The Making of SweaterTV Ch. 02

Thursday

I woke up when I heard the car door slam. I looked around and it was bright outside. I peered out the window and saw Mom pulling out of the driveway. I suddenly realized that it was after 12! I had slept for almost 16 hours and no one, Mom at least, woke me up. Maybe she tried and decided to just leave me alone.

I was now faced with a dilemma. I was home alone again. My mind began racing. Mom was working afternoons and I did not know how long she would be on that schedule. Sometimes, she would work two shifts and wouldn't be home until the sun came up. It was always changing. I knew that my brother would still be in school for at least two hours. That is unless he decided to cut the last few periods. But he never did that. He was Mr. Perfect. My still sore ass was telling me not to do it, but my erect penis had made up its mind. I slid out of bed and headed down the hall. I got to my sister's room and went in. I opened her underwear drawer and, instead of seeing an assortment of her bras and panties, there was an envelope with my name written on it. I stopped and starred at it. Should I open it or just leave it alone and go back to my room? How would he know that I saw it? I heard his voice in my head "When I tell you to do something, you'll do it". He would know. I don't know how, but he would. I reached for the envelope and opened it.

I knew you'd be reading this. I told Mom you were puking yesterday so she'd leave you alone. I hope you remember our conversation. You will NOT touch anything in this drawer or in the closet. Diana will be stopping by. You will NOT say anything about yesterday.

Diana was his girlfriend. She was gorgeous. If I really could have been a girl, I would want to look exactly like her. She was almost exactly my height with shiny black hair and clear blue eyes. She also had the most perfect body any one could ever want. And she was so sweet. She was always nice to me and went out of her way to say "Hi" whenever she was over. I wish I knew what she saw in my brother. But why would she be coming over? I began to worry and closed the drawer. I took the letter back to my room and stared at it while I lay on the bed.

At a quarter after one, the doorbell rang. It scared me and I jumped out of bed. I grabbed the note and stuffed it in the garbage pail under everything else and went to answer the door. As I opened it, Diana gave me the biggest smile and simply said "Hey." She was truly beautiful. And to make matters worse, she was wearing a tight fitting black and white turtleneck sweater. She walked in with a bag she was carrying. As she passed me, she grabbed my hand and said "Come on." and began pulling me toward my room. I hurriedly closed the door and allowed her to lead me down the hallway.

When we got to my room, she told me to sit on the bed. She pulled the chair from the desk, threw the clothes into the hamper and sat down in front of me. "Your brother told me about yesterday" she said.

My brain exploded! He told me not to say anything to her and here she is telling me she knows all about it! I starred at her. "It's OK. If you like doing it and it makes you feel better about yourself, you should do it." She had her hands on my knees and was looking directly into my eyes.

"Wh..wh..wha..what are you talking about?" I managed to say.

"He told me that when he and Dan came home, they found you dressed up like a girl, wearing your sister's bra and sweater."

"He did?" I began to feel the tears starting to collect.

She must have noticed. She smiled very sweetly and said "It's really OK. I mean, I know that Dan was a mean, but your brother said after he yelled at him, he apologized. It's nice the way he looks out for you. That's why he asked me to come by."

I was so confused. Dan apologized? My brother was looking out for me? I realized that he told her a story that made him look like he was my protector and not the details of what really happened. "So why did he ask you to come?" I asked.

She reached over for the bag she had brought. "He wanted me to help you." she answered. From the bag, she pulled out a chunky rainbow striped turtleneck sweater and held it up for me to see. "You like it?" she asked. I just smiled. She smiled back. She handed it to me and continued to pull more things from her bag. A pink bra and panties, a black mini-skirt, sheer black stockings and a pair of low heeled shoes each emerged in turn. I had never attempted to get more dressed than just a sweater and fake boobs. She must have noticed my excitement because she asked "Want to try them on?" All I could do was nod silently.

She helped me stand up and began pulling the sweatshirt over my head. I didn't resist. She began to push the waistband of my sweatpants down and stopped. "Do you want me to leave?" I shook my head. She pushed them down the rest of the way and I stepped out of them. I was now standing naked in front of her. My four inch erection proving how little of a boy I really was or would ever be. I realized she was looking at it and I began to turn red. I moved to cover it up, but she grabbed my hands.

"Don't be embarrassed. They come in all sizes. Just like breasts. Plenty of girls have bigger ones than me, but I love what I have. You should to."

I began to relax a bit. I started to speak and stopped short. "Go ahead" she said. "I won't tell anyone." Somehow, I knew she meant it.

"Well...sometimes I hate I even have it" I admitted.

"Why?" she asked. "Wait..." she continued. "Why do you get dressed up and wear your sister's underwear and sweaters? Why do you pretend to have breasts?" she questioned.

"Uh..." I managed.

"It is one of two reasons. Either you just like the way the sweaters feel and that is what gets you excited or you really wish that your were a girl and dressing up helps you believe that."

"Umm..." I replied. "A little of both"

"So you like the way they feel and when you are dressed you wish you were really a girl? Do you imagine you are with a boy or a girl when you get dressed?" she asked.

I looked at the floor. "Sometimes boys, sometimes girls" I whispered.

She lifted my chin and looked me in the face. "It's really OK. Remember, I won't tell anyone." She really was so sweet.

"Which do you like better?"

"I don't know."

"Have you ever been with another boy?" she continued.

I felt the blood rush to my face. How should I answer? She was being so nice, I couldn't lie to her. But my brother...What would he do if I told her?

Thankfully, she misread my embarrassment. "I understand. You're still a virgin. It will happen for you when you are ready and you feel that the time is right. What do you think about when you are with a girl?" she responded.

"Ummm..." I said slowly. "I usually look at a girl and think about if I was really a girl; would I want to look like her? I also.." My voice trailed off.

"Come on...tell me." she coaxed.

"I also imagine that she has a penis." I admitted. If this shocked her, she didn't show it.

What do you think about when you look at me? Do I have a penis? " she asked with a sly smile.

I managed to smile back at her. "I think you are incredibly beautiful and would do anything to look like you. If I could change places with you, I would. If you had a penis, I would let you do anything you wanted to me." I blurted out.

She laughed. "Aww, thank you. You really are a sweet kid. But think about it...If you were me, you'd have to be with your brother! Would you really want that?"

I tried to be funny. "Well, you seem to like being with him..."

She laughed again. "You're right. I do. He really is a great guy. You're so lucky to have him looking out for you. Remember, he's the reason I'm here."

Yeah. He's really swell. But I couldn't tell her that.

She picked up the bra and slid it over my arms. She stood close in front of me and reached around and fastened the hooks. She smelled terrific. She stepped back and looked at my body again. "You know, you do have a feminine body. We could really make this work". She picked up the panties and knelt down in front of me. She looked up at me and giggled. "You know, I don't ever recall being in this position and not having a raging hard-on in my face."

I realized that my penis had softened during our conversation. I was embarrassed as it had returned to its miniscule state. If I were normal, being so close to such a beautiful girl, I should have been highly aroused.

She must have sensed my thoughts and said "I'm not upset. If the thought of a girl does not get you excited, it is ok. I am more flattered that you think I am beautiful. When we are done, I am sure you will be so happy, you won't believe how big and hard your dick is!" As she stood up, she pulled the panties up to my waist. "I can't believe my stuff fits you so well!" She then startled me when she reached down the front of the panties and grabbed me. "The first thing you need to do is learn how to put this thing away. You have an advantage, being its small, but event he slightest bulge can give you away. As she pushed my penis down in the front, she reached around me and, putting her hand between my legs, grabbed it a gently pulled it back through. Then she adjusted the panties.

She reached back into the bag and pulled out a pile of tissues. "These work much better than socks" she said as she began filling my bra with them. She studied her work and after a few more adjustments, seemed satisfied with the results. "Sit down for a sec" she said, gently pushing me onto the bed. She grabbed the stockings and slowly worked them over my feet and up my legs. I could not believe how great they felt! I was missing out on so much when I was doing this on my own! Next, she slid the mini-skirt up and adjusted it around my waist. Then she slipped the shoes on my feet. They were a little tight. She stood up and pulled me up off the bed. "I waited to do the sweater last for a reason. I didn't want you getting too excited up front. Remember, you can't get hard. If you start to show a bulge, you'll ruin my work!"

She slowly dragged the sweater across my belly and new found breasts. A tingle went through me. She continued to drag the soft wool of the sweater across my skin. It was making me crazy. I closed my eyes and a soft moan escaped my lips. "Careful!" she said. "Remember, no erections!" She pulled the sweater away. "I will not let you wear this if you can't control yourself. How do you expect to be able pass yourself off when you get dressed if you have a hard on all the time?"

I never actually thought about trying to pass myself off to anyone except my reflection in the mirror. I mean, the fantasy of being a girl was just that, a fantasy. I never expected for anyone else to see me like that. And then yesterday changed all that.

She must have sensed what I was thinking and said "When we are finished here, we'll take a ride and see how well we did. OK?" I got very nervous and afraid. To actually go out? Dressed like a girl? I didn't know if I could go through with it. I immediately lost the ability to maintain an erection. Diana began to pull the sweater down over my head. I pushed my arms through and she finished pulling it down over my breasts. She folded the neck over and it was snug under my chin. She made some final adjustments to my breasts under the sweater, commenting "It's much easier when they are real and stay where they belong!" She finished and turned me around. "You really look good. Now, I just need to do your hair and makeup."

Huh? What? She was really taking this too far. "Diana" I said. "I don't know about all this."

"Relax. Your brother told me that you told him you really wanted to do be able pass as a girl. I guess he figured that it would be better to have someone help you, rather than trying it on your own and getting into some kind of trouble. I think you are looking great so far" she said.

She sat me down on the chair and pulled out a brush, a blow dryer and about a million hair care products. "You think it's easy to look this beautiful every day?" she said with a smirk. "You're hair is a bit short. You need to let it grow. I'll do what I can to make it work today. OK?" As she went to work redoing my hair style, she kept the conversation going.

"How long have you been sneaking into your sister's room?" she asked.

"A couple of years, I guess." I replied.

"You've been able to hide it for two years? Good for you! Just her sweaters and bras?"

"Panties too."

"Don't want to be going commando, huh? Can I ask why the sweaters?"

"I don't know, really. I know I love the way some of them feel." I could not believe the ease with which I was answering her questions. She made me feel so comfortable.

"And you the turtlenecks...I bet you love the ones that are high and tight. The snugger the better, right?"

"How do you know?"

She answered, "Why do you think I wear them? The best part is, and this is why my smaller boobs are a benefit, most of the time I don't even wear a bra! You can't imagine how hard my nipples get rubbing on the sweater all day. It is the best feeling in the world. And the tight necks..." she sighed. "They make me feel submissive without having an actual slave collar on."

"I thought I was the only one who felt that way." I said, amazed that I seemed to have the same feelings as the beautiful woman before me.

"So what do you fantasize about when you are dressed?"

"About being a girl and wishing it was all real."

"What do you mean by 'all'? Are you just talking about the breasts?"

"No, the entire thing. Being a real girl, kissing a boy. Letting him touch my breasts. Pleasing him."

"How? Spell out a fantasy for me."

I began to tell her about my fantasy dates with Brian. The kissing, the fondling, my submission to his wants.

"Well, you have a lucky pillow there! What kind of things does 'he' want you to do?"

"Well, yesterday he wanted me to suck on his dick" I said.

"And did you?" Diana asked.

"Yes."

"What did you use?"

"I had a banana."

She laughed. "A great choice. Cucumbers work well too! That's how I learned. Can you deep throat it?"

"I tried. I just keep gagging."

"Well, we will work on that. Hang on." She broke out the blow dryer and continued to rework my hair. "OK. I think that's good enough. Let's get the make up done and we'll go."

I sat there as she began to apply the makeup. She made me close my eyes, open them, purse my lips, smile, frown. The amount of face adjustments I made were tremendous. She finished and asked "Ready?"

I was nervous. "I guess so...".

"Close your eyes". I did so and she led me across the room to my mirror. "OK. Open." she said. I opened my eyes. I blinked. I blinked again. I could not believe that I was looking at myself. Never in my wildest fantasies did I think I could ever be this beautiful. I was a girl! It really was me! Diana had done a great job. I saw her looking at me in the mirror. I couldn't speak. She was smiling. I turned to her and gave her the biggest hug I ever gave anyone. "Don't you start crying" she said. "So, Beautiful. What's your name?" she asked. I looked back in the mirror at my now feminine beauty. "Charlene", I managed to say.

"Well, Charlene. Let's get going. You ready to do some shopping?"

I continued to gaze at myself in the mirror. She finally took my hand and led me out to her car. "We're going to hit the outlets. Your brother gave me a few bucks and said that you can get some of your own clothes. Welcome to the wonderful world of being a female, Charlene! It's amazing how much money you can get out of a guy!" she laughed. "And you didn't even have to do anything to get it!" Only if she know, I thought.

As we drove, she explained our cover story to me. "Nobody in a store is going to question that you're a girl. We're just two friends out shopping. If you see anyone you know, just tell me and we will try to avoid them, just in case. I don't think many of your friends would be out shopping now right? You still supposed to be in school. If I see anyone I know, I'll introduce you as my cousin. Got it?"

I nodded. I had the visor down and was staring in the little mirror, still amazed at how good I looked.

"So back to your fantasies" Diana said. "They all involve you, as a girl, being with either a guy or a girl, but they always have a penis. Right so far?"

"Yes" I answered, still mesmerized by the sight in the mirror.

"Do you jerk off during these fantasies?

"No. Almost never."

"Why not?"

"It reminds me that I have a dick, as small as it is, and I'm never going to be a real girl. I mean, right now I look great, but I'm going to have to go back to being a boy tomorrow. I manage to satisfy myself, not by jerking off, by fingering my ass. If I play long enough, I can make myself come."

"You really do play the submissive role, don't you?" Diana questioned.

"I don't feel right being the boy."

"Just because you're a girl doesn't mean you have to be submissive, you know."

"What about you?" I asked her. "You even said you like having a collar on."

"I don't always play the submissive. There are times when your brother and I have 'normal' sex. And there are times when he likes to be in charge. There are times when I think about being a really trashy, slutty whore. When we both are there, the sex is great." she explained.

"So, my brother is a good sex partner? I asked

"He is for me. When we are on the same page, we really do have great sex. He might not be good with someone else, or I might not be."

"Is his dick as small as mine?" I asked, already knowing the answer.

"I'm sorry to say, no. Seems like you are the cursed one. He is not huge, but he is just right for me. I can give him great blow jobs, take him all the way to his balls. He knows how to fuck me too. Makes me come almost every time."

"Have you every let him, umm, go in your butt? I asked.

"Yes, but not very often. It is not the most comfortable feeling. I couldn't imagine having someone with a bigger dick trying to do it down there. The first time, he got me without warning. He had me so hot and wet...He was just sort of playing with my hole, poking a finger in lightly. Next thing I knew, he was filling my ass with come."

"If you don't like it, why do you let him do it?"

"All part of the game, dear. We have codes. It's a great erotic game we can play and no one knows. If we both wind up wearing certain things on the same day, the winner get to make the rules. For example, if he has his football jersey on and I have on this sweater, I win." she said as she ran her hands over the sweater. "If I have on the sweater you're wearing, he wins. And his Ranger jersey beats this sweater, but loses to yours. So each item can be good or bad, depending upon what the other one wears. Some days, I hope I win. Some days, I hope I lose. I gave you that sweater today because I know he has his football jersey on and I am in the mood to win today. I won't need to wear that until I want to lose."

"Sounds like you two have it all worked out"

"We definitely get along excellently well. Both socially and sexually. I really do love him and know that I would spend the rest of my life with him. But don't ever tell him I said that!!"

We pulled into the shopping center. We hit Victoria's Secret first and came away with 2 matching sets of strapless bras and panties. I had the best time in the fitting room trying them on and modeling them for Diana. We headed to the Limited and picked up a form fitting, white, high neck turtleneck sweater and a blue Icelandic mock turtleneck from the Gap. She paid for everything with cash. "I wish your brother gave me money to buy some stuff for myself once in a while!" she joked.

Before we headed back to the car, she said she had to pee. "Come on, Charlene. Come to the bathroom with me. You know us girls always go in pairs." She had the cutest giggle. She led me to the bathroom and said "Remember to sit!!" It was 3:30 when we got back into the car. "Do you want to get something to eat?" she asked. "We could grab some Mickey D's by the school. They should be busy about now. Are you brave enough to eat there?"