My Brother's Best Friend

A/N - Hello all. I've written a few stories in this category. I think it's fair to say that I do like to write about women who have a more dominant personality and carry that over into the bedroom.

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)

My Sister's Best Friend (First Time)

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.

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

*****

An older brother falls for his little brother's beautiful friend.

*****

I was eighteen years old the day my little brother sat me down one afternoon when he arrived home from school. Two of his close friends were with him, the two friends he spent nearly all his time with. I was in my final year of high school at the same time, finishing earlier each day than my little brother. At fourteen years of age, he was in the midst of puberty, his body changing with every day that passed. I'd given him as much advice as I could having gone through the same things only recently.

"James, can we talk in the living room?" he asked from his position in the doorway to my bedroom.

"What's up, Sam?"

"Um... Just need to tell you something. That's all."

Standing up, puberty had been relatively kind to me. I'd hit that magical six-foot that so many young men seem to covet. Got an extra inch out of it as well, tall enough that I towered over our mother, and even my father only hit five-ten. It was amusing the day he realised that he had to slightly raise his eyes to meet mine. I'd kept fit and slowly broadened out, years of playing sports certainly has helped my development.

My little brother hadn't quite had a growth spurt just yet, and I was left wondering if he might end up a few inches shorter than me. I don't think he would end up as tall as his older brother, but I had a good feeling that he would end up being a rather handsome young man.

Following him out to the living room, his two friends were sitting on the couch. Grabbing a drink from the kitchen before rejoining them, I sat in one of the two armchairs as the three young men sat together on the couch. I took a sip of my drink first before I leaned forward slightly.

"Okay, Sam. What's up?"

"Um... So... I've been thinking about things. And I'm also feeling, you know, things as well. Um..."

"Take your time, Sam."

"I'm gay," he blurted out.

"We all are," Steven added, sitting to his left.

"Yeah. We've kind of realised that we like boys, and each other, over the past couple of years," Tom explained, sitting to Sam's right.

Sam looked incredibly nervous as he could barely meet my eyes. I stood up and walked over towards him, taking a knee in front of him. To his surprise, I leaned forward and pulled him towards me, giving my little brother a hug. I wasn't surprised by the fact he needed to cry as I had a feeling that he'd been carrying it around far longer than any of us would know.

"I'm proud that you came to tell me first, Sam," I said softly as I leaned back to meet his eyes, thankful to see him now smiling, "Thank you for showing me that level of trust."

"You're my big brother. I thought... I thought you might understand."

"You're still maturing and changing. But when you know, you know. Are you dating anyone yet?"

"Um, not really. It's just that Steven and Tom have realised their feelings as well. Tom is a lone child and is worried about telling his parents. Steven will tell his mother later this week."

"Does anyone else at school know?"

"Only a couple of teachers I trust."

"But no one else?"

"No. Schools are still pretty shit when it comes to protecting gay kids. I'd rather just keep it secret until I get to university."

"Do whatever you think is best, but I agree that you'll probably find more freedom to be who you are once you're at university. They're usually a little more liberal and open-minded places."

His friends left soon afterwards while I returned to my bedroom to finish off my studies. I knew my little brother was more than smart enough to do anything he wanted to do at university. While I was smart enough to perhaps make it into your more ordinary studies, I had already decided that my future lay elsewhere.

Mum was the first to realise something was on his mind over the next couple of weeks. Our parents were divorced, but we still maintained a decent relationship with our father. I now just drove over to see him once or twice a week. Sam still went to see him every second weekend as per the custody arrangement, and Dad would pop around once a week to take him out for dinner, an event I would occasionally join in with. Despite the fact they were divorced, our parents managed to retain a decent relationship. The divorce was simply due to realising they were not in love with each other any longer.

Sitting down for dinner with our mother one evening around a fortnight later, we were discussing my options for after I graduated university when Mum glanced at my little brother to her other side. "Samuel, is there anything you need to tell me at the moment?"

When she used his full name, that was our mother being serious. My little brother started to blush a little bit, glancing at me nervously. Returning a smile, I nodded and hoped he understood what I meant by such a simple gesture. I watched him take a deep breath as he held out a hand to our mother.

"What is it, baby?" she asked softly. Mum had called him that nearly his entire life. She doted on my little brother. After giving birth to him, she had been told that she couldn't have more children. I was aware from conversations growing up that she would have loved a daughter to give us a little sister.

"Mum... I'm gay..."

"Oh baby, I know that already."

Sam's eyes widened slightly as he glanced between both of us again. "You do?"

"I know you're only fourteen, but you have shown absolutely no interest in girls." She paused and smiled. "And you don't delete your search history when using the family laptop."

"Oh..."

"I don't mind you being curious. Just don't let it corrupt your mind." Then Mum glanced my way. "And although I know you've had girlfriends, your curiosity was also obvious regarding certain women with a difference."

"Yeah. I figured you would find it though I knew you wouldn't freak out about it."

Mum looked back at Sam. "Anyway, Samuel. I'm glad you told me the truth. Did you tell your brother first?"

"Yeah..."

Mum smiled at me, taking my hand in her free one. "Thank you for being such a good big brother, James."

"There are a couple of gay guys and gay girls in my year. A lot of kids are still pretty narrow-minded about certain things, but most of our year was pretty good about it when they came out. And guys typically thought the lesbians would start making out in front of them."

Life carried on as usual after that, and it's safe to say that my little brother slowly but surely came out of his shell, a little more confident in himself, and I didn't miss the fact that he was spending far more time in the company of Tom. It was only after I'd graduated, and he'd finished the school year that I asked if they were now dating. He blushed though nodded his head.

The next couple of years passed by rather quickly in the grand scheme of things. I dated around a little bit though wasn't after anything particularly serious due to what I would be doing. I talked with Mum and agreed not to enlist in the Australian Army until my brother had graduated high school. She wanted me around to help him. Not regarding his studies, as my little brother was far smarter than me, but she wanted me around to help guide him through some of the pitfalls of being a hormonal teenager.

Sam turned eighteen during his last year at high school. I was twenty-two on the day of his birthday. I was still living at home, working full-time, helping Mum pay the bills, and she was happy for me to remain at home until I joined the army. Sam did come to me every so often regarding a personal matter. I had no idea what it must be like for him, growing up as a young gay man. I knew school was always easy from that perspective as he told me by the time that he was sixteen, most of his fellow students had figured it out and most simply didn't give a shit about it.

Spending one last Christmas and holiday period with the family before I was due to join up, my brother invited Tom over the day after Christmas and it was obvious that they were already quite serious about each other. Thankfully, Mum didn't bother me too much about my personal life though I knew the pressure was now on my shoulders to give her grandchildren.

As he and all his friends were now eighteen, they all wanted to head out to the city for the New Year celebrations. My friends were planning a big get-together for me at the end of January, so I had no plans, left rather surprised when my brother asked if I wanted to join him and his friends. With nothing else to do, I think I pleased him when I accepted the invitation.

"Um, is it okay if we go to a gay club or two?" he asked the night before we were due to go out.

"I've been to one before, Sam," I replied to his surprise, "A couple of guys I know at school were gay, and we had a gathering a year or so back that led to us going to a club."

"What was it like?"

"I think you're going to have the time of your life. Just be careful."

"Um... James... I'm still a virgin."

"Even more reason to be careful," I said, "But you've got a good head on your shoulders. I know you'll be safe enough."

None of my close friends were interested in joining us so I was the oldest of the group when we found ourselves travelling into the city. The younger men all had ideas of which clubs they wanted to hit up though we would visit a couple of pubs first. To my surprise, there were a couple of women along for the fun. They were not gay, they just wanted to have a night of peace without being hit on by a million and one guys. I assured them that I'd look after them without hitting on them at the same time.

After visiting three pubs and enjoying a few drinks, the young men were all eager to get into one of the clubs nearby. Within a few minutes of walking inside, it was obvious all the young men were in their element. Sam was shorter and slimmer than me, but even I could admit that he was a very cute young man. And his friends were definitely going to draw some attention.

While my little brother and friends wandered off to enjoy themselves on the dance floor, I perched myself at the bar, nursing a drink as I chatted away with anyone who ended up sitting on either side of me. I did keep an eye on the girls who had come with us though after a couple of hours, it seemed many of the men around them were keeping them just as safe.

"How's your night going, handsome?" a feminine voice asked, turning my head to see a gorgeous brunette take a seat on the stool to my right.

"Can't complain," I replied.

"Not interested in joining all the other men on the dancefloor?"

"Ah, well, unlike my little brother and all his friends, I'm not gay."

My answer made her grin and then chuckle. "I thought that but it's sometimes better to ask. So, are you only out with your little brother and his friends?"

"Yeah. It's his first proper night out to a gay club. But he came out to me and then the family years ago." Turning more to face her, the first thing I took notice of was a pair of rather pretty blue eyes. "What brings you here tonight?"

"I'll be blunt. I'm here to get laid."

I'm sure she expected some sort of exclamation. I smiled and asked, "Would you like a drink?"

"I'd love a drink. What's your name, handsome?"

Offering my hand with a smile, I replied. "I'm James. And you?"

Her handshake was firmer than I would have expected. "I'm April."

"Nice to meet you. What's your tipple?"

"Just a glass of wine, please."

Once our drinks were delivered, I turned my body as April did the same. Immediately on display were a pair of rather lovely long legs, and it was obvious she looked after her body. And the pair of breasts on her chest were more than likely fake though suited her perfectly. As my eyes moved to her very pretty face, she smiled at me before sipping at her drink.

"Do I meet your approval?" she wondered.

"Not often a beautiful woman approaches a man in a bar."

"As I said, I'm out tonight because I want to get laid. And I had an inkling that you were not gay."

"Give off that vibe?"

"You look comfortable enough, but nearly all the gay men in this place are avoiding you because their sixth sense tells them that you're not gay. And while you might be polite about it, gay guys can take a hint, at least."

"Seen it happen before?"

"Plenty of straight guys come in here with their gay friends. On occasion, I've seen men who might have never considered themselves bicurious end up going home with a man. Hell, I've walked upstairs to the bathrooms and seen some rather eye-opening things."

"Can it get rather wild the later the night goes?"

She laughed at my question for a few seconds. "I won't say it'll turn into a full-blown gay orgy in here. You'd have to go to a gay sauna for something like that."

"Maybe my little brother can go there..."

"Not sure you'd want to escort him there. You will see a lot of gay sex in full view rather quickly."

"And what about you, April?"

Her hand ended up on my forearm. "I'm hoping to end the night in a good way. Bring in the new year with a bang, so to speak."

"Are you looking for just a little fun or something a little more serious?"

"Tonight, I'm just after some fun."

"I'm not much of a dancer, but would you like to head up onto the dancefloor?"

April loved the idea, sliding off her stool and almost dragging me up into the middle of the crowd. As soon as her arms looped around the back of my neck and she was meeting my eye level, I quickly glanced down to see that she was wearing flat shoes. Glancing back into her eyes and smiling, she said, "Yes, I'm rather tall."

The short skirt she was wearing definitely showed off a fantastic pair of legs. And the blouse was low cut, showing off some rather impressive cleavage. She wasn't slim, but I was left thinking her body would prove to be rather toned as the blouse was tight to her body. We danced our way through a few songs, managing to make some polite conversation despite the fact that the music was quite loud.

When we kissed for the first time, her lips were very soft, and her tongue was very eager. I was left on the back foot as she was very aggressive, very much taking the lead in a simple kiss. Not something I was used to though I found myself liking it quite a bit, particularly as her hands moved down my back to my arse. That was something I would usually end up doing.

"Damn," I exclaimed when we broke apart, "That's certainly a way to introduce yourself."

"I don't see the point in hesitating. When I want something, I'll do what I can to get it." She took a deep breath before kissing me softly again. "Come on, let's go grab another drink. My round."

The stools we'd been sitting on were still free, sitting at the bar as April ordered us both a drink. I stuck to liquor with a mixer, she ordered herself a colourful cocktail. Thanking her for the drink, I took a sip as I made sure that my body was turned to face her. I glanced up and down at her again as there was no doubt that she was a brunette bombshell. It was obvious she wasn't a lesbian. That had me wondering what a woman was doing in such a place.

"James, I need to tell you something..." She met my eyes and there was a hint of nerves. "I look like a woman, right?"

"Are you transgender, April? I figure that you're not a lesbian, considering that kiss we just shared, and straight women don't come to gay bars to pick up men, so that leaves the only other realistic option."

"Does that bother you?"

"Can I be honest myself? I guess being with a woman like you is a fantasy of mine."

A gorgeous smile formed as she leaned closer. "You can have your fantasy tonight if you want it..."

"You said you're only here to get laid... April, I'll be honest with you in return. I'm taking off in a couple of weeks. I'm joining the army."

"Then I can be your lover until you disappear. I'm only after a little bit of fun." She sipped at her drink again before asking, "How old are you?"

"Twenty-two."

"Thought you were younger than me. I'm twenty-nine."

"How long have you lived as a woman?"

"Only ten years. Explains the height and the fact my shoulders are wide. I'm surprised you didn't..."

"I just thought you were a woman who looked after herself. Met more than one muscular woman over the years. Plenty of them are in the gym lifting weights nowadays."

"Want a blowjob before we go dance again?"

"Huh?"

She laughed at my reaction. "Want a blowjob? We can head upstairs to the bathrooms. They're very nice in here because, well, you'll probably see when we head inside."

Sculling my drink had her laughing again. "Fuck it, I'd be stupid to turn that offer down."

Finishing her cocktail rather quickly, she kissed me again when we stood up, running my hands down her back towards her arse. She smiled as I gave each cheek a gentle squeeze while she did the same thing. Breaking the kiss, she moved her lips down my cheek towards my ear. "I hope I get your lips wrapped around my girlcock when I take you home with me tonight," she whispered, "I've got a nice one for you."

"Do you like to, um, what's the phrase? Top someone?"

"I love fucking hot young guys," she said, leaning back to meet my eyes, "I'm guessing that's something you've never done."

"No..."

"Even better."

Walking upstairs was an even more eye-opening experience than anything I'd seen downstairs. Walking into the male bathroom, April stated she didn't want to take me into the women's bathroom as they wouldn't like me being in there, we were greeted by the sight of a young man being bent over one of the sinks, a guy fucking him hard from behind with two guys lining up, waiting for their turn. The young man seemed to be loving it. April led me to one of the bathroom stalls, hearing more moans and grunts from behind two of the closed doors. We took one of the empty cubicles, April having me sit down and that's when I noticed the holes to either side of me.

"So they're real," I stated.

"Hopefully no one else sticks their dick through one of them," April stated after she locked the door and lowered herself down, "There's only one dick I'm sucking right now."

"Um, do you want..."

"When I take you home, handsome. I just really want to do this right now."

I didn't feel too self-conscious exposing my cock to her. I was far from a virgin though I would admit I'd only been blown in the bathroom of a nightclub once before. Her eyes lit up upon seeing it, always a positive reaction. I wasn't immensely hung or anything. Probably average length but I'd been told by more than one girlfriend that it was definitely nice and thick.

"James... I'll tell you now that I am bigger. Some guys can't handle that."

"I love hung girls..."

She ran her tongue up my shaft, her tongue then circled the head of my cock before she asked, "You've watched girls like me in movies?"