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Cigarettes Are a Girl's Best Friend

Author: 

  • Slim V.

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Crossdressing
  • 7,500 < Novelette < 17,500 words
  • Migrated from Classic BigCloset.

13-year-old Jimmy gets caught dressing in his mother's clothes and smoking her cigarettes. Is he a big girl now?

Cigarettes Are a Girl's Best Friend

by slimv


Jimmy dangled his legs off the edge of his mother's bed as he watched her get ready for her date with Bob. She was sitting at her vanity, brushing her blonde hair. A long white cigarette dangled from her lips. He squinted to see the telltale ring of lipstick around the filter as she placed it to rest in the ashtray.

At 13, he was short and small for his age. His size, along with his shoulder length blonde hair had made him a target for the bullies in his school. His frame was slight, but his hormones raged--a symptom of his puberty, according to his mother.

Girls, women in particular, fascinated him. He admired and envied them. Perhaps things would have been different if his father hadn't died when he was so young. But things were as they were and he and his mother made the best of their situation. They had been well off while his father was alive, but a sizable life insurance policy and some good investments had created a comfortable financial climate. With no male influence in his life, Carol, his mother, had become his role model.

The smoke from his mother's cigarette drifted hypnotically toward the ceiling. She made it look so feminine and glamorous. Some of the girls in his school smoked and he was drawn to him, but he wasn't their type. They went for the big guys- the bullies that made his life miserable.

Things would change some day. His mother told him that. She knew all to well the troubles her son was experiencing. She told him that when he was older the playing field would level. The girls that had nothing to do with him today would vie for his attention when they saw how intelligent and resourceful he was. Until then, he would need to be patient. If he couldn't have the girls of his dreams, he could at least dream about them.

While most boys his age were thinking of sex with girls as they pulled themselves to orgasm, Jimmy busied his mind with thoughts of becoming one with them. He fantasized about how they felt and what they thought. How did they feel when they put on their frilly dresses and slept in their silky nightgowns? Did they want to smoke? What about the ones that did? Did their parents know? Had they asked for permission?

Dana was a smoker and her parents were well aware of it. She even had their permission. Dana was Dana St. James. She was a girl in Jimmy's class and the subject of many of his fantasies. She was beautiful and dressed the part. He was in awe of her.

He remembered the thrill he felt on the first day of school when he saw the pack of cigarettes in her purse. A week after that, he saw her at a restaurant with her parents. They were sitting in the smoking section and she was having a cigarette with her mom. She looked so grown-up and elegant. He remembered the look of pride on her parent's face, especially her mother's, as she watched her young daughter smoke like a woman. He didn't know if it was true, but it was rumored that she started smoking when she was 9 and her parents gave her their permission when she was 11. He'd heard one girl say Dana smoked almost two packs a day!

Jimmy couldn't help but notice a double standard when it came to the female sex. Girls did things guys could never do. It was perfectly acceptable for a young girl to smoke. It was a way of expressing her femininity. Guys were expected to stay in shape by playing sports. Girls didn't have athletics hanging over their heads. They could smoke and it even helped them keep their weight down. His mother was a prime example. She ate what she wanted and thanks to the three packs of cigarettes she smoked each day, she looked fabulous! And what about the clothes girls wore? They were pretty- not like the plain pants and shirts guys were forced to wear. He wondered about that. Why was it good for girls to wear pretty clothes and bad for guys to do it? Something about it seemed unfair.

His mind wandered back to smoking as his mother applied her lipstick and took a deep drag from her Virginia Slim. Obviously men smoke too, but guys looked strange to Jimmy when he saw them smoking. Something about it didn't look right. He knew of only two guys in his middle school that smoked. They weren't cool like the girls. They were trash. And nobody liked them.

"Are you sure you're going to be OK tonight? I should be back by midnight. Don't wait up for me. Do you understand?"

"Huh? Oh yeah. Sure Mom. I'll be OK. Have a good time tonight. Take your time. Don't worry about me."

Carol Higgins smiled and approached her son with her made-up and face and cigarette in hand. Jimmy wondered if she could sense his hard-on as she bent down and kissed him on the cheek. The smell of her smoky breath drove him wild. She giggled as she wiped away the remnant of her lipstick from his cheek.




He flipped channels as he sat in the chair once occupied by his father. Nothing on TV kept his interest. Situations like this were rare and he felt the need to make the most of his time alone in the house. He should at least jack-off if nothing else, but he could do that anytime. Thoughts of Dana and his mom crept through his mind. He couldn't get past the images of them smoking as if it was the most normal thing in the world for them to do. He wondered what it would be like to smoke in front of his mother. Would she smile at him the way he'd seen Dana's parents smile at her? He'd give anything to know that feeling of acceptance.

He laid the remote control on the coffee table and got up from the chair. He started for the stairs but made a detour at the kitchen and tried to take his mind off his desires by opening a Coke and taking a big swig. He put the can down beside one of his mother's many ashtrays that littered the house like diamonds. The sight of lipstick stained filters made him hard. He picked one up and did his best to wipe away the ashes before sticking it between his lips. He was excited by the idea of putting his lips where his mother's had been. He was beyond reason, but he told him self he would not succumb as he walked up the stairs toward his mother's room.


As he entered his mother's room, all he could think about was what a sick son of a bitch he was. He had felt these urges before but had always pushed them aside without acting on them. In his heart, he knew it was wrong, and the guilt plagued him as he pulled out his mother's dresser drawer.

He opened the drawer and allowed his fingers to navigate the silkiness of her gowns. This wasn't the first time he had looked upon his mother's bras, panties and slips. But time had never been on his side the way it was now. He wanted more than to just touch.

The temptation was immense and so was his fear. He cocked his ear and listened for any sign of danger. All he heard was the sound of the TV coming from downstairs. He took a deep breath and steadied his nerves as he removed his mother's long red silk gown from the confines of the drawer. He held it by the shoulder strap. The gown's hem fell to the carpet. It was gorgeous and he loved the way his mother looked in it. He wondered how he would look and feel if he put it on.

The urge to strip and put it on was strong, but he held off. If he were going to do something so ludicrous and wrong, he would do it right. He laid the gown across his mother's bed and pulled out another dresser drawer. The feel of his mother's panties was heaven to his fingers and he withdrew a pair for further study. He laid it on the bed beside the gown and went back for more.

He examined the clasps on his mother's bra as well as the large cups. He wondered how he would ever get it hooked. He wasn't very coordinated. The idea came to him that could connect the clasps and then shimmy into the bra feet first.

After removing his clothes and leaving them in a pile beside the bed, Jimmy worked himself into the bra and pulled it up against his small flat chest. He opened his mother's underwear drawer again and picked out more of her panties, not to wear, but to fill the bra's deep cups. Satisfied with the results, he slipped on his mother's panties and pulled the gown over his head.

The reflection of his false femininity in the full-length mirror astounded him. The stiffness of his erection against the silk gown ruined the effect but felt so good. He was powerless to leave well enough alone as he took a seat at his mother's vanity and tried to make-him self up the he'd seen his mother do.

So many things to play with! What to do first? He began with the foundation and applied it sparingly and followed with blush and a little eye shadow. He applied the lipstick awkwardly. It would be obvious to anyone watching that he had never done this before. None of this mattered to Jimmy. It was the tingle in his groin that mattered as he put the cap back on the lipstick and returned it to the vanity. He brushed out his long blonde hair giving it some body. He put the brush down, being careful not to disturb the full ashtray that sat beside his mother's pack of Virginia Slims. He got up and walked to the full-length mirror. He tilted his hips and smiled at his reflection. He liked what he saw even though it pained him. WRONG! This is wrong, but he couldn't stop now. Maybe these urges would leave if he gave into them all the way- at least just this once.

He returned with his mother's pack of Virginia Slims and lighter in hand as he modeled in front of the mirror. He removed one of the slim cigarettes from the pack and held it at an angle the way he'd seen Dana and his mother do. He moved it between his fingers so that the filter was between his fingers. This made the cigarette appear longer and more elegant.

He knew better than to light it. His mother would have a fit if she found out. Just last week she had given him a long lecture about the dangers of smoking. She told him how important it was to avoid and learn from her mistakes. If smoking was so bad then why didn't she quit? Why did anyone smoke if it was so bad? She had told him about addiction. He had grown up hearing that word, but in his mind "addiction" was just a word. So what? His mother was addicted to something she obviously enjoyed and looked good doing.

Jimmy put the cigarette between his lips and fumbled with the lighter. His thumb pressed against the steel wheel but nothing happened. He tried again and was surprised to see a flame appear. He nervously touched the tip of the cigarette to the flame and sucked on the filter the way he would suck on a straw if he were drinking a milkshake.

His mouth filled with smoke. The flavor was not as he expected. It was harsh and hot. He realized his error in judgment but was powerless to prevent him self from seeing it through. He looked in the mirror as his red lips opened and exposed a thick ball of creamy white smoke. He inhaled the way he'd seen Dana and his mother do. The smoke slid down his throat. It was the last thing he saw as his eyes slammed shut and his body reeled in pain. How do people do this he wondered as he clutched his chest and coughed uncontrollably?

He looked at his hunched over reflection in the mirror. His eyes watered. His chest felt as it were on fire. Yes, he should stop. He should walk over to his mother's vanity and put the foul cigarette out in the ashtray. This woman stuff was beyond him. He wasn't cut out for it. But somewhere within him, his determination swelled and he tried again. The smoke was still harsh, but this time he fought the urge to cough. Maybe this was how people really felt when they smoked. Maybe they just pretended to enjoy it, but Jimmy didn't think so. Dana and his mother had mastered this thing, and so would he.

He stood in front of the mirror and continued practicing, walking away now and then to ash the cigarette at his mother's vanity. He had to finish the cigarette any way. If he didn't smoke it down to the filter it would look out of place among the other butts.

As the cigarette burned down between his fingers, his confidence grew, and he began to move around the room, prancing with the cigarette, pausing to take puffs from it. He was proud of the way he was smoking. He may not like the way it felt, but he was in love with the way it made him look while wearing his mother's lingerie.

The alarm clock radio on his mother's nightstand said it was only 8:00. He had until midnight to enjoy his mother's clothes and cigarettes. The pack was almost empty and he knew better than to take it downstairs. It made more sense to get a fresh pack from his mother's carton. He knew she would never miss it.




Jimmy was in heaven as he lounged on the couch, watching TV, wearing his mother's nightgown and smoking her cigarettes. He had never felt so relaxed or more at peace. At ten o'clock he decided enough was enough and he didn't want to press his luck. He removed the make-up, put his mother's clothes back where he had found them and went to bed.

Carol let her self in a little past midnight. She scowled when she saw the TV on and the mess her son had left for her. But all in all, she had a good time on her date, and decided not to let a little extra housework bother her. After all, she should be pleased to see the house in one piece. She had heard stories of kids Jimmy's age inviting friends over and having parties while their parents were away. Her son was not that kind of boy- thank God! She locked the door and turned off the lights. The mess looked better in the dark.

Her son's light was still on so she looked in and saw him sleeping. She couldn't help but feel a burst of love in her bosom as she watched him sleep. She went in and turned off the light before kissing him goodnight.

If she had kissed him first, while the lights were still on, maybe she would have seen the bit of shadow that remained on his lids. But the clue eluded her. As she kissed his forehead, she couldn't help but notice the slight aroma of smoke in his hair.

Poor boy she thought. That's what he has to suffer through, living with a mother that smokes. She wondered if the kids at school made fun of him for smelling this way.

She closed his door behind her and turned off the hall light before entering her own room. She sat down at her vanity and lit a cigarette as she took off her make-up. She undressed and changed into a nightgown. The drawer of lingerie seemed disturbed. She noticed it but didn't give it much thought as she pulled the red gown over her head. She ran her fingers across the smooth fabric. She looked down and lifted the gown. She had felt something stiff. She wrinkled her nose in disgust. The stiffness she felt was dry semen. She must not have washed it after her last time with Bobby, her date from tonight. Oh well, she thought, at least it's a good memory, and with that she climbed in bed and fell asleep.




That first night of sweet temptation and satisfaction would repeat it self many times over the next three months. For Jimmy, each time was as wonderful as the first. Practice makes perfect and he had begun to master both the art of smoking and applying make-up.

Things didn't seem right to Carol. She began to suspect Jimmy was up to something. She was neat by nature but her closets and drawers had become increasingly disorganized over the last couple months. This disturbed her but she tried not to think about it. She wasn't an expert on teenage boys. Perhaps his behavior was normal. Why wouldn't her son be curious about females? He was probably satisfying his curiosity by searching through her things. But still, she should probably have a talk with him, but it seemed so weird.

She watched Jimmy in the mirror as she applied her make-up. He seemed eager for her to finish and leave. She kissed him on the cheek and told him not to wait up for her.




Bobby reached across the table and lit Carol's cigarette. "What's wrong," he asked? "You haven't said a word all night and you hardly touched your dinner."

Carol smiled weakly as she exhaled a lungful of smoke. "I don't know. I just can't get over the feeling that something isn't right."

"Is it Jimmy? Has he been giving you problems?"

Carol took a puff from her cigarette and pondered her answer. "I can't put my finger on it Bobby. Call it mother's intuition or whatever, but something isn't right. I hate to say this, but I don't know how to relate to him. I'm raising a boy, but I know nothing about boys. It would have been so much easier if he had been born a girl. What am I saying? Do you hear me?"

"Yes, I do Carol. And I think you're telling me you need to go home early. Am I right?"

She cocked her head ever so slightly and smiled at Bobby in a flirting manner. "Would you hate me if I did?"




Bobby was the best thing that ever happened to him and his mom thought Jimmy as he floated around the living room waiving a cigarette in his hand. He believed he was gliding, but in truth he was stomping around the room like a Clydesdale. His mother's high heels were tight and difficult to balance in. He was wearing the cocktail dress that his mother had worn on her last date with Bobby. He knew he didn't fill it the way she did, but in his mind he did, and that was what mattered.

It all happened so fast. He had been caught completely off guard. It was only 9:00. His mother shouldn't be home for hours. But the sound of a key turning in the door was unmistakable. He stood there in his mother's dress, holding a lit cigarette, like a deer caught in the headlights of an oncoming car as the door opened and his mother stepped inside. Her heart fluttered. He dropped his cigarette to the ground and scurried to pick it up before it burned the carpet.

"Mom! What are you doing home"!

"I didn't feel well," she said, "so I came home. What are you doing Jimmy? Why are you wearing my clothes? You're smoking!"

"I can explain Mom," he said as he put the cigarette out. It's not what you think. I know what it must look like. I should have told you but I wanted to keep it a secret until I knew for sure."

Carol took a deep breath and tried to compose her self as she sat down and opened her purse. She needed a cigarette. "What are you talking about," she asked?

Jimmy turned bright red as he struggled for an explanation that would somehow make sense. He was caught. He was dead. He had ruined his life forever.

"I was trying to come up with a costume I could wear for Halloween."

Carol nervously lit her cigarette and inhaled a calming puff of smoke. "You're too old for trick or treat Jimmy. We agreed. Last year was supposed to be the end of it. You said you would stay home with me and give out candy."

"I know. I know," said Jimmy. "I wasn't talking about going around the neighborhood. Some kids from school are having a party and I was thinking about going."

"So why are you smoking? Is that a part of your costume too?"

Jimmy's face contorted, but he was on a roll and the lie kept building. "I was thinking about going as Cruella DeVille. You know, that woman from '101 Dalmatians'- the one that smokes and uses the holder. You know who I'm talking about, don't you?"

"Yes, I remember. It's one of your favorite movies. You weren't inhaling I hope."

His face reddened. "Of course not Mom. You know I don't smoke. It's just a part of the costume. I looked around your room to see if you had a cigarette holder, but I couldn't find one."

Carol took a deep puff from her cigarette. "Apparently that wasn't all you were looking for."

She got up off the couch and approached her son who took a step back. "It's OK," she said. "I'm not mad. I just want to get a closer look."

She put a finger on his chin and scrunched her face as she examined her son's clumsy make-up job.

Jimmy took a deep breath and relaxed. His lie was working. She believed him. Maybe he wouldn't die after all.

"You could probably pull it off with a little help. What do you say? It's still early and I'm starting to feel better. You want to come up stair? I could help you with your make-up and you could get a better idea of how you'd look in your costume."

"Naw, that's OK. I got a pretty good idea. I look pretty stupid. I don't think I'll go to that party anyway. If I'm embarrassed now, just think of how I'd feel if I really went. I'm going to take this off now."

"OK Honey. Maybe we'll talk about it again tomorrow. Just put my clothes in the dirty hamper and don't forget to wash your face. Use my baby oil."

While Jimmy took off his make-up, Carol called Bobby on the phone to let him know everything was OK. She told him there had been a situation at home but it wasn't life threatening. She asked him about his friend the psychiatrist. He gave her his friend's number.

Jimmy scrubbed hard at his face. He was boiling over with adrenalin and relief. He had dodged a big bullet tonight.




He woke up to the smell of his mom's cigarette. She was sitting on his bed, prodding his chest, and telling him to wake up. He asked what was wrong as he rubbed his eyes. "It's Saturday isn't it? I don't have school today."

He remembered the night before and scanned her face for any sign of anger but saw none.

"No silly. But we've got a big day. You don't want to spend the day in bed, do you? Go get a shower and I'll have breakfast waiting for you when you're finished."




Jimmy's hair was still wet as he walked in the kitchen. Carol had her back to him as she flipped some bacon over the stove. She turned to face him with a spatula in one hand a cigarette in the other. She told him that breakfast was almost ready and to pour him self a cup of coffee and have a seat.

She turned off the stove and set a plate of bacon and eggs in front of him and joined him at the table.

"So what's the big thing we have to do?" asked Jimmy as he nibbled a piece of bacon.

Carol inhaled deeply from her cigarette and tapped an ash. "I thought we'd work on your costume today. You know, Cruella DeVille."

Jimmy blushed. "I don't think so Mom."

"Oh come on Honey! It will be fun."

"Look Mom. I tried it last night and I know what I'd look like. There's no reason to do it again. I already told you I wasn't going to the party."

"Forget the party Jimmy. I want you to do this for me. And if you like it you can change your mind about the party."

"I don't get it," said Jimmy. "Why are you saying I should do this for you?" Carol smiled shyly and took a deep drag from her cigarette. "When I saw you last night dressed in my clothes, it made me realize that I'll never have a daughter. Don't get the wrong idea about this. I love you and I'm very proud of you. It's just I've always wished you had a sister. That's why I want you to do this. It's selfish I know. But will you do this for me?"

"It means that much to you," asked Jimmy?

"It does Honey. Will you do this for Mommy?"

Jimmy nodded his head and tried not to appear eager. This was too good to be true and he couldn't believe his good fortune.




Carol stood back from the vanity, lit a cigarette and admired her creation. "You look beautiful Honey. Come over here and look at your self in the mirror. You won't believe it!"

Jimmy got up from vanity. He'd seen his face in the mirror. He'd seen the way his mother had styled his hair. But as good as that was, he didn't put it all together until he saw himself in the full-length mirror. His mom had picked out the blue dress he was wearing as well as the sandals. They fit his feet and were much easier to walk in than the high heels.

His head spun. The feel of the slip and the pantyhose against his skin was absolutely incredible. Not only did he look like a girl, he looked years older than 13. With make-up, he could easily pass for a 17 year old or maybe even a girl in college. He tried to conceal his joy but a smile erupted across his face.

"So tell me Honey. What do you think? Do you see a boy or a girl when you look in the mirror?"

"This is so weird Mom. It's like there's no way to tell I'm really a boy."

"Almost but not quite," said Carol. "I forgot to do your nails. You'd be amazed at the difference a little polish can make. Of course I'll need to get your toes too. Sit back down. This will only take a minute."

Jimmy sat back down and watched his mom as she went to work on his fingers and toes. She was right. It did make a difference.

Carol was excited. Not only was it fun to play with Jimmy as if he was her daughter but she was also enjoying her son's happiness. It had been years since she'd seen her son so relaxed and happy.

She didn't stop with the make-up. It was one thing to make her son look like a girl. It was another to get him to loosen up and talk and walk as a girl. "Do it like this," she said. "Now walk like this." It went on for hours. Jimmy found himself wishing it could go on forever. He'd never felt this much at ease with his mom before. He loved her and he knew she loved him back, but they had never shared a moment like this. He had never felt as close to her as he did now.

His sense of joy and security disintegrated when his mother picked out a spare purse, handed it to him and told him they were going to the mall.

"What for?" he asked. "I thought we were just going to do this here. I can't go out looking like this. What if someone sees me?"

"Give me a break Jimmy. I'm your mother and I don't recognize you. As far as anyone will know, you're just another very pretty teenage girl. I'll tell you what. If we see anyone we know, I'll tell them you're my niece. I'll call you Katie. How's that sound? Do you like that name? That's the name I chose for you when I was pregnant. I would have named you Katie if you had been born a girl."

"Yeah, I guess that's OK. Do I look like a Katie?"

"To me you do. Do you feel like a Katie?"

Jimmy looked in the mirror and smiled. "Yeah, I guess I do."




Somewhere between the house and the mall, Jimmy lost his nerve. He had been blinded by the excitement of wearing his mother's clothes. But fear had awakened his reason. And the smell of his mother's cigarette smoke reminded him that he hadn't smoked in over a day.

He told his mother that he had changed his mind. She would have none of it. They parked at the front entrance. Jimmy spotted three boys he knew from school. He tried to look away as they walked past the boys. He felt the boys' eyes but no one shouted his name. He breathed a deep breath sigh of relief as the door closed behind him and his mother. Maybe this would work out after all.

Their first stop was at a lingerie store called Sylvia's. He'd seen it many times before but never from the inside. He followed his mom to the far corner of the store where the breast forms were on display. She looked at him and back at the forms before choosing a set that would give him a 'C' cup. He was thankful that his mom carried them and didn't ask him to do it. She then went about picking out panties, bras and slips. She had a handful of under garments when she let out a gasp.

He followed her eyes thinking she'd seen someone they knew. She wasn't looking at a person. Her eyes were fixed on the sexiest nightgown he'd ever seen. It was long like the red one his mother wore but this one was powder blue. His heart raced as she took it off the hanger and draped it over her arm. He didn't say a word as she went to the sales desk and paid for the purchases with a credit card. She didn't say she had bought the things for him but he could only assume.

After leaving the store, Carol said she needed a cigarette, so they took a seat on a bench. She told him they had another stop to make. She wanted to get him some different to wear. After all, he wasn't anyone's mother. He needed something younger looking.

He tried to talk her out of it as they approached the department store. He told her it wasn't necessary. It was just a Halloween party and he probably wouldn't even go.

She told him not to worry about it. She impressed upon him that he was doing her a favor by letting her pretend to have a daughter. He followed her into the store.

They went straight to the junior department. Jimmy watched as his mother stalked the racks picking skirts, belts, blouses and dresses. He spent the next hour trying them on along with breast forms she purchased at Sylvia's. When it was all said, done and paid for, Jimmy walked out wearing some of the purchases and carrying the rest in bags along with his mother's old clothes. He was dressed as if had just walked off the set a Mandy Moore video.

As he carried the bags through the mall, he complained that she had spent too much. She told him not to worry about it and to quit trying to spoil her fun. She noticed the jiggle in his chest as he walked and asked how the breast forms felt. Jimmy blushed and told her that they were neat and felt real. They were so different than the socks he'd stuffed her bra with.

He was so busy talking and enjoying him self that he didn't notice when his mother turned and walked into another shop. They were inside the "Tinder Box". It was a tobacco shop that specialized in cigars, pipe tobacco, cigarettes, and all kinds of smoking accessories.

A man who appeared to be in his early fifties approached them and asked if he could be of assistance.

"I hope so," said Carol. "This is my daughter Katie. She's recently taken up smoking. As much as her decision pains me, I respect and understand her feelings. I was her age once and I remember what a milestone it was when my mother gave me permission to smoke."

The man looked at Carol and then at Katie and nodded as he scratched his beard. "So what did you have in mind," he asked?

"Well, what do you have in the way of cigarette holders?" asked Carol.

The man gestured to the display the case as he walked around the counter. He took out a black holder that was medium in length and accented with pearl.

"It's beautiful," said Carol as she admired it and then handed it to Jimmy.

The man also placed a gold lady's lighter on the counter. Jimmy squeezed his thighs together as he tried to hide his erection.

"These are wonderful," said Carol. "They'll do quite nicely. Also, may we trouble you for a carton of cigarettes?"

She turned to Jimmy and asked, "You still smoke Virginia Slims, don't you Katie?"

Jimmy smiled weakly as she squeaked out a "Yes Mom."

The man behind the counter reached behind him and pulled a carton of Virginia Slims. Carol handed him her credit card and opened the carton of cigarettes while the man rang up her purchases.

She handed Jimmy a pack. "Here Katie. Put these and the lighter in your purse. I'm starved. How about you?"




They ordered salads and Carol removed her cigarettes from her purse and lit one. She reached in a shopping bag and pulled out the cigarette holder. "Go ahead Honey. Show me your best Cruela DeVille imitation."

Jimmy blushed as he took the cigarette holder from his mom and loaded a cigarette in the holder's barrel. He was dying for a smoke. He knew his mother had bought the holder as prop for his costume. She had no idea he was really addicted. As far as she was concerned this was just a little joke, but it felt like a matter of life and death as he scrambled to light the cigarette. He couldn't help but feel he was getting away with something right under her nose.

Carol watched as Jimmy lit the cigarette and inhaled a deep puff. He didn't cough- quite the opposite as a matter of fact. Relief flooded his face as the smoke entered his lungs.

"Do I look like Cruella DeVille," asked Jimmy?

Carol scrunched her face as she studied him. "Not really. You look to pretty to be Cruella. And the holder doesn't go with your clothes. Lose the holder and try it with just the cigarette."

"But Cruella always uses a holder," argued Jimmy.

"I know," said Carol. "I just want to see what you'd look like without the holder. OK?"

Jimmy took a deep breath and sighed as he twisted the cigarette loose from the barrel and placed the holder on the table. He realized his mom had put him in an awkward position. The only reason she was letting him smoke was because he was trying to look like Cruella DeVille. What was he supposed to do now-- smoke it?

Carol looked at her son holding the cigarette and smiled. "Aren't you going to take another puff," she asked?

Paranoia overtook him. As much as he needed to smoke, he couldn't risk getting caught. He felt as if his mother was setting him up. "I don't really smoke. You know that."

She looked at him knowingly and said, "Jimmy doesn't smoke, but I think Katie does."

Jimmy reached across the table and tapped his cigarette over the ashtray. "What do you mean," he asked?

"What I mean," said Carol, "is that I think my lovely young daughter is addicted to cigarettes. I saw the way you inhaled when you lit up. You've been doing this for quite a while, haven't you Katie?"

Jimmy knew the game was up or at least he thought it was. He put the cigarette to his coated lips and took a deep drag. He inhaled and felt some relief although he was scared to death of what his mother would do to him.

"Why are you doing this," he asked? "If you knew I smoked, why did you make me get all dressed up in these clothes and go through this?" Carol put her cigarette out and lit another one. "I did it so I would know for sure. This is about a lot more than smoking Honey and you know that."

"I don't know what you're talking about. You're right. I've been smoking. I'm sorry and I'll quit. I'll never do it again. I promise."

"It's not that easy Katie. If it were I would have quit a long time ago. Believe me. I know. I started smoking when I was your age too. And I started for the same reason you did- to attract boys, and then I got addicted. The same thing happened to you. You can't quit any more than I can. It's nothing to be ashamed of Honey. A lot of girls start smoking when they're your age. Why should you be any different? You look very feminine and grown-up with your cigarette. See how the boys are looking at you?"

Jimmy scanned the restaurant. His mom was right. They were looking at him, and he liked the way it made him feel. He put out his cigarette and lit another one.

"What are you trying to say Mom? Are you telling me I'm gay?

"Not at all Honey. You're not a guy that likes guys. You're a woman in a boy's body that likes guys. You should have been born a girl, but you weren't. But that doesn't mean we can't make it right. I'm going to make an appointment for you to see a doctor on Monday. And I want you to be completely honest with him and with your self. Will you do that for me Katie? Will you?"

"Yes mom."


Just a note from the editor: Slim V. emailed me that there is more to this story, hopefully to be appearing soon. :)

 



Cigarettes Are a Girl's Best Friend -2-

Author: 

  • Slim V.

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Transgender
  • Crossdressing
  • Posted by author(s)
  • Serial Chapter
Cigarettes Are A Girl's Best Friend

by slimv

PART 2

Jimmy felt queasy with excitement. He'd never experienced this kind of anxiety before. He looked at his mom and glanced back at the cigarette between his fingers. For crying out loud! He was 13 years old. He was sitting in a public restaurant with his mom- wearing girl's clothes and smoking Virginia Slims! This was insane. He was insane. After all, hadn't he just promised her he'd see a psychiatrist?

"Can we go home now Mom? I think I'm feeling kind of sick."

Carol crushed out her cigarette and signed the credit card receipt. "I guess you've had a lot of excitement for one day."

A very confused boy named Jimmy Higgins, who was masquerading as a girl named Katy, picked up his bags of wonderful new clothes and followed his mother out of the restaurant, and through the mall.

They were riding down the escalator as a pair of teenage boys was riding up. Jimmy didn't recognize them. They were older and in high school. They were shoving each other but never took their eyes off him. They were obviously trying to get his attention. If they only knew, he thought. Carol noticed them too. She watched the boys as they flirted with her new daughter. She watched as Katie looked away from the boys. She was clearly embarrassed by the attention

Katie turned around and looked up as her feet hit the floor. The goofy boys were still following her with their eyes. One of them even waved. She looked away as heat rose in her face.

"They thought you were cute," said Carol.

"I don't think so," said Katie. "They weren't looking at me. They must have seen something else."

"No Katie. It was you they saw and they liked what they saw. I thought they were cute. Didn't you?"

"Come on Mom. They're guys. I'm a boy. How can you ask if I think they're cute?"

*****

The ride back home was fairly quiet. Katie stared out the window as his mother drove. His mom was smoking. He wanted one too. He fiddled with his purse but couldn't bring him self to take out the pack of Virginia Slims.

"You know," said Carol, "you can have a cigarette if you like. I did give you my permission."

"Really" asked Katie?

"Yes Honey. Really. I'm not kidding. You're not going to get in trouble. And I do understand what you're going through. I remember how awkward I felt when I first started smoking in front of my mother. But I got used to it and so will you. It's nothing to be ashamed of. I know it's something you need to do now. And I suspect it's something you want to do as well. It's kind of like the clothes you're wearing. You've been raised as a boy, but there's a girl inside that's been trying to get out for years. She needs those clothes you're wearing. And she wants them. Am I right Katie?"

"Yeah, I guess so. It's just so weird to think about. I know how I feel but I don't know how to say it."

"Are you happy?"

Katie turned in his seat and made eye contact with his mother. "This has been like the best day of my life. It's like I don't want it to ever end but at the same time I'm afraid of it."

"I know you are. That's why I want you to talk to the doctor. Bobby says the doctor is really nice and I think you'll like her a lot. He says she's real easy to talk to."

Katie thanked his mom and took the pack of Virginia Slims from his purse. It was still a shock to see the pack in his hand. He took a cigarette out and returned the pack to his purse, holding it between his lips as he searched for the lighter in his purse.

They were pulling up to a traffic light as Katie lit his cigarette. He breathed the smoke in and nervously exhaled toward her window. There was a group of guys in the car next to them. They were looking at him, watching him smoke. But they weren't looking at him. They were looking at her. Katie took a deep drag from the cigarette and exhaled toward the carload of boys as seductively as he could. He saw their eyes pop. He felt their desire and he basked in it within the safety of his mother's car.

Carol laughed and said, "Young lady! I do believe you're flirting."

He turned to his mom and vehemently denied her accusation. "I wasn't flirting. I was just smoking."

She gave her daughter a knowing nod and smiled.

*****

Dr. Laura Doyle listened as Carol told her about Katie. She liked Carol and quickly saw why her friend Bobby liked her. Carol was calm, collected and open minded. The vast majority of her patient's parents were not receptive to the underlying needs of their gender-disoriented children. She commended Carol on her compassion.

"I'll be as honest with you as you've been with me Mrs. Higgins. After meeting Katie and talking with you, I feel confident in diagnosing your son as having a severe gender identity crisis. I wish more parents could be as sensitive to their children's needs as you've been with Katie."

"So you agree with me? You think I should do every thing possible to help Jimmy become Katie?"

"Absolutely Mrs. Higgins. I've worked with many young boys like Jimmy. He may have some doubts but I don't. Your son is female and the sooner he realizes this, the happier he will be. I admit it's usually the parents rather than the patients who have trouble coming to this conclusion. Jimmy is confused by both his sexuality and his gender. He's afraid he's gay and of course you and I know this isn't the case. Jimmy is as much of a woman as you or I. The only obstacle between her and happiness is his penis."

"So you think Jimmy is a candidate for gender reassignment surgery?"

"There's no doubt in my mind Mrs. Higgins. He needs to begin hormone therapy right away. The hormones will help Katie's breasts grow, but expediency is a priority. I'd like to schedule breast implants for Katie tomorrow if that's OK with you."

"Of course it is Dr. Doyle. What about the size? Will they be big or small? Will Katie need to wait a year before he can have the reassignment surgery? I'm sorry about rambling, but wow, this is all so incredible."

"That's OK Mrs. Higgins. Your excitement is completely understandable. As far as breast size is concerned, the decision should be left completely up to Katie. Take her home and go to a website called Southern Charms. Let him look at the girls and he'll be able to decide what size breasts are right for him. Let him choose as large or as small as he likes. As far as the surgery is concerned, it's completely up to you and Katie. I realize it's standard procedure to wait, but I don't recommend it in Katie's case because he's a heterosexual. Time wouldn't be an issue if he were gay. But time is a luxury he doesn't have. He's at the age where he needs to start forming healthy relationships with members of the opposite sex. The sooner he becomes a woman, the sooner she'll be able to do that."

"When will he be able to have the surgery?"

"Even on the fast track, it will probably take at least a month. In the mean time, you need to encourage him to date. I realize he'll feel awkward about dating boys but it will make his transition much smoother, so please push him Mrs. Higgins- even if he resists. It's for his own good."

"I'm sure he'll fight me on that. He'll also be upset about the surgery. Should I tell him or would it be best coming from you?"

"Believe me Mrs. Higgins. Jimmy will be very excited about this. Remember, he wants to be a woman. What he says and what he really feels isn't always the same thing. Tell him about the breast implants but keep the surgery under your hat until the time nears. Even though it's what he wants, it would be best not to overwhelm him."

Dr. Doyle leaned forward in her chair and fixed her eyes on Carol's. "The most important thing you can do for Katie right now is to boost his confidence. He needs to feel desirable and attractive as a woman. Dating will help build his self esteem but he needs to feel good about him self in order for his dates to be successful."

"He needs plenty of reassurance from you. Use compliments. Tell him how nice he looks. It's very important to avoid saying or doing any thing that romances the notion of his maleness. I know he was dressed as a boy today because he came from school, but does he still have all his boy clothes?"

"Well yes," said Carol. "I haven't had enough time to replace his wardrobe. I didn't realize how serious this was."

"It's very serious Mrs. Higgins. And because Katie's transformation is on the fast track, it's crucial to eliminate his male side as quickly as possible. That means a new wardrobe. It also means changing his room. There's another thing. I saw a pack of Marlboros in his shirt pocket."

"You must think I'm an awful parent for letting him, I mean her smoke. But he's been doing it for a while and I think he's addicted. He's also got this thing about smoking. He thinks it's sexy. You should have seen her when I let her smoke in the restaurant Saturday. All the boys, even the men, were looking at him."

"Mrs. Higgins, I don't think you're a terrible parent. You're wonderful. My job would be so much easier if more of my patient's parents were as caring as you. It's not the smoking that concerns me. It's the brand. Marlboro is such a masculine brand. It would be so much better if you encouraged him to smoke something more feminine. Even something like Benson & Hedges would be better than Marlboros."

"I did buy her Virginia Slims. He just wanted the Marlboro's for when he wears his boy's clothes."

Dr. Doyle raised her brow and lowered her eyes on Carol.

"Well at the time, I didn't expect this to happen so fast. He still has three months of school left. I can't send him to school dressed like Katie can I?"

"If you love your daughter, and if you want what's best for her, you'll home school her for the rest of the year. You'll also need to legally change her name to Katie. I can give you the name of a lawyer who can help you with this. It's imperative that you sell your home and move to another school district so Katie can start high school as a girl."

"I can do that," said Carol. "And it's OK to let her smoke? Should I place any limits on her?"

"No limits Mrs. Higgins. You gave Katie permission to become an adult when you gave her permission to smoke. Cigarettes are a symbol of her adult status. As a matter of fact, you should encourage Katie to smoke. After talking with him today, I discovered he has made a strong association between smoking and femininity. He has a fetish for smoking. If he didn't have issues with gender, he would focus his fetish on being with women that smoke. But because he feels he is a woman, he needs to harness that fetish to his advantage. I want him to feel sexy when he smokes. You're a smoker Mrs. Higgins. You know what I'm talking about. It's not enough that you gave Katie a pack of cigarettes and a lighter. As her mother, you need to teach your daughter how to use them. Do you understand? Do you have any questions?"

"No Dr. Doyle. You've been very helpful. Katie and I appreciate everything you've done for us and I'll follow your advice to the letter."

"Good," said Dr. Doyle as she reclined in her chair. "After Katie gets breast implants, I want you to focus on getting him to date. Don't take no for an answer. His happiness depends on it."

*****

"Well what did she say Mom. You two were in there for almost two hours. Does she think I'm sick? God, I feel like I'm going out of my mind."

"She said a lot of things Jimmy," said Carol as she backed the car out of the space and pulled a pack of cigarettes from her purse.

Jimmy followed his mother's example and took the pack of Marlboros from his shirt pocket. Before he could extract a cigarette from the pack, his mother took them from him.

"What's wrong," said Jimmy. "I thought you said I could smoke. Did Dr. Doyle say not to let me?"

"No, she didn't," said Carol. "She said that from now on you were to smoke like a lady and that means no more Marlboros. Here, have one of my Virginia Slims. Their your regular brand anyway."

"But Mom, I'm wearing boys clothes. What if someone sees me?"

"They won't," said Carol. "You're in the car. Besides, I don't want to see you in boy's clothes again. When we get home you need to change into your girl's clothes. Then you can help me clean out your closet. We'll give all your boy's clothes to the Salvation Army. Oh we have so much to do. We have to redo your entire room. You're ready for a change aren't you?"

"What did she say Mom? Are you going to tell me?"

"She told me what I already told you. She just confirmed what we already knew. Simply put, you should have been born a girl and we're going to fix that. You have an appointment tomorrow to have breast implants."

Jimmy's jaw hit his chest. "Breast implants! I can't do that. Everyone will know. Mom. I like dressing in your clothes. I admit it. I love it, but I can't get real breasts."

"Why not," asked Carol?

"Well, you know. I'm a boy. Boys don't have breasts. I got a penis and everything. Everyone will make fun of me."

"What if no one knew? How would you feel about it then?"

"Come on Mom. I think people will know. Guys with breasts kind of stand out. I think my friends will notice."

"I'm serious Jimmy. And I want you to be serious too. I want you to think about this and I want you to tell me how you would feel about the breast implants if no one ever knew. If we do this, we'll do it right. We'll change your name legally to Katie. I'll home school you until you start high school next year. We'll sell the house and move to a place where no one knows you. You'll have a fresh start. Think about it. Today could be the last day of your life as Jimmy if it's what you want. You don't have to tell me now. Wait until we get home. There are some things I want to show you on the computer. You can tell me what you think afterwards."

Jimmy listened to what his mother said. The seriousness of the decision he was about to make sank in. He put the Virginia Slim between his lips and lit it. He savored the feeling of the smoke in his lungs as he pondered his mother's words. He thought about the last two days he had spent dressed as Katie. He thought about how much better people treated him when he was dressed as her. Even his mother treated him better when he looked like a girl.

He'd been to the mall hundreds of times but had always been invisible until last weekend. People noticed Katie because she was beautiful and glamorous. He thought of how comfortable he had felt smoking at the mall while dressed as a girl. He could never do that as a boy. He had carried the Marlboros along with him all day without getting up the courage to have one in public. People respected Katie. They didn't respect Jimmy. The idea of spending the rest of his life as Katie appealed to him. He sat back in the car, looked out the window and took another puff from the Virginia Slim.

*****

He was glad to get out of his boy's clothes when they got home. Sitting at the computer with his mom as she clicked through a porn site was weird. It bothered him but it didn't stop him from fondling his breast forms. Until today, their computer had always had a porn lock. He knew sites like this existed but he had never seen one until now. His mother told him to look at the girl's breasts and that's exactly what he did. He looked and looked. Some were kind of homely, but others defied description. Many of them were smoking! He envied them.

"Do you see any thing you like," asked Carol? "Dr. Doyle said the surgeon could make you breasts like any of these. All you have to is to pick a girl you like. Their breast sizes are listed in their bios. It's kind of like window shopping."

"Go back to Claudia," said Katie. "I want to see her again."

Carol gave him a rather disgusted look as she clicked on Claudia's picture. "I don't think Dr. Doyle had 36 G in mind when she said to choose your breast size."

Katie's eyes grew big as the thumbnails presented them selves on screen. "Click that one," he said.

Carol clicked on the thumbnail and Claudia exposed her self to them on the screen. She looked to be in her early 20's and was busting out of her silky red negligee. She was sprawled on a bed smoking a cigarette, giving them her best come hither look. "They're very big. Don't you think? She probably has back problems. Have you thought about that Honey? They wouldn't be light."

"Mom, I'd give any thing to look like her. She's beautiful. Besides, breast size is just a number, right?"

Carol clicked on the printer icon and the inkjet came to life.

*****

Dr. Brown smiled when Katie showed him the inkjet photograph of Claudia. "Are you sure," he asked?

Katie shook his head yes as Carol winced.

The last thing Katie remembered before the lights went out was an attractive nurse ramming a sharp needle in his ass while his mom held his hand.

His mother was still holding his hand when he woke up. "Is it done? Do I have boobs?"

"See for your self," said Dr. Brown as he held a mirror for Katie to look at.

"Oh my God," said Katie. "They're huge. I didn't know they'd be this big." He placed his hands on the huge melons and tried to give them a squeeze. "Ouch," he screamed!

"They'll be tender for a few days," said Dr. Brown.

Katie smiled at the doctor and thanked him. "What do you think Mom?"

"I think you're going to need some bigger clothes," said Carol.

Cigarettes Are a Girl's Best Friend -3-

Author: 

  • Slim V.

Audience Rating: 

  • Restricted Audience (r)

Taxonomy upgrade extras: 

  • Transitioning
  • Crossdressing
  • Posted by author(s)
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  • Contests, Deals, Bets or Dares
Cigarettes Are A Girl's Best Friend

by slimv

Part 3

His mother was true to her word. As Jimmy's chest recovered from Dr. Brown's scalpel, Carol made some calls. The lawyer referred to her by Dr. Doyle created a new identity for Katie. He even helped Carol forge school transcripts so Katie could start high school at Gilmore in the fall.

Katie's new wardrobe had become worthy of his new melon sized breasts and his room had undergone a transformation of it's own. The walls, once stark white and covered with posters of quarterbacks yielded to a feminine shade of pink and posters of Brittney Spears. He didn't shed a tear as he packed up the remnants of Jimmy's life for the Salvation Army. He was caught up in the excitement of his fantasy turned real.

He spent hours in front of the mirror experimenting with his new make-up kit. He would lie under the canopy of his frilly bed turning the pages of 'Seventeen Magazine' and smoking Virginia Slims.

Dr. Brown had been right about his breasts being tender. The first day after the surgery had been miserable. The pain would have been unbearable if not for the ecstasy of his imagination. He had fallen in love with the idea of looking like a woman. The permanence and reality of his transition were overshadowed by the immediate thrill of the change. The mirror didn't lie. He looked fabulous! But underneath the skirt he was still a boy and still thought of himself as one.

Katie clenched the cigarette between her teeth and ran her fingers across her massive breasts. Unbelievable he thought as he pinched the nipples between his fingers. He hadn't expected them to be so sensitive and reveled in the feeling. He was on his way to becoming his own dream girl.

Nothing about his transition seemed real. It was as if he expected to wake up from a glorious dream or worse- to get caught indulging in a full-blown perversion. He hadn't closed the door and his mother's voice sounded in his ears.

"Are you checking for tenderness," asked Carol? "Or are you just feeling your self up?"

Startled by his mother's presence, he jerked his hands from under his blouse and put the cigarette out. He blushed when he looked at her. "I guess you caught me," he said.

"That's OK Honey. You weren't doing any thing wrong. You're just getting oriented to your new body. I bet you never even heard of silicone until a couple days ago. Dr. Brown did a wonderful job. You should be very proud. I know I'm envious."

"Really Mom? You think they look good on me?"

"I do," she said as she sat down on the bed beside him. She smiled at her new daughter and asked, "So tell me, why did you put your cigarette out when I came in. You hardly smoked it. That's such a waste. You know how expensive they are."

Katie shrugged and blushed. "I don't know."

Carol nodded and sighed. "I wish you wouldn't be ashamed about smoking in front of me. Do you think it makes you a bad person?"

Katie shrugged again.

Carol looked past the breasts, the clothes and the make-up. She saw an insecure boy who lacked confidence in her self. She knew he was in need of a heart to heart talk.

She pointed to the pack of Virginia Slims on Katie's quilt. "Mind if I have one? I left mine in the kitchen."

She took her daughter's silence as a yes and picked up the pack, removed two cigarettes, lit one for her self and handed the other to Katie.

"I don't understand what's wrong," said Carol. "I thought you wanted to smoke."

"It's hard to explain," he said as he took a small drag.

"This is about your fetish, isn't it," asked Carol.

The crimson color returned to his cheeks. "I don't know what you're talking about."

"I think you do, but you're too ashamed to talk about it. Dr. Doyle told me all about it. You think girls are pretty when they smoke, don't you?"

"Yeah, I guess," said Katie. He sighed and trimmed his ash over the ashtray on his nightstand. "I guess that makes me pervert- that and the clothes and the breasts."

"No Honey. You're not a pervert, but you're confused. So much has happened so fast- maybe too fast. But Dr. Doyle says it's better this way. She says the sooner you get used to thinking of your self as a woman the happier you'll be."

"Well that's just it," said Katie. "I don't think of my self as a woman. I'm still a guy. I just like dressing up as a girl."

"So you're saying that wearing girl's clothes, having breasts and smoking is like entertainment for your brain. It's just a game for you. It's not real."

He looked at her as if she'd read his mind. "Yes," he whispered. "Exactly. This feels like a dream, like I'm doing something wrong. I keep thinking you're going to yell at me and call me a queer or scream at me for smoking. It doesn't feel right. It feels good, but I don't deserve to feel this good. I'm not a girl Mom. I'm a boy. You know it and I know it." He felt a tear forming in the corner of his eye and looked away so she wouldn't see him cry.

She laid a gentle hand on his shoulder. "It's the hormones Honey. They're making you emotional. That's why you're crying. It's OK. I know it feels strange but it's normal."

"Nothing about me is normal Mom. I'm a freak."

Carol lifted the cigarette to her lips and hallowed her cheeks as she searched for the words that would comfort her daughter. "This must be so hard," she said. "I was born a girl. I had my entire life to prepare myself for womanhood. You've only had a few days. Your head must be so jumbled with boy thoughts. You're looking at this and feeling as if you're life is happening to a boy. Am I right?"

Katie nodded, sniffed, dried his eyes, and took a puff from his cigarette.

Carol handed him a tissue. "Your mascara is running. You'll have to do your make-up again before we go out."

"We're going out? Where?"

"We're meeting Bobby and one of his friends from church at Antonio's. You like Antonio's. I thought maybe you'd like the chance to show off your new breasts in public. I know I would if they were mine?"

"God Mom. I don't want Bobby to see me like this. He'll laugh. And I sure don't want to his friend to see me."

"Bobby won't laugh Honey. Who do you think gave me Dr. Doyle's name? He's fine with this and he wants you to be happy, just like I do. And as far as his friend goes, so what? He'll never know. He just thinks he's meeting his buddy's girlfriend and her daughter."

"I'm not sure if I did the right thing Mom. I know I'm weird but being a girl is a lot different than just dressing like one. I've never been like a girl for more than a couple hours and now it's been like five days non-stop."

"You need to quit thinking of your self as being 'like a girl' Katie. You are a girl, and very soon you'll be a woman." She leaned in and hugged her new daughter. "I'm so proud of you Katie."

Tears welled in his eyes as he caved under his mother's embrace. "How can you say that Mom? How can you say you're proud of me when I'm such a freak? Look at me. I'm a boy with boobs and they're huge boobs. I'm wearing make-up and smoking cigarettes. How can you say you're proud of me?"

"I'm proud of you because you're my daughter. The cigarettes, the boobs, the make-up and the clothes are all a part of being a woman. Any mother would be pleased and proud to have a daughter like you Katie. Believe me. I know because I've wanted a daughter like you my entire life. I want you to be as happy as you've made me. Will you let me help you to be happy?"

Carol gasped as her chest collapsed under the pressure of her daughter's hug. Katie looked liked a girl but was still as strong as a boy. It was her turn to cry when she heard the words, "I love you Mommy," whispered in her ear.

*****

Katie closed his car door and waited for his mother to come around so they could walk up to restaurant side by side. He finished his cigarette and crushed it on the pavement beneath his sandal. "How do I look," he asked? "Are you sure this purse goes with my dress?"

Carol shook her head. "I told you a hundred times before we left. You look beautiful Katie. You're absolutely stunning. The purse is black and goes with everything. Besides, with that cleavage of yours, you could be carrying a greased pig and no one would notice. Now quit worrying about what you look like and let's have a good time."

Katie stood behind his mother as she checked their reservations with the hostess.

"Mr. Rogers hasn't arrived yet but we can seat you. Follow me."

Carol and Katie followed the hostess as she led them to a booth in the smoking section. "If you'll be seated, I'll have the waiter take your drink order and I'll show Mr. Rogers and his guest to your table as soon as they arrive."

Carol thanked the hostess and took a seat.

"Did you see the way those men in the front were looking at you when we walked in?" asked Carol, as she removed a pack of Virginia Slims and a lighter from her purse.

Katie blushed. "No. I didn't see that and I wouldn't have wanted to either."

"Get used to it Honey. You're a beautiful woman, and how should I say this politely? Your figure is especially striking."

"I'm so nervous," said Katie. "You don't know how weird this is for me. What if they laugh at me?"

"He's not going to laugh Honey. Have a cigarette and calm down."

"What about Bobby?"

"It's OK Sweetheart. He knows you smoke. Go ahead and have a cigarette. It will make you feel better. Besides, don't you want to put on a show for the men?"

Katie removed the cigarettes and lighter from her purse and lit one. His Mom was right. The smoke went a long way toward soothing his pulsating nerves. "What do you mean about putting on a show," he asked?

Carol gave him a look of surprise. "Are you serious? You should know better than anyone. Lots of guys like to see pretty girls smoke. They think it's sexy. Isn't that why you started?"

Katie was puzzled by his mother's question. "I don't know. I don't think I ever thought about it like that. Are you saying I'm not the only the only guy that likes to watch girls smoke?"

Carol laughed. "Of course not Honey. But remember? You're not a guy. The shoe is on the other foot now, so to speak. You're the girl who smokes and guys look at you now. Can't you see? They're looking at you now."

"You mean Bobby likes it when you smoke?"

"Duh," said his mother, sounding like a teen rather than an adult mother.

"I don't get it," said Bobby. "He doesn't even smoke. I thought he was some kind of health nut that ran 50 miles a day and ate trees for breakfast. Doesn't it bother him when he kisses you?"

"Don't believe every thing you see on TV. Sure, smoking bothers some guys, but lots of men find it attractive. Now I want you to do every thing the way we talked about. Remember to keep your cigarette in front of you. It's important to emphasize how you hold it. By holding the cigarette by the filter, it makes your fingers look longer and accentuates your manicure."

"Like this?" asked Katie as he demonstrated his technique.

"Yes. That's perfect!"

Katie took a deep puff from his cigarette, being careful to do as he was taught. "Wow," he said. "This sure is weird. I didn't know girls had so much to learn. I always thought it just came natural to them. I didn't think they really practiced things."

"Well," said Carol. "A lot of things are instinctual. But then again, a lot of things are learned over time which is why you've got some catching up to do."

"Don't look now," said Katie, "But here comes Bobby and his church friend. Are you sure it's OK for me to smoke here? What if it bothers Bobby's friend? I thought church people were kind of weird about things like smoking and drinking."

"I guess we'll find out, won't we?"

Bobby leaned over the table and kissed Carol on the cheek. "Hey girls," he said. "This is my friend I was telling you about." He turned to his companion and said, "George, this is my girlfriend Carol Higgins and her daughter Katie. Girls, this is George Hathaway."

George extended his hand to both ladies and greeted them by name. Bobby sat next to Carol and George sat beside Katie who couldn't help but notice George's eyes following his breasts as he pulled out his chair.

Carol took a deep drag from her cigarette. She smiled when she did so, holding the smoke in her lungs longer than usual before exhaling gracefully toward the ceiling. "I hope our cigarettes aren't troubling you George. Katie and I can put them out if our smoke bothers you."

George laughed and told them that if smoking bothered him, he would have divorced his wife years ago. He told them about his family. He and his wife had a 16-year-old son named Brent who would be a junior next year at Gilmore High School.

"What a coincidence," exclaimed Carol! "Katie's going to Gilmore next year."

"Oh really," asked George? "What subject do you teach? Maybe Brent will be in one of your classes."

Katie blushed. "I'm not a teacher. I'm only 13. I'll be a freshman next year."

George choked on his water. "You're kidding? You're only 13? She's kidding isn't she Bobby?"

It was Bobby's turn to laugh. "She's only 13 George. Girls mature much faster these days."

"You're telling me," said George! "I'm sorry. I don't mean to seem so surprised. But you look much older Katie. I guess the cigarette threw me. You smoke like such an adult. Have you had the habit long?"

When Katie didn't respond immediately, Carol came to his rescue. "The little devil has been sneaking my cigarettes since she was 11. I tried every thing to get her to quit, but girls will be girls. They're in such a hurry to grow up and be women. What can I say, like mother, like daughter," she giggled.

*****

Carol was bursting with silent pride as she watched her daughter blossom during dinner. The shy longhaired boy she had once caught wearing her clothes and sneaking cigarettes was gone. In his place sat Katie, beautiful, elegant, sophisticated and mature.

Katie had passed his first test.

"Excuse me," said George. I probably shouldn't ask, but do you have a boyfriend?"

Katie blushed. Why would a man who was old enough to be his father ask if he had a boyfriend? Was he coming on to him? He was married. He was supposed to be a Christian. Didn't he hear Bobby tell him he was only 13? Just the idea of George or any other guy being attracted to him made him sick to his stomach. But it wouldn't be polite not to answer and Katie knew this.

"No, but I don't think my mom would let me go out with you either. I'm only 13."

It was George's turn to blush. "I'm so sorry," he said. "You must think I'm pervert. I wasn't asking for me. I was asking for my son, Brent."

George took out his wallet and showed Katie a picture of Brent as Katie smiled politely. His mother hadn't taught him how to handle awkward situations and he was winging it. After all, this was Bobby's friend and his mother would be remiss if he offended this guy.

Carol reached across the table for George's wallet. "Oh I just love pictures. Let me have a look."

Thank God, thought Katie. His mother would get him out of this. There was no way she'd let him go out on a date. He'd asked her before, back in his boy days and she had always said no, saying he wasn't old enough to date girls. Well if he was too young to date girls then he was definitely too young to date boys.

"He's a hunk," exclaimed Carol! "Don't you think Brent is cute Katie?"

Katie took a puff of her cigarette and exhaled. "Yeah Mom, he's real cute. But he wouldn't like me. He looks like such an athlete and Mr. Hathaway said he plays football and wrestles. He'd hate me cause I smoke."

"Nonsense," said George. "If any guy didn't want to date you because you smoke then they should have their head examined. If it's OK with your mother, and you of course, why don't the two of you go to Six Flags tomorrow."

Before Katie could say no, his mother told George that it was a wonderful idea. As Katie struggled to keep his food down, his mother and George decided on a time. George was so happy, he insisted on paying for the entire meal. He then told them that he needed to cut out early and apologized.

Bobby followed George with his eyes as he left the restaurant. He then turned to Carol. Katie noticed the perplexed look on his face.

"What in the hell were you thinking Carol? How could you set up Jimmy on a date with my friend's son? Have you gone out of your mind?"

Thankfully a voice of reason had penetrated the madness of his mother's world.

"I didn't set Jimmy up on a date," said Carol. "I set up Katie. I think she and Brent will have a marvelous time."

"But what if he finds out I'm a boy. I can't do this Mom. He'll find out the truth and when he does, he'll beat me to a bloody pulp. Why are you doing this to me? Brent is huge. He'll kill me!"

"Not only that," added Bobby. "George and his family go to my church. I'll be ruined. I'll never be able to show my face again."

Unalarmed by their stress, Carol lit a cigarette and calmly exhaled a stream of smoke. "Well I guess Katie had better be convincing then." She looked at Katie and laid her hand across his. "Don't be scared Honey. This is exactly what you need. Dr. Doyle said so."

"But Mom, I don't want to go out with Brent or any other guy. I thought you understood that."

Carol smiled and gave her daughter an understanding look. "Dr. Doyle said you'd be apprehensive about dating. But she assured me it would be in your best interest and I agree with her. This is for your own good Katie. Like it or not, you're going out with Brent tomorrow.

*****

Katie lay on his bed and stared into the darkness. His mother had lost it. She had turned his thing for women's clothes into a death wish. He had argued with her on the way home from the restaurant but she had refused to budge.

The rules were simple. Pretend to have a good time and don't let Brent discover the truth. Katie cried him self to sleep.

*****

She stood in front of his mom with his hair tied back in ponytail. He was wearing a pair of cut-off jeans and a red halter. For the first time since getting his implants, he felt like an exposed milk cow. "Can't I wear something that doesn't show so much skin," he asked?

"What? And have a heat stroke? It's going to be close to 90 degrees today. Besides you look great. Put this on your waist," she said handing Katie a pink nylon fanny pack. "You don't want a purse getting in your way. You can use this to carry your cigarettes and make-up."

"I don't feel too good," said Katie as he strapped the pack around his waist. "Maybe we should do this another day. I don't want to get sick on the rides."

"Non-sense, you'll be fine. You're just nervous." She stood back and lit a cigarette as she admired her daughter. "I can't believe this. My little girl is going on her first date!"

The doorbell chimed and Katie shuddered. He wanted to crawl under the couch.

"Stay right there," commanded Carol. "Don't move. I'll get the door."

Katie stood his ground as his mother opened the door and greeted Brent.

Carol knew by the look on the young man's face that he wasn't looking forward to taking a 13-year-old girl on a date. He was just following orders from his father. His look of apprehension vanished when he stepped inside and saw Katie. His eyes opened wide and a telltale bulge in his pants appeared. 13 or not, he was smitten by Katie.

Katie smiled at Brent and looked down shyly as his mother had taught him. He wasn't flirting though. He was in fear of his life. Brent looked like a larger version of the boys who had taunted him in middle school. He was a muscle bound jock. Needless to say, Brent was probably the kind of guy wouldn't have given him the time of day if he were meeting him as Jimmy rather than Katie.

He was a good-looking guy, standing six feet tall. He looked to weight at least 180 pounds. His biceps quivered when his arms moved. Katie knew that one false move on his part could cost him his life, or at the least- total humiliation.

Carol helped with the introduction and kissed Katie on the cheek. She warned Brent about driving too fast and told them to have a good time as she closed the door behind them. She rushed to the window and watched approvingly as Brent opened the car door for Katie.

She sighed and took a drag from her cigarette while praying that she was doing the right thing by forcing the date on Katie.

*****

Under normal driving conditions, the ride to Six Flags takes about 30 minutes, but construction on I-285 had slowed traffic to a crawl. Brent was nice enough, but she was so nervous about being with him and it felt like ages since her last cigarette. She looked around the car as he talked about wrestling. Brent looked like a wrestler and Katie would do every thing necessary to avoid his grasp regardless of whether it was loving or hateful.

The ashtray on the car's dash was pulled out, but it was impeccably clean. Apparently Brent didn't allow his mother or anyone else to smoke in his car. Katie fidgeted in his seat as he made up stories of imaginary people he knew to pass the time. He looked out the window at the other cars trapped on the highway. He needed a cigarette. The worse Brent could do was to say was no. And that might not be so bad. Brent didn't look like the kind of guy who appreciated second-hand smoke. The more Katie thought about it, the more she liked the idea. His mother said he had to go on this date. She didn't say Brent and he had to hit it off. It wouldn't be his fault if Brent hated smokers.

"Are you OK," asked Brent? "You're moving around like you have ants in your pants. If you're too cold I can turn the air conditioning down."

"No, it's not that," said Katie. "I just didn't know there would be so much traffic and I really need a cigarette."

"Oh yeah, my dad told me you're a smoker. You're welcome to smoke in my car. I don't mind. My mom smokes so I guess I'm pretty used to it."

"Are you sure you don't mind?" asked Katie as she unzipped her fanny pack and removed a pack of Virginia Slims and a lighter.

He assured him that he didn't mind so Katie lit up. In one way he was relieved to be smoking but in another way he was disappointed that Brent hadn't protested.

"Wow! I can't believe you're only 13," said Brent as he navigated the car through the slow traffic. "You look so much older. When my dad said he wanted me to go out with a 13-year-old girl I freaked. I told him I wasn't a baby sitter. No offense you know, but I'm still freaking. I never knew a 13 year old whose parents let her smoke. Hell I don't know anyone my age whose parents let them do it. I think that's so cool that you're mom knows and she's OK with it."

Katie smiled and exhaled a lungful of smoke. He had never dreamed anyone would ever approve of him smoking cigarettes much less compliment him for it. "My mom's real cool about a lot of things. What are your parents like?"

"They're pretty strict. They'd kill me if they ever caught me smoking. I guess that's why I think it's so cool that you do it. My dad didn't even say anything bad about it when he was telling me about you. It's weird you know. I'm 16- three years older than you, but I feel like you're a grown-up cause you look and act one like one. My dad said he thought you were a teacher when he met you."

Katie laughed. "Yeah, that was pretty funny."

"I'm serious Katie. You're the first girl that smokes that my parents ever let me go out with. I liked a few girls that smoked but I could never ask them out because I knew my parents wouldn't go for it. They're usually real weird about things like that. They're always thinking that people are going to be a bad influence on me or something like that."

"So I guess that means you've never kissed a girl that smokes before, huh?"

Brent blushed. "No, but I always wondered what it would be like. My mom smokes and my dad kisses her all the time so how bad can it be?"

"Real bad," said Katie as he exhaled another lungful of smoke. "I'm surprised your parents are still married. My mom dates a guy named Bobby. He was the guy your dad went to dinner with when he met me. He doesn't smoke and he's always complaining about my mom doing it. He hates to kiss her and he's always trying to get her to quit but she can't because she's addicted and so am I. You'd be a lot better off if you listened to your parents and stuck to girls who didn't smoke."

"I am listening to my parents," said Brent with a shy smile. "And they wanted me to go out with you. My mom even let me borrow one of her lighters so I can light your cigarettes for you in the park, if that's OK with you."

Katie returned Brent's smile. He was so dopey. But he heard himself telling Brent that he would like that.

"Cool!" said Brent. "I've never lit a girl's cigarette before, but I've seen my dad do it for my mom a lot."

Several minutes later Brent was exiting I-20 and turning left on Six Flags Parkway. After parking the car, they caught a tram and rode it to the entrance where Brent paid for their tickets. When they were through the turnstiles, Brent asked him what she wanted to ride first.

"I wouldn't mind riding the Scream Machine," said Katie as he placed a cigarette between his lips and searched the fanny pack for his lighter.

"Here, let me," said Brent as he fumbled with his borrowed lighter.

As Katie accepted his light, a little girl and his parents walked past them. "Look Mommy, that boy is lighting that lady's cigarette like Daddy does for you. Does that mean they're in love."

The mother shushed the little girl and pulled on her arm.

Brent and Katie both blushed. "Thanks for the light," he told Brent as he allowed the smoke to float past his lips.

Brent returned the lighter to his pocket and proudly took Katie's hand as they began their walk through the park. He kept one eye on Katie's breast and the other on all the jealous guys who were leering at them.

Katie's breasts bounced with the rhythm of his steps. He found it took some coordination to smoke, walk and bounce at the same time. He was self-conscious about walking through the park holding a boy's hand. He felt repelled and excited at the same time.

Brent was obviously thrilled to be in his company. And why wouldn't he. He had no idea that Katie was really a boy. As far as Brent was concerned, he was holding hands with the hottest girl in the park. Katie shook his head in disgust as he thought about the ruse. Brent looked so happy just to be with him.

It blew his mind to think he was hanging out with someone like Brent. Any girl in his school would die to go out with him and Katie strongly suspected that was the case at Brent's school as well. He noticed the looks they were getting as they walked through the park holding hands. Even though Katie was really a boy, he knew Brent was good looking and the nasty looks he got from the girls without dates proved his theory. They hated Katie for being with Brent.

Oddly enough he began to loosen up and became almost at peace with the idea of being with Brent. He had never considered himself to be the talkative type but there he was being a chatterbox as they waited in line for the Scream Machine.

So far Brent had been the perfect gentleman. He had lit Katie's cigarettes and held his hand and had hung on every word Katie said. This day was turning out nothing like he had envisioned the night before. He was actually having a good time.

The train pulled up to the gates signifying their turn. Katie got in first and Brent got in beside him. He lifted his arms as Brent reached across his lap for the seat belt. A slight rush went through his head as Brent's elbow touched his breasts. He wondered if Brent had done it on purpose and kind of hoped he had.

Brent pulled down on the metal lap bar trapping them inside the car. The train lurched forward on its track. People screamed and raised their arms. He felt Brent's arm come across his shoulder and pull him close. His arms felt so strong. He wanted to melt and felt foolish for thinking such thoughts. The train began its ascent up the first hill. It's ancient gears clanked and groaned. Katie felt the excitement churning inside him as their car reached the top of the hill.

Katie screamed as their car plunged down the track. His breasts, victims of gravity, bopped him on his face. He screamed and so did Brent whose arm never left his shoulder as the train raced up and down the track. The wind whipped his ponytail causing it to smack against the nape of his neck. The speed of the train, the wind in his face and Brent's heavy arm on his shoulder felt exhilarating. When the train screeched to a halt they were both screaming and laughing with everyone else and once again, Katie felt Brent's elbow brush against his breast as he undid their seatbelt. He also felt his lips against his cheek. It was brief but intentional. He said nothing to discourage him as they got off the train and made their way up the wooden ramp to the pavement.

The rules prohibit smoking in line while waiting for the rides and Katie's lungs were parched and in need of nicotine. He thought about his craving as he reached in the fanny pack for his cigarettes. He was grateful to his mother for insisting he take along two packs for the date. With his mother's encouragement he had become quite a heavy smoker over the past couple days.

Katie looked at Brent playfully as he accepted his light. When the cigarette was lit, he thanked Brent and seductively exhaled in his face. Brent inhaled the cloud of second-hand smoke and kissed Katie directly on the lips. Once again, Katie didn't discourage him. He took Brent's hand and walked along the pavement beside him.

Jimmy Higgins would have been dead meat if he had blown smoke in Brent's face. But he wasn't Jimmy was he? He walked along the pavement with a cigarette in one hand and Brent's hand in his other. Their arms swung in unison as they walked. He was having a great time with Brent and it disturbed him when he thought about it. After all, despite the breasts and clothes, he was still a boy when it was all said and done. He brushed off the thought, telling him self it didn't matter and it wasn't his fault. He hadn't asked Brent out. He had begged his mother not to make him go. But she had forced this on him. He was just trying to make the best of a bad situation.

It was easy to rationalize his behavior as it applied to his situation. However, try as he did, he could not rationalize his feelings. He had to let Brent kiss him but that didn't mean he had to enjoy it or look forward to it. What did that say about him as a person and as a boy? Katie didn't want to think about it.

The hard truth was this. He was having the time of his life. Being with Brent was wonderful! Never had so much attention and respect been lavished upon him. He made Katie feel like a princess. How could something that felt so right be so wrong? Again he found himself trying to brush away the thought and just enjoy his time with Brent.

"Do you want a Teddy Bear," asked Brent?

"What?"

"A Teddy Bear. I'll win you one if you want," he said pointing to something that looked like a big thermometer with a bell on top.

Katie stood back and enjoyed her cigarette as Brent traded a guy $5.00 for a big sledgehammer. He couldn't help but feel proud as he watched Brent's biceps ripple under the weight of the heavy hammer. He gripped it like a baseball bat and swung it up and over his shoulders. The sound of the hammer hitting the board echoed forcefully and disk sailed up the tall vertical measure ringing the bell. He did it two more times and called Katie over to choose a stuffed animal as a souvenir of their day together.

Katie ground the cigarette beneath his sandal and walked up to the display. Brent looked so proud to have won a prize for him. Katie pointed to the pink rabbit with long floppy ears. The guy gave it to Brent who exchanged it with Katie for a kiss that he willingly gave.

The rabbit came with a carabineer clasp and Brent used it to attach the stuffed bunny to the back of Katie's fanny pack. The rabbit bounced against his ass as he walked. It looked strange but it freed his hands to smoke and hold Brent's hand.

Katie had come to understand that Brent was one of those boys his mother had told him about- the kind of guy that gets off on seeing girls smoke. In other words, Brent was a lot like him. He paused and took out another cigarette and allowed Brent to light it for him. The way Brent looked at him when he smoked made him feel sexy and he relished the feeling. He had never felt sexy to another human being in his life. So what if Brent was a guy. That didn't change the feelings he was experiencing and since he had to be here he might as well enjoy it.

It was official. Katie had become a chain-smoker. As fast he could smoke a cigarette, Brent was prepared to light another one for him. It made them both feel very grown up.

As they walked around the park, Katie spotted three boys who looked to be about his age. They were scrawny little losers like him. They were huddled together trying to light their cigarettes with a match but were having trouble with the wind. Guys and girls, both smokers and non-smokers, walked by and made fun of them. Brent, his bully boyfriend was no exception. He called them fags as he walked past them. Fags, thought Katie. That's what he'd think of me if he knew the truth. But it would be so much worse because he kissed me. He thought of all the little kisses Brent had given him that day. They had all been quick pecks for the most part. After all, they were in public. It wouldn't be proper for Brent to rape him with his tongue with all these people around.

"Look over there," said Brent excitedly. "It's the Monster plantation. Wanna go?"

Katie grimaced. The Monster Plantation was Six Flag's version of the tunnel of love. It was a little boat that floated around in the dark giving couples a chance to get it on in a "G" rated kind of orgy.

He finished his cigarette with a deep puff and ground it into the pavement with his heel. "Sure," he said. "I'd love to."

Several minutes later Brent was helping him into the boat. He sat down and put his arm around him. Katie leaned in and nestled his face against his neck. He felt so safe and secure beside him. But more than that, he felt excited. He didn't understand what was coming over him. Maybe it was the hormones. His mother told him the pills would make him emotional. If that were the case he would stop taking them immediately. Today was a day he would do his best not to repeat or remember. And then Brent kissed him on the cheek. But I'll make the best of it, he thought.

The flame of Brent's courage was fanned by the darkness. He squeezed Katie tight and buried his nose in her blonde hair. The smell of smoke clung to her and excited him. He had always had a thing for girls that smoked but had never been this close to one. And never had he been with a girl who looked as good as Katie. The fact that she was only 13 meant nothing when he looked at her breasts. Her breasts he thought. He moved his arm across her shoulders until his hand was on top of her breast. He could palm a basketball but not Katie's massive breasts. But that didn't keep him from trying. He felt her move. Was she trying to get away? His father would have his head if he found out he had behaved less than honorably with the young beauty sitting beside him. But he was thinking with his penis now and he wanted her. He squeezed her breast and drove his tongue into her mouth.

The feel of her massive breast in his hand, the taste of her smoky breath in his mouth. He was kissing an adult woman. She couldn't be 13. The kiss was sloppy and wet. All his years of wondering what it would taste like to kiss a girl that smoked were finally answered. His eyes rolled to the top of his head as he became lost in her smoky kisses. He knew he shouldn't but was powerless over his urges. With one hand still on her breast, he reached around her with his other. When he found her hand, he moved it to his groin. It was wrong but he couldn't help him self.

Katie didn't draw his hand back. He felt it close around Brent's penis. I'm a fag he thought as he rubbed Brent's erection. As disturbing as this thought was, he couldn't remove his hand from Brent's groin nor could he unlock his lips from Brent's mouth. He kissed Brent passionately as he told himself he was just making the best of a bad situation.

*****

It was past seven o'clock when they arrived back at Katie's house. Brent parked the car and walked around to open her door. Katie took his hand and allowed Brent to help him to his feet. They held hands as they walked up to the house.

Katie smiled warmly at Brent and thanked him for the date. He told him that he had had a wonderful time. And then he put his arms around Brent's neck and kissed him passionately one more time before saying goodnight. Brent asked if he could see her again. Without making a promise for a second date, Katie told him to call her and kissed him one more time before going inside, leaving Brent to walk down the drive by himself.

Katie closed the door behind him and leaned against it. His knees were weak. His emotions were in overdrive. His mother was sitting on the couch smoking a cigarette. He wondered if she had peeked at them through the peephole in the door as they were kissing. He was so ashamed of himself.

Carol knew by the look on Katie's face that he had been on an emotional roller coaster. "Come sit down and tell me about it," she said as she patted the couch.

Katie looked up toward the ceiling as he fought back the tears before falling on the couch beside her. He broke down and sobbed uncontrollably on his mother's shoulder. She rubbed him as he cried, telling him to get it all out and he would feel better in a moment. When his sobbing slowed down she offered him a cigarette and he accepted it. They sat on the couch and smoked without talking.

"Why are you crying Katie? Did Brent do something to you?"

Katie shook his head and took a deep drag from his cigarette. He exhaled the smoke slowly, looked at his mom and said, "No, he was perfect."

"Then what's wrong? Didn't you have a good time?"

"I did Mom. I had a great time and that's the problem. He kissed me and I liked it. I feel so gross. I kissed a boy Mom! How sick is that?"

Carol smiled and gently rubbed her daughter's shoulders. "It's not sick at all Honey. It's normal and it's natural."

"No its not! It's not normal at all, and I did more than just kiss him. I touched his penis! He was wearing pants but I still touched it."

"Oh Katie. That's normal too. Your normal and he's normal. He's a guy and you're a girl. I know you don't think of your self as a girl yet, but you are."

"I'm not a girl Mom. I've got breasts but I also have a penis and so does he."

Carol took a deep puff from her Virginia Slim as she contemplated her next words. "OK, lets think about this. You're right. You do have a penis. But tell me, did you want to stick it in Brent today."

"Gross! Of course not. I'm not gay!"

"I didn't say you were Honey. We're just talking. What about Brent's penis? Did you want him to put it in you?"

"I don't know," said Katie. "Maybe. But I didn't think about it like that. It wasn't like I wanted him to fuck me in the ass."

"That's good," said Carol. "It means you're thinking like a girl Honey. It means you're not gay."

"Really? Are you just saying that to make me feel better?"

"I love you Katie. I'd do any thing for you, but if I thought you were gay, I wouldn't have allowed this to go as far as it has. I wouldn't have spent the time or the money. I did this because you're a girl in a boy's body and I'm trying my best to make it right. If I thought you were gay, I would have loved you the same. But I would have helped you come out of the closet- that's all. This is different. Don't you see?"

Katie sniffed, took another puff from her cigarette and crushed it out in the ashtray. "I'm so confused Mom. I don't know what I am."

"But you know how you feel, don't you?"

Katie nodded as he picked up his mother's pack of Virginia Slims from the coffee table and lit one.

"Good," said Carol. "Let's have a mother-daughter talk with just your feelings in mind. Let's talk about your date but we'll talk about it like you're a natural girl. OK?"

"OK," said Katie as he took a deep drag and composed him self.

"You said he kissed you. Let's talk about that. Did he kiss you first or did you kiss him?"

Katie told his mom about how Brent had kissed him several times on the cheek and on the lips but they were like pecks.

She told him that he was using the quick kisses as a way to test the water. "He wanted to see if you'd be receptive to him but he didn't want to risk your rejection."

Carol beamed as Katie described his first real kiss with Brent in the Monster Plantation.

"And you liked it," asked Carol?

"I felt like I was floating Mom. It was like my toes curled. And all these explosions were going off in my head. I didn't want it to end."

"And that's when you touched his penis? When you were on the boat in the Monster Plantation?"

Katie nodded and took a puff from his cigarette.

"I think that's wonderful Katie. I'm so proud of you. Did it feel big?"

Katie smiled at his mother. For some reason his feelings of shame were being replaced with excitement as he thought about touching Brent's penis. "It felt a lot bigger than mine Mom. I know that isn't saying much. But it was so hard. It felt like a rock."

Carol put her hand on Katie's and looked him in the eye. "I think that's so wonderful Katie and I'm so glad you're attracted to him. Maybe someday you will be able to have intercourse with Brent like a real girl, but there are other things you can do before then."

"You mean like giving him a hand job," asked Katie?

"And even more if you'd like," said Carol. "I know you're only 13. But you've heard things and you've probably thought about them too. Do you know about oral sex?"

"Oral sex- like blow jobs," asked Katie?

Carol nodded.

"I don't know Mom. That sounds so gay. I couldn't do that."

"You have to quit thinking of your self as being gay. You're not. You're a woman and someday if you want, we'll fix your body so you'll be able to have sex like a real woman. But the important thing to remember is that in your mind and heart, you're as much of a woman as I am."

"You really think so?"

"I know so Honey. There's nothing wrong with a woman putting a man's penis in her mouth if she really likes him. You like Bent, don't you?"

"I like him a lot Mom."

"Well there you go," said Carol throwing her arms in the air.

"But what if he cums in my mouth? That could happen couldn't it?"

"If you're lucky it will. Bob and I have oral sex all the time and he always cums in my mouth. I love it and so will you! Oh Katie! Don't you just love being a girl? Isn't it wonderful?"

Cigarettes Are a Girl's Best Friend -4-

Author: 

  • Slim V.

Audience Rating: 

  • Restricted Audience (r)

Taxonomy upgrade extras: 

  • Transgender
  • Transitioning
  • Posted by author(s)
  • Preteen or Intermediate
  • Serial Chapter
  • Contests, Deals, Bets or Dares
  • Breasts / Breast Implants
  • Estrogen / Hormones
  • Surgery
  • Smoking Fetish

Cigarettes Are A Girl's Best Friend

by slimv

 

Part 4

 

 

"I think you've made terrific progress," said Dr. Doyle as she leaned back in her chair and studied the expressions on the faces of the mother and daughter sitting in front of her. Her experience had taught her that what a client didn't say was as important as what they did say. She had the uncanny ability of being able to extract hidden information from her clients by studying their facial expressions and body language.

Carol was energetic and could hardly contain her self as she talked about her daughter's first date. It was obvious to Dr. Doyle that the mother was reliving her life through her daughter as mothers often do.

Katie, on the other hand, was clearly confused about his new feminine feelings. Much of the confusion could be attributed to the introduction of hormones to his body. He was also experiencing grief over the gradual loss of his male identity and the shrinkage of his already slight penis. And last but not least, his heterosexual programming was at odds with his new situation.

"So tell me Katie, how did Brent react to your smoking?

"He liked it a lot I think. He kept telling me how mature it made me look and he was always lighting my cigarettes."

"How did you feel when he lit your cigarettes? Did you enjoy the attention?"

"It was great. It made me feel sexy and kind of powerful. It was weird cause he's so much bigger and stronger than me but when I was smoking I felt like I could make him do any thing."

"You said he's an athlete, so I assume he doesn't smoke. I suspect his parents wouldn't allow it. You also mentioned that his mother smokes, so I would expect him to associate smoking with female superiority. I'm not surprised in the least that he is attracted to your smoking. Because of his upbringing, he has a great amount of respect for you. Tell me Katie. How does this power and respect make you feel?"

"I love it. No one ever treated me like that when they thought I was a boy. I felt so grown-up when I was with him."

Dr. Doyle raised her eyebrows and told Katie his comments were very interesting. "Yet, you're still bothered about losing your male parts. I would think you'd be biting at the bit for a complete sex change. It sounds as if your life as a female is much better than it was when you were completely male."

"It is. I love dressing like a girl. I love having breasts. I like the way people treat me cause they think I'm Katie. It's just that I kind of wonder what it would be like to use my penis. I don't know what I'm going to be missing and that bothers me. I think I really want to be a girl someday but I keep thinking it's going to bother me if never know what it was like to be a guy."

"So what you're saying is that you want to have sex with a female to know what it's like to be a male."

Katie bowed his head and looked away.

"Wanting to have sex is nothing to be ashamed of. I'm sure your mother told you that sexual desires are normal, natural and instinctual. Wanting sex is a part of being human. Sex is a basic human need. So please don't feel embarrassed about this."

"Katie, look at me when I'm talking. I'm going to be blunt. Carol, I want you to hear this too. Katie, I'm 100% convinced that your future happiness depends on your ability to forge good relationships with men as a woman. That means you won't find happiness as a lesbian. You're heterosexual and you need to feel good about your feelings for Brent and other young men that will become a part of your life as a woman. However, I'm also convinced that you need to get this male wild hair out of your system. I think you need to have sex with a woman."

"How is that possible Dr. Doyle," asked Carol? "Katie has breasts and in case you haven't noticed, they're huge! What girl in her right mind would have sex with him looking the way he does now?"

"First of all Carol, Katie doesn't need a girl. You're right. It would be impossible to find a girl his age that would willing to engage in such an encounter. Katie needs an experienced older woman who can show him the ropes while maintaining a professional consideration for his emotions. With circumstances as they are, I feel it would be appropriate if you allowed Katie to have sex with a prostitute."

"A prostitute," shouted Carol! "You want my daughter to have sex with a whore? Do you realize how dangerous and unhealthy that is?"

"I admit there are risks involved, but the only other alternative I can fathom is incest. Would you being willing to have intercourse with Katie?" She looked at Katie and asked, "Would you be willing to have sex with your mother?"

Katie didn't answer, but Carol did. "Yes! I'd be willing. He was my son and now he's my daughter. I love her more than life itself and I will do anything necessary to ensure her happiness."

"Very well then," said Dr. Doyle. "Do it tonight. I'll have my secretary make an appointment for a follow up visit tomorrow afternoon so we can discuss the event and it's implications."

*****

Katie followed his mother to her bedroom, the place where his transformation had begun. It was ironic that this was the room in which his manhood would be experienced for the first and last time. Carol closed the door behind them. She had two packs of Virginia Slims and a lighter in her hand. The look on her face was both grave and loving.

"How do you feel," she asked?

"I'm scared Mom."

"Are you sure you want to do this? Do you think it will bother you?"

"I got to know what it's like Mom. I'm just sorry it's got to be you."

"Don't worry about that Honey. Believe me. This isn't going to painful for either of us. And if it makes you feel better, I used to fantasize about making love to you when you were a boy. I know that sounds awful, but I needed to tell you so you'll know I'm kind of looking forward to this."

Katie's eyes grew large. "No shit? Me too!"

"What," asked Carol? "You used to fantasize about making love to me too?" A smile that reflected Katie's formed on her lips. "Come on," she said. "Lets get undressed and have a cigarette while we talk about this."

Mother and daughter sat naked on the bed smoking cigarettes as they admired each other's bodies with their eyes and hands. The situation, once tense and guilt ridden had become fun and lighthearted. The uncovered knowledge of each other's hidden passions had given them courage and peeked their curiosity in each other.

Katie placed his hands on his mother's breasts and she did the same to his. He kneaded them between his fingers and played with her nipples. It was the first time he had ever touched breasts other than his own. The fact they belonged to his mother made the moment even more special. His mother wasn't young, but she was still attractive. Her breasts, even though they sagged from age, still held great appeal to him.

"I remember when you used to nurse from them," said Carol. "You were such a beautiful baby. Even then I imagined you as my daughter. Would you like to suck Mommy's breasts again Honey."

Katie grunted yes.

"Put your cigarette out first. I don't want to get burned."

Katie took another puff from his cigarette and put it out in the ashtray. He positioned himself low on the bed so his face was directly in front of his mother's right breast. She drew on her cigarette as his mouth engulfed her swollen nipple. He felt her hand upon his head, stroking and petting him as if he were her lap dog.

"That feels so nice Baby. You're sucking Mommy so good. It feels just like it did when you were nursing. But now you have teeth," she giggled as she pulled his head off her breast so that they were face to face.

Katie watched as his mother lifted the Virginia Slim to her lips. He watched as the tip of her cigarette glowed red. She pulled it away and without inhaling touch her mouth to his. He felt her soft lips lock on top of his and tasted the smoke as she gently blew it into his mouth while bathing his tongue with hers. He had no choice other than to inhale, and as he did he felt his small penis stiffen.

"Did you like that," asked Carol? "Bobby calls it sharing smoke. It drives him wild."

"I thought he didn't," smoke said Katie. He was still dizzy from his mother's passionate smoky kiss.

"Let's just say he's addicted to my kisses," giggled Carol.

"Do you think Brent would like that if I did it to him?"

"Why do you think I showed you," asked Carol? "But whatever you do, don't let him take up smoking on his own. If he asks you for a cigarette, tell him no."

"Why?"

"Because it could demystify the feminine experience for him. It's all about that power you were telling Dr. Doyle about. You could lose some of that power you have over him if he starts smoking on his own."

Katie picked up the pack of Virginia Slims and joined her mother in a cigarette. "Mom, I've been wondering. You didn't get mad at me the day you caught me smoking and wearing your clothes. I know you didn't believe me when I said I wanted to dress up for Halloween as Cruella DeVille. But I was wondering. Would you have let me smoke if all of this hadn't happened- if I was still a boy?"

Carol took a deep drag from her cigarette as she pondered her daughter's question. "No Katie, I wouldn't have. I've never been attracted to men that smoke. I don't know why and I can't explain it but it's how I feel. I'd be ashamed to have a son that smokes. But when I saw you wearing my clothes and smoking my cigarettes, I saw the daughter I could never have but always wanted."

"Don't get me wrong. I think smoking is very unhealthy. Neither of us should do it, but then again, neither of us are ever going to quit. But there are some very positive aspects to the habit as I believe you're finding out for your self with Brent."

"Dogs may be man's best friend Katie, but cigarettes are a girl's best friend. They're almost like the perfect food; zero calories, zero carbs. They taste wonderful and make us look sexy. They help us maintain our weight. They relax us and stimulate us and help us deal with stress. They give us something to do with our hands while we talk on the phone. You probably knew all that. But what you probably didn't know is that cigarettes and sex go together like peanut butter and jelly. Smoking during sex will amplify and enhance a woman's orgasm and it drives men wild with passion."

"Really," asked Katie as she took a drag from her own cigarette?

"Oh yes," said Carol. "And you're about to experience it first hand, right after me of course. Now lie on your stomach and put your head between my thighs. I want you to get your face right up next to my vagina so that you're kissing my clitoris. I'm going to teach you how a man pleasures a woman with his mouth."

Katie followed his mother's instructions and positioned his head between his mother's thighs. His mother's vaginal aroma was pungent but rather pleasant as well. It was the first time in his life he had ever seen a real vagina and he was in awe of it. He rubbed his fingers against her course pubic hair.

"It's beautiful Mommy."

"I'm glad you like it Honey. Maybe someday you can have one just like it. Ok Darling. Mommy is going to start smoking now," she said as she lit a cigarette. "And she wants you to lick her clitoris lips with your tongue."

"What's a clitoris look like?"

"It's folds of pink skin shaped like a lip. There's a little nub inside and it's going to make me feel real nice when you touch it with your tongue."

Katie shifted on his stomach and stretched his neck. He recoiled slightly from the taste of his mother's flesh. It was acrid and somewhat salty, but his excitement and hers drove him forward.

"Oh yes, Honey! Just like that. Keep licking Mommy just the way you're doing. Oh Baby, it feels so good. Don't stop. Whatever you do don't stop until Mommy tells you too," she said as she pulled hard on her cigarette.

She wiggled her hips and squirmed against his mouth for five or six minutes and suddenly stopped. The pause was only momentary. And then Katie felt his mother's hips lurch against his face. Her legs clamped down on his head like a vice and heard her scream his praises to God.

When it was over, he lifted his head and propped himself up. His mother was laid out beneath him, spent, her half burned cigarette dangled from her lips. His face was wet with his saliva and her juices. He wiped his face on the sheet and lay beside his mother who told him how wonderful he was as she finished her cigarette.

Carol took a drag from her cigarette and held the filter to Katie's lips so he could share a puff. "You'd make a wonderful lesbian," she said as she exhaled a lungful of smoke. "But that would break my heart, so no more women for you after tonight."

Katie took his mother's spent cigarette from her lips and put it out in the ashtray. He sat up and lit two more, one for each of them. He was proud of himself. He had brought a woman to orgasm. The fact that the woman was his mother sweetened his sense of accomplishment.

"Stay right there," said Carol as she got to her knees. "I'm going to show you something else you can do with Brent."

Katie looked down and watched as his mother took a deep drag from her cigarette and exhaled her smoke against his stiff little penis. As small as it was, it was still throbbing hard.

"That's so neat," he said.

"I thought you'd like it," she told him. She took another puff and did it again, putting her cigarette out in the ashtray afterwards. "OK," she said. "Turn about is fair play, so now I'm going to do for you what you did for me. I'm going to suck on your penis while you smoke. You're going to sense the orgasm right before it hits and before it does, I want you take a big puff and hold the smoke in your lungs without exhaling until you cum. OK?"

Katie nodded as his body tensed in anticipation. "Should I tell you before I cum so my stuff doesn't get in your mouth?"

"Your stuff is called sperm and I want it. You just lay back, relax, and leave the driving to me."

Carol smiled as she took Katie's stiff little penis between her fingers and lowered her mouth on it. It was so small and cute- nothing like Bobby's. She heard him groan in pleasure as her tongue worked it's magic on his little member. She couldn't see her daughter's breasts from between his legs. Her daughter was for all practical purposes her son as she engulfed his small penis.

Carol was an experienced cock sucker and Katie exploded in her mouth before he was halfway through with his cigarette. She couldn't help but smile when she saw the spent look on his face. "Better than your hand," she asked?

Even though he was young, Carol knew he needed time to recoup before continuing. She used that time to discuss what she had done for him while they cuddled and shared a cigarette.

"So what do you think Katie? Did it feel good when I sucked your penis?"

"Mom, it felt wonderful. I don't know what to say. It was incredible!"

"Do you think it would bother you to suck a boy's penis if you really liked him?"

"I don't know Mom. I like Brent a lot. But I don't know if I like him like a friend or like a boyfriend. It still seems weird to think about doing something like that to another guy. Something about it doesn't seem right."

"OK. If you were a boy do you think you and Brent would have any thing in common? Would the two of you be friends?"

"No way," said Katie. "He'd hate me if I were a guy."

"It felt good when he kissed you didn't it? You told me you saw fireworks and your toes curled. Why do you think you felt that way?"

"I don't know. It bothered me. It felt good but it shouldn't have because it wasn't right. I shouldn't have let him kiss me and I shouldn't have kissed him back. That was wrong Mom."

"It wasn't wrong Katie. It was nature defeating nurture. You're an attractive girl and he's an attractive boy. You have sexual feelings for each other and there's nothing wrong or abnormal about that. I was so happy when you told me about him kissing you, and holding your hand, and lighting your cigarettes. He likes you and he treats you with respect. When he looks at you, he doesn't see a boy. He sees you and you're a beautiful girl. I wish you could see your self that way."

"I bet he'd like it if I sucked his penis wouldn't he? It felt so good when you did it to me. I do like him Mom and I'd like to make him feel good."

"Helping a boy to feel good is only a part of it Honey. Oral sex or any kind of sex between two people should be taken seriously. It's not recreation and it shouldn't be casual. Sex with the wrong person for the wrong reasons can be degrading. I didn't feel degraded when I sucked your penis. I don't feel that way when I'm with Bobby. It's a very intimate expression of love."

"I know that Mom. I wasn't a slut when I was a boy and I'm not a slut now."

"That's good. I just wanted to make sure we're on the same page. And I want you to know that if you have feelings for Brent, and if he's as nice as he appears, well, it wouldn't bother me if you shared your self sexually with him. I think it would be good for you."

"I understand Mom. I'll think about it, OK? Thanks for doing this for me. I know it was kind of weird but it meant a lot to me. I guess we should get of bed now, or at least I should."

"Not so fast Katie. I thought you wanted to use your penis to make to love to a woman."

"You'll do that for me?"

"Oh yes. I want you to know what it's like for a guy and I want you to think about me as well, so you'll know what to expect if you become a full woman."

Katie grinned. "Are you going to smoke like you did when I used my mouth?"

Carol answered his question with a smile as she laid back and lit a cigarette.

"Alright Honey. Get on top of me like you're doing push-ups. You need to get your penis over my vagina. That's it. Good. You're doing so good Honey."

Carol reached down and found Katie's small penis with her hand and guided it to her vagina."

The sight of his mother lying naked beneath him smoking her cigarette was candy to his eyes and food for his erection. His jaw dropped when he made penetration. His penis was so small; the expression on his face was the only way his mother could tell for certain that he was inside her.

"That's good Honey. Now move your hips and bounce around. You know what I'm talking about. Just do what makes you feel good."

Human instinct took over and Katie began to buck his hips as he inhaled the sight and fumes of his mother smoking beneath him. It was over almost as soon as it started. He arched his back, threw back his head, groaned and then collapsed on his mother's naked body.

"How was it," asked Carol as they shared a cigarette?

Katie exhaled a lungful of smoke and wiped his brow. "Amazing. It was absolutely incredible Mom!"

"I'm glad you liked it Honey."

"Was it good for you too? You didn't look like you had an orgasm like you did when I used my mouth."

Carol leveled her eyes on the remnants of her son. "I'm going to be perfectly honest with you Honey and I don't want you to get upset about it. Your penis is too small to sexually satisfy a woman."

Katie deflated. He looked down at his penis. Even erect it was less than four inches. The only thing it was good for was pissing and jacking off. "I'm sorry," he said.

"Don't be sorry Honey. It's not your fault. It's the way you were born. It pains me to hurt your feelings, but you're my child and I want what's best for you. You should think of it as one more reason to finish what you started and become the woman you should have been born as."

*****

Dr. Doyle listened as Katie described the sexual experience with his mother. As she had expected, the experience had helped him come to terms with his diminishing male attributes. It had made him more receptive to the potential of his female side.

"Your mother did you a favor by not sugar coating the truth Katie. I know how much it must have hurt to hear her say it, but she's right. Your penis is pathetic. No girl in her right mind would want to be with you because you're incapable of satisfying her sexual needs. But as a woman you could satisfy both your self and your male partner's."

"So I'd still have orgasms if I had a vagina. It would feel the same as if I had a penis?"

Dr. Doyle smiled at Katie. "No Dear. It would feel better than that."

Cigarettes Are a Girl's Best Friend -5-

Author: 

  • Slim V.

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Transgender
  • Posted by author(s)
  • Serial Chapter
  • Femdom / Humiliation

Cigarettes Are A Girl's Best Friend

By: slimv

 

Part 5

 

Laura Doyle put down her menu, gave her order to the waiter and lit a cigarette. "You know Bobby, I'm always glad to see you. We go back a long way and

you mean a great deal to me, but I have to tell you, I'm a little uncomfortable talking to you about Katie. I know you're seeing her mother. But you're still not family and even if you were, there would still be doctor-patient confidentiality issues to consider."

"We're friends Laura. So lets talk like friends. I think I have every right to be involved with this because Katie's life involves my life. My God Laura! My entire world has flip flopped ever since I gave Carol your phone number. My best friend's son is dating my girlfriend's son. And you realize of course that Brent has no idea that Katie is really a boy. Their relationship affects my life. And then there's what happened between Katie and Carol. I couldn't believe it when Carol told me. They committed incest you and encouraged it!"

"I didn't encourage it Bobby. I'm Katie's doctor. I'm not a cop and I'm not their pastor. You think I'm evil because I don't share your views. I realize your church is important to you but it's not important to me. And it gets in Katie's way. The last thing she needs right now is a bunch of bible thumping hypocrites throwing stones at her."

"I'm not throwing stones at Katie. I'm throwing them at you Laura. Carol said you suggested a prostitute. Why didn't you stick to your guns? For Christ's sake, all he needed was a willing female to get his rocks off with. It didn't need to be Carol. What were you thinking?"

"I was killing two birds with one stone. Katie isn't like most of my patients. He's confused about his gender but he's walking a fine wire as far as his sexuality is concerned. He's bi-sexual. Some people think that's fine but I don't prescribe to that school of thought. I believe a person has to choose a team and stick with it. You're either straight or your gay. It's black and white in my book. I think any thing else causes uncertainty and doubt later in life."

"Maybe you're right Laura. I wouldn't know. But shouldn't Jimmy or Katie decide this for his or her self?"

"That would be OK in a perfect world, but we don't have that kind of time."

"OK, now that you mention it. I've been wondering about this too. Why is everything happening so fast? I'm not an expert but I thought this kind of thing took years to resolve."

"It often does take years, but it shouldn't," said Laura. "Look Bobby, I've already told you more than I intended, but since I've gone this far I'll go all the way. The reason why I didn't discourage the incest issue between Carol and Jimmy is because Jimmy is heterosexual. That means he has an Oedipus complex."

"Give me a God damn break Laura. Why do you shrinks think every guy wants to fuck his mother?

"Because it's true Bobby. You may not want to admit it because you're over that stage of your life. But you're really not. You're forgetting. I knew your mother well. And from what I can see, Carol and your mom could be twins, so don't sit there holier and thou and tell me that I don't know what I'm talking about. Maybe if you had had sex with your mother you wouldn't be with Carol now. Maybe you never would have married and divorced Janet. After all, she was quite a lot like your mom too. Well Jimmy has this Oedipus business behind him now. He needed to know what it was like to have sex as a male and I helped him to discover what it was like. He can proceed with his new life without regrets. And he won't be burdened by trying to find his mother in all his future sex partners."

"You can rationalize anything Laura, can't you?"

"That's why I get the big bucks Bobby. Good logic doesn't always mix with good morals."

"Let's say you're right about this Oedipus thing. Why the hell are you rushing things?"

"The urgency is based on my personal experience and I happen to believe my personal experience has value. Jimmy isn't my first client with gender issues. I've tried it by the book Bobby. Just because his condition doesn't appear to be immediately life threatening, it still requires an immediate remedy. He's 13. He has his whole life in front of him but that life is largely based on his life right now."

Laura took a drag from her cigarette and continued. "There's no doubt in my mind that Jimmy should have been born a girl. I feel it in my bones. If I'm wrong, he won't be able to bring him self to have a sexual relationship with Brent. He'll stop before it happens. His wiring won't allow it. And if that happens, I'll readjust my strategy. But it's not going to happen. Katie wants this more than Jimmy doesn't want it. You mark my words Bobby."

She crushed out her cigarette and lit another. She pointed the lit end at Bobby as if she needed a prop to get his attention. "Bobby, I've been in love with you since the first day we met in college. And you loved me until..."

"Until I found out you were really a guy with a penis," finished Bobby.

"Precisely," said Carol, pausing to take a drag. "I knew I was meant to be a woman when I was Jimmy's age. But my parents wanted to cure me. My doctors wanted to make sure. My life was a living hell in that in-between stage. You're a good man Bobby. If I had been a woman when we met, you might have been able to accept me. I don't blame you for changing your feelings when you found out. But I remember the look on your face when you saw my penis. You can't tell me that look would have been different if I had showed you a vagina and told you that there used to be a penis there."

*****

Katie puffed nervously on her cigarette as Brent steered the car along the narrow and winding back roads. They were supposed to be going to Stone Mountain Park for a picnic lunch. That's what Brent had told Katie and that was the story he had told his mother. But here they were on the shores of Lake Lanier driving toward Brent's lake house. Of course it wasn't Brent's house. It belonged to his parents who didn't know their son had plans to borrow it.

He could have told Brent no. Going to the lake house was Brent's idea but he had asked Katie if it would be OK and she had said yes. He could still change his mind. Brent would be disappointed but he'd survive. More importantly, Katie would survive.

Katie lit another cigarette and looked out the car's window. There were few houses and many trees. Brent could bury him in these woods and no one would ever find him. For that matter, he could dump his body in the lake. Either way, the stakes were high. His life depended on him keeping his head.

"Are you sure this is OK with you," asked Brent. "We can still go to Stone Mountain if you want. You look so nervous."

"No, I'm fine. I want to see the lake house. It's just that I started my period today and I feel a little queasy. But I'm fine. This is fun. Thanks for taking me."

Brent grimaced as he thought of her period. He was a guy and he wasn't knowledgeable about such things. He was on a need to know basis as far as the female body was concerned and periods were something he didn't need to know about it.

Katie took a deep puff from her cigarette and wondered if Brent would pick up on his subtle message. His mom, being a wise woman had told him about the period ploy. She said it would keep Brent out of her panties. Katie hoped his mother was right.

Katie's shoulder bumped against the car door as Brent turned off the paved road. The gravel trail was bumpy and Brent swerved to miss the potholes. An ash fell from her cigarette to her lap and she bushed it away. When she looked up, Brent was pulling up a driveway that led to a cedar A-frame house. He could see the lake behind it and thought it would probably make for a nice view from the back of the house.

"We're here," said Brent, as he put the car in park and turned off the engine.

*****

After touring the house, Brent led Katie to the couch. He told her to have a seat while he got one of his mother's ashtrays from the kitchen. He asked if she wanted any thing to drink and Katie told him to bring a Diet Coke if he had one.

As he sat on the couch waiting for Brent, he wondered why he had allowed himself to get in this predicament. He knew full well why he was here. He had come to prove a point to himself and to his mother and to Dr. Doyle. He would find out today if he had what it took to be a woman.

Brent placed an ashtray and two Diet Cokes on the coffee table and took a seat beside Katie. He saw she was holding an unlit cigarette, so he fished the borrowed lighter from his pocket.

Katie accepted his light, inhaled a deep puff and thanked him as he exhaled the smoke directly in Brent's face. He wasn't being rude. He knew Brent liked it when he did it. And he needed the confidence boost.

Brent felt a stirring in his loins. Katie noticed it too but said nothing, so as not to embarrass him. Seeing Brent's erection and knowing he was the cause of it made him feel sexy.

Brent had a difficult time believing that the beautiful busty chain smoker sitting beside him was only 13. He feared she was more of a woman than he was a man. It bothered him to be intimidated by her adult features and habits. He felt like a little boy sitting beside her. He grew up hearing his mother say girls mature faster than boys. Perhaps his mother knew what she was talking about.

"Is every thing OK," asked Katie? "You look bothered. Are you on your period too?"

Brent laughed at Katie's joke. "No, nothing like that. At least I hope not. I just can't get over the fact that you're only 13."

"Is that a problem," asked Katie shyly?

"No, it's not. I just feel nervous. I've never been out with a girl as pretty as you."

Katie smiled at him and blew another puff of smoke in his face to keep the fire in his pants stoked.

Brent shifted his body on the couch so he could put an arm around her. He drew her close and pressed his lips against hers. Her mouth opened to receive his tongue. She tasted like burnt tobacco. It was a taste he had dreamed of every night since their first date. He loved the flavor of her smoky kisses.

As much as it turned him on to see her smoke, it bothered him that she was allowed to something he wasn't. He knew it was a juvenile thought. He was being stupid and showing his immaturity by thinking about it. Better to be quiet and thought a fool than to speak up and remove all doubt. He spoke up anyway.

"Can I try one of your cigarettes," he asked.

"No."

He was surprised by her prompt rejection. She hadn't even thought about it. "Why not," he asked? "You smoke and I'm older than you."

Katie told him that age had nothing to do with it. "If I jumped off a cliff, would you jump too, just because you're older than me?"

"That's not the same thing," argued Brent. "What's your problem?"

Katie was just following his mother instructions by saying no, but he didn't want the disagreement to get in the way of what he needed to do. He took his mother's advice. He put the cigarette to his lips and pulled hard on the filter. Without inhaling, he pressed his lips to Brents and blew the smoke gently in his mouth.

Brent was taken by surprise. He coughed and sputtered. But he was also excited. "Do that again," he said.

Katie disregarded Brent's request and unzipped the fly on his jeans.

Brent forgot about the kiss and undid the button as he squirmed out of his jeans.

Katie stared at his destiny, as it stood tall between Brent's legs. He closed his eyes and opened them again. The penis was still there, all seven inches of it. As he looked at Brent, he thought of the night spent with his mother. He liked Brent and he wanted to make him feel as good as his mother had made him feel that night.

He took a puff from his cigarette and exhaled on Brent's penis. Brent gasped. If Katie didn't do something right away, Brent would have an orgasm without his help.

He put his cigarette out in the ashtray and knelt on the floor in front of Brent's spread legs. He felt Brent quiver as he took the penis in his hand. He ran his fingers up the shaft, stopping to play with the engorged head. The sight of Brent's penis in his hand was strange indeed. He analyzed his feelings as he moved it between his fingers. He thought about the softness of the skin. He leaned forward and kissed it with his lips and then rubbed the head against his cheek.

"You don't have to do this," said Brent.

Katie looked up at him. "You're right. I don't have to do any thing. But I want to do this. I think I've wanted to do this from the first time I saw you. I really like you Brent."

"I like you too Katie. I won't cum in your mouth. I promise."

He gently kissed the penis head, looked up again and smiled. "That's OK. I want you too."

Brent watched as Katie's head went down. Her long blonde hair covered his lap. He tensed as he felt his penis disappear in to the sweet dark recesses of her wet warm mouth. His head fell back and he took her hair in his hand and stroked it as she lovingly attended to him.

This wasn't the first time a girl had sucked him off. But this was different. He'd never cared for those girls. They were sluts- all of them. But Katie was different. She was his princess and the love of his young life.

For the first time since putting on his mother's clothes, Katie felt like a woman. Making love to Brent with his mouth seemed like the most natural thing in the world. Brent's moans were music to his ears. The touch of his hands against his hair made him swoon. He felt no shame as he caressed Brent's sweet penis with his tongue. He was Brent's girl and he was her guy.

He heard and felt the warning signs. The muscles in Brent's thighs tensed. Brent's groans penetrated his ears. He felt the power of his hands and thrust of his hips and they joined to push him deeper into her mouth. He was cumming and the taste of his sperm was like victory. His life fluid filled her mouth. It was hot. It was salty. It was Brent and she loved it. She swallowed it without hesitation. And when she was done, she released him from her mouth and kissed the tip of his penis that was still erect.

He thanked her. She answered him by kissing the tip of his penis again.

"I wish I could do the same for you," he said. "I wish you'd let me make you feel as good as you made me feel."

Katie smiled up at him. "You will some day. Just not today."

Cigarettes Are a Girl's Best Friend -6-

Author: 

  • Slim V.

Audience Rating: 

  • Restricted Audience (r)

Taxonomy upgrade extras: 

  • Transgender
  • Posted by author(s)
  • Serial Chapter

Cigarettes Are A Girl's Best Friend

by slimv

 

Part 6

 

Carol spied Katie and Brent through the peephole as they sat in the glider underneath the porch light. The glow on her daughter's face spoke volumes. She couldn't help but smile as the young couple swayed back and forth on the glider serenaded by a chorus of crickets. The look of shared love on their faces was undeniable. Something important and meaningful had passed between them.

Carol fought the urge to open the door. Her heart was bursting with pride. She wanted to hug Katie. She wanted to cheer her on. Carol had battled her share of doubts and fears. There had been times when she had questioned the transition. Was becoming a woman really in Jimmy's best interest or had he just been going through a phase?

Carol was a beneficiary of the change. She had loved her son but had yearned for a daughter. The emergence of Katie filled a gap that completed her life. But had it completed Jimmy's? Two is company and three is a crowd, she thought as she strained her eye against the peephole. She saw Katie and Brent, but Jimmy was nowhere to be seen. That hadn't been the case until tonight.

She watched through the glass as Katie took a cigarette from her purse and held it to her lips. Without being asked, Brent fished a lighter from his pocket. Katie fixed her eyes on him as she steadied his hand in hers and cupped the flame. She accepted the light in the manner she had been taught.

Carol chuckled and shook her head as Katie leaned toward Brent and kissed him with smoke in her mouth. The expression on Brent's face was priceless. He was putty in her hands.

It was obvious to Carol that her daughter was no longer making the best of a bad situation. She wasn't reacting to Brent. She was purposely causing him to respond to her. She was the one in charge and she was clearly enjoying her power over him.

Carol had seen enough. There was no reason for her to continue this invasion of her daughter's privacy. She stepped away from the door but couldn't fight the urge to take one last peek. She looked again. They were kissing. Oh how sweet, she thought. She grudgingly pulled her self away and took a seat on the couch.

She picked up the Lady's Home Journal and lit a cigarette. She turned the pages but the words were a blur. They didn't compute. She was too blinded by thoughts of Katie and how happy she looked on the porch with Brent.

Happiness had eluded her son. As his mother, she had sensed his sadness and inability to fit in. Time and compassion might have healed some of his wounds but not all of them. Life is a crapshoot. Maybe he would have grown up and found a woman to share his life with, or perhaps not. Her son had been bullied. Those boys at Columbine had been bullied. That was not the destiny she wanted for her child. The irony of her Katie's relationship with Brent wasn't lost on her. He was the kind of boy who had made her son's life miserable but now he fawned over him. She smirked at the thought.

She looked up from her magazine as the front door opened and Katie stepped in, closing the door behind her. She pushed her blonde bangs away from her eyes and sighed when she saw her mother.

"Don't you look happy," said Carol. "Maybe Bobby and I should go to Stone Mountain and have a picnic."

Katie plopped down beside her on the couch. "We didn't go to Stone Mountain. We went to his family's lake house."

"My oh my," said Carol as she sat up straight. "You were alone with him? You look good so I guess you didn't have any problems."

"I told him I was on my period," said Katie as she lit one of her mother's cigarettes. "You were right. He didn't try to touch me down there."

Carol nodded as she searched the vibrant blonde for any signs of life from the insecure boy buried beneath her daughter's massive breasts. Jimmy had vanished without a trace. In his place sat Katie, who was suddenly more woman than girl. The maturity was more than physical. Any girl could look older with the right make-up and a cigarette. The beasts alone were enough to make a difference. But something else had changed.

Katie grinned at her mother as she tapped her cigarette over the ashtray. She leaned back and enjoyed the smoke as it entered and exited her lungs. She smoked it with the passion and confidence of a woman who knew what she wanted and had set out to get it.

"So, are you just going to sit there and torture me by making me guess or are you going to tell me why you're so happy? Something happened between you and Brent today, didn't it?"

Katie sighed joyously as she exhaled a lungful of smoke. "It was wonderful Mom. I never knew being a woman could feel this good. I never knew a woman could make a guy feel so good. I always thought boys like Brent had it made. When I was a boy I wanted to be just like him. I thought he was so big and powerful. It's not that way at all. I mean, sure, he's big and he's strong and he could wipe his ass with me, but he'd never do that. He can't do that. He loves me. I can make him do any thing I want him to do. I'm so little and he's so big but I'm bigger than him."

Carol took a drag from her cigarette and giggled. "Is this what it's all about. You finally realized how strong women are? I told you that in the beginning. Guys think with their with their penises and a woman can lead a man by his penis. I thought something else happened."

"It did Mom. Something else did happen. I sucked his cock today", she said proudly.

Carol gasped and choked on her smoke. "You did what? You had oral sex with Brent? You're kidding me, aren't you?"

Katie smiled knowingly at her mom as she leaned back against the couch cushions and pulled on her Virginia Slim. "He came in my mouth and it wasn't gross. It was beautiful. It's so weird. I don't know how to describe it. I liked the way it tasted but it's not like I would drink it by the glass or any thing like that. I liked it because it came from Brent. I think I love him Mom."

Tears of joy ran down Carol's cheeks as she devoured her daughter's happiness. She put her cigarette out and used both arms to embrace her. "Oh Katie. That's so wonderful. I'm so happy for you."

*****

Katie stood in front of her full-length mirror admiring how her waist length teddy clung to her curves. She lit a cigarette, puckered her lips and exhaled into the mirror. Her body felt electric. She quivered with delight as the silky fabric struggled to contain her bulging breasts. She held the cigarette to her cheek and swished her hips, cocked her head and absorbed her profile. She was so in love with her new self that she hardly noticed the tiny stiff penis ebbing and bobbing with her every movement. She blew her reflection a kiss and lay down on her bed underneath its frilly canopy.

With her cigarette clutched securely between her lips she looked forward toward the foot of her bed, hoping to see her self in the mirror, but her 36 G breasts rose like mountains on a plain, blocking her view. She placed both hands on top of the mounds and kneaded them with her fingers. She cooed at the sensation that radiated from her firm nipples.

Katie smoked like a train as her right hand wandered off her breasts, across her flat stomach and coming to rest on top of the nub her alter ego had once called a penis. She took the stiff nub between her fingers. She stroked and pulled it as she thought of Brent.

Oh how wonderful it would be she thought, if her penis were a vagina. She imagined Brent between her legs making penetration as she smoked beneath him. The ash grew longer with each puff she took. She knew it would fall and fall it did as it came to rest on her smooth neck. The ash was warm but not hot. She was making a mess but she didn't care. Each puff of smoke that entered and left her lungs along with each pull of her short-slender penis brought her closer to the ecstasy she craved.

What would Brent see if he looked down on her now? Smoke pouring from her flaring nostrils? Her eyes rolled back in her head? A grimace of pleasure glued to her face as, oh my God! The world collapsed like a soft pillow smothering her with an explosion of endorphins that coursed through her body from head to toe. She groaned as the feeling swallowed her whole. Her hand basked in the slick moisture of the hot sticky semen that flowed from her diminishing manhood.

She rolled to her side and put out her spent cigarette. As she did, her mountainous breasts collided with the mattress, giving her cause to giggle. She didn't bother to wipe up the mess though she knew it would dry to her sheets and teddy. She closed her eyes and thought of the last kiss she had shared with Brent as sleep stole over her.

 

Cigarettes Are A Girl's Best Friend

by slimv

 

Part 6

 

Carol spied Katie and Brent through the peephole as they sat in the glider underneath the porch light. The glow on her daughter's face spoke volumes. She couldn't help but smile as the young couple swayed back and forth on the glider serenaded by a chorus of crickets. The look of shared love on their faces was undeniable. Something important and meaningful had passed between them.

Carol fought the urge to open the door. Her heart was bursting with pride. She wanted to hug Katie. She wanted to cheer her on. Carol had battled her share of doubts and fears. There had been times when she had questioned the transition. Was becoming a woman really in Jimmy's best interest or had he just been going through a phase?

Carol was a beneficiary of the change. She had loved her son but had yearned for a daughter. The emergence of Katie filled a gap that completed her life. But had it completed Jimmy's? Two is company and three is a crowd, she thought as she strained her eye against the peephole. She saw Katie and Brent, but Jimmy was nowhere to be seen. That hadn't been the case until tonight.

She watched through the glass as Katie took a cigarette from her purse and held it to her lips. Without being asked, Brent fished a lighter from his pocket. Katie fixed her eyes on him as she steadied his hand in hers and cupped the flame. She accepted the light in the manner she had been taught.

Carol chuckled and shook her head as Katie leaned toward Brent and kissed him with smoke in her mouth. The expression on Brent's face was priceless. He was putty in her hands.

It was obvious to Carol that her daughter was no longer making the best of a bad situation. She wasn't reacting to Brent. She was purposely causing him to respond to her. She was the one in charge and she was clearly enjoying her power over him.

Carol had seen enough. There was no reason for her to continue this invasion of her daughter's privacy. She stepped away from the door but couldn't fight the urge to take one last peek. She looked again. They were kissing. Oh how sweet, she thought. She grudgingly pulled her self away and took a seat on the couch.

She picked up the Lady's Home Journal and lit a cigarette. She turned the pages but the words were a blur. They didn't compute. She was too blinded by thoughts of Katie and how happy she looked on the porch with Brent.

Happiness had eluded her son. As his mother, she had sensed his sadness and inability to fit in. Time and compassion might have healed some of his wounds but not all of them. Life is a crapshoot. Maybe he would have grown up and found a woman to share his life with, or perhaps not. Her son had been bullied. Those boys at Columbine had been bullied. That was not the destiny she wanted for her child. The irony of her Katie's relationship with Brent wasn't lost on her. He was the kind of boy who had made her son's life miserable but now he fawned over him. She smirked at the thought.

She looked up from her magazine as the front door opened and Katie stepped in, closing the door behind her. She pushed her blonde bangs away from her eyes and sighed when she saw her mother.

"Don't you look happy," said Carol. "Maybe Bobby and I should go to Stone Mountain and have a picnic."

Katie plopped down beside her on the couch. "We didn't go to Stone Mountain. We went to his family's lake house."

"My oh my," said Carol as she sat up straight. "You were alone with him? You look good so I guess you didn't have any problems."

"I told him I was on my period," said Katie as she lit one of her mother's cigarettes. "You were right. He didn't try to touch me down there."

Carol nodded as she searched the vibrant blonde for any signs of life from the insecure boy buried beneath her daughter's massive breasts. Jimmy had vanished without a trace. In his place sat Katie, who was suddenly more woman than girl. The maturity was more than physical. Any girl could look older with the right make-up and a cigarette. The beasts alone were enough to make a difference. But something else had changed.

Katie grinned at her mother as she tapped her cigarette over the ashtray. She leaned back and enjoyed the smoke as it entered and exited her lungs. She smoked it with the passion and confidence of a woman who knew what she wanted and had set out to get it.

"So, are you just going to sit there and torture me by making me guess or are you going to tell me why you're so happy? Something happened between you and Brent today, didn't it?"

Katie sighed joyously as she exhaled a lungful of smoke. "It was wonderful Mom. I never knew being a woman could feel this good. I never knew a woman could make a guy feel so good. I always thought boys like Brent had it made. When I was a boy I wanted to be just like him. I thought he was so big and powerful. It's not that way at all. I mean, sure, he's big and he's strong and he could wipe his ass with me, but he'd never do that. He can't do that. He loves me. I can make him do any thing I want him to do. I'm so little and he's so big but I'm bigger than him."

Carol took a drag from her cigarette and giggled. "Is this what it's all about. You finally realized how strong women are? I told you that in the beginning. Guys think with their with their penises and a woman can lead a man by his penis. I thought something else happened."

"It did Mom. Something else did happen. I sucked his cock today", she said proudly.

Carol gasped and choked on her smoke. "You did what? You had oral sex with Brent? You're kidding me, aren't you?"

Katie smiled knowingly at her mom as she leaned back against the couch cushions and pulled on her Virginia Slim. "He came in my mouth and it wasn't gross. It was beautiful. It's so weird. I don't know how to describe it. I liked the way it tasted but it's not like I would drink it by the glass or any thing like that. I liked it because it came from Brent. I think I love him Mom."

Tears of joy ran down Carol's cheeks as she devoured her daughter's happiness. She put her cigarette out and used both arms to embrace her. "Oh Katie. That's so wonderful. I'm so happy for you."

*****

Katie stood in front of her full-length mirror admiring how her waist length teddy clung to her curves. She lit a cigarette, puckered her lips and exhaled into the mirror. Her body felt electric. She quivered with delight as the silky fabric struggled to contain her bulging breasts. She held the cigarette to her cheek and swished her hips, cocked her head and absorbed her profile. She was so in love with her new self that she hardly noticed the tiny stiff penis ebbing and bobbing with her every movement. She blew her reflection a kiss and lay down on her bed underneath its frilly canopy.

With her cigarette clutched securely between her lips she looked forward toward the foot of her bed, hoping to see her self in the mirror, but her 36 G breasts rose like mountains on a plain, blocking her view. She placed both hands on top of the mounds and kneaded them with her fingers. She cooed at the sensation that radiated from her firm nipples.

Katie smoked like a train as her right hand wandered off her breasts, across her flat stomach and coming to rest on top of the nub her alter ego had once called a penis. She took the stiff nub between her fingers. She stroked and pulled it as she thought of Brent.

Oh how wonderful it would be she thought, if her penis were a vagina. She imagined Brent between her legs making penetration as she smoked beneath him. The ash grew longer with each puff she took. She knew it would fall and fall it did as it came to rest on her smooth neck. The ash was warm but not hot. She was making a mess but she didn't care. Each puff of smoke that entered and left her lungs along with each pull of her short-slender penis brought her closer to the ecstasy she craved.

What would Brent see if he looked down on her now? Smoke pouring from her flaring nostrils? Her eyes rolled back in her head? A grimace of pleasure glued to her face as, oh my God! The world collapsed like a soft pillow smothering her with an explosion of endorphins that coursed through her body from head to toe. She groaned as the feeling swallowed her whole. Her hand basked in the slick moisture of the hot sticky semen that flowed from her diminishing manhood.

She rolled to her side and put out her spent cigarette. As she did, her mountainous breasts collided with the mattress, giving her cause to giggle. She didn't bother to wipe up the mess though she knew it would dry to her sheets and teddy. She closed her eyes and thought of the last kiss she had shared with Brent as sleep stole over her.

 

Cigarettes Are a Girl's Best Friend -7-

Author: 

  • Slim V.

Audience Rating: 

  • EXPLICIT CONTENT

Taxonomy upgrade extras: 

  • Transgender
  • Fiction
  • Transitioning
  • Permission granted to post by author
  • Femdom / Humiliation
  • Tricked / Outsmarted

Cigarettes
Are A Girl's Best Friend

by slimv

 

Part 7 (Conclusion)

 

 

"What do you think of that one?" asked Carol as she pointed to the mannequin with her cigarette. I've always thought lavender was your color. What kind of corsage is Brent getting you? If he hasn't picked one out already, then maybe..."

"He has Mom. They're red roses with baby breath. They match the boutonniá¨re I'm getting him. I like that dress, but they probably don't have my size."

Carol laughed. "Well maybe you should have thought about that before you told Dr. Brown to give you those rubber baby buggy bumpers."

"Quit it Mom. I get enough grief from everyone else. I don't need it from my own mother."

"Sorry Dear. I'll try to do better. Let's go inside and have a look around. There's not a lot of room between the racks so watch out for your rack."

Katie sneered at her Mom as they entered the shop. She didn't see the helpful sales girl lying in wait. The girl took a direct hit in the face from Katie's gunnery, causing her head to snap back.

"Oh, I'm so sorry. Are you alright," asked Katie.

The sales girl was stunned but recovered quickly. "No problem," she said. "It happens all the time. So can I help you find something?"

"Yes, please," said Carol as she motioned to her own breasts. "We need to find a prom dress that will fit her."

The girl gave Carol a knowing nod. "Really? What school do you go to?"

"Well actually, its not my school," said Katie. "It's my boyfriend's. He goes to Gilmore."

"Me too," said the girl. "What's his name? Maybe I know him?"

"Brent Hathaway."

"No shit? Brent?"

"You know him," asked Katie?

"You might say that. We used to date."

"How awkward! Is this going to be a problem? We'd completely understand if you'd rather not help us. We can look ourselves." said Carol.

"It's no problem. It's just weird to finally meet you in person. I've heard so much about you from his friends." She lifted her hands to her breasts and pushed them up. "Apparently they weren't exaggerating."

"Oh by the way, I'm Cindy," she said extending her hand to Katie who took it. "Let me show you some dresses in the corner. They're kind of special. Most of our customers only dream of filling them if you know what I mean."

After picking several dresses, Cindy pointed Katie and her mom in the direction of the dressing rooms. She told Katie not to worry too much about the fit because if it was close she knew the name of a good seamstress who could do the alterations.

*****

"Holy fucking shit, said a pimply faced boy hidden in the back of the store with his eye to a camera. "That girl has a cock!"

*****

After paying for the purchases, Katie and her mother bought a couple of Cokes at the food court and took a break.

"Cindy is really pretty," said Katie as she lit a cigarette.

"She is, but she's not as pretty as you."

"But she's a real girl. I think that counts for something."

"You'll be a real girl too, and very soon I might add. Have you told Brent about the vacation?"

The vacation was Carol's cover story for her daughter's absence. They had told everyone that Katie was spending the summer in Portland with family.

Katie nodded. "He's pretty upset. He says he'll write me."

"You told him to use email didn't you? We can't have him sending real letters to some phony address in Portland."

"I'm not stupid Mom."

"Sorry."

*****

Carol opened the front door and invited Brent in, telling him how fabulous he looked in his black tux. He was holding a corsage consisting of small red roses and baby's breath as Katie predicted. She led Brent to the couch and sat down beside him.

"Katie will be just a minute," said Carol as she took a cigarette from her pack of Virginia Slims.

Brent's penis stirred as Katie's mom handled the cigarette between her fingers like a small baton. "Allow me," he stuttered as he retrieved the lighter from his pocket.

Carol smiled graciously and cupped the flame with her hand. Unlike her daughter, Carol tilted her head and exhaled away from Brent. "Katie was right. You are a gentleman."

Brent blushed nervously, hoping she couldn't read his mind or else she'd know what kind of pervert was dating her daughter.

Carol was an experienced woman. She was well aware of the effect her smoking had on men. Even so, she was amused by his response. Though it had been predictable, she still got a charge from it. She looked toward the stairs. Katie would be down soon. A part of her felt guilty for teasing her daughter's boyfriend, but that didn't stop her from seductively raising the cigarette to her lips as she asked about his plans for the evening.

He shuffled uneasily on the couch. His mind went blank. The name of the restaurant escaped him. Something warm and sticky trickled down his thigh.

"Coach and Six. We're going to Coach and Six."

"That's nice," said Carol. "It's one of my favorite restaurants- Katie's too." She knew what had happened but gave no indication. "I hope you made reservations for the smoking section."

"Oh yes Mrs. Higgins."

Carol smiled at Brent. "You're a good boy. Oh, I think I hear Katie," she said as she craned her neck toward the stairs.

Brent stood up when he saw her. A small stain had replaced his erection. He prayed neither woman would notice.

"You look great Katie. You're beautiful!" he said as he followed her breasts with his eyes as they bounded down the steps.

He wasn't exaggerating. She looked stunning in the dress Cindy had helped her pick out. If not for Cindy, she'd be wearing a halter to the prom. Not that Brent would have minded, but Katie wanted her first prom to be special.

"The roses are beautiful," exclaimed Katie!

Brent looked down at the corsage in his hand. He had forgotten all about it. He removed it from the box and began the arduous task of trying to attach it to Katie's dress without impaling her with the stickpin.

Carol watched with amusement as Brent struggled with the corsage. She could have assisted but opted not to. Katie could have helped too, but her mother hadn't taught her what to do in such a situation.

Brent turned red as he braced Katie's breast with one hand while pushing the pin through the lavender silk fabric. The tip of the pin finally poked through. "Did I stick you," he asked?"

Katie kissed him on the lips. "Uh-uh, you did it perfect. Look, no blood," she said as she pointed to her bosom. "Mom, can you get Brent's boutonniere from the fridge?"

"Sure thing," said Carol as she got off the couch, cigarette in hand, and went into the kitchen.

Brent tried not to stare as Carol's ass waltzed across the floor with a feminine wiggle.

She returned from the kitchen with the boutonniere and a camera. "OK guys and girls. It's picture time," she said as she handed the single rose to Katie for her to put on Brent. She snapped a picture of them as Katie fastened it beside his breast pocket. "That will make a great picture," she said.

"Over there by the fireplace, said Carol.

She posed them in front of the mantle, and stood back to take their picture, when another thought crossed her mind.

"Katie! I know what would make this picture perfect," she said excitedly. "Stay right there. Don't move a muscle- either one of you. I'll be right back."

She returned with a cigarette holder in hand. Katie grinned when she saw it. Brent's penis stiffened.

"Remember when I bought this for you," asked Carol? "It was right after I gave you permission to smoke," she said as she took a cigarette from her pack and inserted it in the silver barrel.

She handed the holder to Katie and asked Brent if he would do the honors by lighting Katie up."

"Cool," said Brent as he pulled out his lighter and held it steady so that Carol could take the picture.

Katie felt like a high fashion model as she followed her mother's directions as the camera flashed.

After the pictures were taken, Carol put the camera down. She hugged her daughter and warned Brent to drive carefully. She sighed as she remembered the magic of her first prom. Katie will remember this night forever, she thought.

*****

Their dinner had been delicious and full of conversation. Brent had never once taken his eyes off her. They talked about the dance, about who would be there and who the band was. They talked about Katie's upcoming vacation and how they would miss each other.

Brent lit Katie's cigarette and paid for their dinner with his father's credit card. He waited patiently for her to finish the cigarette. He didn't mind. He loved the way her lips looked when they were pursed with smoke.

She had developed quite a habit during their three-month courtship. He wondered if she could make the transition from home schooling to Gilmore where smoking was not permitted. It didn't seem fair to keep a girl like Katie apart from her cigarettes, he thought as he watched her smoke.

*****

Brent pulled up to the Ravinia's front entrance. After giving his keys to the valet, he offered his arm to Katie and they went inside.

Katie was wowed as they walked beneath the crystal chandelier as throngs of people walked past them on their way to places they had to go. A sign on an easel welcomed then to Gilmore's prom and they followed a crowd of students to the ballroom as Brent took the tickets from his wallet.

Everyone seemed to notice them. Katie had become accustomed to the stares. Brent beamed as she walked beside him attached to his elbow. He made small talk with the guys around him as they walked. Sometimes Brent would introduce her to one of his friends.

The ballroom was decorated with streamers. A mirrored disco light hung from the ceiling, casting reflections around the room as it spun to the music. The band was playing something from Matchbox 20. It was too loud for the room but Katie didn't mind. The deafening music added to the excitement. She felt like Cinderella at the ball with Brent as her prince.

They were standing by the refreshment table. Brent was holding two cups as a server filled them with punch from a ladle. She felt a tap on her shoulder and turned to see Cindy, the girl from the dress shop standing beside her.

Katie greeted her by name as she tried to speak over the music. "How do you like the dress," she asked?

Brent walked up beside her. She felt a cup being placed in her hand. He looked awkward and Katie wondered if the break-up had been as cordial as Cindy suggested.

The smile on Cindy's face was menacing. "It looks wonderful Katie." She turned to Brent and greeted him with the same menacing look. "The two of you make such a darling couple," she said.

Brent nodded and ushered Katie to an empty table, spilling a bit of punch on his tux in the process.

"What's wrong?" asked Katie as she put her purse on the table and took a seat beside him. "I thought you and Cindy were still friends."

"Where do you know Cindy from," asked Brent?

"She works at the dress shop. My mom and I met her when we were shopping. She helped me pick out this dress. I thought she was real nice."

"Yeah, real nice if you like rabid dogs. She hates my guts."

"She hates you because you don't date her anymore?"

"No, she hates me because I broke up with her after I met you."

"Oh," said Katie. "She didn't say that. She was so nice when I met her in the store."

"Let's not talk about it anymore, OK?"

Katie dropped the subject. The glass ashtray on the center of the table beckoned her. She looked around the ballroom to see if any of the other students were smoking. "Do you think it's OK to smoke in here," she asked?

"Sure," said Brent. "We're not in school.

"I don't see anyone else smoking."

"Over there," said Brent, as he pointed toward the corner. "I see Mrs. Warner and Miss Dobson smoking. It's OK. Go ahead."

"They're teachers though," said Katie as she removed a pack of Virginia Slims from her purse.

Brent lit Katie's cigarette and prepared himself for the blast of smoke from her lungs. He was breathing in her exhale as he felt a firm hand on his shoulder. He turned to see Dale Evers, Cindy's pimply-faced brother. Dale was a kind of a jerk as far as Brent was concerned, but he shook his hand as if they were long lost friends.

He introduced Dale to Katie and thought that would be the end of it.

"Are those real?" asked Dale, as he pointed to Katie breasts.

The offensive question caught Katie off guard and she answered him with a confused and hurt stare.

"Get the fuck out of here Evers."

"Don't get out of joint dude. I saw her at the dress shop when I was visiting Cindy."

"Well there you go you little perv," sneered Brent. "You shouldn't be hanging around women's clothes stores. Don't you have better things to do with your time?"

Dale returned the sneer. "Hey, you know what? You're right. I never should have brought it up. Katie, it was nice to meet you. Love the dress. Make sure you sit down when you piss so don't get it wet."

The gist of Dale's comment went unnoticed by Brent but made Katie shudder. She must have heard him wrong. She'd never seen Dale Evers in her life and there was no way he could know her secret. She thought of the dressing room. Had Cindy looked in while she was changing? She didn't think so. She would have noticed something like that. Besides, her mother had been standing guard. She took another puff from her cigarette and crushed it out in the ashtray.

"Wanna dance," asked Brent?

Katie nodded. They got up and she followed him out on the dance floor. Brent took her by the waist as she draped her hands around his neck. He nuzzled her while they moved to the music. He inhaled the sweet scent of smoke that clung to her hair and kissed her lovingly on the lips. She was receptive to his gesture and opened her mouth to receive his kiss. Although they were on a crowed floor, taste of her smoky kiss shrouded him in an invincible blanket of passion. Only when they pulled apart did they notice the laughter and the stares. But they were too caught up in the moment to understand their role in the crowd's amusement.

They sat back down at their table. Brent was lighting Katie's cigarette when Cindy and her brother Dale stopped by.

"Don't look now," said Cindy to Brent. "But here comes Mr. Clark and Ms. Ryan." She then turned to Katie and said, "I'd get out of here if I were you, but don't even think of trying to return that dress. We couldn't sell it now if we tried to give it away."

"What's she talking about," asked Katie? "Who are Mr. Clark and Ms. Ryan?"

"They're our school's principal and assistant principal," said Brent as he took a sip of his punch.

"Are you going to get in trouble because I'm smoking?"

"It's nothing. Don't worry. Cindy's just a jealous bitch."

Mr. Clarke and Ms. Ryan approached the table. The looks on their faces were both stern and uncomfortable. "Do you mind if we share your table," asked Mr. Clark?

Brent shrugged and Katie smiled nervously.

The pair of authority figures sat down. "Excuse me," said Ms. Ryan to Katie. "You don't look familiar and I pride myself in knowing all my students. Do you go to Gilmore?"

"Not yet," said Katie. But I will next Fall."

Ms. Ryan acknowledged Katie's answer with a nod and looked toward Mr. Clark who loosened his tie and cleared his throat.

"Brent, there are some things I'd like to discuss with you and your... um date. But first I need to ask if you're familiar with the school's policy in regard to same sex dating at school functions."

"What are you talking about," asked Brent?

"Not that Mr. Clark or myself agree or disagree with the policy," interrupted Ms. Ryan. "But we do have a responsibility to enforce the rules."

It was obvious to Clark and Ryan that Brent didn't have a clue as to what they were talking about or more importantly, why they had brought it up. His date, on the other hand, was showing clear signs of being under stress as she puffed furiously on her cigarette.

"This is very embarrassing," said Mr. Clark, "But it's been brought to our attention that your date is not really a female. If this is true, it would violate our school's policy on same sex dating at school functions."

Brent laughed. "What? You think Katie is a guy? Did Cindy Evers and her dumb ass brother tell you that? Cindy's just mad cause I broke up with her after I met Katie. She's a stupid jealous bitch."

"Please tone down your language Brent. We can get to the bottom of this quickly and quietly if your date will accompany me to the lady's room," said Ms. Ryan.

Brent was incensed. "You want to strip search my girlfriend because my ex-girlfriend hates my guts and has 'suggested' that Katie isn't a girl. This is insane. You're insane."

"It was more than a 'suggestion'. It was an accusation and a convincing one at that," said Mr. Clark.

"Just take me home," cried Katie. "I don't want to be here anymore. Please Brent. Let's just go."

Brent slammed his forearm on the table. The band had quit playing as people gathered around the table to get a better look at the scene as it unfolded. The sound of his arm against the table reverberated across the dead air as punch spilled from his cup, staining the white tablecloth.

Brent and Katie found themselves in the center of a full-blown scene and it was not the kind of attention that either of them wanted.

Katie bolted. She grabbed her purse and stumbled through a jeering crowd that laughed at her pain. The band started back up with the most appropriate song they could think of- 'Lola' by the Kinks.

I met her in a club down in old soho

Where you drink champagne and it tastes just like cherry-cola...

 

The crowd screamed 'Fag!' and grabbed at her breasts. Her high heels gave out under her feet and she fell to the floor. A strong hand hooked under her arm and pulled her to her feet. It was Brent. The crowd turned on him, shouting 'Brent is a homo' and 'Brent is a fag'. He hustled her to the exit as they were pelted with cups and plastic plates.

She walked up to me and she asked me to dance

I asked her her name and in a dark brown voice she said lola

L-o-l-a lola lo-lo-lo-lo lola

 

The crowd stopped at the door but their mocking and the band's music followed them as Brent shoved his ticket into the valet's hand. Katie sobbed uncontrollably and he tried to comfort her.

Well I’m not the world’s most physical guy

But when she squeezed me tight she nearly broke my spine

Oh my lola lo-lo-lo-lo lola

Well I’m not dumb but I can’t understand

Why she walked like a woman and talked like a man

Oh my lola lo-lo-lo-lo lola lo-lo-lo-lo lola

 

He didn't know what to say as he drove toward her house. It had all happened so fast. The crowd, his friends, they had all turned against him. He told her they were all fucking assholes, as if his condemnations would make her feel better. He told her how sorry he was. He swore he'd get even with Cindy and that he'd kick Dale's ass. His father knew lawyers. They'd sue the school. They'd sue Mr. Clark and Ms. Ryan.

Katie became hysterical as Brent pulled up her driveway. Her worst nightmare had come true. Her secret had been revealed in the worst possible way. Not only had she ruined her life, but she had ruined Brent's as well.

"I'll kill them," shouted Brent as he turned off the engine. "I'll kill them all! Those fucking liars!

"It's true," said Katie. Her words were soft but audible. By saying them she had put her life in jeopardy. But in that moment, her life lacked value.

"Don't bullshit me like this. That's the last thing I need right now. This isn't funny."

"That summer vacation I'm supposed to take next week in Portland, I'm not going to Portland. I'm going to the hospital. I'm getting castrated and they're giving me a vagina. I was born a boy, but it was a mistake. I should have been a girl. The doctors are going to make it right. They're going to fix me. I'm so sorry Brent. I should have told you before but I didn't know how. I never thought anything like this would happen. I would have died before I let anything like this happen. I'm so sorry. It's not your fault. You're not gay. You didn't know."

The whole world had gone insane! It wasn't just back at the hotel. It was in this car as well. His anger swelled. He felt nauseous. Why was she saying this? Could it be true? He had kissed her. He had sucked her tits. She was a girl, wasn't she? She had touched his dick. She had sucked it for Christ's sake! He didn't want to believe a boy had made him cum. But why would she say it if it wasn't true?

"I love you," said Katie.

She leaned toward him and tried to kiss him. He pushed her away. She told him she was sorry as she opened the door. He didn't walk her to the door. He didn't wait to see her safely inside. He started the engine and revved it with his foot. He pulled the gearshift down. The tires squealed as the car raced backwards down the driveway.

The mailbox collapsed under the weight of the car's rear bumper with a crash that shattered the morbid silence of the night air. Katie watched the sparks fly from Brent's bumper as his car screamed out of the neighborhood, dragging the mailbox behind it.

*****

Despite the tragedy at the prom, Carol convinced her daughter to proceed with the surgery. She took responsibility for what had happened. Things would have turned out differently if she had encouraged to Katie to be honest with Brent about her condition. But then again, if she had been honest, Brent never would have accepted her, even if his acceptance had only been temporary and built on a lie. The dishonest transaction of misguided trust had given her daughter three months of bliss. But what was the cost of that bliss? Lives and reputations had been ruined.

The surgery had been painful. Katie's body felt like an open wound. She had few visitors other than her mother and Dr. Doyle. Bobby had broken up with her mother after news of the prom incident rocked his church. He hadn't even sent her a get well card.

She was glad to be out of the hospital. Recovering at home hadn't been pleasant but at least she didn't have to face the nurses who looked upon her with curiosity veiled with mock concern. Her mother had put the house on the market. Atlanta was a big city, but her notoriety had outgrown the small bedroom community. There had been lookers but as of yet no contract had been signed.

Time heals all wounds- so said her mother. It had been almost three months since the surgery and she had physically healed. Life goes on- so said her mother. Katie refused to leave the house. She spent most of her time in her bedroom smoking cigarettes and watching TV. The friends she had known as Jimmy were now aware that their old friend had not moved away, but none of them came to see her. As far as they were concerned, Jimmy had died and Katie was someone they didn't want to know.

School was scheduled to begin next week. She would watch the neighborhood kids from her window as they got on the bus. Her mother would continue home schooling her until they could sell the house and move to a new place- a place where no one had ever heard of Jimmy or Katie Higgins.

She took a final cheek hallowing drag from her cigarette and it crushed it out in the overflowing ashtray that sat beside her bed on the nightstand. She noticed the orange nicotine stains that covered her fingers but didn't care. Good hygiene had gone out the window. Smoking had lost its glamour. All that was left was the addiction. Since she spent most of her time as a prisoner in her own bedroom, it had become like one huge ashtray. Her dresser, once stark white had yellowed under the build up of tar that rained down on it. She knew she smoked too much but she didn't care. She didn't care about anything. She cuddled her pillow and stared at the canopy that spread across her bed and closed her eyes.

She awoke to the sound of knocking and the voice of her mother asking to come in. Katie groaned and rolled away from the sound of her mother's voice as the door creaked open.

"You have a visitor," said Carol. "I'll just leave the two of you alone now."

A visitor, thought Katie. How odd. She yielded to her curiosity and rolled over toward the door. The visitor was Brent. She gasped and sat up. She was torn by competing feelings of love and fear. Why had her mother let him in? But it was only appropriate that her life should end like this- by Brent's hand.

"How are you feeling," he asked?

She detected no sign of anger in his voice.

"It's over. I'm better. At least that's what they tell me."

"I've been thinking about you," said Brent. "I'm sorry I haven't visited before now, but things have been kind of crazy since the prom."

"I didn't expect to see you at all after what happened. I wanted to call you or at least write you. I wanted to tell you how sorry I am but I was afraid I'd just make it worse."

"It's probably best that you didn't," said Brent as he took a seat on the bed beside her. "I'm not going to lie. I hated you for a long time. Every one laughs at me. They think I'm a fag. Even my own dad looks at me funny."

"I'm so sorry Brent. It wasn't your fault. I should have told you."

"So why didn't you."

"You don't want to know. It would just make things worse."

"Oh no. You're not getting off that easy Katie- or whoever you really are. You changed my life and I think I deserve to know why. That's why I'm here."

"I didn't tell you because I was in love with you. I was so stupid. I thought no one would ever know and this sounds so dumb but I thought we would live happily ever after like in some stupid fairytale."

Brent nodded as he listened to her explanation. That's what my mom said too."

"I bet your parents are pretty pissed at me."

"Dad is still scratching his head but mom understands. She and I talk a lot. She thinks I'm in love with you."

"I'm sorry," said Katie as she reached for her pack of Virginia Slims and lighter. She placed the cigarette between her lips and was about to light it when Brent stopped her with his hand.

"Let me," he said as he took the lighter from her. Katie said nothing as she accepted the light.

"I think my mom's right," said Brent. "I think I love you."

Katie turned to him, her big doe eyes moist with tears. "Oh Brent, please don't torture me like this," she pleaded as little puffs of smoke punctuated her words.

He pulled her toward him. She didn't resist. His breath was hot against her cheek. She reeked of smoke, just as he remembered. She whimpered as his soft lips met hers. She threw an arm around his broad shoulder and ran her hand across his muscled back as the cigarette continued to burn between her fingers.

He pushed her gently to the mattress. Her breasts rolled like the crest of a wave as it crashed against the beach. He unbuttoned her shorts and pulled them off as she helped by extending her legs. Her panties were the next to go. He stripped them off and dropped them to the floor beside her shorts.

He knelt before her and absorbed the beauty of her finely crafted vagina. Although he hadn't seen many, he saw nothing that indicated a difference between Katie and any other woman. A thick mound of coarse blonde hair covered it. Her pink lips glistened with the moisture of her excitement.

He swung a leg off the bed and caught his balance as he unbuckled his belt. His pants and underwear fell in a pile next to hers.

She stared lovingly at his raging penis as she engorged her lungs with smoke from her cigarette. He took it from her and put it out in the ashtray. Without asking if she wanted one, he took another cigarette from the pack and gently placed it between her lips and lit it.

He climbed back on the bed and straddled her as she wiggled into position beneath him. The smoke from her lips met his and he inhaled her gift as pushed his hips down.

She felt the tip of his penis as it tickled and teased the sloppy wet lips of her vagina. She reached between his legs and guided him home with her hand.

Brent groaned with pleasure as his penis entered the doorway of her soul. She gasped beneath him as smoke billowed from her mouth to his face. She took him inside one inch at a time, slowly until he filled her with his girth.

The instinct of the nature buried deep within her since birth came forth as she ground her hips into his, slowly, forcefully and with rhythmic precision. Every thrust of his hips sent his penis colliding against her sensitive clitoris. She smoked frantically as she fought to keep pace with his fast approaching orgasm. She was the first to cross the finish line. She held the smoke in her lungs as her body quivered and trembled in ecstatic ecstasy. He reared his head back and followed her as the nails from her fingers ripped into the flesh of his ass.

He collapsed next to her, breathing rapidly, covered in the sweat of his passion as she blistered his neck with hot kisses. She pulled his face to her breasts and cradled his head with one hand while putting her cigarette out and lighting a new one. He nuzzled her and mumbled promises of love as she responded with smoky kisses.

 

Fin.

(I have written several other smoking/TG stories that are available at Sapphire's Place and some straight smoking stories that are available at Smoking From All Sides)


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