A/N: I miss Addison, you guys
The first time happened when Addison was still married to Derek. He wasn't home, and he hadn't been for nights, and she'd had too much to drink and you had taken advantage.
Even back then, you had always been the one who knew just a little bit more about how the real world worked, and Addison had always been just a little too trusting with people she loved.
She was also a little too talkative when she had too much to drink.
And finally you couldn't take it anymore. Because another thing Addison was was beautiful, and when she looked at you with those big sad blue eyes and asked if you knew why her husband didn't love her anymore, there was nothing you wanted more than to find your brother and punch him in the face.
But instead you placed your palms on her cheeks and wiped away the tears with your thumbs. And then you kissed her. Hard. And she was warm and her lips were soft and tasted like wine, and the gasp she made when you kissed her went straight between your legs.
So you slipped your hand under her tight black skirt and rubbed your fingers against her until she was squirming beneath you. But you didn't stop — and she didn't stop crying — and when she finally came, you held her against you and told her your brother was an idiot if he didn't love her anymore.
•••
The second time happened after she and Sam ended but before she and Jake really began. Because Addison wasn't a cheater and she wouldn't do that again. Not even with you.
But Sam was off with some floozy (Addison's words) and she was alone and a baby wasn't looking likely, and you thought she deserved better than Sam anyway.
You'd always liked Sam. You had. And you knew, more than most people, that Addison was no picnic. You'd seen her at her worst to be sure of that. She was stubborn and demanding and sometimes needy and required an endless amount of patience.
But she was also insanely smart and amazingly kind and she loved people more deeply than most anyone else ever did. And she deserved more than someone who couldn't see that.
But there were only so many ways you could tell her that she deserved better without it getting back to Sam and causing discord, and Addison wasn't listening when you talked anyway, because she was lonely and desperate and she kept muttering things like, "Well, maybe if I had …"
So you did what you had to do. You plucked her wine glass from her hand and pushed her back on the couch and let her clothes fall on the floor.
And when you had two fingers buried inside her and your other hand fisted in her hair so tight she had no choice but to look at you, you told her again that she deserved better.
And you thought that maybe this time she finally listened to you.
•••
The third time came after the inevitable. You had always feared it would come to this, even if you hoped for her sake it wouldn't.
But lucky in love wasn't something Addison was, and when she sank to the floor after Jake left her behind for the last time, you were the one who picked her up and put her in bed.
You waited until Henry was asleep — because you were nothing if not a good aunt — and crawled in bed beside her.
"You were too good for him anyway," you told her, and you were starting to feel like maybe this was becoming a pattern, but you didn't have time to think about that too much because this time she was the one to reach for you. She kissed you on the lips, then balanced on her knees and soon her clothes were nowhere to be seen.
But instead of making a move, you paused and asked "Are you sure?", which surprised you, because you never asked before, but this time felt different and you needed to know.
But she nodded, and you knew she meant it, so you stopped talking and kissed her back.
When you were finished, you held her in your arms, eerily similar to the first time. Right before you were about to fall asleep, you heard her speak.
"You're the only one who's ever always been here for me. Please don't leave me," and she sounded so small and so afraid all you could do was squeeze your arms tighter around her and murmur the first thing that came to mind.
"I won't."