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Like Mother Like Son

Author: 

  • Sharon Parsons

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Fiction
  • Posted by author(s)

Like Mother Like Son

Like Mother Like Son 1

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Caught with Consequences
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • Mother Envy
  • Adult Envy
  • Woman Envy

Permission: 

  • Posted by author(s)

Co-written by Victor G.
A special thanks to Victor G who co-wrote 'A Mother's Love' at Sapphire's site. Vic has a litterary way of making a boy look as if he walked out of the pages of a fashion magazine. He's a fantastic solo writer and I'm thrilled to have the opportunity to write this story with him. Now for a little info about the story.

Darren Peterman is a 16 year old high school football player who is at odds with his feminine side. As the title suggests, Darren's mother is his role model.

This story explores Darren's feelings as well as his family's as they struggle to define Darren's identity and gender. What would you think, do, and feel, if your parents told you they understood? Darren will try to answer those questions for himself and I suspect it will take more than a couple chapters.

******

I had just gotten home from football practice when my mother called me into the kitchen. My little brother Sammy sat on the couch watching TV. He was 11 and in the 6th grade, and like most young kids, he looked up to his older brother. I was his hero, and he gave me an enthusiastic high five as I walked past him.

"Hey bro. How was practice?" he asked.

I told him about a pretty spectacular - if I say so myself - catch I made in double coverage, then broke a tackle and sprinted down the field to score a touchdown. Sammy's eyes lit up as I described the play.

"Man, I can't wait until I get to high school and can play ball like you," Sammy said.

I roughed up his hair and punched him on the shoulder affectionately. "You'll get there, squirt. Don't be in such a hurry to grow up. In the meantime, how about we toss around the football after dinner?"

Sammy grinned at my suggestion. "Cool!" he said.

My mother yelled from the kitchen again. "Darren, are you coming? I really need to talk to you!"

"Yeah Mom, be right there. I was talking to Sammy."

I made my way to the kitchen and found my mother sitting at the nearby computer table. She was still wearing her office clothes, a very stylish burgundy suit and calf-length skirt ensemble she'd bought at Nordstrom's. Normally, she'd have changed out of her work clothes immediately, so whatever she had to talk to me about must have weighed heavily on her mind.

"So, what's up?" I asked, kissing her on the head in greeting, trying to assess the situation.

She paused a moment, gathering her thoughts before replying. "There's just some things I've been wanting to talk to you about," she said. She picked up her box of Marlboro Lights 100s, flipped open the top, and pulled out a cigarette. She put the cigarette to her mouth and lit it with the gold lighter my dad had gotten her for her birthday last year. She took a deep drag, exhaled, then spun around to face me.

"I don't know of any easy way to say this," she said hesitantly, "So I'll just spit it out."

The look on her face was pained and I was sure she was going to tell me something about my dad, like maybe the two of them were getting a divorce. I braced myself for the bad news.

"Is... everything okay with you Dad?" I asked.

Mom chuckled slightly and nodded. "Of course, honey. Your dad and I are fine. In fact, I thought about waiting for him to get home before I talked to you, but I think for now it's probably best to keep this between the two of us."

I was relieved my parents weren't getting getting a divorce but I had to admit my mother was beginning to make me nervous.

"Did I mess up or do something wrong?" I asked.

Mom's eyes softened and she shook her head. "Oh no, sweetheart," she replied gently. "It's nothing like that. You're not in any trouble if that's what you're worried about."

"Then what's the matter?" I asked.

My mother took a puff from her cigarette and inhaled deeply to steady herself. There was an odd look on her face, a mixture of concern, confusion, and love.

"Are you happy, Darren? Is anything bothering you? Anything you'd like to talk about at all?"

This was weird. What brought this on, I wondered. I shrugged, hoping to ease her worries. "I'm fine, Mom, why? Did you think I was getting bullied or something? I'm not the biggest guy on the team, but I am a football player. I can take care of myself."

She smiled gently. "No, of course not. I was thinking about something else and it's just a lot harder to talk about than I thought it would be."

I pulled over a chair from the dining room table and sat down next to her. I gripped her hand reassuringly.

"Well, if this is about drugs, then you and Dad can relax because I'm not taking them and I don't want to take them. I'm okay, really, and everything is fine."

My mother took a long drag on her cigarette and exhaled a thick cloud of smoke toward the ceiling. She stared at the lit end of her cigarette for a moment, then leveled her eyes at mine. "Darren, I really want to talk to you about this, but it's so hard to say. It's like the words are there but they're stuck in my throat."

I felt a surge of fear. Oh no, something's wrong. Mom's sick. I squeezed her hand a little tighter.

"Just say it, Mom," I whispered, preparing for the worst.

My mother looked at me with her confused, pained eyes and said, "Your father and I know that you're still dressing up in my clothes and that you want to be a woman."

I let go of her hand and sat back in my chair, stunned into silence. Mom took another deep drag on her cigarette and exhaled.

"There, I said it!" she said, sounding relieved. "Now it's out and we can talk about it."

I jumped to my feet and immediately denied her allegations. Purely out of instinct, because she was right and I was deeply ashamed. Yes, I had been wearing my mother's clothes, but I wasn't ready to admit to myself or anyone else that I really wanted to be a woman. Sure, I thought about it. As a matter of fact, I thought about it constantly, but I always wrote it off as some weird fantasy. Fantasies aren't supposed to come true. That's what makes them different than goals and aspirations. I certainly didn't aspire to be a woman. I was happy being a boy. I had a good life as a boy and I certainly wasn't gay.

No, I wasn't gay. I'd never been with another boy and didn't fantasize about being with other boys. However, I often fantasized about being a woman, and as that woman, I also fantasized about having sex a man. Passionate, amazing sex, where I was beautiful and alluring and he was a handsome, caring, well-endowed partner. I didn't think of that as being gay. It just meant that my two most detailed, erotic fantasies went together. Naturally, like peanut butter and jelly.

"I found some things on the computer, Darren," Mom said. "I also found that box in your closet."

I put on my poker face but I somehow knew my mother could see right through it. The box she was talking about had lingerie in it - my mother's lingerie, things she was going to throw out, but I had rescued and kept for myself. It also had some of her old women's magazines in it, ones containing articles that helped me learn some of the secrets of being a woman. Stuff like makeup tips and fashion advice, things I couldn't possibly learn as a teenaged football player.

The stuff on the computer could have been anything, there was a lot there that could incriminate me. I thought I'd covered my tracks, but I guess not. I'd looked at a lot of transsexual sites and had downloaded tons of pictures and stories - both real and fictitious - about men posing as or being turned into women.

I had even taken my fantasies out into the real world and had been posing as an older woman on an Internet dating site. I had doctored some photos of myself to appear as an attractive, middle-aged woman and had created an entire fake identity and history for "her." I had a few responses to my ad, and was communicating with a couple of handsome men while posing as this woman, but of course I hadn't met any of them in real life yet. So far, it was just innocent online flirting.

Any one of those things was bad enough, but combined together they were like a nuclear bomb. I told her I didn't know what she meant about the computer. "Maybe Sammy did it. He uses the computer too."

Mom crushed out her cigarette in the ashtray in frustration.

"Darren, I'm trying to be understanding about this so please don't lie. Not now. I know it was you. Or should I say 'Nancy Peterman'? Who is she?"

I groaned and slumped down into my chair. Nancy Peterman was the woman I was posing as on the dating site. "She's nobody," I said. "I just made her up."

"I know you did. But where did you get the pictures? Did you do your own make-up when you made those pictures?"

I told my mother about a website that morphed photographs. "I just uploaded some face shots of my self and typed in the age and gender I wanted to look like."

"They look very real. You make a very pretty woman," my mother said.

What was I supposed to do - thank her for the compliment? I wiped at my eyes and stared at the floor, unable to meet her gaze.

I felt as if the wind had been knocked out of me as my mother told me about the bookmarks she found. "I found the sites where you've been researching sex change surgeries," she said. "And the folders where you've been downloading pictures and stories. I found stories about boys who magically get turned into their mothers. I also found a bunch of pictures of older women."

All I could do was just stand there silently in shame. What was there to say?

Mom gently placed a finger under my chin and lifted it so that she could look me in the eye. We both had tears in our eyes as she spoke.

"Please explain something to me. The profile on your dating site says 'Nancy' is 46. Is that what you want? To be a middle-aged woman?"

Mom had found everything. The nuclear bomb had detonated in my face and destroyed my whole life. I couldn't make up some lie and explain it away because it wasn't the first time something like this had happened. I'd been dressing up in my mother's clothes for most of my life and I'd been caught more times than I can remember. Each time I got caught, I would swear up and down that it was the last time I'd do it and I'd get punished. In addition to the punishment, my parents let me know how disappointed and ashamed they were of me. I guess that was the worst part, dealing with the disappointment and shame. Not only from them, but from myself. But soon enough, I'd be back in my mother's clothes again, dreaming of being a woman, and again I'd get caught. And each time, I told her I was sorry and I wouldn't do it again, but I always came back for more. I couldn't help myself. No amount of punishment or verbal abuse or shame could keep me from exploring my fantasies and my mother's closet.

I just nodded silently, trying hard to keep the tears from flowing.

Mom smiled sadly and caressed my cheek lovingly. "I'm not mad at you, honey," she said. "And neither is your father. I didn't call you into the kitchen to embarrass you or punish you. I called you in here because I wanted to tell you that your father and I have talked about this and we don't want to make you stop. We tried that and it didn't work. And it will never work because you can't help yourself and we understand that now."

My mother sighed and lit another cigarette. "Your father and I want to help you, Darren. We know how much pain this is causing you and we want you to be happy. So we're going to help you become the woman you desperately want to be."

The bomb had blown up in my face and I wasn't dead but I wanted to die. Why was she saying these things to me? Did she expect me to be happy? I was so embarrassed and ashamed, it wanted to crawl under a rock and die. I pleaded with her to forget the whole thing and I told her that I didn't want to be a woman.

"But you do want to be a woman, Darren. You know it and your father and I know it and we've always known it - all of us have. We've just been in denial all this time. We tried to stop it from happening and that was wrong of us. Look at how unhappy it's making you!"

I shook my head in disbelief. "How can you say that?" I asked. "After everything you both said and did! How can you say it's all right now?"

"Your father and I went back and spoke to Dr. Girardi. Do you remember her?"

Of course I remembered her. She was the doctor my parents took me to see when I kept breaking my promises to stay out of my mother's closet. She specializes in gender disorders.

"We told her about your stuff on the computer. As a matter of fact, we even showed it to her. Your dad brought our computer to her office while you and Sammy were in school. She told us that what you've been going through isn't a phase and that we should help you. She even gave us the name of a doctor who can help with cosmetic surgery."

My hands instinctively went to cover my genitals. "You mean sex change surgery?"

"No, you're too young for that, but you could have cosmetic surgery on your face and give you breast implants. She can help you look like a woman. Except for your penis, but you can always hide that away."

"I don't understand, Mom. You want me to do this?"

"Only if you want it. In the meantime, to get you started living as a woman, Dr. Girardi said we should start you off by having you dress as a woman."

I grew excited at this prospect. "Yeah? How so?" I asked, my voice perking up.

My mother noticed the slight change in my demeanor and smiled. "Well, for starters, there's body padding to give you a more curvy, womanly body shape. And extensive make-up and a wig and some women's clothes. And later, if you want to go further, Dr. Lipscomb can do the cosmetic surgery to make things more permanent. The upside is that you wouldn't have to wait until you're 18. Dr. Lipscomb can do that anytime, but of course we're not pushing it that far just yet."

I was confused and intrigued at the same time. "So Dr. Girardi says I can look like a woman without getting any surgery, but I can still get the surgery if I try out the padding and the makeup and the clothes and I like it?"

"That's right," my mother said, "but it's not entirely simple. You have to be at least 18 before a doctor will make your penis into a vagina."

I had read extensively online about what it would take to turn me into a woman. But since I'd always wanted to be so much older, I never thought it would be possible. I nodded in understanding, and told my mother I had read about what was required for sex reassignment surgery.

Mom smiled gently in reply. "I thought so. Then you know that you have to live as a woman for at least a year before a doctor would even consider giving you total gender reassignment surgery."

I had been quite thorough in my research. I told her I knew that too.

"Okay then," my mother said. "That's why you might want to have Dr. Lipscomb do the cosmetic surgery next summer. You'll be 17 by then. Then you could have over a year of physically living as a woman before you turn 18. I think that would make it easier to get the remaining surgery then."

"So are you saying I should try out the body padding now, see what its like living as a woman until the summer and have the cosmetic surgery if I want it?"

"I think it would be a good idea," my mother said. "That way, if you decide being a woman really isn't what you want, you can just quit wearing the padding and the clothes. You'd have 7 months to decide if you want to get the breast and hip implants and facial surgery. Plus you'd have all that time to see what being a woman's really all about. It's not just clothes and hair and makeup. There's more to being a woman than just looking pretty."

"What about hormones?" I asked.

A serious expression crept over my mother's face. "Lets not get too far ahead of ourselves, but yes. Once you get into this, if you decided that you really want to be a woman, then it would definitely be in your best interest to begin female hormone therapy as soon as possible."

I was stunned and out of my mind with everything I had absorbed. "You're seriously giving me your permission to be a woman?" I asked.

"Yes, honey. That's what I'm saying."

"And Dad is okay with this?"

"He is, but he thought it would be better if I talked to you about it. I think it makes him a little uncomfortable. He's not sure what to say, even though he does want to help you."

"What about Sammy?" I asked.

"He doesn't know, so we'll have to tell him if you decide you want to do this."

"So this padding and make-up thing would only be temporary, right?" I asked. "I'd only wear it on the weekends and when I got home from school?"

"And school holidays, if you like."

"What about in the summer, if I get the cosmetic surgery? I can't go back to school with boobs."

"Your father and I were thinking you could get your G.E.D. instead of going back to school. It would be the same thing as a diploma and some colleges accept them if you want to go to college."

I tried to take it all in, wondering just what was in store for me. My mother could see how much I was taken in by it all. She took a drag on her cigarette and exhaled.

"So, what do you think? You don't have to make up your mind right now, but I am curious about your first impression."

My body tingled with anticipation as I tried to form my thoughts into words. The first thing I asked myself is if I wanted to do this. Of course the answer was yes! A thousand times yes! A part of me knew that I didn't have anything to lose because, apparently, I had my parent's support. But another, uncertain part of me said that I had everything to lose. And finally, I wasn't entirely sure if my mother and I were truly on the same page. I took a deep breath and held it until I was ready to speak. I wanted to make sure Mom knew exactly what it was that I wanted.

"Mom," I said carefully choosing each word that I said, making certain my meaning was clear, "When you're talking about helping me to be a woman, did you mean me being a teenage girl or an adult woman like you?"

My mother smiled and laughed. "Oh Darren, I'm not going to sit here and pretend I understand why you want to be a woman, much less a woman my age, but I'm not going to short-change your dream. I know exactly what you want. So yes honey, your father and I want to help you become a middle-aged woman. Is that what you wanted to hear me say?"

I was completely overwhelmed with joy and gratitude. I leaned over and hugged her tightly. "Yes, Mom! That's just what I wanted to hear you say! It's exactly what I want! I've dreamed about this for so long!"

Mom stroked my short, boyish hair reassuringly.

"I know it is, honey. I've already talked to Brenda at my salon and she said she'd be thrilled to help us in any way she can. I showed her your school pictures and the ones from your dating site. She said that it wouldn't be any problem at all for her to make you look as if you're at least 45 years old and match the woman in the pictures. she also said that with your facial features, you'll make a gorgeous older woman."

I tried to subdue my enthusiasm, not wanting Mom to know how eager I was to stop being Darren - her son - for a while, but inside I was totally thrilled. My hands trembled with excitement at the thought of looking like a gorgeous older woman. Not only looking like one, but getting to live as one as well.

This is really happening, I thought. Nancy Peterman is really going to come to life, and I'm going to get to be her! I thought about the stylish outfits I'd get to wear, of having flawless makeup and hair (even if it would be a wig). I realized I'd get to go out in public as the attractive, mature Nancy, with no one knowing I was really a plain, unassuming teenaged boy.

I thought about how'd I'd look and act as an adult woman, what habits Nancy might have that Darren didn't. Since she was 46, Nancy would have an array of adult habits. Some good, some bad. She could easily drink and even smoke, and no one would condemn her the way they would Darren for doing the same.

And... dates! "Nancy" could finally get to go out on dates! With a handsome man treating me like a lady, holding open doors for me, telling me I'm beautiful, maybe even kissing me... The idea of dating men both repulsed and excited me. It was wrong and went against my nature, but the thought of a man being attentive to me was very alluring. I knew in my heart that I'd never go past first base with a man, but getting there could be fun. What was first base- holding hands? Flirting? Maybe a little kissing?

"Darren," Mom said, snapping me out of my reverie. Fortunately, she didn't notice the sizable erection that had appeared in my jeans. I sat down quickly so she didn't notice.

"There's something very important that you need to understand," she continued, "There's much, much more to being a middle-aged woman than just wearing a dress and having boobs and wrinkles. You're going to need to learn how to dress and act the part if you expect to live a happy and fulfilling life as a woman."

"You can teach me. Can't you, Mom?" I asked excitedly.

My mother leaned over and kissed me on the cheek. I could smell her expensive perfume and makeup mixed in with a faint whiff of her cigarette smoke. It smelled like a classy, sophisticated adult woman, and I couldn't wait to smell like that.

"Of course I will," Mom replied, wiping a faint lipstick mark from my cheek. "I'll help you with everything you need to know to become 'Nancy' in real life. How to move like a woman, how to talk like a woman, how to pick out a smart outfit. Things a woman Nancy's age should know. It's going to be a lot of work. Think you're up for it?"

I grinned. "Of course, Mom! I can't wait to get started!"

"Then lets start by telling Sammy. Just be honest with him, he'll understand. Then you can study up with my Woman's Day and Ladies Home Journal magazines. I have plenty of back copies to keep you busy."

The idea of reading my mother's women's magazines without fear of retribution thrilled me beyond explanation.

"In the meantime, I'll make an appointment for you with Brenda at the salon on Saturday. Tomorrow, while you're at school, I'll buy you some clothes to wear to the appointment. Afterwards, we can spend the whole day shopping. You're going to need a new wardrobe. We'll make it a girls' day out!"

I started crying again because I was so happy. I thanked her again and again and told her it was the best day of my life.

Like Mother Like Son 2

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Caught with Consequences
  • Sweet / Sentimental

Other Keywords: 

  • Mother Envy
  • Mature Woman

Permission: 

  • Posted by author(s)

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.

Like Mother Like Son 3

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Caught with Consequences
  • Sweet / Sentimental

TG Elements: 

  • Panties / Girdles
  • Smoking Fetish

Other Keywords: 

  • Mother Envy
  • Older Woman
  • Middle Age

Permission: 

  • Posted by author(s)

16 year old Darren Peterman comes home from school to find his mother has bought him a new outfit, befitting of a middle aged woman. Can he face his father and little brother for the first time in a dress?

*******
Chapter 3
*******

I found it hard to concentrate in school because I couldn't stop thinking about my mother and what she might be buying for me. I knew it would need to be enough for me to wear to the salon on Saturday. And after that, she said we were going shopping for some more clothes. I thought about the old phrase that says you have to have money to make money. It was kind of like that with women's clothes. I need to dress like a woman in order to buy women's clothes. I was very cool with that.

Whenever I wasn't thinking about my mother and her purchases, I was checking out the girls in my classes. Looking at girls wasn't a new thing for me, but now I was almost studying them. Because they were born as females, becoming women would be easy for them. It would be second nature, something they didn't think about, the way I never gave much thought to becoming a man.

I compared their mannerisms to my mother and her friends. It was very similar in that they moved their hands around the same way when they talked, but teenage girls are much more giggly than older women. I didn't want to be giggly. I also didn't want to wear the kinds of jeans and tops they wore. Their clothes were trendy and I suppose there's nothing wrong with that, but the older women I knew wouldn't be caught dead wearing such things. I hoped my mom would buy me a nice wool skirt and a sweater top or maybe even a pant suit.

********

My coach yelled at me a lot during football practice. He said my head wasn't in the game and he was right. Until today I had loved going to football practice and cracking helmets with my teammates, but now it didn't seem the same. I kept thinking there were so many other things I could be doing, like playing Bridge with my mom and her friends.

Tonight when I got home, my mom would have some new clothes for me. Tomorrow night our team would play at home against Wesley High School. Just last week my coach had taken me aside and told me there'd be some college scouts at the game. Even though I was only a junior they were interested in keeping tabs on me. I remember being so excited when he told me that, but at the moment I couldn't care less.

The next seven months were supposed to be a dry run for when I got my own boobs in the summer. I was supposed to use the time to decide whether or not it was how I wanted to live my life for real. Even though I'd never worn a dress in public, I knew in my heart that regardless of how things played out, there would never be a time in my life when I didn't want to wear women's clothes. So why should I waste my time going back and forth between boy and woman?

Thoughts of female hormones loomed large in my head. My mother had talked about the possibility of my starting female hormone replacement therapy even before summer. She knew as well as I did that the longer I delayed taking them the more masculine I would look in later years. Did I really want to risk that? I didn't think so.

My dad warned me not to rush into things. He couldn't comprehend my feelings but I think he could tell I was thinking with my dick. Don't let your dick make an appointment that your ass can't keep. Speaking of my dick, I haven't given a lot of thought to what I'm going to do about sex once I become a woman.

I was well aware of the effects female hormones has on penis size. I'd read a lot about it on the web, even though I never had any intentions of taking them. I knew that transexuals could still get erect with the help of Viagra, but what would I do as a woman with a stiff dick?

I considered my options. I could become a limp dick lesbian or I could beat my soft meat to climax, or I could take up sex with men and let them take me in the ass. Out of those three options, masturbation seemed like the only one I could live with. It wasn't as if I didn't enjoy having sex with girls, because I definitely did enjoy it. But being a woman seemed to take precedence over sex. I honestly thought masturbation would be enough for me.

I left the stadium and drove home. The anticipation was killing me. What had my mother bought? How much of a woman was I going to be tonight? And still, I wasn't convinced that I was doing it for the right reasons or if it would even be in my best interest. All I knew was that I wanted womanhood and damn the reasons for wanting it. I just wanted it to happen and I'd deal with the consequences later.

******

My mother was waiting for me when I came home. She was every bit as excited as I was. There were several bags and boxes sitting on the couch and on the coffee table. She told me that Dad had taken Sammy to dinner and to see a movie. She told me that we had the house to ourselves. I was elated.

I usually shower after practice in the locker room, but I had decided against it due to my lack of body hair. I knew I could handle a little ribbing from the guys and eventually it would probably happen, but I was stressed enough without putting more on the plate. My mom gave me a pair of panties and told me to put them on after I took a shower. "Hurry," she said. She didn't have to tell me twice.

Although I probably didn't need to shave again, I did it anyway. I wanted to look good but I also wanted the clothes to feel good on me. After drying off, I stepped into the pair of silk panties and pulled them up to my waist. The silk felt heavenly against my erect penis, but I did my best to think my erection away. I think that was the first time I realized that my penis was going to get in the way and it made me want to start female hormone therapy that much more.

The panties were exactly the kind I wanted. I knew from looking at pictures on the internet that panties came in a lot of shapes and sizes. I think a lot of guys think skimpy thong panties are sexy, but those are for young girls with slender bodies. The panties I was wearing were made for women with big bottoms. I wrapped a towel around myself and went downstairs to meet my mother.

My mom was waiting for me in the living room. She looked excited as she stood with her hands on her hips and a lit cigarette between her fingers. She was wearing a knee-length gray wool skirt with a blue v-neck sweater. The string of peals which had become a part of her daily ensemble years ago graced her neck. Her eyes danced behind her glasses and her highlighted hair swung as she asked what took me so long.

"I wanted to shave my legs again." I said.

"Well I hope you did under your arms too," she said as she took the lid off a box and removed a single large breast form. "I guess you know what this is. Don't you?" she asked.

"Its so big!" I said.

"It fits a D cup, the same size as mine," she said. "Now you'll know why I'm always complaining about my back."

I pinched it with my fingers and laughed. "I won't be complaining," I said.

My mother told me to lose the towel so that she could put some glue on my chest. It felt cold and sticky. I told her about the stories I read about breast forms sticking too well. "Will I be able to get these off before I go to school tomorrow."

"Don't worry about it," she said as she positioned the right boob in place. "We're not using super-glue. It should come off fairly easily in the shower."

"So I'm not going to be able to take them off before Dad and Sammy get home?" I asked.

"You could, but why would you want to?" my mother asked as she positioned the left boob in place. "Now comes the bra," she said as she pulled one out of a shopping bag. I watched as she adjusted the straps so that it wouldn't cut into my shoulders. She handed it to me and I put it on by hooking the clasps in the front and rotating it before slipping my arms into the straps.

"Are you ready for a bigger ass and hips?" she asked as she showed me a padded girdle.

"Its like the girdle pad I wear for football," I said as I took it from my mom and stepped into it.

"I suppose it is," my mother said. "But I wouldn't wear it in the game tomorrow. You're going to love this," she said as she pulled a top and a skirt out from another bag. The top was gold with black print and buttoned up from the front. The skirt was black polyester. "You'll need to wear nylons when we go out on Saturday." She laid them on the couch and gave me a black half-slip that she'd gotten from another bag.

I pulled the slip up over my padded girdle and my mom helped me with the zipper on the skirt. As I was buttoning up the gold top, my mother took a pair of black sandals from a shoe box and put them on the coffee table.

"Don't get to used to sandals," she said, "because I'd rather you wear heels. We'll get you some on Saturday. You'll need to practice walking on them but you'll love them because they'll make your legs look longer and slimmer."

I suspected that the next thing my mother had for me was a wig and I was right. It was ash blonde and looked like it would hang past my shoulders. I couldn't wait for my mother to get it on my head.

My mother told me it was made from human hair and that Brenda could put some highlights on it when we went to the salon. "Last but not least," I got you some glasses," she said as she placed them on the bridge of my nose.

I was afraid they'd make everything blurry but they didn't change a thing. My mother told me they were just for show and not prescription lenses. "They're for women who can still see but want to look smarter," she said.

I didn't know what I looked like but I sure felt feminine. "Can I look in a mirror?" I asked.

"Sure you can, but lets go upstairs and put a little make-up on you. I'm sure Brenda will give us something different to help you look older, but I can get you started. Would you like that."

"You know I would," I said excitedly as I grabbed her arm.

My mom led me up stairs to her bathroom and had me sit down in front of her mirror. I watched her in the mirror as she removed a cigarette from her Louis Vouitton case and lit it. I had watched my mother put on her make-up at least a thousand times or more and each time she did she always smoked, so I wasn't surprised she felt the need to smoke while she helped me with my make-up.

The night before, my mother had confessed her excitement over feminizing me, and judging by the look on her face, she hadn't been exaggerating. I don't think I'd ever seen my mother any happier than she was at that moment.

She explained what she was doing with the brushes and why she was doing it. She even had me try my hand at repeating the steps. I had never tried to use make-up in the past because I'd been intimidated by it, but my mother showed me that it was an art and not rocket science.

The smoke from her cigarette drifted toward my face and my mother waved it away with her hand and apologized. I told her it was okay and that I didn't mind because I really didn't. As a matter of fact, I wished I was smoking with her. Of course I didn't tell her that because I didn't think she'd take it very well.

Even though she smoked, my mother was a bit of an anti. She had always preached to my brother and I about never starting. I had confessed a lot of embarrassing things to my mother over the past 48 hours, but wanting to smoke like her wasn't one of them. I kept those thoughts and feelings to myself because I didn't want to rock the boat and upset her.

I had fantasized about being a smoker for as long as I had fantasized about being an older the woman. The two things went together for me and I could never separate them.

The funny thing is that even thought I thought about smoking all the time, I'd never been brave enough to try it because I was afraid of getting caught, that and I didn't think it looked right for guys to smoke. I probably feel that way because my dad doesn't smoke. Its always been a woman thing to me.

After my mother finished putting on my lipstick, she placed her hands on top of my shoulder and admired her work. "What do you think?" she asked. "You don't look my age but you look like a woman and a very pretty woman at that! Don't you think?"

My mother was right. I did look good, but I wasn't surprised because I'd been there for the total transformation. I just hadn't said anything about it until now. I told her I loved it. "I can't believe its really me," I said. "I don't even recognize me. I look like I'm in my thirties."

"I can't wait for your father and brother to see you like this" she said. "Are you scared?"

I wanted to bite my lip but I refrained because of the lipstick. I was almost afraid to move for fear that I'd mess up my mother's work. I told her I was scared to death.

My mother suggested that we go down stairs and have a glass of wine. "I don't want you to get the wrong idea about drinking," she said, "or make a habit of it. But I think it will help you relax."

"That sound like a good idea," I said as I got up from the mirror and followed my mother downstairs.

We went into the kitchen and I got two glasses out of the cabinet while my mother took a bottle of open wine from the fridge. She poured our wine and we took it into the living room.

I watched my mother as she lit a cigarette and forced myself to say something about it. "Is smoking good for relaxing too?" I asked as I took a sip of wine.

My mother frowned as she exhaled and said, "Yes it is. Its very relaxing, but it will kill you, but you don't have to worry about that because I'll kill you first if I ever catch you doing it."

That wasn't the reaction I was hoping for but at least she didn't sound mad at me for asking so I decided to try another question. "How old were you when you started?"

My mother groaned and shook her head. "I'm embarrassed to tell you this, but I started smoking when I was 11. However, I didn't smoke in public until I turned 14. That's when my parent's gave me their permission. I know that sounds young, but you have to understand that back then, everybody smoked. My high school even had a designated smoking area for the students. It wasn't like it is today."

I was blown away by her answer but I did my best to keep a poker face. I couldn't believe she was actually talking to me about it and being so casual. It made me wish I had asked her sooner. "If you don't mind me asking, didn't you know it was bad for you health back then."

"I did but I was in a hurry to grow up, kind of like you are," she said. "Isn't that why we're having this conversation, because you're thinking about taking up smoking?"

I told her that I didn't know what she was talking about, but the heat from my face and the stutter in my voice betrayed me.

She grabbed my hand and told me it was okay. "You don't have to be embarrassed," she said. "I'd be worried if you weren't thinking about things like smoking, and drinking, and sex. That's why we need to talk so that I can help you figure things out."

My mother hadn't set a trap for me and she wasn't angry. I was relieved but I was far from calm. "I guess I'm still trying to figure out the rules," I said.

Mom laughed and said, "Good luck with that. This isn't like football or having curfews," she said. "There aren't any rules when it comes to being an adult woman. Its all about the decisions we make. Some are better than others and they all have consequences." She took a sip of wine and asked if liked it.

"Its good," I said. "Kind of sweet."

"You know deciding whether to drink or not is one of those decisions you'll have to make. That's one of the reasons I offered you a glass."

"What? "Was it some kind of a test?"

Mom shook her head. "No Honey. Not at all. I know your father and I have had talks with you before about drinking, smoking, sex, and drugs, but those talks were meant for a teenage boy- not a middle aged woman."

"So does this mean I can make my own decisions from now on?" I asked.

"I suppose it does, but I'll still give you my two cents whether you ask for it or not. I can tell you right now that I'm not going to agree with every decision you make, but I'll try my best to understand and respect it. So what do you think? Do we have a deal?"

I nodded and wiped a tear from my eye. "Thank you," I said.

"So what kind of decisions are you working on right now" my mother asked.

"I shrugged my shoulders because I didn't want to say it.

Mom sighed and said, "If I had to guess, I'd say you were thinking about taking up smoking. Am I right?"

I answered her by nodding shamefully.

"Does this have anything to do with your becoming a woman?" she asked.

I cleared my throat and caught my breath. "Yes," I said.

"Is that why you asked if smoking was good for relaxing?" she asked. "Because if you're nervous about the transition, we could ask the doctor to prescribe a mild tranquilizer for you. That would be a healthier alternative to taking up smoking."

"Look Mom, this isn't about healthier alternatives," I said. "This is about me gaining confidence as a woman and feeling good about myself. Pills and wine can't do that for me," I said as I hoisted my glass, "but cigarettes can."

"I don't understand Darren. Where did you get this idea that smoking will give you more confidence?" my mother asked.

"From watching you," I said. "When you walk into a room and light a cigarette, you look so strong and powerful, like you could take on the world and win. But at the same time you're sweet and feminine, the way a mom and a wife should be. I've wanted to be that kind of woman all my life. That's why I need to smoke so I can be like you."

"I don't know what to say. I never knew you felt that way."

"So its okay with you if I start smoking?" I asked.

"I didn't say that. You're only 16," my mother said.

"But I'm about to be a 46 year old woman," I countered.

"Look Darren. I'm flattered to know you think so highly of me, but instead of being a carbon copy of me, shouldn't you be your own woman?"

Before I could answer her, the front door pushed open and my dad and brother walked in.

The logical part of my brain assured me that everything was going to be okay. My father had announced his support and we had already broken the news to Sammy. In some ways, them seeing me dressed as a woman was a period at the end of a sentence that had already been spoken.

However, there was another part of my brain that wasn't so logical. I was a scared 16 year old boy who was on the verge of humiliating himself in front of the little brother who used to look up to him and the father who had wanted a son he could be proud of.

It felt like another walk to the electric chair. How many times would my pride have to be executed?

"Hold your head up high and don't slouch," my mother said as we stood to our feet.

On any other night my mother would have asked Dad and Sammy how the movie was or what they had for dinner. But this wasn't like any other night. She stepped out of the way so that I was in full view of Sammy and my dad. I saw her arms swing sideways as if she was presenting me, which was exactly what she was doing. "So what do think?" my mother asked. "This is Nancy Peterman."

So there I stood in front of my gawking father and brother. I didn't feel like a beautiful woman. I felt like a scared boy who had just gotten caught wearing his mother's clothes. But the clothes I was wearing were mine. They belonged to me. My mother had bought them for me, and in some ways, that made it that much worse.

My father was the first to speak. "You look gorgeous Darren."

"I think it would probably be best if we called him Nancy when he's in woman mode," my mother said.

Dad shook his head and mumbled something about my mother being right. "I'm sorry," he said. "Its just a lot to take in. I thought I'd know what to expect but you look so much better than I thought you would. You really are beautiful Honey."

"Thanks Dad," I said sheepishly.

"You know I've been thinking about this," my mother said. "And its definitely not a good idea for you to call your father Dad when you're dressed like this in public. Its fine for right now when we're home, but we should probably tell people that you are your father's sister and that would make you Sammy's aunt."

"I think your mother is right," my father said. "You should probably call me Bill when we're out in public."

"And I should call him Aunt Nancy?" Sammy asked.

My father squeezed Sammy's shoulder and told him he was right.

"You're not going to go to school tomorrow like that. Are you?" Sammy asked.

"No Honey," my mother said. "Your Aunt Nancy is going to be your brother Darren tomorrow morning. I know this has to be confusing for you because its confusing for your father and I, but it will get easier for all of us in time. And when summer get here, your brother will be gone forever."

"So he's going to be a real woman like you for the rest of his life?" Sammy asked.

"That's right Honey. Just like me forever and forever," my mother said.

My mother's words hit me hard and I felt as if I was going to pass out so I took a seat on the couch before I could fall. Oh my God, I thought. What have I done?

Like Mother Like Son 4

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Caught with Consequences
  • Sweet / Sentimental

Other Keywords: 

  • Mother Envy
  • Older Woman Admiration

Permission: 

  • Posted by author(s)

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?

************
Chapter 4
************

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.

Like Mother Like Son 5

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Caught with Consequences
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • Hair Salon / Long Hair / Wigs / Rollers
  • Smoking Fetish

Other Keywords: 

  • Mother Envy
  • Older Woman Obsession

Permission: 

  • Posted by author(s)

Edited by Victor G.
16 year old Darren Peterman visits a salon as Nancy for an adult make-over and takes up smoking.

******
Chapter 5
*******

I woke up on Saturday morning in a state of frightened ecstasy. My mother was taking me to the salon this morning to meet Brenda. Today was the day that Brenda would make me look like a 46-year-old woman! And today was the day my mother would take me shopping.

Did I really have the courage to go out into public dressed like a woman? I thought about that as I took my shower. What if someone recognized me? What if the women in the salon figure out I'm a boy? Would they laugh at me? Would the kids at school find out?

My mother was waiting for me when I got out of the shower. "Are you as excited as I am?" she asked.

"Oh my God," I said. "I can't believe we're doing this."

"You don't want to back out. Do you?" she asked. "Because you can if you want to, I'll understand if you change your mind and so will Brenda."

"No way," I said exuberantly. "I'm scared as hell, but I'm ready and I want to do this. Do you really think Brenda can make me look older?"

"Of course she can," my mother said with confidence. "She used to work in Hollywood before she opened her salon. We're going to look like sisters when she's done with you."

Mom told me to come find her after I finished getting dressed. She said she would help me with my make-up and afterwards she had a surprise for me. "Did you get me some dangly ear rings?" I asked.

Mom smiled and raised one of her eyebrows. "I can't tell you," she said. "Its a surprise. Now hurry up and get dressed!"

I put on the same outfit I had worn when my mother introduced "Nancy" to Dad and Sammy. It was the only outfit I had, but after today I'd have more clothes to put in my closet. After securing my wig to my head, I walked out into the hallway and called for my mom.

Mom met me in her bathroom and had me sit down in front of her mirror for another make-over, but this time she made me do my own make-up while she gave me verbal instructions.

I was nervous because I didn't want to look like a clown, but Mom reminded me that Brenda was going to do re-do it at the salon. "This is just so you can walk through the front door," she said. "And when you walk out the door, you'll look thirty years older!"

I did a pretty good job with my make-up, but my mom had to come to my rescue a couple of times. "It's like sports," my mother said. "You'll get better with practice," she said as she put the top back on the lipstick. "So are you ready for your surprise?"

"This feels like Christmas, except better," I said as I followed my mother into her bedroom.

I stood by the bed as mom retrieved a Neiman Marcus shopping bag from her closet. "Neiman Marcus!" I said. "It has to be expensive. I hope you didn't spend too much."

Mom sighed and said, "Tell me about it. Your father had a cow when I told him how much it cost. I had to tell him that I was paying for it out of your college fund. So here's a part of your college," she said as she handed me the bag.

I could tell it was a purse as I was pulling it out of the bag but my heart stopped when I recognized the brown and tan checks. "Its a Louis Vouitton" I screamed. "But it's different than yours."

"Remember what I said about you being your own woman?" she asked. "I wanted you to have the best but I wanted it to be different than mine. Yours is from the Damier Ebene collection."

"Its so big," I said as I spun it by its leather handles.

"It has to be," my mother said. "As a woman, you'll need to carry around a lot of stuff and I took the liberty of starting you off with some things you'll need. Go ahead. Look inside."

I unzipped the bag and looked inside. I saw lots of things that a woman would need in her purse like a compact and lipstick and vials of nail polish and nail polish remover. However, my brain pushed all those other things aside and focused on the two other Louis Vouitton pieces. I pulled out the biggest one first. "Its a wallet," I said excitedly.

"What about the other one?" my mother asked. "You know what it is. Don't you?"

I held my breath and bit my lip as I reached in and pulled the Louis Vouitton treasure from the purse. "It's a cigarette case," I said, "and its beautiful!"

I was too stunned to say anything else. The tingling in my groin changed to a burn and made my knees buckle. I could tell from the feel of the case that there was something inside it. I removed the canvas flap from its tab and looked. An open pack of Virginia Slims Menthols peeked up at me. "Are these really for me?" I asked.

"I hope you like menthol," she said, "because I put the rest of your carton next to mine in the cupboard."

With my cigarette case held tightly in hand, I wrapped my arms around my mother and kissed her on the cheek. "Thank you, Mom! Thank you so much," I said. "You don't know how much this means to me."

"I don't know if I'd say that," my mother said. "You did a pretty good job of explaining what it would mean to you the other night. But just so you know, the official story is that you've started smoking to deal with the stress of going through the changes. That's what I told your father and that's what you're going to tell anyone else who asks."

"How did Dad take it when you told him?" I asked.

"He took the news surprisingly well, a lot better than I thought he would. Your dad isn't as big of an anti-smoker when it comes to women. He understands your days of playing sports are numbered, and I think he sympathizes with your nervousness about this. He was all for it when I told him I thought it would help."

"That's fantastic," I said. "But what about you? Why did you change your mind?"

"Because the things you said about having more confidence as a woman struck a chord with me," she said. "It also reminded me of why I started when I was a little girl. I wanted to smoke like my mom too because I thought it would make me more of a woman like her. However," she said, "I was serious when I said I wanted for you to be your own woman instead of a carbon copy of me. That's why I bought you the Virginia Slims and a different style purse. So what do you think about the Virginia Slims?" she asked. "Are they womanly enough for you?"

"I love them," I said. "Not that I have any idea what they taste like, but I've always wanted to be a Virginia Slims smoker. How did you know?"

"When you said you wanted to smoke like a woman, that was the first brand that came to mind," my mother said. "And then I thought about their slogan…"

"You've come a long way baby," I said.

"That's right," my mother said. "You have come a long way and you're going a lot further. It just seemed so appropriate to me."

"Can I smoke them today when we go out?" I asked excitedly.

Mom laughed. "Smoking isn't as easy as it looks, honey. As a matter of fact, there's a very good chance that your first cigarette might be your last cigarette, and I'm hoping that's the case. But even if you do get to the point where you can smoke without coughing out your lungs, you still need to learn the feminine mannerisms of smoking like a woman. Otherwise, that womanly confidence you're looking for is going to elude you."

"Can I try one now?"

"Now's as good a time as any," my mother said. "We don't need to leave for another hour or so. There's a lighter in your purse."

I rummaged through my new purse until I came up with some thing that felt like a lighter. "It's pink," I said.

"Color really doesn't matter," my mom said, "but I thought you'd get a kick out of a pink one. Would you like to do this in front of the mirror?" she asked.

"How did you know that?" I asked.

Mom giggled and said, "Because I did the same thing when I started silly. All girls do."

I approached the dresser mirror nervously with my cigarette case and pink lighter in hand. I saw my moment of truth reflected in the mirror as I withdrew a slim white cigarette from my Louis Vouitton case. The first thing I noticed was the contrast of my dark red nails against the white filter. I raised my hand and placed the cigarette between my lips which were so elegantly coated in lipstick. I paused to admire the effect and that's when my mother saw my erect penis pushing against my skirt.

Mom laughed out loud and said, "Someone needs a gaffe." Sensing my embarrassment, she told me not to worry about it. "I should have said something about it the first night you got dressed up, but time got away from me. I'm glad you're excited. It just means you're happy and that makes me happy. Go ahead and light up. I want to see how you do."

"Okay," I said as turned and faced the mirror. "Here goes everything," I said as brought the lighter to life and touched the flame against my cigarette.

"Suck on it like you're sucking on a straw," my mother said. "But be careful about breathing too much in."

I followed my mother's advice and felt my mouth fill with a warm minty taste. So far so good, I thought as I opened my mouth to inhale.

My mother had warned me that the smoke would seem harsh, but I had neglected to give her warning any credence because she was a woman and I was a tough guy. My respect for her and other smokers rose exponentially as my lungs caught on fire and I doubled over from the pain. I felt my mother's hand on my back as I coughed and coughed. My eyes filled with water and I was lucky that I didn't drop my cigarette on the carpet.

Mom laughed and said, "Not as easy as it looks. Is it?"

I coughed out the words, "How do you do it Mom? Its awful!"

"Had enough then?" she asked as she tried to take the cigarette from my hand.

"No," I said as I moved my hand away from hers. In spite of the initial discomfort, I wanted to keep trying it. Smoking was part of the mental image I had of "Nancy."

"It does get better, right?" I asked as I took a reluctant, slight drag and exhaled. The second puff of smoke was as awful as the first but at least I knew what to expect.

"Unfortunately it does get better with practice," my mother said.

I asked my mom if I was holding it right.

"I wouldn't worry about that right now. We can work on your mannerisms after you get used to inhaling."

"Okay," I said as I lifted the cigarette to my mouth for another go at it.

"How long does it take to get used to it?" I asked.

"Not as long as you'd think," my mother said.

My third puff went down easier. It wasn't quite as bad that time. "My head is spinning," I said. "Is that normal?"

"The light headedness goes away once you develop a tolerance for it," she said.

Five cigarettes and an hour and a half later, I still hadn't developed a tolerance for it. I felt the way I did after having a glass of wine, but at least I wasn't coughing any more.

*****

I'd never been to my mother's salon before but I had envisioned it as being along the same lines as Great Clips. It wasn't. I don't think there was anything less than 40 years old in the salon, including the customers and the equipment. The salon had eight chairs- four on each side. There were also four helmet hair drier seats.

Several of the stylists and a couple of the customers said hi to my mother when we walked in. The receptionist, a lady of about 50 plus winked at me and smiled knowingly. She turned toward the back of the salon and called out to Brenda. "Your ten o'clock appointment is here."

A woman, who could only be Brenda, strolled past the chairs to the front of the salon. I guess her age to be about 60. She had a large bouffant hair-do and a lot of rings on her fingers.

Brenda hugged my mother and said, "Its so good to see you, Karen. I wasn't really sure if you'd make the appointment."

"On the contrary," my mother said. "Nancy wouldn't have missed this for the world. Isn't that right, Nancy?"

I smiled nervously and nodded.

Brenda raised one eyebrow and repeated my name. "It fits you," she said. "Well come on back 'Nancy' and let me see what kind of damage we can do."

Mom and I followed her back to the last chair on the right hand side. She motioned for me to take a seat and then she threw a nylon smock over my chest and snapped it behind my back. "Nice wig," she said.

"It's human hair," my mother said.

"Excellent," Brenda said as she took her scissors to it, shaping it slightly yet still keeping the wavy shoulder-length. "By the way Karen, you did a nice job with her make-up."

My mother thanked her but said said I was hoping to look a little older.

"I see," Brenda said. "So tell me Nancy, how old are you really?"

"16," I said nervously, wondering what Brenda thought of me.

She nodded as she studied my face, "And how old do you want to look?" she asked.

"I was hoping to look around 45 or 46," I said.

"That's shouldn't be a problem," Brenda said. "We can do that with a touch of latex for wrinkles around the eyes and mouth and regular make-up. It's all about using the make-up to create shadowing." She told my mother to pay attention. "Nancy should be able to do this herself, but you might need to help her the first few times."

Brenda talked to me and asked me questions as she did my make-up. None of her questions had anything to do with what she was doing to me and all of them were humiliating.

"So tell me Nancy, do you have any men friends?" she asked as she worked on my eyes, applying some kind of latex pieces.

"Like a boyfriend?" I asked, afraid to talk to much and ruin her work.

Brenda laughed and asked, "What other kind of men friends are there?"

"Nancy plays football when he's not being a woman," my mother said, "So I think he thought you were talking about those kinds of friends."

"Well after I'm done with you, those kinds of friends are going to be a little young for you. If you know what I mean," Brenda said with a wink.

I told her I didn't like guys like that. "I'm not gay," I said.

Brenda snickered. "Gay or not, the men are going to like you, so you best to get used to their attention."

I tried not to frown as Brenda continued working on my face. I didn't say much either, and let Brenda and Mom chat as she worked on my face, applying her latex appliances and redoing my makeup where necessary.

After about a half an hour, Brenda turned my chair so that I was directly facing the mirror. "How's that?" she asked. "Is that old enough for you?"

Staring back at me was a very attractive blonde woman easily in her mid-forties. Brenda had given me crow's feet at my eyes and slight wrinkles around my mouth. Coupled with the perfectly applied, heavy yet tasteful makeup on my face, I looked decades older. I could easily pass for one of my friends' hot mothers, or even the mother of a college-aged kid. I loved it!

I blinked at myself and swallowed. "That's amazing," I whispered. "I look beautiful. Thank you!"

Brenda smiled and said, "Don't thank me yet. You'll look even more beautiful once I clean up your eyebrows."

"You mean pluck them?" I asked warily.

"That's right, sweetie. You know what they say about women's eye brows. You can't get fucked until you've been plucked."

I didn't think that was very funny but it got a big laugh out of Brenda and my mom.

I reminded her not to get carried away, that I still had to go back to school on Monday.

My mother pleaded with me to let Brenda shape them up. "It won't be so noticeable," she said.

"Your mom is right," Brenda said. "A little shaping will make a huge difference. You'd be doing yourself a great disservice if you didn't let me do it."

"Okay," I said. "But don't go crazy with it."

I should have known something was up when Brenda spun the chair back around so that I couldn't see myself in the mirror. The other two red flags were the pain I was feeling from all the plucking and the concerned look on my mother's face. "Watch her, Mom," I said. "Don't let her do too much."

My mother bit her bottom lip and nodded.

"I think that should about do it for your brows," Brenda said. "The next thing you're going to need is a manicure. Your cuticles are horrible!" she said as she turned my hand over in my lap.

"Can I see myself in the mirror first?" I asked.

"Maybe we should wait until after the manicure," Brenda said. "You want to see the whole effect together, don't you?"

"Is something wrong with my eyebrows?" I asked as I looked at my mom. "Did she take too much off?"

Mom shook her head nervously and told me I looked fantastic.

I bent forward so that I could get a foot on the floor and spun myself around to the mirror. I gasped in horror. The same beautiful middle-aged woman was there, just with thinner, feminine arched eyebrows. "Oh my God!" I said. "You did too much! I look like a girl! I can't go to school like this!"

Brenda scolded me. "Don't cry," she said, "or you'll ruin your make-up and I'll have to start all over. Now let me turn you around so that I can do your nails."

I pulled my hands away, wary of what she might do next. I told her that I already had polish on my nails.

"You do," Brenda said, "And it's a nice color, but I'm not talking about polishing them. Your cuticles are terrible."

"It's okay, Darren," my mother said. "It doesn't look bad at all and you needed it done. It won't be so noticeable without your wig and make-up and if someone does notice it, we can think up something for you to tell them."

"You can say you lost a bet to your mother," Brenda said as she went to work on my hands. "Besides, what's done is done and there's no sense of crying over spilled milk."

I closed my eyes and tried not to think about what awaited me at school on Monday.

"I wish you'd let me give you some acrylic nails," Brenda said as she worked on my cuticles.

I told Brenda that I couldn't play football with long nails.

"I don't understand," Brenda said. "Do you want to be a woman or a football player?"

I told her that I wanted to be a woman but that I had to finish out the season. Brenda nodded, seeming to understand, as she repainted my nails the same red color I walked in with.

After a few minutes of drying, Brenda placed my hands back on my lap. "That should do it. You look like a million bucks, Nancy."

As I stared at the mirror, I should have been thrilled. For the first time in my life, I saw what I would look like as a middle-aged woman, the woman I had dreamed of being for so long. Brenda had exceeded my wildest expectations, no doubt about it. The woman looking back at me was attractive, sexy, and sophisticated. Looking at my thinned eyebrows, though, the reality of it started to set in. I felt as if my deepest fantasy had just turned into my darkest nightmare.

Becoming a woman was supposed to be a part time thing while I was in school, a disguise I could take on and off as I wanted until I was ready to make it permanent. It wasn't supposed to interfere with school. Why did mom let Brenda get carried away with my eyebrows? And what was that comment about losing a bet? Did Brenda really think that would fly with my friends?

After paying for the damages, my mother quietly escorted me from the salon. We didn't speak until we were both in the car.

"Why didn't you stop her?" I asked. "You had to see what she was doing to me."

My mother lit a cigarette and started the car. "I know you're mad at me right now, but I was trying to do the right thing for you."

"The right thing?" I asked, as I dug into my purse for my cigarette case. "Do you really think the right thing is for me to get my ass kicked when I go back to school?"

"This isn't a game of dress-up," my mother said. "This is for real and you're playing for keeps. If you can't manage to go to school with those eyebrows then you can't manage becoming a woman for real."

I lit a cigarette, cracked the window and exhaled. "So you're saying this is some kind of test?" I asked tersely.

"It didn't start out that way," my mother said. "I didn't wake up this morning and try to think of a way to humiliate you in front of your friends at school. But since we're talking about it, you're going to need to grow yourself some tough skin. I understand you'd like to keep this whole thing a secret, but you're kidding yourself if you think that no one will ever find out. And not everybody is going to be as understanding as your father and I."

"I'm not ready for this, Mom."

"Ready for what?" she asked. "Becoming a woman or for people finding out about what you're doing?"

"I want to be a woman."

"That's good," my mother said, "Because you sure look like one. I don't know if you noticed it back there at the salon, but you and I could pass for sisters."

"I did notice and it made me very happy," I said.

"Then start acting like you're happy," my mother said. "We can't change what's happened so lets make the best of it. We're going shopping and your father told me to buy as much as you need. If we don't get everything, we can go back. And I assure you that we're going to have to go back. A woman never has everything she needs, if she did, she'd be a man. So cheer up!"

I looked at the cigarette between my fingers and then down at my lap. I was sporting an erection again. I wasn't surprised because that always happened to me when I thought about or saw attractive older women smoking. I reached up and tilted the rearview mirror so that I could see my face. I was pretending to look at my new femininely arched eyebrows and wrinkles. I was doing that, but I also wanted to see an attractive older woman smoking a cigarette. And now I was that woman.

My penis grew bolder at that thought. "Mom. I think we better get that gaffe you were talking about," I said.

Mom pulled into a well known adult book store called Planet 69. "I'm not positive, but I think we might be able to find a gaffe for you here," she said as she parked the car.

"Have you ever been here before?" I asked as we got out of the car.

"Certainly not," my mother said with an air of distaste. "I've just heard that it has more than books."

Books, I thought. Yeah. How many times had I used a book to cover up an unintended erection in school. I thought of myself walking around in public holding an adult book in front of my skirt.

"If nothing else, we can tape it back," my mother said as walked inside.

It only took a quick glance around the store for us both to realize we looked out of place. Two attractive housewife types tend to stick out like a sore thumb in a place like this.

A scraggly looking pervert with glasses came from around the counter and asked if he could help us.

"I hope you can," my mother said. "Do you sell gaffes?"

The pervert squinted behind his glasses and grinned. "I suppose we do," he said, "But what would a nice woman like you need with a gaffe?"

My mother blushed. "It's not for me," she said as she put her hand on my shoulder. "It's for my son, Darren. But you can call him Nancy. He wants to be a woman, but his penis is getting in the way."

I looked at my mom in disbelief. What was she doing? I thought as I blushed furiously beneath my makeup.

The pervert's eyes flew open. "You're a man?" he asked.

"No. He's a boy," my mother said confidently, squeezing my shoulder reassuringly. "He's 16. His makeup just makes him look a lot older than he is. This is who he wants to look like, and I'm trying to help him."

The guy just smirked, thinking Mom was messing with him. "Yeah, right, lady. Maybe this a guy, but no way he's a kid."

My mother's reassurance emboldened me, and I became quite annoyed at this little man for mocking her. I hadn't worked out a decent female voice yet, so I spoke in my own. "She's not kidding. I really am 16," I said, trying to sound as confident as I could.

The pervert's jaw dropped, but he couldn't take his eyes off me. I stood up a little straighter, more ladylike, and met his gaze.

The guy shook his head in disbelief. "You have to be over 18 to come inside the store, but you sure look a lot older, kid. I won't tell anybody if you won't." He pointed past a display of blow-up dolls and said, "The gaffes are in the corner."

My mother thanked the pervert and escorted me to the other side of the store where we picked out five gaffes for me. After paying for them, my mother asked if the pervert if he had a place where I could put one on.

"You can use the bathroom," he said, still trying to figure out if we were telling the truth about my real identity.

Like Mother Like Son 6

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Caught with Consequences
  • Sweet / Sentimental

Other Keywords: 

  • Mothers
  • Older Woman
  • middle-age

Permission: 

  • Posted by author(s)

16 year old Darren Peterman goes shopping with his mom at the mall as a woman. Later that day, he meets his father while wearing his "older woman" make-up for the first time.

*************
Chapter 6
************

By the time Mom and I walked into Lord and Taylor, I had forgotten all about my eyebrows. I was in awe of my situation and surrounds and I was eagerly anticipating the day of shopping ahead. I mean, there are hundreds of department stores, but there is only one store like Lord and Taylor and that's Lord and Taylor! The store and its selections oozed feminine style, sophistication, and maturity, which was everything I wanted to emulate.

It took less than fifteen minutes for me to appreciate the overwhelming nature of our shopping task. "How long does the store stay opene, Mom?" I whispered, not yet trusting my faux-female voice.

"I know we had fun with that creepy guy at the gaff store, but from now on, you need to call me 'Karen' from now on," she replied, removed a pair of black slacks from a rack. Then she smiled gently as she saw my embarrassment at my mistake. "Don't worry, I don't think anyone heard you. We'll work on your voice over the next couple of weeks." She held the slacks against my padded body to see how they'd look on me. "I'm pretty sure these will fit, and look great, but you'll still need to try them on. And, since you asked, the store closes at nine o'clock, sweetie, the same as the mall."

We couldn't buy a complete upscale middle-aged woman's wardrobe for me in one shopping excursion, so Mom planned to purchase clothes that could be mixed and matched to create a variety of different outfits for any occasion. Granted, it's not rocket science, but I was still in awe of how she explained how this blouse would go with that skirt or how a pair of pants could go with the same blouse and with the right shoes, could make an entirely different look. I loved it.

Personally speaking, though, I like dresses the best and couldn't wait to see one over my false curves. Mom promised to buy me one or two, but she assured me I'd have more use for skirts and slacks and jackets and blouses. Better to mix pieces to create different outfits, she reminded me. I trusted her judgment, letting her experienced eye pick out my clothes.

She set me up with everything I needed from top to bottom. Undergarments from bras to girdles to slips, the mix-and-match outfits, several pairs of shoes and boots in my size along with expensive makeup and perfume.

One thing that surprised me during our trip was that I gained more of an appreciation for women's jeans - not because I particularly like jeans, but because they go so well with sweaters. I figured with the right padding on my hips and butt and breasts, the jeans and sweaters would make me look like any woman my mother's age.

We'd been shopping for about two hours when my mother started complaining that she was long overdue for a cigarette break. She suggested we pay for everything and stow them in the car before lunch.

On the way to the check out, I saw a display of Christmas-themed sweatshirts. I know they're unbelievably tacky, with their sewn on cartoons and bells, but they absolutely scream housewife and mother. Have you ever known a middle-aged woman who doesn't have at least one of these tacky seasonal sweat shirts?

"You like those. Don't you?" Mom asked as I caressed the sleeve of one. It was bright red with a reindeer cartoon sewn on the front with a jingle bell on its nose.

"It's kind of embarrassing, but yes. I love it," I said. "It reminds me of you at Christmas."

Mom smiled warmly. "So you wouldn't be embarrassed to run around town with it on? With that bell dangling and jingling from your breasts, people would hear you for miles around," she said.

"I know," I said excitedly. "Wouldn't that be cool?"

"Yes, it would be," she replied as she found the same sweater in my size and handed it to me. "Now you can look like a Christmas mother," she said as we got in line for the check out.

****

After putting our shopping bags in the back seat of her Mercedes, Mom told me she was going to start the car and have a cigarette. "It's too cold to stand out there and smoke," she said.

I didn't really feel like I needed a cigarette but I wasn't going to pass up a chance to smoke with my mom as an adult and an equal.

"How do your lungs feel?" Mom asked.

I lit my cigarette and inhaled without coughing. "Miserable," I said.

"I bet they do," she said. "That's their way of telling you to stop before it's too late."

I told her that I didn't want to stop.

"I know you don't," she said, "and I don't expect you to. I'm sure you'll probably have a pack a day habit by the end of the week. And by the end of summer, who knows? You'll probably be up to three packs a day like me and my friends."

The thought of smoking as much as my mom and her friends aroused me but my newly installed gaffe prevented me from expressing it.

"Karen, I was wondering. Do you really enjoy smoking? You know. Like does it really feel good to you?"

"First of all, I want to thank you for calling me by my name," she said, "and secondly, I'm not going to lie to you. I enjoy smoking very much and so will you some day. But it's not always like that. I'm constantly getting chest infections and bronchitis and that's because I'm a smoker. When I'm sick like that it hurts to smoke, but it hurts worse when I don't. And even when I'm not sick, I get so out of breath from just simplest things, like walking around this mall. I know you don't believe me yet, but you're going to feel it when you go to practice on Monday. It's going to be a small preview of what you can expect from being a smoker."

****

Mom and I arrived back home sometime before ten o'clock. It was late and we were tired. Sammy had gone to bed hours before but my dad was waiting for us in the living room.

It was the first time my father had seen me with my older woman make-up on and he was astounded to say the least.

"Darren! Is that really you under all that?" he asked.

Mom reminded him to call me Nancy while I was dressed for the part, and that I should call him "Bill", as he was now supposed to be my brother.

"I'm sorry, Nancy," Bill said. "No offense."

"None taken," I replied, "So what do you think?" I asked nervously. "Do I look like an older woman?"

"You really do, and a beautiful one at that" he said, "I don't know if I can get used to it, but you look amazing. It's really confusing for me. I know you're my son but looking at you now, it's just hard for me to wrap my brain around it."

"Well get used to it, Bill," Mom said lovingly, "Because Nancy is in this for the long haul. Once summer gets here, if she decides this is the life she wants, we'll never see our boy again, and you'll have a sister for real."

I rolled my eyes at her dramatics. "Geeze, Mom - Karen. You don't have to say it like that," I said. "Deep down I'm always going to be you guys' son. I'm just not going to look like it."

"So how was your first day in public as a woman?" Dad asked.

I told him it was great but that it was unbelievably scary. "I kept thinking someone I knew was going to recognize me, and I was afraid of messing up and doing things the way a boy would. But I'm getting use to it."

"I can't imagine what you're going through," Dad said, then he hesitated for a moment. "Your mother said you started smoking to help with the stress. Is that true?"

I nodded sheepishly and thanked him for giving me permission.

"I know that smoking relaxes your mother when she's stressed out. Is it helping with your situation?" he asked.

I didn't really start smoking because of my nerves, but I stuck to the explanation Mom and I had agreed on. I told him it that it was helping me a lot.

"I'm glad to hear its helping," my father said. "By the way, I had a little talk with Sammy today and I told him that you've started smoking and I explained to him why you need to do it," he said.

"How did he take it?" Mom asked, as she lit up a cigarette of her own.

"I won't lie to you," Dad said. "He took it pretty hard at first and I can't blame him for that. Darren has been his big brother all his life and now he's having to think of him as his older aunt. You have to admit, it is kind of confusing. But the good thing is that he came around after we talked it about it for a while. I think he's getting to the point where he's starting to accept that Nancy isn't his brother and as an older woman, she's going to do a lot of things that Darren would never do."

Mom breathed a sigh of relief and said, "So do you really think Sammy is starting to accept Nancy as an older woman?" she asked.

"I think he is," Dadl said, "But I've been thinking about it and I think it would help if Sammy spent some quality time with Darren, as Nancy of course. You got to think of it from Sammy's perspective. He's losing the brother he's loved and looked up to all his life. He needs to know that Darren still loves him even if he's going to be a woman."

"I think your father is right," Mom said. "I know you can't toss a football around with him the way you used to, but maybe you can take him to the park tomorrow and watch him play. Do you think you can go out in public without me?" she asked.

Like Mother Like Son 7

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Caught with Consequences
  • Sweet / Sentimental

Other Keywords: 

  • Mom
  • older women envy

Permission: 

  • Posted by author(s)

Written by Sharon Parsons and edited by Victor G.

16 year old Darren Peterman tries out his older woman disguise and is presented to his little brother as the boy's Aunt Nancy- a 46 year old smoker. Later that day, Aunt Nancy takes her young nephew to the park.

***************
Chapter 7
**************

When I woke up Sunday morning, I felt as if an elephant was sitting on my chest. Of course, my heavy breast forms played a big role, but so did my heavy smoking the day before. I looked over to the nightstand to see my elegant-looking Louis Vouitton cigarette case sitting next to the ashtray. Even though my lungs were begging me not to light up, I reached for the case and pulled out one of my menthol Virginia Slims.

I have an image to uphold, I rationalized as I disregarded my body's repulsion to tobacco and lit up. I'm supposed to be a middle-aged woman who's most likely smoked for years. It only made sense that she'd want a cigarette this early in the morning.

The first puff hurt my chest and made me cough. My mother usually smoked a cigarette before getting out of bed and I was determined to do the same thing, if only to follow her lead.

I had yet to smoke a cigarette in public in front of anyone other than my mom, least of all dressed as my older female alter ego, but that was about to change. Everybody would probably be downstairs after I got dressed, including Sammy. Even though the thought of smoking and presenting myself as an adult woman to him was embarrassing, I knew that I desperately needed to introduce him to "Nancy" and just get it over with.

As a boy, I couldn't imagine ever smoking in public. Even the thought of smoking in private while wearing boys clothes made me sick. As far as I was concerned, if guys were going to smoke, they should stick to pipes and cigars. Cigarettes were just too feminine for men. And what about wearing dresses and reading women's magazines? Was that too feminine for men? Of course it was!

All my life, I'd gone out of my way not to look or act like a sissy. That's why I excelled at sports and being a boy. I couldn't bear the humiliation of someone learning out my inner thoughts and feelings. I'd been caught before by my parents in my mother's clothes and it had been horrifying and terrible. I had been so ashamed, it almost killed any thoughts I had of becoming "Nancy." But my deep desire to present myself to the world as a beautiful, sophisticated older woman would not be denied, and here I found myself somehow making it come true.

I was still afraid of being found out, in spite of the complexity of my disguise, but now I suddenly had my parent's support and anything was possible. Their support gave me courage, but the shame still lingered, partly because I wasn't completely honest with my parents and Dr. Girardi. They were just filling in the blanks and I was more than willing to let them. However, I knew beyond a shadow of a doubt that my new life as an older woman would come to a screeching halt if they ever discovered what really made me tick.

The sad truth was that I was doing this for a thrill. The million dollar question was, is it worth it? Apparently, I must have thought so, or else I wouldn't have let my elaborate charade go so far. Right now, it's just padding and makeup and wigs. But it's going to go so much farther than this if I don't put a stop to it.

Is it worth it? I sure thought so last night when I was jacking myself off silly, dressed in my mother's nightgown and smoking a cigarette. Being able to dress and look and smoke like an older woman had thrown my masturbation sessions into an amazing high gear. I was experiencing orgasms that had previously been unobtainable. But how did I feel after that, when I was using the tissues at my bedside to clean up the mess left by my still-teenaged hormones?

What goes up must come down and that's exactly what happens after I have an orgasm. In spite of the amazing climax, I had been overcome with regret and remorse peppered with guilt and shame.

I have a great life as a boy. Why am I throwing away a promising future as a man? I'm doing it for the thrill of course, but is it worth it?

I've been dealing with post-orgasm depression all my life, but the depression and remorse have always been fleeting. My life was a vicious cycle of taboos, sexual thrills, and remorse.

"Nancy" was my chance to put an end to the remorse. With my parents' help and support, I would be able to remove any obstacles in my way. Yesterday, when I glued on my breast forms and nestled them into a silk bra, I felt bad about it because I had other options. Removing those options would remove the guilt. The same held true for my developing smoking habit. I felt bad about a smoking because I knew I had an option. Addiction - the same kind of addiction to nicotine a middle-aged woman like "Nancy" would have - would remove the option, which is why I forced myself to smoke a second cigarette before getting out of bed.

Just like my mom, I thought as I removed a cigarette from my case and lit it. My penis stiffened, signaling the end of my remorse. The thought of living the rest of my life as both an older woman and a smoker was more than enough for me. I smiled longingly as I imagined what it would be like to have cushiony curves all over my body without glueing or strapping them on. I couldn't wait for my hair to grow out so that I could get rid of my wig.

I imagined moving out and getting a place of my own. I vowed to always look my best whether I was cleaning the house or hanging out with my older female friends. I didn't see myself dating because I thought that just being "Nancy" would be enough for me. The idea of being a middle-aged woman and taking care of a family was very appealing to me and something I frequently fantasized about. But it wasn't realistic and I didn't truly need it. Feeling and looking like an older woman and smoking like one was good enough.

*******

I was quite hungry and thirsty but I wasn't about to go downstairs without "Nancy" being in place. I slipped out of my nightgown and took a long, hot, luxurious bath using some sensuous bath salts we'd bought at the mall. I smiled as the water caressed my silky smooth skin. It felt oh so good!

After I was done with my bath, I dried off and wrapped a couple of towels around me. One around my torso, and one around my head in a most feminine manner. Making sure I was completely dry, I sat down at the ornate vanity my father - Bill, who was now my "brother" - had put in my room yesterday while I was out shopping with my mom.

I clicked on the lighted makeup mirror siiting atop the vanity and studied my face. I saw my thin, arched, very feminine-looking eyebrows and sighed. They helped make me look very much like a teenaged girl. At least my latex wrinkles and heavy makeup will make me appear decades older, I reassured myself. However, tomorrow at school I'm going to catch hell for these brows.

No matter, I told myself as I picked up the first latex piece that Brenda had given us and gently applied it at the corners of my right eye. As the adhesive dried and I started working on my left eye, I tried not to grin at the crow's feet they gave me. They made me look so much older. I loved it! I next worked on my mouth, giving myself some slight "age lines" but nothing too extreme. Just enough to make me look like I was in my mid-40s.

I was then ready for my makeup. I picked up a nylon wig cap and slid it over my head, tucking any stray hairs beneath it. I was about to start on my foundation when there was a knock at my bedroom door.

"Nancy?" my mom - Karen- asked, "Are you awake?"

I cleared my throat and used my best "older female" voice, one I'd been practicing for some time. "Yes, Karen. Please come in," I said pleasantly.

Mom walked in to see me at the vanity. "I see you've already gotten started."

"Yes," I replied, still using my female voice, "I guess I'm just anxious to meet my little nephew."

Mom smiled sat next to me at the vanity. "And he's anxious to meet you. Confused, but anxious." She studied my face. "You've done a great job on your wrinkles and age lines. I see you paid attention to Brenda."

I smiled. "Yes, but now I'm a little overwhelmed on everything else. WIth my real makeup, I mean. It was a lot to learn. I'm not sure I can do it right."

Mom patted my hand gently. "I thought so. That's why I thought I'd come up here and help you."

I hugged her. "Thanks, Mo- er... Karen. You're the best 'sister-in-law' I could have!"

Mom smiled and picked up my cigarette case. "Do you mind if I have one?"

"Of course not. Please help yourself," I replied. I was really enjoying this, talking to Karen as if she and I were old friends instead of mother and son.

Mom slid one of my Virginia Slims out of the case and lit up. She made a face and coughed. "Oh my God, I forgot these were menthols. I wasn't expecting that. I'll get one of mine when we're done." She handed me the cigarette.

"Sorry about that." I said, taking the cigarette. I took a long, slow, deep drag, then held the smoke in for moment before letting out a thick cone of smoke into the air above our heads.

Mom nodded appreciatively. "Well, you sure act like a woman that's been smoking forever. You're getting the motions down pat. Did you get that from watching me?"

"Yes," I replied, taking another drag. "Well, you and some other older ladies I've studied over the years." I exhaled.

Mom picked up the foundation and a small sponge. "Well, you did great yesterday. You looked amazing and you're really getting the movements of an adult woman down."

"Well, I have been practicing for a while now. It feels so good to be able to do it in public, especially with your permission."

"For what its worth, I have to admit you look more confident when you smoke," she said as she continued working on my face, putting down several layers of foundation. "And your voice, too. I like it. I like the slight huskiness to it. It makes you sound more genuine, as if you've been smoking for a long time."

"Yes, I've worked on that as well," I said, taking another deep drag on my cigarette. "I figured it would be the most important thing if I was going to pull off passing as an adult woman."

Mom finished up my foundation, then went to work on my eyes. "You know, Sammy is pretty confused about all this," she said as she started on my eye shadow. "What are you going to tell him?"

I paused for a moment because I wasn't sure how to answer. I took a final drag on my cigarette and crushed it out in the ashtray.

"Honestly, I really don't know yet," I replied, "Just the truth, I guess. That this is what I want more than anything in the world and that I hope he understands."

Mom nodded and continued to work her magic, finishing up with eye shadow, eye liner and mascara on both my eyes. Then she went to work on my blush and then my lips. She outlined them in a lovely rose color, then filled them in with a matching lipstick. She even repainted my 1-inch long false nails in a color to match. She made sure to explain to me every step so that I could start working on it on my own in the future.

When she was finished with my face, I looked in the mirror and smiled. I looked amazing! Nancy's beautiful, middle-aged face stared back at me. Although I didn't have my wig or glasses on and Darren's slender, athletic teeanged boy's body rested below her face, it was still a sight to behold.

"Thank you, Karen. I love how I look!" I hugged her tightly.

"You're welcome, sweetie. I'll leave you alone now so that you can get dressed. Sammy and your... brother are waiting." She walked out the door, closing it behind her.

I walked to my dressed and pulled out my foundation garments. I pulled on my gaff, hiding away my penis and testicles and sliding it into pace. I pulled on a padded girdle, one that gave me rounder, more mature female curves. I pulled on a bra and, with my large breast forms, had to struggle to get clasps closed, but succeeded after a couple of attempts. I slid on a sheer black pair of control-top pantyhose as well, loving the way they slid up my still-smooth legs.

Foundation garments in place, I was ready for my outfit. I knew it wasn't the season for it yet, being a couple of weeks before Thanksgiving still, but I found my reindeer jingle bell sweat shirt in the closet. I just wanted to see how it would look on me. Plus, it might make Sammy laugh a little, which would help me. I was nervous enough as it was. I carefully pulled the sweater over my head, being careful not to mar my well-applied makeup. I thought it would look perfect with my new pair of women's jeans. I slid those on as well, loving the way they looked over my hip and butt pads. I slipped my hosed feet into a pair of low-heeled slippers and walked back to the vanity. I put on a pair of gold clip-on earrings, thinking that someday I'll get my ears pierced. A gold ladies' watch was secured to my wrist, giving a look of elegance to my ensemble.

I picked up my long, blonde wig and secured it into place with a few strategic bobby pins, covering the wig cap and my short boyish brown hair beneath. I shook my head, making sure the wig would stay on. Satisfied, I looked at the women's glasses nearby. There was one more thing before that, however.

I walked into my bathroom and pulled something out from a drawer, something I hadn't told Karen about. I'd bought them a couple of months ago, just on a lark. It was a pair of colored contact lenses, a lovely shade of green. They weren't corrective, just to change the color of my eyes from my usual brown. I presented Nancy online as having green eyes, and had doctored my eyes to match. Maybe it wasn't a necessary addition to my faux-female identity, but I didn't want any hint of Darren coming through to shatter the illusion.

I gently placed the contacts into my eyes, again being extra careful with my makeup. Once they were in place, I slid the feminine, stylish glasses on. I gasped.

Nancy Peterman, a beautiful, blonde 46-year-old woman, stared back at me. I couldn't see any sign of the teenaged boy I really was beneath. Well-styled hair, perfect makeup, subtle wrinkles, tacky feminine sweater, the feminine glasses, the nearby Louis Vuitton cigarette case with menthol Virginia Slims cigarettes inside, all cried out "middle-aged woman."

And that woman was me!

Breathing deep to calm my nerves, I grabbed my cigarettes and ventured downstairs to present myself to my little brother for the first time as an older woman.

I found Sammy in the kitchen with our parents. He was eating a bowl of cereal while our father read the paper and our mother drank coffee and smoked a cigarette.

Dad put his newspaper down and got up to kiss me on the cheek, being careful with my makeup. He said I looked incredible, which made me blush a little. With a smile, Mom blew a puff of smoke toward the ceiling and told me that I looked adorable in my reindeer sweatshirt. Sammy dropped his spoon on the floor.

"Darren! Is that you, bro?" Sammy asked as he picked up his spoon.

It went against my nature, but I knew I had to act the part. I couldn't let him see me as Darren at all. I smiled, walked over to him and pinched his cheek. "Yes, it's me, dear," I said in my female voice, "But right now, you need to call me Aunt Nancy. Do you think you can do that?" I asked.

Sammy nodded and pointed to the cigarette case in my hand. "Are those real cigarettes?" he asked. "Dad said you started smoking because you're nervous about people seeing you dressed like that."

My little brother wanted to know if I started smoking because I was nervous about people seeing me dressed like a woman. Talk about being nervous. I was stressed to the max and I felt like I was going to fall off my legs. Was I really going to smoke in front of my dad and little brother?

"That's right, honey. They are real and they do help me," I said as I nervously removed a cigarette from the case. I couldn't help but notice Sammy's eyes getting larger as I closed the case and positioned the cigarette between my fingers the way our mother would hold it.

I urged myself to stay calm and look confident as I fumbled for my lighter which wasn't there. "I must have left my lighter in my room," I mumbled to myself.

"Bill," my mother said as he handed my father her lighter. "Be a dear and light Nancy's cigarette for her."

My dad reached over the table, holding the lighter forth. I wanted to scream and run back to my room but I held my ground and did my best to look confident and womanly as I lifted the cigarette and placed it between my painted lips.

I'd seen my father light my mother's cigarettes for her at least a million times and he'd always looked at ease doing so, but he wasn't at ease now. He looked visibly shaken as he tried without success to coax a flame from the lighter.

I did what I'd seen my mother do and steadied his hand with mine. He smiled at me weakly and a flame erupted from the lighter. I moved his hand closer to the end of my cigarette and held it until I was sure it was lit. "Thanks Bill," I said as I released his hand.

All eyes were upon me as I struck the pose of mature confident woman. I held the my cigarette aloft by my cheek and smiled as I exhaled a cloud of smoke toward the ceiling. My lungs burned from the abuse but I covered the pain with a confident smile.

Perhaps I was making too much out of it but the stakes seemed high to me. I needed my father and Sammy to see me as a middle-aged woman and a committed smoker like my mom.

My heart fell when I turned to see Sammy grinning an ear to ear. Oh my God, I thought. He's laughing at me. At me, not at my sweater like I hoped he would. My parents noticed it too and my dad asked Sammy what was so funny.

"Nothing is funny," Sammy said. "I just think she looks so pretty! I can't wait to show Aunt Nancy to all my friends."

I bent down and kissed Sammy on the forehead. "Thank you, sweetheart. You made your Aunt Nancy a very happy woman. I'm looking forward to meeting your friends. Will they be at the park?"

"Yeah," Sammy said. "They're all going to be there. We're going to play a game of tackle football."

"Maybe you should play touch instead of tackle," my mother said nervously. "I don't want you getting hurt."

"Oh let the kid play tackle," my dad said. "It's good for toughening him up."

I couldn't help but notice the pride in my father's voice as he talked about Sammy being tough. It was just a couple days ago that I had the best game of my life and he was proud of me then. I wonder if he's proud of me now, watching his son in a wig and makeup, prancing around in a reindeer sweat shirt and smoking a Virginia Slims cigarette.

My ego was granted a reprieve when I felt my mother - Karen, I told myelf; in spite of regressing for a moment with Sammy, they were now "Bill and Karen" to me - squeeze my hand. I saw a proud look on her face. She was the one I was trying to impress and I must have succeeded, judging by her expression.

******

After breakfast, Mom took me aside. "So, are you nervous about taking Sammy out in public without me?"

"No, I'll be fine," I replied, "He seems to be taking it well."

Mom nodded. "Just a suggestion, but you... might want to change clothes. That jingly reindeer sweater might be fun around the house, but it's not be the best outfit to wear to meet Sammy's friends."

I laughed. "No, perhaps not."

Mom smiled mysteriously. "Or their fathers, for that matter."

Wondering just what she meant by that, I made my way back to the bedroom and walked into the closet. As I went through my new feminine wardrobe, picking out a decent outfit, I thought some more about my mother's comment about meeting Sammy's friends' fathers. I hadn't considered that. These men had always seen me as Darren, Sammy's football hero older brother. Now I'd be in front of them as his stylish, sexy, middle-aged aunt. Why not dress the part?

I chose several articles of clothing and draped them on my bed. I gently removed my wig and took off my sweater and jeans, leaving my panty hose and foundation garments in place.

Since it was cold out, I decided to dress for it. I pulled on a pair of black leather high-heeled boots and zipped them into place, loving the way they looked over my legs. I then pulled on a silk half-slip and over that a long, calf-length black wool skirt that showed off my lower curves nicely and went perfectly with my boots. I then pulled a charcoal gray wool turtleneck sweater over my head - again, careful with my makeup - and adjusted it over my voluptuous "breasts." I put on a gold necklace to complete the look.

I secured my wig back into place and put my glasses back on. Wow, I thought. I look fantastic! I look like an attractive, elegant businesswoman, and that's exactly what I wanted to look like. I couldn't wait to take Sammy to the park and introduce more people to "Nancy Peterman."

I walked to the hall closet and grabbed my new long black wool coat. "Sammy, sweetie, are you ready to go?" I called out.

"One sec, Aunt Nancy!" Sammy replied.

As I slid my arms into my coat, Mom walked over. She handed me her black leather gloves, the ones that I always envied. They always looked so great on her hands, very stylish and sophisticated. "It's a little chilly out," she said, "You might want these. They should fit you, your hands aren't that big yet. They'll also help protect those pretty nails. Plus you'll need them while you're in the cold reading this."

She handed me a small paperback book. "You can read it to pass the time while Sammy is playing," she said.

I looked at the cover. "Mastering The Game Of Bridge. How lovely, thank you!"

"I thought you might want to bone up on the game before I introduce you to the ladies," she said with a smile.

I showed my gratitude with a hug. "Oh, hun, thank you so much! I'll read it from cover to cover!" I said.

She pulled back and looked at me with a curious expression.

"I need to tell you something," she began cautiously, "While you're gone, I'm going to make a few phone calls and explain the situation to some people."

"You're going to tell Mrs. Estes and Mrs. Jackson?" I asked, fully expecting that.

Mom paused for a moment. "Yes, but I was also going to tell your Aunt Carol... and your grandparents."

My jaw dropped. "You're going to tell Mammaw and Pappaw?" I said fearfully, inadvertently reverting back to my real voice.

"They're coming over for Thanksgiving," Karen said, trying to reassure me. "I just think this will go a lot smoother if we break the ice over the phone rather than just marching you out there as an adult woman."

I knew she was right, but I still didn't like it. I understood her telling Mrs. Estes and Mrs. Jackson about me, I was going to be part of their bridge group. But I was terrified about my mother's parents finding out. They were very old school and super conservative. On the other hand, Aunt Carol, my mother's sister was a very cool lady. "What about Brian. Is he coming too?" I asked. Brian was my cousin, Aunt Carol's 15-year-old son.

"Of course he is," my mother said. "Did you think Carol would leave him at home?"

I shrugged and said, "No, but I was thinking maybe he'd spend Thanksgiving with his father this year." My Aunt Carol and Uncle Tony had gotten a divorce two years earlier.

"Sorry, girlfriend. No such luck," Mom said. I sighed and nodded.

She put her arm on my shoulder reassuringly. "You know, honey, there's no law that says you have to look like a woman on Thanksgiving."

"I know," I replied, still in my male voice, "But I guess you've got to break a few eggs if you want to have an omelet. Right?"

"Truer words have never been spoken," she said. She pulled a set of car keys from her pocket. "In the meantime, if you're going to drive around town as a middle-aged lady, at least do it in style."

My painted eyes grew wide. "You're letting me borrow your Mercedes?"

Karen nodded. "Why not, Nancy? You can't go around town in Darren's old beat up Pontiac. You need a car that's more fitting a woman of your age."

"But... I'm only 16. I've only been driving for a year now. Are you sure you're okay with it?"

"Yes, dear. I want you to feel fully like the older woman you want to be. Just be extra careful, okay?"ӬӬI smiled and shifted back to my "Nancy" voice. "Of course, hun. I've got my little nephew to look out for as well."

******

Sammy and I walked out to the car, he with his football and me with my designer purse slung over my arm. My boot heels clicked on the sidewalk as I strode with a middle-aged woman's grace. I felt so wonderful, everything was perfect!

I started the Mercedes and rolled down the window down a crack before lighting a cigarette. It was a little tricky while wearing my mother's leather gloves, but I managed after a couple of tries. I took a deep drag and exhaled out the window.

"Seeing me like this must be really confusing," I said, staying in my "Nancy" persona as I carefully backed the car out of the driveway. Driving in heels was an entirely new experience for me, and I was extra cautious.

Sammy nodded. He's a pretty smart kid for being only 11, and by smart I mean mature for his age. Regardless of what he was about to say, I thought he was taking things pretty well.

"Yeah, it is. I don't get why you want to be like Mom," he said.

I took another drag, blew my smoke out the window and said, "I don't think I get it either. I just know that it's what I want and I've wanted it for as long as I can remember."

"Are you still going to play in your football game next weekend?" he asked.

I nodded. "We're playing Henderson. The team needs me," I replied, then considered my words. "Well, they need Darren."

"Yeah. Henderson sucks," Sammy muttered. I laughed in my female voice.

"Sammy, you shouldn't talk like that in front of your auntie." I playfully scolded.

Sammy didn't reply, but stared at the cigarette between my gloved fingers for a moment. "My P.E. teacher says athletes don't smoke and smokers ain't athletes," he finally said.

I self-consciously flicked the ashes of my cigarette out the window crack. I told him he was right and added that I wasn't going to be an athlete for much longer. "I'm done with sports after we finish the playoffs," I said.

"What about baseball? Aren't you going to play this season?" he asked.

"Probably not," I said. "If I start taking this medicine called female hormones, it's going to make my body change. Right now, I can take off my boobs and get rid of my big hips and go to school and still look like a boy. But if I start taking the medicine, I'm going to grow real boobs. I can't play baseball and have boobs."

"I guess not," Sammy said as he turned and looked out the window.

*******

At the park, Sammy ran off to play football with his friends. I sat on a bench not far from Sammy and his friends. I elegantly crossed my booted legs and opened the book my mother had given me. I usually wasn't much for studying, but this was different. I wanted to prove to Mrs. Jackson and Mrs. Estes that I was worthy of their friendship, and I wasn't willing to leave anything to chance. I'd been reading old copies of my mother's women's magazines religiously and had been practicing my walk and my talk. I pulled a cigarette from my case, lit it, and consciously held it the way I'd seen women do as I learned how to play bridge.

"Excuse me. Is this seat taken?" an adult male voice asked.

I looked up from my book to see a man standing in front of me. It was difficult to judge his height because I was sitting down but he seemed taller than me, even in my heels. I guessed he was at least six feet tall. His hair was dark except for around his temples where it was turning gray. His face was clean shaven and he had a strong chin. I tried to place him but I didn't recognize him.

I remembered the cigarette in my hand and tried to make it less obvious even though it was obvious he'd caught me smoking. But who had he caught, Darren or Nancy? I reminded myself that there wasn't anything wrong about a middle-aged woman smoking a cigarette on a public park bench. Unless he knows I'm really a boy...

It took me only a second or two to process all that and I replied to his question using instinct rather than thinking about what I was going to say. When someone asks if a seat beside you is taken, you politely say "No, it's not." That's exactly what I said.

"Do you mind if I share it with you?" he asked.

I had recovered from the shock of seeing a - well, I had to admit handsome - man standing over me but I was still a hostage to good manners. "No, not at all," I said pleasantly. "Please sit."

The man thanked me and sat down. He introduced himself as Tim Moreland. "My son's the one with the blue sweatshirt and red hat," he said.

Ah, he's Tyler Moreland's dad, I thought to myself. He's a good kid, one of Sammy's friends that I liked.

"I'm with my nephew, Sammy," I said as I gestured toward my "nephew."

"So, you're Sammy Peterman's aunt?" he asked.

"Yes. I'm Nancy Peterman," I said, setting my book down and offering my gloved hand. I wondered if it would have been polite for him to shake my hand first.

Even through the leather of my glove, I could feel that his grip was strong and firm. "It's very nice to meet you, Nancy. So, are you visiting from out of town or do you live nearby?"

I had prepared myself for this question and answered it with ease. "I've been doing a lot of visiting lately, but I'll probably move in with Sammy's parents after my lease runs out in the summer. I'm still looking around for just the right place."

"Well, it's definitely a buyer's market. Do you mind?" he asked as he parted his coat and pulled a pack of Winstons from his shirt pocket.

"No, of course not," I said as I held up the cigarette in my right hand.

"It's a bad habit," Tim said as he lit his cigarette. "So, how old were you when you started?"

"Sixteen," I answered truthfully, "How about you?"

"The same," he said as he exhaled into the wind. "The best thing we ever did as a state was to pass a law making it illegal for kids under 18 to smoke and I wish we could have raised it to 21."

"Actually," I said. "It's not illegal for kids under 18 to smoke. They're just not allowed to buy them, so an adult has to do it for them."

"What kind of adult buys a kid cigarettes?" Tim asked sarcastically.

"Oh, I don't know. Maybe the same kind that did for you and me when we were kids," I said with a playful smirk. I finished my cigarette and stepped on it with my boot.

"If you don't mind me asking, I noticed you're not wearing a wedding ring and you still have you're brother's last name," Tim said. "Does that mean you're not married?"

I smiled gently. I had prepared a backstory for Nancy, and I had an answer prepared. "No, I'm not married anymore. I took my maiden name back after my divorce two years ago."

"I'm sorry," Tim said. "Was it a bad break up?"

"It was but it helped that our daughter, Katie, was in college, so she was already grown. She handled it well."

Tim nodded and said, "You're lucky there. Custody of Tyler was our biggest issue when my wife and I divorced."

"Who got Tyler?" I asked. "You or your ex?"

"She did. I get him every other weekend, so that's why I'm here."

****

For the next twenty minutes, Tim and I talked while the boys played football. I found myself really enjoying our conversation. This came as a surprise, because it seemed as if he and I wanted different things. I couldn't say for sure, but I suspected he wanted a date. I knew I made a very attractive woman, so that wasn't a stretch to assume. I, on the other hand, didn't want a date. I was just trying to pass myself off as a woman about his age. Judging by his flirty demeanor, I had completely succeeded.

A wave of euphoria washed over me as I realized Tim had unquestioningly accepted me as a middle-aged woman. I decided to show off a bit by smoking another cigarette in front of him. I pulled a cigarette from my Louis Vuitton case. I held it up for a moment, and, in spite of myself, raised a feminine eyebrow flirtatiously.

Tim took the subtle hint and offered me a light. My heart swooned as I accepted.

Oh my God, I thought. He really thinks I'm a woman. A real older woman!

I felt blanketed by a feeling of sophistication and mature womanhood. I recognized the feeling as one I'd been chasing my entire life. "Thank you," I said sweetly as I exhaled through my smile. "You're quite the gentleman."

"My pleasure," Tim said as he lit a Winston for himself and pocked the lighter. "Always happy to do a favor for a lovely lady."

"That's so sweet of you to say," I said as I raised my cigarette to my lips.

This must be how it feels for a woman when she's swept off her feet by a man, I thought as I continued our conversation. However, I also knew the feeling was wasted on me because I was really a boy. Not only that, Tim was old enough to be my father. I was sure he'd kill me if he discovered the truth.

Flirting with Tim and leading him on was so wrong, but there I was gently touching his arm, giggling at his jokes, and hanging on his every word. If I was leading him on it was because he was making me feel like a woman, and isn't that what I wanted, to be a woman? Of course I did.

I remembered what my mother said about it being okay with her and Dad if I wanted to date older men. She said as long as I was careful, no one would get hurt. Careful wasn't anything I had to worry about. If I was going to go on a date with Tim, it would be because I wanted to feel what a woman feels when she gets attention from a man and not because I wanted to have sex with him. Even if we did go out, the date would end with us shaking hands- not kissing. Besides, he wasn't even my type. First of all, he was a man and I didn't have the hots for men. Second of all, he was a smoker and I think guys that smoke are yucky. I suppose that makes me a hypocrite, but what the hell, I never smoked as a guy so why should Tim? Shouldn't every guy who wants to smoke wear a dress? I almost broke out laughing as I thought of the world in such a state. On the other hand, it would probably go a long way toward cutting cigarette consumption. Oh God, I'm crazy.

I started feeling even crazier the more we talked because the more we talked, the less yucky Tim and his Winstons looked to me. It was so weird because I knew how I felt about guys smoking and I knew I didn't like guys period. However, I was starting to see how romantic it could be for a man and a woman to share a cigarette after they made love. I knew it could never work that way for me and Tim, but I was starting to see how it could work for other women.

"So...," Tim finally began, "What would you think about going out with me Friday night? I was thinking we could do the dinner and drinks thing, maybe a little dancing."

I couldn't exactly tell him that I wasn't free Friday night, that I was playing in a football game against Henderson High School. Tim would probably be in the stands watching that game. But still, the thought of going out on a date with him intrigued me. "I can't make it Friday might, I have a prior engagement. What about Saturday?"

"It's a date," said Tim happily. "Let's trade phone numbers and I'll pick you up at seven."

I wrote my parent's home number down on the back of one his business cards. I noticed with interest that he was an attorney with a prestigious law firm downtown. So, he has a really nice job. Is that something women noticed?

As Tim left with Tyler, I watched them walk away. Tim seemed to be devoted to his son, and had spoken of him glowingly as we talked. I tried to wonder what kind of a woman wold divorce a handsome, charming man like that.

Then it hit me. A real man had asked me out on a date and I'd said yes. I couldn't figure out if I was more excited or scared at the thought.

*****

"You did what?" Mom asked after I'd told her.

I asked if she was mad at me. "I can still call it off," I said. "It's not until Saturday."

Mom hugged me. "Don't you dare!" she said. "Don't call it off. I think it's wonderful. I'm so happy for you, hun. It just caught me off guard because it happened so soon. I wasn't even sure you liked men."

"I don't," I sad adamantly. "It's not like that."

"Then why did you agree to go out with him?" she asked.

I lit a cigarette and shook my head. "I don't know. I just did. I got so caught up in feeling like a woman that I couldn't say no. I guess it was all the attention he was giving me. It really made me feel good about myself and I didn't want it to end, so I said yes. But I didn't mean it."

Mom took me by the arm and said, "I know this must be very confusing for you, but I'll go out on a limb and say you're excited about, it too. Am I right?"

I felt a tear in the corner of my eye and wiped it away with my finger. "I am excited," I said. "But it feels wrong."

She touched my cheek with her finger and said, "It's not wrong if you really want to be a middle-aged woman. Do you?"

I told her I did and that it was all I ever wanted.

"I know that," she said, "And I think the reason you feel excited about this is because you've always wanted something like this to happen. Am I right?"

"I don't know. Maybe," I said.

"Do you still want me to call Dr. Girardi for you tomorrow and make an appointment?" she asked.

"Yes," I said. "More than anything."

****

I woke up the next morning thinking of everything that had happened the day before. An older man had asked me out on a date and I had accepted. My mother had told her friends and some of my relatives that I was in the process of becoming a middle-aged woman. Things like this happen to boys every week. Right?

Of course not. Things like this don't happen to boys every week, but they sure as hell were happening to me. I reached for my first cigarette of the day not because I wanted it but because I needed it.

I'd only been smoking for two days, but I'd smoked a pack each day. I wondered if it would bother me to go to school all day without having one. I didn't want to to school. I had way too much on my mind to be bothered with school. And besides, my eyebrows hadn't grown back. Not that I had expected them to, but still…what would my friends say when they saw them?

****

Before I left for school, my mom gave me some Nicorette gum. She said I'd probably need it to take the edge off now that I was a smoker. Mom was right. I chewed my first piece of nicotine gum right after first period. I was beginning to think I might be addicted already and I wondered if that was something I should be proud of or ashamed of.

It's hard to concentrate on what the teacher is saying when you're distracted with the problems of an adult woman, and I was most definitely distracted. With everything else I had to worry about, I felt my eyebrows were like a target on my forehead. I felt like people were staring as I walked down the halls.

My eyebrows came to a head during 3rd period chemistry class. Charley Conners, a guy on the football team, asked what I did to them. I told him I lost a bet to my mom and I didn't want to talk about it any more. That was good enough for Charley and I prayed it would be good enough for the other guys on my team.

*****

Football practice starts with stretching followed by wind sprints. Needless to say, because of all the smoking I'd done over the weekend, I didn't have the wind to sprint. The coaches gave holy hell over it and the rest of the practice wasn't any better. I remembered what Sammy had said in the car on the way to the park: "Athletes don't smoke and smokers ain't athletes." I had to say at that point I agreed with him and his P.E. teacher.

The first thing I did when I got home was to take a shower and change into woman mode so that I could smoke like one. I only had a few hours, but I was going to make the most of them.

While we were having dinner, Mom told me that she had made an appointment for me to see Dr. Girardi in the morning. She told me that I should dress appropriately, which meant she wanted me to go as Nancy.

Like Mother Like Son 8

Author: 

  • Sharon Parsons

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Caught with Consequences
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • Castration / Male Chastity Devices
  • Estrogen / Hormones

Other Keywords: 

  • Mother Envy
  • Older Woman Envy

Permission: 

  • Posted by author(s)

Edited by Victor G.
16 year old Darren (Nancy) Peterson and his mom pay a visit to Dr. Girardi, a psychiatrist who specializes in transgender issues. Afterwards, Nancy has dinner alone with her father and asks his advice.

**************
Chapter 8
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When I woke up Tuesday morning, it felt like Christmas had arrived early. I still had to go to school and football practice, but not until later in the day. This morning was devoted all to Nancy, and I couldn't wait. I still had my date with Tim Moreland looming, but that was like five days away. The only thing on my mind was becoming Nancy again and presenting myself to Dr. Girardi as her. I was actually excited at the thought.

I took a luxurious bubble bath, taking extra time to carefully shave my legs and under my arms. After drying myself completely, I prepped myself for the coming delicious transformation into a middle-aged woman. As I glued my breast forms to my chest, I studied my face for any signs of hairs on my cheek or chin. Seeing none, I felt so thankful to be a late bloomer and hoped my delayed puberty would benefit me when it came time to start female hormone therapy. I prayed that Dr. Girardi would see fit to prescribe them to me. I hoped she'd understand.

Thoughts of female hormones and what they could do for me flooded my head as I slipped my padded girdle over my slim hips. Oh, to be cushy like a real woman! The six pack on my abdomen mocked me as I pulled on my half slip. Except for the mandatory calisthenics in football practice, I had begun neglecting my daily exercise routines. I didn't want to be obese but I did long for an older woman's slightly flabby belly, just to make the illusion that much more realistic.

I sat on the bed and rolled a pair of dark, sheer pantyhose up my legs before choosing an outfit to wear from my closet. I chose a navy blue stylish skirt and jacket ensemble with a lovely burgundy button-down blouse to go with it. I picked out a pair of navy blue pumps with 3-inch heels to complete the outfit. I smiled, thinking the combination would make me look stylish, yet properly matured and middle aged for Dr. Girardi.

I slipped in my green-tinted, non-prescription contact lenses and made my way back to my vanity. I sat down and pulled on the tight nylon wig cap over my head. I lit a cigarette and started to work on applying my latex wrinkles, followed by a careful, painstaking application of my makeup.

What a wonderful morning ritual, I thought as I watched my face slowly transform into that of a beautiful middle-aged woman.

******

My appointment with Dr. Girardi was for 10 AM, but Mom and I arrived a half hour early so that I could update my records. While I waited for my mom to check us in, I had a seat, making sure to smooth my skirt under me as I sat. I crossed my legs femininely and elegantly and looked around the waiting room .

There were five other people waiting with us. The oldest was a woman who was actually born a guy. I didn't know if she was pre-op, post-op or what, but I could tell she had started HRT later in life, if at all. Nothing against her, but if I was going to do HRT, then I wanted to start sooner rather than later.

I saw two women who were mothers, each had their children with them and they sat on opposite ends of the room. One child appeared to be a ten-year-old girl. She looked to pretty and far too young to be a boy going through transition, but I didn't know and I certainly wasn't going to ask.

The other mother had a boy with her who looked to be around five years old or so. He was playing with Legos and throwing them all over the room while his mother just rolled her eyes in exasperation. The kid was an absolute hellion. I wondered it if it was possible that mother of the 5 year old terror was taking him to Dr. Girardi to have him turned into a girl.

All I knew about these people were just guesses and assumptions. However, I was probably willing to wager cash money on the assumptions I'd made.

I'd only met Dr. Girardi four other times in my whole life, so I didn't know her well. However, she seemed to be a doctor of high standards. I didn't want to think she'd turn a little boy into a little girl just because his mother wanted a daughter.

My mom sat down with the pen and clipboard and began filling out forms and answering questions on them. Sometimes she'd ask me for my input and other times she'd just write down the answers herself. I read all the questions as she answered them.

The name, address, phone and birthday stuff went fast. When she got to the "Reason For Visit" part, she wrote M-F, HRT. There was a half-page list of diseases that I didn't have, each of which she checked "No." And then she got to the smoking and drinking part.

Does the patient drink? If so, how much? My mother checked the yes box and wrote "2 drinks per week". I wondered if that would increase - within reason, of course - once I was able to live as Nancy full-time and could drink "legally." Well, looking the way I did, who would card me?

Is the patient a smoker? If so, how much? Mom checked the yes box and asked, "Should I put down a pack a day?" I nodded and whispered in my older female voice, "Yes." I was still a little nervous, and the question made me think of the Virginia Slims in my purse. I felt like slipping outside for one before meeting Dr. Girardi, but remained in my chair.

Mom completed the rest of the questions and signed on the dotted line before returning the clipboard to the receptionist. As she was walking back to sit down beside me, I noticed she had stolen the pen. My mom has pens from every business in town. She says the businesses want their customers to take them because its advertising. I don't know about that, but we sure have a lot of pens around the house.

About fifteen minutes later, the nursed called out "MIss Peterson?", indicating that that Dr. Girardi was ready to see me. I laid the copy of Woman's Day back on the table and rose to my feet. As I made my way toward Dr. Girardi's office, I felt proud of myself for the graceful way I walked in my heels. In spite of my nervousness, I felt like a confident, mature woman.

I didn't invite my mom to go back with me but she was there by my side as the nurse led us past three examination rooms to Dr. Girardi's office at the end of the hall. Dr. Girardi was sitting at her desk and stood to greet us.

"Hello, Darren. It's been a while," Dr. Girardi said as she shook my femininely-manicured hand and then looked down at my paperwork. "Or would you prefer that I called you Nancy?" she asked.

"Yes, please. I would prefer that," I said in my "Nancy" voice.

Dr. Girardi looked at me curiously, as if studying me. "I think your voice is a nice touch," she said. Have you worked on it long?"

"Yes, I have. Months, in fact, in the privacy of my bedroom. I hope it's believable."

Dr. Girardi nodded. "Very much so. Well done! And I must admit that you look beautiful. I'm even a little jealous."

I smiled. "Thank you. It's not easy. There's a lot of work involved in turning me from Darren to Nancy."

Dr. Girardi continued to study my face. "Did you do your make-up yourself or did your mom help?"

"No. She did it herself," my mother said proudly. I smiled at her in gratitude.

"And your outfit? Very stylish. Did you put it together?" Dr. Girardi asked.

"All Nancy," my mom said with a loving smile.

Dr. Girardi looked me in the eyes. "I don't recall you having green eyes, Darren."

I reached up to remove my glasses so she could see my eyes better. "They're colored contacts."

Dr. Girardi smiled. "So, non-prescription contacts and non-prescription glasses? Isn't that a bit of overkill?"

I shrugged. "I thought it would be a nice twist, another layer of disguising Darren and bringing Nancy that much more to life."

Dr. Girardi jotted down some notes on a pad, then set it aside and leaned on her desk. "Well, you've done a fantastic job all around. If I didn't have your records in front of me, I'd say you were a genetic woman in her mid to late 40's."

"Thank you very much," I said. "That's exactly how I want to look."

Dr. Girardi gestured for us to sit, which we did, then made her way around her desk. She looked over my records. "So, am I to understand that you've given your situation a lot of thought and have decided to move forward with becoming a woman?"

"Yes ma'am, I have, but I want want to look a lot older."

Dr. Girardi smiled gently. "Nancy, I think you should simply call me 'doctor'. I appreciate Darren's instinctive courtesy, but it seems out of place for a woman of your apparent age. Don't you agree?"

I nodded and sat up in a more feminine manner, crossing my legs. "Yes, doctor."

"And you think your life would be more fulfilling if you skipped over the years between 17 and say 45?"

"Yes, doctor, I do. It's all I've ever wanted."

Dr. Girardi looked up from the papers on her desk and said, "As you know, I've already discussed the possibility of you transitioning into a mature woman with your parents. It's not the most conventional transition I've encountered, but from what I can tell, I think you would be considerably happier living as an older woman. I will say however, that I didn't expect to see you in my office again so soon."

I told her I didn't have to think about it any more because I had been thinking about it all my life. "Dr. Girardi," I began with conviction, choosing my words carefully, "I want to start female hormone therapy while I'm still young. Well, that is, young on the inside. Before my face starts changing. I don't want to end up looking like a man in a dress."

Dr. Girardi nodded. "I think your concerns are quite valid, Nancy," she replied. "And I do think it would be in your best interest to begin transitioning now."

She paused for a moment, choosing her words to make sure I understood.

"However," she began, "We need to discuss some concrete realities. I can't give you a magic hormone pill that is going to turn you into an older woman overnight. I believe you'll get the fastest and best results if we use a combination of different approaches. It's also very important that you understand the risks and know what to expect."

"I've read a lot about HRT on the internet," I said.

Dr. Girardi smiled and said, "I know you have. Your parents showed me your computer. But this is real life - not the fantasyland of the Internet. And since I'm your doctor, I think we should discuss the ramifications and consequences along with the benefits."

Mom and I both agreed that knowing as much as could wouldn't be a bad thing.

"There are two aspects we need to consider during your transition," Dr. Girardi said. "There's the psychological aspect of a teenage boy suddenly becoming an adult woman and there's the physical side. I don't know what you've read on the web, but female hormones aren't candy. They're deadly serious business and they will permanently alter your body."

I nodded my understanding. I knew that none of this was going to be easy, but I still desperately wanted to go forward with this. Anything to live as Nancy!

"But for right now," Dr. Girardi continued, "I want to focus on the psychological aspect of your transition. First of all, its very important that you have a support group of older women that you can socialize with."

She turned to my mom and asked, "Karen. Do you have any close friends your age that would accept Nancy's situation?"

"Yes, I do," my mother said excitedly. "Margie Jackson and Susan Estes are my two best friends. I've told them both about Darren's... situation... over the weekend and they're looking forward to meeting him as Nancy. As a matter of fact, I gave Nancy a book so that she could learn to play bridge with us."

"Excellent," Dr. Girardi said and then she turned to me and said, "Nancy, you'll need to start spending a lot of 'girl time' with your mother and her friends. It's extremely important for you to be able identify with older women other than your mother. Karen can teach you only so much, and the more time you spend with her friends as well, the more you'll feel like one of them and learn from them. That will have a profound effect on how others see you. Does that make sense?" she asked.

I told her it did and admitted that I was looking forward to it. I thought for a moment, how it would be to spend time with Margie and Susan as Nancy. To be treated as one of them... one of the girls. I shivered with excitement at the thought.

"Excellent," Dr. Girardi said. "Now we need to get a little more personal. I know you're still young, but have you been able to determine your sexual preference? By that I mean do you think you might be gay, or straight, or possibly even bisexual?"

For a fleeting moment, I thought of my upcoming date with Tim Moreland and how nice it felt to flirt with him in the park. This caused me to pause for a moment before answering, a pause that wasn't lost on either my mother or Dr. Girardi.

Gathering my thoughts, I replied that I was straight and that I liked girls. I saw Dr. Girardi raise an eyebrow and jot something down on a notepad, but she didn't interrupt me.

I began to be concerned that Dr. Girardi was too ethical to prescribe female hormones to a crossdresser, and I didn't want her to see me as such. In order for this to work, she had to believe I was really transgendered. In reality, I was somewhere in the middle between crossdresser and transgendered.

I continued on, telling her what I thought she wanted to hear. "I've only had sex with girls my age," I said. "But I do have a date with an older man this Saturday night."

Dr. Girardi looked up suddenly, her interest piqued. "Now we're getting somewhere." she said. "What's this man's name?"

I thought about Tim for a moment. How comforting it was to talk to him, how he made me feel when he shook my hand and lit my cigarette. How handsome I had to admit that I found him, in spite of myself.

"Tim Moreland," I said with a fond smile. "He's about 50 years old. He's a lawyer and is divorced. He has a son who's the same age as my little brother. I met him at the park when I took Sammy to play with his friends when I was dressed as Nancy."

"That's wonderful," Dr. Girardi said. "It means you're receptive to transitioning into an older woman's lifestyle. Psychologically speaking, it's important that you fit in and feel comfortable. If I legitimately thought that becoming an older woman was going to cause you harm, I would not advise you to continue."

"I want to fit in," I said. "I want to do everything that older women do. That's why I'm learning how to play bridge, so I can play with my mom and her friends and be one of them."

"I think that's an excellent idea," Dr. Girardi said. "What about your expectations for you appearance?"

I told her I didn't understand the question.

"If I may be blunt, do you want to look like a drop dead gorgeous porn star or do you want to look like an average housewife?"

Now that I understood the question, I didn't hesitate in answering it. "Neither. I mean, Of course I want to look pretty but I don't want to look like a porn star. I want to look like a real woman. You know like my mom." I looked over at my mom and said, "No offense, Mom. I think you're the most beautiful woman in the world, but you don't look like a porn star."

Mom smiled, squeezed my hand, and assured me that she wasn't offended.

I turned back to Dr. Girardi and passionately described the way I wanted to look. "I don't have kids and I know I'll never give birth, but I want to look like I had kids. I even told Tim that I had a daughter in college. I'd want to have big wide hips and a large butt. I want my body to be soft and curvy. I also want to have big boobs like the size of these breast forms," I said as I squeezed my left breast. "They should be pert though, like a girls. I want them to look like I used them for feeding babies. And my arms! They're too lean and muscular. I want them to be bigger but without any muscle definition."

"What about your skin?" Dr. Girardi asked. "Your make-up is wonderful. I'm assuming you used something like latex to create the wrinkle effect, but your skin is too young looking. It's too smooth and tight to pass for a woman your mother's age."

"I know," I said excitedly. "Is there a way to change that?"

"There are three things you can start doing right now that will age your skin and you're already doing one of them," Dr. Girardi said. "I read your patient information file and saw where you've started smoking."

I couldn't see myself in the mirror, but I was sure my expression went from excited to distraught. Was Dr. Girardi going to lecture me to quit smoking?

"As a doctor, I can't say anything positive about smoking," Dr. Girardi said. "As a matter of fact, I highly recommend you stop as soon as possible. In fact, Karen, I'm a little disappointed that you've allowed it."

Mom slouched defensively in her chair.

"She didn't at first, doctor," I said, coming to her rescue. "In fact, she was totally against it. However, it's such a part of my identity as Nancy, she eventually gave in."

Dr. Girardi scowled slightly. "I understand. That being said, your smoking is going to play a role in how we approach your hormone therapy. At the moment, though, we're talking about aging your skin, and smoking will definitely do that for you."

"Really," I said. "What about the other things I can do?"

"Sun light is terrible for the skin," Dr. Girardi said. "If you want your skin to appear older, you should probably become a regular tanning bed customer. I think it would also help to wipe ammonia on your skin every now and then. Don't over do it because you'll burn your skin, but it will help with the aging process."

My mother spoke up and asked, "How long would it take before she could stop using the late applicances she's wearing now?"

Dr. Girardi thought for a moment. "Without cosmetic surgery? I'd say two or three years if she puts a lot of effort into it. Without much effort, though, aging process will still happen, but at a slower rate. It might take up to ten years or more before she'll be able to live her life without using extreme make-up."

She looked at me to emphasize her point. "It's entirely up to Nancy how long the aging will take. She could do it naturally or she could get immediate results from a plastic surgeon. In the meantime, we need to talk about HRT. Under normal circumstances, I'd prescribe estrogen, progesterone and antiandrogens. However, since Nancy is a fairly heavy smoker, we should probably take a different path. Large does of female hormones and smoking just don't mix. I'm not saying it will give you cancer, but it greatly increase your chances."

"Does this mean Nancy should quit smoking?" my mother asked, a hint of motherly concern creeping in to her voice.

"By all means, if this were a perfect world," Dr. Girardi said, "However, this isn't a perfect world. Do your friends smoke?"

"Margie and Susan, my best friends, do," my mother said.

"I see," Dr. Girardi said, and then she turned to me and said, "Nancy, why did you start smoking?"

I used the canned answer that my mother and I had prepared earlier. "I was nervous about people seeing me dressed as a woman," I said, "I thought smoking would help relax me."

Dr. Girardi frowned. "I don't buy that for a second," she said sternly, tossing her pen down on the desk and crossing her arms over her chest. "Smoking make you think you're relaxed and at ease, but I don't think that's the reason you started. You're an athlete and you're far too good at sports to make a dumb decision like that. I think it was something else that made you start."

"Well don't look at me," my mother said. "I never wanted either of my sons to smoke Their father and I preached against it from the time they were old enough to walk."

"I know you didn't want Darren to start," Dr. Girardi said, "But you did play a big role in it, even though you didn't intend to. You're his role model. He looks up to you an he's always wanted to be like you. Nancy started smoking because you and your friends smoke. It's an identification mechanism, a way to connect with you and your friends."

I groaned silently because I didn't like the way things were going. I knew my reasons for wanting to be a woman and for wanting to smoke were suspect, which is why I'd been stingy with the information.

Dr. Girardi continued, still in her stern mode. "My job as a psychiatrist is to answer the questions of how, what, and why. I then take those answers and try to form the best possible outcome for my patient. As a medical doctor, I don't like that Nancy is smoking, not one bit. However, as a psychiatrist, I understand that smoking is tied to Nancy's body image, and thus her success as an adult woman."

She got up from her chair and walked around the desk to stand in front of me. She leaned back on her desk.

"We wouldn't be having this conversation if I wasn't absolutely certain that Darren needs to be female. And, speaking on the record, he is not transgendered in the classical sense. His 'hows, whats and whys' are vastly different from any of my other patients. That doesn't make them wrong, just unique to Darren and Nancy.

"I'm not in the business of changing boys into girls. I don't encourage or support my patients transitioning unless I believe it will improve their lives. I'm sure you saw those two children in the waiting room. The girl was a boy who needed to be a girl. The little boy, however, does not need to be a girl. He's here because his mother wants a daughter. I'm not treating her son, I'm treating her. I'm telling you this because I want you to know that I don't take Darren's situation lightly.

"I truly believe there will be devastating consequences if Darren grows into a man. His feelings and urges about becoming an older woman are permanent. By ignoring his needs, we'd be setting him up for regret, depression, broken marriages, and possibly even suicide.

"Unfortunately, he'll face the same risks if we allow him to transition into a woman who meets our criteria instead of his own. I'm convinced Darren needs to be a woman. I'm also convinced his nature will prevent him from finding happiness and success as a woman unless he's allowed to pattern his life on yours," she said as she looked at my mother.

"But don't you think she should be her own woman instead of a carbon copy of me?" my mother asked.

"No, I don't," Dr. Girardi said, "And this is why. Nancy is my patient and she knows she needs to be like you. Whether you believe it or not, you're my patient too. I understand you're grieving over this but I also expect a part of you is very excited and even flattered. My job for you is to help you accept and enjoy your son's transition with pride and joy instead guilt and remorse. Do you understand that?"

My mother nodded. "I understand, but I feel like you're making it too easy on me."

"This is happening because of you," Dr. Girardi said, "But it's not your fault. There's no reason for you to feel guilty, but I do need for you to be happy for Nancy. And I need for you to start seeing her as your friend and your peer. Do you think you can do that for Nancy?"

Mom sniffed and wiped a tear from her eye. "Of course I can. I've already started. I just love her so much, I'll do anything for her," she said.

"And as for you," Dr. Girardi said as she turned her attention back to me, "Don't think you can pick and choose the parts of your mother that you want to be like and disregard the rest. I know that would be convenient and fulfilling in the short term, but we need to focus on the long term because that's what this is about. We're not talking about you becoming a woman for summer vacation and then flipping a swtich and going back to being a boy when school starts. We're talking about you becoming a woman for the rest of your life. Look at your mom and think about her. I mean it, take a look at her."

I looked at my mom.

"How old is she?" Dr. Girardi asked.

"46," I said.

"Is she fat, skinny, or somewhere in-between?"

I studied Mom for a moment, not wanting to answer the wrong way. Of course, she was neither fat nor skinny. "She's in-between."

"Describe her habits and some other things about her."

"She smokes. She drinks coffee. She likes an occasional margarita or glass of wine. She likes ice cream. She hangs out with her friends a lot."

I smiled at her. "And she's completely obsessed with keeping the house clean."

Mom laughed and squeezed my hand. "I try."

Dr. Girardi nodded. "I see. And who is she married too?"

"My dad."

"And he's a man?"

"Of course!"

"Describe your father's habits and some other things about him."

That answer didn't come quite as naturally as the one for my mom did. I had to think for a moment. "He likes beer and watching sports. He plays golf on the weekends when he can. He eats too much sometimes. He loves his family. He's going bald on top. He works a lot. I know there's probably more but I can't think of them right now."

"Does your mother love him?"

"Yes."

"Does you mother have children?"

"Yes. Me and Sammy."

"Do you want to be like your mother?"

I looked at Mom admiringly. "Yes. More than anything in the world," I said, hoping they both understood how much I meant it.

"Then you have to be like her all the way," Dr. Girardi said, "Which means you'll need to be open to the idea of marrying a man some day and having a family."

I should have seen that coming, but I didn't. I was overcome with a cold chill and I felt sick to my stomach. I had always imagined myself as an older woman and sometimes I'd even fantasized about having sex with men, but those were just fantasies because I really didn't feel that way. I had never imagined myself being married to a man and having a family of my own.

I started to understand Dr. Girardi's comments about consequences. I was just picking and choosing the parts about my mom's life that I envied. I was thinking about the short term instead of the long term. I was thinking about the thrills of breaking taboos instead of being happy and productive on an everyday basis.

I was now seeing the big picture. This wasn't about me being "like" a woman. This was about me becoming a complete woman for real and I was playing for keeps. I felt completely overwhelmed, but at the same time hopeful and happy, even though I was scared to death at the same time.

"Do the both of you understand what I'm saying?" Dr. Girardi asked.

My mother and I both nodded.

"That's good," Dr. Girardi said. "That means I can take off my psychiatrist hat and put on my medical doctor's hat. We need to come up with a solution that will allow Nancy to become the woman she needs to be without the female hormones starting a war over her smoking. Which I still don't approve of, but so be it.

"I've given this a lot of thought and I think it would be in Nancy's best interest if we scheduled an orchiectomy as soon as possible. Dr. Lipinski could do the surgery and the procedure would take less than two hours. She'd still need to take hormones, but she'd get the same effect with a lower dose. Its the most economical and healthy alternative I can advise."

I'd never heard the word orchiectomy before so I asked what it meant.

"It's the medical term for castration," Dr. Girardi said calmly.

Again, I should have seen something like this coming, but I didn't. I was shocked, surprised and very scared. "So getting castrated is when they cut off your penis?" I asked.

Dr. Girardi laughed. "No, Nancy. Your SRS surgeon will do that later. Castration means removing the testicles from your scrotum. You probably call them 'nuts' or 'balls'. It's a simple procedure but also a very important one. Your doctor will need to leave enough skin for your SRS surgeon to be able to create a vagina for you."

My mother asked some questions while I digested what Dr. Girardi had said about a surgeon making a vagina from my leftover scrotum. I'd never thought about getting a full sex change before, but Dr. Giardi was talking about it like it was on a list of things to do. Wash the car. Got to the grocery store. Get your balls chopped off. Lose your dick and get a vagina. I was horrified, terrified, and even a little excited!

"So you're saying we should start preparing our selves for a full sex change surgery," my mother asked.

"It's best to have SRS done within two years of the orchiectomy," Dr. Girardi said. "You could wait longer, but I don't see any benefit to putting it off. Skin around the scrotum tends to shrink noticeably within two years of castration. Nancy's surgeon will need as much scrotum skin as possible to make a vagina for her. The extra skin will also make it easier for Nancy to reach sexual climax when a man has intercourse with her. I will warn you that SRS isn't cheap but you will be saving a lot of money by getting the orchiectomy and using less hormones and blockers. Do you foresee a problem paying for SRS, because most insurance companies don't want to pay for it. And if they do pay for it, you could be in for a long wait to get approval for the surgery."

It was a good thing Dr. Girardi was talking to my mother because I was speechless. Dr. Girardi was talking about me getting a vagina and being fucked by a man. I hadn't thought of either of those things that day in the kitchen when Mom said she was going to help me become an older woman. I was obviously scared but on the other hand, having a real vagina of my own would make me that much more like my mother and her friends.

"I don't think we'll have a problem paying for the surgery," my mother said. "My husband's mother left a very sizable trust fund for Darren and Sammy after she died. They were supposed to use it for college, but my husband and I gave Darren the choice of using it for college or becoming a woman."

"I'm relieved to hear money won't be an issue," Dr. Girardi said.

"How long will something like this take?" my mother asked. "I know you said we can get Nancy the orchiectomy now, but doesn't a person have to wait at least a year before she can get a full sex change?"

"In this country, a year is fast track," Dr. Girardi said. "It usually takes two years or more to get approval for SRS. That's why a lot of my transgender patients opt to have the surgery done outside the country. I'm not suggesting rushing into this, but you asked how fast it could happen. If everyone was agreeably impatient, Nancy could get an orchiectomy and cosmetic surgery during the Thanksgiving holidays in Mexico. She could then go back over Christmas and get her SRS. But as I said earlier, I'm not suggesting or encouraging this."

"Why wouldn't she want to do it as fast you described?" my mother asked.

"Speed transitioning wouldn't be a problem from a medical standpoint. I'm more concerned about Nancy's psyche. I wouldn't want her body rushing into something her mind isn't ready to handle."

My stress level jumped off the chart! I hadn't even been thinking about getting breasts of my own until the summer and now Dr. Girardi was saying I could have the body of a woman by Christmas!

"If I had the surgery down in Mexico this Christmas, could the doctors make me look older too, you know with aging the skin and all the weight in the right places?" I asked.

"Absolutely, and they should. They could age your skin without you having to risk skin cancer in a tanning bed," Dr. Girardi said. "Of course you'll still need to take female hormones."

"How long will he need to take the hormones?" my mother asked.

"Until she's 52 and that's in Darren's birth years - not 'Nancy' years," Dr. Girardi said. "And another thing, once Nancy starts taking female hormones, she can't stop, especially if she gets an orchiectomy. Stopping HRT could be very damaging to her health."

"What happens if I get the orchiectomy and put off getting the sex change?" I asked. "Will I still be able to masturbate if I don't have balls?"

Dr. Girardi asked me how many times a week I masturbated.

"I don't know, but its about 3 times a day so I guess that makes 20 times a week maybe."

"You have a high sex drive," she said. "But it will probably diminish considerably after you're castrated."

"But can I still have orgasms?" I asked.

"I can't say for certain because everyone is different, but it is possible. However, you'd definitely have to work harder at it than you are now, which is why I think you'd benefit from anal stimulation."

"Anal sex?" I asked.

"Yes, until you're vagina has been dilated enough for penetration. With a little practice, you can learn to stimulate your prostate region and I suspect that kind of orgasm would be more rewarding than masturbation with your penis. Unfortunately, the opportunity for anal orgasms won't last forever because female hormones shrink the prostate."

"Are you saying that Nancy's best hope for having orgasms is by having sex with a man as a woman?" my mother asked.

Dr. Girardi nodded at my mom. "Vaginal intercourse with either a man or a device will provide the most sexual relief for Nancy. And given her age, even with the reduced libido, she's going to desire sex more frequently than genetic middle-aged women."

"If that's the case, I don't see the point in putting off her surgery in Mexico. SRS sounds like something she should do right away," my mother said.

"I think I'd have to agree with you," Dr. Girardi said.

"Can she get castrated in Mexico at the same time as her SRS?" my mother asked.

"No. Nancy's body is going to need some time to make the adjustment from male to female hormones. Her SRS recovery time would be faster and less painful if you could wait at least three weeks after the orchiectomy."

"Of course there is school to consider. I don't think she'd want to go back to school after Thanksgiving with breasts," my mother said.

"If Nancy is going to do this right away, it would be in her best interest to drop out of school and start working on getting her G.E.D." Dr. Girardi said.

"I was thinking she could get her real estate license like me," my mother said. "And she'd need a high school diploma or a G.E.D. before she could take the Realtor's exam."

"What about football?" I asked. "We got one more regular game left and then we start playoffs."

"Football should be the least of your worries," Dr. Girardi said. "You'd be weaker and less aggressive if you started therapy before the season is over. Or you could wait until the season is over before you begin therapy. But as I was saying, football should be the least or your worries."

"But I made a commitment to my coaches and the team," I said.

"Your commitment didn't prevent you from taking up smoking. Did it?" Dr. Girardi asked.

"No," I said sheepishly.

Dr. Girardi sighed and said, "All of the choices we've been discussing are up to you, Nancy. I can't tell you what to do or when to do it. However, I don't think its good for your mental health to have one foot in football cleats and the other in high heels at the same time. I think that if you want to play football, you should stop dressing up as a woman until your season is over."

"That makes a lot of sense," my mother said. And then she turned to me and said, "You have a lot of things to think about, Honey."

******

Mom and I left Dr. Girardi's office with a prescription for low dose estrogen, progesterone and an androgen blocker.

The unspoken race to find our cigarettes began as soon as were seated and buckled in. For the first time in my life I understood what it felt like to need a cigarette. Lighting my cigarette was neither a choice or a habit. It was all about self preservation. It was official, I was a nicotine addict just like my mom and her friends.

The original plan was for me to go back home and change for school, but I was having a lot of second thoughts about that. My session with Dr. Girardi had been intense and I was still in a state of shock. I remembered what she said about football and how it should be the least of my worries.

I blew a puff of smoke out the window and said, "I don't want to go back to school today."

"It's okay, honey. I don't blame you. What about tomorrow?"

"I don't know, but I don't think so. There's too much to think about," I said. "There's no way I'd be able to concentrate in class after today."

"I know we talked about you leaving school after this year, but I'm starting to think it might be best if you dropped out now."

"Maybe. I don't know," I said. "So what do you think about me getting a sex change operation over Christmas in Mexico? Do you think its too soon?"

"I think it's fast but I don't think its necessarily too fast. It does sound like it would save a lot of money if you're sure you want to do this, but I wouldn't use money as a reason for your decision. It's hard to believe that you can be just like me in less than two months. You'd be going from 16 to 46 in the blink of an eye and you wouldn't be able to go back- ever. You understand that, don't you?"

"I do and it makes me feel good when I think about it."

"You're not scared?" my mother asked.

"Are you kidding? I'm freaking petrified. I mean, I want it like I've never wanted anything in my life, but the crazy thing is, and I've never said this to you before, but I don't know why I want it. I just know that I do."

"Really?"

I shrugged my shoulders and said, "Yeah, really. It's the honest to God truth."

"Then why are we even talking about doing this if you don't know why you want to do it?"

I asked her if she remembered Dr. Giardi saying that I wasn't classically transgendered.

"I heard her say that, but I didn't know what she meant."

"She was saying that I'm not like a girl living in a boy's body the way most people think about transgendered. But she said I still needed to be a woman and that meant so much to me when she said that. You don't know how guilty I've been feeling because I'm not like what people think I should be like. I'm different and I've got different reasons for wanting to do this. Some of them I don't even understand, but Dr. Girardi said that was okay. It made me feel that I'm not any less of a person for wanting the things I want."

"Are you telling me that you're willing to change your entire life for something you don't really understand?"

I took a puff from my cigarette and exhaled out the window. "That's exactly what I'm saying. And Dr. Girardi was saying I'm not crazy for feeling like that."

"But this is such a big thing!" my mother said. "Shouldn't you wait until you know this is really right for you before you go out and do it?"

"That's the thing. It is right, I just don't know why it's right. And Dr. Giardi understood that. I was kind of hoping you would too."

Mom finished her cigarette and threw it out the window. I could tell she was thinking of something to say as she went about the business of replacing her cigarette. I took advantage of the pause in conversation to do the same.

"Do you think it would help if you got a second opinion?" my mother asked.

"From who? Another psychiatrist?"

"No, I was wondering if it might help to talk to Margie and Susan?"

"Mrs. Estes and Mrs. Jackson?"

"I know they're not psychiatrists but they are women," my mother said. "I just think it might help to have another woman's point of view, other than mine."

"Sure! I'd love to talk to them, but are you asking because you're not behind me doing this any more?"

Mom shook her head and said no. "I was in there with Dr. Giardi too," she said, "And I thought everything she said made sense."

"Except for the parts you didn't understand?" I asked sarcastically.

"I don't know. Even those parts seemed to make sense because I was listening with my heart instead of my brain. If it was up to me, I'd drive you down to Mexico today because I believe with all my heart that you need to be a woman, honey. An older woman like me and Susan and Margie. But it's not up to me."

"That all I wanted to hear you say, Karen. I just wanted to make you sure you didn't change your mind."

"Well in that case, I'll call Margie and Susan tonight and ask them to come over tomorrow. If you don't mind missing another day of school."

"That would be fantastic," I said. Then I smiled. "And not for just missing school."

Mom grinned. "I also think we should talk to your Dad about this when he comes home tonight."

"What? You think I should ask him if he thinks I should get a sex change?"

"He expects you to get a sex change at some point. He just doesn't know you're thinking about it so soon. He loves you and he supports you, but this is hard for him. I just think you should show him a little respect by talking to him about it."

"You're right," I said. "I didn't mean to act like a jerk about it."

"Good," my mother said as she pulled into a drug store parking lot. "I'll call him at work and suggest to him that he takes you out to dinner so that the two of you can talk in private."

I paused for a moment. Go out to dinner one-on-one with my father as Nancy? I was a little nervous, but thought it might be a good test run for my date with Tim Moreland. Not that it would be a "date" with my dad, but it would give me an insight into having dinner with an older man as an adult woman. I tossed my cigarette aside and followed my mother into the pharmacy.

After getting my prescription filled, we walked to the front of the store where mom purchased a carton of Marlboro Light 100s for herself and a carton of Virginia Slims Menthols for me.

She handed me my cigarettes and my prescription and said she felt a lot better about me smoking after Dr. Girardi explained the benefits of taking lower doses of my medication.

*******
The first thing Mom and I did once we got home was to celebrate as I swallowed the first three pills.

"You know you'll be doing that every day for the the next 36 years, right?" she asked.

I told her I was looking forward to making a habit out of it. Anything that would bring me closer to my dream of being Nancy full-time.

The next thing I wanted to do was to look at naked women on the the computer. It wasn't because I was horny. I wanted to look because I wanted to see what I was getting into. I had thousands of pictures of older naked women stored on my hard drive. But to tell you the truth, I'd never really studied the anatomy of an older woman from the perspective of really being one.

I knew there was no way to do it without getting caught by mom, so I did something brave and asked for her permission.

"I think that's a good idea," she said. "Would it embarrass you if I looked with you? Or is this something you need to do in private?"

I hadn't really thought of my mother looking at porn with me, but then again, I wasn't going to do it to get off. I was doing it because it was like homework. "I'd like that if you don't think it will bother you," I said.

Mom laughed and asked why it would bother her. "Those women don't have anything that I don't have. God made women standard with boobs and vaginas."

********

My mother and I smoked cigarettes and looked at pictures of naked women in their 40s and 50s for the next hour. It helped me come to terms with the idea of having a vagina instead of a penis. It also gave me some perspective on what I'd really like my body to look like.

We narrowed it down to five pictures of different women who basically had what I wanted.

"Maybe you should save them to a folder and email them to Dr. Giardi," she said. "That way she can send them to the doctors in Mexico."

It sounded like a good idea to me and I did it just like my mother said. As I was attaching the folder to Dr. Girardi's email, I wondered if anyone else had ever sent her naked pictures.

"I know you need to sleep on this for a couple of nights," my mother said, "but what do you think so far?" she asked as she lit a cigarette. "Are you sure you want to look like those women?"

"Actually I want to look like you, but I didn't want to ask you to take your clothes off."

Mom laughed and thanked me for sparing her the request.

I told her I couldn't stop thinking about having a real vagina like hers. "I'm really going to be just like you," I said in disbelief as I lit a cigarette for myself.

"I think you already are like me," she said, "But I do think you'll feel better about your self as a woman once you have a real vagina."

I was telling her how much I was looking forward to it when Sammy came in from school.

Our greetings were cordial enough. Sammy wasn't treating me like a space alien, but at the same time, he wasn't responding to me as if I was his older brother anymore. I supposed that was good, but it was also a little bothersome.

If I had to describe Sammy's reaction to me as an older woman and a smoker, I'd say he was "curious."

He told mom and I about his day and we told him about our visit with Dr. Giardi.

"How are you going to pee if they cut it off?" Sammy asked.

Mom told him it wouldn't be a problem because women sit down when they use the toilet.

******

My night out with Dad started out awkward. He took me to a restaurant about 15 miles away from our house. I'd been there before and the food was good, but I was pretty sure he chose it because we wouldn't see anyone we knew, and that was fine by me. It just made for a long car ride and a lot of silence.

As much as I enjoyed looking like a woman, I couldn't get comfortable in front of my dad. I felt like a sissy and a disappointment.

After we were seated, he ordered a whiskey and soda. I ordered a glas of Chardonnay. Dad didn't say anything, so I supposed he was fine with me ordering an adult woman's drink.

We sat in silence for a couple of minutes. I then broke the ice by thanking him for all his support. "I know this is hard for you," I said, "And I'm sorry for putting you through it."

"You don't have to apologize," my father said. "I'm the one who should apologize to you. I was a real ass to you when you were younger and I'm real sorry for that."

"It's okay, Dad. You were just doing what you thought was best for me."

"No, I wasn't," my father said. "And thats why I need to apologize. I knew from the start that you wanted to be female, but I did everything I could think of to change your mind. I did the same thing to you that my father did to me."

I choked on my father's words. Was he saying he did the same kind of stuff that I did? Was he saying he was a crossdresser or maybe even something else? "What do you mean?" I asked. "What did your father do to you?"

Dad rubbed his face and shook his head and then he looked me. "You've got to promise me that everything we talk about tonight stays between you and me. And that goes for your mother too. I don't want her hearing about any of this."

I was totally creeped out but I promised to keep his secret- whatever it was.

"I know you want to be like your mom," Dad said. "But its not your mother's fault. It's mine. I'm the reason you feel the way you do. I guess it must be some kind of genetic thing. You're not just like your mother. You're exactly like me."

"What are you trying to say?" I asked. "Do you want to be a woman too?"

"No, not any more. I love my life now as a father and a husband, but when I was your age, I think I probably felt exactly the same way that you do now. Except I wanted to be a girl, I didn't want to be older like you do."

I told him that I didn't believe him. "You're just saying that because you're trying to make me feel better about what I'm doing."

"No. I'm telling you the truth, Nancy. When I was your age, I called myself 'Debbie'. I started wearing my mother's clothes when I was probably 8 or 9. Sounds familiar. Doesn't it?"

I couldn't answer him because I didn't know what to say. The thought of my father doing the kinds of things that I was doing made me sick to my stomach. The man whom I'd respected and looked up to all my life was a sissy like me.

"I punished you because my parents punished me. I tried to make you feel bad because they made me feel bad. I thought they did the right thing because I grew up and became a man and raised a family. I thought I could make you do the same thing."

"What made you change your mind?" I asked.

"A lot of things, but I think jealousy played a big part in it," my father said. "After a while, I realized I was trying to make you stop and turn you around because I was jealous of you. I didn't want you to get what I couldn't get myself when I was your age. I didn't recognize it at first. I just thought I was doing the right thing. But then when I realized I was jealous of you, it made me feel bad and I wanted to fix it."

"Did you really want to be a girl?" I asked.

"Yes I did. And every time I look at you, I think about what my life could have been like, if my parents had been more understanding. I regret not being able to be a girl but I don't' regret being yours and Sammy's father and I don't regret being your mother's husband."

"Dad, can I ask you something?"

"Sure."

"Are you gay?"

"No. But I think I know why you asked. You're scared about being a woman and having relationships with men. Aren't you?"

"Yeah, I am."

"I don't know what to tell you Nancy. You're in a strange place. You're a guy who wants to be a woman, but you're not gay. Are you?"

"I don't think so."

"Then you're probably not."

"But I think about it sometimes," I said. "You know. Being with men."

"I don't think there's anything wrong with that," my father said. "I think it just proves you're serious about being a real woman."

"I've never kissed a man before."

"Neither have I," my father said, "But I think it would be very normal if you did."

"Don't you think that's kind of gross?"

"To be perfectly honest, I do think its gross, but then again, I'm a man and you're about to become a woman. The rules are going to change for you. If you can keep an open mind about it, you might even grow to like it."

"I don't know. Maybe," I said. "It's just that I know I look like a woman on the outside, but on the inside I'm still a boy."

"I get that," my father said. "And I don't think its going to be easy for you because I know it wouldn't be easy for me, but I also think you'll be able to do it when the time comes because you've been able to do everything else. I think you're very courageous and I'm very proud of you," my father said.

I told him about my session with Dr. Giardi and we talked about it over dinner.

"What do you think? Does it seem to fast?" I asked.

"It is fast, but that doesn't make it wrong. However, I think it would be less overwhelming if you just focused on the orchiectomy for now and let all the other pieces fall into place when the time comes."

"What do you think I should do about football and school?" I asked.

"Do you still like playing football?"

"I love it, but right now it doesn't seem as important as it used to. I skipped practice today and I'm going to skip again tomorrow. Mrs. Jackson and Mrs. Estes are coming over and I'm supposed to do woman things with them."

"And doing woman things with the girls is more important than playing football. Isn't it?" my father asked.

"It feels like it," I said.

"And I assume you feel the same way about school."

"It gets in the way big time," I said.

"Do you think you'd feel better about things if I told you to quit the football team and drop out of school?"

"I think I would," I said, "because if you told me what to do then it wouldn't have to be my choice and it wouldn't be my fault."

"Sorry, but I can't let you off the hook so easily," my father said. "Your mom and I will support anything you decide but you've got to be the one to make the decisions."

"Why? Because you don't want me blaming you if this doesn't work out?"

"That's the idea," my father said with a warm smile.

******

I had gone without smoking the entire time I had been with my dad out of respect for him and fear of his disapproval, but as the waiter removed the dishes from our meal, my body began screaming for a dose of nicotine. I surrendered to my withdrawal symptoms by cautiously removing the cigarette case from my purse. "I'm sorry Dad, but I really need a cigarette right now," I said as I daintily extracted a Virginia Slim cigarette from my case. "Do you mind?" I asked nervously as I placed the menthol cigarette between my lips.

"Not at all," he said as he picked up my lighter and held the flame for me. "By the way, you don't have to be embarrassed about smoking in front of me."

I blushed as I exhaled away from him. "I'm trying not to be but its hard," I said.

"You'll get used to it and so will I," my father said. "It's just going to take a little time, but for what it's worth, I think you look very attractive and grown-up when you smoke."

"Really?" I asked excitedly. "Do you really think so?"

It was my father's turn to blush and so he did. "Yes I do," he said, "and I hope you don't think that makes me a pervert or a bad person, but I've always had a thing for attractive women smoking. I guess that's one of the reasons I started dating your mom."

"That's amazing," I said. "I can't believe it."

My dad apologized and said he was out of line. "I never should have said that," he said. "I don't know what got into me. I know its an unhealthy addiction and women don't smoke so that men like me can get their jollies. Please forgive me."

"No Dad. Its okay. Its not like that. When I was a guy, I felt the same way about women smoking as you do. As a matter of fact, that was a big reason why I started."

The expression on my father's face changed from ashamed to confused. "But I thought you started because it helped you relax because you were nervous about wearing women's clothes."

"Yeah, kind of. I mean it does help with that," I said. "But the reason I started in the first place was because I wanted to be like Mom and smoke like a woman."

Dad grinned and shook his head from side to side. "Oh my God," he said. "You really are just like me."

"What do you mean?"

"Once again, any thing I tell you about this has to stay between the two of us. You can't tell anyone. Do I have your word on it?" he asked.

I promised to keep his secrets to myself and take them to my grave.

"I think I know what you mean about wanting to smoke like a woman," he said. "Back when I was a boy during my crossdressing years, I used to pretend to smoke like my mother. Of course I never actually lit a cigarette or smoked it for real, but I pretended I was. Do you think maybe you were doing the same thing?" he asked.

My heart raced as I tried to keep my brain from exploding. I did know what my father was talking about and I told him so. From a general perspective, I knew I wasn't alone in my feelings because I'd read about others like me on the web. However, I never thought I'd meet someone like me face to face and I certainly didn't expect that person to be my father.

"So you never tried smoking?" I asked, "not even with Mom?"

Dad shook his head and said, "I couldn't because I didn't feel worthy."

I gasped because I knew exactly what he was talking about. "Me too!" I said excitedly. "I wanted to but I couldn't. It just didn't feel right."

"Is that just to weird that we'd both feel the same way?" he asked.

I immediately agreed with him and asked him a question of my own. "How come some guys can smoke and get away with it like its no big deal?" I asked.

"I don't know," my father said. "But they can. It's like some guys can smoke like men, but others can't and they have to smoke like women, or they just don't do it at all."

I picked up my cigarette case and tried to hand it to him. "Do you want to try one now?" I asked.

Dad smiled sadly and said," Thanks for asking, but I can't. It just wouldn't feel right and your mother would kill me if she ever found out. Speaking of your mom, we better get back before she thinks something happened to us."

Like Mother Like Son 9

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Caught with Consequences
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • Estrogen / Hormones
  • Hair Salon / Long Hair / Wigs / Rollers

Other Keywords: 

  • older women envy
  • Mother Admiration

Permission: 

  • Posted by author(s)

16 year old Darren Peterman is introduced to his mother's best friends as 46 year old Nancy Peterman. Thanks to my editor and friend, Victor G.

*************
Chapter 9
************

Eight o'clock Wednesday morning found me sitting in my bedroom in front of my new vanity mirror, excitedly undergoing another transformation into the beautiful, middle-aged Nancy. Normally, I'd be at school sitting in first-period home room and bored right out of my skull.

But I wouldn't be bored this morning, I thought with a grin as I pulled a tight-fitting nylon wig cap over my boyish brown hair, tucking away any stray hairs. There was far too much waiting for me - well, for "Nancy" - today for me to be bored at all.

Once my hair was completely hidden away under the wig cap, I began applying latex wrinkles around my eyes, carefully working them into place with a gentle adhesive. Once I was satisfied with the aging illusion they accomplished, I worked another set of fake wrinkles into place near both corners of my mouth. Once my entire set of wrinkles were set and properly adhered, I studied my work in the mirror. I adored how they made me look so much older, the first step in becoming the middle-aged woman that I deeply longed to be.

Feeling what was becoming an all-too-familiar craving for nicotine, I reached for my elegant Louis Vuitton cigarette case and pulled out a menthol Virginia Slims. I placed it into my mouth and lit up, taking a deep, satisfying drag. I held the smoke in for a few moments then tilted my head and exhaled luxuriously toward the ceiling, perfectly mimicking the actions of an older woman who'd been an addicted smoker for many, many years. Thankfully, my gaffe was already in place to keep my stiffening boyhood in check.

As I watched myself smoke, gently teasing myself with my mature, feminine actions, I realized this would be two days in a row that I had skipped school and gone AWOL from practice. Coach Holloway would be pissed, and probably take it out on me when I returned to practice, but it didn't matter. Today I wasn't Darren, I was Nancy. I was an adult woman with adult habits and responsibilities. I'd deal with Darren's adolescent problems another time.

I pushed aside any thoughts of recriminations waiting for me at school and continued my transformation. I set my cigarette down in an ornate crystal ashtray Mom had let me borrow and started on my foundation makeup. I dabbed a generous layer on a sponge and began applying it to my face, taking the occasional drag off my cigarette as I worked. As Nancy, I wore slightly heavy yet smooth, well-applied makeup to help perpetuate the illusion that I was an older woman skillfully using makeup to attempt to hide her age. A disguise within my disguise, as it were.

As I diligently altered my face from that of a teenaged boy into Nancy's prettier and considerably older one, I thought about my father and the things he said the night before. As hard as I tried, I couldn't picture my manly father prancing around in a dress and wanting to be a woman, but here I was doing the same thing. Maybe he was right about this being a genetic thing. If it was true, it shed a whole new light on my situation.

If my wanting to be a woman was really genetic, then that meant it wasn't my fault. Of course, I still owned all of the responsibility. My father said he felt similar feminine urges as a boy, yet he resisted becoming a woman. Why couldn't or wouldn't I do the same?

Did my father resist or was he not allowed to become the woman he wanted to be? It was the latter, but he still had a choice. Didn't he? He could have waited until after school, but he met Mom in college, and that must have put a lid on his becoming anything other than what he is now. But what about his regrets? It sounded like he had them, in spite of how happy he seemed with our family, which is why he was encouraging me to follow my dreams.

My father's revelations were a mixed bag of regret, understanding, and desire, but his bag had been camouflaged with a blanket of manly accomplishment.

My dad understood everything I was doing, probably better than my mother did. For all I knew, he understood me better than I understood myself. That came as a big surprise to me and I wanted to tell someone. Telling someone else would exonerate me from all the craziness I was feeling, but of course I couldn't do that. I couldn’t tell anyone, not even my mother. I'd made a promise to my father, and I'd keep his secret.

I was thankful to him for filling in some of the missing pieces to the puzzle of my life. The way he talked about it made me think that maybe my reasons for wanting to be a woman were genetic. Thinking about it like that eased some of the guilt I was feeling, but it didn't erase it.

My father had overcome his urges, but I was giving in to mine at a break-neck pace. Although I hadn't made any definitive or permanent decisions yet, I was racing toward older womanhood with open arms. My parents supported me wholeheartedly, so the only thing that could get in the way of my blossoming into an older woman was me.

After my foundation was finished, I lit a fresh cigarette and started on my eye makeup. I'd been practicing my makeup application skills the past few days (well, months really, when no one was home), and Brenda and Mom had been very good teachers, so I felt confident enough to try this on my own. I did a pretty good job outlining and painting my eyes and painstakingly coating my lashes in dark mascara. When I was finished, I was happy with the alluring way my eyes looked, especially with my green-tinted contact lenses in place.

I then went to work on my lips, outlining them and filling them in with a lovely rose color so that they looked fuller and more luscious. Seeing the color of my lipstick ringed around the white filter of my cigarette made me feel even more like an adult woman. I loved it!

I finished my makeup with blush and powder, and then carefully painted my false long nails in a shade to match my lips. While my nails dried, I lit another cigarette and watched myself in the mirror. I hoped with all my heart that Mrs. Estes and Mrs. Jackson - Mom's best friends - would accept me as one of their own. I prayed my appearance, voice, and mannerisms would be enough to convince them to let me into their inner circle of middle-aged femininity.

Once my nails were dry, I picked an outfit stylish enough to wear to meet the ladies. I carefully pulled a pair of sheer panty hose over my smoothly shaven legs, adjusting the control top over my padded girdle. I slipped a lacy white camisole over my head, and then followed with a button-down, cream-colored silk blouse. It took me a moment to get used to the buttons being on a different side, as is normal for a woman's blouse, but I eventually got it buttoned up. I admired the way the silk blouse fit, flattering my ample false breasts.

Next, I pulled on a calf-length navy blue skirt that also flattered my lower false mature curves, tucking in my blouse before zipping the skirt up on the side. I fastened a navy blue leather ladies' belt with a lovely, dainty gold buckle around my waist and slid my feet into matching navy blue leather designer pumps with slender three-inch heels. I pulled on a navy blue woman's suit jacket, one matching the skirt around my waist.

I looked at my reflection in the mirror. From the hairline down, I was a an elegantly-dressed, attractive, feminine, mature woman with a face of well-applied makeup, but the snug-fitting wig cap atop my head made for a slightly comical sight. I sat back down in front of the vanity and picked up my blonde wig, then secured it into place with several strategically placed bobby pins. I took a moment to carefully run a brush through my hair, styling my new long hair just right.

To complete my look, I fastened a slender gold necklace around my neck and slipped a slim gold ladies' watch around my wrist, then attached a pair of gold earrings to my ears. Maybe I can get my ears pierced soon and not have to rely on these clip-ons, I thought with a smile.

I slid my stylish women's glasses into place on my nose and gave myself a spritz of perfume. I stood before the full-length mirror for one last inspection. I had to admit that I looked great. Nancy Peterman, an attractive, well-dressed, 46-year-old woman wearing a designer suit and heels stood there. I hoped Mom's friends would see me as such and not notice any traces of the 16-year-old boy athlete I really was beneath.

I gave a sweet, feminine smile to the mirror and gracefully offered a hand in greeting to my reflection.

"Hello, I'm Nancy Peterman, Bill's sister," I said pleasantly in my Nancy voice.

I nodded to myself, satisfied with my voice and mannerisms. I looked down at the feminine watch on my wrist. My mother's friends would be here to see me in half an hour. It was a meeting I had fantasized about all my life, but was now starting to dread.

My fantasies about hanging out with my mom and her friends never included an explanation of why I was an older woman like them, I was just unquestioningly one of them. My fantasies were just that - fantasies - and they didn't need to make sense, but it wouldn't be like that today. Today I'd look like them, move like them, talk like them, even — if they’d let me - smoke like them. Would they accept me as Nancy, or would they start lecturing me about throwing my life away? Would this affect their friendship with my mom?

Of course, Mrs. Estes and Mrs. Jackson - Susan and Margie - would want to know everything. Why I'm doing this and why I want to stay like this. Did I really have the balls to be honest with them? Maybe so, I thought sardonically, but if I kept on this path, I wouldn't have my balls for much longer.

I checked my makeup one last time, tossed my cigarette case into my handbag, slung the handbag over my shoulder, and made my way downstairs to await Mom's friends.

*******

Thirty minutes later, I was in the kitchen with Mom going over what to say to her friends when the doorbell rang. I must have been more nervous than I realized, because I'd just finished my fourth cigarette in that thirty minutes. I crushed it out in the ashtray as Mom gently squeezed my hand.

"You'll be okay, Nancy. You look amazing," she said reassuringly, "Right now, you’re a woman. Don't doubt that, okay?"

I smiled in reply and squeezed her hand in return. "Thanks, Karen. You're the best friend I could have."

She smiled warmly, touched by my reply. "You ready?" she asked, getting up to answer the door.

I nodded and told her I was, even though deep down I really wasn't. Once again, I felt like that prisoner on death row walking toward his rendezvous with the electric chair. My knees nearly buckled as I stood in my heels and followed Mom to the door. I felt keenly aware of my body and the artificial padding I wore. I knew I looked, moved, and sounded like an older woman, but how could I really expect Mrs. Jackson and Mrs. Estes to accept me as one when they knew the truth?

I stood shyly behind my mother as she opened the front door. I could see Mrs. Jackson and Mrs. Estes over my mother's shoulder as the three women excitedly greeted each other. My mother stepped back and Mrs. Jackson and Mrs. Estes walked inside.

"Ladies, I'd like to introduce you to Nancy, my new sister-in-law!" Mom said proudly with a flourish.

I felt as if I might pee my girdle as Mrs. Jackson slowly approached me, studying me curiously.

"How do you do?" I said nervously in my Nancy voice, extending my femininely manicured hand, "I'm Nancy Peterman, Bill's sister."

Mrs. Jackson just grinned and gave me a big hug. "Oh my word! Darren, I can't believe it's really you!" she said as she kissed my cheek, careful not to mess up my makeup. "You look gorgeous, honey!"

Mrs. Estes appeared at my side as Mrs. Jackson took a step back. Her expression was one of shock. "I don't believe it. I thought your mother was playing some kind of game when she told me what you were up to," she said, shaking her head in disbelief, "But I guess she wasn't kidding."

"It's not a game, Mrs. Estes," I replied, still trying to calm my nerves. Mrs. Estes was my mother's age and about 5 or 6 years younger than Mrs. Jackson. She looked skeptical and maybe even a little disgusted, which made it hard for me to feel comfortable.

I paused for a moment, trying to collect myself. There was an odd silence among us, and I realized they were waiting for me to say something. I regained my feminine composure and gestured gracefully for them to come inside. "Please, do come in," I said pleasantly, "And thank you both for coming over. It means a lot to Karen and me."

Mom smiled at my graciousness and escorted us to the kitchen. She poured coffee for us all as I took a seat at the table with Mrs. Jackson and Mrs. Estes. Both women looked at me without speaking, studying me like I was at the zoo. Their stunned silence was painful. In my discomfort, I ached for a cigarette but I wasn't quite ready to cross that bridge with them just yet. Let them accept my appearance first, I thought, then the smoking.

My mother's voice broke the silence as she reminded the ladies of why she had asked them to visit. "Nancy has a lot on her mind," she said as she put two mugs in front of Mrs. Jackson and Mrs. Estes. "Her doctor thinks it would help if she talked to us about it."

"Are you sure this isn't some kind of joke?" Mrs. Estes asked as she pulled a worn leather cigarette pouch from her purse. "Because if it is, I have as good of a sense of humor as anybody. I'd just like to know before I open my mouth and say something I'll regret."

"So you don't think this is a good idea?" my mother asked as she returned to the table with coffee for herself and me.

Mrs. Estes lit a cigarette. From years of silently observing, I knew that she smoked Virginia Slims, the same brand I currently smoked, except hers were regular- not menthol. "He's a boy, Karen, and he's your son! I've known him since he was a baby and I've watched him grow up. He's no more of a woman than I am a boy!"

Her words stung me deeply. I don't know what I had expected, but Mrs. Estes's response was certainly different than I'd hoped for. Of course, maybe I shouldn't have been surprised. Mrs. Estes was kind of a holy roller, perhaps her aversion was rooted in her religious beliefs. Or maybe she just felt that way because she was a real woman, and I was boy pretending to be one.

My mother and Mrs. Jackson came to my defense. Mrs. Jackson asked Mrs. Estes to ease up while my mother tried to help Mrs. Estes understand my point of view.

"He wants to be like us, Susan, and he's wanted it for a long time," my mother said. "This isn't a game or a joke. Darren is completely serious about becoming a woman - an older woman like us."

"I can tell that from his make-up," Mrs. Estes said, once again scrutinizing my face. "It's bad enough that he thinks he wants to be a girl, but why does he want to be so old?"

I could have said a lot of things or I could have said nothing, but I chose to ask Mrs. Estes if the make-up looked real.

"Of course it does, Darren. You look completely believable. I almost had a heart attack when I saw you," Mrs. Estes said.

Mrs. Jackson removed a skinny brown More 120 cigarette from her long black leather case and lit it. My mother followed suit with one of her Marlboro Light 100s. "I think your make-up looks very nice, Nancy, and it looks so real," Mrs. Jackson said. "If I passed you on the street, I'd have thought you were just another middle-aged woman. When your mom opened the door, I wouldn't have known it was you if your mother hadn't given me a heads up."

"Thank you, Mrs. Jackson." I said, feeling relieved at her kindness.

Mrs. Jackson smiled at me and exhaled. "Call me Margie, hon. I think friends should call each other by their first names, don't you?" she asked.

"Yes, I'd like that, Margie. Thank you," I said.

"So, when did all this happen?" Mrs. Estes asked. "Seeing you like this is the last thing I ever expected. Are you gay?"

"I'm not gay, Mrs. Estes," I replied. I noticed that she hadn't yet given me permission to call her by her first name, so I didn't. "I still like girls, but…"

My mother blurted in excitedly before I could finish. "He has a date Saturday night, with Tim Moreland," she said.

Margie and Mrs. Estes both gasped.

"Wow, nice going, girl! He's gorgeous!" Margie said.

"I thought you said you weren't gay," Mrs. Estes said pointedly.

"Well, I'm not," I said emphatically, "It just kind of happened. I met him at the park when I took Sammy to play football. We started talking and then he asked me out."

"And you said yes?" Margie asked with genuine excitement.

"I did say yes," I replied hesitantly, "But it was a mistake, I shouldn't have done that. I wasn't thinking clearly, and I got caught up in the moment."

"What are you going to do if Tim Moreland finds out you're really a kid running around in his mother's clothes?" Mrs. Estes asked. "Have you thought about that, Darren?"

"No, but he won't find out," I said, "I'll be careful."

"Don't you see, Darren?" Mrs. Estes asked. "It's just not natural. God never intended for boys to become girls and he certainly didn't intend for them to become grown women. Is all that real?" She asked as she pointed to my boobs. "Did you already get a sex change operation?"

Once again, Mom came to my defense. "No, but he might someday. That's why I asked you both come over today. There's a very real possibility that Nancy..." Mom emphasized my female name with a glance at Mrs. Estes. "Might get a complete sex change by this Christmas. I thought it might help her to make up her mind if we all talked about it."

"So this is kind of like an intervention, then, right?" Margie asked. "You want us to talk him - her - out of doing this?"

"No, not exactly," my mother said. "I really believe Nancy would be happier living her life as one of us and I think she should get the surgery as soon as possible. I was thinking we could talk about our lives and the things she could expect if she were to become a woman our age."

Margie reached across the table and touched my hand. "Sweetie, why do you want to be fat, wrinkled, and old like us?" she asked. "If you have your heart set on being female, why not look like a hot to trot super model?"

I smiled. "I don't think any of you are fat or old," I said sincerely. "I think you ladies are the most beautiful women in the world and I've always thought that. You're all so mature and smart and confident. That's the way I want to be."

"Well, you and your mother could pass for sisters, even if you are claiming to be your father's sister," Mrs. Estes said sarcastically as she blew a puff of smoke across the room.

"I know! That's what I want," I said excitedly. "I want to be just like my mom in every way. I've always wanted to be just like her."

"That's so sweet," Margie said. "Imagine that! A boy who loves his mother so much that he wants to be just like her. I've never heard of anything like that before, but the thought is sweet. It's such a big change from the way you really are. And Christmas is so soon. Don't you think it might be best if you took some more time and not rushed into things?"

The phone rang before I could answer. Susan, Margie, and I watched as my mom got up from the table to answer it. "I'll be right back," she said. "Keep talking."

I started telling Margie about feeling that it was right for me to be a woman and that since I felt that way, it didn't make sense to wait.

"It's for you," my mother interrupted us, offering the cordless phone with her hand covering it so that the person on the other end couldn't hear. "I think it's your football coach."

My heart flipped in fear. "What am I going to do?" I asked. "I can't talk to him like this!"

"It's not like he can see you," Mrs. Estes said with a smirk. "Just talk to him in your real voice and see what he wants."

I stood up and took the phone from my mother. I pulled one of my clip-on earrings off and nervously held the phone to my ear. "Hello," I said, reverting back to my real voice. The ladies watched me, incredulous at hearing and seeing my teenaged boy voice coming from a middle-aged woman's painted lips.

The voice on the other end was Coach Holloway's. "You missed practice yesterday, Peterman. Are you sick or something?" he asked.

"No Coach," I replied, dreading the tongue-lashing I knew was coming.

"Then why weren't you there yesterday and why aren't you in school right now?"

I wasn't about to tell him the truth so I told him I didn't know. "I just needed some time off for some personal things," I said.

"Personal things?" he asked. "Like what kind of personal things? What do you have to do that's more important than being ready for this week's game?"

I hate to admit this, but I was intimidated. He was the coach and I was the player and when coach asks you a question, you give him an answer. If he tells you to do something, you just do it and don't ask questions. But this wasn't like other times when my coach had yelled and tried to intimidate me. Anything and everything I said was going to have some kind repercussion, so I had to choose my words carefully. I told him again that it was personal and apologized for missing practice.

Coach Holloway didn't even bother to try to hide the anger in his voice. "Okay, Peterman. This is the way it's going to be. You're coming to practice today and you're going to run wind sprints for 45 minutes after we're done. And you're not going to start the game Friday night, Brukowski is going take your place. He plays until he screws up. If he doesn't screw up, then you don't play, got it?" he asked.

He expected me to say yes, and I halfway expected myself to say it too, but I didn't. I told him that I couldn't make it to practice today.

"You better change your mind about that, Peterman. Your whole future is at stake. Those college scouts who came to see you play against Wesley are coming back Friday night."

"But you said I might not even get to play. What's the point?"

"You're right, I did say that and I meant it. But that doesn't change the fact that your ass better be at practice this afternoon."

I didn't answer him because he didn't ask me a question. He expected me to say something, though. He expected me to say I'd be at practice, but I couldn't tell him that. I knew I wasn't going to go, today was a day for Nancy. He didn't know that but I did.

I looked down at my elegantly painted long fingernails, then at my feminine wardrobe. I thought about my mother and her friends. Would any of them let themselves be pushed around like this? I wanted to be a woman - strong and confident like them. After everything we'd been talking about, I couldn't let my coach push me around like some scared teenage boy.

Noting my silence, Coach Holloway screamed at me through the phone. "Peterman! Are you there?"

I drew up my newfound mature feminine confidence and replied. "Don't be an idiot, Holloway. You're talking to me aren't you?"

"What the fuck?" he said in reply, shocked at my defiance. "Make that an hour of wind sprints after practice!"

"Oh, I don't think so, 'coach'. I'm not going to be at practice today or tomorrow or even next week. I've got more important things to do. Is there anything else you want to talk about or are we done?"

The last thing I heard before I hung up on him was, "Fuck you, Peterman. You're through at this school!"

I tossed the phone on the table. In spite of trying to look and feel calm, the fight with my - now former- coach had taken a toll on my nerves. I'd quit the team. That part of Darren's life was over.

Did I really quit, I wondered? I think I did. My heart was racing. I wanted to run to my room and cry. Was I really that upset or did it have something to do with the female hormones I had started taking? I sat down at the table in disbelief. Things wouldn't be the same again. As the real woman watched, I dug inside my purse and pulled out my cigarette case. My hands were shaking as it took me several attempts to light my cigarette.

"Oh my God!" Mrs. Estes exclaimed. "Karen, he's smoking!”

An argument over my smoking broke out among the three women. I could hear them, but I wasn't listening. I was thinking about the phone call with my coach and I was too busy crying over it. Maybe the female hormones were to blame. I didn't want to play football anymore, anyway. I wanted to be Nancy, all day all the time!

"Are you okay, Nancy?" my mother asked, noticing my tears. "Did your coach say something? I'm sorry, honey. Did he kick you off or did you quit?"

I dabbed carefully at my eyes with a tissue from my purse and told her that I'd just quit. I think. "It all happened so fast," I said. "It felt like it was happening to someone else."

Mrs. Estes groaned and shook her head. "See there? Do you see what you did? You just ruined your whole life. How could you even think about giving up football for this?" she asked.

"Because real women don't play football," I said, reverting back to my Nancy voice. It was Nancy's voice, yet it was monotone and without emotion.

"Well that's what you get," Mrs. Estes said angrily. "I hope you're proud of yourself! I can't imagine what your father is going to say when he finds out."

"Bill will understand," my mother said calmly as she rubbed my neck. "It's okay, Nancy. Deep down inside, you know it's for the best. It hurts right now, but it will get better. You'll see."

"What’s with the smoking?" Mrs. Estes asked. "Are you and Bill really letting him smoke? Did you know about this?"

"Of course I knew about it, Susan," my mother said, irritated. "Who do you think gave her permission to start?"

"But he's only sixteen!" Mrs. Estes said.

"Oh please, Sue. How old were you when you started smoking?" Margie Jackson asked. "I was twelve!"

"Times were different back then," Mrs. Estes said. "That was then and this is now and it's against the law for 16-year-old boys to smoke."

"Darren may be 16," my mother said, "But Nancy is 46 and that's all people are going to know and see. She's not going to get in any trouble."

"Why did you start, honey?" Margie asked. "I know it couldn't have been peer pressure because none of your other friends smoke. Do they?"

I told her I started because I thought it would help with the stress I was feeling.

"I can't imagine how hard this must be for you," Margie said. "But please, don't feel embarrassed or ashamed about needing to smoke, especially if it's helping."

I thanked her for being so understanding.

"That's a very pretty cigarette case. Can I see it?" Margie asked.

I slid my case toward her.

"It's a Louis Vuitton," Margie said. "Is it real?"

I wiped away a tear and nodded. "Karen got me the purse and wallet, too, so they all match," I said.

Margie opened the case and looked inside. "Oh my," she said. "Look, Susan. Nancy smokes Virginia Slims just like you, except hers are menthol."

Mrs. Estes grimaced and shook her head and asked, "So what do your big tough football friends think about you wearing your mother's clothes and smoking girly cigarettes?"

I told her they didn't know, and that they wouldn't know.

"Well you can't keep it a secret forever," Mrs. Estes said. "I heard you talking to your coach. You know he's going to tell the guys on your team. Do you think they won't drop by here to see what you're up to?"

My heart did flip-flops because I hadn't thought about my friends coming over.

"Well if they do stop by, I'll just tell them that Nancy is Bill's sister, just in from out of town," my mother said.

Mrs. Estes looked at me drying my eyes. Her stern look softened. "I didn't mean to be so awful to you, Darren, but I just don't understand why you're doing this," she said. "You're such a great kid. I wouldn't have dreamed this would be happening to you in a million years."

"Nancy is still the same person you've always known," my mother said. "But this is the part of her that she's been hiding all her life. It's who she's meant to be. Who she wants to be."

"Explain it to me then," Mrs. Estes said. "Why do you think you'd be happier being like us than being yourself?"

Mrs. Estes had asked me a legitimate question. She wasn't cutting me down or telling me how stupid I was, even though I knew she was thinking it. If I had any chance of winning her over, this was the time to do it.

I told her I didn't think there was any way for me to explain it in a way she'd understand, "It's what I've always wanted and I've wanted it for as long as I can remember," I said earnestly.

"That doesn't sound like a good enough reason to throw away your life," Mrs. Estes said. "I've always wanted to fly, but that doesn't mean I should jump off a tall building. You don't even know for sure if this will make you happy. What if you wake up some day and come to your senses? Don't you think you could have some serious regrets?"

I put my cigarette out and stood up. "Look at me," I said, "Look at my hips and look at my breasts. Look at the fake wrinkles on my face and look at the kind of clothes I'm wearing. This is how I've always imagined myself looking and it's fantastic! But now I've got a chance to do it for real. I won't have to pretend like I'm doing now. If I get the surgeries, I can throw away all the padding and the Hollywood make-up and look this way for real."

"I know you can, honey," Mrs. Estes said. "Modern medicine and science are amazing things. But just because it's possible to do something, it doesn't mean you should. Think about the atom bomb. We could probably blow up any country in the world at the touch of a button. But that doesn't mean we should do it."

I told her I understood what she was saying, but that it was different from what I was trying to tell her.

"Then what are you trying to say?" she asked.

"I'm trying to say that I know I'd be happier as Nancy than I would be as Darren and I want to be Nancy right now instead of waiting to grow up to be her."

"Do you know this for certain?" Mrs. Estes asked. "Or have you just convinced yourself that you'd be happier?"

"I don't know. Maybe it's the same thing," I said as I removed another cigarette from my case and lit it. "Either way, I know I'd be much, much happier as an older woman. It's all I think about."

"And what about thing things that go along with being an older woman, like older husbands and teenage children, and worrying about supporting yourself? Do you think you'd be happier with those things, too?" Mrs. Estes asked. "Or have you even thought about those things?"

I took a drag on my cigarette and exhaled a plume of smoke across the room. "Of course I've thought about them some," I said. "The truth is, I'm not sure if I want those things. I just don't know for sure."

"Maybe you just want to look and act like a woman," Mrs. Estes said. "And you think that playing the part would be enough to make you happy for the rest of your life."

"You're making it sound like it's some kind of game I'm playing," I replied defensively, "Maybe this is fun for me. But if it is some kind of game, I know I'm never going to get tired of it and I want to play it for the rest of my life."

Margie lit another of her long brown cigarettes and leaned forward over the table. "I think I'm just as confused about this as Susan is, but I've known you and your whole family for many years and I don't think you'd do this if you weren't sure about it."

I told her I was absolutely sure about it.

"I'm sure about it, too," my mother said.

Margie nodded and got up from the table. I wondered if she was going to make a toast or a speech, but she walked around the table until she was facing me.

"In that case, I'm very happy for you, Nancy," Margie said as she bent down to hug me.

As I was thanking her and hugging her, I felt four other hands on my shoulders and my back. I looked up to see my mom and Mrs. Estes. They were both crying. We all were crying.

"Can I get anyone some more coffee?" my mother asked, trying to lighten the mood, "I know I could use some."

Everyone - including me - agreed that more coffee would be quite nice.

******

The air in the kitchen softened as it filled with smoke and the sound of a hundred questions. I did my best to answer them all, but at the same time, I had some questions of my own. Mrs. Estes and I were now on a first name basis. She referred to me as Nancy and I called her Susan.

"What's it like to have a vagina?" I asked. Judging by the confused looks on their faces, my question seemed to puzzle them. Shouldn't they, of all people, know, I wondered?

"I don't know how to answer that," my mother said, "because it’s all I've ever known since I was born with one, but I suppose it's nice."

"Are you scared at the idea of getting one?" Margie asked. "I'm sure it's going to be a lot different for you."

"Yeah! No more standing up to use the potty," Susan said, her former sarcasm returning.

"And no more other things," my mother said, "You know… with girls."

"I am kind of scared but I'm really looking forward to it," I said.

"Why? So you can have sex with men the way real women do?" Susan asked.

I blushed and shook my head no. "I haven't thought much about sex, but I do think having a vagina would make me feel more like a real woman, so that's the main reason I want to do it."

"I keep thinking someone is going to pinch me and I'll wake up," Margie said. "I'm so used to you as Darren. Seeing you as Nancy and thinking of you as being my age is just so strange."

I asked her if that meant she didn't like me this way.

"Not at all," Margie said as she slammed her hands on the table. "I think it's wonderful that you're going to become a woman because you’ve convinced me it’s what you always wanted."

"It is," I said, “More than anything.”

"And we do get that this is what you want," Susan said as she touched my arm gently. "I think Margie's trying to say that we're still used to thinking of you as a teenage boy. The last time we saw you, you were talking about football and getting ready for a date with a girl. And now you're sitting at this table looking and acting just like us. You're even smoking like us," she said as she pointed at the cigarette between my fingers.

I blushed and smiled sheepishly.

"It’s such a radical change for us," Margie said. "Does it feel that way to you, too? Or does this feel normal?"

I told Margie that I loved everything about becoming a woman but that it felt far from normal.

"Dr. Giardi doesn't think that Nancy has a female brain," my mother said. "So instead of being a woman living in a boy's body, Nancy is a boy who wants to live in a woman's body."

"I don't know much about transgendered people," Susan said, "But that sounds crazy. Why would your doctor even suggest a sex change surgery if you don't really need it?"

"I do need it, but not in the same way other people do. For me, I need it because I want it so much and since I'm never going to stop wanting it, Dr. Giardi feels like I need it."

"And once Nancy gets the surgery that she wants and needs,” my mother said, “She's going to need a support group to help her deal with all the changes. That's why I asked you both to come over. I thought it would help Nancy to have friends while she's going through this."

Both Nancy and Susan assured my mother and me that they would be my friends.

"Do you really need to go to Mexico to get the surgery? Can't you do it here?" Susan asked.

"She could, but it would take at least two years," my mother said, "And Nancy doesn't want to wait that long. It would also be a lot less expensive if we did it down there."

"So are the doctors down in Mexico going to make her look older too?" Margie asked.

I explained the difference between cosmetic surgery and sex change surgery. "I could have all the cosmetic surgery done here and then go to Mexico for the sex change," I said. "Or I could have it all done down there."

"Except for the orchiectomy," my mother said. "You're going to have that done here. Aren't you?"

I told her I wasn't sure. "There's a part of me that wants to get everything done at the same time," I said.

"But Dr. Giardi said that would be too much stress on your body," my mother said. "She said you should do it in stages. That's why she started you on female hormones."

Margie asked if I was feeling any different from the hormones. I told her about getting emotional and upset. "I think that's why I started crying after my coach called," I said.

"That means you're starting to feel more like a woman," my mother said, "So that's a good thing."

"Won't hormones make your boobs grow naturally?" Susan asked.

I told her they would but they wouldn't make me as big as I wanted to be. "It’s same way with the other parts of my body too," I said. "They'll make my hips and butt bigger but not big enough. That's why I want to get the cosmetic surgery, so I'll look more like you all."

Margie laughed and said, "So you're saying we're old and fat and you want to be old and fat like us. Thanks a lot," she said sarcastically.

I was embarrassed and went on the defensive. "But I'm not saying that," I said. "I think you all are beautiful the way you are and I want to be beautiful like you ."

"It’s okay, honey. I'm just kidding with you," Margie said. "I get that you want to look older. I'm not offended but I am confused. Most women spend their lives trying to look younger than they are and here you sit wanting to look older. It's just a different way of thinking and I'm trying to get used to it."

"I guess it does sound kind of crazy," I said.

"Then why do you want to look older?" Susan asked?

"Older women like you are more real to me," I said. "You know everything about everything because you've already been there and done it. I think that makes you more confident and that's really sexy to me."

"I think sexy is looking like a 20 year old supermodel," Margie said.

"Not to me, it isn't," I said. "If I wasn't going to do this and I was going to stay a boy and grow up to be a man, I'd want to fall in love with and marry an older woman. She'd be pretty and nice like you guys are. And she'd smoke too," I said as I lit another Virginia Slims.

"Is that why you started smoking?" Susan asked as she lit a cigarette of her own.

I blushed and shrugged my shoulders. "I know it sounds stupid," I said, "but I've wanted to be a smoker like you guys all my life."

"You're right," Margie said. "Wanting to be a smoker does sound pretty stupid, especially in this day and age, but you don't have to be a woman to do it. Lots of men smoke."

I told Margie that I didn't want to smoke like a man. "I think it’s gross and gay when boys smoke," I said. "And young girls shouldn't do it either because they don't look old enough."

Susan laughed and said, "But you think it’s okay for the three of us to kill ourselves with cigarettes because we're older and it looks right to you."

"Well, I wouldn't say it quite like that," I said, "But it does look right to me. It’s like it goes with who you are, and fits your style. That's the way I want to be."

"Nancy believes she looks more believable as an older woman when she smokes," my mother said. "She says it gives her confidence and makes her feel powerful and smart and sexy and sophisticated." She smiled at me as Susan and Margie broke into laughter. "Am I missing anything, honey?" she asked.

I felt embarrassed and dumb, and the laughter wasn't helping. "Yeah, that's pretty much it, Karen. Thanks for making me feel stupid," I said.

Margie told me not to be embarrassed. "I think we're laughing because we all probably started for the same reasons you did- to be grown-up and sexy. However, now that we're all big girls, we can't quit because we're addicted. It’s one of those ‘Catch 22’ things."

Susan trimmed her cigarette in the ashtray and said, "Margie is right about it being a ‘Catch 22’, but if you're willing to pay the price, then you might as well enjoy the benefits and pleasures that go along with being a smoker. Just wait until a man lights your cigarette for you! That will really make you feel special and ladylike."

"Tim Moreland lit my cigarette for me when I was at the park," I said with a fond smile, remembering how I felt when I was with Tim at the park.

"And how did that make you feel?" my mother asked.

"It made me feel like I was a real woman, like you guys," I said.

"Well, there you go," Margie said. "It looks like you've joined the middle-aged women smokers club. Congratulations."

Margie's tone was somewhat sarcastic but her sincerity came through loud and clear. "Thank you," I said.

"What about that vagina question you had?" Susan asked. "I know we couldn't answer it for you, but how do you feel about it? How do you feel about trading your penis in for a hole between your legs?"

I thought about my answer for a moment. "I'm definitely scared and freaked out about it, but I think it would be so neat to have a real vagina like you guys have," I said.

"First of all, we're not guys," my mother said. "That's why we have vaginas in the first place. Why do you keep calling us guys?"

"I don't know. Force of habit, I guess. I didn't mean anything bad by it, though."

"Maybe you should call us ladies," Margie said.

"Okay," I said. "I think it would be real neat to have a vagina, like you ladies have."

Susan laughed and said, "I think it would be neat to have a penis. Can you imagine the look on Chad's face if I came to bed with a penis between my legs?"

My mom made an ugly face and shook her head. "I don't think Bill would go for me having one," she said.

Margie leaned forward with a serious look on her face. "Nancy, have you thought about how you'd handle it if you got into a romantic and serious relationship with a man?" she asked. "Would you tell him the truth?"

"Well first of all, he'd be able to tell as soon as he saw her driver's license," Susan said. "I bet it says right on top- under 21, and your real name would be on it too."

"I think we've got that handled," my mother said. "Nancy's doctor gave me the name of an attorney who is going to process her name change."

"She'll still be however old she is," Susan said.

"I would think there are ways around that," Margie said.

"There are, but they're not exactly legal," my mom said.

Susan looked impressed. "It sounds like you've been doing your homework, Karen. But Nancy didn't answer the question. Would you tell a man the truth?" she asked.

"Why should I if I have all the right parts and the driver's license to go with it?" I asked.

"Do you really think that would be fair to the man?" Margie asked.

"I think it would be fair," my mother said, "As long as Nancy is honest about not being able to have kids of her own. Once she gets the surgery, she'll be a real woman. That's all the man needs to know."

"It sounds a bit unethical, but I'm not going to argue with you about it," Susan said. "I think I'd keep it a secret too if it was me. How about you, Nancy? Do you think you're up to using a vagina for the purpose it was intended for?"

"You mean peeing while sitting down?" I asked.

"Very funny!" Susan said. "But be honest with me. Do you think you'll be able to satisfy a man sexually once you become a woman? I know you can do it physically, but I was wondering about the emotional aspect."

All eyes were on me as they waited for my answer. I told her that I'd been wondering and thinking about it too. "I didn't like the idea at first," I said, "But now that I'm getting closer to being a real woman, it doesn't sound as gay as it used to."

"It won't be gay if you get the surgery, honey," my mother said. "You'd be just like any other woman."

"Yeah, but I'd still be me," I said. "It’s not like they're going to give me a brain transplant, so I'd still know what was going on."

"I'm not making light of your dilemma," Susan said. "I just don't think you'd feel as awkward about it you were truly in love with the man. I love Chad and I'd do anything for him. And nothing is disgusting or gross when two people are in love."

"What about everything you were saying about God and how what I'm doing isn't natural or right? Do you still feel that way?" I asked.

Susan laughed and shook her head. "No, honey. I don't feel that way at all. I was just saying those things because your mother wanted me to ruffle your feathers, see how you’d react."

I looked at Mom, raising one of my thin, arched eyebrows. "So does this mean I passed the test?" I asked.

"Yes, and you did it with flying colors," she replied. "So do you still want to schedule that orchiectomy?"

Like Mother Like Son 10

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • older women envy

Permission: 

  • Posted by author(s)

Its a big day for 16 year old Darren Peterman. He has lots of decisions to make. Will he or won't he- get surgery and drop out of school? What will he do when his mother suggests he try being a girl his own age for a while?

Thanks to Victor G for his editing and inspiration. I'd also like to thank Faith for her friendship.

******************
Chapter 10
****************
I woke up Thursday morning with a pair of aching lungs, the result of keeping pace with my mother and her friends by matching them cigarette for cigarette. Some day, I thought, when I'm living as Nancy on a more permanent basis, I won't feel this way. But for now I'll just have to grin and bare it.

The memory of hanging out with my mom and Susan and Margie was still fresh on my mind and I replayed the highlights while I lit my first cigarette of the day. Plain and simple, being one of the girls had been more exciting than I could have ever imagined and it would be something that I would look forward to doing every day for the rest of my life. I got out of bed with no intention of going to school.

I was thrilled that I'd be able to stay at home and dress up as Nancy again, but I also dreaded the looming process of dropping out of school. It was just so overwhelming; I had no idea what was involved with dropping out. For all I knew, I'd have to go before a tribunal or a court. Perhaps that sounds silly but I don't know. I've never been friends with anyone who dropped out of school before, so it wasn't like I knew how to do it.

First things first, however, I told myself as I drew a hot bath and eased myself into the luxurious, perfumed water. Nancy needs to get ready.

I smiled as I carefully drew a pink ladies' razor over my legs and under my arms, shaving them for a smooth, feminine appearance. Even though I was an athlete, my muscular legs were slender enough that they looked great in a sheer pair of hose. I had just the pair in mind for today, a dark smoky gray that would look fantastic with the sweater, skirt, and heels I planned on wearing today.

Oh my God, I thought. I'm mentally picking out women's outfits and shoes to wear, coordinating them in my mind. As Darren, I would never do that, I'd throw on whatever I found in my closet, just like any other teenaged boy. But as Nancy, I loved looking my sophisticated, feminine, stylish best.

I grinned in anticipation. I really am starting to think like a middle-aged woman. I loved it!

After getting out of the bath, freshly shaved and smooth and eagerly awaiting my transformation, I slipped into my foundation garments. There was some discomfort as my gaff tucking away my privates, but I got used to it. It was worth it to have that flat feminine-looking front. A padded girdle and bra with silicone breast forms gave me Nancy's false, mature curves. I made sure everything was in place before I sat before my lighted vanity mirror, eager to begin putting on my wrinkles and makeup. I pulled on a tight-fitting nylon wig cap, tucking away my boyish haircut.

I reached for my Louis Vuitton cigarette case, pulled out a menthol Virginia Slims, and lit up. I took a long, steady drag and held the smoke in for a few moments before exhaling a thick cone of smoke into the air above my head. I was really getting the motions of being an addicted middle-aged female smoker down pat.

I held up my cigarette in a mature, feminine manner. I smiled at my reflection. I cleared my throat and spoke with conviction in my Nancy voice:

"My name is Nancy Peterman, and I absolutely love being a 46-year-old woman."

I winked at my reflection, set my cigarette down in the ashtray, and started to work. First came the latex wrinkles, carefully applied around my eyes and mouth. I loved the way they made me look. So much older, wiser, and oh so feminine.

After my wrinkles set, I began applying my makeup. I thought about all my friends as well as my coaches and teammates as I used a makeup sponge to work a heavy yet flawless layer of foundation over my face. Several guys on my team had called me the night before after practice. Coach Holloway had told them I quit and they all wanted to know what was up.

I stuck to the script of lies my mother had helped me create. I told them that I was sick of school and was ready to make some real money. I told them a made-up story about a fictitious uncle that owned a fishing boat in Alaska. Yes, we had created yet another make-believe sibling for one of my parents; this time it was a fake brother for my mom, given that I - as Nancy - was now my dad's sister, and I didn't want to add any more to my dad's already large family. My friends had all seen the Alaskan fishing show on the Discovery Channel, so most of them swallowed my fibs hook, line, and sinker. They were pissed at me for quitting the team, but they were also envious of the "adventure" they thought I was embarking on.

So much for my friends on the football team. I told the same tale to other friends of mine, ones who didn't play sports with me, but I'd known since I was a little kid. I also told my story to Gina Abramson.

Gina was the closest thing I had to a girlfriend, but we'd hardly talked since I began my adventure into mature womanhood. She thought I was calling to say I'd found someone else and was dumping her. At first she sounded defensive when I called, but her defensiveness turned to sorrow as I unveiled my made-up plans for leaving school to go to Alaska.

I won't sit here and tell you that Gina Abramson was the love of my life, because she wasn't. We'd had some good times together and we'd done a lot sexually. I liked her tons, but not enough to stay male and finish high school.

I did, however, think a lot about what I'd be giving up sexually. Plain and simple, I liked having sex with girls and Gina had been great in that area. Academically speaking, I knew what I was giving up physically by changing genders and ages, but I hadn't really dwelled on the specific emotional consequences. I just knew it was something I didn't want to think about so I chose to push potential remorse to the back of my head.

Any remorse subsided as I recalled how wonderful it felt to be an older woman with my mother and her friends, and how it felt to talk to Tim Moreland as adults and equals. They had all accepted me as an adult woman and that was enough to keep me going ahead with my plans.

I was excited about my new grown-up life but I wondered if I would miss my friends and the life I was leaving behind. The strange part was that I really wasn't going anywhere but as far as my friends were concerned, I was. If ever saw them or ran into them, I'd need to pretend as if I didn't know them, which, of course, "Nancy" would not. In a lot of ways I felt as if I was entering the government's witness protection program.

*****

After over forty-five minutes of painstakingly painting my face and touching and retouching up my makeup and nail polish (I chose a lovely rose color to match my lips, as several discarded cigarette butts in the nearby ashtray could attest), I was finished, completely aged and feminized. I stared at Nancy's lovely, mature face in the mirror. I felt a stirring in my loins, but my gaff held everything in place.

I didn't dwell on it, wanting to see the entire transformation, completely appearing as an older woman. There would be time later to take care of things down there. I looked forward to it. Ever since I'd been given permission to start dressing up as Nancy, to look, move, act, talk, and smoke like a middle-aged woman, my still-adolescent orgasms had been amazing.

Setting aside those thoughts for the time being, I strode over to the closet and pulled out the articles of the outfit I'd planned on wearing today. I pulled on the sheer, dark hose over my smooth, shapely legs. I loved the way the control top of the hose fit into place over my padded hips and bottom. Just like they would on a real older woman, I loved it!

I next pulled on a silky half-slip, followed by a knee-length black pencil skirt. It fit great over my false curves and was just long enough to show off my killer hosed legs. I then carefully pulled on a lovely navy blue turtleneck sweater that was just snug enough to call attention to my ample false breasts.

I finished up the outfit with the remaining pieces of my disguise: black leather women's belt; gold clip-on earrings; a slim gold ladies' watch on my right wrist; a wide gold bracelet on the left; my green-tinted contact lenses; my long, femininely-styled blonde wig secured into place atop my wig cap. Lastly, I slipped my feet into an exquisite pair of black leather pumps with slender 3-inch heels. The height of the heels made me slightly taller than average for a woman, about 5-foot-9, but nothing out of the ordinary. I checked my appearance in the mirror.

Satisfied that I was once again completely passable as an adult woman, I spritzed myself with some Chanel perfume, tossed my cigarette case and lighter into my handbag, slung the bag over my shoulder, and walked confidently toward the kitchen, eager to meet another day as my adult female alter ego.

I found my mom in the kitchen talking on the phone. I poured myself a cup of coffee and sat down at the table next to her, crossed my legs in a feminine manner, and lit a cigarette. I noticed that she didn't even blink at either my appearance or so casually smoking in her presence. I smiled inwardly that she really was so accepting of my Nancy persona.

Mom got up and hung up the phone. "Who was that?" I asked. I thought perhaps she was talking to either Susan or Margie because of the things she was saying about yesterday.

"That was Dr. Giardi," she replied. 'I was telling her about your meeting with Susan and Margie. She was really impressed by the way you handled yourself."

"Did you ask her about me getting the orchiectomy?" I asked.

Mom's smiled as she lit a cigarette. "As a matter of fact I did," she said with an exhale.

"So….Is she okay with me getting one?" I asked.

Mom nodded playfully. "Oh yes," she said. "That and much more. You're not going to believe this, but Dr. Giardi has been making arrangements with a reputable surgeon down in Mexico."

"Mexico? I thought Dr. Lipscomb was going to do it here."

Mom closed her eyes and squealed. "What would you think if I told you we could go to Mexico next week and you could have an orchiectomy and the cosmetic surgery you need?"

"You mean boobs?" I asked excitedly.

"It's better than just boobs," my mother said. "While we were talking to Susan and Margie yesterday, Dr. Girardi was discussing your case with a surgeon who can do everything!"

"Everything at the same time?" I asked hesitantly.

"Not at the same time, but close," my mother said. "Our first day would be a consult. The surgeon will talk to you about how you want your body to look. Dr. Giardi said he'll show you pictures and you can decide how big your breasts and hips should be. He'll also talk to you about cheek and chin implants, but here's the really wild part. None of the implants you'll be getting will be made from plastic. You're going to get a fat transplant!"

"Fat transplant?" I asked. "You mean they're going take fat from someone else and put it in me?"

"Exactly! Its just like getting a blood transfusion except its fat."

"Is it safe?" I asked.

"Of course it is," my mother said. "Dr. Giardi wouldn't suggest it unless she was sure. But the best part is that it will stay with you forever! Dr. Giardi says that plastic implants can show once your body starts to age or lose weight, but its not like that with fat."

"What about my skin? Can he make my skin look older?" I asked.

"Absolutely! Dr. Giardi talked to the surgeon about it and it turns out that its easier than she thought it would be. They can destroy you collagen with ultra-violet lasers. It's going to be painful though. Dr. Giardi said you'll probably have red skin and blisters for about a week after the procedure, but afterwards your skin will look as old as mine. Your breasts will sag and you'll even have crow's feet around your eyes and lines around your mouth. Isn't that amazing?"

"That is amazing!" I said excitedly. "And it can happen just like that?"

"Just like that," my mother said assuringly. "Its complicated but its simple and by simple, I mean that its been done before. It turns out you're not the only person who wants to look older than they really are."

"Are we going to have to stay down there for a whole month?" I asked.

"Oh no! Nothing like that. We'll stay a week. Dr. Girardi said they could do your orchiectomy and the cosmetic surgery on the same day. You'll need to stay three days in the hospital and two more days in a hotel. They'll take the bandages off after that and we can catch a flight home. And then we'll go back after Christmas to get your vagina! Can you believe it, Honey? You're going to be a real older woman in January!"

I did my best to tell my mother how happy and excited I was without letting on that I was freaking out. I reached under the table and squeezed my balls. Oh my God! Next week they'll be gone!

"Are we going to keep having to back down to Mexico for checkups or anything?" I asked.

"I don't think so. Dr. Girardi said that Dr. Lipscomb can handle your aftercare," my mother said.

I pulled a fresh cigarette from my case and lit it using the one in my hand, then crushed the old, spent one in the ashtray. I'd done it without thinking much about it, but it did catch my mother's attention. "Not that I'm keeping count but it's hard not to notice how much you've been smoking lately," she said. "How's your carton holding out?"

"I've got one more pack after this," I said nervously.

Mom laughed at my perceived plight. "Relax, Honey! I'm not mad at you," she said. "I was just going to say you need to keep up with how many cigarettes you have left. I'd rather you didn't smoke at all, but since you do, I don't want to see you run out because I know how bad that feels. We'll stop by the store later this morning and buy you another carton. On second thought, we should probably get you two. Maybe you should start smoking the 120s. They're a little longer, so maybe you wouldn't smoke as many."

"You mean like those long skinny brown cigarettes that Margie smokes?" I asked.

"Yes," my mother said. "Those or Virginia Slims 120s. The Virginia Slims are white."

"I like the way the brown ones look," I said. "They look so elegant and sophisticated. You know…kind of older and more mature. But they're so much longer than my Virginia Slims and they just barely fit in my Louis Vouitton case."

Mom shook her head and laughed. "My oh my," she said. "You're worried about your cigarettes fitting inside your pretty little cigarette case. You really are a woman."

I blushed and told her I was sorry. "I guess that does sound kind of silly."

Mom covered my hand with hers and assured me that I wasn't being silly. "It's a part of who you are and who you want to be and I'm behind you 100%."

"Thanks Mom. I know its hard to understand," I said.

"It is hard to understand," my mother said, "but I was a little girl once too and I remember the way I felt."

"But its not the same thing," I said. "I don't want to be a little girl. I want…"

My mother finished the sentence for me, "You want to be a real woman and you want to smoke like one too."

"Exactly," I said. "That's exactly what I want and its what I've always wanted ever since I can remember."

"You know honey, if you want to try a More 120, we could buy you a pack and if you like them, we could buy you a long cigarette case like Margie's."

I remembered the way the skinny brown cigarette looked in Margie's hand. A cigarette like that wouldn't look right with a younger woman, but they suited Margie to a tee. I looked down at my hand and wondered if I would look as sophisticated and proper as Margie did if I started smoking More 120s. I also thought about how cool it would be to buy them myself. I knew I looked older but I wanted to prove it and buying cigarettes was a good way to see for myself. "Do you think I could go in the store and try to buy them myself?" I asked. "I think that would be so awesome!"

"Well, I wouldn't call it awesome but I can see how you would," Mom said solemnly. She paused as if she was trying to remember something.

"Were you going to say something else?" I asked.

She shook her head and shrugged her shoulders. "I don't know. I was just thinking about when you were a little boy."

I exhaled and told her that I hadn't been a little boy for a long time, and sure as hell didn't look like one now.

"I know you feel that way, but for me it was just yesterday. We're supposed to be best friends, and we are, but you're still my baby boy and you'll always be my baby boy, even after you become a middle-aged woman."

"I can see you're really bothered about this, but why did you wait until now?" I asked. "I thought you wanted me to be a woman."

"It doesn't matter what I want, sweetie. This is your life."

"Then why does it sound like you're backing out? Is that what you're doing?" I asked, a note of fear in my voice. She was supposed to help me become Nancy, she couldn't undo everything now!

Mom noticed my apprehension and patted my hand gently.

"I'm not backing out, honey. It's just that this is happening faster than I thought it would. I thought I'd have more time to get used to the idea. Don't you see? I love you so much and I don't want to see you make the worst mistake of your life."

I told her that wanting to be an older woman wasn't a mistake. "It's what I want, Mom. I promise."

Mom bit her lip and shook her head. "What would you think about some kind of a compromise?" she asked.

"Compromise? What kind of compromise? I hope you're not talking about splitting it down the middle between 16 and 46 because I don't want to be 30."

"Actually, I was thinking younger than that. I was thinking maybe you could try out being a girl your age."

I stabbed out my cigarette in the ashtray and shook my head violently. "I don't want to be a teenager, Mom. I don't want to be a teenage boy and I don't want to be a teenage girl. I want to be a grown woman like you."

"How about just for a day? We could do it tomorrow and then you could go back to being older for your date with Tim."

"What would that prove?" I asked. "I've never wanted to be a teenage girl and dressing up like one isn't going to change my mind."

"Okay then. If you won't do it for yourself then do it for me."

"For you?"

Mom sighed and shook her head. "I'm 46 years old and I'm never going to have a daughter."

"So you're saying this about you and not about me?" I asked.

"Kind of yes. I suppose it is," she said. "But it wouldn't hurt you to try it out and I would really appreciate it."

"Okay, so we're talking about being your daughter for a day? Just a day?"

Mom nodded slowly.

"And then I could go back to being older and we can go to Mexico next week?"

"Yes. If that's what you want. We can still go to the bank today and get our passports."

"So what would we do if I spent the day as your daughter?"

"You know. Mother and daughter things. I thought we go shopping and do lunch. I've always dreamed of doing that," she said. "I hear the way my other friends talk about spending the day with their daughters and I get so jealous. And if you're up to it…I thought you might try on my wedding dress."

"Your wedding dress?" I asked.

"Yes. I've always wanted to have a daughter and see her wear it. I think you'd look so beautiful in it."

I had to admit that I was psyched about trying on my mother's wedding dress. I knew exactly where she stored it in her closet, but it was vacuum packed so I left it alone. But still, I didn't want to risk showing my excitement because I didn't want her getting the wrong idea.

"I guess that would be fun but its not like I couldn't do it later," I said.

Mom shook her head and said, "Sweetheart, when you get back from Mexico, you're body is going to look like its given birth to triplets. Maybe I didn't tell you but that cosmetic surgery is going to add 20 pounds. You'll never be able to fit into my wedding dress unless you do it now."

"And this would make you happy?" I asked strategically.

"Absolutely! You'd make me the happiest mother in the world if you did this for me."

"Then its a deal."

"Okay then! We'll do it tomorrow," she said as got out of her chair and came around the table to hug me. "And who knows? Maybe you'll like it so much that you'll stay in school and become a cheerleader."

"Speaking of school, I thought we were going to take me out," I said.

Mom gripped my shoulder and said, "I suppose we should, but if you change your mind about starting out as a younger woman and growing into an older woman, we could enroll you in another high school."

"Well let me drop out of this school first and we'll see what happens later," I said.

Mom and I talked about my plans for dropping out of school. The thought of dropping out was liberating for obvious reasons. It would free me up to pursue my life as Nancy. On the other hand, I had to admit that it made me feel like a failure. I had never been the best student but I had never imagined my self dropping out of school. I also never imagined it would be so easy to drop out.

I watched and listened as Mom placed a call to my guidance counselor. The call lasted less than two minutes.

"Congratulations," my mother said. "After today, you'll never have to wear boy's clothes again. Your counselor said that I need to bring you in and sign some papers and that will be that."

That wasn't what I wanted to hear. "What? I have to go back to school?" I asked.

"You do if you want to drop out and live your life as a grown-up."

"But what if I see my friends or Coach Holloway?"

"I suppose you could run and hide but wouldn't you like to make one last stand as a boy?" she asked.

"What do you mean- one last stand?" I asked.

"Well, unless something really crazy happens, like the sky falling on top of this, today is probably the last day of Darren Peterman's life. Just think about that for a second."

I took my mother's suggestion and thought about today being the last day of my life as Darren Peterman. It was strange because it made all the sense in the world but I'd never really thought about in terms of finality.

I'd been so busy running away from Darren while running toward Nancy that I'd never really taken the time to think about what I was leaving behind.

"I hear what you're saying," I said, "but it doesn't really change anything because I don't want to be Darren any more."

"I know you don't, Honey. However, like it or not, Darren and Nancy are always going to be one in the same. You can't be Nancy without being Darren and you can't be Darren without being Nancy. I've heard you say things like that yourself."

"Okay. So what are you really saying?" I asked.

"I'm saying that Darren needs to leave Nancy a legacy. You were never a failure as a boy! Don't go out with a whimper now. I think it would be a big mistake and an injustice to yourself if you spent your last day as a boy with your head held low. Stand up for yourself like you did with your coach yesterday. This will probably be the last day that anyone from your school ever sees you again as Darren. Give them something to remember you by."

"But how am I supposed to do that?" I asked.

"By being proud of yourself! How else?" my mother said. "I want you to walk into that school with your head held high. You quit the football team and you're dropping school!"

"But I'm not proud of that. I'm just doing it because its the best thing for me to do."

"I'm not going to disagree with you about that," my mother said. "However, that doesn't mean you can't make the best of it. It's your last day, Sweetie. Have some fun with it. Walk with a swagger. Be an ass."

"An ass, as in asshole?" I asked. "Why would you want me to act like an asshole?"

"Because once you become a woman, you'll never have the opportunity to be an ass the way a man can be an ass," my mother said while trying to keep a straight face.

And that's when it hit me. Today really was going to be my last day as Darren. A montage of thoughts flashed across my eyes and made me smile. "I can't get in any trouble today. Can I?"

Mom raised an eyebrow and asked, "What are they going to do? Kick you out of school?"

*******

I met my mother in the kitchen after getting dressed. Except for my pretty eyebrows, I looked like my old myself, and it made me feel naked and vulnerable. I was wearing jeans and a button down oxford shirt with a pocket on the front.

Mom smiled at me and lit a cigarette. "You make a beautiful older woman but you're not so bad as a boy either," she said.

"I feel stupid," I said. "What if someone gives me a hard time about my eyebrows? You know they will."

"Fuck them!" my mother said defiantly. "Who cares what they think? Tell them you like the them that way."

My mother and profanity weren't cozy bedmates so I was a bit surprised by her language. "Fuck them?" I asked.

"Well…not literally. I was just trying to sound tough because I want you to be tough."

I nodded and told her I'd keep that in that mind. I reached for my cigarette case but withdrew my hand. I needed a cigarette badly but I couldn't bring myself to smoke in boy mode, especially not Virginia Slims.

Mom noticed my reaction and said, "I guess you wouldn't feel too tough smoking Virginia Slims, would you?"

"Not exactly," I said solemnly.

"Would you like one of mine?" she asked as she offered me her cigarette case. "They're Marlboro so men smoke them too."

"But I'm not a man, Mom. I'm just a boy and boys shouldn't smoke."

"No, Honey. Today you're a man so today you'll smoke like a man," she said as she retrieved a full pack of Marlboro Light 100s from her carton in the cupboard. I tried to argue with her as she tore off the cellophane and tucked them into my shirt pocket but she wouldn't take no for an answer.

The cigarettes felt heavy and dirty and foreign against my chest. The top of pack was clearly visible as it poked out of my pocket. The pack screamed Marlboro and like my eyebrows, there was no denying that they were there. I felt ashamed.

"Well aren't you going to have one?" my mother asked.

I nodded sadly as I removed the pack from my shirt pocket and lit one. I inhaled a big puff of shame and humiliation and blew it back out.

"Feel better yet?" my mother asked.

"I feel better in some ways," I said, "but not in others."

"Well remember; whatever doesn't kill you will make you stronger," my mother said.

I chewed on those words as we drove over to my school.

*****

We arrived at my school around shortly before 11:00 while classes were changing. I was never a wallflower and people knew me so I didn't go unrecognized. Everyone had heard the news or the rumors. I'd quit the football team and I was dropping out of school to go fishing in Alaska.

People said hi to me in the hall. I saw their eyes drawn to the pack of cigarettes in my shirt pocket. It bothered me a lot but I was also very thankful for them. I quickly figured out if people were looking at my cigarettes then they wouldn't notice my eyebrows as much.

I thought I might make it to the counselors office without seeing anyone from my football team when I turned the corner and almost walked into Coach Holloway and John Adams, our offensive tackle.

John and I were friends and he was clearly glad to see me despite what he might have heard. "Peterman! You're back!" he said as he punched my shoulder.

Holloway glared and the veins on his temples pulsated as his jaw tightened. "You're too late, Peterman. I kicked you off the team when you didn't show at practice yesterday."

I'd like to say that I had matured enough from our phone conversation to not be intimidated but that wasn't the case. I could have said okay, and kept walking, but I remembered what my mom had said about going out with a bang.

What does "going out with a bang" mean, anyway? Did she expect me to pull the fire alarm or start a food fight in the cafeteria? I looked at my mom for a little help and reassurance but things were moving too fast.

Coach Holloway reached out and pulled the pack of cigarettes from my shirt pocket. "You and I are going to take a little trip to the principal's office, buster," he said as he grabbed me by the elbow and began leading me up the hall. "You're looking at five days suspension for bring cigarettes on school property," he said menacingly.

The kids in the hall parted for us and stared as the coach dragged me behind him as he screamed and yelled about the cigarettes and my smoking. I looked over my shoulder at my mother who was following us. I could tell she was mad and angry but I also knew that this was my fight and not hers. She wasn't offering to step in and I wasn't ready to ask her too.

Coach Holloway pushed me into the administrative offices and loudly announced that he had caught me with cigarettes and needed to see Principal Davis.

Mrs. Colcheck looked up from doing her nails and sneered at me as she shook her head. She shot me a look that said I was a dumb shit delinquent. Oddly enough I'd alway had a case of the hots for Mrs. Colcheck. She was an attractive redhead in her early 40s and I'd seen the cigarettes she carried in her purse. She'd always been so nice to me when I was playing by the rules and staying in my place, but now that I wasn't, she couldn't even offer me a sympathetic look.

"Mr. Davis is in his office," Mrs. Colcheck said. "You can take him back there."

As Coach Holloway was pushing me down the hall, I heard Mrs. Colcheck ask my mother if she could help her.

"He's my son. Can I go back with him?" she asked.

"Mr. Davis always call the parents after something like this happens and he's had a chance to talk to the students. If you can just take a seat, I'll let him know you're waiting."

Coach Holloway pushed me into Mr. Davis's office and dropped my pack of Marlboro Lights on to the desk as Mr. Davis scowled at me from his chair. Coach Holloway loudly explained my offense and did his best to make it sound as if I'd murdered something. If I had murdered anything, it was Coach Holloway's ego.

Mr. Davis told me how disappointed he was in me and recited an excerpt from a lecture that I'd heard in health class. He also went on to tell me that it was customary to suspend students who had been caught with tobacco for 5 days.

"I know you have a big game tonight, Coach," Mr. Davis said.

"One of the biggest," Coach Holloway agreed.

"We have to punish Darren, but if you want to, I suppose we could let you discipline him. It would save you a player and I suspect your punishment would be more difficult than five days of sitting around home."

Judging by the look on Coach Holloway's face, it had never occurred to him that he might be able to have his cake and spit on it too. "I think we could work something out," he said. "We can dress him out out for tonight's game and then I own him for the next 30 days."

"Thirty days sounds harsh," Mr. Davis said. "However, it will look better on your record than a suspension. Of course I'll only agree to this if Mr. Peterman signs a pledge to give up smoking immediately." He looked up at me and said, "Not that it matters, but I assume you're agreeable to the plea bargain, Mr. Peterman."

I wasn't a natural born smart-ass, but I hadn't come back to return to school or to play football for Coach Holloway. I couldn't say yes so I had to say no, but I knew this was what my mother was talking about when she said I should go out with a bang.

I looked down at the name plate on the desk as I chose my words. "To tell you the truth, Arnold, I think I'm going to be busy doing something else for the next 30 days," I said as I picked up my cigarettes and tucked them into my shirt pocket. "Now if you'll be so kind as to excuse me, I have an appointment with my guidance counselor and it would be rude to keep him waiting. Don't you think?"

I turned around to walk out the door but not before I saw the two shocked faces with hanging jaws staring after me.

I saw my mom standing in the doorway and I expected Mr. Davis to call after me, but instead I felt Coach Holloway's hand yanking on the back of my collar. He spun me around so that I was facing his red angry face. He was screaming and yelling. I heard my name. I heard the word "pussy" and I heard the word bastard.

I couldn't breath because he had twisted my collar around my neck. I wondered if he was really going to kill me before I passed out. The man had definitely lost control and if I didn't do something soon, I was going to wind up seriously hurt and injured.

I tried to fight back and get away, but the harder I fought the more he choked me. I did the only thing I could think of. I kicked him in the balls.

When he lowered his hands from my neck to cover his balls, I round housed him in the face for all I was worth. Coach Holloway fell backward against the filing cabinet, knocking a painting loose from the wall.

I dropped to my knees and rubbed my neck while I caught my breath. I looked up to see my mother rushing into the office. She was panicked and hysterical, but when I told her I was okay, she turned her fury on Coach Holloway who was still reeling in pain. She swung her purse like a mallet against the side of his head and he fell like a tree in a storm.

My mother read the riot act to both my former principal and coach. She threatened to call the police and file a lawsuit against the school. Mr. Davis immediately grasped the seriousness of the situation and began apologizing profusely. He offered to overlook my tobacco infraction.

Mom walked up to his desk and told him he could shove his tobacco infraction up his ass. "The only reason we came up here today was to withdraw Darren from this hell hole that you call a school."

Mr. Davis escorted my mother down the hall to Mr. Edwards' office and assured us that he'd assist us in anyway he could. "We'll have his transcripts delivered to any school of your choosing," he said.

My mother told him that wouldn't be necessary but if he really wanted to do something to appease her, he'd fire Coach Holloway before she got home to call her lawyer.

Mr. Davis handed Mr. Edwards the discipline form he had begun filling out and told him to file it but not report it on my permanent record. He then urged Mr. Edwards to do anything we asked before shutting the door behind him and slinking back to his office.

Although he'd been my guidance counselor for the last 3 years, this was only the fourth time that I'd sat in his office. I'd always been a good kid making decent grades. Up until now, I hadn't had a reason to see him other than the mandated once-a-year meetings.

He seemed like a nice enough guy, a family man judging by the pictures on his desk and walls. He was older, probably in his late 40s or early 50s. Like most older guys, he was a little on the heavy side. His remaining hair was dark and salted with gray. He also sported a beard and wore glasses. If there was anything special about him it would probably be his blue eyes and mellow voice. He had nice friendly eyes that seemed to care.

"That was quite a commotion down the hall," he said as he sat back down. "And from the sound of things it looks as if you got the best of Mr. Davis."

My mother told him that Coach Holloway had tried to strangle me. He listened intently as my mother and I filled him in on what had happened in the principal's office. After we finished telling him the story, Mr. Edwards said that he hoped Mr. Davis would take my mother's advice and fire Coach Holloway. "The man is a loose canon," he said.

Mr. Edwards looked at me and then to my mom and said, "So am I to take it that you're here to follow up on our phone conversation?" he asked.

"Yes we are. Darren wants to withdraw from school and I believe you said we'd need to sign some papers."

Mr. Edwards opened one of his desk drawer and took out some forms. "The process is simple enough," he said. "Both of you will need to sign on the dotted line and that will put an end to Darren's high school education. However, before I can let you do that, I need to talk with Darren about the decision he's making and the factors that led up to it. In other words, I'm going to try to change his mind."

That's when my mother did something that surprised me. She took Mr. Edward's side. Of course I realized she was just playing along and I completely understood her motivations. My mother had a reputation to uphold. I'd almost been suspended for bringing cigarettes to school and I was dropping out of school. I suppose there was no reason for both of us to have to look bad.

His soft blue eyes focused on the pack of cigarettes peeking out from my shirt pocket. "I take it that Mr. Davis and Coach Holloway wanted to suspend you for bringing cigarettes to school. Obviously suspension isn't on the table any more, but I'm still curious. Why did you start smoking? You don't seem the type."

I gave him a shrug and told him I didn't know.

Mr. Edwards nodded his head and told me had started for the same reason when he was my age.

"Really? You smoke?" I asked.

"Unfortunately, yes. I do smoke, which is why it pains me so much to see young people such as your self take up the habit." He turned his attention to my mother and asked how she felt about me smoking.

"I don't like it all," my mother said. "His father doesn't smoke, but I do and we've always told him and his little brother never to start. He's just been so rebellious all of a sudden."

"I see. How are things at home? Is everything okay with you and your husband?"

"Things are great," my mother said. "It's just Darren. I know it's not drugs or anything. He's just got this crazy idea in his head that he's tired of being a kid and wants to grow up and go out on his own."

Mom told him about her fictitious brother who lives in Alaska and owns a fishing boat. "Darren is going to live with my brother and work on his boat. I wish he'd stay in school and go to college, but I know my brother will watch out for him. The money should be good too."

Mr. Edwards turned to me and said, "I have kids of my own and one of them is about your age. He's in a hurry to grow up too and I don't understand that. Being a grown-up isn't all its cracked up to being. People still tell you what to do. Mr. Davis tells me what to do and how to do it every day."

"At least you're getting paid and you're making money," I said.

"That's true," Mr. Edwards said. "And because I stayed in school and went on to college, I get paid well for being told what to do. I know this fishing thing sounds like a lot of money to you right now and it probably is. But what about 10 years from now? You're going to want to get married some day and raise a family. You won't be able to do that if you're making the minimum wage."

I politely told him that I'd already given it a lot of thought and I wasn't going to change my mind. Mr. Edwards wouldn't take "no" for an answer. He wasn't overbearing, but he asked questions that made me think and he dissected my answers.

Mr. Edwards was very persuasive. I think he would have talked me into staying in school if I'd been telling the truth about wanting to work on a boat. He painted a rosy future for me if I stayed in school. He made it sound as if I would have fame, fortune, fast cars and a pretty wife. Those things would have sounded good a couple weeks ago but not any more.

Without question, I admired his perseverance and character. He had put his heart and soul behind selling me on the concept of staying in school, but for what reason? I seriously doubted that he earned a bonus or a commission for every student who stayed in school. His motivations were completely unselfish and I liked that about him.

I looked at one of the pictures of him and his family that was sitting on the desk. I assumed it was taken some years earlier because Mr. Edwards had more hair and less gray. They looked like a happy family. He and his wife had two boys and one girl. I thought his wife was very pretty and I found myself wondering if perhaps he had a fast car in his garage. Fame, fortune, fast cars and a pretty wife. I was happy for him.

I picked up a pen off his desk and told him I was ready to sign the paper. He looked at my mom one last time before sliding me the paper and pointing to the line where I was to sign.

As my pen scrawled across the paper, I imagined myself signing an official document as Nancy Peterman. Dropping out of school took me one step closer to that goal. I handed the pen to my mother and had her sign below my name.

We stood and thanked Mr. Edwards and he wished me luck. "Be safe on that boat," he said, "and try to give up smoking if you can."

*****

I couldn't resist stopping by Mrs. Colcheck's desk as we were leaving for one final goodbye. She swallowed her sneer as I approached her. I looked at the nails she had been working on when Coach Holloway had dragged me into the office. She had painted them pink and I told her they would have looked better if she had used red, "And you might want to go a little easier on your make-up the next time. Too much makes you look like a drag queen. Don't you think?" I asked.

She looked at me as if I'd hit her with a brick.

"Nice job back there," my mother said as we walked out of the office and into the crowded hall. "Do you have any more loose ends or unfinished business to take care of?"

I took a deep breath and sighed as I watched the students walking by on their way to class. I told her I didn't think so. "The only thing I want to do now is to have a cigarette and get out of these clothes."

Like Mother Like Son 11

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School
  • Child
  • Mature / Thirty+

TG Themes: 

  • Age Regression
  • Age Progression

Other Keywords: 

  • Mothers
  • older women envy

Permission: 

  • Posted by author(s)

Mom wants a daughter! Or does she? Darren's mother takes him shopping for a younger look. Darren experiences an epiphany.

**************
Chapter 11
**************

As we were pulling out of the school parking lot, Mom said that we she wanted to take me shopping for a younger look. I reminded her that I wasn't dressed to go shopping for girl's clothes.

"That's okay," Mom said. "We'll go to Pine Valley Mall. That's far enough away that no one will know you, besides we're not really going for clothes. We just need a wig or two."

"But don't I need the right kind of clothes?" I asked.

"I was thinking we could go to a thrift store," my mother said. "Besides, its not like you'll wear them again after tomorrow."

"I'm still going to be a boy shopping for girl's clothes in a thrift store," I said.

"And if you didn't look like a boy, you'd look like an older lady. An older woman shopping for teenage girl's clothes looks just as silly as a teenage boy doing it. Don't you think?"

I thought my mother's rationalization was silly at best but I didn't argue with her. I had agreed to be my mother's daughter in exchange for wearing her wedding dress and I was going to do it even if I died from embarrassment and humiliation.

"Did I tell you I talked to your father while you were getting dressed?" Mom asked.

"No."

"Your father had some suggestions on what we should buy today," she said.

I bet he does, I thought as I put on my poker face. "Like what?" I asked.

"Just some things but I don't want to talk about it right now. We'll figure it out when we get to the mall."

I recognized her tone of voice and heeded the warning. Whatever it was my father had said was bothering her. "Okay," I said as I pulled the pack of Marlboro Light 100s from my shirt pocket and lit one as I looked out the window and thought about everything that had happened at school.

For the first time in my life, I'd been a bad boy of sorts. I'd brought cigarettes to school. I'd talked back to authority figures. I had even kicked Coach Holloway in the balls. I had dropped out of school like the juvenile delinquent that I wasn't. I had permanently changed everyone's perception of me. I had destroyed my reputation.

I had run a dagger through Darren Peterman's heart so that Nancy Peterman could live, but at the moment, I was neither. I was some kind of androgenous freak on his way to the mall to become the teenage daughter of my mother's dreams.

Darren Peterman was dead. How could I feel embarrassed for a dead boy? Everyone at Pine Valley Mall was going to think I was my mother's sissy son. So what? It doesn't matter any more. Darren Peterman is dead. Long live Nancy Peterman. But who would I be after we were done at the mall?

*****

"You're very quiet," my mother said as she merged into highway traffic. "What are you thinking about?"

"A lot of things," I said. "But right now I was just wondering what you're going to call me after I get dressed up like a girl. It wouldn't be right if you called me Nancy."

Mom smiled and said, "Your father and I were going to call you Megan if you'd been born a girl."

"Okay then. Megan, it is."

"You did a great job standing up for yourself back at the school," my mother said. "I'm very proud of the way you handled yourself."

"It didn't have to be that way. We made it harder than it had to be. Why did we do that?" I asked.

"I'm not exactly sure," my mother said. "I thought I had some kind of a master plan before we did it, but now I don't know any more."

I told her that I looked like an asshole back there. "Everybody hates me now."

"Maybe they hate you because you stood up for your self," my mother suggested. "From what I saw, you didn't have much of a choice with Coach Holloway. He attacked you. He was choking you."

"I know I had to do something," I said. "But it just feels like we did it on purpose, like we set a trap."

"I meant it to be a good experience for you," my mother said.

"You think acting like a juvenile delinquent is a good experience. How so?" I asked.

"I just thought it would be good for you to experience the younger side of life before you become Nancy for good and forever. I feel the same way about you experiencing what its like to be Megan."

"You want me to be Megan because you want to experience what its like to have a daughter," I said.

"Maybe I do but I don't want to talk about Megan right now. The important thing is that your father I think you should experience female life from the younger side. Think about it. How can you pass as an older woman unless you've had the experience of being a younger woman?"

I told her I didn't know but I thought I'd been doing a pretty good job of it.

"You are. But now you'll be able to do an even better job, because you'll have some real experiences to draw from," she said.

"I wouldn't call them real experiences. All I'm going to do is get dressed up and look like a teenage girl. Its not like I'm going to experience anything for real."

Mom sighed and shook her head. "So what you're saying is that you're just doing this so you can try on my wedding dress."

I nodded and said, "I don't want to be a teenage girl. I want to be a real woman like you and Margie and Susan. I don't want to be thin and giggly. I want to have some meat on my bones and some wrinkles on my skin, and I want people to take me seriously as a woman and respect me."

"But you'd still do it for me?" she asked.

"Of course I will. I told you I would so I will. But…do you think we could stop by a convenience store first."

"I see a Shell station on the right," my mother said. "What do you need?"

"Cigarettes," I said, as I looked at the smoldering Marlboro Light between my fingers. "No offense, but I really miss my Virginia Slims Menthols."

"I thought you said you wanted to try some of those More 120's. You know, the kind Margie smokes."

"I don't know. I don't think so," I said. "I really love the way Virginia Slims taste and like the way they look too. They make me feel sexy and pretty but no-nonsense and kind of conservative at the same time."

Mom laughed and said, "Image is everything."

"Well you know what I mean. Don't you?" I asked.

"As a matter of fact I know exactly what you mean and for what its worth, I agree with you. The Virginia Slims are probably a little more age-appropriate for you. You'd have to grow into the brown Mores."

"Yeah. Maybe I'll try them when I'm older," I said.

"And just when do you think you'll be older than 46?" she asked.

I asked her what she meant by that.

"Well, I'm just thinking that after next week, you'll look a 46 year old woman without make-up. Seeing as how you're not even 17, you could look the same way for the next 30 years. Have you thought about that?"

"As a matter of fact, I have and I don't like it too much. I don't want to be 46 forever. I want to get older like a real woman does. When you're 80, I want to look like I'm 80 too."

"Believe it or not, I think that's a good idea," my mother said. "But you have to realize, there needs to be a stopping point. I'll be 80 in 35 years and you'll only be around 50 or 51. Even with the smoking, you'll still have a lot of life left to live after I'm gone. And I don't think you'll want to live and act like a 110 year old woman."

"No, I guess you're right. But I still think it would be neat to grow old with you and Dad."

Mom nodded thoughtfully as she pulled into a convenience store. "First things first," she said. "I believe you told me that you need some girly menthol cigarettes. By the way, I hope you don't expect me to carry your cigarettes for you in my purse."

I knew right away what my mother was suggesting and I wasn't going to go for it. "I can't walk around with a pack of Virginia Slims poking out of my shirt. I'd look like a fag."

Mom groaned and told me not to use that "word". "It sounds hostile and angry," she said.

"Well that's what people are going to think," I argued.

"So what if they do? Let them. Besides, it not as if you don't have a feminine side to you. Why not flaunt it? At least for today."

I closed my eyes and sighed. "Is this one of your things about going out with a bang?" I asked.

"Kind of," she said. "Its just that as much as I want to support you, well, I don't want to make it completely easy on you."

"So you're saying you want me to feel humiliated and embarrassed?"

"I suppose you could think of it like that, but I prefer to think about it as character building. Remember what I said about things that don't kill us make us stronger?" she asked.

"Okay. So you think I'll be a better person if you make me into a flaming sissy today. Is that what you're saying?"

"Those are your words, not mine," my mother said. "But the sentiment is correct. For better or worse, your heart is set on living your life as a middle aged woman. Do you honestly think you can do that without experiencing some of what life has to offer? And I'm talking about downside as well as the upside. Don't you see sweetheart? I'd be doing you a disservice if I made this easy for you."

Mom put the car in park and opened her door. "Well don't just sit there. You're going in the store with me."

"What?"

"You heard me. If you're going to smoke then you need to own up to being a smoker. Besides, didn't you tell me it would be awesome if you could buy your own cigarettes?"

"But I was talking about looking like Nancy when I did that. They won't sell me cigarettes! I'm just a kid."

"That's okay," my mom said, "because they won't be selling you cigarettes. They'll be selling them to me. However, I think its important for them to know that I'm buying them for my son."

I felt defeated as I followed my mother into the store. The clerk was a burly guy in his late 30s. There were also six or seven customers who would be within earshot of my humiliating episode. Whenever one customer would leave another one would walk through the door to browse the shelves or get in line.

I tried to distance myself from my mother as we waited in line but whenever I wandered too far, she'd take a hold of my belt and pull me closer.

The burly clerk with a two day beard growth asked my mother how he could help.

"I need to buy a carton of Virginia Slims Menthols for my son here, and I'll take a carton of Marlboro Light 100s," she said as she rubbed my shoulders. "He's only 16 but he already smokes as much as I do."

The burly clerk's name was Chip. I knew this because he was wearing a name tag. The look on Chip's face said he wasn't amused but he was confused. "You want to buy cigarettes for your son?" he asked.

"Yes," my mother said. "Its not against the law if I buy them for him. You can look it up if you don't believe me."

"Yeah, I know," Chip said. "Its just that I don't get many parents coming in to buy cigs for their kids. What kind did you say he wanted."

Mom nudged me and told me to tell him what kind of cigarettes I wanted.

I croaked out the name of the girly cigarettes. "Virginia Slims Menthols," I said.

Chip grinned and and asked, "Full flavor or lights?"

"Full flavor please."

"Do you want the soft pack or the crush-proof purse pack?" he asked.

My mother answered for me. "You better get him the crush-proof pack, she said. "Darren left his cigarette case at home along with his purse."

Chip was clearly disgusted but he kept his comments to himself as he turned around and pulled two cartons of cigarettes from the shelf behind him. "Will there be anything else?" he asked as rung up the cigarettes on the cash register.

"I think that will do for today," my mother said. She paid Chip and picked up the cigarettes off the counter and handed me a carton before spiriting me out the door.

I should have been mad at her. She had made fun of me and had paraded me as a sissy in public, but I wasn't angry. As painful as that had been, the meat of the matter was that I didn't know any of those people. I'm sure they all thought my mother was kook and I was a big sissy, but so what? Who cares what they think?

Mom looked at me as she started the car and we both burst out laughing. "That was real funny," I said as I hurried to light a cigarette.

*****

"What kind of stuff do we need to get?" I asked as we walked through the front entrance of Pine Valley Mall.

"Just a few things," she said. "We're not going to spend too much money today. At least I hope not."

I told her that was probably for the best since I'd never be Megan again after tomorrow. Mom sighed and looked sad when I told her that.

"Whatever," she said as we stopped in front of a mall directory.

"What are you looking for?" I asked.

"The wig store," my mother said. "Brenda at the salon told me there was a store here that had good prices and a large selection. We don't want to mess up your Nancy hair for this. Oh! Here it is," she said as she placed her finger on the map. "Its right around the corner."

*****

All I saw was a lot of hair on the shelves but Mom was able to narrow it down to four choices. "What do you think about these four?" she asked.

"Why do we need four?" I asked. "Its not like Megan is going to be around after tomorrow."

"These wigs aren't for Megan," she said sadly. "They're all for Nancy because Nancy needs to grow up. Are you starting to get the picture yet?"

I was confused and told her so. "What about Megan?" I asked.

"We're going to Mexico next wee. You don't have time to be both. Its one or the other."

"But Nancy already has a wig and she's already grown up," I said. "I don't get why we need three more wigs."

"You're right," my mother said. "Nancy is grown up, but 30 years ago she was 16, and that was in 1981, not 2011. Are you starting to follow me yet?"

I was smart enough to do the math, but I was still lost. "Are you saying you want me to dress up like a younger version of Nancy?"

"Now you've got it!"

"But why? What good would that do?" I asked.

"So we can take pictures of you when you were younger," my mother said. "We'll need to take the wigs back to Brenda's and let her give them a retro makeover. You're going to need styles for the 70's, 80's, 90's, and 2,000. We're going to make a photo album for you so that Nancy will have a history. We need all kinds of pictures. We need baby pictures and toddler pictures. We need pictures of little Nancy on her first day of school. We need pictures of Nancy as a teenager. Now are you starting to get it?"

I was starting to get it and I was more than thrilled. I was starting to see everything my mom was talking about- the reason we were here in the first place! Yes, my mother wanted a daughter named Megan but she also wanted Nancy to have a life documented with photos.

I embraced my mother and squeezed her tight. "Mom! I don't know what to say. You're brilliant!"

Mom laughed and said, "I'm glad you're finally starting to appreciate me."

"What are you talking about? I've appreciated you every day of my life. That's why I want to be like you!"

She smiled and kissed me on the cheek. "I know you do, Honey. And that's why I want to make sure you have everything you need to start your new life out right. The doctors will handle the surgery. The lawyers will handle your identity. And I'm going to give you a history you can be proud of."

"You're the best Mom. I never would have thought about this in a million years!"

Mom picked up the brunette wig and said, "Neither would I. It was your father's idea."

"That was Dad's idea?"

Mom nodded and said, "He called me when you were getting changed for school this morning. I told him about wanting to dress you up as our teenage daughter and how you really didn't want to do it. He said I should forget Megan and concentrate on Nancy. It was his idea to give Nancy a photo history. He really loves you a lot, Honey, and he's behind you 100%."

I was stunned but I wasn't surprised, but I acted like I was. There was no way in the world that I'd ever betray my father's trust. "I'm really lucky," I said.

"Yes you are."

"Are you okay?" I asked. "You seem bothered."

Mom shook her head and said, "I don't know. I suppose so. Its just that I have my good moments along with the bad and this one is kind of bad. But don't worry, Sweetheart. It will pass."

"Is the bad moment about Megan or Nancy or me?" I asked.

"Its not Megan," she said. "Megan is just a dream of mine and its fleeting at best, but Nancy is real. She's permanent. And you're real too but I'm going to lose you to Nancy. I thought I'd gotten used to it, but seeing you like this, the way you were born, makes me think about how much I'm losing and how much you're losing. You're going to be a woman, Darren- an older woman, like me. And after we go down to Mexico next week, there's no back to the way you are now. Like it or not and for better or worse, you're going to be a 46 year old woman, and you'll have to live your life as one. It won't be a costume you can put on or take off. We'll be just like sisters."

"I know Mom. That's why I want to do it," I said.

"But what if you don't like it?" she asked.

I told her she didn't need to worry about that because it wasn't going to happen.

"But what if it does happen?" she asked. She put her hand on my chest and said, "You're going to have saggy boobs and a vagina like me." She touched my cheek and said, "Your skin is already getting soft from the hormones and next week its going to be wrinkled and aged. You'll have big fat womanly hips like mine." She touched the the pack of Virginia Slims poking out of my shirt pocket and laughed nervously. "You know you're the last person in the world who I ever thought would take up smoking. You were such a terrific athlete and look at you now. You smoke as much as I do."

My penis stiffened and I swooned as my mother talked about my becoming more and more like her. And the best part was that it was so close at hand! How could I ever regret becoming like her. She was my hero for crying out loud!

"I'm going to like it Mom because its what I've always wanted."

"I know its what you want but what if you're wrong?" she asked. "My life isn't nearly as glamorous as you think it is."

I told her it wasn't about the glamour. "I mean, sure, I'm not going to lie about it. I think you and your friends are sexy as hell but its not about the glamour. Its about feeling good about myself and I do feel good about myself when I'm Nancy. And if I can feel good about myself then everything else is going to work out too. Don't you think?"

Mom nodded sadly. "If that's the way you really feel then I believe it will work out for you." She handed me two of the wigs and kept the other two for herself. "I don't know about you," she said, "but I'm dying for a cigarette. "Lets just buy these wigs and get out of here."

"So you're really okay with me not being Megan?" I asked.

"I'll admit I'm disappointed but I think we're making the right decision. There's just not enough time to do both."

"What about your wedding dress? Can I still try it on?"

"No, but young Nancy can. And who knows? Maybe some day we can go shopping for a wedding dress of your own."

I blushed and Mom sensed my embarrassment. "I think you'd make a beautiful bride," she said. "And any man would be lucky to have you as his wife."

*****

Mom and I left the mall after buying four blonde wigs of different lengths. The plan was to drop the wigs off at Barbara's and hit a vintage clothes store that carried used clothes from past decades. Thanks to Dad and my photoshop skills, Nancy would have a past life. I figured I could use pictures from the web for my baby, toddler and elementary school years. The rest of the pictures would be of me dressed as Nancy from teenage years and up. I'd use different make-up, clothes and wigs to age from 16 to 40. It was a great plan but it was going to take a lot of work, and we'd need to take all the pictures before I went to Mexico.

I was excited about giving Nancy a documented life that would make her seem less mysterious, but I was bothered and flustered by the things my mother had said about any man being lucky to have me as a wife.

My date with Tim Moreland was less than two days away and I still hadn't come to terms with my feelings about going on a date with a man. It was awkward enough that he was almost 40 years my senior, but worse than that, Tim is a guy and so am I.

It was one thing for men to find me attractive. I was onboard for that. I mean who wants to be an ugly woman? Thinking about men made me think about fishing. I loved to fish but I didn't like to eat fish and I sure as hell didn't want to clean them after I caught them. Maybe it was the same way with men. On the other hand, maybe it shouldn't be that way.

Hanging around my mom and talking to her about life made me realize that my becoming Nancy could be a costume for life or it could be a life. And like she said, this woman thing was going to be permanent and I'd have to make the best of it no matter what.

Did I really want my life to be a game of dress-up and masturbation? Speaking of masturbation, after next week, jacking off was going to be a memory. The only way I was going to get any kind of sexual relief was with a vagina and Dr. Girardi said it wasn't guaranteed. There was a very real possibility that I'd never have another climax after the castration. I didn't like thinking about it in those terms but I understood the risk and I was willing to take it.

I remembered what my parents had said about it being okay to date men- older men. They had given me their permission and I had taken them up on it when I accepted the date with Tim. But Tim was like a fish and our date was going to be like catch and release. But what if it wasn't? What if I tried to clean him and eat him for dinner?

The thought of kissing Tim and possibly doing even more was gross and disturbing but it was also exciting. My penis grew hard as I thought about kissing him. What would it feel like to kiss him? What would it taste like? He was a smoker after all, but so was I. Maybe I wouldn't even notice the taste, but I would notice he was a man- an older man. Tim was old enough to be my father and that was gross, but that was because I was thinking about it from my point of view as Darren. On the other hand, how could I think about it from any other point of view? Getting a sex change isn't the same thing as getting a brain transplant.

I closed my eyes and imagined myself with Tim. I imagined us in bed together. He was naked and I was wearing one of my mother's nightgowns. I felt his hands on my breasts and the taste of his tongue as he pushed it inside my mouth. I could smell the smoke in his hair and taste it on his breath. It was gross at first but I imagined myself getting used to it.

That look on his face. I'd seen it before or more accurately, I had imagined that look on my own face as I willed a girl to touch my penis. And now I was seeing that look on Tim's face as he willed me to place my hand on his penis and squeeze it ever so gently with love and respect.

I suddenly found myself wondering what a 50 year old penis looked like. I imagined the pubic hair was gray. Did it look like mine? I was circumcised but what about Tim? I'd seen pictures of uncut dicks on the web and they disgusted me. I knew it was normal and natural but it was foreign all the same. I found myself hoping that Tim had a normal looking circumcised penis.

One imaginary thought rolled into the next and I found myself wondering how big Tim's penis was. Although I'd never admit it, I'd measured my own penis on occasion to see how I measured up to my friends' boasts and the stories I read on the web. I had decided that I was somewhat average. Would Tim be average?

Thoughts of his size evolved into thoughts of his hardness. I'd seen commercials on TV for drugs like Viagra and most of the men in the commercials seem to be around Tim's age. If wondered if he'd have to take a pill before we had sex.

Sex? Why was I even thinking about sex, especially with Tim? I wanted to flush the thought from my mind but I couldn't. I saw him climbing on top of me in the missionary position. I saw myself reaching for his penis and guiding it into my brand new vagina. I wasn't a virgin but in this case I would be. Is it going to hurt, I wondered? Or will it feel good, like the way I felt when I was the one putting my penis into a girl's vagina.

I began to hate myself for thinking of such things and I wanted to stop but I couldn't. Why in the hell was my penis so damn hard? Did this mean I was really gay? Maybe I'd been gay my whole life and just didn't know it.

"You've been really quiet," my mother said. "Is something bothering you?"

My mother's voice shook the thoughts of Tim from my head. "What did you say?"

"I was just saying you were awful quiet and I was wondering if something was bothering you."

I told her I was just thinking about stuff and then I lit a cigarette. The mentholated smoke tasted good and I hoped it would wash away my thoughts of Tim, but it didn't. I was still thinking about what it would be like to be in bed with him.

"Do you want to talk about it?" my mother asked.

I told her I didn't think so. "Its kind of embarrassing," I said.

Mom laughed and said, "In that case I need to know. Come on and tell me. Remember what I said about embarrassing things not killing you?"

"They only make you stronger," I said.

"Then go ahead and tell me. Make yourself stronger."

"Its just that I was thinking about my date with Tim and I'm afraid I'm not going to do things right."

"What kind of things?" my mother asked.

I rubbed my eyes and sighed.

"Well?" my mother asked. "What is it? Were you thinking about kissing Tim and having sex with him?"

My heart jumped and my stomach fell to my ankles. Was I really that obvious or could my mother read my mind. "Yes," I croaked.

The earth stop revolving around its axis for one brief second. Traffic stopped, the birds quit singing and clouds of shame enveloped me.

"Oh Honey! That's wonderful!" my mother squealed. "You really are meant to be a woman. I'm so happy I could scream! All this time I've been so worried about you. I was so afraid you might be making a mistake. I didn't want you to wind up miserable and lonely and full of regrets. But this changes everything!"

I broke down and cried while I listened to my mother go on and on about what a wonderful thing it was that I wanted to have sex with a man. She was right. This did change everything and it was all because of one little word. I had said "Yes" when my mother asked me if I was thinking about kissing Tim and having sex with him.

I was so upset that I hadn't realized the car had stopped and were sitting in the parking lot of Vintage Closet.

My mother pulled a kleenex out of her purse and wiped away my tears, but for every tear she wiped away, I cried a new one. "I can't go in the store like this," I said.

"Its okay, Honey. We can just sit here and talk until you're up to it."

"But I don't know if I can talk about it without crying. I don't know what to do Mom. I'm so scared. Its like I don't know who I am any more."

"Yes you do," my mother said. "You know who you are and you know who you're meant to be. You're a middle aged woman stuck in a teenage boy's body, but we're going to fix that. It won't be long until you're a real woman just like me."

"I want that so much Mom."

"I know you do sweetie and I want it for you too."

"But I'm so afraid I'll mess up and do the wrong things. I don't know how to be a woman for a man. What if I mess up or I'm not good at it?"

"First of all, this isn't a race," my mother said. "You don't have to have sex with Tim on Saturday night. He's not expecting it and you're not mentally or physically prepared for a sexual relationship. This is something we can take our time with."

I sniffed and dried my eyes. "Okay, I said."

"So tell me. Are these new feelings or have you had them all along?" my mother asked.

I told her I wasn't sure but that I thought I'd been having them all along. "I just didn't want to think about it," I said. "I didn't want to believe I was gay and I still don't think I am." I asked her if she thought I might be bisexual.

"Its possible," my mother said. "Then again it could be the hormones. Dr. Giardi said you'd begin to feel and think more like a woman."

"It so confusing!" I said.

"I'm sure it is," my mother said. "But we'll figure it out together. I see you've stopped crying. Are you starting to feel better."

"No. Not really, but I'm glad I finally told you. I've been wanting to tell you for a long time but I didn't know how."

"Well I for one am thrilled that you told me. I know it doesn't make sense now, but it will some day and when that day happens, it will feel like the most natural thing in the world."

There's something else I want to tell you," I said. "Its something that I've been thinking about forever and I was afraid to tell you because I thought you'd laugh at me."

"Then tell me now while you're on a roll. I promise I won't laugh."

"I want to be a mom. You know, a real mother like you and have kids. Isn't that crazy?"

"I don't think it sounds crazy. As a matter of fact, I think it sounds wonderful," my mother said. "And I think you'd make a wonderful mother."

"You really think so?" I asked.

"Absolutely! And I also think you'd love it. Being a wife and a mother are the two best jobs in the world and I wouldn't trade them for anything."

I wiped at my eyes and forced a nervous laugh. "I hope I marry a man with a lot of kids because I'm not going to get them any other way," I said.

****

After regaining my composure, Mom and I went shopping inside My Vintage Closet. I couldn't believe how much they wanted for 30 year old clothes, but I knew they were worth every penny. Mom and I walked out with three shopping bags full of old clothes.

"If we hurry, we can make it back to Brenda's salon before she closes. I'd like to get a head start on taking pictures," she said.

Like Mother Like Son 12

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Voluntary

Other Keywords: 

  • Older Woman Envy
  • Mother Admiration

Permission: 

  • Posted by author(s)

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?

**************
Chapter 12
**************

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.

Like Mother Like Son 13

Author: 

  • Sharon Parsons

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Voluntary

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • Older Woman Envy
  • Mother Admiration

Permission: 

  • Posted by author(s)

16 year old Darren Peterman, AKA Nancy, has just been stood up by her date, Tim Moreland. His little brother Sammy has his own female problems. Darren's Mom, Karen, thinks that she and Nancy should make the best of the situation and have a girl's night out.

************
Chapter 13
*************

So I'd been stood up by Tim. Perhaps this would be par for my future dating life. After all, he did think I was a middle aged woman. Although my perceived age might have played a role in theory, it wasn't a factor here. Tim had gone back to his wife. Of course I'd never met the woman but it made sense to think she was probably in her forties. I knew I shouldn't take the rejection personally but I was.

My parents and Sammy did their best to console me. Sammy said that I deserved better. Mom and Dad agreed.

I was about to call it a night and go to my room, even though it was only slightly past six, when my dad suggested I could still go out. "You and your mom could have a lady's night out," he said.

Mom jumped on his suggestion and said it was an excellent idea. "There's no use sitting around the house and feeling sorry for your self," she said.

I asked her where we'd go.

"You and Tim were going to see a movie and then go to Johnny's Hideaway for drinks and dancing. "What do you say we skip the movie and go to Johnny's. Your father and Sammy and could drop us off and we could take a cab back."

"So at least I could get drunk," I said.

"Me too," Mom said. "That's why I thought your dad could drop us off and we could take a cab back."

A plan was made. Mom got her self ready while I hung out with Dad and Sammy. I wouldn't call it an interrogation, but Dad and I asked him some very personal questions about his wanting to be a girl and he seemed to have an answer for everything. I was beginning to think that Sammy's becoming a girl might be for the best, but then again…what did I know?

*******

As mom and I were walking into Johnny's Hide Away, she said "I shouldn't have to remind you of this but I can't help myself…just remember to call me Karen tonight."

"Sure thing, Karen," I said as I allowed her to walk though the door first. An older man in his sixties was on his way out as we were walking in and he held the door for us. We thanked him and he leered at us as we walked inside. I thought the guy was a perv but Mom seemed to get a kick out of it.

"Don't get too carried away," I said. "I doubt your husband would like the idea of other men ogling you."

"As long as they just ogle," my mother said. "Ogling is innocent and it makes me feel good. Keep in mind, I've been old for a long time, so I appreciate a flirt and a look."

I told her I was just kidding about "Bill" getting mad. "I'm sure he wants you to have fun tonight and so do I."

"Thanks, but your fun is more important than mine tonight. We just need to throw back a few drinks, have some conversation and do a little man watching," she said as she led us across the crowded dance floor to a booth overlooking the bar and dance floor.

I'd never been inside a bar before so I was a little awe struck. Obviously, I'd been in family restaurant/bars before, like Applebee's, but this wasn't Applebee's. It was dark and smoky. The place was built from wood and brass and mirrors. People sat along the bar drinking and talking. There was a live band and older couples were dancing to the music. It looked like something out of the movies, but the thing that caught my attention the most was all of the old people. The bar was crawling with men and women over forty. And the real crazy part was that I looked like I fit in with them.

"So is the first time you've ever been inside a bar?" Mom asked as she lit a cigarette.

I admitted that it was as I removed a cigarette from my case and lit it. "I've never seen so many older people in one place," I said as I exhaled.

"That's why people call Johnny's a middle aged meat market," Mom said. "You like it. Don't you?"

"I like it a lot," I said. "I feel like I fit in and I love being here with you like this. Its like we're really sisters."

Mom reached across the table and put her hands on mine. "I feel like we're sisters too!" she said. "I can't believe how close we've gotten since this started. Promise me that we'll only get closer," she said.

I called her Karen and told her she was my best friend. "I hope this doesn't sound too weird," I said, "but this is how I alway imagined it would be between us. You know…me being an older woman and us being peers and best friends."

Mom raised an eyebrow and smiled. "Yeah, me too," she said sarcastically. I had it all planned from the moment I gave birth to you. As soon as I saw your face, I told your father that I was going to turn you into a woman so that you could be my best friend."

"I guess this has been kind of crazy for you," I said.

"You could say that," Mom said. "But I don't know whose crazier. You for wanting to be an older woman or your father and I for letting you do it. The funny thing is that it doesn't feel crazy. It feels right. I just wish I felt the same way about your brother."

"So you don't think Sammy should be a girl?" I asked.

"To tell you the truth, I don't know what to think about Sammy. Right now I'm just treading water until it starts to make sense. He put your father and I in an awkward situation, so until we figure it out…"

"But I was there when you and Dad gave him permission to smoke and be a girl," I said. "You can't tell him he can do it and then tell him he can't."

"You're right. We can't do that, but we can't let him destroy his life on a whim either. You heard the way he was talking back at the house. He's all ready to throw on a dress and smoke cigarettes in front of his friends. That's a big change from being Sammy. Don't you think it would be better if we let him ease into it and try it on for size before we let the horse out of the gate?"

"So you and Dad are still going to let him smoke and dress like a girl but just not all the time."

"That's the plan for now," she said. "! I haven't talked to your father about it yet, but I was thinking he could have his girl time after school in the privacy of our home and then maybe go out in public whenever we think its safe for him to dress up."

"Yeah, I guess that makes sense," I said. "I don't want him screwing up his life either."

"Then that makes two of us," Mom said, "but just so you know, I'm not against his wanting to be a girl."

"Really? You could have fooled me," I said.

"Was I that obvious?"

"Kind of, but that's okay. I'm sure Sammy didn't mind and I know how much you want a daughter."

I crushed out my cigarette and lit another one as the waitress came over to take our order. I wanted to try a beer but mom asked for a carafe of wine and two glasses. She lit a cigarette after the waitress left.

"Hello. Mrs. Peterman?"

Mom and I looked over and saw Mr. Edwards, my former guidance counselor, standing just a couple feet away.

"Mr. Edwards! How are you?" Mom asked nervously.

"Fine, thanks. I hope I'm not interrupting. I was just sitting over at the bar and I thought I recognized you and I wanted to ask how Darren is doing?"

"Nancy and I were just talking about him. He left for Alaska this morning. Oh! How rude of me. The two of you haven't met. Mr. Edwards, this is Nancy Peterman, my sister-in law. Nancy, this is Mr. Edwards. He was Darren's guidance counselor."

Mr. Edwards smiled and extended his hand. "Its a pleasure to meet you Ms. Peterman."

"Please, call me Nancy," I said. "Would you like to join us Mr. Edwards?"

"I don't want to interrupt," Mr. Edwards said.

"Don't be silly," Mom said. "Nancy and i would enjoy the pleasure of your company."

"Well in that case, I'll get my drink and cigarettes. I left them at the bar and please call me Ken."

"And you can call me Karen," Mom said.

Mr. Edwards almost tripped over his feet as he dashed off to the bar. "Are you sure want him to join us?" Mom asked. "You just saw him yesterday. It could be kind of dangerous."

I shook my head in disbelief and said, "Yeah, I know. I can't believe I did that either. I'm not sure what I was thinking."

"Well maybe it won't be that bad," Mom said. "And if worse comes to worse and things start getting awkward, we'll just tell him we need to leave."

Mr. Edwards made good time and I scooted over in the booth to make room for him. He thanked us again for letting him sit with us. He told us that he didn't make the bar scene often and was uncomfortable with it. Mom and I were both looking at his wedding ring as he spoke.

"What about your wife?" Mom asked. "Doesn't she like to go out?"

Mr. Edwards looked down at the ring on his finger and sighed. "My wife, her name was Jill, she passed some time back and I never got around to taking off the ring. Do you think its disrespectful of me to be wearing it in here."

"I wouldn't call it disrespectful," Mom said. "However, a ring on your finger doesn't send out the right vibe if your looking to meet women. How long has it been since she died, if you don't mind my asking?"

"It will be four years in July," Mr. Edwards said.

I asked Mr. Edwards if his wife had been sick.

"No. Nothing like that. It was a freak accident. A tree limb fell on her while she was walking the dog."

I didn't know what to say and judging by the look on my mother's face, she was at a loss for words too.

"Did you say a tree limb fell on her?" I asked.

Mr. Edwards nodded sadly and asked, "Do you remember that bad drought we went though several years back? Well, that's what they said caused it. The tree got sick and weak and the branch just happened to fall as Jill was walking by."

Mom and I both told him we were sorry as he twisted the ring from his finger and moved it to his pants pocket.

"What about you Nancy? I don't see a ring on your finger. Were you ever married?"

Mom took a deep breath as I embarked upon a lie. I'd lied before and I'd lie for the rest of my life, but I realized the lies needed to be uniform. I'd made up a story about being married and having a child when I met Tim Moreland in the park. I wasn't going to do that again. The less people in my life that I had to account for the better off I'd be.

"Never married and never had children," I said with conviction.

Mr. Edwards nodded as he picked up his pack of Marlboros. "Does that mean you're married to your job?" he asked.

I knew I needed a job. After all, I was a 46 year old unmarried woman. So how had I been supporting myself all these years. "I've had several jobs but I've never been married to any of them. My last job was as a receptionist in Birmingham but I got laid off. That's why I moved here. I'm staying with my brother until I can get back on feet."

"Nancy is helping me with my real estate business," Mom said. "I'm hoping I can talk her into taking the exam so that she can be an agent."

"Real estate? That's a tough job with today's economy," Mr. Edwards said.

"It is," Mom said, "but the market is coming back. Its just coming back a little slower than we'd like."

Mr. Edwards asked my mom a question about the real estate business and I pretended to be interested. However, real estate was the last thing on my mind because I was totally lost in the situation at hand.

Here I was sitting in a bar with my mom and my former guidance counselor and I was dressed like a middle aged woman.

I got a squishy-tingly feeling in my groin that spread to my finger tips as I admired the classy looking cigarette case that I would need and use every day for the rest of my life. In many ways I think the Louis Vuitton case was a badge of my adult womanhood. A teenage girl, much less, a teenage boy would never possess such a trophy. Only an adult woman who had been smoking proudly for many years and had no intention of quitting would ever make such a large investment in an item designed solely for stylish self-destruction.

The awe and wonder I was feeling didn't end with the cigarette case. I could clearly see my reflection in one of the many mirrors positioned around the bar and I saw a two attractive middle aged women sitting in a booth with a balding middle aged man. And one of those middle aged women was me!

I shifted in the booth and felt my silky panties slide across my skin as my artificial breasts swung and settled according to the laws of gravity. The padding I was wearing made me feel curvy and substantial without being fat. I loved looking as if I had a little mileage on my chassy.

I tried my best to look at ease as if I'd been a woman all my life and I did look at ease, but I didn't feel that way. Suppressing my excitement was almost painful. I wanted to tell everyone what I was doing so that they could share in my excitement, but of course I couldn't do that.

I took a sip of wine and reached for my cigarette case. Mr. Edwards must have been watching me out of the corner of his eye even thought he was deep in conversation with my mother. He paused their talk just long enough to offer me a smile and a light. I thanked him and exhaled toward the ceiling. The squishy feeling washed over me.

In addition to feeling plain ole excited and turned on, I was also feeling proud of myself, not because I was pulling the wool over Mr. Edwards eyes but because I sincerely felt proud to be expressing myself as an older woman. Being Nancy was as much of a labor of love as it was sexually stimulating.

I devoured the attention and respect Mr. Edwards was pouring on me. The man had just lit my cigarette. Would he have done that for a teenage boy? I didn't think he would. But Mr. Edwards didn't see me as a boy. He saw me as a woman and a lady and I liked being seen that way.

His eyes followed my hands as I brought my cigarette to my lips. Was he thinking about what it would be like to kiss me? Wouldn't that be funny because I was definitely wondering what it would be like to kiss him, and now it turns out he isn't married.

As far as looks were concerned, Mr. Edwards paled in comparison to Tim Moreland. Tim was at least 2 or 3 inches taller and 30 pounds lighter than Mr. Edwards. Besides that, Mr. Edwards was going bald and wore glasses. But none of that mattered to me because I had always seen something more in him than just his looks.

The man had been my guidance counselor for nearly three years. Granted I never made much use of him as a counselor but when I had, he'd always been nice to me. Beside that, I wasn't the only one who thought he was a great guy. Everyone in my school seemed to love him. But on the other hand, I was probably the only one from my school who was thinking about kissing him.

I shuddered with a mixture of attraction and repulsion as I watched Mr. Edwards shake a Marlboro loose from his pack and light it. I had never kissed a girl that smoked, much less an adult man.

I smiled to myself as I pondered my warped obsession with smoking. Was it feminine or masculine? Was it trashy or classy? The answer always depended upon who was doing the smoking. I marveled at the irony as I inhaled a dose of mentholated smoke.

Two weeks ago I would have been afraid to ask a girl who smoked for a date because of my mother's feelings. She didn't like me associating with kids that smoked because she thought they were a bad influence. My how things had changed!

My ears perked up as I detected a change in the conversation between Mr. Edwards and my mother. She was telling him about Sammy and was asking for his advice.

"I know you're not a doctor," she said, "but I was wondering if maybe you've come across something similar as a counselor?"

Mr. Edwards bit his lip and nodded. "As a matter of fact, I've had the opportunity to work with several students with transexual issues. And I'll say this…It's just as difficult for the parents as it is for the child. The best advice I can give you and your husband is to be tolerant, supportive and understanding. Sammy could be going through a phase, and if that's the case, he'll do a lot better the less bad you make him feel about himself. And if its not a phase, you'll be doing him a great favor by making this easy for him. Have you taken him to see a specialist yet?"

"Not yet," Mom said, "but I do know a doctor who specializes in gender disorders. I'm going to call her on Monday but I was just looking for some advice on how to handle it in the meantime."

"It sounds to me as if you and your husband are doing the right thing. Just try to keep him grounded and reasonable until you've had a chance to have a doctor evaluate him," Mr. Edwards said.

Mom thanked Mr. Edwards for his advice while she fidgeted with her cigarette case. "There was something else I wanted to ask your advice on," she asked. "This is going to sound bizarre at best, but Sammy has gotten it into his head that smoking is well.. He thinks it looks feminine and kind of sexy. What do you think about that?"

Mr. Edwards blushed noticeably as he was clearly uncomfortable with my mother's question. "You want to know what I think?" he asked.

"I suppose that did come off somewhat confusing," my mother admitted. "Its just that Sammy has started smoking and he's so young, but I think he's addicted, and well… this is going to sound flat out crazy but he says he feels feminine when he smokes."

"And you and you're husband are debating whether or not to give him your permission to smoke?" Mr. Edwards asked.

It was my mother's turn to blush and so she did. "You must think I'm a horrible mother," she said. "First one of my son's takes up smoking and drops out of school and now my youngest son takes up smoking and wants to be a girl."

"No Karen, I don't think that all. If anything, I think you're a great mother. I'm a parent too and I know this isn't a perfect world. As parents and people we have to play the cards we've been dealt and I think that's what you've done with Darren and now you're doing it with Sammy."

Mom sighed and asked, "So are you saying you think its okay to let Sammy smoke and dress like a girl?"

"I don't think I'd go on record as saying its 'okay'," Mr. Edwards said. "If it were me I don't think I could ever give any of my children permission to smoke, but its not me and your situation is different and the last thing I want to do is make you feel like I'm judging you because I'm not. I think I'm trying to say you should accept the situation for what it is and do your best to control the damage. That probably sounds like a cop out on my part but its really the best I can do."

Mom shook her head and told him she didn't think he was coping out. "What you said makes a lot of sense," she said. "As a matter of fact I was pretty much thinking about it the same way."

"The important thing to keep in mind is that's its not the end of the world. As far as the smoking goes, well…you obviously smoke and so does Nancy and it certainly doesn't make you bad people. I'd even go as far as to wager that you both started smoking when you were Sammy's age. And I seriously doubt you're going to love your son any less if he's transgendered or a crossdresser."

"You're right and I agree with you," Mom said. "It just feels good to hear another person say out loud the things I've been thinking."

Mr. Edwards turned to me and said," See what you've been missing by not having kids?"

I responded with a polite laugh but followed it up with a sincere thought that countered his statement. "I can't imagine how difficult it is to be a parent," I said, "but I think I'd give almost anything to find out. I know it probably sounds crazy at my age, but I'd like to be a mom."

Mr. Edwards grinned and threatened to take me up on it. "I have two boys and one girl who could use a mother," he said.

"Really? How old are they," I asked.

"Lars, my oldest, is 16. Ben is 13 and Abby is 11."

"Does Lars know Darren?" Mom asked.

"No. We live in the Henderson district. As a matter, Lars took quite a beating against Milton last night. I suppose the score might have been even more lopsided if Darren had played." He turned to my mom and said, "By the way, I don't think Coach Holloway's contract is going to be renewed next year. He's a good coach as far as football is concerned but his temper makes him a liability."

Mom and I listened and asked questions as we talked to Mr. Edwards about his children. He was clearly proud of them and rightfully so because they sounded like good kids.

During a pause in the conversation, Mom touched my hand and said she needed to visit the ladies room. "Come with me," she said. We excused ourselves and Mr. Edwards slid out of the booth so that I could get out.

"Don't go away. We'll be right back," Mom said. "And if you see the waitress, would you be a dear and order us another carafe of wine."

"House white?" Mr. Edwards asked.

"Please," Mom said as we grabbed our purses and left for the bathroom.

Mom grabbed my arm as soon as we were out of earshot and said, "You like Ken. Don't you?"

"Why would you think that?" I asked. "He's my guidance counselor for crying out loud."

Mom corrected me by saying he 'was' my guidance counselor. "I saw the way the two of you were looking and smiling at each other," she said. "I think there's something there."

I argued that I was just being polite. I felt a spot of wetness on my cheek and wiped away a tear.

"Don't fight it 'Nancy" and don't be embarrassed by it either," Mom said.

"Okay, maybe I do kind of like him a little," I said as I followed her into the bathroom. "Was I being that obvious?"

Mom put her purse on the sink and took out her cigarettes. "That's what people do when they flirt," she said as she lit up. "They're obvious about it. That's how flirting turns into dating."

I turned and looked at myself and my mother in the mirror as I pulled out my cigarettes. "I can't believe this is really happening," I said as I lit a cigarette. "How do I look? Do I look okay?" I asked nervously.

Mom grinned and shook her head. "You look beautiful, Honey. I think so and so does Ken."

"He really thinks I'm an older woman, doesn't he?"

"Of course he does, and why wouldn't he? Your make-up and body padding is perfect! But its more than how you look. Its everything else and you're doing it all perfectly. The way you talk and the way you move your hands around while you smoke, you've got the whole thing down pat!"

"Do you think he really likes me?" I asked. "I don't want to go back out there and think he does when doesn't and wind up making a fool out of myself."

"Don't worry about Ken. I've been a woman longer than you have and I know when a man is attracted to a woman, and he's definitely attracted to you. I'm more worried about how you feel about this. Are you sure you want to go back out there? Because if you don't, we can tell him we need to leave."

"You don't think I'm ready. Do you?"

"I didn't say that and I'm not thinking it either," Mom said. "I just want to make sure that you think you're ready. We've had a good time tonight and we had fun without things getting out of hand. But that could change if you go back out there and he asks you out."

"I think I like him Mom. As a matter of fact, I'm sure I do. And I think I've liked him for a long time, like since I was a boy."

Mom bit her lip and shook her head. "Oooh Sweetheart. This is getting dangerous. He has three children, or did you forget that?"

"I know he does."

"Have you thought about what could happen if you and Ken get serious? You could wind up being a mother to three teenagers. I know you think you want to be a wife and a mother like me, but raising teenagers is a lot harder than raising young children, especially if you're a teenager your self, which you are."

I thought about my mother's words even though they weren't news to me. I had already touched upon them when Mr. Edwards mentioned having children. The idea of becoming a mother to three teenage children didn't turn me off in the slightest. "I think it would be kind of fun," I said.

"Fun?"

"Yeah, like as in weird or kind of cool," I said.

Mom grinned and cocked her head. "Only you would think something like that," she said. "Don't tell me. Let me guess. You're excited by the taboo and bizarreness of the situation, aren't you?"

I blushed and shrugged my shoulders.

"This is your life and I'm not going to tell you what to do with it," Mom said. "I just want you to be happy and I agree with some of the things you're doing but not all of the things you're doing, but like I said, this is your life. But I'll tell you something I've learned from experience. Nothing stays new and shiny forever but you're still stuck with it after the luster wears off. Do you understand what I'm trying to tell you, or do I need to be more clear?"

"I get what you're saying but I can't help wanting what I want. But I promise you that I'll always make the best of it- no matter what."

"Okay," Mom said. "Like I said, its your life. So what do you want to do about the rest of the night? Do you want me to go home and leave you alone with Ken?"

*******

My mother and I returned from the bathroom and after some strategic bantering, Mom bowed out and left me in the care of Mr. Edwards. Needless to say, I was thrilled to be alone with him.

We talked about nothing. We talked about his children and his job at Milton High School. We talked about my fictitious life as well as Darren, my alter ego. We laughed and we smiled. He lit my cigarettes for and poured my wine. He was a gentleman and he treated me like a lady.

I felt like a middle-aged Disney princess. Johnny's Hide Away was a magical ball room and Mr. Edwards was my balding Prince Charming. The tingly-squishy feeling pulsated from my groin.

This is what respect and admiration feels like I thought as I lifted the cigarette to my lips and gave it a feminine pump. Feelings like those had eluded me as a boy but as a woman they washed over me.

I looked around the nightclub as I talked to Mr. Edwards. An occasional admiring eye would fall upon me and I knew they were seeing an attractive middle-aged woman on a date with her boyfriend. Or maybe they thought he was trying to pick me up. Regardless of what they thought about Mr. Edwards and I as a couple, they saw me as a respectable and attractive middle-aged woman and that knowledge stirred my groin.

I was obviously in the midst of one of my most coveted sexual fantasies which explained my arousal. What was there not to like? I was dressed up like my mom and I was smoking like a woman in front of an older man who had feelings for me.

As a woman with a boy's mind I knew exactly what Mr. Edwards was thinking. He was thinking that he'd like me to suck his dick. And he was also thinking about fucking me! Of course he thought I had a real pussy and why wouldn't he? I looked like I should have one and some day I will, I thought. I'll have a pussy just like my mom and then I'll really be like her! But what to do until then?

I laughed at something he said while I thought about offering him my asshole. Of course I knew I wouldn't do that, but still…I was thinking about it. I was thinking about him entering me while I laid on my back in the missionary position. No doggy style for me! Oh no. If I was going to let myself be fucked in the ass by a man then I'd be fucked as a woman and not some stray dog.

I reached for my cigarette case and withdrew a long white Virginia Slim. Did Mr. Edwards think I looked sexy with my girly cigarettes? I saw him shift in the booth beside me as he offered me a light and I steadied his hand with mine. The counselor had a hard-on and he had it for me.

"Thank you," I said sweetly as I exhaled toward the side of his face. He inhaled noticeably as he accepted my thanks. Why is it that men will breath in the second hand smoke of a woman but they'll cringe from the smoke of another man? I'm really a boy, Mr. Edwards, I thought as I took another puff and exhaled close to his face. How would you feel if you knew you were breathing the smoke produced from a 16 year old boy's lungs? I bet you wouldn't be smiling like you are now. Would you still want me to suck your dick if you knew the truth?

I cringed as I realized how mean spirited my thoughts seemed, but they weren't directed at Mr. Edwards. All the hostility was directed within. He wasn't the one betraying me. I was betraying him and he didn't deserve it. Mr. Edwards was a nice guy. He'd die from shame if he ever discovered the truth, which was why I needed to keep it from him.

I wasn't a psychopath. I knew right from wrong and what I was doing to Mr. Edwards was definitely wrong but that didn't stop my hormone inflicted penis from trying to stand up.

How do other transexuals handle this, I wondered? Are they forthright and upfront or are they cowardly and selfish like me?

I inhaled and touched my lips with my tongue before exhaling as femininely and seductively as possible. His eyes lit up and I knew I had him. He was mine and I had caught him and I wouldn't be throwing him back. I wasn't playing catch and release. I was playing for keeps.

His face tightened and a slight scowl formed at the corners of his mouth. Something was on his mind. What was it?

"I was wondering if you might like to dance with me?" he asked.

My toes were too tingly to dance but I accepted his request with a smile and the touch of my hand. He got up from the booth and led me to the dance floor. I didn't recognize the song but it was slow and I could tell it was old. He put his hands on my hips while I draped mine over his shoulders.

He was shy so I closed the distance between our bodies by nuzzling my face into his neck. He smelled like smoke and sweat and Old Spice. When I kissed his neck I felt his lips on my ear and I giggled.

I was dancing like my mother taught me, listening to the music and sensing his lead. Step softly, I thought. Step softly and be gentle. Move like a woman and use my hips.

When I felt his hand inch cautiously toward my ass, I raised my head and found his lips with mine. My kiss was an invitation to explore my body with his hands. Don't be afraid of me, I thought. I won't bite.

Anyone who saw the kiss wouldn't have thought much about it. After all, it wasn't one of those "get a room" public displays of affection. I didn't taste his tongue with mine but it was electric all the same.

I had kissed a man on the lips for the first time in my life and I knew it wouldn't be the last time. It was repulsive yet exciting. I was grossed out and turned on at the same time.

Time moved as slowly as the music as we danced beside the other couples. Our feet slowed and our dance became a gentle rocking hug. Our hips were close enough that I felt his penis swell against my thigh. He knew that I felt it and his face turned red as he apologized with his eyes.

I whispered in his ear for him not to be embarrassed. "I'm flattered," I said. And then I kissed him again on the lips. He was relieved by my gesture but he apologized any way.

I felt cheated when the song ended because he took a step back and let go of my hips. I missed being close to him and didn't like the separation. He thanked me for the dance and led me back to our booth while holding my hand.

Once we were seated, he lit my cigarette and one for himself. I noted that it was only his third cigarette of the evening while I had lost count of the number I had smoked.

"I either smoke a lot or you don't smoke much at all," I said as he returned the lighter to his pocket.

He grinned and said, "Maybe its a little of both. I'm kind of in the closet with my smoking so I don't smoke often, especially not in public. As a matter of fact, my children don't know and I'd appreciate it if you would keep my secret if you ever meet them."

"Why such a big secret?" I asked. "You're a grown man."

Mr. Edwards blushed and said, "I don't think my children see me as the smoker type. My wife was the smoker. I didn't take up the habit until after she died."

"If you don't mind me asking, why did you start?"

Mr. Edwards rolled his shoulders and exhaled toward the middle of the bar. "I started because I missed her and this is going to sound embarrassing, but my wife smoked Virginia Slims, the same as you, so that's what I started on." He picked up his pack of Marlboros and said, "I only started smoking these once I figured out I was hooked. Not that I smoke in public very often, but when I do, I don't think Virginia Slims would go over so well."

I smiled without laughing and told him that made a lot of sense. "They are kind of girly," I said as I paused to take a puff.

"What about you? Why did you start?"

I smiled as I thought about what I should say and then settled on the truth. "I started because my mother smoked and I wanted to be just like her. I guess you could say she's my role model."

"Well if she's anything like you then I'm sure I'd like her," Mr. Edwards said. "How old were you when you started?"

It was a simple question and I could have told the truth without getting in trouble but something inside of me pushed me to lie. I decided that since it was my make-believe life, I'd have some fun with it. "You're going to think I'm horrible," I said, "but I started when I was seven."

Mr. Edwards' eyes popped. "Seven! You're kidding. Don't tell me you were inhaling at that age."

"Oh yes," I lied. "You should have seen me. I was a mess. Every time I had the house to myself, I'd put on my mother's clothes and smoke her cigarettes and pretend I was her. I felt so grown up, smoking like a woman. I'm sure I must have looked like a stupid child but in my mind, I was a grown woman just like my mom."

"And did she ever find out?" he asked.

I bit my lip and nodded. "Oh yes. She found out. She caught me when I was 10, and by that time I was too hooked to quit."

"Are you saying your mother gave you permission to smoke when you were only 10 years old?" Mr. Edwards asked in astonishment.

I cocked my head and said, "That's my story and I'm sticking to it. But I'm more interested in your story right now. Do you hide your smoking from everyone or just your kids?"

Mr. Edwards took a deep breath and sighed. "Pretty much everyone," he said. "I guess you must think I'm pretty silly, huh?"

"No, I don't think you're silly," I said. "I think you're a very smart man with a good heart. We all have our secrets and some are worse than others. Yours doesn't sound very bad to me, but its yours and I'll keep it for you if you want."

"Thanks. I'd appreciate that," Mr. Edwards said. "I've got another secret I could tell you if you want to hear it."

"Oh really? What is it?"

"I think I like you," Mr. Edwards said. "And I'd like to see you again."

My head swooned and my heart jumped. Oh my God, I thought. He really does like me. "Are you asking me out on a date?" I asked nervously.

"I guess that just proves how bad I am at this if you have to ask. "Yes," he said. "At the risk of you rejecting me, I'm asking you for a date."

"I'd like that very much, but just so you know, I'm going out of town on Monday for a week and when I get home, I'll need some time to recover."

"Recover from what?" Mr. Edwards asked. "That is if you don't mind me asking. I shouldn't ask anyway. Its probably personal."

"It is personal," I said, "but I don't mind mentioning it to you. I'm having some surgery done in Mexico. Some of it is necessary and some of it is cosmetic. I figured I'd knock a couple of birds out with the same stone."

"So you'll be gone for a week?" he asked.

"Yes, but I won't feel much like seeing anyone when I get back. I'll be very sore and I'll probably look like a mummy with all the bandages that go along with the aftercare."

"And then I'll be able to see you again?" he asked.

"Maybe once or twice," I said. "But I have another surgery scheduled before Christmas. So what I'm saying is, these next two months are going to be kind of busy and a little painful and I wouldn't be very good girlfriend material."

"Is that a rejection?" Mr. Edwards asked.

"Not at all," I said.

"In that case, I'll accept it as an invitation," Mr. Edwards said. "Can I see you tomorrow or will you be too busy packing and getting ready for Monday?"

"I am going to be busy but I could spare an hour or so. How about lunch?" I asked.

"There's an Italian restaurant on Aberdeen street?" Mr. Edwards said.

"Aldo's?" I asked.

"Yes, thats it. How about you meet me there at 12:30 after church. I'll have my kids with me so it wouldn't be much of a date."

"That sounds nice. I'd like to meet your kids," I said as I looked at my watch. "Its getting late, but I think I have time for one more dance if you're up to it?"

******

The drive from Johnny's Hide Away takes less than 20 minutes which was not enough time for me to be alone with Mr. Edwards. I'd been in similar situations as a boy and had taken my time on many occasions. In a teenager's world it was expected for the boy to try parking with a girl.

I knew all the out of the way places a boy could take a girl to park. I wondered if Mr. Edwards knew about them. On the other hand, I realized Mr. Edwards might not think it was appropriate. After all, he wasn't a teenager. I also realized there was a very good chance that he was afraid of offending me, so he'd probably be on his best behavior, even though I didn't want him to be.

I knew I'd see him again on Sunday, but that would only be for an hour or so with his children in public. After that I'd be on a plane to Mexico. And after that I wouldn't be in a position to see him until my skin healed.

My new skin, I thought. Its going to look like old skin. I laughed.

"What's so funny?" Mr. Edwards asked.

"Oh nothing," I lied. "I was just thinking about when I was a kid in high school and the things we'd do after a date."

"When I was a kid, I used to like to get ice cream after a date," Mr. Edwards said. "Would you like some. There's a Dairy Queen on the way."

"No thanks. Besides, its probably closed," I said.

"So what kind of stuff did you like to do after a date?" he asked.

"It doesn't matter," I said. "It was a long time ago."

"I see an open Burger King," he said. "You want go through the drive-thru and get a milkshake?"

No, I didn't want a milkshake. I wanted something else but I said a milkshake would be nice and told him I liked Vanilla.

As we were pulling out of the drive-thru I told him about the park close to my house, the one I'd taken Sammy to. "There's a lake," I said. "We could go there and drink our milkshakes, unless you need to get home soon."

"I thought you were the one that needed to get home soon," Mr. Edwards said as he pulled out of the parking lot.

"Not that soon," I said. "I have a little time."

*****

Mr. Edwards parked in front of the lake and turned off the car. "Let me know if you get cold and I'll turn the engine back on."

I told him I was fine and scooted closer to him, which gave him the idea to put his arm around my shoulder. My milkshake was somewhat thin and melted from the drive but it still tasted good.

His fingers kneaded my shoulders as we talked about the stars over the lake. "Its really pretty," Mr. Edwards said. "I've never been here at night. Have you?"

"Not at night," I said. "But I've taken Sammy here to play with his friends."

"What made you think about coming here?" he asked.

As a male, I knew exactly what Mr. Edwards was up to. He was fishing for inspiration and trying to find his way with me. I knew from experience that he'd want to go as far as he could with me without going too far. He was just scoping out the boundaries.

I wondered what a real woman would say to such a question. Would she lie or play games or would she be forward and direct?

"I don't know. Maybe I just wasn't ready to go home yet," I said as I laid my hand on his thigh.

"I wasn't quite ready yet either," he said as he moved his leg so that his privates inched closer to my hand.

We spent the next several minutes quietly debating our next moves as we sipped our milkshakes and stared out at the lake and the stars. He'd go as far as I'd let him go. Of that I was sure. And I wanted to go far but not so far as to have him lose respect for me. I was amazed at how easily I could think about the situation from a woman's point of view.

A woman's point of view, I thought as I rubbed Mr. Edwards leg through his pants. Life looks good from here, I thought.

I felt soft and small in his embrace yet powerful as well. He's the one sitting behind the wheel in the driver's seat, but I'm the one in charge. I looked down at his lap and smiled without him seeing me. The shape of his growing penis was unmistakeable as it struggled against the fabric of his pants. I could touch it or I could ignore it. I felt him willing me with his mind to move my hand closer and so I did, teasingly close but still missing the target.

What does a 50 year old penis look like, I wondered? What would it feel like in my hand? How would it taste and what would it feel like penetrating my body?

These questions scared me and excited me. I was disgusted and turned on at the same time.

Will he think I'm a slut if I unzip his pants to take a look? Suddenly I felt damned if I did and damned if I didn't. I liked this man and I wanted to see him again but I was asking him to wait until my new body was ready. What if he met someone while I was gone or while I was recovering from surgery? Shouldn't I give him something to whet his appetite and keep me in the forefront of his mind?

The more I weighed the risk of doing something versus the risk of doing nothing the more stressed out I became. This isn't even our first date, I thought. Well technically it might be. After all, he did buy me a milkshake. Cheap date, I thought as I stared down at his pants.

I thought about some of the stories I'd read on the web about boys becoming girls. Not only did they become girls but they also became cock hungry bimbos. The former boys in the stories threw caution to the wind and absorbed sperm like an insatiable sponge. I'd beaten off to a few stories like that but had never thought they were anything more than poorly written fantasies.

So here I was in a story of my own making, but unlike a piece of fiction, the consequences of my actions would be real and lasting. If you really like him, you'll suck his dick, I thought. But if I really like him I'll do nothing of the sort because I want him to respect me.

To suck or not to suck. That is the question, I thought to myself. I half way thought about calling my mom to ask for her opinion. But I'm supposed to be a grown woman, I thought. Grown women don't ask their mothers such questions because they already know the answer. But I'm not a grown woman. I'm a boy and Mr. Edwards is a man.

"I'm sorry but I need a cigarette," I said. "Do you mind?" I asked as I reached for the floorboard and picked up my purse. "I don't want to smoke in your car, so I'll just go outside."

Mr. Edwards stopped me before I could open the door. "Its cold outside," he said. "I need a cigarette too. I'll roll down the windows a bit and we can smoke in the car."

Mr. Edwards started up the car and cracked both the windows before turning off the engine again. He lit my cigarette for me before taking the pack of Marlboros from his shirt pocket and joining me.

"I'm having a nice time," he said.

"Me too," I said as I slipped under his arm.

"Are you? he asked.

His question surprised me and I'm sure the confusion showed on my face. "You don't think I'm having a good time?" I asked.

Mr. Edwards sighed and said, "It just feels like we're on a date and I can't figure out why a woman like you would go out with a guy like me."

Ah hah, I thought to myself. Mr. Edwards has a problem with self-esteem. "A guy like you? You're not an axe murderer by chance. Are you?"

He laughed and said, "No, not really. I've always been more of a chain-saw kind of guy."

I knew he wasn't being serious but I raised an eyebrow all the same.

"Oh my God," he said. "You didn't think I was serious. Did you? I'd never hurt you. I don't even own a chain saw."

"Then that makes two of us," I said as I kissed him on the mouth. I could have drawn back but I lingered to see what would happen. Would he kiss me back?

I felt his mouth open and I closed my eyes to receive his tongue. It was wet, warm, and smoky. So this is what its like to French kiss a man, I thought as my thoughts faded into his kiss.

Like everything else in my life, the kiss was not simple or straight forward. It felt wonderful and made me feel wonderful but only because I blocked out how incredibly gross it was. He wasn't a girl and the day before he'd been my guidance counselor. But that was in the past. I was a woman now and that made everything okay.

Don't stop kissing me, I thought. Don't ever stop! I'm a woman. Watch me kiss. See me smoke. Hear me roar.

Mr. Edwards pulled away for a breath of air. He looked sick, as if he knew the truth. I flicked an ash out of the window and asked if I'd done something wrong.

"You? Something wrong? Of course not," Mr. Edwards said. "I just can't get it though my head that this is really happening. I'm not crazy and I don't want to scare you but its just that I feel like I've known you a longer than just tonight."

"That's okay," I said as I placed my hand directly on top of his penis. "I feel the same way, like we've known each other before."

His penis grew beneath his pants and filled the palm of my hand as he groaned. I placed my cigarette between my lips and let it hang as I undid his zipper and placed my hand inside.

I smoked hands free and smoke billowed from my nose as I pulled the flesh colored monster out of the hole in his pants. I can't imagine it looking very ladylike but I was a smoker and I wasn't ready to part with my unfinished cigarette.

Is this how a middle-aged woman behaves on a date, I wondered as I massaged his penis? Am I going too fast? Am I going too slow? Are there any rules or am I just making it up as I go along?

Whatever it was that I was doing wrong or doing right, Mr. Edwards seemed to be enjoying it. And why wouldn't he? I knew what I was doing. After all, I had a penis of my own that was begging for attention.

Mr. Edwards was obviously feeling good but how did I feel? The only way to describe how I felt was to say I felt psychotic and schizophrenic. Even people with multiple personality syndrome only experience one personality at a time. I felt like I was in a room with all my personalities and they were screaming at each other.

One of me says that I'm excited and turned on. Another of me screams that I'm a faggot. There I am asking myself if I'm being fair to Mr. Edwards. He doesn't know you're a boy. He thinks you're a woman. I feel like a woman! But you're boy screams the side of me that is cringing in the room full of mixed emotions.

Mr. Edwards looked as if he was in pain but I knew he wasn't. He was on the verge of spilling his sperm in my hand and he was trying to hold off. It hurts so good. Doesn't it, I thought?

I knew exactly how he felt. He was running from his orgasm, trying to make it last. You can run but you can't hide, Mr. Edwards. I'm going to make you cum in my hand. I'll see you throw your head back and groan as the orgasm overtakes you and it will be because of me.

I thought about going down on him as my hand moved up and down his shaft. It would be so easy, I thought. And hadn't I always wondered what sperm tastes like? That's gross, I thought. But really it isn't. Not if you're a woman and I am a woman, I thought as my hand raced up and down his big stiff penis. And then suddenly it was all academic.

Mr. Edwards starting grunting and groaning almost as if he was crying and my hand became warm and sticky. I looked down to see sperm erupting from his penis like hot lava from a volcano.

He uttered the words, "Oh my God," as his muscles went limp.

"Feel better?" I asked innocently. I still wasn't sure what to do with the sperm. A lot of it was in and on my hand and some had dripped down his shaft.

"That was unbelievable, Nancy," Mr. Edwards said. "But you didn't have to do that. Ooh your hand! I made a mess on you. Maybe I've got some napkins in the glove compartment. I'm so sorry."

"I don't want to drip on your pants," I said.

"Don't worry about my pants. I can always wash them and I will. The important thing is that we get cleaned up. As a matter of fact, you can wipe your hands on my pants if you want to."

"That's okay," I said as lifted my hand to my face and licked the sperm off them.

Time stood still.

What the fuck did I just do? Did I really just lick sperm off my hand? Oh my God! I did. That's so gross. Don't make a face. Whatever you do, don't make a face, I thought as I forced myself to smile.

Judging by the look on Mr. Edward's face, he was impressed. "I didn't mean for you to do that," he said.

"Its okay," I said as I bent down to lick the rest of him clean. Why not, I thought. I've already gone this far so I might as well see it through.

His pubic hair was rather gray, which didn't come us a surprise. The only reason I noticed is because I was looking for it. I cleaned his limp shaft with my tongue and tasted his sperm all over again. It actually took some effort to clean the sperm that had gotten tangled in his pubic hair. The coarse hair felt rough against my tongue.

The job was done and he was clean. I could have stopped there but I didn't. I covered his penis with my mouth and sucked. It was small and spent but that quickly changed.

Maybe this is a mistake, I thought as I opened my mouth to let his penis escape. I didn't want to get him all hot and bothered again, but I was surprised that a man of his age could get hard again so soon. I kissed the head of his penis and sat up in my seat.

"That was fun," I said. Fun, I thought. Had I just told him that was fun? It kind of was but what kind of a woman says something like that?

Mr. Edwards sighed and said, "That was so nice. You made me feel so good."

"Maybe I didn't want you to forget about me while I was gone," I said coyly. "I need a cigarette. Do you mind?" I asked as I opened my case.

"You're not the only one," Mr. Edwards said as he took out his pack of Marlboros. He lit my cigarette and asked if there was anything he could for me. "It doesn't seem fair that I should get all the fun," he said.

Well at least he used the word 'fun' too, I thought. "What makes you think it wasn't fun for me?" I asked. "I had a good time too," I said as I snuggled up against his shoulder.

****

It was a little past twelve when Mr. Edwards took me home. He walked me to the door and gave me a goodnight kiss. He asked me if we were still on for lunch tomorrow and I told him I was looking forward to it.

The living room was empty as I closed the front door behind me and hung up my coat in the closet, but I could hear someone, probably my mother, moving around in the kitchen.

Mom popped her head out from the kitchen as I was closing the closet door. "Did Ken come inside?" she asked.

The expression on Mom's face changed from cautious to giddy. "Did you have a good time?" she asked.

I nodded enthusiastically and told her I had a great time and then all of a sudden, without any warning, I broke down in tears.

Mom rushed to my side and grabbed me up in her arms. "What happened, Honey?" she asked. "Do you want to talk about it? There's some coffee in the kitchen.

I wiped at my tears and told her that I didn't know why I was crying.

Mom took me by the hand and led me to the kitchen. I sat down at the table and took my cigarettes out of my purse while Mom poured some coffee. Mom lit a cigarette for herself and asked me to tell her what happened.

"Did he kiss you?" she asked as she exhaled toward the ceiling.

"He did but I think I kissed him first. We were dancing when it happened," I said. "It wasn't much, just a peck, but that was how it started. But we stopped by the park on the way home and we kissed a lot, real kisses, the French kind with our tongues."

"So what did you think? Did you like kissing him?"

"At first I thought it was gross. He's a guy and I'm a guy and I'd never kissed a smoker before."

"But you're a smoker too. Isn't that just a little bit hypocritical on your part?"

"It doesn't bother me that he smokes. He doesn't even smoke that much. It just kind of surprised me at first, but that parts okay."

"So what was the part that bothered you?" Mom asked. "Did the two of you go farther than just kissing?"

"Yeah, I guess you could say that."

"Did you give Ken a blow job, Honey?"

"Not exactly, but kind of," I said. "I gave him a hand job and it got kind of messy but there weren't any napkins in the glove compartment."

"So you used your mouth to clean him?" Mom asked.

"Oh Mom!" I cried as my eyes filled with tears. I turned away because I couldn't bare for her to see my shame. "I put it in my mouth and I swallowed his sperm!"

Mom got up from the table and hugged me. "Its okay, Sweetie. It really is. You didn't do anything wrong."

"Then why doesn't it feel right," I wailed. "I feel like a fag. I put Mr. Edwards' dick in my mouth!"

"Did he force you to put his penis in your mouth?" Mom asked.

"No."

"Then you're saying it was your idea and you did it because you wanted to?"

"I don't know if I wanted to do it or I just wanted to see if I could do it."

"Then maybe it was a little bit of both," Mom reasoned. She kissed me on the cheek and returned to her chair. "Did you ever think about that?" she asked.

I shook my head in frustration. "Its just so weird Mom. Pardon my French but this whole thing is just so God damn fucking weird! Do you think maybe I might be crazy or something?"

"Dr. Girardi wouldn't let you do this if she thought you were crazy and neither would your father and I. But everyone would understand if you changed your mind. And even if you haven't changed your mind, there's no reason why you have to rush into this. I can call the airline and cancel the flight if you want to think about it for a while."

"Don't do that," I said. "I'm not going to change my mind. I just feel weird about it. Its hard to explain but being with Mr. Edwards tonight make it feel so real to me like it wasn't a game any more, not that I thought it was a game because I know its serious stuff."

"Its very serious stuff," Mom said. "Once you do this, there's no going back. You won't be a teenage boy anymore. For better or worse, you'll be a middle-aged woman like me and you'll be expected to live your life as such."

"I know that Mom and I promise you that its what I want. It just that doing that stuff with Mr. Edwards was so gay."

"I thought you liked men?"

"I do," I said.

"Then stopping thinking of yourself as a silly boy and start thinking of yourself as a mature woman and start acting like one."

"You're right," I said as I put out my cigarette and moved to light another one. I wiped my eyes and sat up straight in my chair.

"So what do you think about you and Ken?" Mom asked. "Do you think the two of you are getting serious?"

"I think so. I'm going to meet his family tomorrow after church."

"And you really like him?"

"I don't think I would have put his penis in my mouth if I didn't. I think I like him a lot."

"In that case you're going to have to get your head straight about sex. You didn't do anything wrong tonight. But that doesn't mean I wish you would have waited to be so intimate. Now that you've done it once, he's going to expect you to do it again. This is going to sound vulgar, but once a cock sucker always a cock sucker. You know that, right?"

"Yes," I said as I exhaled. "I guess that's one of the reasons it bothers me, because it sounds so nasty. You don't know what its like in a locker room. The things guys say."

"And you don't know the kinds of things women say when they're alone. Being a cock sucker isn't a bad thing in my world. As a matter of fact, its one of the most loving and intimate things a woman can do for a man. But from now on, lets just call it oral sex. I think that sounds a lot nicer."

I laughed and said, "Okay. Oral sex it is."

"Are you starting to feel better?" Mom asked.

I nodded and said that I was.

"In that case, you better get some sleep. You'll want to look fresh when you meet Ken's children."

Like Mother Like Son 14

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Dysphoria

Other Keywords: 

  • Mom TG

Permission: 

  • Posted by author(s)

Synopsis: Its the day before Darren and his mom go to Mexico. He sees Mr. Edwards for lunch and meets his children. Darren's little brother Sammy goes about his own problem of wanting to be female.

********************
Chapter 14
********************

Sunday morning found me sitting up in bed and having a cigarette as I thought about last night and the day in front of me. The night before I had put my mouth on Mr. Edwards' penis and today, after he went to church, I was going to see him and meet his children at lunch.

I found myself wondering how religious Mr. Edwards was. If he was a holy roller and over the top, the truth about me wouldn't sit well with him. After all, every one knows that God hates fags. Is that what I am, a fag?

I lifted the cigarette to my lips and sucked on the filter the way I had sucked on Mr. Edwards' penis. When I thought about it, well…it really hadn't been that bad, kind of like sucking on a big thumb. Except a big thumb a'int covered in goo.

I closed my eyes and tried hard to remember the names of his children and their ages. The oldest of course was Lars. That was easy to remember because he was my age and he was a big reason why any future with Mr. Edwards would be so crazy.

Not that Mr. Edwards had asked me to marry him. We were just going to lunch, but what if things progressed and we wound up getting serious? He'd expect me to be a mother to his children. How in the world could I be a mother to a boy who was my age?

I wondered if it would be any easier with his other kids. Ben is 13 and Abby is 11. 13 is pretty close to being a teenager, so Ben could be tough I reasoned. And then there is Abby. What did I know about raising little girls? It wasn't as if I'd ever been one before.

I put out my cigarette and chided myself for opening up such a big can of worms.

****

Mom came in as I was putting on my make-up. "You look nice," she said.

I thanked her as I put the cap back on the lipstick tube. "Nice enough to meet Ken's family?" I asked.

"They're going love you."

"I hope you're right," I said as I lit a cigarette. "I'm afraid this could blow up in my face."

"It could but it won't," Mom said. "I know you can do this because I saw you do it last night. You handled yourself like an adult woman. That's what Ken saw and that's what his children will see."

I stared into the mirror and admired the older woman looking back at me. She looked so mature and confident. If only I really felt that way.

"You're all dressed up," I said. "Are you going somewhere?"

"I'm taking Sammy shopping for a dress," she said. "That is if I can get him out of the house."

"Doesn't he want to go?"

"I thought he did, but now I think he's having second thoughts. Do you think you could talk to him after you finished getting dressed?"

*****

I thought about Sammy as I put the finishing touches on my make-up. I knew what he was going through or at least I thought I did. After all, it wasn't as if I was 100% sure of what I was doing. I was just making up the rules as I went a long.

I stood outside of Sammy's closed bedroom door and knocked.

"Who's there?" Sammy called.

"Its me," I said in my Darren voice. "Can I come in?"

Sammy agreed so I opened the door and walked inside. I found him sitting at his desk smoking a cigarette. A pack of Camel No. 9's was on his desk. His room was full of smoke.

"Maybe you should crack a window or something," I said as I took it upon myself to ventilate the room. Sammy nodded without saying anything as I opened his window.

The cold November air came rushing in as I sat down on his bed with my back to the window. I could have asked him how he was doing but by the looks of things I already knew it wasn't good. "Mom said you're not sure about going shopping with her. Do you want to talk about it?" I asked.

Sammy lifted his head and looked at me. The expression on his face said it all. He was scared and ashamed. I was well aquatinted with that look because I'd seen it on my own face from time to time.

"Mom said you met a man last night at the bar," Sammy said. "Do you like him?"

"I do kind of like him. As a matter of fact I'm going to see him again today, but this isn't about me. Lets talk about you."

"I'm just not sure if I really want to be a girl," Sammy said.

"Well if that's how you really feel then its okay with me, but last night you seemed pretty sure about it. What made you change your mind?"

Sammy shrugged and said, "Me and Dad were talking last night and he said some things that got me kind of thinking about it and I kind of think he's probably right."

"Right about what?" I asked.

"He thought maybe I wanted to be a girl because you're going to be a girl."

"But I thought you've been doing this for a long time," I said.

"Don't get mad but I was kind of lying about that. I thought Mom and Dad might like me better if I was a girl because they like you so much. They even think its cool that you smoke."

I nodded because I was beginning to understand. Jealousy is a big motivator. "Is that why you started smoking?" I asked. "Because I smoke?"

Sammy finished his cigarette and put it out in the ashtray. "I thought it would be cool to smoke like you and Mom," he said. "And I thought she'd let me do it if she thought I wanted to be a girl."

I understood exactly what he was saying even though it didn't make sense to me. But that's the thing about kids Sammy's age. Nothing they do makes sense.

"What about boys? Were you lying about liking them and thinking they're cute?" I asked.

"I don't know. I'm not sure. Its just that I don't think I like girls as much as my friends do and we used to be such good friends but now all they care about is girls."

"So you think that being a girl would make them like you more than they do now?" I asked.

Sammy picked up his pack of Camel 9's and shook his head yes. "Sounds stupid, doesn't it?" he asked.

I told him I wasn't in the position to think anyone is stupid. "I've done some crazy things for some really weird reasons," I said.

Sammy lit a cigarette and asked, "So what do you think I should do?"

"Well for starters, it sounds to me like you shouldn't go shopping with Mom today. You really don't want to be a girl. Do you?"

"Its not that I don't want to be a girl. Its more like I can't be because I'm not that way. I thought I could but now I don't."

"Look Sammy. The first thing you got to do is to stop thinking about it like its a bad thing. There's nothing wrong with being a boy, especially if you feel like one. Seriously! Being a boy is a good thing especially if you're already a boy."

"What about you?" Sammy asked. "Are you really a girl on the inside like Mom and Dad say?"

I took a deep breath and sighed. "Well to tell you the truth, I'm not exactly sure. But whatever it is, its between you and me and I don't need you telling mom and dad about it."

Sammy looked surprise. "But I thought you wanted to be a girl and that's why you were going to Mexico, you know to get the surgery to be like Mom."

"I do want to be like Mom and that's exactly why I'm going to Mexico. But I thought you were asking me if I really felt like a girl or if I felt like a boy."

Sammy's look of surprised turned into a look of confusion. "I'm not sure I understand," he said. "Why would you want to be a girl and do girl things if you didn't feel like one."

"I don't know. Why did you want to do it," I asked.

"Because you were doing it and it looked kind of fun. Do you think its fun to dress like a girl?" he asked.

"Are you kidding?" I asked. "I love wearing women's clothes. That's one of the best things about being a woman."

"What about the other stuff?" Sammy asked. "Do you like that stuff too? You know. Kissing guys."

"Well I've only kissed one guy but I did kind of like it. Actually, I liked it a lot."

"Mom said the guy you like is a lot older than you, like Dad's age."

"He is."

"Don't you think that's kind of weird and gross? Sammy asked.

"I guess it would be if he knew how old I really was."

"Or that you're really a boy," Sammy added.

"Yeah, but he doesn't know and he's never going find out, so to answer your question, No. I didn't think it was gross kissing him."

"Dad said he has kids and one of them is as old as you. You don't think that's weird either."

"I haven't met his kids yet so I don't know if its going to feel weird. But if they think I'm really older then they'll think I'm just a regular woman and there's nothing weird about that." I took a deep breath and sighed. "I don't know. Its kind of complicated and confusing but I'm sure I want to do this."

"So why do you have to be a woman?" Sammy asked. "If you got to be one person, why don't you just be a boy?"

"I would if I could because it would be a hell of a lot easier than doing what I'm doing now but I can't. As long as I'm a boy, there's always going to be a part of me that wants to be a woman like Mom. You gotta understand. This isn't something new. I've always felt like this for as long as I can remember."

"What about this?" Sammy asked. "What's going to happen after you get a sex change and everything? Do you think you're still going to want to a boy sometimes?"

I grinned and shook my head. "You know you're pretty smart for only being 11 years old."

Sammy exhaled a lung full of smoke and grinned proudly. "Well are you?" he asked.

"I don't think I'm going to ever really want to go back to being a boy, but I don't think I'll be able to keep from thinking about it. I guess what I think I'm trying to say is that I don't think I'll ever stop wondering about what my life could have been like as a boy. Sometimes I see guys my age and I'm glad I'm not doing the shit they're doing and then other times I kind of miss it."

"What about football? Do you miss that?"

I bit my lip and cocked my head. "Yeah, I guess I do."

"You were really good at it," Sammy said.

"Thanks, but you know I've thought about it and I pretty much decided that I'd rather be a woman than play football. I mean I'm always going to miss it and you know I'll think about the things that might have been, but what I'm trying to say is that being a woman is always going to be more important to me. So for me, I think I'm making the right choice. And that's the way you've got to think about it for you. The big thing is that you got to do what you think is right for you, the thing that will make you happy for the rest of your life."

Sammy nodded as he trimmed the ash from his cigarette against the side of the ashtray. "What if you think you're doing the right thing but it turns out you made a mistake?"

"Are you talking about me or are you talking about you?" I asked.

"You." Sammy said.

"Well, I don't think I'm making a mistake but if it turns out I'm wrong then I'm just going to have to live with it and make the best of it. After I get the surgery you know there's no going back. They're going to make me into a woman, an older woman like Mom."

"And that's what you really want?" Sammy asked.

"More than anything in the world," I said.

"Then its a good thing," Sammy said.

"I think it is, but what about you?" I asked. "What do you really want?"

"I want my friends to like me as much I like them," Sammy said.

"If that's the case then I'm pretty sure they'd like you better as a boy than as a girl," I said. "It's going to freak them out if they think you want to be a girl and like them the way girls like boys."

"Yeah, I guess you're right," Sammy said.

"I know I'm right. So what about the smoking?" I asked as I pointed at the cigarette in his hand. "I don't think your friends will think that's so cool."

Sammy nodded and wiped a tear from his eye. "I know that," he said, "and I tried to quit but I keep doing it."

"That's because you're addicted like me and Mom," I said. "But that doesn't mean you can't quit. Its hard but people do it."

"What happens if I can't quit?" Sammy asked.

"Then you'll keep smoking," I said. "But maybe you can switch to something less girly," I said as I pointed at his pretty pack of Camel 9's.

Sammy nodded thoughtfully.

"Well, its something to think about," I said as I stood up and rubbed the top of his head with my hand.

******

I arrived at Aldo's promptly at 12:30. Aldo's wasn't bad if you like Italian food, which I do, but I think the only reason they were still in business is because they're the only restaurant in town that still has a smoking section. I thought about that as I got out of the car and wondered if that was why Mr. Edwards suggested it. After all, Mr. Edwards didn't smoke in front of his kids, but his wife had. Perhaps they used to come here when she was alive. Or maybe he just wanted me to be comfortable. Either way, I was nervous and a cigarette or two would definitely take the edge off.

Mr. Edwards saw me before I saw him and waved me over to the table. He introduced me to his children, Lars, Ben, and Abby. Lars and Ben both stood up and took my hand as if they'd been coached to do so.

"Its nice to meet you Ms. Peterman," Lars said. "My dad has told us so much about you."

"Its nice to meet you too, but please call me, Nancy. That is if your father doesn't mind."

After being seated, I turned my attention to Abby and complimented her on her dress. The gesture on my part didn't come naturally, but I'd seen my mother use it a thousand times. Judging by the smile on her face, I'd done the right thing and quickly moved to make a similar remark about Ben.

"Are you sure you're only thirteen?" I asked. "You must be eating your Dad out of house and home."

Ben sat up proud and straight and assured me that he was indeed only thirteen.

Lars was a different matter all together and I knew I wouldn't win him over by patronizing him. I knew from experience that fifteen year old boys could sniff their way past the horse shit. "You look so much like your father," I said and then I went on to ask him about football, since I knew he played.

I interjected my knowledge of football as Lars told me about his season. He seemed impressed that I knew what I was talking about. I opened my purse and removed my cigarette case as Lars changed the subject to wrestling. Mr. Edwards did his gentlemanly duty by offering me a light and I thanked him as he handed me a menu.

I don't know a lot about wrestling. I had friends who were wrestlers and I knew they were always on diets, but other than that, I was pretty much clueless. Lars, on the other hand, was clearly passionate about the sport.

"I wrestle too," Ben spouted. "I won Big Kids State last year!" he said proudly. "Dad's my coach."

Mr. Edwards smiled at his son and told him the competition was going to be a lot tougher this season and if he wanted to do well, he'd need to start lifting weights like Lars.

I turned to Mr. Edwards and said, "I didn't know you coached wrestling." I asked him if he coached at the high school too, even though I knew he didn't.

Mr. Edwards shook his head no. "I'm just a club coach," he said. "Elementary and middle school kids. I coached Lars when he was younger too."

I looked across the table at Abby who seemed to be left out. "Don't tell me you wrestle too?" I asked.

Abby grinned and said, "Not any more, but I tried when I was 6."

"So you didn't like it?" I asked.

Abby made a yucky face. "It was sweaty and gross. I'm a cheerleader," she said proudly. She pointed to the cigarette in my hand and said, "My mommy used to smoke like you do."

"I'm sorry. I can put it out if its bothering you."

"That's okay. It doesn't bother me," Abby said. "I was just remembering my mom."

"I'm sure you all must miss her terribly," I said.

"We do, but she's in a better place," Ben said.

I felt awkward, as if I was intruding. Were they afraid I was there to take their mother's place. Before I could say anything, our waitress arrived and asked for our orders. I hadn't really had time to look at the menu but that didn't matter because Mr. Edwards ordered for the table. "Is spaghetti okay with everyone?" he asked. The children said yes and so did I. Mr. Edwards ordered a family style spaghetti with a large salad and an order of garlic bread.

Mr. Edwards looked at me as the waitress took up our menus. Unless I was mistaken, he was sensing the same kind of awkwardness about his late wife, but unlike me, he was prepared to face it.

"I suppose this is as good of a time as any," Mr. Edwards began, "but then again, maybe its not, because I haven't discussed any of this with Nancy. For all I know, she might not feel the same about me as I feel about her, but I want you kids to know that I like her. As a matter of fact, I like her a lot."

I covered his hand with mine and said, "I like you too, Jim, so it looks like the feeling is mutual."

Mr. Edwards breathed a sigh of relief. I guess he felt good about his and my feelings being on the same page. "In that case," he said, "it looks like the five of us are going to start spending a lot of time with each other. But I want you to know, that even though Nancy and I have feelings for each other, she's not here to replace your mother."

"Of course not," I added. "I wouldn't dream of such a thing. I've heard so much about her and I can't begin to imagine how special she really was, but I have a good idea. And I've heard so much about the three of you. You're all as wonderful as your father said you'd be. And as far as your father and I are concerned, well I think he's very special too, which is why I hope you'll share him with me."

That could have been it. The kids could have accepted what I said in silence and left me to wonder how they felt, or one of them or maybe all of them could have said something to let me know how I stood with them. It was Lars who spoke up to give us his blessing and the others followed suit.

"We just want our dad to be happy," Lars said. "You're all he's talked about since he met you. It's Nancy this and Nancy that. I'm sure our mom would want him to be happy too. And for what its worth, I like you and I think you're really neat."

"Me too," Ben said.

I thanked Ben and Lars and turned my attention to Abby. "What about you Abby? What to do you think? Is it okay if I date your daddy."

Abby's face broke out into a huge smile. "I'd like that a lot," she said, "and maybe we could do things together."

"Like shopping or going to lunch?" I asked.

Abby nodded her head. "Yeah, stuff like that," she said."

******

The kids had talked Mr. Edwards and I into taking them to play miniature golf after lunch. I love miniature golf but it was the first time I'd ever played it while wearing a skirt.

I was having a great time with Mr. Edwards and his children but my pleasure had more to do with being accepted as Mr. Edwards girlfriend than it did with how well I was playing.

Little Abby clung to me and wouldn't let me out of her sight as her brothers showed off for me. Mr. Edwards showed off too. Truth be told, I could have golfed better than any of them but I held back.

The course was crowded with a lot of families and several teens. Was this what it would be like to have a family of my own, I wondered? I hoped so, because I loved the way it felt.

I reached into my purse and pulled out my cigarette case when Abby let out a monstrous scream. Her scream was like a siren and her cheeks were wet with tears. Oh my God! Did I do something to her? Did I step on her foot?

My first inclination was to move away from her so that I wouldn't be blamed. But no! That's not right. A real woman would never do that, especially one who had a mother's instinct. But I didn't have a mother's instinct. I was just pretending to be motherly and womanly.

Mr. Edwards was twenty or so odd feet away and I was right next to her. Why was she screaming, "Mommy!" Oh my God, what am I supposed to do? I felt her small hands dig into my hips. Did she feel the padding or did it feel natural to her? Why am I thinking about that? I have to do something. I need to do something.

I dropped my cigarette case and the golf club to the ground and took a knee beside her. I placed one hand on her shoulder and wiped her tears with the other. "What's wrong, Honey? Are you hurt?" I asked.

Abby sat down hard on the ground and rubbed her leg. "It burns!" she screamed.

I moved her hand away and saw a round red welt. "Did something bite you?" I asked.

Mr. Edwards bent down beside me and the boys gathered around us, while some of the other golfers turned their attention toward us.

"Something stung me!" Abby wailed. "I think it was a wasp. It hurts so bad. Make it stop hurting. Pleaseeee!"

Now that I knew what was wrong, I didn't even have to think about it. I did what my mother had done for me in similar situations. I picked up my cigarette case off the ground and extracted a cigarette. I tore it open so that the tobacco spilled into my palm. I then spit on it to make it wet.

"This will suck out the poison," I said as pressed the wet tobacco to the sting. "How does that feel?" I asked. "Better?"

Abby sniffed and nodded her head. "Its like magic," she said. "It doesn't hurt any more."

I held my hand in place for about a minute, giving the tobacco time to pull out the poison. I moved my hand away and saw the stinger protruding from her skin and removed it with my long painted nails.

"There we go. All done," I said as I held the stinger out for her to see.

"Thanks Nancy! You're the best," she said as she reached out and hugged me.

I returned her hug and rocked her back and forth. She felt good in my arms because she made me feel like a mother."

Mr. Edwards helped us to our feet and asked Abby if she still wanted to play. She assured him that she did and asked if it was her turn yet.

*****

I could have spent the rest of the day and all night with Mr. Edwards and his family but I needed to go home and pack. Tomorrow was the big day. We were flying down to Mexico.

I'd wound up telling Mr. Edwards a small version of the truth about my trip to Mexico. I told him that I was getting some cosmetic surgery, which included breast augmentation. He tried to tell me that I didn't need such things but I argued that he'd never seen me with my clothes off and he never would until I was comfortable with my body. That was all the incentive he needed. "Hurry up and feel good," he said.

*****

I found Sammy with my parents when I got home from seeing Mr. Edwards. I Hadn't forgotten about Sammy's dilemma and neither had my parents. They were concerned about him and so was I, but to a lesser degree.

I don't know why my parents felt that I should be an expert on Sammy's problem with sexuality, but that's what they thought. If you asked me, its like asking a 5th generation dude named Sanchez to be fluent in Spanish.

I did my best to assure them that Sammy did indeed know what he wanted.

"So you don't think he's just embarrassed about wanting to be a girl?" my mother asked.

I told her that Sammy didn't want to be a girl. He was just jealous and looking for attention. "But don't be mad at him," I said. "Its not like he was playing with your emotions on purpose. He's just a kid."

Mom smiled softly and admitted that she was relieved. "As much as I'd love to have a little girl, I don't want to lose both of my sons," she said.

I reminded her that she wasn't losing a son as much as she was gaining a sister.

Mom nodded and lit a cigarette. "You know its not too late to change your mind if you're having second thoughts about this."

"No second thoughts and no regrets," I said as I removed a cigarette from my case and proudly fired it up. My penis tingled as I thought about the loose and wrinkled skin I'd be coming home with. Not to mention the boobs and the hips.

I took a puff from my cigarette and held it in my lungs before letting the smoke escape past my pursed lips. "I'm going to be a woman, Mom. I'm going to be just like you."

"And you're sure that's what you really want?" she asked.

"You know it is. Do you really have to ask?"

Mom smiled and shook her head. "Just checking," she said.

Like Mother Like Son 15

Author: 

  • Sharon Parsons

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Fiction
  • Novel Chapter

Genre: 

  • Transitioning
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Voluntary

TG Elements: 

  • Smoking Fetish

Permission: 

  • Posted by author(s)

Synopsis: Darren and his mother travel to Mexico so that Darren can get the cosmetic surgery he needs to look like a middle aged woman.

*****************
Chapter 15
*****************

I sat down on one of the the hotel's double beds and lit a cigarette. The five hour flight to Mexico had been grueling. My discomfort had nothing to do with bad weather or turbulence and everything to do with nicotine withdrawal.

Mom lit a cigarette and took a seat on the couch across from me. "Welcome to Mexico," she said.

Instead of answering her, I stared at the rings of smoke circling from the end of my cigarette.

"Is everything okay," my mother asked?

I bit my lip and wiped away at a tear that had come out of nowhere.

Mom got up off the couch and sat next to me on the bed. She put her arm around me and I bent my head so that it was resting it in the crook of her neck.

"You don't have to go through with this," she said. "We can fly back home tonight and pretend none of this ever happened. You can have your old life back."

I sniffed and told her that I wasn't crying because I wanted my old life back.

"Then what is it? What's wrong," she asked?

"Its just that its so real now," I said. "Everything I always wanted or thought I wanted…its all about to happen."

"Then why aren't you happy?"

"I am happy, but…"

"But what?" asked Mom. "If you're having second thoughts about this then we should talk about it now, before its too late."

"Its not like that, Mom. Its more like this is just a dream and its not really happening. I keep thinking I'm going to wake up any minute and none of this is going to real."

"Its not a dream, Darren. This is really happening. And if you go through with this surgery, you'll have the body of a middle aged woman. And more importantly, you'll have the life of a middle aged woman."

"And when I come back after Christmas, they'll cut off my penis and give me a vagina?"

"That's the plan," my mother said. "But you can wait until later if you're not sure."

"But that's thing, Mom. I am sure. I'm scared to death but I've never been more sure of anything in my whole life. The sooner I'm like you, the happier I'll be. I'd do it tomorrow if it was okay with the doctor."

"I don't know, Honey. With everything else you're having done, it would be such a physical strain to do everything at once. We'd have to stay another two weeks for you to recover, and with Christmas coming up, you don't need to be feeling like a tank ran over your body."

I was totally floored. "Are you saying its a choice and I don't have to wait to get it all done?"

Mom blinked and shook her head. "Dr. Girardi doesn't think its a good idea for you to get everything done at once, and neither do your father and I."

"Why? If its just the physical pain, then I can take it. I'm tough, Mom. You know that."

"I do know that, Honey. "But we're not as worried about your body as we are about your mental health. It's just so much so soon. Don't you think?"

"Are you kidding me?" I asked as I shook my head violently. "This can't happen fast enough for me. Why didn't you tell me I could do it all at once?"

Mom hesitated and took a puff from her cigarette. "I guess I was just trying to give you enough time to be able to change your mind."

"Because you want me to change my mind?" I asked.

"No. Of course not, and quit saying that. None of this is about what I want. Its about what you want. But I don't want you to have any regrets either." Karen sighed and said, "I'm sorry for sounding like a broken record about the regrets, but a sex change will change your life for better or worse. There's just no way around that and I don't want it be for the worst."

"This is really hard for you," I said as I placed my hand on top of hers, "Isn't it?"

The expression on her face turned blank as she nodded her head. "I keep thinking I must be the worst parent in the world for letting you do this," she said. "Its bad enough that I gave you permission to start smoking. Look at you. You're smoking three packs a day and you're only 16."

"You say it like its a bad thing, but its not."

"But it is a bad thing!"

"Not if I want to be like you and I do. That's why I want to do everything while we're here. The next time we get on a plane to go home, I want to be a complete woman like you. I want the skin and the hips and the boobs with all the wrinkles and the sags in the right place, but none of that is going to be good enough if I still have a penis."

Mom's sense of humor seemed to come back to her. She squeezed my hand and laughed. "Its okay, Honey. You can say it and I won't be offended. You want a pussy, don't you?"

I gasped because I didn't expect her to use that word. My mom was always so proper. "Well actually, I was going to say vagina."

"I know you were, but you were thinking about it as a pussy, and there's nothing wrong with that. I call it a pussy too when I'm with the girls, and so should you. So lets try it again. Why do you want to get a sex change while we're here."

I laughed out of nervousness because I was embarrassed.

"If you can't say it out loud then it means you don't really want it."

"But I do want it Mom."

"Then let me hear you say it."

I took a puff from my cigarette and allowed the smoke to settle in my lungs before blowing it out. "Ok, I'll say it. I want a pussy, Mom. I want a real honest-to-god pussy, just like yours."

"Tell me why you want a pussy."

"So I'll be just like you. I'll look like you and I'll smoke like you and I'll…"

"You'll do what like me? Say it."

"I want to have a pussy so I'll be able to know what it like to have sex the way you and Dad do it."

Mom squeezed my hand and said, "See? That wasn't so bad. Was it?"

I took a deep breath and sighed.

Mom laughed and said as I was as red as beet. "Please don't be embarrassed. I'm glad you want to experience sex with a man as a woman. It makes me feel much better about saying yes to this."

"Are you saying I can get the sex change while we're here?"

Mom kissed me on the cheek and said, "No. I didn't say that but we can talk about it over dinner. Aren't you hungry. I'm starved."

*****

One of the neat things about Mexico is that you can smoke everywhere and almost everyone smokes. Another neat thing about Mexico is that they have real Mexican food, not like the frozen stuff they serve back home.

We had just sat down at our table when the large family beside us were finishing their meal. They appeared to be a husband and a wife with their two children, a young boy and a young girl. The boy looked to be 13 or 14, a couple years older than his sister. An older couple, which was probably the grandparents, sat at the table too. I watched the adults as they lit cigarettes while the waitress poured coffee.

I don't speak Spanish, but I heard the older woman ask the younger woman a question and the younger woman nodded her approval. I watched as the grandmother offered her cigarette case to the children. The boy declined but his younger sister blushed as she removed a long white cigarette from the case.

The girl's parents watched proudly as the older man lit the young girl's cigarette. Grandma beamed as her grand daughter filled her young lungs with smoke and then emptied them into the air above the table.

The site unfolding in front of me would have caused uproar had it occurred back home, but here it seemed natural and innocent. The little girl, who couldn't have been older than 9 or 10, was an accomplished smoker, who looked very much at ease with her habit.

Mom, who had been watching it too, lit a cigarette for herself and said, "I never would have given you permission to smoke when you were that young."

"I would have given anything if you had," I said as I removed a Virginia Slim from my leather case and lit it. I looked at the little girl again and said, "Seeing her smoke like that makes Sammy seem not so young. Doesn't it?"

Mom shrugged and said she was still crossing her fingers that Sammy would come to his senses and quit. "Its funny," she said. "He looks up to you the way you look up to me."

"Yeah, but I know in his heart, he wants to be a boy, and he doesn't want to smoke either. He just got confused. That's all." I might have said more about Sammy, but we were interrupted by an English speaking waitress who helped us order from the menu. Mom decided on chicken and I went with something that sounded like a beef burrito. We both asked for a beer.

Our conversation about Sammy followed the waitress with our order and Mom asked me about Mr. Edwards. "So what do you think about Ken? Have you given any thought to letting him test drive your new pussy when you get it?"

"Only every other minute or so," I said as I exhaled a cloud of smoke toward the ceiling. "I just hope I can make him feel good."

"I wouldn't worry too much about making Ken feel good. Men always feel good when they're fucking something, but why am I telling you this? I bet you've fucked a lot of girls, haven't you?"

I nodded reluctantly.

"Then you know the man always feels good," Mom said. "I'm more worried about the way you'll feel when Ken fucks you. I know how vulgar this sounds but its something you need to think about and you've got to prepare yourself for the possibility of living the rest of your life without having orgasms."

"Do you have orgasm when you and Dad are having sex?"

Mom grinned wickedly and laughed. "Every time, Sweetie. Your father is a wonderful lover. You'll be a lucky woman if Ken is half the man in bed that your father is. And just so you know, size is important."

I thought about the night in Ken's car when I gave him a hand job. "Ken is pretty big, I said.

"Then that's good," Mom said, "but you're not going to satisfy him forever with hand jobs. If he's a real man, he's going to need more from you and your new pussy won't be fully operational for at least a couple months. Do you think you'll be up to giving him a blow job when the time comes?"

"I think so. I mean I thought about it that night in his car, but I was afraid he'd think I was a slut."

Mom laughed and reminded me I wasn't in high school any more. "He thinks you're a grown woman and grown women are supposed to give their boyfriends blow jobs, and another thing, they swallow afterwards. I hope you're not disgusted by the idea of Ken cuming in your mouth."

I told her about licking Ken's sperm off my fingers when he had cum on hand.

"That's good," Mom said. "Did you like the way it tasted?"

I blushed and told her that it had tasted "interesting". "But not nearly as bad as I thought it would be," I added.

"That's good, Honey. I was afraid you might have changed your mind once the excitement wore off. And I guess that's the word I've been looking for all this time, 'excitement'. I know that sometimes when I'm excited about doing something, I couldn't be happier, and its the best thing in the world."

"Kind of like new car buyer's remorse?" I asked.

Mom grinned and shook her head. "Exactly like that," she said. "But what would you know about buying a new car?"

"Nothing really. I just see and hear it with other people. But I get why you're comparing a sex change surgery to it. But its not going to be that way with me because I'm never going to get tired of being a woman, especially a middle-aged woman. I know you probably don't believe me, but I don't think there's any way the excitement could ever wear off."

"Its not that I don't believe you. Its more like I don't understand you. I'd give anything to be your age again, yet you want to be old like me. I'd give anything to have never smoked my first cigarette, yet you're thrilled to be smoking three packs a day. And its not that I don't enjoy being a female, but I'll never understand why you'd give up your manhood to be a woman."

"But you accept that I really do feel the way I do and that it's important to me, right?"

"Absolutely, Honey! I wouldn't have let this go as far as it has if I didn't believe it was important to you."

"And you're happy for me?"

Mom nodded and said, "I'm happy when you're happy and I can see you're very happy."

I laughed and said, "I'll be happier when I get a pussy and a pair of boobs."

Mom didn't laugh and her expression turned serious.

"What's wrong?" I asked. "Did I say something that bothered you?"

"No. Its nothing like that. I was just thinking that even though you're dressed as a woman, you're still a man underneath the clothes, and this could very well be your last night as a man."

"So what?"

"So…I was just wondering if you'd like to do something special for your last night as a man?"

"I see," I said as I nodded my head. "Kind of like a last meal for a condemned prisoner?"

"Yes, something like that."

I didn't answer her right away because I was thinking about what she had said. My mom was asking if I'd like to have sex one last time as a man. It was a good question and a fair question because it wasn't as if I didn't enjoy fucking girls, although lately I'd spent a lot of time wondering what it would be like to be fucked by a man- an older man.

"Well? What are you thinking," Mom asked?

I bit my lip and said, "Well for starters, I'm thinking that I didn't bring any man clothes."

"What else are you thinking?"

"I don't know. It depends a lot on what you're thinking," I said.

"I'm thinking that you're thinking that maybe I could be your last time and that would be incest, Honey?"

"Then lets not call it that," I said.

"It wouldn't matter what we called it. The thing is that we'd both know what it really is and I don't think we could live with it."

"We could try."

Mom closed her eyes and sighed. "The last thing I want to do is to hurt your feelings, but I have to be honest with you. I know you're still my son and I love you but its getting harder and harder for me to think of you as a man. If we made love, it would be more than incest to me. It would be like making love to another woman and I just can't go there. I'm not a lesbian."

"Then why did you ask if there was something I wanted to do?"

"I was thinking you might want to spend your last night with a prostitute."

"I see."

"Don't be mad at me, Sweetheart."

"I'm not mad. I'm just a little disappointed, I guess."

"So what do you think about spending your last night with a prostitute? Would you like to do that?"

"I don't think so, Mom. If I can't make love to you then I don't want to have sex with another woman. What if we just slept together in the same bed tonight without having sex? Do you think we could do that?"

Mom smiled warmly and said she thought that would be very nice.

******

When we got back to our hotel room, Mom and I took off our make-up and got dressed for bed. I wore the long chiffon colored silk gown that used to belong to my mother. It had always been my favorite choice back when I was "borrowing" her clothes. I had taken off my make-up but I was still wearing my wig and breast forms.

Mom came out of the bathroom holding her leather cigarette case and wearing a pink silk teddy without a bottom. She blushed when she saw me gawking at her naked pussy.

"Don't stare," she said. "You're making me uncomfortable."

"I thought you said we couldn't have sex."

"We're not. I just thought you'd like a preview of what you're going to get tomorrow. I can put on a pair of panties if it bothers you."

"No. Don't do that. You're right. I do want to see."

Mom slid into the bed beside me and kissed me on the cheek. She told me that she loved me.

"I love you too, Mom."

"I know you do," she said. "You love me so much that you want to be just like me. Don't you?"

"I do, Mom. I want to be just like you. I always have."

Mom took my hand and placed it on her soft pillow-like breasts. "Tomorrow you're going to get breasts like mine? Is that what you want, Honey?"

"Yes," I croaked.

She moved my hand so that my fingers were touching her cheek. "Feel my skin. Its soft and wrinkled with age. Is that what you want, Honey? Do you want wrinkled skin like your mommy?"

I closed my eyes and whimpered. "Yes, Mom. That's what I want."

She moved my hand down her chest and laid it to rest on her paunchy stomach. "Feel my middle aged paunchy stomach, Honey. Do you want your belly to look like mine?"

"Yes, Mom. I do."

She slid my hand until it rested on her wide hips. "Do you like my big wide child bearing hips?" she asked.

"Yes. Yes, I do."

"Do you want big wide hips like mine?" she asked.

'Yes," I said as tears rolled down my cheeks.

She moved my hand across her thigh until it stopped above her vagina. "Feel my hairy pussy, Honey. Does Mommy's little boy want a big hairy pussy like his mommy's?"

"Oh yes. Most definitely," I said.

"That's good," she said, "because your new boyfriend is going to want to fuck it with his big cock. You know that don't you?"

"UhHuh, yeah."

"And that's okay with you?" she asked. "Do you want Mr. Edwards to fuck your new pussy the way your daddy fucks my pussy?"

"All the time," I said.

"Is that what you're imagining right now?" she purred, as she touched the tip of my erect penis with her finger.

I couldn't breath and I felt as if I was going to suffocate under the weight of my anticipation. I mentally coaxed her to take my penis in her hand but she withdrew it . "Why did you stop?" I asked.

"Because I'm your mother," she said as she reached for her leather cigarette case. She lit a cigarette and exhaled away from my face. "I know you need an orgasm but I'm not going to give it to you. If you want one, and I'm sure you do, you'll have to work for it yourself."

"You mean…"

"Do it yourself," she said.

"But I can't jack-off in front of you."

"Why not?"

"I don't know. I just can't. It wouldn't be right."

"Because I'm your mother?"

"Well yeah."

"And that's why it wouldn't be right for me to do it to you either."

"I don't get it. So what are you saying? That we should forget all this and just go to sleep."

Mom laughed and shook her head. "Are you going to tell me you're willing to waste this opportunity by just going to sleep? I may not be a boy, but I have a good idea about the things going on in your head. Don't tell me you haven't dreamed of something like this happening. Look at you. Your dressed like a woman in front of me and I'm giving you a chance to masturbate. Don't tell me this doesn't turn you on."

I watched as she brought the cigarette to her lips and took a puff. God, she looked so sexy and powerful. And she was right about my fantasizing about something like this happening. My mom was giving me the opportunity to jack-off in front of her while dressed as a woman.

Why the hell did she have to be so mean about it, or was it just me? I felt as if she were torturing me. She'd say one thing and then she'd say another thing. And this was one of those times. I wondered if maybe she was schizophrenic or something.

My penis fell limp and I quickly moved to cover it with my nightgown but not before my mother saw it and snickered.

"Maybe you'll get hard again if you have a cigarette in front of me," she offered. "Besides its been almost ten minutes since your last smoke. I bet your body is dying for one. Isn't it? How does it feel to be an addict like me, Sweetie? Come on, Honey. Fire one up for Mommy." She laughed and said, "Don't you want to smoke like a woman in front of Mommy?"

I told her that I hated her has I reached for my cigarette case.

"No you don't. You love me. That's why you want to be like me. Isn't it?"

I lit a cigarette without giving her an answer.

Mom grunted as my penis poked up against my nightgown. "Looks like someone is excited," she said. "I bet you get hard every time Ken lights your cigarette. Don't you?"

She was right. I couldn't help but get sexually stimulated whenever I smoked a cigarette while dressed as a woman, which was all the time now. And I got especially hard whenever a man lit my cigarette for me.

"What's wrong with you? Why are you doing this to me?" I asked.

The expression on her face changed from vicious to amused. "I'm just having a little fun and playing with you. Don't take it personally."

"Don't take it personally? You're making me feel like I'm some kind of pervert. How can I not take it personally?"

Her expression changed from amused to sympathetic and then to apologetic. "I'm sorry, Honey. I know I'm being awful. I don't know what comes over me when I do these things to you. Its like I'm some kind of monster"

"Then why do you do them?" I asked.

"Because I'm sick, Honey. I'm sick like you but its a different kind of sickness. I tried to tell you about it before, but I don't know if it made any sense. It hardly makes sense to me so there's reason for me to expect you to understand."

I asked her if it made her happy to hurt my feelings and make me feel bad about myself.

"Of course not. No! I hate myself for saying the things I do, but Oh God, this is going to sound so awful." She paused to take a puff from her cigarette. "The only way to explain it is to say there's some sick part of me that gets turned on by feminizing and sissifying you."

She grabbed my free hand and pulled it to her crotch. "Feel how wet I am? Seeing you turn into a middle aged woman and shaming you about it turns me on. Is that sick or what? It's like I'm two different people. One of me is a mother who loves you more than you'll ever know, and the other part of me is a sexually perverted monster."

I heard everything she said and I absorbed it but I was also absorbing the wetness of her pussy.

"Is that why you told me I could get the sex change surgery tomorrow?" I asked.

Mom sniffed and wiped a tear from her eye while she nodded. "As your mother," I think you should wait until you know for sure if you're ready to do it. But as a monster, I can't wait for that doctor to make a pussy out of your cock. I'm so sorry, Honey. Can you ever forgive me?"

I put out my cigarette and turned to face her on my side. I slipped my arm under her shoulders and between her pillow so that I was hugging her against my body. "It's okay," I told her. "I don't blame you. I just needed to understand why you're doing these things to me. I know you can't help it but I get so confused when you do it, because you're right. Its not like you."

"I'm a bad mother," she said as she cried against my shoulder.

I took the cigarette from her fingers and put it out in her ashtray. "No. You're not a bad mother," I said. "You're a great mom and that's one of the reasons I want to be like you."

"But a good mother would have never let you do any of this, the smoking, the dressing up. the sex change stuff. I'm a monster and you should hate me for it."

"Quit talking like that, Mom. You're not a monster. You're a good mother with some mixed up feelings about this and sometimes it gets to you. I'm the same way. I really do want to be a woman and I know it will make me happy. But it turns me on too, especially the smoking and being older. So what I'm saying is that we're both kind of weird and sick in a way but it doesn't make us bad people. It just makes us human."

Mom kissed me on the cheek and told me she loved me.

I told her that I loved her too.

"And you're still sure about doing all this, about becoming an older woman?" she asked.

"I'm sure about everything, Mom. And I want to ask the doctor if he'll go ahead and do the sex change surgery while we're here."

"I think you're very brave for doing this," she said.

"Well I don't feel brave. I feel scared to death."

"I know I've been acting crazy and there's no reason for you to trust anything I say, but I think you're doing the right thing."

"You do? Honestly?"

Mom nodded her head and kissed me on the cheek. "Yes I do," she said. "I realize you're reasons for wanting to become a woman aren't exactly noble or shall we say, "text book".

"Because I'm really just a cross dresser with a smoking fetish?"

"That's right, but its also okay," she said as she sat up in bed and lit a cigarette. "Want one?"

"Yeah, I guess I do," I said as I propped myself up against my pillow and lit a cigarette of my own.

"As I was saying, being a crossdresser and having a smoking fetish isn't going to make you any less of a woman. Especially in your case because if anything, those things make you feel more womanly and I just can't see anything wrong with that, and neither can Dr. Girardi."

"Thanks Mom. That really means a lot to me. Seriously, it does."

"Well, I wasn't saying those things to make you feel better about your self. I said them because they're true and I want you to know that I really think you're doing the right thing. And that's me you're mother saying it and not the monster that lives inside me."

"Really?" I asked.

"Yes, Really," said my mom as she took my hand in hers. "Cross my heart and hope to die." She took a puff from her cigarette and said, "The really amazing thing about all of this is how fast you've grown up and how mature you've become. It wasn't that long ago that you were tackling kids on the football field and doing homework. And now you're smoking and drinking and thinking about having sex with a man who is as old as you're father, and you're on the verge of becoming a mother to a teenage boy."

I shot her a quizzical look.

She laughed and said, "Okay, that part was the monster in me talking but you have to admit it does sound sexy and fun and doesn't it?"

"Yeah, Mom. You're right. It sounds like a lot of fun."

"Good. Now lets finish our cigarettes and get some sleep. You've got a big day in front of you tomorrow.

Like Mother Like Son 16

Author: 

  • Sharon Parsons

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

TG Themes: 

  • Stuck

TG Elements: 

  • Breasts / Breast Implants
  • Surgery

Permission: 

  • Posted by author(s)

*************************
Chapter 16
*************************

Synopsis: 16 year old Darren, aka Nancy, and his mom travel to Mexico to see some nice doctors. This is the final chapter of Like Mother Like Son.

Mom was still asleep when I woke up, so I tried to be quiet as I got out of bed. I thought about the things she'd said the night before about being a monster. She was my mother and I loved her dearly, but she was right about being a monster. I thought about her as I picked my cigarette case and lighter off the nightstand and made my way to the bathroom.

I stood in front of the bathroom mirror and lit a Virginia Slim. It would have been an understatement to say I looked stupid. A 16 year old boy, in a night gown with falsies underneath, stared back at me with a woman's cigarette dangling from his lips.

The sight of me smoking in my mother's favorite nightgown would have turned me on a couple weeks ago, but not this morning. I was disgusted by what I saw. "You faggot," I whispered to my reflection. "Just look at you. You make me sick."

I don't know where the reaction came from. It could have been been because I didn't have my wig and make-up on. And then again, it could have been because of the way my mother had made me feel the night before.

With my cigarette clenched between my teeth, I hiked the hem of my nightgown and drained my bladder while standing. So ladylike, I thought to myself. And oh so temporary. I'd made up mind to ask the doctor to do the sex change surgery while we were down here. After that, standing while peeing wouldn't be an option. I cupped my balls in my hand and said goodbye to them.

Mom woke up when I flushed the toilet.

"Morning, Nancy!" she called from the bed.

"Morning to you too, Mom," I said as I dried the urine from my penis head with a piece of toilet paper. I hate it when silk gets water stained and urine is even worse than water.

Mom asked if I wanted a cup of coffee before I took a shower and I agreed that coffee would be nice. She was brewing it in the small two cup coffee maker when I came out of the bathroom.

"It shouldn't take too long for the coffee," Mom said as she lit a cigarette. She moved the ashtray from her nightstand to the small table next to the heater and took a seat. "So did you get any sleep last night?" she asked.

"Enough," I said as I sat down in the chair across from her.

"I'm sorry that I let things get out of hand last night," she said as she trimmed the ash of her cigarette. "I was just so stressed about today and I let it get to me. I'm sure you must think I'm horrible."

"I don't think you're horrible, but it did kind of catch me by surprise. I know you've said some weird things to me before, but last night was really weird. If you know what I mean."

Mom exhaled a cloud of smoke toward the ceiling and shook her head. And then she laughed and said the worst part was that she couldn't even blame it on drinking too much. "It wasn't like the beer went to my head. It was more like my brain threw up everything bad and awful." She looked at me and said, "I know I can't take back the things I said, but I do want to make sure you know how much I really love you and it doesn't matter what sex you are or how old you are. You'll always be my baby and I'll love you until the day I die and then some."

Seeing that the coffee was ready, I got up and poured us each a cup. "I know what you're saying and I know that you love me. And I want you to know its okay. I was thinking about it this morning before you woke up and I know why you said those things."

"You do?" Mom asked.

"I think about it the same way sometimes, so if you're sick then I'm sick."

"You're not sick," Mom said adamantly. "You're a wonderful human being and you're going to be a terrific woman. I'm already so proud of you that I don't know where to begin."

"No, its not like that and you know it, and I know it and Dr. Girardi knows it. I'm a pervert and a sexual deviant and I'm letting this stuff run my life. So don't act like its not true, and anyway, you're no better either. You said so you're self. We're both sick."

"Then what are we doing here, Sweetheart? It's not too late to put a stop to this. We can check out of our room and take a cab to the airport right now. We can make it home in time for dinner."

I shook my head and stubbed my cigarette out in the ashtray. "You know I can't do that, Mom, because you know I need to do this. I need to be a woman- an older woman like you."

"I know you do, Honey. But you don't have to do it today, do you?"

"Are you kidding? Do you have any idea how long I've wished for this to happen? You might be sick and weird but I love you and I've wanted to be just like you for as long as I can remember. This day was never supposed to happen, not because I didn't want it to happen, but because I thought it was impossible. But here we are in Mexico. I'm going to be a woman, Mom, with a body just like yours and a life just like yours. Everything you said about me is true, but like you said, it doesn't make me a bad person and it doesn't make me wrong for doing this. Its the right thing to do, at least it is for me. There's no way I could ever live with myself if I let this chance get away from me. I might not need to be a woman but I want it more than anything in the world. I really want to be a woman, Mom."

Mom sighed and smiled. "I'm so excited for you," she said.

*******

Dr. Carlos Rivera had a pleasant look about him. If I hadn't known he was a doctor, I might have thought he was a bull fighter. He just had that kind of swagger about him.

Dr. Rivera was a cosmetic surgeon and judging by the rings on his fingers, he did quite well at it. The man who would be doing my SRS surgery was Dr. Wang. He had a first name but I couldn't pronounce it. As you can probably tell by his name, Dr. Wang wasn't Mexican. He was Taiwanese or maybe Korean. I really wasn't sure. But he did speak Spanish, and that was a good thing because I don't speak any other language except for English.

An overweight balding man, who called himself Santos Ortega, was our interpreter. I suppose he was able enough, but his thick accent made me wish we had an interpreter for our interpreter.

It was actually kind of cool. With the five of us in the room, it felt like I was working with a team. Being the center of attention made me feel important. On the other hand, I felt kind of awkward because these guys had an air of machoness about them that came straight out of a beer commercial.

I remember when I was macho. But I didn't call it that. I called it studly. I wasn't feeling very studly in my high heels and skirt though. And my bouncing breast forms weren't much help in that department either. That was probably good thing though. After all, even though I knew they were in it for the money, I didn't want to give them a reason to delay the surgery.

I did my best to appear confident and assertive but in a feminine way. I didn't pound my breast forms when I talked and I never raised my voice.

I liked that they addressed me as Senorita Peterman, although I knew they were probably laughing on the inside every time they said my name. Oh, the mocking, but at least it was silent and respectful.

Oddly enough, the whole event was business as usual. Neither doctor seemed concerned or worried. They were just there to trade services for dollars.

Dr. Wang was the first to poke and prod me, although it was more like squeezing and fondling. He said something to Santos who relayed it to Mom and I in English.

"Dr. Wang needs for you to take off your skirt and panties so that he can examine you." He then asked if I'd be more comfortable if my mother left the room. He said she could come back after Dr. Wang was finished. I told him it was okay and that I wanted my mother to stay.

So there I was, standing in the middle of the room with my skirt and panties on the floor while Dr. Wang played with my testicles. Embarrassing? Yeah, I guess you could say that. It also tickled and kind of felt good.

All of a sudden, my mom broke into laughter and everyone turned to face her.

"I'm sorry," she said. "I was just thinking to myself, Dr. Wang is playing with Nancy's wang."

I caught my mother's joke and didn't appreciate it. The other three men just looked puzzled and Dr. Wang went back to his examination. Once he was done, he said something to Santos, who told me I could put my clothes back on.

"Dr. Wang says he can do the surgery. You will be a woman," Santos said.

Mom and I watched and listened as Dr. Wang, Santos, and Dr. Rivera spoke in Spanish to each other. When the talking was done, Santos interpreted the conversation for us.

"Dr. Rivera will do the cosmetic surgery first and when he's finished, Dr. Wang will perform the SRS. Both procedures should take about 18 hours, so you'll need to arrive at the hospital no later than 5AM. Do you understand?" Santos asked.

Mom and I told Santos that we understood.

Santos said something to the to the two doctors and then Dr. Wang smiled and bowed before making his way out of the office.

Santos told us that I would need to stay in the hospital for seven nights before I'd be well enough to go home. "She will have some swelling from the cosmetic procedures but that is normal and it will go away in about week," he said.

I asked them if they would really be able to everything in one visit.

Santos exchanged a few words with Dr. Rivera before giving me his answer. "The doctor says you will leave this hospital as an older woman. The two of you," he said as he pointed at Mom and I, "will look like sisters. That is what you want? No?"

"Oh yes," I said. "More than anything." I turned to the doctor and thanked him as graciously as I could.

********

Mom and I left the hospital feeling good about our meeting. Before leaving, Dr. Rivera gave us a description of the procedures he would be doing. According to Santos, Dr. Rivera would be one of five doctors working on my team.

I didn't understand everything they were going to do, but I did understand it would be painful, but I shouldn't worry about it because I'd be under anesthesia. However, once the anesthesia wore off, he told me I could expect a lot of pain and discomfort.

At first I thought they'd just be injecting me with fat tissues and damaging my skin with lasers. This was true, but there would also be a good amount of bone shaving to my chin and cheek bones. Dr. Rivera wanted to make sure that no one would ever be able to recognize me as Darren Peterman again.

*********

We ate dinner early because I was supposed to arrive at the hospital on an empty stomach. Mom and I talked about nothing except the surgery. We were both fascinated by what medical science could do.

"Isn't it amazing" Mom asked? "You're going to walk into that hospital as a 16 year old boy and walk out as a 46 year old woman."

I did think it was amazing. It was a miracle as far as I was concerned.

**********

Every thing went like clock work the next morning. We arrived at the hospital thirty minutes early, which gave me an extra 30 minutes to think about what I was doing. I sat next to my mother and looked up at the exit sign above the door. Exit is spelled Salida in Spanish.

I wasn't thinking about running but I told myself I could if I wanted to. No one was making me do this because this was something I wanted to do.

"Nancy Peterman."

I looked over and saw a nurse standing in the doorway.

"Its time," my mother said as she tapped my knee before getting out of her chair.

"Can you go with me," I asked?

"I can try. The worst they can do is to ask me to leave."

The nurse led us to a room and handed me a surgical gown. Her English was somewhat mangled but I understood that she wanted me to strip down and put on the gown.

The nurse closed the door behind her and I undressed in front of my mother.

"Let me take one last look at that rascal before they chop it off," Mom said.

I wasn't sure, but I think she was trying to be funny, so I gave her the benefit of the doubt by laughing.

Several minutes later, another nurse stopped by and she took my temperature and blood pressure. I assumed everything was okay, because she didn't say any thing about it as she wrote it down on my chart.

That nurse left and my mother and I spent the next 30 or so minutes waiting, mostly in silence. I felt like we should be talking and maybe she felt the same way, but I didn't know what to say and I guess she didn't either.

I was kind of relieved when another nurse showed up. She led me out into the hall and helped me on to a gurney. Mom followed as an orderly pushed me down the hall to the operating room. I felt my heart pounding fast.

Oh my God! What am I doing, I wondered. They're going to cut my balls of and make a woman out of me. This is so crazy. Its insane. Why in the world am I doing this? I must be dreaming.

I turned my head to the side and saw my mother walking beside me, keeping pace with the orderly. I told her I loved her.

"I love you too, Sweetheart," she said. "Is every thing okay? Are you feeling alright?"

I knew this was her way of saying I could roll off the gurney and make a mad dash for the exit. "Every thing is great," I lied.

A nurse stopped my mother as the orderly pushed me past two big doors. There was a man in a white coat waiting for me. He smiled and said something in Spanish. I heard the door open behind me and my mother and the nurse who had stopped her joined us in the room. Several words were exchanged between the doctor and the nurse. The doctor nodded and the nurse left.

Mom told me that the doctor was an anesthesiologist and that she was going to stay with me until I became unconscious.

The doctor had me roll over on my side and my mother held my hand as I felt a painful prick in my spine.

"He's giving you an epidural," Mom said. "I had one when I gave birth to you. Its only going to hurt for a minute or so and then you'll feel good."

"Is it going to knock me out," I asked.

"No, I don't think so. At least it shouldn't. I think he'll give you something else to put you to sleep.

The doctor covered my face with a mask after he finished giving me the epidural. I remember thinking that it smelled sweet, as my mother's face and her voice drifted over me in the far distance.

I thought I'd go to sleep and just pass out, but it wasn't like that. I guess you'd call it dreaming but it felt more real than that.

It's not like I've ever had a near death experience, but that was what it was like. It felt like I was dying and my life was passing before my eyes. And it wasn't just me who was seeing and feeling it. Everyone I ever knew was there and they knew everything I was thinking and they were seeing me for what I was. I felt exposed, ashamed, and remorseful.

I saw myself as a boy, living large on the football field and fucking girls in the back seat of my car. It was more than imagination. It was total recall. I'd been a boy and I'd been good at it and I had enjoyed it. So why was I doing this to myself?

Someone hit the rewind button on my brain and I saw my self as a little boy of 5 or 6, sitting on my mother's bed and watching her smoke as she put on her make-up. Was my little penis hard? I think it was, but I didn't know why.

The scene changed and I was still a young boy but I had done something wrong. Mom and I were back in her bedroom and I was leaned over her lap with my naked ass exposed. I saw the two of us in her mirror as she spanked my bare bottom with a cigarettes clutched between her teeth. I should have been scared or at least in pain, but the expression on my face was full of wonder and awe as I watched her smoke and spank me in the mirror. She looked so strong and powerful and I loved her for it. Did she feel my little penis poking against her thigh?

Several years passed and I saw myself alone in my parent's room, going though my mother's dresser. I felt the smoothness of her silky panties against my fingers. What would it feel like to put them on, I wondered? I urged my younger self to stop but he didn't hear me. I watched in horror and anger as the little boy took off his clothes and replaced them with his mother's silky garments.

What would my life had been like had I resisted, I wondered?

I saw the little boy eyeing his mother's pack of cigarettes. We both knew they were bad, but neither of us could resist the need to slip one out of the pack and hold it the way we'd seen our mother do thousands of times before.

Did I think I looked pretty and all grown up waving that unlit cigarette in the air as my little penis poked out against my mother's panties?

God help me. Make it stop!

There I was in my bed, a couple years later, jacking off into a pair of my mother's panties while thinking about Mr. Elden, my father's friend. I remember that night well because it was the first time I had ever fantasized about an older man fucking me. I imagined my parents were there in the room with us, applauding and cheering me on as Mr. Elden fucked me hard, the way I imagined my father fucking my mother.

A sense of remorse filled me as the little boy ejaculated into our mother's panties. We both knew what we had done and felt ashamed.

I watched the little boy and listened to his thoughts as he aged before me. I felt the excitement in his groin as he yearned to dress like our mother and be like her. I watched him as he spied on Mom and Mrs. Jackson and Mrs. Estes as they sat around the kitchen table smoking and gossiping. I felt his desire to join them at the table as their peer, dressed like them and smoking like them, and talking about all the things that older women talk about.

I saw myself on a date with Madison Bulloch, kissing her and thinking about how she was wasting her life by not taking up smoking. If I had been a girl I would have started smoking in a heart beat, and some day when I was older, I'd be a woman like my mom, smoking and puffing, and looking pretty and fucking.

Oh God, help me. Make it stop…but it didn't stop.

Although it had never happened, I saw myself standing in a room surrounded by everyone I knew. I was dressed in my mother's clothes and smoking a cigarette for them all to see. The looks on their faces said it all. They were disgusted and so was I.

Why did I want to be a woman….an older woman, like my mom? Why was I so willing to give away my life as a boy and my future as a man? Why was I in such a hurry to grow up?

I saw my self sitting on the edge of my bed holding up a bra to my flat chest and I asked him why? Why do I want to do this? Why do I want to be like Mom? He laid the bra on his lap and looked up at me, and that was wrong. He shouldn't have been able to see me, much less hear me or talk to me, but there he was, looking me in the eye and shaking his head.

"You did this to us," he said. "This is all your fault. You ruined my life. You ruined our life."

"But why? Why do I want to do it?" I asked. "How come I can't stop by myself."

He sneered at me as if I was dog shit under his feet and said, "Don't ask me. Ask Mom."

"Ask me what, Honey?"

I don't know how my mother got there because I didn't see her come in, but she was standing beside the bed, next to the boy who was myself. She was smoking a cigarette and looking at me as if I was crazy, which I most certainly was, but she didn't have to look at me like that. Didn't she know how bad I was hurting?

"Why do I want to be like you?" I asked.

Mom took a puff from her cigarette and exhaled the smoke into to a giant cloud that filled the room. I felt myself coughing and hacking and gasping for air. I couldn't see her and then I did.

Her face was blurry, but it was my mom and she look both happy and worried. "Oh my God," she said. "Darren! Can you hear me? Darren, wake up!"

"Where am I?"

"You're in the hospital, baby."

"The hospital. Did they…? Am I….?"

Mom bit her lip and wiped a tear from her eye. "Yes, sweetheart. You're a woman now."

I moved my hands from my side and reached for my balls and my penis, but they were both gone. A wave of emotions fell over me as I realized the gravity of the situation. I'd gone to sleep as a boy and had woke up as a woman.

A woman! Do I have breasts, I wondered? Of course I do! They blocked my view of the door. "Is it okay to touch them," I asked.

"Yes, sweetheart. Its okay. You're all healed. We were just waiting for you to wake up."

"But I thought I was supposed to sore. And how come there aren't any bandages on my face. Didn't Dr. Rivera say I'd be all blistered and everything."

"You were all blistered but there was a problem during surgery. You almost died, honey."

"But I'm okay now?"

"Yes, Sweetheart. You're fine, but you've been in a coma."

"A coma? For how long?"

"Tomorrow would have made three months," she cried. "I thought we'd lost you."

"Its okay, Mom. I'm okay. You don't have to cry. Everything is going to be alright now."

"Are you hungry?" she asked.

I told her I was starved, but that before I did anything, I wanted to see myself. "Is there a mirror?" I asked.

"In a minute or so," she said. "I think we should probably tell someone you're awake. I know the doctor is going to want to talk to you first."

"Is something wrong, Mom? How come you won't get me a mirror? Was there another problem with the surgery? You know…besides me not waking up and every thing?"

"Its nothing to be worried about, Darling. Its just that you've had a lot cosmetic surgery done and well…you don't look like your self and it might come as a shock. And I just think we should wait a while, until you've been awake a little longer. The important thing to keep in mind is that you're a woman now and you'll never be a boy again, and that is what you wanted. Isn't it? Please tell me its what you want."

My mother was scaring me. Was there something wrong? Obviously something had gone wrong during the surgery, or else I wouldn't have been in a coma for three months.

She asked me the question again. "Please, Honey. I need to know. Do you still want to be a woman?"

I asked her if I had a choice. "Can the doctors do it over again and change me back?"

"No," she said sadly.

"Then yes, I want to be a woman. It's okay Mom. Its what I wanted. You didn't do anything wrong?"

I took her hand in mine and she started sobbing, which only scared me more.

"Mom. What's wrong? You can tell me. Am I ugly? Is that it?"

"No, Honey? You're not ugly."

"Then let me see."

"Okay then," Mom said as she picked her purse off the floor and rummaged through it for a compact.

My breath grew more shallow as I anticipated the worse. She opened the compact and held the mirror up to my face for me to see.

THE END

Author's Note: This is the final chapter of, "Like Mother Like Son". However, its not the end of Darren Peterman's story. Remember when I asked for comments about what age Nancy should be? One reader suggested ending this story and making two different endings. I liked that idea, so that's what I'm going to do.

Be on the look out for:
1) Like Mother Like Sister
2) Like Mother Like Mother


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