Edited by Victor G.
16 year old Darren Peterman proves that he's very good at being a boy, giving his mother some concern about his future. Why would a boy who is so good at being a boy want to give it up to become a woman?

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Chapter 4
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I woke up the next morning on my stomach. Actually, I woke up on top of my new - albeit fake - breasts. Usually, I sleep on my stomach, but my new artificial feminine assets forced some changes to how I slept. I sat up and felt a dull, aching pain in my lower back from my awkward sleeping position. I'd have to make some considerable changes to my sleeping habits if large, mature breasts were going to be a part of my life.

I looked down at the breast forms jutting out from under my silky nightgown. I ran my hands over them and smiled. This is incredible, I thought as I got out of bed.

I looked at myself in the mirror as I was getting socks and underwear out of my drawer. Without my make-up and a wig, I looked like myself with big boobs and nightgown.

I pictured myself the way I looked yesterday, as a pretty, bespectacled blonde in her early thirties. Tomorrow, if things went the way I hoped they would, I'd look even older. I'd finally look exactly the way I desired, just like a sophisticated, attractive woman firmly in middle age. I felt my penis stiffen at the thought as it rubbed against my silky nightgown.

Looking down at my gown, I began to feel embarrassed. It was Friday, a school day, and I had to take a shower and get ready for school. I hoped none of my family would see my excitement as I walked down the hall to the bathroom. Since I was back in "boy mode", I also hoped no one would see my in my nightgown. I wanted to take it off before I walked down the hall. However, the greater fear of being seen with naked breast forms swinging from my chest kept me from doing so.

I grabbed a pair of jeans and a button-down Oxford shirt before heading to the bathroom. I hoped my mom was right about the breast forms coming off in the shower. If I couldn't get them off, it was going to be a very, very long day.

Thinking of the day ahead at school, I thought about my friends on the team. What would they think if they could see me like this? I wondered if any of them could possibly understand. I knew I wasn't the only boy in the world who dreamed of being a woman, but was I the only one on my team? Probably so, I thought as I turned the hot water on and slid off my nightgown.

Any embarrassment I felt faded as I stared into the mirror. I marveled at how real the breast forms looked as they clung to my naked chest. If I didn't know any better and I was looking at a picture of myself from the neck down, I'd say they were real. Come summer, if I wanted, they would be completely real. I'll have to wear a bra every day for the rest of my life because I won't have a choice. I'll be a middle-aged woman with a middle-aged woman's voluptuous breasts. My penis seemed to like that idea because it sprang back to attention.

As I stepped into the shower, I wondered if I would be doing this if it wasn't such of a turn-on for me. Am I really that crazy, I thought as I soaped my chest, trying to work the breast forms free. I'm fucking up my whole life for some kind of sexual thrill. After a few moments of prying, the breast forms slid off my chest and I placed them on the top of the toilet. I cleaned up the residual glue off my chest and finished my shower.

After I was done getting showered and dressed, I went downstairs for breakfast and saw Mom - for a moment, I thought of her as "Karen" - in the kitchen. Sammy's school starts earlier than mine, so Dad - "Bill" - dropped him off on his way to work. I remembered the look on Sammy's face last night when he saw my transformed self, how I looked in the makeup, padding, dress, and wig. He took it well but I could tell he was disgusted. The little brother who used to look up to me thought I was a sissy, and he was right.

Mom greeted me and said I looked nice. I thanked her, poured a bowl of cereal, and sat down to eat it. For a moment, I dreaded that she was going to lecture me about my confession about wanting to become a smoker while dressed as my older female alter ego. Dad and Sammy came in before we could talk about it.

I watched as Mom removed one of her Marlboro Light 100s from her case and lit it. What would I do if she offered me one? I'd have to decline because there was no way in hell that I'd be able to smoke in front of her or anyone else dressed in my boy clothes. This may not make any sense, considering how badly I wanted to smoke while dressed as an adult woman, but the thought of smoking as a boy utterly disgusted me.

"You did good last night in front of your dad and Sammy. Was it hard?" she asked.

I replied that it was one of the hardest things I ever had to do in my life. "They'll never look at me the same way again," I added. "Will they?"

"No Sweetheart," she said, a little sadly, as she patted my hand gently. "I'm afraid they won't. But on the bright side, you got it over with and the next time you're 'Nancy' in front of them it will be much easier."

I told her that I hoped she was right and then I told her she looked nice.

"Thanks," Mom replied. "I had to get dressed up because I'm showing a house this morning," she said.

My mother is a real estate agent. Its a great job because she can work out of the house and its also a good excuse for her to keep her wardrobe up. I envied her elegant businesswoman look: her beautiful, long salon-styled hair and perfectly applied makeup, the stylish tan suit jacket and matching calf-length skirt and black leather high-heeled boots. I couldn't wait for "Nancy" to wear an elegant outfit like that.

My mind drifted for a moment, thinking about Nancy's businesswoman chic, how it would feel to be out in public dressed that way. Would Mom maybe even let me show a house as one of her Realtor "associates"? That would be amazing!

Well, let's just get through today first. And the total transformation tomorrow, I thought with a sly smile.

I finished my cereal and put the bowl in the sink. I kissed Mom on the cheek and told her I'd look for her and Dad after the game tonight.

"Be careful on your way to school," she said.

I told her I would and then I closed the door behind me and walked to my car.

I thought about the moment I had shared with my mom as I drove to school. She could have something about the smoking, but she didn't. I was disappointed because I'd opened my heart to her and I was ashamed for the same reason. I had given her too much information.

Regret is the word of the day, I thought as I pulled into my designated parking spot. I regretted making a sissy out of myself in front of my dad and Sammy and I regretted telling my mom about what I thought of her smoking. I felt like a loser as I walked into the school, hoping the day would get better.

*****

The game against Wesley High helped lift my spirits. It was a huge win for our team. We weren't expected to win, but we pulled it off, and winning that game made the next game that much more important. I played the best game of my entire life. I made 9 open field tackles and 2 interceptions. The second interception set up our winning field goal, making me a hero among my teammates and the fans. For the first time in 20 years, our school was on track for the state playoffs. Of course we'd need to beat Henderson the following week, but the odds were definitely in our favor. Henderson had only won two games the whole season.

After we all got home, my dad and little brother couldn't stop talking about the game. They were proud of me and they said so. That should have made me happy and it did in a way but in another way it made me feel worse about things.

I had just proven what my whole family already knew about me. I was good at being a boy. So why did I want to be a woman? I'm sure that was the million dollar question running through my father's and Sammy's mind.

The important thing was that it was enough for them to know that I wanted - needed - to become an adult woman. In spite of the hero worship, it seemed as if they were going to respect my decision even though they didn't understand it.

My mother came to my room as I was getting ready for bed and asked if we could talk. I actually felt comfortable talking to her as I wore my nightgown, and truly appreciated her understanding.

Mom sat down on the bed. "You played great tonight," she said as she gingerly took my hand. "I guess that means you're going to be a boy for a little longer than we expected."

"Because of the playoffs?" I asked.

"Yes. That means at least another week of practice," she said, "Are you okay with that?"

I nodded. "I had the best game of my life tonight, but it doesn't change anything," I said. "I still have a commitment to the team, so I'll play football for a little while longer. But once that's done, I still want to be a woman."

"Are you sure about that?" my mother asked. "Because from where I was sitting tonight, it made me wonder if becoming a woman is really the best thing for you."

"I don't know, Mom. Maybe it's not the best thing for me, but I know it's what I want more than anything. I've always wanted this and I know I'm never going to stop wanting it."

My mother told me about sitting in the stands and watching the game amidst all the students. "They were having such a good time," she said. "I remember what it was like to be a teenager and it was one of the best times of my life. And it only got better when I got in my twenties. Then again, my thirties weren't that bad either. I'm just afraid you might regret missing out on those times. It's strange enough that you want to be a female, but why would you want to miss out on the best years of your life?"

I told her that I understood what she was saying but I didn't feel the same way. "It's not the same with me, Mom. I don't like being a kid. And I don't want to go to college. I don't want to be a boy or a man or a girl, either. I want to be a grown woman like you. I want to be beautiful and elegant and wear nice clothes and makeup and jewelry. I want to talk like an adult woman, move like an adult woman, and have an adult woman's life and habits. I want do what adult women do, like shop and play bridge with your friends and gossip."

Mom smiled slightly. "There's so much more to being a woman than just playing bridge and gossiping with your friends," she said.

"I know that," I replied. "But that's all I can think about right now. I want to learn the rest and you said you'd teach me."

"I will, if that's what you really want," my mother said. "But let me tell you a little bit about the hard truth. The life of a woman isn't as glamorous as you think it is and it's not fair either. We live in a man's world and men have it a lot easier."

"Are you saying you don't like being a woman?" I asked, surprised at what she said.

Mom shook her head vigorously. "No, not at all! I love being a woman, but it's the only thing I know. It's not the same way with you. You're a boy and you only know what it's like. Tonight, you were a hero to a lot of those people in the stands. Didn't that feel great? Most women will never get to feel like you did tonight. Would you willingly give that up?"

I thought about what she said for a moment before responding. I wanted to choose my words carefully, to make sure Mom fully understood. "I might have been a hero tonight," I said. "But you've been my hero every single day of my life."

I saw a small tear form in the corner of my mom's eye. She wiped it away, hoping I didn't notice. "That's what you said the other night," she said, trying not to sound too choked up, "And I haven't stopped thinking about it."

I squeezed her hand tightly. "It's true, Mom. When I was a little kid, I knew that I wanted to be just like you when I grew up. But I never really thought it was possible. Now that I know it's possible, I can't wait until I get older. I want to be like you right now."

"And you're sure of this?" she asked. "You don't think you'll change your mind about this someday or have any regrets?"

I looked at her levelly and spoke with the utmost confidence. "The only thing I'll regret is if I don't do this."

Mom nodded in understanding. "In that case, how would you feel if I made an appointment for you to see Dr. Girardi? I think she'd be willing to start you on female hormones right away if you're absolutely sure about this."

"Oh, Mom! Really? Are you serious?" I asked excitedly.

Mom smiled as she caressed my silk-clad arm with her finger. "You made quite an impression on me last night and tonight," she said as she reached up to touch my cheek. "I wouldn't want puberty to rob you of a lovely, feminine face. I think the sooner we get you on female hormones, the better it will be for you."

I hugged her tight and thanked her from the bottom of my heart. She rubbed my back lovingly.

"You do realize of course that there's going to be some serious physical ramifications to starting female hormones?" she asked.

"Like boobs?" I replied.

Mom grinned and nodded. "Uh-huh," she said, "But I think you should start calling them 'breasts'. Grown women don't usually refer to them as 'boobs'. In addition to that, you're going to start gaining weight in all the wrong places for a boy. It could be a little embarrassing if you started developing before summer vacation."

I asked her if that was supposed to scare me into changing my mind.

"No," she said. "It's just food for thought."

"Well, it can't happen fast enough for me," I said. "I can't wait to look like you."

Mom batted her eyelids sarcastically at me. "I'm truly flattered," she said. "But I want you to be your own woman. Don't be a copy of me."

I smiled reassuringly. "Okay, Mom."

She kissed me on the cheek and said, "I'll call Dr. Girardi first thing Monday morning. Now get some sleep because we have a big day tomorrow!"

Mom got up and turned off the light.

"Good night, Mom," I called out.

"Good night... Nancy," Mom whispered.