs to Mark’s room.

Mark was snoring in his queen size bed. I normally slept on the floor in my sleeping bag. I slipped into the panties and cami. Oh it felt soooo right, but I was COLD! I watched him sleeping peacefully as I stood there, barefoot. I wandered what it would be like to be held like a girl. I tiptoed over to his bed and knelt down beside him so my face was right next to his.

“Mark”, I whispered. I was really taking a chance, here. What if he wakes up and freaks out? He did not open his eyes, but answered me.

“What is it?”

“I am cold.”

“So get a blanket.”

“I don’t know where they are.”

He opened his eyes slightly, rubbed them and started to tell me where to find them, when he realized what he was looking at.

“What are you wearing?”

“It’s your sister’s PJ’s,” I answered, attempting to strike a sexy pose.

He looked at me up and down. It was dark. I wondered what my silhouette looked like in the dark. Mark opened the covers as if to say, “Come on in.”

I lay down next to him. We laid there silently for about 30 seconds, but seemed like minutes. Mark finally whispered. “What in the hell are you doing?”

“I’m cooooooold……” I purred.

He put his arm around my shoulders and held me. I could feel my lower region stirring. It felt as if I was getting wet inside my panties. I put my hand on his stomach, and laid my head on his hairy chest.

“You smell nice Brianna.” He whispered again. Then he did something I never imagined. He got up on his arms and hovered over me. His breathe smelled of wine. He lay down on top of me, and moved his lips towards mine. He then kissed me full on. I kissed back. He opened his mouth and moved his tongue towards mine and I welcomed it with enthusiasm. I was a boy, dressed as a girl, kissing another boy, fantasizing about being the girl of his dreams. I could feel his cock pressing against my stomach. It was huge and I wanted to feel it in my mouth. I wanted to please him orally. I whispered in his ear, “Oh Mark, I want to suck your cock.”

It all seemed to come so naturally. I reached down and grabbed hold of his cock. It was stiff, but soft. I caressed it with both hands as he kissed my neck. He got off of me and turned on his back. I lay on top of him and got an up close look at his huge member. I opened my mouth and closed it lust around the head. I had secret fantasies about doing this and looked it up on the internet. There was a complete clinical “how to” on a website. I studied it and had a real good idea of what to do. I was prepared to please my man!

I first concentrated on the mushroom head. I licked and teased it. I flicked his pee-hole with my tongue. He moaned. It just seemed to be a natural instinct. Thinking about the instructions, and wanting to maximize his pleasure, and satisfy my natural craving, I proceeded to lick all along the shaft, exploring all its shape, thickness, soft skin paying particular attention to the underside of his head. I was really getting excited and wanted to take more into my mouth, particularly because Mark had his hands roaming all over my butt and legs. I read about how to deep throat, and wanted to attempt it. I relaxed the back of my throat and opened my mouth wide. As I lowered my head, I could feel his penis head touch the back of my throat. My natural reaction was to gag, but I closed my eyes and relaxed my throat even more. As my man’s cock entered my throat, I closed my lips around the base of his cock, and tried to swallow. (Just like my one-a-day vitamins. Then I slid my lips up and down his shaft. The only way I could describe this experience was…….I felt incredibly feminine. It was as if I was a real girl pleasing my man. I squeezed my legs together and my semen erupted in my panties. I continued sucking for all I was worth.

Mark moaned loudly and out of nowhere, he said, “Brianna, I am going to cum!” He actually did not complete the sentence before erupting a load of warm semen in my mouth. I continued to swallow. I instinctively knew that I would enjoy swallowing his cum. He was shuddering with pleasure, and for some reason, my panties were soaking wet, but not entirely from my own semen. My anus was dripping. It was as if my anus was behaving like a woman’s vagina, ready for sex! My thoughts raced towards the idea of being penetrated. How is that done? Does it hurt? I want it!

I rolled off of him and quickly snuggled up onto his chest again. A man was holding me after having oral sex!

“WOW!” he whispered. “You should have been born a woman. From now on, I am going to call you Brianna! Is that OK with you?”

I snuggled up to his neck. “But, I am a guy, Mark.”

“I can’t wait to see you in makeup. I just KNOW you are going to make a very pretty girl. You can’t stop now Bree! In your heart, you know you are a girl!”

Bree. I liked that that nickname. I smiled and fell asleep to his steady breathing in his arms.

The sun shone brightly in my eyes the next morning and woke me up. I was still in Mark’s arms and feeling like a glazed doughnut. (Very sticky, but yummy!) I slid out of bed and quickly got to the bathroom down the hall in order to change back into my boys clothes. I could hear the rest of the family upstairs chatting quietly and preparing breakfast. I decided to take a shower. I noticed a razor in the shower stall and decided that it would be fun to try and shave my legs. I was motivated to move forward in my transformation. I went from being deathly afraid about someone catching me and not accepting my behavior, to seriously considering stopping my path to becoming a man, and getting on the fast track to womanhood! WOW, the more I thought about it, the more I wanted to do this right. I was going to take a hot bath and shave my legs the way the models did in the shaving cream commercials! I stripped naked and started the bath. There was a knock at the door.

“Brianna!” It was Britney. “Honey, my parents just left to go Christmas shopping. Open the door!” I put a towel around my waist and opened the door. She was standing there smiling. “Any regrets?”

I smiled back. “No way!”

“Good! Would you like to take a bath in MY bathroom? I have lots of perfumed bath oil beads and if you are interested, I can give you a quick lesson in shaving your legs and armpits. Whatcha think girly girl?”

I followed her upstairs. As we passed Mark’s room, I snuck a peek. He was still snoring.

Britney grabbed my hand. “C’mon little sissy, I have lots of plans for you today. We only have about an hour to get you ready for the inspection.”

“What inspection are you speaking of?” I inquired.

“Well, after getting back in bed last night, I started thinking of all of the things a teenage girl needs. You need a ton, Brianna! So I made a short list of my most trusted friends. I called two of them this morning. You know Katie, and Kimber, right? Well, I asked them if they had any stuff that they no longer used to donate to a project I was involved with.” “You told them about me?”

“Not exactly, Bree-Bree. Now don’t go getting your panties in a bunch. I want you to strip, relax, and get in your bubble bath. Once you get in, close the shower curtain and call me in, OK? I have some specific things that I would like you to do.” She gave me a peck on the cheek, looked me in the eyes, and hugged me. “You are going to LOVE your experience as a girl! We have it made. We have all the power ya know?” She closed the door after exiting the bathroom.

I had really gone past the point of no return. How was I going to break this to my parents? How were people going to react at school? The tub was being filled with perfumed water. It was intoxicating. I noticed that Britney left a pink, satin robe on top of the laundry hamper. I forgot about all my concerns. It was as if the excitement I felt completely over rode any concerns. The tub was full. I got in. It was hot! I lowered my body in slowly and got used to the water.

My GOD, it smelled so good! I grabbed the body wash. It had a Victoria Secret’s label on it. I starting getting all soaped up. I wanted that delicious, feminine smell all over my body. I closed the curtain and called to Britney.

She poked her head in the door, phone in hand, and whispered with her hand cupped over the receiver, “Be there in one minute, doll. Use the salon shampoo. After you rinse, put some cream rinse in and let it sit. Then spread the Lady Edge shaving foam over your legs.”

I did as instructed, heart pounding, shaking with excitement. With each little nuance of a feminine experience, I became more and more convinced that it was my destiny to be female. The cream rinse was another breathtakingly, feminine smell. I pulled it through my hair just like the commercials. My legs had very little hair to begin with, but getting them hairless and silky, was something I wanted to experience again and again. I heard Britney say goodbye to whomever she was speaking with and she opened the door.

“OK, Bree, how do you feel about what has happened so far?”

“It’s like a dream come true, Britney, but I am a little concerned about your friends getting involved.”

“Funny you should bring that up. I was just speaking to Katie from down the street. She is on her way over.” My eyes got big and I began to protest, but she put her hand up and smiled. “Now Bree, Bree, did you really think you were going to keep this a secret? Last night, you told me that you wanted to be a girl. Today, you told me that you have no regrets. Trust me, Katie will not only be cool with this, she is willing to help.”

“You already told her?” I squealed.

“RELAX, cutie pie! Don’t you trust your big sister?” I nodded slowly. “It looks like you are already on your way. I see you have gotten silky smooth. Isn’t it just the best thing? Now let’s rinse your hair and get it into a towel. I want you to get used to patting yourself dry, just like a girl. I put some body powder on the counter. After you are completely dry, powder puff your entire body, get your robe on, and meet me in my room. I want you to sit with me at my vanity mirror."

The powder puff experience was one of the most sensual two minutes of my life! I puffed every single inch of my body with a perfumed powder. It seemed to make me even softer than ever. Once I felt how smooth my butt, legs, and lower region was, I completely lost it and had to clean up with some tissues. As I walked into Britney’s room, I lusted over the way my legs felt rubbing against one another. I sat daintily at her vanity, making sure to smooth the silky robe under my bottom, crossed my legs like Britney showed me the night before, and looked at myself in the mirror. Britney was sitting on the bed behind me.

“What do you see in the mirror, Bree?”

“Um, a guy dressed like a girl?”

“Would you like to know what I see?”

I nodded.

“I see a teenage girl that has yet to realize her full potential. Now, put your right foot up here on my bed. I am going to show you how to paint your toenails.” I just did as I was told. My entire lower region tingled as she applied the pale pink polish.

The next twenty minutes included lessons in walking in heels, female mannerisms, flirting with boys, AND the beginning of a lifelong passion. Britney gave me my first makeup lesson.

“Katie will be here shortly, and I want to use her foundation, cuz I think it will match your skin tone perfectly. OK?”
Just as she was saying that, there was a knock at the door.

“I’ll get it!” It was Mark calling upstairs.

“Is Mark up?” I said startled. Britney laughed at the absurd question. “UUUH, I am pretty sure he is, Bree. What’s wrong?”

I blushed. “What if he sees me like this?”

“What would you like to do, stay in my room all day?”

“No, it’s just that…well…we're not done yet.”

Britney put her hands on her hips and tried to suppress a giggle. “Do you like my brother?” I just looked at her. “You do! Oh my, well do not worry. There is no way that he sees you until we have completed the transformation, alright?” As I was nodding, Katie entered the room. She had a big box with her.

“Hi Brit, and...Brian? Is that you?”

I gave a weak smile and nodded.

“Hey, it’s cool with me~! Quite frankly, I can’t imagine why more guys don’t want to be girls. It’s the best life I can imagine! Welcome, so should I call you Brianna?”

“Yes, yes, yes," Britney interrupted. "It’s Brianna, or Bree-Bree. Did you bring the foundation?”

Katie then proceeded to empty the box onto Britney’s hope chest. Apparently, Britney asked Katie to bring any clothing, and makeup she no longer wore. There were panties and bra sets, pajamas, prom gowns, dresses, low rise jeans, tank tops with built in bras, cute sweaters, skirts, earrings, makeup, hair clips, curling iron, hair straightener, perfume, body spray, body sparkle, all kinds of shoes. She even brought last year’s cheer leader uniform! I reached over and picked it up.

Britney giggled. “Oh she likes being a cheer leader, don’t you Brianna?”

Again, all I could do was smile and nod. I looked at Katie and thanked her for bringing it.

Britney picked up the foundation and powder compact. She held it up next to my face. “Oh girly girl, this is YOUR COLOR ! By the time I get this on you, your skin will look like porcelain. Now pay attention, because you need to learn the subtle nuances of not only becoming a pretty girl, but the constant maintenance is very important. Understood little sissy? Now repeat after me. Oh yes, yes! Please teach me, big sister, Britney.”

I looked at her kind of funny. “Do you really want me to say that?”

Both girls put hands on hips and looked down at me. They scowled. “Damn it, Bree!” Britney was almost whining, “How can we be girls when you will not cooperate?”

“Britney, I am so sorry. I want to talk like a girl, but I, I, I ….guess I have to practice.”

Katie spoke up. “I have an idea. He is still too male. He needs to lose his penis!”

“What!!??” I screeched.

“No, no, no, honey. I mean hide it. Do you remember that show on HBO about transgendered people? I once saw a guy hide his penis inside his testicles. He kept them there all night comfortably. He, or she, said it made her feel more like a woman. Have you ever tried that, Brianna?”

I looked down at the floor a little embarrassed. “I saw the same show. I tried it that night and really liked it. I even slept that way all night. I just need a tight pair of panties.”

“Now you’re talking, Bree-Bree. What color panties would you prefer? Never mind. I know it’s pink. Now go to the bathroom and do your stuff. No wait! Can we watch?”

My first reaction was to say no, but I struck my best femme pose and said, “As long as it’s just between us girls!”
Both girls laughed. Britney opened her top drawer and pulled out a sexy pair of pink panties. I had actually gotten quite good at hiding my package. The girls were amazed!

“Are you feeling more feminine now, Bree?”

I crossed my legs and replied in the most feminine voice I could find.

“Oh yes, yes! Please teach me, big sister, Britney. Teach me how to wear makeup so I can live life as a pretty girl!”
Both girls were grinning from ear to ear. “Let’s make a girl!”

I watched in awe in front of the vanity mirror as they proceeded to apply the foundation: first a creamy substance, then the powder. It all blended together magically. Then the color, oh my what colors! By the time they had applied blush, eye liner, eye shadow, I was shuddering with delight. The girls were really enjoying it too. I asked if I could apply the mascara and lipstick, as they were something I enjoyed most, AND had a little experience with. They were happy to let me, but I was shaking so much, Britney had to step in. The lipstick was a pretty pink.

“This might hurt a little”, said Katie. “It has a formula that makes your lips kind of puffy. It’s like collagen, but milder. You’re going to feel like you have about one hundred needles poking your lips, OK?”

I took the tube from her and glided it on my lips, just like in the sexy commercials. It hurt!....and I loved it! My face was now female. For the first time ever, I looked like a pretty girl! I smiled from ear to ear at my reflection.

“Wow Bree. You are a very pretty girl with a dazzling smile!” The girls were amazed. “The boys are not going to be able to take their eyes off of you!”

I couldn’t even tell which girl was talking to me. I was in a daze.

“Boys! Where is Mark?” I exclaimed.

“I will go check downstairs”, said Britney.

Katie looked at me. “Do you like boys, Bree?”

I blushed. “Well, I feel more like a girl when I fantasize about being with a boy.”

“Just wait until you’ve been kissed!” We both giggled.

Britney came back in the room. “Mark is watching TV downstairs. He thought Brian was up here eating breakfast this whole time. I told him that he is not allowed to see his buddy until we were done transforming him into Brianna."

My eyes got big. “What did he say?”

Britney scrunched up her nose and smiled. “Well, BRIANNA, he said that he could not wait to meet the new girl in town! Watch think about that?”

“I think we ought to start curling my hair!” We all giggled again.

I was amazed at how quickly they were able to brush style my hair. By using clips, they made it into a real girl’s style. “Bree, we simply MUST get you to the salon.” Britney said. “Your hair needs a feminine style. We can make it cute, but if you really want it done right, I can set you up with Tami. She works at the beauty college and she owes me a favor.”

My head was spinning, and my crotch was tingling again. A salon visit? I took a good look at my face in the mirror as they brushed, combed, and curled. I was really noticing the differences. My eyebrows were much thinner, and arched. My lips looked much fuller, and my cheekbones higher thanks to the blush. I realized that even without makeup, my face could easily pass for the fairer sex.

Britney picked up her cell phone. “Tami? Hi sweetie! Can you fit in a favor for me today? You can! Awesome! Thank you so much. Uuumm, there is something you should know…….” She left the room, and continued to talk in a hushed tone. Oh well, one more person will know about Brianna. Hmmmmm.

It came time to choose my clothes for the day. Being in complete girl-mode, I wanted to show off my legs and wear a sun dress. The girls decided that I needed more practice in heels before going out in public wearing a dress, so we compromised and chose some cute, tight fitting, low rise, pink jeans, and a tight sweater that showed off my belly button. Katie supplied some cute, pink flats that had a bow on the front. I chose some bangles for my wrists, and a cute necklace with a heart shaped pink pendant. I struck a pose in Britney’s full length mirrored closet doors. My God, I thought. I am soooo cute, and I smell so good, and I-I,I want to live like this forever!

Britney came back into the room. “We are all set. We have a 1:00 appointment at the beauty school. You will get a cut, style, and nail tips. After that, we will head to the mall to get your ears pierced. Oh, Bree, you look so cute. I am so happy for you!”

Mark called upstairs. “Hey, Britney. It’s been long enough. Is she ready? I have to get to work!”

“It’s time to get a boy’s opinion, Bree. Are you feeling good about the new you?”

I nodded as I took another peek in the mirror.

Mark’s mouth dropped open. My heart was pounding so hard, I thought it was going to leap through my chest.

“Whoa! Will you do me the honor of letting me escort you to the school dance?”

I looked at the girls. They were giggling, and grinning. “Well?” they harmonized in unison, "Dating is the best part about being a girl!”

I looked back at Mark and he went down on one knee, and grabbed my hand. “Brianna, in my eyes, you are a very pretty girl. I would be proud to have you on my arm at the dance.”

I was blushing, and felt so much like a girl. “Of course I will, Mark! We ARE best friends, right?”

He smiled. “Great! I have to get to work. You girls have fun today.”

Both girls gave me huge hugs. It was amazing to me how quickly I was accepted as a girl. Had I known it would be this easy, I would have taken these steps a long time ago. The visit to the salon was better than any fantasy I had ever had, and I have had many, many fantasies about a makeover. Tami made only one mention of my gender. It was when we first walked in. She told me that had she not known, she might not have even questioned my being a girl. It made me feel so good. I looked through several picture books of cute “girl” hair styles before deciding on three different styles.

She cut it a little shorter than I wanted, but explained that she wanted to shape my face properly. She also gave me blonde highlights. Everyone was amazed at the transformation. I barely had time to admire Tami’s work, when I was whisked off to the mall. I wanted to shop for clothes, but the girls said we were there for one reason, and that was to get my ears pierced. Both girls worked in the mall and told me that I had to find a way home. “We will drop off your clothes later Bree! I will call you, OK?”

My house was only a few blocks from the mall, so normally, that would have not been such a big deal. Walking home as Brianna was another story. “Well, I may as well get used to it,” I said with a sigh.

The walk home was pretty uneventful, although I did get two whistles from guys in cars.

Mom and Dad were out of town, so I immediately logged on to the computer. I had a hidden favorite site about sex, and I had some questions about anal sex. The site had lots of great advice. I learned that my anus is very flexible and with practice, I would eventually enjoy penetration after becoming more flexible. I had no idea that the anus should be cleaned out entirely. I started thinking about my sister’s douche. I was very interested in that when I happen to come across it while rummaging through her cabinets one day.

After looking it up on the internet, it helped me understand a woman’s need to feel fresh and clean during her menstrual cycle. I wanted a menstrual cycle. I decided to start a shopping list. It would include several enemas, a douche, anal lube, and a vibrator. I was getting wet just thinking about it. I had some money, but not a lot. I just had to have these items. I got a blank stare from the lady at the drug store when I asked if they carried vibrators. I did not care. I was on a mission!

When I got home, I immediately stripped and got into my favorite teddy. I then followed the instructions on the enema box. I was surprised how easily the bottle slid into my anus with the anal lubrication. I gave myself two enemas. It was yucky, but necessary. I felt very lightweight. I borrowed some dusting powder from my sister, powdered my bottom and shaved scrotum. Then I positioned myself at the foot of my bed, and proceeded to liberally line my anal sphincter with the water based slippery solution. One finger was easy to get in. Even two was not too difficult. I started tugging in order to stretch it out, just like the instructions I read online.

Before long, my feet were pointed towards the ceiling, and I had both hands tugging at my bunghole. Both index and middle fingers were stretching my hole. After a few minutes of being uncomfortable, I decided to try my sister’s vibrator. I found it a while ago in her panty drawer, and hoped it was still there. I had a fleeting feeling of guilt that did not last long. I told myself that I would thoroughly clean it up and she would never know the difference. I found it exactly where it was before. It was big, easily 8 inches long and thick! I put my head back and turned it on.

I pressed the head against my hole and started whispering to myself to enhance my little private fantasy. I was fantasizing that I had a real pussy and I was in bed with Mark. “Mark, put your cock inside of me. I want to feel your cock moving inside of my pussy. Please gently push that beautiful rod inside of me and take me as your woman!”

I could feel myself start to loosen up, the more I spoke. I added more lubrication around and inside my hole. I pushed the penis head inside and tightened up. I started to talk myself through it, remembering the instructions that the key to good anal sex is to RELAX.

I started over and slathered lubrication up and down the big, plastic penis. I sat up and looked at it. I placed the head in my mouth and sucked it a little. The real thing tastes better. I chuckled at that thought. “OK, Mark, I want you to make love to me”, I said out loud. I took a deep breath and laid back again, After getting totally relaxed, I made another attempt, this time pushing back on the head as if I were trying to push out a stool. It went in fairly easily. I moved it back and forth. It was sliding in and out of me nicely, but to my surprise, I was not getting any sexual gratification out of it. It just felt as if I was going potty without the poop!

I kept up with the fantasy, and continued my dialog. “Put it deep inside of me Mark! I want you to cum inside of me and get me pregnant. Tell me that you love me. Tell me how much you love to be inside of me!” Wow, where did THAT comment come from? I was starting to tingle as I went deeper, and stroked faster. As I pulled the penis out, it felt less like I was pushing out a stool, and more like a sensual act. I was beginning to like it! I wanted it deeper; I wanted it to be a real penis. I wanted to be a woman! I was really beginning to buck and push against it, and I could feel it intruding me even deeper. I felt as if it was less of an intrusion, and more of a warm, welcomed friend. Now THIS is more of what I had hoped for!

I heard the front door open. “Helloooooo!”

It was my sister, Cindy! I tightened up, and the penis came sliding out. My legs squeezed together and I came.
Shit, she was headed upstairs!

“Brian? Are you here?”

I quickly ran to the door and locked it. “I am in my room, Cindy.”

“Open up! I have to show you my new dress!”

“Um, can you show me later?”

“Now, Brian! When have you ever hesitated to see one of my new outfits?”

She was right. I was always enthusiastic to see Cindy’s new clothing for my own personal reasons.

“Cindy, you need to know that I have made some changes since yesterday.”

“BRIANNA! The news is out, honey. After your appearances at the salon and the mall, the whole school will know by Monday.”

I closed my eyes, and answered her quietly. “Let me get dressed, Cindy. I will be right out.”

As I peeled off the teddy and slipped back into my pink jeans, I started realizing something. My whole life is going to change for the better. I do not have to hide my secret from anyone any longer. The funny thing is, as I looked in my mirror and recalled my conversations with Britney, and Mark Saturday night, I think most everyone already knew of my desires.

I opened the door and Cindy was leaning against the wall. “Hi sis! My, you ARE cute! Where did you get the cute outfit?…and what’s your new name?”

I told her about Britney and Katie’s generosity with the clothing they no longer wear. “Oh yes. I heard that a few other girls are planning on helping you too. So I guess I won’t have to worry about you stealing any of MY clothes anymore?”

I blushed. “Cindy, I am so sorry! By the way... I like the name, Brianna.”

“Don’t sweat it, Brianna. Mom and I were trying to pick the right time to ask you about it. Now we don’t have to.” She smiled. “By the way, I called mom on her cell. She knows, and is happy for you!”

I started crying and gave Cindy a big hug. “You are pretty good at being a girl already!” We both laughed.

I then felt compelled to be honest about stealing her vibrator. She was a little upset, but admitted that she was looking to buy a new one anyway, and now BRIANNA can buy it for her! I was happy to agree.
 

Britney & Brianna