My Sister's Best Friend

A/N - Hello all. I think this is only the third story I've ever written for this category, and the first two stories were part of a series I finished long ago.

Much like my 'Love Around the World' series, most of these stories will probably only be around 10k to 15k words. Well, that'll be the aim though they might go for longer, as long as the stories don't drone on unnecessarily!

Previous stories in this series:

My Father's Best Friend (Gay Male)

My Mother's Best Friend (Mature)

Australian / British standard English. There is a good chance of: lots of profanity, characters drinking, typos, mistakes, and bad grammar at times.

Proofreading and editing suggestions provided by OhDave1. Any mistakes are still mine.

Comments are appreciated as always. Anonymous comments are moderated.

Feedback by email is always welcome. Enjoy chatting with anyone who likes my work.

*****

A sister does her best to help her little brother finally get laid.

*****

Hannah

Watching her little brother messing around with a couple of his friends by the pool, she glanced to her side to see her three best friends all watching on with interest. Hannah still referred to Chris as her 'little brother' though there wasn't all that much 'little' about him anymore. He'd turned twenty a couple of months before and had long towered over the women of the household. He'd done so since around the age of seventeen when he finally had that long-awaited growth spurt.

He was now six-two. Years of playing rugby league had helped give him a defined physique as although only an amateur, he took it seriously and was at the gym five days a week. Broad-shouldered, strong arms, a toned chest though not overly cut. His blue eyes were currently hidden by his sunglasses, he used an electric razor and always kept a day or two of stubble. Thick light brown hair on his head.

Hannah knew she was biased when it came to her little brother, thinking he was incredibly handsome. But it was his sweet nature that made her love him so much. He barely had a bad bone in his body. Even on the rugby field, he would put his body on the line but was never unnecessarily violent in what was already a violent game. She'd never seen or heard of him throwing a punch.

And his friends clearly loved him as well. His three friends with him by or in the pool had been by his side since their earliest days at primary school.

"Is your brother still single?" Melody asked her quietly.

Hannah had to nod as she wasn't aware of any special woman in his life. "The last girlfriend he had was Jennifer, when he was in high school. I don't think they ever did all that much together," she replied.

"You don't think... You think he might still be a virgin?" Melody asked, Hannah noting the surprise in her friend's tone.

"Well, I don't think he ever did anything with Jennifer. They started dating before his growth spurt, and though he's still rather shy now, he was even worse when he was around fifteen. Could barely say two words to a girl. Jennifer was the one to ask him out. She was a cute little thing. A little nerdish, if I'm honest. She genuinely liked him, but I think she liked him as her boyfriend as it kept every other boy at bay. She was bookish, but I saw her over here a couple of times in a two-piece, and she had considerable assets on her chest."

"But you don't think they ever did anything?" Melody asked.

"I don't ask my brother about his sex life, but I think Mum would have got him to say something about it once it happened. Or he would have let it slip." She paused and sipped at her drink. "I know he was heartbroken when Jennifer chose to attend university in Melbourne instead of staying in Sydney. But she wanted away from everything here. Shitty homelife, not many friends, and going to Melbourne offered a fresh start."

"And he's been single since?" Gina wondered, one of her other two friends showing an interest in their conversation.

"As far as I'm aware. He doesn't talk much about his private life, but I think that's because there isn't much of one. He studies five days a week. Goes to footy training two nights a week during the season. Plays his game on a Saturday afternoon. Sunday is his only real free time of the week."

Hannah laughed as Chris was wrestling with one of his friends and easily got the upper hand, eventually pushing his friend into the pool. His friend reappeared, thankfully laughing away. "Always forget how fucking strong you are," Mike exclaimed.

"Don't think I'm offering a hand to help you out. I know you'll just try and pull me in."

Mike lifted himself out and walked to get his towel, noticing that Chris kept a careful eye on his friend. Mike was his best friend, and the pair were always horsing around. Both were mature and responsible young men most of the time, but put them together, and they revert to idiot teenager status.

"Do his friends have girlfriends?" Melody wondered.

"Mike's been with his girlfriend since they were both sixteen. Seeing them together, you know it's for life. It's rather beautiful. Mark plays the field. New girl on his arm every three months or so. Daniel is recently single. His girlfriend was a year younger and wanted to enjoy the full university experience."

"Why do some young women always think that?" Hailey asked.

"It's the modern world," Gina replied, "I never had an interest in heading out each weekend to get fucked by random blokes. I mean, enjoy sex if you want, but I always found the sex was far better with someone who loved you, and took the time to learn your body, how to make the experience so totally enjoyable that you'd never want to let him go."

"So your brother has spent nearly three years at university single and not getting laid?" Melody finally asked.

"It's not a bad thing being a virgin, Melody," Hannah replied.

"I know. I know. But he's so damned sweet and handsome..."

"You're single, Mel," Hailey stated, "Why don't you date him? Or would that be an issue of concern for you, Hannah?"

Melody immediately glanced at Hannah. Hannah was aware that her three friends all had a crush on her little brother. They all might be twenty-four years old, but the age gap wasn't that much of a problem. Hannah was currently single, and if it wasn't for the fact Chris was her brother, she would consider dating such a sweet and handsome young man.

"I know you won't hurt him, Mel," Hannah finally replied, "But he is my little brother. I know you wouldn't break his heart, but I'm left thinking that he's now been a virgin for so long, aware all of his friends have likely lost theirs long ago, that I reckon he might only want to be with a woman who he'll want to spend his life with."

"You mean a one-and-done?" Melody replied, "You really think that?"

"If it wasn't for the fact Jennifer moved away, I think they would have been intimate eventually and would have remained committed."

"Maybe you could feel him out for me..." Melody finally suggested, "I mean... If you don't mind the idea of me dating him?"

Hannah removed her sunglasses and looked at her best friend, Melody removing her sunglasses so they could look at each other in the eyes. "You know I love you, Mel. And most important is that I trust you. I'll talk to Chris and figure out what he really wants. I know you wouldn't just spend a night in bed with him and that would be it."

"I wouldn't just leap into bed with him anyway," Melody assured her, "Do you think he'd want to date me?"

That made the other three girls laugh. "Please, he's always checking us out," Gina exclaimed, thankful that Chris and his friends were far too engaged in their own conversations to pay any attention to their conversation.

"My little brother is obviously very shy, and when it comes to his sister and her friends, I'm sure you don't miss how awkward he can still be from time to time," Hannah said, "And the idea of asking out one of his sisters' friends... I'm sure he probably thinks about it but would believe that I wouldn't like it."

"So maybe I should ask him out then?" Melody wondered.

"Let me talk to him first. If he seems keen, then I'll give you the green light, Melody."

"You do realise he's not the only one to have a little crush," Hailey said softly.

"I'm aware the three of you all like looking at him, but how well do you really know him at heart?"

"I'd like to get to know," Gina stated.

"Me too," Hailey added, "But given that we both have boyfriends, and that Melody is currently single..."

The two groups didn't particularly mingle for the rest of the afternoon. Chris's friends were friendly but not all that interested given their relationship status or they were a little wary that it was Hannah and her friends. Hannah and her friends only started to head inside when the sun started to disappear, and the heat of the day started to fade.

Chris was already inside, his friends having gone home for the evening. Melody, Gina and Hailey all disappeared to Hannah's bedroom to get changed, no plans for the evening as they'd been out together the night before. Hannah still lived at home with her mother and younger brother as finding somewhere to live that was reasonably priced had proven difficult. Melody still lived at home, and Gina and Hailey lived with their boyfriends.

Their mother arrived home after a day out with her friends, carrying some shopping and also a couple of large pizzas. Chris wandered out from his bedroom upon hearing his mother call out, greeting her with the usual kiss on the cheek and a big cuddle. Hannah always smiled at seeing how affectionate the young man was with his mother. And her mother always had this smile on her face that reflected just how much she loved that her grown son never shied away from showing his love and affection.

He'd been a little awkward during puberty. No real surprise considering the changes to his body and hormones raging. Hannah had noticed the distance he kept from her, for example. She was aware of the little crush he'd also nursed on his big sister. Never anything that would get out of hand and very weird, but she was only a few years older than he was, and once the awkwardness passed, their relationship was even better.

After dinner, Chris grabbed a drink from the fridge and returned to his room, Hannah noting it was only a bottle of soda. He never drank at home and rarely had much to drink when he was out and about with his friends. Hannah watched some trash television with her mother, sharing a bottle of wine as her mother shared a couple of stories from the brunch she'd had with her friends.

"Megan is on the verge of finally leaving her husband," she explained, "I told her she should have done it ten years ago. I've never been shy in telling you that the best thing I ever did was kick out your father when I did. Nothing but a mooch and a loser."

"You did have two kids with him, Mum," Hannah always liked to tease. At least her mother could joke about it nowadays.

"The only good thing about your father was that he was decent in bed. And he helped me get a wonderful daughter and son. At least my little boy isn't like his father."

"He's very sweet, isn't he?"

"He is." She watched her mother sip at her glass of wine before she sighed. "I just wonder about, you know... I know he's not gay. He's definitely not gay."

"How do you know?"

"I've seen what he likes to watch. I've never caught him, you know, jerking off. I've just seen his laptop a couple of times."

"What was he watching?"

"To my surprise, it was simply a film of a young woman pleasuring herself. I would have thought a young man wanted to watch people have sex. What made me laugh is that he's never hidden away his phone or closed a window on his laptop. If he's looking at something, he won't be embarrassed by it."

"Mum... What do you think of the idea that one of my friends dates him?"

She noticed the slight look of surprise on her mother's face before she asked, "Who of your friends wants to date him?"

"Melody. I know Chris has always had a little crush on her. And Melody has admitted that she's been aware of how he's grown and matured, particularly since he left high school."

"Melody is a lovely young woman. My son could do a hell of a lot worse. But she's your best friend, Hannah. Say they date for a while, even get quite serious, but then it goes wrong. Who would..."

"My brother," she replied without hesitation, "Unless he does something stupid like cheating on her, I'd always choose my brother. Melody would know that too."

"Does your brother have any idea?"

That made her laugh. "Mum, I don't think Chris has a clue when it comes to women and their interest in him. We've been to a few of his rugby league matches on a weekend. He's a big, broad young man, and you can see the eyes of so many pretty girls following him around the field. Even when covered in mud and sweat, he still looks good."

"Sounds like you have a little crush on him too, Hannah," her mother teased.

"I just know my little brother is a handsome young man."

She left the topic alone for a few days, waiting until Thursday night to speak to him. Their mother was always late home on Thursday as it was still the night of the week when the shops were open later, and their mother loved to go shopping. She'd occasionally spoil herself and would usually return home with something for her children, even though they were both now in their twenties.

Finding Chris in his bedroom, sitting at his desk and studying hard, she flopped down onto his bed. Resting her head in her hands, she watched him type away at his laptop for a couple of minutes.

"Something you want, Hannah?" he asked lightly, finally turning back to glance at his sister.

"Just wanted to spend some time with my little brother."

He pulled a face that made her chuckle. "Uh-huh. You want something from me or..."

"I have a question, Chris. A personal question and I'm going to ask it rather bluntly. I'm hoping you can be honest with me."

Turning his chair around, his blue eyes met her own. "Okay. Shoot. What's on your mind?"

"Are you a virgin?"

She thought the question would embarrass him and did feel a little guilty asking it so bluntly. But when the smile formed on his face, she was left wondering what the response would be. "I am, Hannah," he admitted, "I'm guessing you're asking for a reason."

"Why did you never have sex with Jennifer?"

"Honestly?" She nodded and he took a deep breath. "You never figured it out?"

"No. What?"

"She was a lesbian, Hannah. I was her beard during high school. She explained what that term meant."

"And you did that for her?"

"She was my best friend," he replied softly, an incredibly sweet smile forming, "We loved each other, but it was the love of friendship, not romantic or intimate."

"Is it why she left Sydney?"

"Absolutely. Me posing as her boyfriend kept her safe from her lunatic parents and family. They're all nutjob happy clappers. The idea that their daughter was a rainbow warrior... They tolerated me in the sense that I kept my hands to myself, and it was obvious their daughter remained virginal."

"Did she date while you posed as her boyfriend?"

"No. She didn't want to insult me that way. She said that she'd simply finish her studies in Sydney, and once she was in Melbourne, she would live as free as she wanted. We've obviously kept in touch over the years. She's enjoyed herself immensely."

"But what about you, Chris?" That's when his cheeks did grow a little brighter, Hannah moved to sit on the edge of the bed, patting the spot next to her. He was up and next to her rather quickly, taking his hand in hers. "Chris, you can tell me anything. You know that."

"It's just... Before my growth spurt and everything, I didn't exactly have a lot of self-confidence. And I still feel so awkward trying to talk to girls, at least when it comes to a romantic setting. When a girl is just a friend, there's no pressure and it feels normal. But if it's a girl I like, I just... I just get all tongue-tied and feel stupid, and then... I mean, girls are not shy in coming forward, but I have no idea if they're flirting to just feel good about themselves, or if their interest is genuine, or...." He trailed off and sighed. "I know I'm twenty and supposed to be full of self-confidence bordering on arrogance, but I've never been good at any of that stuff. At least when I was with Jennifer, there was none of that pressure. We just faked it to make it."

"You ever kiss her?" she asked softly.

"I know how to kiss. She was a lesbian, and admitted it to me years ago, but she did like kissing me. She liked the fact I was gentle and, well, once we figured it out, we would enjoy the occasional make-out session. Jennifer needed to feel love as much as I did. But she never let it go further than kissing."

"Not even a bit of under-the-shirt action? Not feel her up?"

"Nope. I didn't want to take advantage of her like that. She laid down the rules and I respected them. We could kiss as much as we wanted but nothing else was on offer. Her virginity was only going to a woman, not a man."

"But she left not long after you graduated from high school. Have you not been with anyone since?"

He sighed. "No," he finally said quietly, "I'm just... I don't know..." He trailed off and sighed again.

Cuddling into his side, she smiled when he immediately turned to cuddle her, closing her eyes and enjoying how close they still were. "Chris... Do you still have a little crush on Melody?" The groan that escaped him made her giggle. "I'll take that as a yes."

"I doubt she'd ever show an interest in me," he muttered.

She leaned back enough to kiss his cheek before leaning further back to meet his eyes. "Would you ever consider dating her?"

"But... She's your best friend... I thought there were rules about things. Like I wouldn't exactly be thrilled if one of my friends... I can't stop it, but I don't exactly have to like it."

"They are stupid rules, Chris, and they only exist in the minds of some people and from stories you might read elsewhere. The fact is you're free to date whoever you want, as much as I am. Yet while I think your friends are nice, I'm not interested in them. Now as for Melody, you know she's twenty-four, so she's a little older. She had a boyfriend through university though they split up as he left for Western Australia for a job. She's dated a bit since then but hasn't had any luck finding the right guy for her."

"And you think it could be me?"

"You already know each other a little bit."

He remained silent, Hannah happy to just cuddle against her little brother. She would admit to feeling a little lonely after breaking up with her previous boyfriend, and her little brother was always available to cuddle, making his big sister feel better.

"Would she really be interested in me?" he finally asked.

"Why don't you talk to her next time she's here and find out?"

"God... I'll just get all tongue-tied and awkward around her..."

She leaned back and met his eyes. "Melody thinks you're an absolute sweetheart, Chris. You are a wonderful young man. I think so. Mum waxes lyrical about you to everyone. Her friends. Her colleagues at work." She noticed his cheeks glow slightly at her compliments. "Don't ask her out straight away. Just come over and talk to us next time my friends are here. It'll help your confidence at the same time."

"Okay... If you're sure..."

"Part of me thinks it's lovely that you're waiting, Chris. So many people are in a rush to have sex and too many probably regret losing something that is special to someone that means little to them. And if you make love to someone special, and you remain with that person, then that's your decision too. You don't have to go out and have sex with anything with a heartbeat and a pussy. There are a lot of men and women out there who consider sex to be something special, to be shared only with someone you love."