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Judy sat across from her mother at the table, eating her breakfast. Her mom sipped her coffee while watching her daughter. It was easy to see something was bothering her.

“What’s up? You look upset about something,” Betty said.

Judy shrugged her shoulders as she stared into her bowl of cereal. Betty waited a moment and said, “Well, you’re clearly upset.”

“My life sucks!” Judy said.

“What happened now?”

Betty had listened to her daughter complaining about things for the past few years. She knew Judy suffered from low self-esteem and was unhappy with her appearance. Since she started high school, Judy whined about the fact none of the boys she knew ever asked her out.

Judy wasn’t homely, but she wasn’t pretty either. Her round face, pudgy nose, and thick dark wavy hair made her look unattractive, at least in her eyes. She also carried a few extra pounds. In school, the other kids teased her and made fun of the way she looked.

“I went to a party with Kim last Saturday night. Everyone was making out and having fun. As usual, no one paid any attention to me. I sat in the corner, watching like a bump on a log.”

Betty nodded and said, “As I’ve said before, you have to be more outgoing. Boys aren’t going to ask you out if you sulk all the time.”

Mark sat in the living room, putting on his work boots. He shook his head as he listened to his sister’s harping about her lack of a social life. Like their mother, he’d heard it before, and it was becoming exhausting.

“I don’t sulk, Mom. Do you know I’ve never been on a date? Do you know I’ve never made out with a boy or had one feel me up? I’m going to be nineteen,” Judy said. Her anger was apparent.

Betty nodded and tried to be empathetic, but she was tired of hearing about her daughter’s woes. “I don’t know what to tell you, Judy. Do you really feel the fact you haven’t made out with a boy is a problem?”

“Yes, I think it’s a big problem.”

Shaking his head, Mark got up from the couch and walked into the kitchen. He moved to his sister, tilted her head back, and pressed his mouth to hers. When Judy gasped, her brother shoved his tongue into her mouth. He put his hand on one of her breasts and gently kneaded her full mound.

Standing up, Mark chuckled and said, “There, problem solved! I’m going to work,”

Betty laughed as she looked at her daughter sitting with her eyes and mouth wide open.

“MOM! Don’t laugh at me. Did you see what Mark did? He kissed me and grabbed my boob!”

It took a moment for Betty to regain her composure. She continued chuckling and shook her head.

“Yes, I saw what your brother did.”

“You’re going to say something to him, aren’t you? You should ground him!” Judy said.

“Judy, your brother’s almost twenty-one. No, I’m not going to ground him or say anything to him. You two have to work this out between you.” Betty smiled. “It isn’t the end of the world, you know.”

“He grabbed my boob!” Judy repeated.

“Well, you were complaining about the fact no one ever felt you up before. Besides, what did Mark feel? You’re wearing a shirt and a bra.”

“He’s my brother and brothers aren’t supposed to do things like he did to their sisters. How would you feel if Uncle Bob did it to you?”

“Honey, your Uncle used to do things like your brother did when we were younger. Do you remember when you got your first bra?” Judy nodded. “Do remember your brother snapping your bra strap?”

“Yes, but I was only eleven and didn’t really have breasts.”

“True, but you sure took great pride in prancing around the house in your training bra. You wanted everyone to know you wore one,” Betty said.

Grinning, Judy nodded. She remembered how she would walk around in her bra whenever she could after she received it. Mark took great joy in snapping her bra strap and making comments about her ‘bee stings.’

Judy calmed down and drank some of her coffee. “What did Uncle Bob do to you?”

“He snapped my bra strap and grabbed me when he could. When we used to wrestle, he grabbed my breasts every chance he got,” Betty said. She chuckled again. “Frankly, I’m surprised your brother never tried anything with you when you two were younger.”

Shaking her head, Judy said, “I guess he’s like every other boy and thinks I’m disgusting.”

Betty saw tears forming in her daughter’s eyes. “Maybe your brother cares about you and wouldn’t do anything to hurt or upset you.”

Judy shrugged her shoulders. She took her dishes to the sink, rinsed them, and put them in the dishwasher.

“We better get going, so we’re not late for work,” Judy said.

Betty got up and followed her daughter to the car. She drove to the office where the two of them worked. Betty’s brother Bob owned a construction company. She and Judy worked in the office. Mark worked as a carpenter for the company.

As she drove, Betty thought about her teen years and her brother. She and Bob grew up on the family farm. Their parents made a decent living, but farm life was hard and not something she or her brother wanted to do for a living.

After graduating from high school, Bob joined the service. When he got out, he went to work in construction. Judy met Frank in high school and married him as soon as they could after graduation. Six months after the small wedding, Mark was born. Like her family, Frank’s family farmed. They lived with Frank’s parents for a few years but left after Judy was born.

Frank found a factory job in the city, and they rented a small house. Things went well for the next five years, but then Frank started an affair with a woman he met at the factory. The marriage lasted about another year before Betty packed up her kids and moved. Bob helped her find a house and gave her a job at his new company.

Judy stared out the window. She thought about what her brother did, but also what her mother said.

“What did you do when Uncle Bob felt you up?” Judy said.

Smiling, Betty said, “Nothing really. It wasn’t a big deal.”

“Did you two ever fool around?” Judy asked.

Betty took a deep breath and thought about her answer. “Uncle Bob and I were close when we were your age, but we never did any more than what I told you. After high school, he joined the service and left the farm. I got married as soon as I got out of school.”

Judy was about to press the issue, but her mom pulled into the parking lot. She quickly got out of the car and walked toward the building. Judy opened her door and got out, tugging her shorts down.

Betty went to her desk, put her purse in a drawer, and went to get coffee. With her cup in hand, she went to Bob’s office to tell her brother good morning.

Bob got up from his desk and greeted his sister. She moved closer to him and said, “You wouldn’t believe what Mark did this morning,” as she hugged her brother.

Bob laughed as Betty told him about the exchange between Judy and Mark. By the time she finished, she was laughing too.

“What did Judy do after he did it?” Bob said.

“Once she got over the shock, she told me I should ground Mark.”

Bob was well aware of Judy’s issues. Betty talked to him about her daughter often, depending on her brother to offer his opinion.

“I told Judy it wasn’t the end of the world. She asked me if we ever fooled around when we were younger.”

Smiling, Bob said, “What did you tell her?”

“I told her you used to snap my bra strap and grabbed my tits when we wrestled.” Betty laughed. “I didn’t mention I encouraged you.”

Bob put his hand on his sister’s ass, gave her a squeeze, and said, “You still do.”

“Yup, and you love it,” Betty said. She put her hand between his legs and massaged him.

Making sure no one could see them, Bob and Betty shared a tender kiss.

“We better get to work before someone sees us,” Bob said.

Betty nodded and said, “I know, but you know what I’d really like, don’t you?”

“No more than I do. Maybe we can get together tonight. I’ll take you to dinner.”

Smiling, Betty nodded. “Dinner sounds great.” She rubbed his crotch. “I’ll have you for dessert.”

Bob and Betty chuckled and then separated. He returned to his desk, adjusting himself before sitting down.

Betty left her brother’s office and went to her desk. She began going over the accounts payable, preparing them for payment. She glanced at her daughter, watching her answer the phones.

When it was time for lunch, Judy and Betty went to the break room. They sat at a table eating the salads they brought from home. Like most days, they were alone in the office. Bob left earlier to visit a couple of the job sites.

“Are you still upset with your brother?” Betty said.

Judy shrugged her shoulders. “I don’t know if I am or not. I still can’t believe the pervert grabbed my boob.”

Betty tried not to chuckle. “I think you’ll live. Don’t do anything stupid.”

“Like what?”

“Yelling at Mark won’t serve any purpose. If I were you, I’d forget it,” Betty said.

Judy nodded and picked at her salad. She thought about what happened and started smiling. When Betty asked what she found funny, Judy said, “You’re right, it isn’t the end of the world. My brother has always been a jokester.”

“Maybe he got tired of listening to you complain. You’ve been bitching about the way you look and the fact no one asks you out for years. What happened to the boy who took you to the prom?”

“Greg?”

Betty nodded. “You said you had a nice time when he took you.”

“It was okay, but it didn’t turn out the way I planned,” Judy said.

“Why? What did you have planned?”

Shrugging her shoulders, Judy said, “I kind of thought he would ask me out again. I thought he liked me. It turned out he took me because he wanted everyone to think he’s straight.”

Judy didn’t tell her mom she found out Greg was gay until after the dance. She hoped he would take her parking and they would fool around. Three months before the prom, she went to the clinic to get a prescription for birth control. Had things worked out, she wouldn’t be a virgin.

By the end of the day, Judy was over being upset with her brother. She decided she wouldn’t yell at him as she’d planned.

“I’m going to dinner with Uncle Bob tonight,” Betty as she drove home after work.

“Maybe I’ll call Kim and see if she wants to do something,” Judy replied.

“If I don’t see him, let Mark know what’s going on. I think his crew is working overtime tonight.”

Judy nodded. “I’ll text him before I go out.”

When Betty and Judy arrived home, they went into the house to get ready. Judy called her friend Kim and agreed to meet her at a local restaurant. She went to her room and started getting ready to go out.

After removing her clothes, Judy went to her bathroom to shower. As she washed her breasts, she chuckled, remembering what her brother did to her. Everything happened so fast she didn’t realize what her brother did until he was walking out the door.

Judy dressed and fixed her hair. She applied her makeup and headed to the living room. Walking to the other side of the split ranch house, she tapped on her mom’s bedroom door.

Betty opened her door, and Judy said, “I’m taking off. I texted Mark and told him we weren’t going to be home for dinner.”

“Thanks, have a good time. I’ll see you later,” Betty said.

Judy met her friend, Kim at the restaurant. They found a booth and sat across from one another. Kim told Judy about her job, saying how much she liked working at the department store. Judy talked about her work and the things she did for her uncle’s company.

“So, how’s your cute brother doing?” Kim said.

“Mark is fine. He’s a jerk as usual. You wouldn’t believe what the pervert did to me this morning,” Judy said.

“What did he do?” Kim asked between bites of food.

“I was sitting at the table talking to my mom. I told her about the party and how no one paid any attention to me. Mark came into the kitchen, kissed me, and grabbed my boob,” Judy said.

Kim laughed and said, “Brothers can be grabby, can’t they?”

“I don’t know. It was the first time Mark ever did anything like that to me. He snapped my bra strap when I started wearing one, but it was years ago. Mom said her brother used to grab her boobs when they goofed around. Has your brother ever felt you up?”

Shrugging her shoulders, Kim smiled and then nodded. “Dave was the first boy to touch my breasts. He thought it was funny to come up behind me and grab them.”

“Really? What did you do?”

“I’d call him a pervert and act as if I didn’t like it.”

“Did you like it when he grabbed you? Isn’t it weird to have your brother feeling you up?”

Once again, Kim shrugged her shoulders. She thought about her relationship with her brother but didn’t reply to Judy’s question. Like Judy, Kim harbored issues with her appearance. She was chubby and felt boys wouldn’t find her desirable. When her brother started fooling around and touched her breasts the first time, Kim admonished him. She yelled at Dave, but he just laughed.

Changing the subject, Judy said, “I’m so fed up with being alone. I want a boyfriend and to do things. I’m tired of feeling the way I do.”

“If you want things to change, you have to change them. You don’t look bad, Judy. If you changed the way you dress, and the way you act, you’d get asked out.”

“What do you mean, Kim? What’s wrong with the way I dress?”

Kim looked across the table and took a deep breath. “Can I be honest with you?” Judy nodded. “You dress frumpy. Your tops hide your boobs, and you never wear tight pants or flattering clothes.”

“I know, but if you looked like I do...”

“Shit, Judy, you look better than I do,” Kim said, cutting Judy off. She didn’t want to listen to her friend’s endless diatribe about the way she looked or thought she looked.

“How can you say I look better than you do? You get asked out all the time. I saw you making out with Ted at the party. I think I was the only girl who didn’t have someone hitting on her.”

Kim didn’t want to tell Judy why she didn’t have trouble finding a boy to make out with her. She knew it was because of her willingness to fool around with a boy, even if it was the first time she went out with him. Her relationships didn’t last long, but she had fun.

“What did you expect? You can’t stand around with your arms folded over your chest and expect anyone to approach you. Your body language says, ‘stay away.’

“I don’t do that! Do I?” Judy said.

Nodding, Kim said, “Yes, you do. You show up wearing a pair of jeans, a size too big. Your top covered you to your neck and hung on you like a sack. Look, if you ever want to update your wardrobe, let me know. I’ll take you shopping and help you.”

Judy thought about what Kim said. She didn’t feel the way she dressed was frumpy, as her friend said.

“You can’t go to a restaurant and expect the server to know what you want. You have to tell them. Boys are the same way, they can’t read your mind,” Kim said.

“What do you expect me to do, walk up to a boy and ask him if he wants to fool around?” Judy said.

“That’s one way to do it. There are other things you can do and not be too abrupt. The first thing you have to do is talk to them. If you want to meet a boy, talk to him, and see where it goes.”

Kim went on, telling Judy how to flirt. Judy listened but found it hard to understand what Kim said.

“So you’re telling me if I’m interested in a guy I should tell him?” Judy said.

Kim smiled and said, “If I find a boy I want to know better, I start talking to him. If he seems interested in me, I let him get a peek down my top and touch him while we talk.”

Judy laughed and said, “I’m not brave enough.”

“You know what they say, it pays to advertise. If you want boys to notice you, you have to do something about it.” Kim paused and smiled. “Do you remember the rumor about me when we were in the eleventh grade?”

Judy nodded. The buzz was Kim went out with a boy she let feel her up and gave him a blow job. When Judy asked, Kim denied it.

“Well, it was true. I figured the only way to get boys to like me was to let them have some fun. After the word got out, I started getting asked out,” Kim said.

“Wow, I never knew. Did you fool around with all the boys you went out with?” Judy asked.

Grinning, Kim said, “Not all of them, but I did give some of them what they wanted.”

“Do you like doing it, you know, giving them blow jobs?”

“I love it,” Kim replied. She chuckled and added, “I like screwing too.”

“You’ve gone all the way?” Kim smiled and nodded. “With who?”

“I’ve done it a few times. I’m not going to say who, but I will tell you it gets better all the time.”

Judy sat quietly, thinking for a moment. She sighed and said, “I’m not going to do things with a boy just to get a date. I guess I’ll have to be happy with taking care of myself.”

Kim shrugged her shoulders and said, “Suit yourself. If you ever need any advice, let me know.”

Judy sat silently for a few moments. “Do you really think I dress, frumpy?”

“Honestly, I think you dress the way you do because of the way you see yourself. Judy, there’s nothing wrong with the way you look or your body. If you want other people to like you, you have to like yourself first,” Kim said.

“What would you suggest?” Judy asked.

Smiling, Kim said, “If you’re looking for a complete makeover, you have to start at the core. I’ll bet you’re wearing an everyday white bra and granny panties.”

“So, who’s going to see my underwear?”

“It all depends on whether or not you plan to get lucky. If all you want to do with a boy is kiss him, and maybe let him touch you through your clothes, it doesn’t matter. If you want to do more, it turns a boy on when he sees a girl in sexy undies. I like them because they make me feel better about myself.”

“Okay, what else should I do?” Judy said.

Kim chuckled and said, “Do you trust me?”

“Sure, you’re my best friend. What do you have in mind?”

“That depends on how much money you have and are willing to spend,” Kim replied.

Judy thought for a moment, smiled, and said, “I have money. As far as how much I’m willing to spend-it depends on what.”

“We’ll figure it out as we go. Let’s get out of here. We’ll go to the store where I work. You can get my discount,” Kim replied.

Judy and Kim left the restaurant and went to the department store where Kim worked.

Kim led her friend through the store to the lingerie department. She pointed at the racks, telling Judy what she liked to wear.

Judy stood near Kim, looking at the sexy bras and panties she showed her. When Kim held up a lacy thong, Judy shook her head.

“Those look uncomfortable,” Judy said.

“You’d be surprised, Judy. I wear them all the time. It took a little getting used to, but now they don’t feel weird at all. You can buy a pair and see if you like them. If you do, get more. If not, you can always wear your granny panties,” Kim said.

“Don’t be a brat, Kim. I guess I never thought too much about my undies,” Judy said.

“Well, the new Judy needs to think about these things,” Kim said. She laughed and snapped Judy’s bra strap. “What size bra do you wear? We can start putting together sets of sexy undies for you.”

“The last time I bought one, it was a thirty-four C,” Judy said.

Kim sorted through several bras on the rack. She looked at one, put it back, then selected a few others. Grabbing Judy’s arm, Kim led her to the dressing rooms.

“Try this on,” Kim said after sliding the curtain closed.

“Um, okay. Are you going to wait outside?” Judy said as she unbuttoned her blouse.

Laughing, Kim shook her head. “They’re just tits, Judy. You have to get over your shyness.”

Holding her blouse closed, Judy said, “I’ve never been comfortable undressing in front of anyone. When I had to change for physical education, I would keep my towel wrapped around me. I put my bra on over the towel, then pulled it out.”

“A lot of the girls did, Judy.”

Judy laughed and said, “Unlike you, I was shy. You didn’t mind flashing your goodies for everyone to see.”

Kim shrugged her shoulders. She reached for Judy’s blouse, helping her friend take it off. After hanging the garment on a hook, Kim looked at her friend, then began chuckling.

“Is this the bra you were wearing when Mark grabbed your boob?” Kim said. Blushing, Judy nodded. Kim poked her finger against the molded cup. “He sure didn’t get to feel much. This thing is like armor.”

Kim reached around Judy and released her bra. Gasping, Judy quickly crossed her arms over her breasts.

“Try this one on, Judy,” Kim said as she handed Judy one of the bras.

Keeping one arm over her breasts, Judy took the bra from her friend. Turning her back, she put on the sheer garment. Judy tugged at the cups, adjusting them on her breasts. When Judy turned around, Kim nodded.

“This one looks good on you. How does it feel?” Kim said.

Gazing at her reflection in the mirror, Judy was shocked by the fact she could see her areola and nipples through the red transparent material. The bra formed to her firm breasts like a second skin.

“This bra is different from any I’ve worn before.” Judy twisted and turned as she looked at herself in the mirror. “I feel like I’m almost naked.”

Kim snickered and handed Judy another bra. When she put on the second garment, she was less shy. Judy tried on all of the bras Kim selected, deciding she liked all of them.

After Judy redressed, the two girls left the changing room. They went back to the racks to find a few more bras. Kim selected matching panties while Judy followed her.

“Okay, we have new undies for you. Now we need to get skirts, tops, shorts, and pants,” Kim said.

By this time, Judy had given in and didn’t protest while her friend selected a new wardrobe for her. As the girls picked out new items, and Judy tried them on, she began to relax. When Kim showed her short skirts and dresses, Judy didn’t protest, adding a few to her other things.

Judy paid for her items, then the girls took the things to the car. Judy opened the trunk, placed the packages in it, then closed the lid.

“Would you like to get something to drink?” Kim said.

“Sure, where do you want to go?” Judy replied.

Kim suggested a coffee shop they would pass on their way home. Kim went to get her car, telling Judy she would meet her at the coffee shop. Judy got into her car, smiling as she thought about the shopping trip with her friend. For the first time in her life, she felt good about the clothes she purchased. In the past, shopping was out of necessity, not to change the way she planned to start dressing.

As she drove to the coffee shop, Judy couldn’t help thinking about the new underwear she’d bought. The sexy bras, lacy panties, camisoles, and leggings were different from anything she owned or even considered wearing in the past.

Kim and Judy arrived at the coffee shop at the same time. They went in, ordered their drinks, and found seats in the corner of the room. They shared a couch, placing their cups on a table in front of them.

“Okay, what do you think about what you bought?” Kim said.

“I don’t know, not yet. My new things are a lot different from anything I’ve ever worn before,” Judy replied.

“I think everything looked good on you, Judy.” Kim smiled. “I guess this is the first step in the ‘get Judy laid’ project. Now we have to find you a man.”

“Kim, don’t make it sound so sluty. I want someone, but not just to have sex,” Judy said. She picked up her drink and took a sip.

“I know. I’m just teasing you, Judy. There’s nothing wrong with sex. In fact, it’s fun,” Kim said.

“Don’t get me wrong, I want to have sex, Kim. I don’t want to do it just to do it though. Shouldn’t it be something special?”

Kim smiled, then she nodded. “It should be someone you like at least. I wasn’t suggesting you jump into bed with the first boy who hits on you.”

Judy laughed and said, “I wouldn’t know what to do if I did want to have sex.”

“Learning is part of the fun. Don’t worry, it’ll come naturally. If I can offer a suggestion, don’t prejudge anything about sex. You have to try things to decide whether or not you like them.”

Judy nodded. She thought for a moment, then said, “Who did you learn with?”

Smiling, Kim said, “I’m still learning.”

“You know what I mean. Who was the first guy you did anything with?” Judy chuckled. “I mean other than your brother grabbing your boobs.”

Kim thought for a moment. “I think you’re going to look great in your new clothes, Judy.”

Judy looked at Kim. She realized her friend wasn’t going to tell her any more about her sex life than she already had.

“We’ll see. Maybe next time we go to a party, the boys will pay attention to me,” Judy said.

“You know it’s more than what you wear, don’t you? Like I said before, you can’t stand around with your arms folded over your chest and expect a boy to come on to you. You have to let them know you’re interested,” Kim said.

Judy nodded while mulling over what her friend said. If she were honest with herself, Judy knew Kim was right about her body language. She did stay away from the other kids and didn’t make eye contact with the boys.

Kim and Judy talked about several things, but sex wasn’t part of their conversation. After finishing their drinks, the girls left the coffee shop and headed home.

Judy took her packages into the house and to her bedroom. She tossed the bags on her bed and went to see if her brother or mother were home. Finding the house empty, she decided to take care of her laundry.

In her room, Judy pulled her new clothing from the bags. She used a pair of scissors to remove the tags, sorted the items, then took her new lingerie to the laundry room. Filling the sink, she placed her bras, panties, and other delicate items in the warm water.

While her lingerie soaked, she grabbed an armload of her other things, placing them in the washing machine. Before starting the washer, she removed her top and skirt, adding them to the load.

Back in her bedroom, Judy chuckled. She realized that for the first time since she was much younger, she walked through the house in her underwear. She shucked her bra and panties, put on a pair of pajamas, then took her undies to the laundry room.

After washing her lingerie, Judy hung them to dry. Unlike the underwear she usually wore, her new items wouldn’t go into the dryer.

For the next few hours, Judy washed and dried her clothes. She took her new things to her bedroom, putting the items in drawers and hanging them in the closet. After she removed the last load from the dryer, she checked her bras and panties. They felt damp, so Judy decided to take care of them later.

In her bedroom, Judy stretched out on her bed. She thought about her evening with Kim, the shopping, and the conversations they had. As Judy’s thoughts drifted to sex, she slipped her hand into the bottoms of her pajamas. Her fingers toyed with her pubic hair before moving lower.

Judy wasn’t new to self-satisfaction. She had been masturbating for years. At first, she would rub herself and touch her clitoris. As her experimentation progressed, she began inserting a finger into her vagina, carefully avoiding ripping her hymen.

One night while she played, Judy thought about her upcoming prom and what she wanted to do with her date. Deciding she wanted to be ready, she shoved the round handle of her hairbrush through her hymen. The initial pain was quickly replaced by pleasure. Once Judy felt comfortable with having an object in her vagina, she pumped the hairbrush in and out of her hole. Using her other hand to diddle her clit, Judy enjoyed the best orgasm to date.

Reaching for the drawer of her nightstand, Judy took out her flexible dildo, complete with simulated testicles. She bought the sex toy after the hairbrush handle was no longer thick enough and didn’t reach the depths she desired. After stripping, Judy stretched out on her back. She put the phallic device in her mouth, sucking and wetting it.

Splaying her legs, Judy placed the end of the seven-inch dildo at the opening of her vagina. She wiggled her hips as the object stretched her opening. A moment later, the entire shaft of the fake cock was in her pussy. Wrapping her fingers around the bulging balls on the base, she slowly pumped it in and out.

As she usually did, Judy thought about a man fucking her. The image was faceless, but it didn’t matter to her. With her eyes closed, Judy dreamed of losing her virginity to a real penis. As she stroked the device in and out, the face of her imaginary lover became less obscure. As the features sharpened, Judy gasped. In her mind’s eye, it was her brother Mark hovering above her, fucking his sister.

Judy stopped moving the dildo. She was conflicted by her thoughts of incest. As she recovered from the strange feelings, she began sliding the device in and out of her vagina. When her orgasm began, Judy suddenly relived he kiss her brother gave her, and the feeling of his hand on her breast. If anything, the taboo thoughts fueled her climax, and she came harder than she ever had in the past.