Best Wingman Ever

"Hey! Wanna go out for a drink?" Sarah bounded into the room like an excited puppy.

"Are you that desperate for a drinking buddy?" I asked back, pleased that my sister had considered me, but knowing that I was probably her last resort.

"It's not like that! I just thought we could go out for a catch up, since we've not seen each other for a few months."

"So it's nothing to do with you being the only one of your mates to come home for the weekend, while they're all still at uni?"

Sarah looked to the ceiling as she realised she'd been ousted and sighed, "OK, so I suppose if Vicky or Lauren were here, I'd probably be out with them, but when was the last time we went out for a drink together?"

"I don't think we've ever been out for a drink together."

"Exactly!" Sarah stared at me, impatiently waiting for an answer to her original question.

"Go on then, I could do with a drink," I relented, knowing my sister wouldn't take no for an answer.

"Yes! I'll go get ready!" Sarah's face lit up as though she'd just won the lottery, and she sped off to her bedroom to go change.

I lingered on the sofa, where I had originally planned to spend my evening watching whatever was on the ReelFilms channel, while swiping on girls in my area and not matching with a single one. As far as plans go, going out to a bar with my sister sounded much more fun.

After a few minutes, I heaved myself from the sofa and made my way upstairs. A quick shower and change of clothes later, I sat back down on the sofa and waited for my sister. Looking at the clock, it was already 8:30, and I wondered how long it would take Sarah to get ready. All the bars I knew would be busy by now, especially on a Friday.

Ten minutes later, I heard footsteps on the stairs again before Sarah appeared in the living room. She emerged wearing black skinny jeans that showed off the curves of her legs and her ass, a low cut but modest sparkly halter top that exposed her midriff, and a leather jacket to help tie her outfit together. Her mousey brown hair was left unencumbered as it flowed down her back and over her shoulders.

"Just need to get my shoes on, then I'm ready to go," Sarah informed me, as she sat on the sofa next to me holding her heeled boots in her hand.

"If Mum was here, she'd kill you for putting those on in the living room," I lectured my sister, knowing our mother would disapprove of outdoor shoes on her spotless cream coloured carpet.

"I know, I know. But they're clean and I'm going to tidy up the whole house before she gets back on Sunday anyway. She'll never find out." Sarah continued what she was doing without a care.

A few minutes later we were out the door and walking towards the city centre. Luckily, it wasn't far to go, and we each had a drink in our hand before the clock struck 9. As we turned away from the bar, we both saw a couple getting up from their table and dashed towards it before anyone else spotted it.

"So, how's uni going?" I asked as we sat down.

"It's brilliant! Like, it's great to be back home for a bit of a rest, but I love it! It's been non-stop, but every second I've not been doing uni work has been so fun. My housemates are great, too. We've got a really good mixture of personalities."

My sister regaled me with stories from the last few months while she had been at university. Most of them seemed to consist of getting drunk with her housemates on a weekday night, and then struggling to get up for classes the next day. It sounded exhausting, but it also made me regret taking a gap year, and not going to to university straight away.

I'd only taken a gap year because Sarah had done the year before, and had so much fun during it. So far, all I'd managed to do was masturbate three times a day and accidentally shift my sleeping pattern so much I'd become practically nocturnal.

"I know it sounds cliché," Sarah continued, "but I really feel like I've discovered so much about myself."

"Like what?" I asked, having started to zone out a bit as Sarah's continued stories of drunken antics were getting a bit repetitive.

"Like, I've learned I can get by on a couple of hours of sleep a night for a surprisingly long amount of time, or I'm more confident in new surroundings than I thought I'd be, or how much booze I can drink before I pass out. That last one I could have probably have done without knowing, but now I do anyway!"

My sister paused as she looked at the ceiling, "And then there's other things..."

That last bit caught my attention. Sarah was either trying to avoid talking about something, or was embarrassed to talk about it.

"Other things?"

"Y'know..." Sarah chose her words slowly and carefully as she spoke, "They say people experiment at uni..."

I could feel my sister's eyes searching my own for the confirmation that I understood what she was talking about. When she didn't find anything, she waited a few more moments before finally giving up.

"Sexually." Sarah stated matter-of-factly.

I felt my eyebrows involuntarily jump up, and could see Sarah was looking for some kind of response before she continued, "Oh, right," was all I managed to squeeze out.

"I know your sister's sex life probably isn't something you want to hear about, but if I were to talk to Vicky and Lauren about it they'd get all weird about it. Lauren can be proper judgemental, despite taking home a different guy almost every time we go out for drinks, and Vicky can be really stuck up at times and would probably think I fancy her if I told her I'd had sex with girls, just because she has a vagina and thinks she's God's greatest gift to men."

I stared at my sister wide-eyed for a moment, before struggling to compose myself in an effort to make out like her coming out to me was no big deal, "Oh, er, cool."

"You're weirded out aren't you? You're weirded out to know that your sister has sex with girls."

I thought about it for a moment, but all that did was put pictures in my head of Sarah furiously frigging another girl's pussy while on top of her, like an over-acted scene in a lesbian porno. I found myself beginning to get hard at the thought of it, and tried to shake the images out of my head.

"No, no, of course not. I just wasn't expecting you to just come out and tell me that tonight, that's all. I'm totally cool with it."

"Yeah? You're really okay with it?"

"Of course. You know you can tell me shit like that without any judgement."

Sarah let out a sigh of relief, "Thanks, Will. It feels good to just be able to tell somebody that and them not react weirdly."

I smiled at my sister to reassure her that I really meant everything was okay, and took a swig of my pint. Sarah followed suit, and a silence between us became apparent.

"So..." Sarah was the first to speak again, "how's my little brother doing for action? Did I see you on a dating app earlier? No girlfriend at the moment?"

"Nah, going through a bit of a dry spell at the moment really."

"Dry spell" was probably a bit of an understatement. "Biblical drought" would probably have been a more accurate term, but my sister didn't need to know that.

"Ah well, once you get to uni that'll change. Everyone sort of lets their hair down a bit. You'll get loads of action then. You're a good looking guy Will, you'll do well at uni."

"Er, thanks." It was a bit strange hearing my sister call me good looking. We'd always got on well as siblings, but we were never massively close growing up. Just good mates.

"Can't have you waiting that long to get laid again though! Let's have a look at your dating profile."

"Nah, it's alright, thanks."

It wasn't that I had anything inappropriate on my dating profile, it just felt a bit weird having my sister going over it.

"Oh come on, Will! I can give you some tips on what girls want to see on those things."

"Can't you do that without seeing it?"

"I suppose so, but that's no fun! And I can't tell you if it's shit without seeing it either."

"I really don't want you seeing it. Sorry Sarah, it's a no."

"Ugh, fine. You're no fun. Guess I'll have to get a few more drinks down you first. What'd you want?" Sarah stood up and pulled her purse out of her jacket pocket.

I still had half a pint left, but wasn't going to turn down the opportunity for another one, "Pint of Hoptown please," I smiled back.

While Sarah was busy at the bar, I took out my phone and loaded up my dating app. No new matches, no new likes. Typical.

I looked back up to see my sister walking back to the table carrying a tray with what was definitely more than two drinks.

"Pint for you, pint for me. Two shots for you, two shots for me!" Sarah looked very pleased with herself as she doled out the drinks and then sat back down.

I just looked back at her incredulously.

"What?" Sarah smiled at me, "We started late, we need to catch up! Cheers!"

"You're definitely a student," I said back to her as I raised one of my shot glasses to Sarah's and we clinked them together, then downed the colourful spirit drink.

As we were getting to the end of our pints, we tried to come up with somewhere else to go next.

"Ooh, I know," Sarah excitedly chirped, "how about that pseudo-classy place on the corner of Parliament Street?"

"Tennenbaum's? Yeah, I'd be up for that."

We walked for ten minutes to get to Tennenbaum's bar. It was fairly busy, but I'd seen it much worse. After a quick glance around, I couldn't spot any free tables, but I thought maybe one would free up as we got our drinks.

It was my round, so I asked Sarah what she wanted.

"Dunno, what you getting?

"Probably an old fashioned, they do a pretty decent one here."

"Ugh, you're such an old man," Sarah quipped back with a look of pure disgust, "but if you're having a cocktail, I'll have a long island iced tea please."

"If I'm an old man, you must be fucking ancient, and I think it's two-for-one until eleven if you get two of the same drink."

"I'm less than a year older than you dickhead, and in that case I'll have two long islands then please!"

"Yeah, I guessed you might say that."

I ordered our drinks and turned back to my sister as we waited for them. Sarah seemed to be staring off into the distance, until I looked in the same direction and realised she was looking at a pretty black-haired girl sat by herself at the back of a semi-circular booth table. She seemed to be dressed up for a night out, but sat alone with what looked like a half drunk Manhattan in front of her.

"She looks nice," Sarah said out loud while still looking in the girl's direction.

"Yeah," I agreed, wondering where my sister was going with this.

"I reckon we should go and sit with her." Sarah still didn't look away from the girl.

"She's probably with someone, or waiting for someone."

"No, I don't think so. There's only one drink in front of her, so she's definitely not already with someone," Sarah took her phone out of her pocket and turned on the screen, "and it's 10:47, so if someone's supposed to be meeting her, they're either really late, or they've stood her up."

The bartender set our drinks down on the bar, and I turned to grab Sarah's before placing them closer to her.

"Let's go sit with her," Sarah finally turned away from the girl and looked at me as she spoke to me.

What Sarah had said had made sense, and most likely the girl was alone. But I felt a bit creepy just going and sitting with a random girl by herself in a bar. I turned to grab my own drinks, then turned back to Sarah to try to talk her out of it.

Sarah was gone.

I looked back over at the girl and saw Sarah making a beeline for her.

"Sarah!" I called over to her in a loud but hushed tone, trying and failing to grab only her attention and no-one else's.

As I got closer, I could already hear Sarah talking to the girl.

"Hey, do you mind if we join you?" Sarah asked her, already halfway to sitting down.

The girl looked up towards Sarah, "Oh yeah, that's fine." She gave an awkward half-smile, that looked somewhere between just trying to be polite, and relief that her seclusion had ended.

"We saw you by yourself and thought you might like some company," Sarah smiled at her.

"Thanks, that'd be nice actually," the girl looked back at Sarah and then over to me. I don't know if it was the booze, the fact that I could barely remember the last time I'd had sex, or if I just hadn't noticed from a distance, but when she smiled at me, I felt a small flutter in my stomach and I realised just how beautiful she was.

"What you drinking?" Sarah asked the most important questions first.

"I just had a Manhattan, but I might go for a gin and tonic if I get another one."

Sarah turned to me before I'd even finished sitting down, "G and T please, Will."

"Oh, you don't have to!" the girl called out.

"Ah, he's fine." Sarah waved her hand in the air to dismiss me from the table.

I could hear Sarah ask the girl her name as I walked back over to the bar, but didn't hear the answer. I ordered two gin and tonics as the two-for-one offer was still going for a few more minutes, and waited for them to be made. I turned to face the table where the girls were sitting and saw the still unnamed girl get up and begin walking towards me. She smiled bashfully at me as she continued past and under the archway next to the bar where the toilets were. I picked up the two drinks from the bar and went back to the table where Sarah sat by herself.

"So, what do you think?" Sarah asked me as I sat down at the end of the curved pew next to her.

"About what?"

"Jasmine."

"I'm guessing that's the name of the girl we're now sat with?"

"No shit, Sherlock."

"Well obviously she's gorgeous, why?"

A devilish grin crept across Sarah's face, "We're gonna get you laid tonight, little brother."

I now realised this had probably been my sister's plan all along since she saw Jasmine from across the bar. She clearly felt as though I wasn't getting enough action now that she was getting plenty at university. Perhaps it was even her plan since I'd mentioned I was going through a dry spell. Either way, my sister could be extremely cunning when she wanted to be.

I wasn't sure how to respond to Sarah. If I'd been on a night out with mates and I'd seen Jasmine from across the bar with her mates and I thought I might have a shot, I may take my chances and try to hook up with her. But I was just out having a quiet drink with my sister for a catch up, or at least that's how I thought of it. I'd not even thought of the possibility of taking someone home tonight.

"Sarah, that's not going to happen."

"Why not?" my sister seemed almost offended.

"Don't you think it's a bit weird to be scouting for girls to shag while you're with your sister?"

"Yeah, that's true," Sarah pondered, "definitely don't mention we're siblings to her."

Sarah picked up her drink while looking slightly pleased with herself and started to relax back into the pew, as though our dilemma was solved and everything was agreed to.

"So that's it is it? We're doing this?" I asked her.

Sarah just looked at me and smiled, before her eyes darted to the archway near the bar, "She's coming back, just follow my lead, okay?"

I turned my head to see Jasmine returning, and flashed a nervous smile at her. I took in the entirety of her, as I thought about the possibility of getting to fuck her later on. Her dark skin was flawless, and the way she walked over to the table in her high heels made her ample tits bounce slightly in the form-fitting little black dress she was wearing. I began to grow hard as I imagined what she would look like out of it.

Jasmine sat back down at the table and shuffled slightly back around the pew, so she was closer to where she had originally been sat at the back of it, and on the other side of my sister.

Sarah picked up the drinks I had just gotten from the bar and placed them in front of Jasmine, "It's two-for-one, so you get two drinks! I promise we're not just trying to get you drunk. Well, maybe a little bit."

"Oh, thanks," Jasmine smiled sweetly at me, "you really didn't have to."

"It's no worries," was all I could come up with in response.

Both Jasmine and myself picked up a drink and took a swig. The air was getting quiet, but just before it turned into an awkward silence, Sarah spoke up with a suddenness that almost made me jump.

"Oh my God, I love your nails!" she squealed as she gently grabbed Jasmine's free hand.

"Thanks! I just got them done this morning!" Jasmine replied with the same excited enthusiasm as my sister, as she allowed Sarah to take her hand.

I zoned out a little as the girls made small talk about stuff I didn't really care about for a while. I would occasionally get pulled into the conversation by my sister, with her turning to me and asking my opinion, or sometimes just hitting my arm, but eventually the discussion somehow steered towards topics I actually had some knowledge on and time seemed to just disappear.

Before long, and seemingly out of nowhere, we all came to the end of our cocktails.

"Can I buy the next round? I think I owe you," Jasmine asked us both.

Sarah answered for both of us, "Thanks, that'd be nice. I'll come help you with them."

I assumed I was getting the same again, as the girls got up and walked off without asking what I wanted, which I was absolutely fine with.

I watched them both while I waited for them to return. I wondered what they were talking about, and more importantly, what my sister was telling Jasmine. At one point they both turned to look at me and continued talking. They both smiled as Jasmine made direct eye contact with me, then turned away bashfully as my sister continued to speak directly to her.

The barman set three drinks down on the bar next to them, and Jasmine grabbed two, while Sarah grabbed the last one and waited for Jasmine to lead the way back to the table. Jasmine set my drink down in front of me as I thanked her, then sat down at the other side of the semi-circular pew and began to shuffle along to the same spot as before. Sarah then followed suit by sitting on the other side of Jasmine, and shuffling along with her until she was sat closely next to her.

"Move up Will, you're miles away!" Sarah called out from the other side of Jasmine.

I nervously looked at Jasmine to make sure there was no protest to me moving closer to her, and when she smiled back, I awkwardly shuffled along to sit as closely to her as I dared.

"There we go, that's much cosier," Sarah grinned.

At this distance, I could smell Jasmine's delicate perfume as it wafted through the air.

"Shall we make this our last round here?" Sarah asked, more to Jasmine than I.

Jasmine paused a moment before responding, sounding slightly unsure of her answer.

"Yeah, okay," she nodded. "Sorry if I seem a bit nervous, I've just never done this before," she smiled as she looked away from Sarah.

Sarah rested her hand on Jasmine's arm, "That's okay, neither has Will."

"Oh, really?" Jasmine turned to me with eyes that were looking for an answer to help steady her nerves.

I didn't know what exactly we were talking about, but I remembered Sarah telling me to play along earlier, so that's what I did.

"Yep, first time," I nervously laughed back.

"Well then," Jasmine seemed to get a small boost in confidence, "to first times." She picked up her glass and raised it in front of her. Sarah and I did they same, and touched them both to Jasmine's glass.

Jasmine brought her glass to her lips and knocked back the entire cocktail in one go. I looked at my sister, who raised her eyebrows and smiled at me, then did the same thing, throwing her head back in a display of solidarity with Jasmine.

After placing her glass back down on the table, Sarah fished her phone out of her bag, "Right then, I'll get a taxi for us."