16 year old Darren Peterman wants to be a middle aged woman named Nancy. In this chapter, Nancy does a photo shoot and prepares for his upcoming date with Tim Moreland. Why is his little brother, Sammy, being so pesky all of the sudden?

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Chapter 12
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I woke up Friday morning feeling somewhat dazed. Had yesterday really happened? I reached for my cigarettes and lit one. I spotted my collection of styled blonde wigs sitting on my dresser and remembered Mom and Dad taking pictures of me as a 16 year old Nancy. So that part about yesterday really did happen. But what about the other things?

I remembered the fight with Coach Holloway in the principal's office and I remembered filling out the papers in Mr. Edward's office. That part was true too. I'd made an ass of myself and had dropped out of school.

And what about the other thing, I wondered? I reached under my nightgown and felt between my legs. My groin was crusty with dried sperm and I recalled the memories and feelings of the night before.

The last thing I had done before falling asleep was to masturbate to thoughts of Tim Moreland making love to me.

Rather than feeling nauseous or grossed out, I felt defeated with a splash of acceptance and anticipation. Last night hadn't been the first time I'd imagined myself in a man's embrace and it wouldn't be the last. When imagining myself as a woman, I also imagined myself being attractive to men. It was the men in my dreams who lit my cigarettes and flirted with me.

My feelings for men had taken a turn in another direction yesterday and I couldn't help but wonder if they'd been there all along and I'd just been covering them up. If so, it wasn't because I had a choice. I had a reputation to uphold. Guys like me weren't supposed to be gay or be doing any of the other things I was doing. Being who I was had kept me from being who I wanted to be.

I put out my cigarette and lit another one and thought about how good it felt to be a smoker. I couldn't remember a time in my life when I didn't want to smoke like my mom, but I had put that goal on hold because I was a boy and boys like me aren't suppose to smoke like women.

Had my whole life as a boy been a sham? No. Not really. I'd been good at being a boy and I'd be lying if I said my life as such had been anything shy of enjoyable. However, there had been those other feelings and desires on the horizon that had always seemed so unreachable. I had tried not to dwell on them because they made me feel dirty and disgusting and perverted. But more than that, they had seemed unobtainable.

For the first time in my life I felt as if I was being honest with myself about the feelings I had been hiding from. If this had never happened to me, I think I would have gone on to live a normal, productive, and relatively normal life as a man. I probably wouldn't have even taken up smoking but I was fairly certain that I would have married a woman who was older than me and she would have been a smoker. But it did happen and now I was going to be that older woman. I looked down at the cigarette between my fingers and admired it. "I'm as crazy as a shit bird," I said out loud.

The longer I sat up in bed the more accepting I became of my newly discovered sexuality but I was still confused by it.

If I was really gay then I should have been attracted to some of my friends. After all, a lot of them were kind of cute by girl standards, but I had never had any of those feelings for my friends.

I closed my eyes and and pictured Tim Moreland in my head, and when I did, my penis immediately stiffened. And that's when I realized older men turned me on. Tim was the kind of guy my mom and Margie and Susan would go for if they weren't married. I wanted what they wanted because I wanted to be like them.

Having solved the problem of my sexuality, I got of bed and dressed myself in some clothes from the early 90s. I was to be a 25 year old version of Nancy this morning. Margie said we could take the pictures at her house, because unlike the rest of my mother's friends, Margie hadn't updated her furniture or decorations in over 30 years. Her home was permanently stuck in 1976, the year Jimmy Carter had been elected president. I knew that because my mother had quizzed me on the presidents. I think the succession went something like Nixon followed by Ford, Ford followed by Carter, Carter Followed by Reagan and so on and so on up until now. I was getting good at history and pop culture.

******

My mother told me I looked like Farah Fawcett as we got ready to go to Margie's house. Farah Fawcett was one of Charlie's Angels. See, I do know my pop culture.

We collected the rest of the wigs and the clothes that I would need for my costume changes and headed over to Margie's.

*****

After inviting us inside, Margie said that she had invited Susan to join us. "I hope you don't mind," she said. "If you want, I can call her and tell her not to come by."

"I don't mind. Do you, Honey?" my mother asked.

"Fine by me," I said. "As a matter of fact, I was kind of hoping I'd get the chance to talk to all three of you. There's been some things that are kind of bothering me, well they're not really bothering me as much as I just want to talk about them."

Margie grabbed me by the elbow and asked if it had anything to do with my upcoming date with Tim.

"Yeah, it does. It has a lot to do with it," I said.

Margie bit her lip and asked, "Good or bad?"

"Good, I think, but its kind of confusing."

"Okay," Margie said. "I'm dying to know but I won't make you go through it twice. I suppose I can wait until Susan gets here."

My mother said that sounded like a good idea and reminded us that we had a lot of pictures to take.

*******

Susan arrived as we were just finishing up the photos. I was dressed in an outfit and was made-up to look around mid 30s. Mom said that we had enough pictures to make a small album. Of course it wasn't as easy as that. Some of photos were good as is but others would need a lot of photoshopping on my part. Mom said I needed to blend myself into the pictures from my dad's family. I also needed to scan the web for some more baby and toddler pictures.

******

We finished the photo session with me dressed as 46 year old Nancy. We took some solo pictures and some pictures of me with the other women. Afterwards, Margie led us to her kitchen and poured some coffee.

We were talking about my upcoming trip to Mexico when Margie reminded me of the "thing" I wanted to talk about. "Nancy said she wanted to talk to us about her date with Tim," Margie said. "Are you ready to talk about it now, Sweetie?"

The room grew quiet and three sets of eyes fixed themselves on me as they waited for me to say something.

I wasn't afraid of them because I knew they were on my side and I felt sure in my heart that I was doing the right thing. I also realized the anxiety I felt stemmed from the ending of one life and the beginning of another. There was no getting around the fact that I was about to betray myself but I was doing it for the woman I wanted to be for the rest of my life. I took a deep breath and exhaled the words I'd been afraid of for most of my life.

"I'm sexually attracted to men," I said. "Older men. Men like Tim Moreland."

All three women looked at me as if I'd lost my mind and wasted their time. Susan was the first to speak. "So what?" she asked as she shrugged her shoulders and lifted her hands in the air. "Did you think we didn't know that already?"

I swallowed my shame and fumbled with my cigarette case. "I guess you might have known but I didn't, at least not until yesterday," I said. "All this time, like my whole life, I've been telling myself that I wasn't gay and I was some kind of normal abnormal guy who liked to dress up in my mother's clothes and pretend he's a woman, not like that's really normal or anything, but that's what I was telling myself."

Susan smiled gently and laid her hand across mine. "I'm sorry Honey. I guess I just thought you knew that already were trying to put up some kind of a front."

"I was putting up a front," I said. "But I didn't know it. I never wanted to be gay and I still don't want to be, because its not who I was but I'm not that person any more." I covered my face with my hands and said, "God! I can't believe how crazy I sound."

My mother, who had already been enlightened, remained quiet and allowed Margie and Susan to ask the questions.

Margie asked, "So are you saying you've felt this way about men for a long time but you're only now admitting it to yourself and to us."

"Exactly," I said. "Its hard to explain. Its like some kind of hidden memory that finally sprung up and now I can remember it, but its like some crazy dream and I'm not sure its real."

"I can't really imagine what you're going through," Susan said. "However, I do know what its like to have weird and crazy dreams. Sometime I dream about leaving Rick and falling in love with a younger man. I mean I love Rick and everything, and I know I'd never leave him in real life…but the idea of making love to a younger man is so euphoric!"

"A younger man! Oh, wouldn't that be heavenly," Margie said. "Believe it or not, I used to think about you and I getting it on." She looked at my mother and said, "I'm
sorry Karen, but Darren was so hot as a boy."

Mom laughed and shook her head. "Don't worry. There's no reason to apologize, but I do think you and Susan raised an interesting point. And what I mean by that is... there's no law that says an unmarried 46 year old woman has to date men her own age. Nancy could be a cougar!"

Margie and Susan oohed and awed their approval. "You're mother is so right," Susan said. "You're too young to be saddled with an older man. I know you probably think its romantic and looks natural and I suppose it does, but if you do the math, I think you'll find 18 goes into 46 more times than 50 does."

Susan's mathematical equation supporting May-December relationships brought everyone to laughter except for myself.

"What's wrong, Honey? We're not embarrassing you, are we?" my mother asked.

"A little but not really. Its just that I know I said I'm attracted to men and everything but it only work that way for older men. I used to get grossed out whenever I took a shower with the guys after practice. If I was going to be attracted to younger guys, don't you think it would have happened then?" I asked.

Heads turned and nodded as the ladies mulled over the point I'd tried to make.

"So you're really only attracted to older men?" Margie asked.

"Definitely," I said.

"Seriously?" Susan asked.

I told them about the erections I'd get whenever I was around older men. "I didn't understand it back then but now it makes a lot of sense. I guess I've always liked older men."

"Well in that case, at least Tim Moreland looks hot for his age," Margie said.

I asked them if they thought Tim needed to take Viagra like the older men in the TV commercials.

"I don't know but I hope he's taking Viagra or something like it," Susan said, "because if he isn't then he should be. Sex isn't just for young people. Its an important part of a relationship at every age. And its especially going to be important to you. I know that when this is all over, you're going to look like a middle aged woman, but you're going to have the sex drive of a teenager. Unfortunately, an older man isn't going to feel the same way. His mind is going to wander off in different directions and its going to be up to you to get his attention and lead his mind back to the bedroom."

I asked how I was supposed to do that. "Should I just come out and say it?"

"Oh no! You should never do that," Margie said. "You'll give the poor man stage fright."

"So what are you saying?" I asked. "Do I just need to wait until he's in the mood."

Mom laughed and told me that I'd grow old and shrivel up if I waited for an older man to get in the mood. "You have to sneak up on him and plant the idea in his head," she said. "He needs to know you want him and find him attractive but you have to make him believe that sex is his idea. You have to make him want you?"

Susan chimed in by saying that men have fragile egos. "Its all about their penises," she said. "You have to continually assure them that its the most wonderful thing in the world or they'll lose their confidence. A man can't get hard unless he feels confident, even with Viagra. I know because its happened to Rick more times than he'd care to admit."

"Tim smokes. Doesn't he?" Margie asked.

I told her he smoked Winstons.

Margie bit her lip and said, "That's a good thing and a bad thing. It's good because he won't be turned off by your smoking. It's bad because smoking reduces blood flow to a man's penis."

"And that's what makes a man limp?" I asked.

"That and other things," Susan said. "A lot of men have to take blood pressure and cholesterol medicine when they get older. So if they smoke its like a double whammy."

Mom must have seen my perplexed look and tried to ease my mind by telling me I shouldn't worry about it. "It doesn't mean Tim won't be able to have intercourse with you, but it does mean you'll need to work at the relationship. Is there anything else that's bothering you?" she asked.

I took a puff from my cigarette and thought about it as I exhaled. "I'm worried about a lot of things, but I don't know where to start," I said. "Like right now I'm still trying to get used to the idea that I really do like men. I know that's a good thing but it makes me feel like everything else about me was a lie."

"Your life as a boy wasn't a lie," my mother said. "But your dream of being an older woman was more important to you than being a football star or growing up to be a man. It was just hard for you to admit it to yourself and to your father and I, but I'm glad you did."

"Are you really glad or are you just saying that to make me feel better about it?" I asked.

Mom shrugged and smiled. "I know I've flip-flopped a lot about this, but I've never backed down from supporting you. I want you to live happily ever after, but you have to admit, you're wanting to become an older woman is…well, its bizarre at best. But at the same time, I've never seen you happier than you are right now as Nancy, so I'd have to say I am genuinely glad about your becoming a woman."

I thanked her and told her how much it meant to me to hear her say that. "I couldn't do it without you," I said as I put my cigarette out. "And that goes for the two of you too," I said as I removed another cigarette from my case and lit it. "Sitting here and talking with all of you like this is a dream come true for me."

"You're on the way to becoming one of us," Susan said as she lit a cigarette for her self. "You're not a teenage boy any more. You're my friend and once you've finished getting all your surgeries, you'll be a 46 year old woman, complete with saggy boobs and a vagina."

"Just look at you," Margie said with exuberance. "Seeing you like this and hearing you talk about your feelings for men…well, its hard for me to believe there's really a boy underneath those clothes and that wig. You've matured so much and have become so feminine in such a short amount of time."

I beamed as I thanked her for being so kind.

"You're welcome," she said, "but I'm not being kind. I'm just speaking from my heart. Because you see, I've know you all your life but I've never seen you more comfortable and self-assured than you are now."

"I think you and Tim are going to have a wonderful time on your date," Susan said. "Where is he taking you?"

"We're going to see a movie and then he's taking to me that bar, Johnny's Hideaway," I said.

"Johnny's Hideaway? You know that's a pick-up bar for people our age, don't you?" Margie asked. "It's almost like they have a rule. No one under 40 allowed."

I told her I knew. "Talk about being in my element. It's going to be great!"

"What if he asks you to dance? Do you think you can do it?" Susan asked.

I told them that Mom had been helping me learn how to dance almost every night this week.

"Nancy is actually quite good," my mother said.

Margie asked if Tim was picking me up or meeting me at the movies.

I told her that he was picking me up around 6:30 at my house.

"That's good," Margie said. "That means he'll walk you to the door after you're date. And you know what that means, don't you?"

Everyone except me shouted that it would be my first kiss.

I blushed and told them I hoped so.

*****

Mom and I got home around seven. Dad had already made dinner for Sammy and himself but he had kept our dinner warm for us. He asked us how the photo shoot went and we filled him in on most but not all of the details.

As we were putting away the dishes, my father reminded me that my former football team was probably in the 1st quarter against Henderson.

"Henderson sucks. They'll win easy without me," I said as I lit a cigarette. I couldn't help but notice that he was staring at my cigarette and it made me self-conscious. Or maybe it was just in my head because we were talking about football and I was smoking.

"So you don't have any regrets about missing the game tonight?" he asked.

"What do you think?" I asked as I exhaled a stream of smoke away from him.

"I think you wouldn't be human if you didn't have some regrets," he said. "The real question is... are they bigger than you can handle?"

I told him that was a good way of saying it. "I really loved playing football but I can't look back now. I couldn't play even if I wanted to after what happened with Coach Holloway. Besides, I'm not even a student any more."

"Which is probably one more regret for you to size up," he said as he towel dried a plate and stowed it in the cabinet. "You're going to miss your senior year of high school and we both know you would have gotten a scholarship to play in college."

"I'm not going to tell you I don't think about those things, cause I do, but I had to make a choice and I did."

I paused to reflect as I took a puff from my cigarette. I pushed my glasses so that they were sitting properly and I smoothed out my skirt. I thought about my friends knocking heads on the field and all the noise from the crowd and the band. I lifted my cigarette for consideration and comparison. I thought about the silky panties and how they felt against my skin. I thought about what it might be like to kiss Tim the next night and then I said, "I think I made the right choice Dad."

My father smiled warmly and said, "I think you made the right choice too, Sweetheart. I'm really happy for you."

I kissed him on the cheek and thanked him. "I couldn't do this without you," I said.

*****

Later that night, I took my time getting ready for bed. After locking my door, I removed my cigarette case from my purse and stood in front of the full length mirror my father had bought for me.

I closed my eyes and thought about the future that wouldn't be. I didn't know the score but I was sure my team had beaten Henderson. I'd probably be in the shower right now or just getting out.

The week before there had been a few college coaches hanging around to congratulate me and some of my teammates as we were leaving the stadium. There would have been more coaches there tonight and I was sure they probably asked Coach Holloway why I didn't play.

I knew Coach Holloway would say the worst about me. He'd tell them I was a loser and that I lacked character. He'd tell them I had broken team rules by smoking cigarettes. And of course he'd tell them I dropped of school. However, he wouldn't tell them everything because he didn't know everything and for that I was grateful.

I opened my eyes and looked at the attractive older woman staring back at me from the mirror. Everything looked so perfect; the wig, the wrinkles, the glasses and skirt, and of course the cigarette. I placed it between my lips and lit it. I watched the smoke escaped down my throat only to return seconds later as a cone shaped cloud.

That was the look I loved! I looked and felt confident and sexy. Despite the hormones, my penis was erect and pushing out against my pleated skirt. I held the cigarette between my teeth as I used my hands to push up my saggy breast forms. Next week these will be real, I thought as smoke billowed from my nose.

I dropped my breasts and allowed my hands to follow down my sides until they were resting on my hips made wide from ample padding. My curvy figure was both womanly and matronly, which was a very sexy combination in my mind.

I look just like my mother, I thought as I puffed on the cigarette. And next week I'll be even more like her. After next week I'll never have to wear padding again or put on latex wrinkles. Of course I knew I'd be far from beautiful after the surgery. My skin would be red and seared and my body would feel as if a truck rolled over it, but that was the price to pay and I was more than willing to pay it.

The hardest part about dressing like a woman is not being able to prance when I feel like it. Real woman don't prance but boys who pretend to be women definitely prance, especially when there's a full length mirror in sight.

I flipped my head and batted my eyes while I smoked like a woman in front of the mirror. This is the life, I thought to myself, as I continued prancing and smoking. I felt so powerful and sophisticated as I blew smoke at my reflection.

I knew there was nothing rational or reasonable about the things I was doing and feeling, but I couldn't help my self. I also knew the feelings would end as soon as I masturbated myself so I took my time getting undressed and taking off my make-up.

I put on a long silk baby blue nightgown with white lace and had more cigarette in front of the mirror before taking off my wig. This is what Tim will see someday, I thought as I blew smoke at the mirror. "Do you think I'm sexy Tim?" I asked out loud. "Yes," I said as I answered for Tim. "You're the sexiest woman I've ever laid eyes on."

I lit a cigarette and propped myself up against two pillows and thought about Tim as I stroked my engorged penis. I imagined us dancing and him kissing me. I saw him across the table from me as he lit my cigarette and told me how beautiful I looked.

I wanted to imagine further but my body would have nothing to do with it. My penis rebelled and erupted sperm at least a foot into the air. I almost blacked out from the pleasure. I laid there on my back still smoking the cigarette dangling from my lips as a wave of shame and remorse overcame me.

I put the cigarette out and dried the sperm with a tissue. I felt dirty, vile, and disgusting. My low emotions were made worse by the coughing session that ensued. I must have smoked a half a pack from the time I locked the door. My lungs ached and my mouth tasted like a well used charcoal grill.

I shook my head in disgust and called myself a sissy faggot. I remembered what my father has said about being happy for me and I didn't believe him. How could he not see me for what I was, a faggot piece of shit.

I got up out of bed and pulled my nightgown over my head and threw it in the hamper. At least I was doing my own laundry now so Mom wouldn't see the stain.

I looked at myself in the mirror and saw the breast forms sagging from my chest. I tried to pull them off but couldn't so I got back in bed and cried myself to sleep.

******

I woke up Saturday morning with a hangover from the guilt and remorse that I'd felt the night before, but that did't keep me from lighting up a cigarette right away.

I didn't feel sexy and I didn't feel like a woman. I felt like a teenage boy with breast forms glued to his chest. I also felt like a nicotine addict and I grieved for the once strong body I had destroyed with cigarettes and female hormones.

How could yesterday and this morning be so different? Why were my emotions going up and down like a yo-yo?

The crazy thing was that I knew my feelings would change and then they'd change again at the drop of a hat or at the release of an orgasm. I couldn't back out now and I didn't want to back out. If I stayed a boy then I'd regret not becoming a woman. If I became a woman, I'd regret giving up my manhood. It was a no-win situation, but one situation was better than the other one and I knew which one it was.

I put out my cigarette and lit another one. The wig and the glasses beckoned me with their magic and their promises and I listened. I thought about yesterday at Margie's house and how I had felt so at ease around my mother and the other women. I had felt like one of them and that had felt extraordinary and wonderful. It was the feeling I'd been searching for my entire life and I wasn't willing to let it go.

I started thinking again with my woman brain. Nancy was back in charge and was pushing Darren out of the picture where he belonged.

I got up out of bed ready to start my day. First, I'd take a shower and shave my legs and under my arms. And then I'd prepare myself for my date with Tim Moreland. Poor Tim wouldn't know what hit him. I'd have him wrapped around my little finger in no time flat. And what would I do with him then? I smiled as I thought about the possibilities.

*********

I finished getting ready for my date with seven hours to spare. What was I going to do with myself for the next seven hours? Mom was as nervous as I was and we were both smoking like chimneys. Dad had voluntarily left the house to get out of our way, but Sammy didn't scare so easily.

My little brother's curiosity was like a double edged sword. I was thrilled he had accepted things for what they were, but his attention made me feel awkward and uncomfortable.

"Are you really going to go out on a date with Tyler's dad?" he asked.

"That's the plan," I said as I flipped though the pages of a Woman's Day magazine.

Sammy asked what I would do if Mr. Moreland tried to kiss me. "Are you going to punch him in the nose?"

Mom answered for me. "Of course not Sammy! Nancy wants Mr. Moreland to kiss him?"

Our mother's answer wasn't good enough for Sammy. He needed verification from me. "Don't you think that's kind of gross? You know with you really being a boy and everything."

I squirmed in my seat and reached for my cigarette case.

"You're really pretty when you smoke," Sammy said. "Do you like your cigarettes better than the kind Mom smokes?"

I lit my cigarette and told him I did. "I guess I'm just used to the menthol kind," I said.

"A lot of the girls at my school smoke menthols," Sammy said. "I guess its a girl thing."

Mom scowled. "Really Sammy. A lot of girls in your school smoke?"

"Just the cool girls," Sammy said.

I could tell Mom was disturbed but she chose not to make an issue out of it.

"Katie Rawlings has her parents permission to smoke," Sammy said. "She says her mom gives her a pack a day."

Mom rolled her eyes, "I hope this Katie doesn't smoke in school. If she does, she could get suspended if a teacher saw her."

Sammy shook his head no and said,"Katie's a nice girl. She'd never smoke in school. Her mom gives her nicotine gum."

"Well I suppose its not against the law, but 11 is very young to start smoking," my mother said.

Sammy asked her how old she was when she started smoking.

I knew the answer to Sammy's question but I wondered if our mother would answer him truthfully. "I was 11," she said, "but things were a lot different when I was a little girl. Everyone smoked."

"How old would I have to be if I wanted to start smoking in front of you and Dad the way Darren does?"

My mother and I answered him at the same with the same words. "Its bad and you should never start," we said.

Sammy seemed hurt.

Our mother apologized for yelling. "I shouldn't have screamed at you but Its a really bad habit, Sammy and I want you to promise me that you'll never start, but if you've already started then you need to tell me so I can help. Honey, have you been smoking Mommy's cigarettes?"

Sammy looked scared. "No, not any more," he said. "I've been smoking Nancy's. They're menthol and I like them better."

Mom and I both clutched at our hearts. "Oh no, Sweetie. You're too young to smoke!" my mother said.

"But you said it wasn't against the law," Sammy argued.

"Its not, as long as your father and I buy them for you like we do for Nancy. But this isn't about the legal thing. Its about your health. Look at what it did to your brother. He used to be such a good athlete before he started smoking. Nancy couldn't run a mile if she wanted to and the same goes for me. If you think smoking is going to make you tough then you're wrong. Tell me why you want to smoke, Honey?"

Tears welled up in my brother's eyes as the words spilled out of his mouth. "I don't want to be tough. I want to be popular and pretty like Katie."

"And Katie is popular because she smokes?" I asked.

Sammy wiped his eyes and said yes.

I asked him if he liked girls that smoked.

"No, but all my friends do. Especially Katie Rawlings. She's all they ever talk about it. They think she's so pretty and grown up because she smokes with her parent's permission. She even has a real cigarette case like you and Mom do. They're always talking about what it would probably be like to kiss her.

"I told Katie what they said about her and she laughed. She said that's why she started smoking in the first place, so boys would like her." He took a deep breath and dried his tears. "That's why I started smoking too, so boys would like me better."

I looked over at Mom to see if she was confused as I was and indeed she was. "What do you mean when you say you want boys to like you better?" I asked. "Are you talking about being better friends and being more popular or you talking about something else."

"I don't want to be their guy friend," Sammy said. "I want to be their girlfriend."

Mom and I both nodded calmly. "Are you trying to tell us you want to be a girl, Sammy?"

Sammy sniffed and wiped his nose. "Do you hate me?" he asked.

"Of course not Sammy! I could never hate you. Not in a million hears. You're my son and I love you."

"But I don't want to be your son. I want to be your daughter," Sammy said.

"Does anyone else know about this?" Mom asked.

"Katie does," Sammy said. "She's my best friend in the whole world so she won't tell anyone."

"I didn't know the two of you were so close," Mom said.

"I didn't tell you because I didn't think you'd want me being friends with a kid that smokes."

Mom lit a cigarette for her self and said, "Well, its not as if I think people that smoke are bad, but I have to admit its a bit different with children."

"Katie isn't bad. She and her family go to church every Sunday. We don't even do that."

I asked Sammy if Katie knew he was smoking.

"She gives me cigarettes some times. They're called Benson and Hedges and they taste like yours but yours are thinner."

"Sammy, when you smoke, do you inhale like Nancy and I do. You know, breathe it in."

"All the time," Sammy said. "I can even blow the smoke out my nose."

"When was the last time you had a cigarette?" Mom asked.

"A couple hours ago when I went outside."

Mom asked him if he smoked every day and Sammy admitted that he did.

"I can't believe what I'm hearing," Mom said. "When did you start? How long have you been smoking?"

"Since school started," Sammy said.

"You mean you started right after summer vacation?" I asked.

"Yeah, that's when I told Katie that I liked boys and that I wanted to be like her. She let me smoke a cigarette with her in the woods behind the school. And then she started giving me two every day so I could smoke at home. But it wasn't enough, so that's when I started smoking Mom's."

"And then when Nancy started smoking Virginia Slims, you started smoking hers. Didn't you?" Mom asked.

Sammy bowed his head and said he was sorry.

I was totally speechless. I had thought it was my fault that Sammy wanted to smoke and dress like a girl, but it wasn't. He'd been smoking longer than me, and him wanting to be a girl had nothing to do with me.

"Its okay, Honey," Mom said. "You don't need to be embarrassed about this. And for what it worth…well, I'm starting to think its probably not your fault anyway. Maybe this is just something that runs in our family like alcoholism or being bipolar."

Mom's kind words did little to soothe Sammy's pain and Mom looked to me for help but I just shrugged because I didn't want the responsibility. Here I was all excited about my first date with a man and my little brother was telling me that he wanted to be a girl and smoke cigarettes. Obviously I understood where he was coming from, and I didn't want to be a hypocrite, but why did it have to be now?

"Nancy, give Sammy a cigarette," Mom said.

Sammy's expression changed from upset to hopeful. "Really?" he asked. "You're really going to let me smoke."

The expression on Mom's face went blank as she spoke. "I'm not thinking that far ahead right now. I'm just letting you have one now because I think it would make you feel better and I need to think about it for a while. I'm not mad at you but I am really surprised. I never saw this coming."

"Me neither," I said as I handed Sammy my Louis Vuitton and stared at him as he removed a cigarette and lit it. True to his word, Sammy inhaled. He sucked the smoke deep down into his lungs and held it before letting it escape through his nose.

"Feeling better?" Mom asked.

Sammy nodded as he exhaled.

Mom sighed and said, "I can see you're hooked Sammy, but I don't want you to smoke and even if I did, I'd have to talk to your father before I could give you permission."

Sammy pleaded for Mom not to tell our father. "He doesn't need to know," Sammy said. "It could be our secret."

"I don't think so, Honey. These things you're telling me, the smoking and wanting to be a girl, well I'm not saying they make you a bad person. However, these things are big and important. They're not the kinds of things you can keep secret, especially from your father."

"Then why did you give me a cigarette?" Sammy asked.

"Because I love you and I thought you might need it," Mom said. "And I had to see you smoke so I could see if you were really addicted. I don't know, Baby. I guess I just thought it would help me figure out what to do about all this, but it didn't. I don't know what to do."

Our mother was clearly at a loss for words and decisions. I wanted to help. I need to help. I understood exactly what Sammy was going through, but I was struggling with my own identity. Was I my brother's 16 year old brother or was I his 46 year old adult aunt? Sammy needed for me to be an adult and stand up for him.

I couldn't beg or plead or whine the way Darren would have. I needed to make a statement and it had to come from a strong and confident woman.

Who was I kidding? I'm a kid- a teenage boy who wants to be a woman. Sammy wasn't my son. He wasn't even my nephew, but he needed me to a strong woman for him. Act the part, I thought. I'd been trying my best to act the part of an adult woman since this began for me. I wasn't Nancy Peterman. I was just acting like Nancy Peterman. So act some more! Act enough and maybe it won't be acting any more.

I straightened up in my seat and poked out my chest as I removed a long white cigarette from my case. In my mind I was making a statement about Nancy Peterman as I handled the cigarette and confidently placed it between my lips and lit it. Sure, it was only pretend confidence but it looked real.

Look at me, I thought. I'm not a silly teenage boy. I'm a woman and I'm smoking like one. I wrinkled my brow and exhaled to set the scene. Did I look strong, confident,thoughtful and wise? I hoped so.

"I don't think we should tell Dad until we know what we're dealing with," I said. "I know we need to address the smoking, at least eventually. However, right now, I think the most important thing is whether or not Sammy really wants to be a girl, or just wants to dress like one from time to time."

Sammy looked hopeful and Mom looked interested in what I was saying, so I continued. After all, I was on a roll. If only I could see my self in the mirror while I was talking and smoking like a woman who had it all going on. But I could imagine what I looked like and I liked the look.

"First of all, Sammy isn't going to stop smoking or wanting to be like a girl because we tell him he can't. I know he's only 11, but when it comes down to it…well, its his decision. He can keep doing these things and hiding them from us or he can fight the urges until he's older."

Mom interrupted me. "Or he can figure out on his own that its not what he wants."

"Exactly!" I said. "Kind of like with me, but we won't tell Dad unless we're sure." I looked over at Sammy and asked him what he thought about trying out being a girl to see if it fits."

Sammy seemed to realize the gravity of the situation. I could see it in his face. He was scared. I knew first hand how unnerving it was to get what you think you wanted.

"Its okay," I said. "Its not like I'm going to think any less of you if you put on a dress. As a matter of fact, I'd think more of you if you did it because its what you really want to do. It wasn't easy for me either, but it was worth it. I love looking like a woman and I'm going to love it even more after I get my surgery."

Sammy took a puff from his cigarette to steady his nerves and said, "But I tried yours and Mom's clothes on and they're too big for me."

Mom laughed and said, "Don't worry about that, Sweetheart. Our clothes are too old looking for you anyway. If you really want to do this then we'll help you do it right. Nancy and I will take you shopping for some clothes of your own."

I looked at the clock on the wall and made a suggestion. "I'm already dressed and ready for my date," I said. "I think we have time to go to Target."

"I think we have time too," Mom said.

"But what about Mr. Moreland? He can't see me dressed like a girl or he'll tell Tyler and Tyler will tell everyone else!"

"We can do it fast," Mom said. "You'll have plenty of time to change back into a boy before Mr. Moreland and your dad get home."

********

On the way to Target, Sammy opened up to Mom and I about wanting to be a girl and smoke. He had apparently felt that way for a long time. I looked over at Mom in time to catch her smiling as she pulled into the parking lot. "I know!" she said as she pulled into a parking space. "After we get home and get you dressed, we could call you Megan. What do you think, Honey? Do you like the name, Megan?"

"I know two Megans in my school," Sammy said. "They're both really pretty."

"Well, I'm sure that after we're done, you'll look just as pretty as both of them," Mom said. "Probably even prettier.

Sammy beamed and said he hoped so.

******

Our trip to Target was relatively fast. That's a nice thing about Target. All the things you need are usually in one place. We also saved a lot of time because Mom made all the choices without asking either of us for input.

Mom pushed the cart around her self, stopping here and browsing there. She said things like, you'll need this and that and this as she held whatever it was up to Sammy for an eyeball measurement.

It took less than 20 minutes to fill the cart with one outfit for Sammy. He had a pair of brown sandals, some panties, a slip, a padded braw, and a pink floral print dress. The dress and a long silky nightgown were the only things she allowed Sammy to pick out for himself.

*****

It was about 1:30 when we got back to the house. Dad wouldn't be home until five and Tim was picking me up at 6:30 so we had more than enough time to give Sammy a preview of how he'd look as a girl.

Sammy showed a range of emotions as Mom and I helped him get dressed. I saw fear and excitement splattered with shame and embarrassment. He fidgeted a bit as Mom applied the make-up. He acted a bit put out but we could tell he was trying his best to cover up his happiness.

The defining moment came as all three of us were admiring Sammy's reflection in the mirror. Mom asked, "Would you like to see how you look smoking a cigarette, young lady?"

Sammy's eyes widened and his jaw dropped. "Really? Can I?"

Mom smiled sadly and said, "If you're anything like your brother then I think I know how important it is to you." Mom turned toward me and said, "Nancy, I believe your niece has something she'd like to ask you." She put her hand on Sammy's shoulder and said, "Go ahead and ask her, Megan."

"Aunt Nancy. Can I try one of your cigarettes?" Sammy asked.

I handed Sammy my cigarette case and said, "Of course you can Megan."

Sammy shivered with anticipation as he fished a cigarette from the case and lit it. He watched himself in the mirror as he floated the cigarette beside his cheek and exhaled seductively. "I look beautiful," he said. "Thank you so much!"

A deep voice beckoned from the hallway. It was our father. "Sammy. Is that you?" he asked.

We all jumped but no one jumped higher than Sammy. And why shouldn't he jump? He'd been caught red handed in a dress.

Regardless of the way my father had been supporting me recently, it wasn't always that way. I wondered if seeing Sammy this way would be more than he could bare. The look on his face said he was more shocked than angry but anger could certainly follow.

It was Mom who spoke up for Sammy. "Don't be mad at him Bill. I'm the one who said he could do this."

My father kept his composure but he wasn't jumping for joy. He had embraced and supported my impending womanhood, but he had had years to deal with it. This was different. Seeing Sammy in a dress and smoking had blindsided him. My mom had claimed responsibility but I felt an equal share of blame.

Sammy had begun getting dressed without being asked, but my mother stopped him before he could his unzip his dress all the way down. He was upset and my father was upset and I felt their pain. I walked up to my father and took him by the elbow and asked if I could talk to him alone. He followed me down the hall to my room without speaking.

I closed the door and lit a cigarette. "Maybe you should sit down," I said as I pointed to the chair in front of my window. My father took a seat in front of the window and I sat down at my vanity and turned my chair so that we were facing each other.

I thanked him for not losing his temper. "I know that wasn't easy for you to see," I said.

He asked me how long the thing with Sammy had been going on. "Which part?" I asked. "The smoking or the dressing?"

"Both."

I repeated what Sammy had said to Mom and I.

"Is Sammy gay?"

"He's attracted to boys, if that's what you're asking. I get that you're upset but so is Sammy."

He told me it was more than upsetting. "I've already lost one son and now it looks like I'm about to lose another."

"It might not be like that," I said. "Maybe just needed to do it so he could find out he really didn't like it."

Dad shook his head and said, "I don't know about that, Honey. I mean, there's me and there's you and then there's Sammy. What makes you think he isn't like us? Seriously, he's almost 12 and what 12 year old in his right mind would let his mother and his brother or I guess, his aunt…What I'm saying is, it doesn't make sense for him to let you guys do that for him unless he really wanted it."

I took a puff from my cigarette and shrugged. "Maybe so," I said, "but that doesn't mean you have to think about it like that, at least not yet."

Dad squeezed his hands and sighed. "I don't know what to do," he said. "What do you think I should do?"

I told him that I thought that he should love Sammy unconditionally and make it easy on him either way. "I know you feel bad, but Sammy feels bad too," I said. "You know how embarrassing it was for him to get caught like that. He probably thinks you hate him right now."

"But I don't hate him. I'm just shocked."

"Then he needs to know that," I said.

"What about the rest?" he asked. "Should I try to act happy about it, like its no big deal?"

"Actually, I think you should, especially if you want the best for Sammy," I said. "Who knows, if you tell him its okay for him to get dressed up and smoke when he wants to, then maybe he won't want to do it any more and this whole thing will just go away. What would be wrong with that?"

"Nothing, but what if he doesn't want to stop doing it? What if he wants to dress like a girl and smoke all the time and be a woman like you?"

"First of all, he wouldn't be like me. I'm about to become a middle aged woman like Mom. If Sammy wants to be a girl then he'll be a girl and that means you'd have a daughter instead of a sister like me. Would having a daughter be so bad?"

"Of course not," my father said. "I would have been happy if either one of you had been born a girl. But you weren't, so this is going to take some time to get used to."

"So what do you think?" I asked. "Does this mean you'll be able to talk to Sammy and tell him everything is going to be okay, and tell him like you mean it so he'll believe you."

"I can do that," Dad said.

"I don't know if you noticed, but he looks very pretty as a girl," I said.

"I did notice. As a matter of fact, I didn't even think it was Sammy when I walked in on the three of you. I thought it was some teenage girl I didn't know that lived in the neighborhood. I just couldn't figure out what she was doing in my bedroom. And then when Sammy looked at me, I knew."

"He was so scared," I said.

"I guess this is probably going to be harder on him than it is on me," Dad said.

"It will be at first, but if you can make him feel okay about his self, then it will make everything so much easier for both of you."

"What's your gut feel about this?" Dad asked? "Do you think its a phase or something more serious?"

I took a pensive puff from my cigarette and exhaled. "I think Sammy probably wants to be a girl," I said.

"I think so too," my father said. "With everything we know about ourselves, I just don't see how it could be any other way."

I asked if he could be okay with that?

Dad smiled sadly and rolled his eyes. "Yes," he said. "I could be okay with having a daughter and I suppose your mother could too."

"That's for sure," I said. "Mom already has a name picked out for him."

"Let me guess. She wants to call him, Megan?"

I told my father that I thought it could be a good thing for both of them. "They need each other," I said. " and Mom's a good role model."

"I won't argue with you about your Mom," he said. "She's a good woman and a great role model, but so are you. I think its safe to say that you and your mother are the two most important women in Megan's life and she's going to aspire to be like both of you."

I thanked him for being such a great dad and for being so understanding as I crushed out my cigarette and picked up my Louis Vuitton case. I saw my dad take a lighter out of his pocket as I was removing a cigarette from my case. I placed the Virginia Slim between my lips and leaned forward to allow him the honor of being a gentleman.

I thanked him and exhaled away from his face.

"So are you looking forward to your date with Tim?" he asked.

I giggled and admitted that I was.

"Is that the outfit you're going to wear for your date?" he asked.

"Yes," I said as I straightened up in my chair. "What do you think? Is it too sexy for a first date? I love the way it shows off my curves, but it might be too young looking for what I'm going for."

Dad put the lighter back in his pocket and told me my dress looked perfect. "I know you want to look middle aged and you do, but don't kid yourself. People over 40 like to look sexy too and Tim is going to love you in it. Are you nervous about tonight?"

I laughed nervously as smoke spewed from my lips. "What do you think?" I asked. "I'm a 16 year old boy who's never kissed a boy in his life and now I'm about to spend a romantic evening with a man who is old enough to be my father."

"But you are looking forward to it. Aren't you?" he asked.

"Dad. I'm horny as hell! I don't know whether I should I should shake his hand or give him a blow job when he comes by to pick me up."

Dad smiled and blushed. "Why don't you try shaking his hand and letting him kiss you on the cheek if it comes to that," he said.

"I'm sorry if I grossed you out or embarrassed you," I said. "But it feels so good to finally be able to admit the way I feel about men. I used to be afraid to admit it to my self and now I'm admitting it to you. Its still awkward and everything but its liberating too."

My father stood up from his chair and said he was happy for me. I hugged him and said, "I've always dreamed about marrying a man like you and being a wife and a mother. You and Mom are so happy together and that's exactly how I want it to be with me and whoever I marry."

Dad took a step back and wiped a tear from his eye. "I guess we better check on Sammy and your mother," he said.

*****

Dad and I found Sammy and my mom downstairs in the living room. Sammy was still dressed as Megan and his eyes were puffy from crying. He looked as if his world had fallen apart and it had. I felt bad for him because I remembered that feeling. But I also felt good for him because I knew things were about to get better for him.

My father walked over to the couch and smiled knowingly at my mother before taking a knee in front of Sammy. I watched as he put his arms around Sammy and hugged him. I heard him say how much he loved him and that he'd keep on loving him no matter what. Sammy lifted his arms and draped them over our father's neck and then Dad kissed him on the cheek.

"I'm a lucky man," Dad said. "I had the honor and privilege of having two sons and now I have the joy and pleasure of having a sister and a new daughter. Unless of course you'd rather be my son."

Sammy looked up at him and sniffed. "I want to be a girl, Daddy. I want to be a girl all the time and I never want to be a boy again."

Dad bit his lip and scratched his head. "I'd like to help you out with that, but its going to take a little time, unless you want to tell all your friends that you want to be a girl."

"Tell my friends?" Sammy asked.

"Its either that or wait until we can sell the house and move."

"But we can't move! All my friends are here."

"Its up to you," Dad said, "but I'm going to be honest with you. I doubt your friends are going to like you if they find out you want to be girl."

"Katie would still be my friend," Sammy argued. "She wants me to be a girl."

Dad asked who Katie was and Mom answered him. "Katie is Katie Rawlings. She's the young lady who taught Sammy how to smoke like a girl. I've never met her either but I suppose that will change. Sammy is going to need a good friend if he's to become Megan."

Dad nodded and said, "Speaking of smoking, am I to understand we have another nicotine addict in the house?"

Mom spoke up in Sammy's defense. "Judging from what I saw and heard today, I think it would be pointless to make Sammy quit, especially if he's serious about becoming a girl. Sammy…Megan, thinks boys like girls that smoke."

Sammy blushed and looked down at his feet. Dad put his hand on Sammy's shoulder and said, "It's okay, Sweetheart. You don't have to be ashamed about it and you're right. A lot of boys do like girls that smoke, and I'm one of them. But on the other hand, a lot of boys don't feel the same way. So what I'm saying is, you can smoke, but don't think its going to make you popular with the boys. At your age, a lot of boys are intimidated by girls that smoke. And while I'm on the subject, a lot of parents think young children that smoke are bad kids. Even if you're friends accept you as a girl, their parent might not accept you as a smoker. Do you think you're prepared for that if it happens?"

"I don't want other kids or parents not to like me," Sammy said, "but if I'm going to be girl, then I want to smoke and I don't want to hide it."

"Fair enough," Dad said. "From now on, you have unrestricted permission to smoke."

"When you say unrestricted, does that mean I can smoke as much Mommy and Nancy?"

"I suppose it does," Dad said, "but you still have to follow the rules. So that means you can't smoke in school or wherever there's a no smoking sign."

"But I can smoke outside when I'm playing and in the house and every where else we go as long as its not against the rules?"

Dad nodded and said, yes. "So what kind of cigarettes do you smoke?"

"Any thing I can find, but I like menthol."

"Does that mean you want to smoke Virginia Slims like Nancy?" Dad asked.

"Her cigarettes are okay and I like them and everything, but if you're asking me, then I think I want to start smoking Camel No. 9 Menthol 100s Full Flavor. They're so pretty," Sammy said.

Dad smiled softly and said,"Wow, that's a long name. I hope I can remember it the next time I go to the store."

"They're black and green with a pink camel," Sammy said.

"And I'm sure you'll look very pretty and grown-up smoking them. What about a cigarette case? Do you want to use one like your mommy and Nancy?"

Sammy looked as if he was going to have an orgasm. "Really Daddy?" he asked.

"I don't see why not. Do you think you'd use one?"

"Oh Daddy! I promise I'll use it every day for the rest of my life!"

"I suspect you probably will," Dad said. "So would you like a cigarette now?"

"I don't know," Sammy said. "I think I'd feel a little weird smoking in front of you."

"Its only weird for a little while," I told him. "But you'll get used to it, so you might as well get it out of the way. Here," I said as I offered him my cigarette case. "Do you want one of mine."

Sammy shyly took the cigarette case from me and a lit a cigarette in front of the three of us. He blushed but his nervousness and embarrassment seemed to fade with each puff he took.

I watched him as he straightened up in his chair. A sense of pride and confidence came over him. My little brother was smoking like a woman- a young woman.

I was happy for him because I understood the things he was feeling about smoking and being female and even liking guys. But I was sad for him too because I knew he was romanticizing all of his feelings. Of course, who was I to talk. I was romanticizing my newfound femininity just as much if not more than he was. At least he'd still have his balls next week. Me, on the other hand, well I had drunk the Kool Aid and had gone back for seconds and thirds.

Here's to Kool Aid, I thought as I watched my little brother puff happily on the menthol cigarette I had given him. May you always be thirsty, Sammy.

The phone rang and my mother who was the closest to it, got up and answered it. She exchanged greetings with the person on the other end before holding the phone out to me. "Its for you, Nancy," she said. "Its Tim."

It was impossible to hide my excitement as I greedily took the phone from my mother. Tim, my boyfriend, was calling me.

"Hello Tim," I said with with a melodious jingle. "I was just sitting here thinking about you. You did say 6:30, right?"

There was a pause on the phone when there should have been anything other than silence.

"Yeah, about that," Tim said. "Something kind of big came up."

I asked if he was okay. "You didn't get into a car accident, did you?"

"No…nothing like that," Tim said. "It's about Tyler's Mom."

"Is she okay?" I asked.

"Yeah, Catherine is fine. Its just that she and I started talking and things kind of got complicated."

"She's not trying to get full custody of Tyler. Is she. Because if she is, then you need to see a lawyer because you're Tyler's father and you have rights."

"Look Nancy. I don't know how to say this because its not going to make a difference. You're going to hate me no matter what I say, so I'm just going to tell you what happened. Are you still there?"

I sighed into the phone. "Yes, I said. "Tell me what happened."

"Catherine and I decided to try to make things work between us, so that means I can't go out with you tonight."

I felt a tear run down my cheek and I swallowed to keep from bursting out into tears. I knew I should be happy for the guy. He was getting back together with his wife. If he loved her and she loved him then why shouldn't they and Tyler live happily ever after. But what about me?

"Nancy. Are you still there?" Tim asked.

"Yes, Tim. I'm still here. I'm sorry. It just caught me a little off guard, well very off guard, but I'm happy for you. This is a good thing for you and Tyler, right?"

"I think it is," Tim said, "but I sure feel like a heel right now."

"Don't…Don't feel bad about it Tim. I'm happy for you and I think its for the best. Does Catherine know about me?"

"As a matter of fact she does and she's quite jealous, especially after Tyler told her how pretty you are."

"Tyler is a sweet boy," I said. "Give him a hug for me."

"I will," Tim said. "And I hope this doesn't make things too awkward between us the next time we run into each other."

"Of course not. We were friends when we met and we're still friends as far as I'm concerned. Goodnight, Tim."

I handed the phone back to my mom and buried my face in my hands and sobbed. I should have been happy for him and maybe I was but I was upset for me. Maybe it was all the female hormones or maybe I was disappointed because I'd just been stood up. I didn't know. All I knew was that I felt depressed and hurt. I wanted to fall off the couch and lie on the floor.

Mom and Dad and Sammy tried to be supportive, but there was nothing they could say that would lift my spirits.

"He stood me up for his ex-wife," I said.

Mom put her hand on my shoulder and said, "I know this mist hurt, Honey. But its better that it happened now than when the two of you might have gotten serious about each other."

I closed my fingers around her hand. I wanted to say something encouraging but I couldn't. All I could do was cry.