A Boyfriend for Cindy
Copyright 2020 by Caliboy1991. All rights reserved. Used by permission.

Part 2

Cole fidgeted, sitting on the couch as he waited for Cindy to finish getting ready in the bathroom. He glanced at the clock on the VCR and even though it was only a few minutes after five, he worried about how crowded Red Lobster would be if they didn’t leave soon.

As though on cue, the bathroom door opened and then Cindy slowly walked into the room. She wore the purple dress from the previous week. Golden ringlets fell from her hair, not quite touching her shoulders. Normally, the teenager didn’t wear makeup, but this evening her lips glistened and her cheeks practically sparkled from rouge. Her blue eyes seemed to pop behind some dark eyeliner.

“Do I look okay?” she said.

Cole’s eyes were drawn to the dressy black sandals on her feet. Part of him felt a bit of relief. While Cindy wasn’t tall, even at five feet two inches, she was four inches taller than him. Had she worn high heels, she might have topped him by a head. Cole lifted his eyes, taking in her long, slender legs that disappeared under a purple hem several inches above her knee. Above her breasts delicate straps looped over her shoulders.

Cole wasn’t sure, but Cindy’s boobs didn’t look as big as they had when she’d gone to the dance the previous Saturday. The dress was modest enough to cover them while still exposing a bit of cleavage. One of his friends from school had told him that he’d caught his sister stuffing tissue down her bra, trying to make her tits look bigger. For a fleeting moment, Cole wondered if Cindy had tried that on her last date. Without the extra padding her boobs didn’t stick out very far. Cole didn’t care about that. He didn’t know how it was possible, but Cole thought Cindy was the prettiest that she’d ever been.

“Wow, you look pretty,” was all he managed to say as he continued to stare.

“Thanks,” Cindy said as she came over to him and leaned in to straighten his collar. “You do, too.”

As they left, Cole hurried over to the driver’s side door of the old Honda and opened it, “Ma’am, after you.”

As Cindy slid into the bucket seat, for the briefest of moments, Cole thought he’d caught a glimpse of black panties. The butterflies returned as he closed the door. By the time he climbed into the passenger seat, his penis had taken on a life of its own and he was glad the black dress pants bunched up as he sat down.
The nearest Red Lobster was between State Highway 8 and the 610 Loop, just inside Houston’s city limits. That suited Cole just fine. As much as he had looked forward to this evening with Cindy all week, he didn’t really want to run into any one from school. In fact, the further Cindy had to drive to get to the restaurant the happier he’d be.

As Cindy got onto highway 59, which would take them into Houston, she said, “Did you see how much Dave gave us this week?”

“Yeah, a hundred dollars. I know he really like Mom. But I still don’t like him much.”

“Me neither, but I could hate him a lot more and be okay with things if he keeps buying us off each week,” Cindy said.

Cole glanced at his sister, who gripped the steering wheel with both hands as they entered the heavy traffic for which Houston was known. She glanced back at him, “I hope you don’t mind, but I grabbed some of his blood money for dinner this evening.”

“No,” Cole blurted. “I do mind, Sis. Tonight’s about showing you that not all guys are assholes. I know I’m too young to drive, but I’ve got everything else taken care of, okay?”

Releasing her right hand from the wheel, she patted Cole’s leg, “Wow, Cubby. I didn’t realize how much it must sound like I hate men, but if that’s what you want, then, yeah. Okay.”

Cole offered a smile, “Thanks.”

Cole hadn’t needed to worry. There was no wait to get seated at Red Lobster. Friday Night Lights in Texas kept a lot of people out of restaurants until after the end of the game. As they looked over the menu, Cole’s eyes grew round as he looked at the prices on the menu. He’d never taken anyone out to eat before. Apart from getting food from Dominos and McDonalds, he’d hardly ever paid for his own meals before. This was a new experience.
Without thinking about it, his hand drifted to his back pocket where he’d put his seldom-used wallet. He’d put fifty dollars in it before they’d left the house and as he returned to studying the menu, he was glad he had. He’d never realized lobster was so expensive.

After they placed their order, as Cindy stirred a packet of sweet n low into her tea, she said, “Thanks for doing this, Cole. Since Mom started dating Dave, we haven’t really done much as a family. I can’t remember the last time we went out to eat like this.”

Cole had opted for Dr Pepper and after taking a sip, he said, “What do you think is going to happen between Mom and Dave?”

Shrugging, Cindy said, “I don’t know. He hasn’t popped the question in two years of dating, but they spend most of the week together at his place in the Woodlands.”

“Yeah,” Cole said with a bit of acid in his tone, “and we’ve never been over there to see them.”

Cindy played with the spoon in her tea for a moment, “I went over there once. Last year.”

His Dr Pepper forgotten, Cole said, “You never told me before. Why’d you go over there?”

Despite the rouge on her cheeks, the girl’s face grew scarlet, “Well, it was something of a girl thing. I called Mom from school and she picked me up and took me over to Dave’s place where she helped me with my problem.”

Cole’s confusion was writ large on his face. Cindy leaned forward, lowering her voice, “You know about girl problems we have each month, right?”
When the boy’s look of confusion didn’t go away Cindy whispered, “My period, goofus.”

“Oh,” Cole managed.

“Yeah, the first time it happened was at school. Mom took me over to Dave’s because that’s where she had her ‘woman stuff.’”

“What was it like?”

“Kinda gross. Blood coming out of your you-know-where.”

Cole blinked in surprise, “Gross. No, I meant Dave’s house. What’s it like?”

Cindy offered an embarrassed smile, “Oh, nice. It’s big enough that if he wanted to let us come live there with him and Mom there’d be plenty of room. But he doesn’t like kids. When he found out Mom had taken me over there, he got upset and made her promise not to do that again.”

“What an asshole,” Cole whispered in return.

After dinner, the two siblings talked about school until the waiter came over, “Will there be anything else?”

As the waiter left to prepare the check, Cole said, “Why’d he sound so pissed?”

Shrugging, Cindy said, “Probably thinks we’re not going to leave a tip.”

“A tip?” Cole’s voice came out as a squeak. “What’s that?”

Cindy replied, “One of my friends works at a restaurant. She gets paid next to nothing for working there, but she keeps all of the tips she gets paid. Most people leave ten to fifteen percent of the bill as a tip.”

Chagrined, Cole said, “So, I’ve got to pay the waiter, too?”

Cindy reached across the table and took hold of Cole’s hand, “I know you want to take care of this, Cubby, but if you want, I can get Dave’s money out of the car.”

Cole shook his head, “No. This is my treat, Cindy.”

After paying the bill and tip, Cole balefully stared at the lonely face of Abraham Lincoln that stared back from his wallet before forcing the biggest smile he could manage onto his face. “Did you have a good time?”

Cindy grabbed his hand again and squeezed it, “More than all my other dates combined. This was fun.”

Cole came around behind his sister’s chair and helped her up, “I’m glad. But it’s not over yet. When we get back home, I rented a movie I think you’ll enjoy. I hope that’s okay.”

As Cole opened the door to the car for his sister, she playfully slapped his arm, “I hope it’s not Red Dawn. I’ll take me some Patrick Swayze in Dirty Dancing all day long, but you can have him all to yourself in Red Dawn.”

After he settled into the passenger seat, Cole tried to put a mysterious look on his face, “You’ll just have to wait and see.”
The drive home was as fun as dinner as Cole shared a few jokes he’d heard at school that week and the two made jokes about Dave. Once they arrived home, Cole raced around to the driver’s door and opened it.

As Cindy got out, she said in an exaggerated Texas drawl, “Why I do declare, Master Colton, you are absolutely the perfect gentleman. You have redeemed the male of the species this evening.”

As Cole made his way around his mom’s car to open the door to the kitchen, Cindy said, “Just a sec, okay?”

She joined him on the welcome mat and took his hand, “I’ve always wanted my dates to end on the door step. If the date hadn’t gone well, then I wanted to tell the boy good night and send him on his way. But if the date had gone well or if I really liked him, then I could give him a kiss before sending him on his way.”
Cole felt his hand grow clammy in his sister’s hand. He didn’t know what to say, so he just stood there inside the poorly lit garage, looking up into the dark orbs of his sister’s eyes.

She took his other hand and inched forward, leaning down a bit until her lips brushed Cole’s. His first kiss made the butterflies return and he felt a tickling sensation below his belly.

Cindy pulled her face away, and peered at the stunned expression on Cole’s face. “I’m sorry, I shouldn’t have done that.”

Cole found his voice as a smile creased his face, “No, yeah. I mean, I’m glad you did. Makes me think I did good this evening.”

A smile returned to his sister’s face as she leaned in a second time. This time Cole had some inkling of what to expect and he returned the kiss. It was over almost as soon as it began as Cindy broke the kiss and turned and entered the kitchen and asked, “What movie did you pick up?”

Cole tried to ignore his emotions and the butterflies as he hurried back to his room where he had left the Blockbuster rental box and hurried back into the living room where Cindy had settled into a seat on the couch. He handed over the VHS cassette.

Cindy nearly screamed, “You got the Breakfast Club! If you weren’t my favorite person in the whole world before, you are now.”

After putting the movie in to play, Cole turned back to the couch. Cindy patted the cushion next to her, “Come on, I know it’s not Red Dawn or Top Gun, but try to enjoy it with me.”

Settled in next to his sister, Cole glanced down where their knees met. The purple dress crept up a bit exposing most of Cindy’s thighs. He couldn’t ignore the fluttering in his stomach even as he tried to focus on the movie.

The Breakfast Club started their detention, Cindy drew her feet onto the couch and leaned her head onto Cole’s shoulder. Cole had to move his arm as it was in the way. He wasn’t sure what to do with it because the only place to rest it seemed to be on his sister’s shoulder. As he settled it there, he heard an audible sigh.
The rest of the movie passed in a blur as Cole tried to figure out how he felt about his sister leaning against him. As the credits rolled, he decided he’d liked it, even if the fluttering in his stomach never quite went away.

Cindy stretched her legs out and her head slid down from Cole’s shoulder, until it rested on his lap. He looked down at her face. He couldn’t remember the last time she looked happier.

Without a shoulder to wrap his arm around, Cole let his fingers twine through his sister’s hair. He’d never been this close with anyone before and he really didn’t know what to say or do. But he knew he’d wanted his sister to have a good date and not judge other guys by a couple of bad experiences. He went back to that, “Did I redeem men, Sis?”

Cindy’s eyes were half closed as his fingers touched her scalp, “Mmm, that feels good, Cubby. I don’t know about all guys. But this was the best date I’ve ever been on. You were awesome. If you treat your first girlfriend like you did me, you’re going to get yourself laid in no time flat.”

Flushing at the praise, Cole was old enough to know about getting laid. Several boys in gym class had bragged about getting laid. He was pretty sure they were full of shit, but hearing his sister’s praise made him feel like his was ten feet tall, instead of less than half that.

With his other hand, Cole ran a finger along his sister’s jawline, “You’re the prettiest girl I know, Sis. You’re funny and smart, too. You deserve to be treated like a princess. I know I would.”

Cole’s heart seemed to skip a beat as Cindy opened her eyes and gazed into his face. She smiled and raised a hand and brought it to his face, where she ran it from his ear down to his neck, “Are you asking me out on a second date, Cubby?”

The heat of her finger on his neck thrilled the boy as he returned her smile, “I, uh, I guess I am.”

Cindy sat back up and leaned over and kissed Cole’s cheek. “You are the sweetest boy in the whole world.”

She stood, “It’s late. How many yards do you have tomorrow?”

Feeling the fluttering subside a bit, Cole rose and ejected the movie from the player, “Five, if Mrs. Johnson doesn’t change her mind.”
He followed the girl in the pretty purple dress down the hall where she turned around. Cole had been close behind her and when she stopped and turned, they did an accidental chest bump. The boy nearly lost his balance as he tried to step back, but his sister’s arms had wrapped around his neck, keeping him from falling or backing away. In fact, their faces were so close to each other the boy could see deep into her aqua colored eyes.

She leaned in and for the third time that night he felt her warm, soft lips press against his. Unbidden, his own arms wrapped around her back as he pressed his lips against hers. The fluttering in his stomach went into overdrive as he felt a tingling come to rest in the center of his body.

This time, when Cindy broke the kiss she said, “Yes, Cubby. There’s nobody I’d rather go on a second date with than you.”

With a kiss and a promise, the teenager turned and a moment later, her bedroom door closed behind her, leaving Cole standing in the hall with a silly grin on his face and an erection in his pants.


Cindy took a final look in the bathroom mirror. Not too much blush, just right, she thought as she closed the make-up case. She’d thought about wearing a different dress than the purple one from the previous week, but when she thought about the look on Cole’s face when he’s seen her wearing it, Cindy decided that it was the right dress, after all.

She looked at her boobs. They were back to their normal size, augmented only by the dress’s padding, after all, she didn’t need to try to impress her date this evening with a fake bust size.

She primped her hair with a comb and decided she was ready. When she walked into the living room, she noticed how Cole’s attention fell completely on her as he ignored the TV. As his eyes traveled from her sandals to her dress and then to her face, Cindy felt more vulnerable than she had all week. Before now, her brother wasn’t the kind of boy to gawk at her.

Cindy felt uncertain, painfully aware of the boy’s gaze, “Do I look okay?”

Her uncertainty grew until Cole said, “Wow, you look pretty.”

Noticing Cole’s collar was crooked, Cindy came over to him and straightened it. “Thanks, you do, too.”

In the garage as Cindy headed toward the driver’s side door, Cole rushed by and opened it for her, “Ma’am, after you.”

Once the boy climbed into the passenger seat, Cindy headed out. The way he’d opened the door had impressed her. Jason hadn’t bothered when she’d taken him to the Olive Garden. Maybe there was hope for her brother, yet.

She enjoyed the drive. The longer she drove the more at ease her brother became. Which was a good thing. The nearest Red Lobster was more than thirty minutes from their house. She’d been especially impressed when her brother told her that he was paying for the meal.

By the time they sat down to eat, Cindy was enjoying herself more than she had on either of her earlier dates. But when the girl looked over the menu she was a little surprised at the prices and wondered if Cole might have set himself up for failure. The lobster dinner was positively expensive. But Cole just smiled, “Get what you want, Sis. I’ve got this.”

After their drinks arrived, Cole put his elbows on the table and leaned forward, “What do you think is going to happen between Mom and Dave?”
Cindy had been thinking about the same thing for a while. Sure, Dave made her mom happy like nothing else ever had, but that still didn’t mean the girl like her mom’s boyfriend.

With a casual shrug Cindy said, “I don’t know. He hasn’t popped the question in two years of dating, but they spend most of the week together at his place in the Woodlands.”

There was acid in Cole’s voice, “And we’ve never even been over there to see them.”

Cindy felt the color rise in her cheeks. That wasn’t entirely true, but she wasn’t sure she wanted to explain, not even to Cole. As she played with the spoon in her tea, she saw the storm on Cole’s face and decided it probably wouldn’t hurt to tell him. “I went over there once. Last year.”

Cole’s eyes snapped up from his drink, “You never told me before. Why?”

Cindy felt the heat rise on her face. She’d had her first period during the middle of Sophomore English. She’d called her mom, when she’d been staying over at Dave’s house. Once Cindy explained the reason for the call, in a fit of maternal instinct, her mom picked her up and took her over to Dave’s place to get cleaned up while he was at work.

“it’s something of a girl thing, Cole,” Cindy leaned forward and whispered. “I called Mom from school and she picked me up and took me over to Dave’s where she helped me with a problem.”

Cindy didn’t know if she should laugh or cry at her brother’s confusion. Lowering her voice further, she added, “You know about girl problems, right? The one we have every month.”

Cindy’s heart melted as the innocent confusion on Cole’s face. “My period, goofus.”

“Oh,” Cole managed, followed by a louder, “OH!”

“Yeah, the first time it happened was at school. Mom took me over to Dave’s because that’s where she had her ‘woman stuff.’”

“What was it like?”

“Kinda gross. Blood coming out of your you-know-where.”

Cole blinked in surprise, “Gross. No, I meant Dave’s house. What’s it like?”

Repressing a giggle as her brother’s reaction, she said, “It was nice. It’s big enough for all of us. That bastard just doesn’t want to let us come live there. Mom says Dave just doesn’t understand kids, but I think he’s just a rat bastard who hates us.”

“What an asshole,” Cole shuddered.

The rest of the meal passed by with better conversation and by the time they’d left for home Cindy was happy she’d let Cole talk her into the little date.
Cole only reinforced it more when he opened the car door for her in the parking lot.

“What’d you get for us to watch?” she asked as Cole went around to the other side.

Cole offered a mysterious expression that looked sillier than it did secretive. “Wait and see, my darling,”

If it were possible for the drive home to be more fun than the rest of date, it was. Cole kept her guessing about the movie the entire time. Cindy loved every minute of it and hated to see it end when she pulled her old Honda into its spot in the garage.

She’d barely put the car into park when Cole hustled around and opened her door yet again. The single 60 watt bulb handing from the ceiling let her see the happy sparkle in her brother’s eyes as she climbed out to the car.

She patted his arm playfully and said, ““Why I do declare, Master Colton, you are absolutely the perfect gentleman. You have redeemed the male of the species this evening.”

But she felt a flapping of butterfly wings in her stomach as she said the words. She’d felt those feelings before. First when she’s gone on that one date with Darrell and then when she’d asked Jason to the dance.

How could she possibly feel the same way about her little brother? That was easy. Cole had treated her a hundred times better than either of those jackasses. And the way he’d looked at her through dinner, as though whatever she talked about what the most important thing in the world. Maybe she felt this way because he’d treated her the way she’d always thought a boy should treat a girl on a date.

As her brother reached the door to the kitchen, Cindy decided he deserved something special for being the best date she could have ever wished. “Just a sec, okay?”

When she reached her brother, Cindy grabbed one of his hand, holding it gently, “You know, I’ve always wanted my dates to end on the door step. That way, if the date had been a disaster, then I could tell the boy good-bye and send him on his way. But if the date had well or if I really liked the boy then I could give him a kiss before sending him on his way.”

Cole’s hand felt sweaty in hers as he gazed back at hers with eyes that made Cindy’s heart beat faster.

Before Cindy could lose her nerve, she took her brother’s other hand and leaned down until her lips brushed Cole’s. The shocked expression on her brother’s face sent icicles of terror into her heart and she pulled away, “I’m sorry, Cole. I shouldn’t have done that.”

Her brother squeezed her hand as a smile played across his face, “No, yeah. I mean, wow, I’m glad you did. Makes me think I did okay this evening.”

The icicles melted and Cindy returned the smile. She leaned again and was pleased when his lips returned the kiss. It was over too quick. Cindy didn’t really know what to make of her feelings so she led her brother into the kitchen.

“What move did you pick up?”

Cole picked up a VHS cassette tape and handed it to Cindy as she settled into a spot on the couch.

As she read the title, she decided her brother really had earned those kisses, “You got the Breakfast Club! If you weren’t my favorite person in the world before, you sure are now.”

Once her brother started the movie, Cindy patted the seat beside her, “Come on. I know it’s not Red Dawn or Top Gun, but try to enjoy it with me.”
As the movie started, Cindy looked out of the corner of her eye and saw Cole staring at the place where their knees met. Her dress had slid up a bit when she sat down, exposing most of her thigh. She wondered what was going through his head.

As the detention scene played, the girl kicked her sandals off and tucked her feet under her. She hadn’t thought about the consequences of doing it until her body leaned against Cole’s. The boy didn’t pull away so Cindy laid her head on his shoulder.

She’s accidentally trapped his right arm and he rolled his shoulder enough to move it without disturbing Cindy’s head. He snaked it around until it rested on her right shoulder.

Cindy tried to focus on the movie but the way her stomach fluttered and her heart beat, it was a useless task. She couldn’t ignore that how she felt about Cole was changing. It was really weird to realize she felt closer and better about him than she’d ever felt about Jason. And that left her feeling all muddled. As little as a week ago, Cindy had hoped that after the dance that she and Jason could go somewhere and make out, maybe even go all the way. She didn’t need to worry about getting pregnant. Another good thing her mom had done was to put her on the pill after she’d started getting terrible cramps each cycle. They were a miracle drug as far as Cindy was concerned. Her cycles had stopped altogether and she’d not had a cramp since then.

And now the same butterflies she’d felt for Jason she was now feeling for Cole. Obviously, she wouldn’t have sex with her brother. Gross. You just didn’t do things like that. Plus, she was pretty sure Cole’s body was too immature for that part of his plumbing to work. He was the least developed boy in his class, after all.

She couldn’t help glancing down at her brother’s crotch. The black dress pants were bunched up in his lap and she couldn’t really see the outline of anything. She decided that was probably because his penis was immature and small.

Having settled that thought didn’t make her butterflies go away, though. She wondered if she really was falling in love with her little brother. Now though, the idea didn’t gross her out. After all, he was the only guy she knew who’d treated her right. She doubted that she could do much about her emotions, but for now, she decided to just enjoy the rest of the movie with her favorite person.

As the credits rolled, Cindy stretched her legs out on the couch and laid her head on Cole’s lap and looked up at him. The look on his face put a wide smile on the teenager’s face.

Cole’s smile warmed Cindy’s heart and then her heart fluttered when she felt his fingers running through her hair. She was enjoying the butterflies as she purred, “Mmmm, that feels good, Cubby. I don’t know what I think about all guys, but this was the best date I’ve ever been on. You were awesome. You treat your first girlfriend like you did me and your going to get yourself laid in no time flat.”

Cole flushed at Cindy’s words. He didn’t speak but rather touched her jawline on her cheek and traced it back and forth on her face. God, how the butterflies flapped in her stomach. Finally, her brother found his words, “You’re the prettiest girl I know, Sis. You’re funny and smart, too. You deserve to be treated like a princess. I’d treat you like that.”

Cindy had closed her eyes to better enjoy the heat of his finger on her face. His words made her eyes pop open. Cole’s face was still red with embarrassment but there was something in her heart that knew her brother spoke nothing but the truth.

Smiling at his words, she snaked her hand up his chest until she reached his ear and slowly traced his face and neck. “Are you asking me out on another date, Cubby?”

Cole’s grin grew even wider as Cindy’s finger lingered on his neck, “I, uh, I guess I am.”

Even though Cindy didn’t know how to sort her emotions or know where to draw the line with Cole, one thing was for certain, she’d go on as many dates with her brother as she could. She sat back up and leaned over and gave her brother kiss on the cheek. “You are the sweetest boy in the whole world.”

The evening was late and it was time for bed. Cindy felt her brother following behind her and she wondered if he was checking out her ass. The purple dress only came down a few inches below her panty line in the back. Even though she was tired, Cindy wanted to feel Cole’s body next to hers one more time and she turned around when she came to the bathroom door.

Cole bumped into her, their chests coming into contact. This must have surprised the boy because he nearly fell as he took a step back. But Cindy was fast, she’d already grabbed him around the neck and instead of falling away, his chest reconnected with hers.

Without thinking about it, Cindy pressed her lips against Cole’s for the third time that night. Any thought about boundaries or even her brother’s age blurred against the powerful seduction of the kiss.

When she broke the kiss she said, “Yes, Cubby. There’s nobody I’d rather go on a second date with than you.”