18 year old crossdresser Brian Oldham thinks his life would be better if he could look like an adult woman. He and his mother, Barbara, hatch a plan for him to live out his dreams for the summer, working as a 45 year old chain-smoking waitress in a diner. Not content with stage make-up, Brian takes the aging too far and the changes are permanent! Watch out, Papaw Frank!

Teenage Sissy Smoking Grandma
by Sharon Parsons
March 1, 2015
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Chapter 1 of 7
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Barbara Oldham held up a bra to check the price as her eighteen year old son, Brian, ran his fingers across the silky fabric of a nightgown. To Barbara, he seemed pained and awkward, as if he was trying to look invisible as he admired the silky garment. Barbara felt awkward too, because she knew about her son's secret fascination with her closet.

It wasn't a secret at all in his younger years. When Brian was as young as six years old, he was openly playing dress up in his mother's clothes. She hadn't thought anything about it back then. All kids liked to played dress up and it wasn't like Brian had grown man clothes to play with. His father had left her for another woman a year earlier.

Kevin, her 13 year old, was turning out normal. Normal? Was that the right word? Using it made Brian sound abnormal. No, Barbara thought. Kevin and Brian are different. But Kevin is all boy.

Kevin was spending the weekend fishing with Frank, her step-father. Frank had married her mother when she was just five years old and had been a real father to her. After her mother's death from cancer three years ago, the two had remained close. And why shouldn't they? He was every bit a father to her and a grandfather to her two boys.

Both boys loved their Papaw Frank and he loved them, but Frank had more in common with Kevin than he did with Brian. Frank was a man's man. He loved to hunt and fish and watch sports on TV.

Barbara Oldham was 45 years old and working as a waitress in a diner. The restaurant was named after the owner, Sarah Conroy, and Barbara had worked there for almost 20 years. Sarah's Diner was like a second family to her. The women that worked there beside her were her best friends. It was a pleasant place to work with pleasant customers and the tips were good.

She hung the bra back on the rack and picked up another as she continued to watch her son from the corner of her eye. He was walking down the aisle that housed the panties. He was keeping his hands to himself, but Barbara could tell he wanted to touch.

She felt sorry for her son. Maybe it was because he was a little on the flabby side, or the fact that at 5 foot 4", he was shorter than most boys his age, but for whatever reason or reasons, Brian was a lonesome outcast with no self-esteem or self-confidence.

She had meant to have a talk with him about his covert dressing at least a million times, but the time had never been right. Either she was late for work or she had just lost her nerve. But that hadn't stopped her from talking about it with her friends at the diner. All the other waitresses and even Sarah Conroy knew about her son's crossdressing. It was her friend, Doris Smith who had planted the seed of doubt that Brian's dressing wasn't a phase. Doris had a nephew who was now her niece. What if Brian was like that? What if he wanted to be a girl? Would Barbara love him or her any less? Of course she wouldn't. Brian was her baby and she loved him and wanted him to be happy.

She thought about what her friend, Carol Watson, had suggested. It was Carol who said that Brian might be a crossdresser. And she said a lot of crossdressers are straight men who just like to dress up as women. Maybe Brian didn't want to be girl. Maybe he just wanted to dress like one in secret. Maybe she should just keep her mouth shut and let him work things out for himself...or maybe she should start acting like a real mother and start being more accepting and supporting. She was his mother and she could tell her son was in pain. Maybe she could take away the pain by taking the shame away from his secret.

Brian returned from his jaunt down the panty aisle and was standing not too far away from her, running his hand across a rack of nightgowns, trying to appear nonchalant. Its now or never, Barbara thought as she surprised herself by allowing some telling words to slip from her mouth.

"That's a pretty gown. Don't you think?" Barbara asked as she picked one of the nightgowns off the rack and held it up for them both to admire.

"I guess so," Brian said in a tone of voice that tried to sound disinterested.

"Do you like it?" Barbara asked.

"I don't know. I guess so. But why are you asking me?"

"Because I think it would look good on you," Barbara said. "Red is your color."

Brian took a step back and choked on his rebuttal. "That's not funny," he said.

"I wasn't trying to be funny. I was just trying to start a conversation that we probably should have had a long time ago. Don't you think its about time that we talked about you wearing my clothes?"

Brian's shoulders went limp and he deflated in front of her. "I don't wear your clothes," he lied. "I'm not gay."

"I didn't say you were gay," Barbara said as she put the gown back on the rack and started thumbing through the sizes until her hand found a gown with a medium tag. "I know there are some men who aren't gay but they still like dressing up as women. Its called crossdressing. Are you a crossdresser, Honey?"

"Mom! Please!" Brian whined. "Not here. I don't want to talk about it."

"Why not talk about it here?" Barbara asked. "Here is as good as any place. I know you like wearing women's clothes and you know it too, so what's wrong with the both of us admitting it?"

Barbara saw her son's lip quiver and a tear begin to fall from his eye. She watched as he tried to wipe it away but it was quickly replaced by a new tear. Her son was quickly losing control and she could tell the weight of her accusation was smothering him. She reached inside her purse and retrieved a wad of facial tissue. "Let me get that for you," she said as she dabbed his cheek with the tissue. "You know I'm not mad at you and I'm certainly not trying to embarrass you," she said. "I just think its time for you to come out of the closet about this. Its nothing to be ashamed of. I know you can't help the way you feel. Its just a part of who you are and you need to know that I love you and accept you and support you no matter what. You know that. Don't you, Honey? You know that I love you no matter what. Right?"

Brian sniffed and said, "I know you love me. I love you too. I love you so much, Mom."

"Good," Barbara said. "That means we're both on the same page about this and we can talk about it without being embarrassed."

"But I am embarrassed, Mom. And I can't believe we're really talking about this. I never thought we'd talk about this. Not ever!"

Barbara smiled warmly at her son and hugged him, as the other shoppers in the store walked by and pretended not to notice their embrace. She held him close and rocked him in her arms. Nothing was said between them for about 30 seconds or so. And then she whispered in his ear, "Can I buy the gown for you?"

Brian sniffed and nodded his head against her shoulder.

"Good," Barbara said as she let go of him and handed him the red baby doll.

"I can't believe we're really doing this," Brian said as he held the gown down at his side in hopes of drawing less attention to himself.

"I was looking for a bra before this started," Barbara said. "I think maybe you need a bra too. Don't you think?"

"Oh Mom," Brian winced as he shook his head.

"Its okay, Honey. I know this must be weird for you because its weird for me too, but if you're going to do this, then I want you to do it right. And to do it right, you're going to need a bra. For that matter, you're going to need a lot of things. I know we're about the same size, but I think you're going to want a younger look. My clothes are so old and frumpy and the styles for girls your age are so cute!"

Brian sighed and said, "You're right," he said. "This is weird but its about to get even weirder. I don't want to dress like a teenage girl. I want to dress like an older woman?"

"How old are you talking about, Honey? Twenty? Thirty?"

"Oh no, Mom. A lot older than that. I want to be your age. I want to be an adult woman. I hate being a kid. I hate my life!"

The look of puzzlement on Barbara's face grew more intense as she tried to digest her eighteen year old son's words. "Now I'm confused," she said.

"But I'm not," Brian said. "I know what I want and I've wanted it my whole life and now that we're finally talking about it, I just think you should know the truth. And the truth is that I want to be like you. I want to be strong and powerful. I want to be respected, and I feel like people would respect me more if I was an older woman."

"I'm sorry, Sweetheart. I know you hated high school. Kids can be so cruel and mean, but things will get better now that you've graduated, if you give it a chance."

"Yeah, Mom. Things will get better- when I'm older, and I don't want to wait until then. Look at me, Mom. I suck at being a boy."

"Maybe we should take a little break from shopping and talk about this during lunch. I think I really need a cigarette about now," Barbara said. "We can leave the gown here and pick it back up after lunch."

*****

They walked through the mall to Ruby Tuesday's in silence. Each one was thinking about what they might say when it came time to say it. After all, there was so much to say now that the cat was out of the bag.

When they got to Ruby Tuesday's, Barbara requested a seat in the smoking section. Even though it was after 2:00, they had to wait for their seat because the smoking section was crowded, being the only place inside the mall where smoking was allowed.

Once they were seated, they ordered their lunch along with their drinks to save time. Barbara ordered a grilled chicken salad with a glass of wine and Brian ordered a hamburger and a Coke. Immediately afterwards, Barbara fished a worn leather cigarette case from her purse and pulled out a Virginia Slim.

Brian did his best to control his fascination with his mother's smoking as she lit up the first of many. Brian didn't smoke...but he loved the idea of being a chain smoker like his mother and her friends. It was a fantasy of his, one that he played out with unlit cigarettes in front of his mother's mirror.

He marveled at the feminine way in which his mother held her slim white cigarette. It was something he had tried to get the hang of himself in front of the mirror, but he was overly dramatic with his gestures. His mother and her friends on the other hand were so natural and glamorous. His mother's words interrupted his thoughts.

"Lets talk about what you said back in Macy's about wanting to look like an older woman. To tell you the truth, you caught me so much off guard that I don't know where to start. So for starters, I've got to ask...Do you want to crossdress and look like a woman or do you want to be a woman for real? You know...like have a sex change?"

Brian answered immediately. "I'd get a sex change in a heart beat if I could," he said. "I think it would be fun to be a woman for real!"

"You think it would be fun?" his mother asked crossly.

"I knew you wouldn't understand," Brian said sadly.

Barbara took a puff from her cigarette and blew out an anxious stream of smoke. Brian thought the slim white cigarette between her fingers made her look so sophisticated and powerful. What he wouldn't give for that kind of power...the power of a woman!

Barbara swirled the tip of her cigarette around the rim of the ashtray. "I'm thinking about something," she said. "I'm thinking about a way to try this out. I think that if you had a chance to live out your dreams, you'd see that being an older woman is not as fun as you think it is."

"But what if it is fun? What if its better than being a boy? What then?" Brian asked excitedly.

"We'll cross that bridge when we get there, but for now, lets just focus on the summer. High School is behind you. College is in front of you, and you have a whole summer in-between. What would you think about working at the diner as an older waitress for the summer? I could talk to Sarah and I'm sure she'd let you do it. That is, if you could pull it off. You know...the age and make-up part. So how would you do it?

"Oh a little bit of this and a little bit of that and some make-up. I've seen all kinds of videos about looking older on Youtube," Brian said.

"Okay then. I'll leave it up to you. Just let me know if I can help," Barbara said. "Of course it won't be all fun and games. It would be a real life test. You'd have to live and work as an older woman 24/7 for the whole summer. That means you'd have bills to pay and you'd have to buy your own things. Your life would be just like an adult's. That means no dressing up as a boy to go out with your friends. We'd tell them that you went away for the summer."

What friends, Brian thought as he replayed his mother's words and then expounded on them. "Just like an adult woman," he asked? "Are you saying I'd really be an adult? And I could live like an adult and do the things adult women do?"

Barbara grinned and slid her glass of wine toward him. "What?" she asked. "Do you want to drink like an adult? You can have a sip if you want."

"Really?" Brian asked as he picked up the glass.

"It's OK. Go ahead. I don't mind. I know you're in a hurry to grow up and I don't see anything wrong with having a drink now and then as long as you're responsible about it."

Brian swirled the tart grape liquid across his tongue and swallowed.

"Do you like it?" Barbara asked.

Brian smiled and said he did. "What about other things?" he asked. "Will you let me do anything that a grown woman can do?"

"What kind of things were you thinking about?"

"Oh...just stuff, you know. Whatever..."

A wicked grin spread across Barbara's face as she tried to hone in on her son's thoughts. "You aren't talking about dating men, are you? Older men? Is that it, Honey?"

"Mom!"

"Don't act so offended. If you're going to do this, then you need to be honest with me. Are you going to sit there and tell me that you've never thought about dating men when you were thinking about being woman? It does kind of go with the territory."

Brian blushed. "Mom, just because I've thought about it, it doesn't mean I want to do it for real. And when I do think about it, it's not gay. It's like you and Ted."

"Problem solved then," Barbara said as she finished her cigarette with a long puff and put it out in the ashtray. "Its okay with me if you want to date men. And for what its worth, I think you should date them. I want you to experience what its really like to be a woman. If you do, then you might decide its not everything you built it up to be." She picked up her cigarette case and pulled out another Virginia Slim. "Anything else you want to talk about it while we're talking about the rules?"

There was something else that Brian wanted to talk about, but he was hesitant to bring it up. After all, he knew how his mother felt about smoking and it was a whole other ball of wax. Maybe he shouldn't press his luck. He looked across the table at his mother as she brought the white cigarette up to her lips. How could he ask for her permission to take up smoking? How could he not ask?

"Mom?"

"Yes, Sweetie. What is it?"

"Promise you won't get mad?"

Barbara exhaled and shrugged. "How can I be mad at you. I asked you to be honest about your feelings. Of course that doesn't mean I'm going to be happy and it certainly doesn't mean I'll say its Okay with me, if its not, but I promise you that I won't be mad. What did you want to ask me?"

Brian squirmed in his seat as he stared down the cigarette between his mother's fingers. "Mom, I was wondering if it would be okay with you if I started smoking?"

The color rushed out of Barbara's face as her jaw dropped. "What? Did I just hear you say you want to smoke?"

Brian shrunk and nodded his head. "Yes," he croaked. "But remember. You said you wouldn't be mad at me."

"I'm not mad, Sweetie. I'm just a little surprised and disappointed that you'd want to take up such a horrible habit. I always thought you were smarter than that."

"You smoke and you're the smartest woman I know," Brian said. "And the most beautiful," he added. "I'd give anything to look as good as you do when you smoke."

"Really?" Barbara asked, "You think I look pretty when I smoke?"

Brian blushed and nodded his head. "Yeah, Mom. I do."

"It's okay, Sweetie. I'm not trying to embarrass you. It's just that Ted says the same thing."

"Then you know what I'm talking about?"

Barbara took a pensive puff from her cigarette and inhaled the smoke deep inside her chest before exhaling. "Lets say that I do. I'll be completely honest with you about my smoking. I started because I wanted to look pretty and impress men. I wouldn't have started if I thought it made me look ugly. But like I was saying, I want to be honest about it, and there's so much more to it than just looking pretty. Looking pretty is a high price to pay for ruining your health."

"Look Mom. I know all about the health stuff. It's not like I was born in a cave. You know?"

Barbara shook her head and sighed. "I remember saying something like that to my mother when I wanted to start smoking."

"Oh yeah? Well how old were you when you started?"

She sighed again and said, "I won't lie to you. I was younger than you are. I think I was 14 when my parents gave me their permission." She trimmed the ash off of her cigarette in the ashtray and asked, "Why is it so important that you start smoking? Do you think smoking will make you a better woman?"

Brian nodded his head and said, "It would make me more like you...so yeah...I'd say it would make me a better woman. Don't you see, Mom? I want to be just like you. I want to look like you and talk like you and dress like you and yes...I really really really want to smoke like you."

"Oh, Dear!" Barbara gushed. "Are you sure, Honey? Because if I let you do this, then you're probably going to get addicted, and I don't want you to have any regrets."

"It's okay, Mom, and I promise you that I won't have any regrets."

Barbara reached across the table and touched the top of her son's hand. "In that case, I hope you really do like men, because when they see you smoking, you're going to have to beat them off with a stick!"

"Ah geese, Mom! I'm not ready to go there."

"So its a deal? I'll buy all the clothes and stuff you'll need in the beginning to get started, but after that, once you start working and making money, you'll be on your own. You'll live at the house, but you'll pay rent. As soon as you put on a dress, you'll no longer be my son. You'll be my sister. And if it turns out that its too much for you, you'll hang up your dress and become a boy again. Do we have a deal?"

"Deal!" Brian said excitedly. "What do we do first?"

"We're about the same size, so you can wear my clothes. But you'll need some things of your own...like shoes and bras and panties. And of course you'll need some breast forms. I'm supposing you want to be a D cup like me?"

"Mom. I can't thank you enough for letting me do this."

"I just want you to be happy, Sweetheart. And if being just like me will make you happy, then I'm all for it. However, I will warn you that it might be more than you bargained for. Are you ready to go back to Macy's?"

*****

Brian was a nervous wreck inside of Macy's. After all, he was shopping for panties and bras...and his mother wasn't making things easy on him. Discretion was the furthest thing from her mind as she expressed herself loudly for all the other customers to hear.

"Do you want to wear a thong or do you prefer granny panties?" she asked. Brian chose granny panties. "Obviously you're going to need some white panties, but you're going to need some colors too. What's your favorite color, Sweetie? Pink and black are nice.'

Bra shopping was even worse as Barbara held up each bra up to his chest, the way she would if she was trying to fit him for a shirt.

"This is a 44D, the same as I wear," Barbara said. "Do you want big boobs like Mommy? What? I didn't hear you. I asked if you want big boobs like Mommy?" she said with a devilish grin.

"Yes, Mom."

"Yes...what?"

"Yes, I want big boobs like you."

A heavy-set woman in a floral print dress looked at Brian and smiled. Brian bit his lip and melted. He was humiliated. His mother on the other hand seemed thrilled by the game.

"Why are you doing this to me, Mom?"

Barbara grinned at her son and said, "If you can't stand the heat then maybe you should get out of the kitchen."

"What does that mean?"

"It means that this is only the beginning, Honey."

"So you're going to embarrass me even more and make my life even more miserable than it already is?" Brian asked.

"No. Not me. I'm just saying that you're choosing a tough road for yourself. The people in the store are just strangers. You shouldn't even be caring about what they think. But real people you do care about might and probably will find out if you go through with this. Now I'm not saying you're making the wrong choice. It might be the best thing in the world for you. But I am saying you better get some tougher skin. Am I making sense or do you just think I'm a monster?"

Brian sighed and nodded his head. "You're right and you're not a monster. But this isn't easy for me. Everyone in the store thinks I'm a sissy."

"Well aren't you a sissy? Real boys don't go shopping with their mothers for bras and panties. Don't stand there and tell me you're not enjoying this just a little bit. This has to be a dream come true for you."

Brian nodded his head and agreed with his mother. "You're right, Mom. This is a dream come true for me. Thank you for doing what you're doing."

"In that case, we've got a lot more shopping to do. We still need to get you a pretty cigarette case for all those girly cigarettes you'll be smoking. Not to mention you still need some shoes."

*********

It was half past seven when Brian and his mother got back home. His head was spinning. Was this really happening? How could it...but it was.

"I know you're probably in a hurry to try on all your new girly stuff," his mother said, "But first things first. If you're going to do this, then you might as well do it right. And that means shaving your body."

Brian argued that he didn't really have that much hair, but Barbara led him to her bathroom and showed him her razor. "Tomorrow is Sunday. You have all day to get dolled up and practice your make-up. Besides, you're going to love the way that silky nightgown feels against your skin once your freshly shaved. And tomorrow we're going to want to do something with your eyebrows."

Later that night, in the privacy of his room, Brian discovered what his mother meant when she said he would appreciate the feel of his silky nightgown against his freshly shaven skin. He fell asleep to pleasant dreams after jerking himself silly.

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Barbara woke up on Sunday to an empty house. She found a note in the kitchen from Brian saying that he went to a tanning salon and would be back soon. Two hours later, she received a horrifying call from a nurse at the local hospital saying that Brian had been admitted with second degree burns all over his body. The nurse told her to come as soon as possible.

When she arrived, she was introduced to Brian's doctor who explained that he was in a medically induced coma to protect him from the pain.

"How did this happen?" Barbara asked.

The doctor told her that the paramedics who had cared for Brian had found an empty bottle of St. John's Wort and a bottle of liquid paste that was made from Borax and Clorox. He explained that St. John's Wort is a natural anti-depressant that makes the skin super sensitive to sun light. Used together with the Borax, Clorox, and the intense radiation from the tanning bed's ultra violet lights, Brian had experienced 2nd degree burns on 95% of his body.

"Oh my God!" Barbara said. "Will he be okay?"

"The burns will heal in about two to three weeks, but the damage to his skin will be permanent. I'm sorry, Ms. Oldham, but your son, Brian, has effectively aged his skin by fifty or sixty years. When his skin heals it will be permanently be aged and wrinkled. Do you know why your son would do something like this?"

The doctor listened intently as Barbara explained her son's desire to become a middle aged woman. "I thought he was just going to use make-up," she said.

"You know," the doctor said, "we have a good chance of turning this into a positive. We could effectively grant your son's wish to become an older woman, albeit a much older woman. Would you like for me to arrange a meeting with our psychiatrist on call. I'd also need to bring in surgeons who could do the cosmetic work."

Barbara agreed with him. "You're right," she said. "I think its for the best."

"In that case," the doctor said, "I'll have the nurse bring you some papers to sign while I make the calls."

********

Barbara was sitting in a chair beside her unconscious son, when a nurse came in and said the doctors were ready to talk to her about Brian in the conference room.

Once inside the room, Brian's primary doctor introduced her to a psychiatrist, a dermatologist, a dentist, an eye doctor, and a lawyer. The discussion went on for almost two hours and many recommendations were made.

Brian's primary care doctor ended the meeting by saying, "Okay, so we're all in agreement about Brian. We will keep him in a medically induced coma until all the procedures are completed. When he wakes up in two weeks, his new name will be Brianna and he'll  have the body of a 65 year old woman.

******

One by one, the doctors took their turn working on Brian. He was implanted with large breasts that sagged to his stomach. His hips were widened. His eyesight was intentionally damaged so that he would need to wear thick glasses. His teeth were extracted and replaced with dentures. His skin was stretched so that it would wrinkle even more. His lips were injected with collagen and his cheeks were puffed out with Voluma and of course he was pumped up with female hormones.

After his bandages were removed, but while he was still in a coma, Barbara hired a cosmetologist to arch his eye brows, do his nails, and dye his longish brown hair blonde. She even cut it in a cute shoulder length style that fit her new age.

The hospital's lawyer saw to it that his birth certificate was changed to reflect his new gender and age. He would become known as his mother's aunt and his grandmother's twin sister. All that was left to do was to end the coma inducing medication and wait for Brianna to wake up. If you want to purchase the entire book (Chapters 1 -7) it is available at Teenage Sissy Smoking Grandma