Co-written by Victor G

16 year old Darren Peterman faces the prospect of telling his father and little brother that he wants to be an older woman like his mother.

******
Chapter 2
*******

As soon as I walked into the living room and saw my little brother on the couch, my elation at the prospect of living as an adult woman quickly ebbed away. Sammy, completely unaware of my drastic decision, had a look of awe on his face as I walked past him and sat down on the love seat.

I felt a pang of fear as I removed one of Mom's women's magazines from the magazine basket. I quickly laid it down and opened it before he could see the cover - Ladies' Home Journal, one of my favorites. I couldn't help myself, I just adored the makeup and fashion articles, and couldn't wait to try them out in real life. I hoped Sammy thought I was reading Sports Illustrated.

I was on a roller coaster of emotions and the ride was about to start. My greatest fear had come true: my parents had discovered my secret. Of course, I'd done a less-than-admirable job of hiding that secret over the years, which is how they found out. It bothered me deeply that they knew I was less than a boy. However, their support changed everything. According to my mother, my parents were behind me 1000 percent. They weren't just going to let me crossdress in my room unseen by anyone but me. They were going to help me become a middle-aged woman.

I was drunk on the thought of becoming a woman. I was so drunk that I was incapable of comprehending all the consequences that came along with becoming a woman. The first of which was sitting across the room from me.

How was I going to tell Sammy about this? How can I explain how desperately I want this? What would he think of me? Would he tell his friends and would my friends find out? I'm not a stupid guy. I knew I couldn't hide something like this. People were going to find out. It wasn't a question of "if". It was a question of "when".

I was engrossed in an article about women's boot trends for the fall and winter when my dad came home from work. He greeted Sammy and I as he hung his coat in the closet, although there was an odd look in his eye, one Sammy didn't catch. Did Dad see the Ladies' Home Journal on my lap? According to my mother, he had an idea about what she and I had talked about today. As he walked past me into the kitchen, I knew he'd ask my mother how the conversation went.

I strained to hear what my parents were saying but couldn't make it out over the television. I almost asked Sammy to turn it down, but thought the better of it. If I couldn't hear Mom Dad, then neither could Sammy. But it didn't matter, becasue Mom said we'd tell Sammy tonight. That could only mean we'd talk about it over dinner.

I looked over at Sammy on the couch. In a mere 30 or 40 minutes, I'd lose his respect and admiration for the rest of my life. I was sure I'd already lost my father's. Was the pleasure and excitement of dressing up like an adult woman really worth the impending loss of respect?

I wondered what my father thought of me. I'd probably been a disappointment to him my whole life. I looked like the perfect son on the outside, but he was well aware of my lifelong struggle to stay out of my mother's closet. The lure of Mom's clothes was bigger than my ability to resist, though, and he knew it. It probably didn't matter to him that, to compensate, I became a pretty decent cornerback and wide receiver in football and a better outfielder in baseball, in spite of my slender frame.

For all I knew, Dad probably thought my dates with girls were some kind of a front. I liked girls, I wasn't gay. I wasn't a virgin, either. For a boy of only 16, I'd kept fairly busy in the sex department. I'd had intercourse with two different girls and had gotten a total of five blow jobs - all from girls, of course. Gay guys don't do stuff like that. But my father didn't know that. It wasn't like I came home and told him about my sexual exploits.

I was beginning to realize that I'd been thinking with my dick when I said yes to my mother. A silly thought popped into my head: Don't let your dick make an appointment for you that your ass can't keep.

I felt like I was suddenly on death row and tonight was the date of my execution. The dinner waiting for me would be my last supper. Am I being too dramatic? I don't think so.

Obviously, I don't know how a prisoner feels in the moments before he meets his maker, but this must be pretty close. The analogy definitely reeked of symbolism and irony. My parents would tell Sammy and my life as a boy would end. But unlike a prisoner, I'd get a new life, and wasn't that a good thing? Of course it was! It had to be, unless I was making the biggest mistake of my life.

I thought some more about the prisoner on death row. He doesn't have the luxury of putting an end to his own execution. He can't go to the warden and say he's changed his mind, but I can. I can get out of this chair, march into the kitchen, and tell my parents that I don't want to go through with this.

The thought of calling it off made me feel both relieved and sad. Relief at the thought of saving myself from the humiliation that was sure to follow. Sadness at thinking of missing out on the joys and pleasures of living my life as a sophisticated middle-aged woman named Nancy Peterman.

But oh, how I wanted that so very badly! I wanted to look in the mirror and see a well-dressed, attractive middle-aged woman staring back at me. To get to wear makeup - lots of makeup to hide my age and gender - and stylish, feminine designer outfits and expensive shoes and jewelry. That would be amazing!

And to get to actually live as that woman, with no one the wiser as to my true identity. To be out in public, acting like an adult woman, talking like an adult woman, moving with an older woman's grace and self-assuredness. To all the world, I'd be 46-year-old Nancy, an attractive, successful businesswoman, not simply 16-year-old Darren, a plain, everyday high school boy.

Mom said she'd help me become Nancy, could I really walk away from that? It was so close, almost within my reach! I just had to say "yes" and all my dreams would come true...

I could feel a tightening in my parts when Mom called out from the kitchen. "Time for dinner!" she said. Sammy sprung off the couch and raced to the table. I was much slower, unsure of what to do.

I took my seat across from Sammy and next to my father. Mom took a casserole out of the oven. My dad touched me on the arm and asked if everything was all right. I didn't want to look him in the eye, but I had too. He was sitting tall in his chair but I could tell he was in pain. He looked like a man who was on the verge of losing his son. I told him I was okay.

"Are you sure about this, Darren?" he asked. "Because things will never be the same once we start with this."

I was still questioning my reasons and motivations for wanting to go through with it but I had to do it. The only thing made sense to me was that it was the opportunity of a lifetime. How could I say no? But how in the hell could I say yes?

I lied to my father. I told him that I'd never been so sure of anything in my life. He squeezed my arm and then he wiped a tear from his eye as my mother dished a serving of lasagna onto my plate.

Dinners at my house are great, not because my mom is such a good cook, but because my family talks a lot. I know from talking to my friends that its not like that at everyone else's house. I've always said that when I grow up and have my own family, we're all going to have dinner together every night. Of course I always thought that when I grew up, I'd be the dad. I was now facing the prospect of being the mom. But I was thinking about it in a technical sense because in reality, I'd never be able to marry a man. That would be crazy. The ugly truth of the matter was that if I became a woman, I'd probably live alone. I supposed that was just another one of unraveling consequences I'd discover.

Unlike most dinners, though, this one was quiet. The conversation between my parents seemed forced and canned. How was your day? Anything new happen? I wondered when someone would say something. Did my parents expect for me to start it? I hoped not.

Twenty minutes or so after we sat down, dinner was finished. It had gone fast but it seemed very slow.

"Can I be excused now?" asked Sammy as he prepared to get up from the table. "I want to go over to John's house and play XBox with him."

"Not just yet, Sammy," Dad said, a little hesitantly, "Your mother and I want to talk to you a little bit about some things that are going on with Darren."

My mother got up from the table and retrieved an ashtray and her cigarette case while my father set the stage with Sammy. I took a deep breath, dreading the rest of the conversation.

"What's going on with Darren?" Sammy asked, alarmed, "Is he in trouble?"

"No. Nothing like that," my father said as my mother lit a cigarette. "Its just that he's going through some changes- some very sensitive and very confusing changes, and I'm afraid its going to affect all of us, especially you. We just wanted to talk to you about it."

Sammy looked across the table at me but I looked away before our eyes could connect. "Are you sick with something?" he asked. I shook my head.

"I wish, that might be easier," I muttered under my breath so that no one could hear me.

"Your brother isn't sick, honey," my mother said. "At least not in the way you're thinking. But he is going through a difficult time and he's having to make a lot of difficult and grown-up decisions, and he's going to need our help and understanding and love to get through this. He's especially going to need your understanding and support because you mean the world to him."

I looked over gratefully at Mom. She really did mean to help me with this. So far so good, I thought. I was really impressed by the way she started the conversation, because I couldn't have done it like that in a million years.

My mother exhaled her smoke toward the ceiling and said, "The easiest way to explain this is that Darren feels like a woman who is trapped in a boy's body."

I slunk down in my chair even though I had to admit my mother had made that part sound better than I thought it could.

"I don't get it," Sammy said. "Darren's a boy like me and Dad."

"No. Not really," my mother said, "Darren looks like you and Daddy on the outside, because he was born a boy the same way you were. But on the inside, Darren is a woman like me. And in order for him to feel good about himself, he's going to need for us all to think of him as a woman and treat him as one. Do you think you can do that for your brother, Sammy?"

Sammy raised his eyebrows and shook his head, trying to comprehend what he was hearing. "You mean Darren is going to start being a girl?"

Mom smiled and patted his hand gently. "Not a girl, dear - a woman," she said. "A woman is older than a girl. I'm a woman. Darren is going to be an older woman like me and Mrs. Jackson and Mrs. Estes. He won't be your brother any more. He'll be your aunt."

"LIke Aunt Carol?" Sammy asked.

"That's right," my father said. "And this is where we need your help. It's going to take some time for Darren to look like an older woman all the time. In the beginning, he'll just be doing it after school and on the weekends, and that shouldn't be too much of a problem."

"You just can't tell any of your friends what he's doing," my mother said. "That's so important, Sammy, and I need for you to promise us that you'll keep this secret and never tell anybody. Not even John."

Sammy bit his lip and wrinkled up his brow.

My father interrupted my mother and said, "When school gets out for the summer, if he wants to, Darren is going to get an operation that will give him boobs like your mother. Now when that happens, he's going to start living as a woman every day and every night. And when that happens, we're going to tell everyone that Darren went on a trip to Europe."

"Europe?" asked Sammy. "That's a long ways away."

"That's right," my mother said. "But he's really not going to Europe. That's just the story we're going to tell people when they ask where he is. He's really going to be at home with us, but he'll be a woman just like me."

"Why are you doing this to him?" Sammy asked. "Did he do something bad? Are you mad at him?"

"Not at all Sammy," my father said, "We're not doing this to punish Darren. This is what he wants."

Sammy looked across the table and asked me if I really wanted to be a lady like Mom.

I took a deep breath and nodded. "Yes," I said. "I know this sounds crazy and weird, but I've wanted to be like mom for as long as I can remember."

"What about football and baseball?" Sammy asked. "How are you going to play sports if you're a woman like Mom?"

"He's not going to have any surgeries until the summer," my father said. "He's got two more games of football and he's going to play them and we'll just have to see what happens during baseball, but he can play if he wants."

"So does this mean you like boys or old men?" Sammy asked.

My face burned with shame. Oh my God, I thought. I knew this would happen. He thinks I'm gay. I was going to say no, but before I could answer, my mother spoke for me. "Only time can tell, but it would be very natural and normal for Darren to start dating older men once he becomes a woman. I think it would be wonderful if Darren could find a man who makes him as happy as your father make me."

The temperature of my skin shot up another ten degrees as my little brother said yuck.

"Your mother is making a very good point, Darren," my father said. "I know you've always dated girls and from what I can tell you've never been out on a date with a guy, but I also know that can change once you begin living your life as a woman. And if that happens, I don't want you to feel bad about it. Its like your mother said. It's absolutely normal and natural for women to date men and you are on your way to becoming a woman."

I groaned audibly and said that I didn't want to think about things like that right now.

"So are we clear on this, Sammy?" my father asked.

"Clear on what?" Sammy asked. "That Darren is going to be a woman?"

"Yes. And just as importantly, this is our little secret for right now," my father said. "I just want to make sure you're not going to tell anyone about this. Are we clear on that?"

"Yes, Dad. I got it," Sammy said. "Can I go to John's house now?"

"Okay," my father said. "Just keep this to yourself and remember what we said about not telling anybody. Anybody."

Sammy got up from the table and raced out of the house. I knew he wanted to get out and leave the situation behind more than he wanted to play xBox with John.

"Well, that went well," my mother said. "Don't you think?"

My father and I both agreed.

"Okay, Darren," my mother said. "What do you think about us two women cleaning up the kitchen? When we're done, we can go to my room and pick out a nightgown for you to wear to bed tonight."

******

After doing the dishes, I followed my mother up the stairs to my parents' bedroom. While we were on the stairs, it occurred to me that this was a "first" and that I was probably embarking on a lot of "firsts". This would be the first time I ever wore something of my mother's with her blessing. I was excited about it but I also felt a little reluctant, thinking of my prior punishments for doing just such a thing.

Once we were inside, my mother closed the bedroom door. I don't know if we needed the privacy, what with Dad downstairs and Sammy still at John's, but I was thankful for it. I watched as my mother quietly removed a long white cigarette from her leather cigarette case and lit it. My mother smokes a bit too much but I think she looks good doing it, as weird as that is to say these days. Most of her friends smoked too so I guess I grew up thinking it was normal and right for women to smoke. However, for me, the same thoughts didn't apply to grown men or to teenage boys and girls. As far as I was concerned, smoking is a woman's thing.

"You're a little taller than me," my mother said, "but I think I have a gown that is little big on me." She grinned and said, "But I'm sure you've probably already worn it a time or two anyway."

I laughed nervously and nodded in agreement, knowing which nightgown she was referring to. My mom is five-feet-six and weighs about 140 pounds. I'm 5-feet-eight and weigh about 160. Now that I'm getting older and bigger, her clothes are kind of tight on me. Lately, though, it seems as if I've stopped growing. I wonder if this is as big as I'm going to get. That would be fine by me, right now I think I'm a pretty decent size for women's clothes.

I followed her to the closet and watched as she sorted through the clothes on the hangers. She's a beautiful woman and I'm not just saying that because she's my mom. Her hair is brownish red and is cut so that it flares back against her cheeks and hangs softly against her shoulders. The red is from the highlights that she has done at the salon once a month. She wears glasses and they make her look smart. She also wears a pearl necklace. I know they're real because I heard her talking to one of her friends about them.

My mom has a lot of friends in the neighborhood. She mentioned two of them at dinner tonight, Mrs. Jackson and Mrs. Estes. They were always spending time at each other's houses during the summer so I supposed they did the same thing when I was in school. I wondered if I would meet Mrs. Jackson and Mrs. Estes as a woman. I was thrilled at the idea of being a part of their gang even though I doubted they would accept me as one of them. Not to mention that it would be more than a little embarrassing for me.

"I think this should fit you," my mother said as she removed a long chiffon gown from its hanger and handed it to me. "It has a house coat that goes with it. Would you like that too?" she asked.

I bit my lip and nodded. I knew exactly which robe she was talking about. She pulled it out of the closet and draped it over my hands. "Silk feels so good against the skin for sleeping in," she said, and I agreed with her.

I think she was feeling almost as awkward as I was, which is why it surprised me so much when she hugged me and kissed me on the cheek.

"I don't know if I've told you this today, but I'm very proud of you," she said. "I think you're very brave."

"Brave? You got to be kidding," I said. "I'm scared to death and I can't believe I'm really doing this. But now that we've told Sammy, I guess it's too late to back out of it."

"Is that what you want to do?" my mother asked. "Back out? Because you can if you want to. Your father and I would certainly understand. Anyone would. And if you need more time to think about it, then that's fine, too. You're making one of the most important decisions of your life. If you have any doubts, this is the time to deal with them. It might be too late to change your mind once you get the surgery and start taking female hormones. And if you do start taking the hormones and have the surgery, then you really will be like me. It won't be make believe anymore."

I told her I couldn't think of anyone better to be like than her. "All my life I've wanted to be just like you."

Mom laughed and said, "I know you do sweetie. And to be honest with you, I've never understood why. I always thought that boys who wanted to be girls wanted to be real girls instead of old women like their mothers. I just hope you'll be very happy as a woman."

"Me too," I said.

She walked over to her dresser and trimmed the ash from cigarette into an ashtray. "I'll tell you something," she said, "If you promise not to get mad."

"Okay. Tell me. I want to know."

"Promise you won't get mad?" she asked.

I promised.

She grinned broadly. "I'm really excited about this," she confided. "But the last thing I want to do is to influence you in any way. I want you to be a woman because it's what you want to do and you think it will make you happy. Not because you think it will make me happy."

"I'm glad you feel that way," I said. I assured her that I was doing this for myself but I also told her that I thought it was cool that she was actually happy about helping me.

"It's hard to explain," my mother said, "but there's something very arousing about feminizing a man. I know you won't understand that and I don't expect you to but I'm really looking forward to taking this journey with you and helping you along the way in any way I can."

I asked her about all the other times she and Dad had caught me with her clothes. "Weren't you mad at me?" I asked.

"No, but I had to pretend like I was. I don't want to hurt your feelings, but I'm sure you can imagine your father was very disappointed when it turned out you had a feminine side. I tried to make him understand that maybe it was for the best but until now, he didn't see it that way. As a parent, I had to put up a united front with him even though I didn't want to. But now it's okay! We're both free to enjoy this and make the most of it. Isn't it great?"

I agreed.

"So how do you feel about standing on the verge of adulthood?" she asked.

I asked her what she meant by that.

"Isn't it obvious?" she asked. "You're only 16 but after Saturday, you're going to look as if you're 46 and that means you're going to have to act like it. Of course it goes without saying that you're still my child and there's going to be rules, but your father and I have both agreed that we're going to treat you as an adult woman when you're dressed for the part because that's how other people you meet will treat you. Does that make sense?"

I nodded my head and smiled as I thought about the benefits. "Does that mean I can drink alcohol like you and Dad?" I asked.

Mom smirked at me. "That would be the first thing you'd ask. Yes, you can drink alcohol, but not to excess. While you're dressed, you need to maintain the illusion of being an adult woman at all times. That means walking, talking, and acting just like an adult woman, and you don't want to risk that by getting drunk."

She had a good point, and I nodded in agreement. I was, however, intrigued by the idea of getting to indulge in adult habits, with no one to tell "Nancy" no.

"Besides," Mom continued, "I don't drink to get drunk and neither should you. It's not very ladylike. But an occasional glass of wine or a mixed drink wouldn't be out of the question."

"Cool!" I said.

"I can't believe it," she said excitedly. "My son and I are going to be best friends- like sisters!"

"So if we're going to be best friends and everything, does that mean I'm going to start hanging out with you and your friends? As a woman?" I asked.

"How would you feel about that?" Mom replied. "Would it bother you? I know it would be embarrassing for you to get dressed up in front of my friends, but I think it would be a good experience for you. It would be a good way to learn adult female mannerisms and behaviors."

I felt really excited at the idea of being included in Mom's circle of friends.

"Plus," Mom said, "If you're going to start living your life as an adult woman, people are going to expect you to be friends with other adult women. Of course, if you don't think you're ready to meet my friends as a woman, then I'd completely understand."

I shook my head vigorously, not wanting Mom to misunderstand. I desperately longed to be "one of the girls"!

"Oh no, Mom!" I said emphatically. "I was just asking because I'd love to hang out with you and your friends and you know, be like one of the girls, like you are."

Mom smiled and said, "I can't wait to teach you how to play bridge."

"Me too. Is it hard?" I asked.

Mom shook her head no and said that if I could play poker, then I could easily learn to play bridge. "It's too early to go to bed," she said. "Do you want to put on your nightgown and watch TV with your father and me?"

I told her that I'd rather wait until I could do it right before I dressed up in front of Dad. "I think I'll put on my gym shorts and go for a run."

"That's right," my mother said. "At the moment, you're still a football player. For the next two weeks, at least."

She kissed me on the head. "I hope you enjoy wearing the nightgown, and when you get home from school tomorrow I'll have some new clothes for you."

I hugged my mom and thanked her. "I love you so much, Mom. You don't know how much this means to me."

"Me too," she said as she hugged me tightly in return.

*******

My run through the streets of my neighborhood was nothing short of exhilarating. The cold November air did wonders to clear my head. I'm not going to say everything suddenly made sense because it didn't, but the brisk exercise did work off some stress and anxiety.

When I got home, I told my parents that I was going to take a shower and go to bed. My mother stopped me as I was going up the stairs. "You can use the razor in my bathroom if you want to shave your legs and under your arms," she said.

Her suggestion caught me off guard because with football and everything, I'd never considered shaving off my body hair.

My father sensed the conflict on my face and told me that I wouldn't be the first guy to shave my legs. "The guys on your team probably won't even notice," he said.

"Okay, I'll think about it," I said as I hurried up the stairs to my parent's bathroom. Oh my gosh, what am I thinking? Am I really going to shave off all my hair? Of course I am. Women aren't supposed to have hairy bodies. But I'm not a woman yet. But I will be soon...

My shower took five times longer than it usually did because I'd never shaved my body before. It was scary and I was glad I didn't cut myself too bad.

I dried myself off and wrapped a couple of towels around me, one around my head and the other around my torso, in a feminine manner. The cool air in the house felt nice against my freshly shaven body. My mother's nightgown and matching robe were lying on top of my bed, beckoning me. I put them on.

The feeling of the silk rubbing against my smooth legs gave me goosebumps. I'd never felt anything so good in my whole life. Except for the orgasm I had five minutes later.

I masturbated myself three times that night before going to sleep, but I was careful when I ejaculated. I carefully cleaned myself using the tissues on my bedside table. I slept blissfully, dreaming of the adventures of a lovely middle-aged woman named Nancy.