Disclaimer: Any television shows, movies, books and other copyrighted material referred to, along with the characters involved, are the properties of their respective owners. This story is completely fictional and isn't intended to be taken seriously.


"What's it like being with a girl?"

The question jolts you out of your haze. You had been looking at a choice of women in the bar and now you're staring at your best friend with a look that you're sure says you're confused and incredulous.

It isn't a fair trade, really.

"Uh, Gabby?" you say in response. You think that's a fair trade though. How in the world are you supposed to describe being with a girl? Because in your opinion, actions are better than words in so many situations and this is one of them.

"I'm curious. I mean, I've kissed a girl before but that was back in college and I was drunk at a frat party so I'm not even sure that really counts," she says.

"So you ask your gay best friend to satisfy your curiosity?" you reply, raising an eyebrow as you speak. If she was curious about sex with a woman then why didn't she just try it out?

"Well, yeah. You like women. You fuck women. So I'm pretty sure that means you could tell me," she shrugs. Its like, the question should be awkward but its not because its Gabby and you're you.

"Uh…well, its kind of hard to explain. I mean, kissing a girl isn't really any different than kissing a man aside from the missing facial hair and the softer lips. But having sex? I don't know. Obviously the parts are different. But I feel like its more intimate than with a man. I wouldn't know, exactly. I'm a gold star," you say. You're rambling, but you're fairly certain you got your point across.

"What's that mean? You're a gold star?" she asks.

Oh boy, you really need to pull out your seasons of The L Word.

Actually, that's not a bad idea. She'd get the idea of sex with a woman real quick.

"It means I'm a lesbian that has never had sex with a man," you explain. Basically, penises are gross and you don't ever want to get up close and personal with one.

"Oh," she says. She takes a drink of her beer and it falls quiet between the two of you once more. You decide to go back to scoping out girls that could possibly want to go home with you because really, you haven't had sex in a while and that sucks. A lot.

"What's it feel like?"

Again, you're jolted out of your thoughts. You're kind of intrigued by why Gabi wants to know this.

"I'm sure you've gotten off by yourself before. It's like that, only on another woman. You have to find what makes her feel good. I like to think of her body as a treasure map," you say. You shrug. "Its fun finding the spots that make her tremble and its even better when you find the spot that makes her scream." Even though its kind of dark in the bar, you see that Gabi blushes slightly.

"What's got you so interested? Or should I say who?" you tease, smirking at her. She avoids your eyes but kind of smirks back.

"Its…I don't know. I'm curious. I was thinking about this the other day and I guess I've always found girls attractive, but I've never really thought about getting with them," she answers.

"Well, I can sit here and preach to you all day about sex with a female but honestly, its easier to just do it," you say. And its true. Because words really don't cover how awesome it is to have sex with a woman.

"Yeah, that's…actually, that's kind of what I was getting at," she says. She's really avoiding looking at you now and that makes you kind of nervous.

"What do you mean?" you ask. Because if she's suggesting what you think she's suggesting, you don't even know how to handle that.

"Would you consider having sex with me?" she finally blurts out. Yeah, she was suggesting what you thought she was suggesting. And now that the ball is kind of in your court now, you don't actually know what to say.

On one hand, you're flattered. Because Gabi is an incredibly attractive woman and for her to ask you is kind of an ego booster. On the other hand, however, you're kind of nervous because what about being friends and partners at work? If you were to have sex with her, you'd have to face her every day after that. And it would be a little difficult because you'd know what she looks like naked and you would know how to make her come. You're pretty sure that wasn't covered in your employee handbook.

"Uh, Gabs, are you sure? Because that's kind of a big commitment," you say. It is. It would affect your work relationship and your friendship and you don't want to compromise either in a negative way.

"I know it is. That's why I'm asking you. You're my best friend and I trust you with this and I know if I make a fool out of myself, you're still going to love me at the end of the day. I'd rather it be you than some random woman who would probably expect me to know what to do," she says, exhaling deeply.

You close your eyes and breathe in deeply, counting to ten before you release your breath. When you open your eyes, she's staring at you and you never noticed it before, but you can clearly see lust in her facial expression.

She's never actively looked at you like this and it kind of throws you for a loop. She wants you. She wants you.

And you kind of want her too.

"I…alright. All right. We can…do this. But, if we do, you have to promise me that you aren't going to freak out the next morning. You're my best friend and I don't want to hurt that," you say. You have to stress that you don't want your friendship with her to suffer. Because you don't think you could handle not having her in your life.

"Yes, I promise. That's why I asked you. Because I know I can go to you for anything and I swear I won't make things awkward," she says quickly. You nod a couple times.

You just agreed to have sex with your best friend.

You need a drink.

You signal for the bartender to grab you another vodka tonic and you raise your eyebrow at Gabby in question as well. When she nods, you signal for him to bring her another too.

As you take a long sip from your glass, you feel a hand on your thigh and its closer to home than you thought it would be.

One drink isn't going to be enough. So you call for two more.


You make it back to your apartment with Gabby in tow behind you and you breathe a sigh of relief when you realize Severide isn't home.

At least that's one awkward situation you get to skip because you don't even want to think about trying to explain to him why you're taking Gabby to bed.

"Do you want anything to drink? I've got water and raspberry tea," you question. Even though you had a few drinks, you're still quite coherent. And even though you're craving another drink (because doing this semi-sober makes it all the more real), you know it would be a bad idea.

"No, I'm alright," she says. You nod and you feel like you've done that a lot this evening.

You look at her and you see that she's looking at you. By now, if you had taken a different woman home, you'd have her half naked in your bedroom but this is Gabby and you don't want to rush it. Its her first time with a woman, so that automatically means it should be special, and its her first time with you and that makes you want to treat her like a princess.

So you swallow your fears and you step closer to her until your hands are on her waist and you can feel her warm breath against your lips.

"Its okay," you murmur. And then you kiss her.

Her lips are softer than anything you've ever felt. And when her tongue brushes against your lips, your knees weaken. Aren't you supposed to be the one seducing her?

Either way, its game on. You aren't sure where the strength came from, but suddenly you're picking her up and she's wrapping her legs around your waist as you walk up the stairs. Your lips are still attached and you have no idea how you haven't fallen over yet.

You swing your bedroom door open and then kick it closed and carry Dawson to the edge of your bed.

"This is what you want?" you ask, breaking away from her. You have to make sure. You need to know that she wants you on her, in her.

"Yes," she answers. Her voice is rough and it hits you hard in your stomach. This is what she sounds like when she's turned on. You are turning her on.

You've never wanted something so much.

It doesn't take long before your lips are back on Dawson's and her shirt is off lying somewhere on your bedroom floor. Her bra is nice, and seeing her boobs in her bra is pretty nice too, but you really don't give a damn about that. What you want is underneath. It comes off in a hurry too. She's shirtless underneath you and you have so much new territory to explore. She's beautiful.

You take your time. Each time she gasps and puts her hands in your hair, you take longer. She's applying gentle pressure on your head, to get you where she really wants you, but you're not quite there yet. You want to get to know her body because if you're only going to ever do this once, you're going to do it right.

"Shay. Shay, please." She's gasping. You smirk against her stomach and take your hands to the zipper of her jeans. Eventually, those are gone too, along with her underwear.

Now she's naked underneath you and you're pretty positive you've never seen such a wonderful, beautiful sight. Her nipples are hard, her stomach muscles are clenching and there's a light sheen of sweat over her body from getting worked up.

"Last chance to back out," you whisper in her ear. And then your tongue is gliding down her neck.

"I'm not backing out," she says. Her voice is serious but you can still hear the lust she's feeling. And you knew she wouldn't back out, if only for the reason that it would completely suck to not get off at this point. But you'd like to think it means more to her than that. She's not backing out because she wants this, and she wants you.

Your answer comes in the form of rubbing slow, tiny circles on her clit. Her resounding moan is more than enough to make your self-esteem shoot through the roof.

"Fuck. Yes."

Basically, making love to Dawson is everything you never knew you wanted. And going down on her is probably your new favorite thing. When her grip on your hair tightens and you feel her spasm beneath you, you slow down your thrusts and your tongue licks lightly, to help her come down easy. When you make your way back up her body, her eyes are open watching you. You have to smile.

"Hey," you murmur. She smiles lazily at you.

"Hi," she whispers back.

"You okay?" you ask. You don't want to overdo it.

"I'm great. That was great," she says, grinning happily. "I see the appeal." You laugh and lean down to kiss her.

And then she takes you by surprise because her legs are locking around your waist and suddenly you're turning over so that she's on top of you. Its kind of odd being in this position. Most of the time when you have sex you're on top and the girls you've been with haven't ever really tried to change that. But the change is for the better because if you thought Gabby underneath you was hot, then Gabby on top of you is fifty times better. You've been turned on for the past you don't know how long but its seriously hitting you now.

"You're going to have to help me," she whispers. Her breath hits your mouth and its warm and oddly comforting.

"Its okay," you whisper back. "Just do what you think is right." She nods, as if to reassure herself that she can do this and then leans down to kiss you.

Ten minutes later, your clothes are completely gone and she's kissing down your body like a pro. You don't think you've ever been this turned on before.

Her tongue is making a map out of your body and you want to scream for her to get to the point where x marks the spot. But you stop yourself because you don't want to rush this. Yes, you're fairly certain this could be considered a form of torture (one that surely beats waterboarding) and yes, you've never been so desperate to come. But there is no way in hell you want this to stop. It's too delicious of a feeling.

You hiss when her nose bumps against your clit as her tongue makes a gentle sweep below. And then you want to laugh because her head pops up, concerned. She's worried that she hurt you and it's probably the cutest thing ever.

"Are you alright?" she asks. You do laugh this time. You take the hand that had previously been gripping the sheets beside you and run it over her cheek, brushing a strand of hair behind her ear.

"Yeah, I'm alright. Great, actually. It felt really good," you murmur. Your voice is slightly deeper than normal because you're aroused and you see that it has an effect on her. Even though she blushed at what you said, her eyes darkened at your tone.

She doesn't say anything but she goes back to what she was doing before and you close your eyes. You're kind of embarrassed because you know that you aren't going to last but if you're going to be completely honest with yourself, you don't even care. You aren't positive there would be anyone with the power to last with Gabby giving them head. So you bite your lip hard and use one arm to anchor yourself to the headboard of your bed.

"Gabby," you hear yourself groan. You're close now. One hand is on your headboard and the other is at the back of her head, pushing her where you want her to be. There is no way this is her first time.

"Fuck," you gasp. You're coming and your body is shivering in a way that you never want to stop. The hand at the back of her head is now pushing her away gently and she gets the idea because she's sliding up your body slowly, a small smile on her face. You couldn't have her keep going. It felt so good it almost hurt.

"How'd I do?" she whispers, resting her head on your torso, right below your breasts. You look down and catch her eye.

"A plus," you say. And it's so true. You're not exactly proud of this fact, but you keep a tally of how many women you've slept with since you lost your virginity at age 17. And out of the women you've had, including Gabby, she's been the absolute best.

Its quiet between the two of you now and you think that this situation is completely odd. You just slept with your straight best friend. Up until two hours ago, you hadn't ever entertained the thought of getting Dawson into bed and now that you have, you kind of don't want her to leave. What's more, is that it was literally the best sex of your life and you are breaking every rule in your sex rulebook because now you're spooning her tightly and wishing her a good night. You haven't spooned anyone after sex since Clarice and you don't know what the fuck possessed you too now, but she feels good against you and you have an insane urge to cuddle the hell out of her.

So you do.

You can't say you're mad you broke your rule, either.


The next morning goes better than you thought it would. Dawson woke up to the sound of your alarm and didn't even flinch when she realized the two of you were wrapped up together.

You take turns taking showers, though the idea to just share one crossed your mind. You've already seen her naked, so why not?

But you don't and by the time you get out of your own shower and get dressed in your uniform, Dawson has breakfast on the stove and a cup of hot coffee on the counter.

You aren't sure what to say or what you're allowed to do, but you throw caution into the wind and kiss her cheek gently and thank her for the coffee when you pick up your mug and notice that its made exactly how you like it. Maybe sleeping with your best friend has its perks.

She sets your breakfast on the table and you notice that she only made enough for one.

"You're not staying?" you ask. You frown when she shakes her head.

"No, I've got to get home and get changed and grab my go bag for work," she says. That's when you notice she has on a pair of your sweatpants and a department softball t-shirt of yours. And until that point, you never really understood the allure of having a lover (though you aren't quite sure you can label Gabby as that) wear your clothes. But now you see and you have to hold yourself back from pushing her against the counter and making her beg.

But instead you nod and take a bite of the eggs she made you.

"We're…alright, right?" you question, looking back up at her. The smile on her face is enough to get you to relax.

"Yeah, we're alright," she murmurs. She walks closer to you and only hesitates for a small second before she kisses you slowly.

"I'll see you at work," she says. You nod and smile and you don't move until the sound of the door to your apartment closing registers with you. Then you're sliding down into a chair at the table and it takes you a moment but you start to eat the breakfast she had made.

It hits you that you kind of want this to be every morning. You want to wake up to her and her warmth against your skin. You want to hear her sing along to the morning radio as she showers. You want to see her in your kitchen making coffee and you want the feel of her lips against yours at your disposal.

This wasn't supposed to happen. It was supposed to be fun and an experience that Gabby had with a trusted friend. You were supposed to wake up the next morning and joke about what the boys would do at work.

Perhaps it should have been yourself that you should have worried about freaking out.


What happened doesn't exactly disable you from functioning around Gabby but you're not exactly sure of yourself either. Where normally you wouldn't hesitate to throw your arm around her shoulders when you walk side by side, now you keep your hands in your pocket and a few inches of space between your body and hers.

Its not that you don't want to, but it's that you can't. You don't want her to think that you're going to be typical and call up a u-haul. You want to give her the space to process what happened and what she felt. You know how you feel. You know that your feelings for her did a complete 360. You went from thinking she was attractive but your best friend to a girl you want to date the fuck out of.

But Gabby stated that this was solely to see if she was at all attracted to women sexually. If you had any say in it, then yeah she was, considering she was wetter than anyone you had ever been with. But just because she liked the sex doesn't mean she liked you. Just because it was your name that she gasped as she came doesn't mean it was because she had any kind of feelings for you.

You're going to have to suck it up and be her best friend. You'll get over it. It's never good to get interested in straight girls anyway.


Weeks pass since you and Dawson had sex and really, everything has changed. But it hasn't been bad. In fact, it's been pretty good. Dawson seems to have kicked the idea of being with Casey to the curb. Which is good because you don't like the idea of them together. But Dawson has been a lot more affectionate with you. It's throwing you for a loop.

You want to ask her on a date, but you aren't sure if it would be received well. Yeah, she curls herself around you when you're on the couch together. Yeah, she rubs your back sometimes after a long shift. Yeah, sometimes she comes over and cooks you dinner when you're too lazy to do so. And yeah, sometimes she looks at you like you want her to always.

But you can't tell if it's because she might have feelings for you or if it's because she feels like your friendship is stronger after sharing what you shared. Maybe she feels like she can trust you more? Maybe you've helped her in finding her sexuality and so she feels obligated to be closer to you?

You don't know. You wish you did. Because this is the first time you've been unsure when approaching a woman. You're not exactly a player like Severide, but you have never had problems getting the ladies. You've always been sure of yourself; you've always had confidence. You're charming, you're polite, you're pretty easy on the eyes and not to be cocky, but you're really fucking good in bed.

But Gabby makes you nervous. She's the first woman since Clarice that you genuinely want to pursue and she's been your best friend for the past four years. And either you could make a total ass of yourself and ruin your friendship, or you could have a solid relationship built on trust.

Except your confidence is failing you and you're becoming a total chicken shit.

"Hey, what are you doing tonight?" Dawson shows up in the back of the ambulance suddenly and you jump from restocking the supplies.

"I've got a date with a six pack, the DVR, my couch and then I might be player and two-time with my bed," you joke. Dawson laughs deeply and grins at you.

"Well, if you want to switch it up and two time your couch with mine, that option is available. I'm cooking chicken marsala," she says. And you're sold. One, you'll be with Gabby and two, you'll be with Gabby's cooking. There is no wrong there.

"I might even two time my beer and bring some wine," you add, grinning back at her. She laughs again.

"Alright. It's a date. Be there at eight," she says. She winks at you and then pushes off the back of the ambulance to walk toward the break area in the department.

"It's a date," you call back to her. She turns on her heel and smiles. Then she's disappeared into the building and you're left alone with the ambulance and a fuck ton of IV packets.

A date. With Dawson.

What?


You're not exactly sure if this was a normal date or a friend date. But either way, you took a really long shower and made sure you were presentable before dressing casually in some faded jeans and a loose t-shirt. You've got the wine in your hand and you picked up some of Dawson's favorite ice cream from the store.

When she opens her door, you can't help but smile like an idiot. She's in jeans and one of your henleys that you left here some time ago.

"Hi, come in. Dinner is almost ready," she says. She walks back toward the kitchen and you kick your shoes off at the door before following her.

"It smells good," you say. "I brought booze and a surprise."

"I like surprises," she says, raising an eyebrow. You hold up the bag that has the ice cream in it and she grins.

"You're seriously the best," she laughs. You nod, because yeah you're pretty awesome, and put the ice cream in the freezer.

It isn't long before dinner is on the table and the two of you are joking around like you always do. Dawson is seriously one of the best girls you know. She's funny, she's genuine, she cares so much and she is completely gorgeous. And she can cook.

Basically, she was the poster woman for what kind of girlfriend you wanted.

Its quiet for a moment and you want to approach the subject of dating but you aren't quite sure how to do that.

"So," you start," this is a date?"

"It is," Dawson says, taking a bite of her chicken. She's looking right at you and you don't know what it means.

"Like…a date or a date?" you ask. And you're pretty sure there was a better way of putting that but oh well. She laughs.

"It's a date," she says. Your eyes dart to hers. "Is that alright?" She sounds unsure now.

"Yeah. I mean, yes. Absolutely. I've wanted to ask you on one for a while but I wasn't sure how you felt about that and I didn't want to approach the whole dating thing because it is so typical to fall for your straight best friend, especially once you've had sex, and I didn't want to put you in that position," you're tripping over your words and you finally just shut up because you're making an idiot of yourself.

Dawson is giggling and you can feel the heat on your cheeks. You are such a fucking idiot.

"I kind of thought you did. But then you didn't make any moves so I figured I'd have to initiate it," Dawson says. You nod.

"Yeah. I didn't want to be presumptuous. I mean, you asked me as a trusted friend and I didn't want to think that meant you wanted me as a girlfriend," you say.

"I didn't at first. I came to you because you're my best friend and I trust you. But then I couldn't stop thinking about it. I mean, not just the sex but the idea of dating you," she murmurs.

"Awesome," you grin. Dawson wanted to be your girlfriend. Fuck yeah.

Dinner ends and you find yourself on the couch with a glass of wine in front of you and Dawson curled into your side while you watch Ted. You can't focus on the movie because why would you care about a bear that could talk and do drugs when the most beautiful girl was laying next to you? So instead of paying attention to the movie, you pay attention to the sound of her breathing. You pay attention to the feel of her beneath your arm with her head on your chest. You pay attention to how warm she is and how good she smells. You get absolutely lost in her.

And then its four hours later and approaching one in the morning. Dawson is walking you to the door and you really don't want to leave.

"So I guess I'll see you tomorrow morning?" you question, looking at her. She nods and takes your hand in hers. There's a funny smile on her face.

"Are you ever going to ask me or am I going to have to do that too?" Dawson says, raising one of her eyebrows. You blush and look down. Once again, you didn't want to be presumptuous.

"Want to be my girlfriend?" you finally ask.

"Yeah, I do," she answers. You can't hold back your grin and you pull her to you so you can kiss her. Her mouth is warm and you never want to let her go.

"See you tomorrow," you murmur as you separate.

"Yeah, see you tomorrow," she whispers back. You give her one last quick kiss and then you're out the door.

You can't keep the grin off of your face as you ride in the back of a cab and you're pretty sure the driver probably thinks you're insane. But that's okay.

Dating your best friend definitely will have its perks.