A/N: lots and lots of background about our two ladies in this chapter. Possibly too much? I don't know - but as you can tell, I struggled to write this hence the delay. Please let me know your thoughts!

Ruby's eyes snapped up from her phone screen as she heard the door to the penthouse click open. Hesitating, she quietly got off the couch and tip-toed towards the hallway. All was silent. Slowly, she peered around the door frame. Emma and Regina were standing side by side with identical smirks on their faces.

"What are you creeping out here to see?" Regina asked, a knowing glint in her brown eyes.

"I … um … I wasn't creeping," Ruby blushed, stepping into the corridor. "I just … heard a noise and wanted to … um … check it out."

"Yeah right," Emma snorted. "You wanted to see if you'd catch us making out up against the wall."

"I didn't!" Ruby protested but Emma and Regina just started to laugh.

Regina shrugged off her coat, took Emma's too, and hung them up in the closet before moving further into the penthouse. Emma and Ruby followed, the blonde still laughing and the brunette still embarrassed.

"How was Henry?" Regina asked as she sat down on the couch.

"Good as gold," Ruby replied, resuming her previous position as Emma sat down right next to Regina, her arm around her shoulders. "How was your date?"

Emma turned to regard Regina, waiting for her answer. The brunette smiled up into Emma's face before answering.

"Perfect."

Emma leaned down and kissed Regina softly. They might not have wanted to put on a show for their nosey friend when they first got home but neither woman could wait any longer. Ruby didn't look away. The kiss was too sweet and beautiful to miss.

"Well, I'll leave you to it," Ruby said when they broke apart. "I guess your first date isn't over since you both live here."

Regina's cheeks flushed slightly but Emma looked uncomfortable. Ruby didn't notice however as she was already gathering her handbag together and heading towards the door. Regina followed, thanked Ruby for her help, and promised to call her the next day with the details. The two had been best friends for years and nothing was a secret between them any more, although Regina wasn't sure how comfortable she'd feel talking about sex with Emma with someone who could now be called a mutual friend. When Regina returned to the living room, however, Emma was gone.

Regina checked the kitchen and then walked towards Henry's room. She put her head around the door, smiling at the sight of him sleeping soundly, before continuing her search for the blonde. The closed door of the guest bathroom told her Emma's location and she turned back to the living room to wait for the blonde there.

She appeared ten minutes later.

"Everything ok?" Regina asked as Emma sat down beside her again.

"Yeah," Emma nodded but from her tone, Regina knew something was wrong.

"What is it?" she asked, turning to the blonde. She shook her head dismissively. "Emma, what's happened. Tell me, please."

"Nothing," Emma said. "It's stupid, forget about it."

"I'm not going to forget something which has upset you," Regina said softly. "Was it something I said? Or did something happen whilst I was saying goodbye to Ruby?"

Emma sighed and leaned forwards, her elbows resting on her knees and her head in her hands. Regina looked even more concerned and placed her hand tenderly on Emma's back. For the first time in their relationship, the blonde flinched at the touch.

"Sorry," Regina said, removing her hand at once. "But, Emma, please talk to me. I'm starting to worry."

Emma closed her eyes and bit the inside of her mouth. She needed to get control over her raging emotions before she could begin to have this conversation. She concentrated on everything which had gone so right that evening. Their date had been wonderful; conversation had flowed naturally throughout dinner and Regina had laughed at all of Emma's jokes. The carriage ride home had been filled with kisses and caresses before they had planned their trick on Ruby. Yes, the evening had been perfect. But now Emma was worried about what was about to happen. She tried not to think about how their previous conversation on this subject had gone. She really, really didn't want to ruin the end of the date.

"I can't have sex with you tonight," Emma said at last as she looked up at Regina.

The brunette had thought of several things which might have been worrying the blonde woman but that was certainly not what she was expecting.

"What?" Regina frowned. Yet again, Emma Swan had stunned her into (almost) silence.

"I can't have sex with you tonight," Emma repeated. "I want to … I really, really want to Regina but I can't."

"Who said we were even having sex tonight?" Regina asked, trying to work out why Emma had got so worked up over something which they hadn't even hinted at throughout the date. Well, with the exception of their many, many kisses, she supposed.

"Ruby, for one," Emma pointed out. "And I kinda thought you were expecting that too."

"You think I put out on a first date?" Regina quipped, trying to lightened the mood. From the alarmed look on Emma's face, however, she failed.

"Shit, no, I didn't mean to offend you. Fuck, I've really screwed this up haven't I," Emma groaned, dropping her head back into her hands.

Regina wanted to reach out and touch Emma again but she didn't, not after how she had reacted last time. Instead, she tried to reassure the blonde with words.

"Emma, I know our relationship or whatever this is didn't exactly start in the most normal way and we're probably pretty confused in terms of where we're heading and at what stage we're at, but I had no preconceptions about where tonight would lead. Just so we're clear, I don't sleep with someone after one date but as far as I'm concerned, we're way past our first date. But that doesn't mean I was expecting for you to jump into bed with me tonight. Whether I want that or not, we both have to be ready to move forwards before anything else happens, right?"

Emma nodded and sat upright again. She smiled weakly at Regina and wiped her eyes. She wasn't sure quite why she had gotten so stressed. Well, that was a lie, but she didn't want to have to tell Regina why she was worried. The big brown eyes staring back at her however were simply pleading for the truth. So she took a deep breath, and told it.

"You know I went to the clinic this morning," Emma said.

"I know," Regina nodded, trying to keep all traces of emotions from her face.

"Well, I won't have my results until next weekend. I'm trying to think positive but I'm really scared. What if I've …," she didn't want to finish that sentence so she stopped, took a deep breath and continued. "I need to wait to find out if I'm clean before I'd ever let you … touch me. I really, really like you, Regina and I think the two of us together would be amazing. But I'm not going to risk your health just for our pleasure."

The corners of Regina's eyes crinkled in a way that made Emma want to kiss the lines away. A mixture of adoration and sadness crossed the beautiful features.

"I'm sure you're absolutely fine and one hundred percent healthy," Regina assured her. "But I also think it's very sweet, firstly that you're so considerate and secondly that you've got yourself worked up into such a state over this. I had a wonderful time tonight, Emma. And yes, I could have easily been persuaded to fall into bed with you. But I hadn't forgotten about your appointment this morning either and I think it would be sensible for us to wait, just to be sure."

Emma smiled sadly. "I wish we didn't have to," she admitted. "I've not felt like this about someone for a long time."

"Me neither," Regina said, reaching out and wrapping her hands around Emma's neck so she could pull their mouths together.

"Can I ask you something?" Emma said when the kiss ended.

"Anything," Regina assured.

Emma swallowed. She hadn't wanted to bring Dani up during their date but she still had several questions about Regina's deceased wife which she needed answers to. But she also didn't want to upset Regina by prying.

"It's about Dani."

Regina pulled back but didn't move from her position besides Emma. Instead, she turned her body so she was sat cross-legged facing the blonde and encouraged her to mimic her position. Emma did at once. When they were both settled, Regina nodded for the blonde to continue.

"It's been four years since she died," Emma began, "and I was just wondering how long you guys had been together and what your dating history since is. Only tell me what you're comfortable with though," she added.

"Will you do the same for me?" Regina asked. "I'd like to know about your past too."

"Ok," Emma nodded.

Regina paused and then got to her feet. Emma watched as she headed over to the glass liquor cabinet and pulled out a crystal decanter. She gestured with it to the blonde who nodded her approval. Less than a minute later, a glass of amber liquid had been placed in Emma's hands. She sipped it. It was delicious.

"Apple cider," Regina explained at the look of intrigue and delight on Emma's face. "I make it myself."

"It's amazing," Emma said, taking another sip.

Regina cupped her own drink in her hands. She had thought the extra bit of alcohol would have given her the courage she needed but it was still difficult. She hated talking about Dani but she also hated what had come after her death and how Regina herself had behaved. She just hoped Emma would understand.

"Dani and I were high school sweethearts," she said after a long silence. "We met when we were fourteen. I already knew I was gay and Dani was coming to the same realisation. We didn't get together until we were sixteen though, after two years of awkward friendship and flirting. We were each other's firsts for everything. She proposed before I went off to college but I turned her down. There was no way I wanted to be engaged when I was eighteen. I think she thought it was the only way we would survive so many years apart but I knew better. It wasn't easy; her at Harvard and me at Yale, but we made it work. I proposed to her on the day of her graduation. Less than a year later we were married and living here. Dani's grandfather had died and left her a small fortune, by the way, that was how two twenty-four year olds were able to afford this place. Henry came into our lives a year later and then, well, then she was gone."

Regina drained her glass and moved to refill it. Emma's heart ached for Regina and the loss and pain she had endured. When the brunette returned, Emma reached over and squeezed her hand, trying to let her know she understood. Not that she could ever understand truly how Regina felt, of course.

"Henry and I kept to ourselves for a couple of years. I wasn't interested in dating anyone and rarely even met new people. The job in my mother's law firm helped and slowly I began to feel more like myself. I still didn't want to move on from Dani but I started to need, crave, physical affection again. There were a couple of lesbian bars near my office and I started going there after work a few nights a week. Sometimes I met someone, sometimes I didn't. It never went further than making out on the dance floor or a fumbled grope in the toilets. Not unless I knew them. A few of the lawyers in my office turned up once and I got involved casually with a couple of them. It didn't last long and it made work awkward for months. After that, I went back to finding strangers. At least that way I knew I wasn't going to get my heart broken."

Regina stood up and walked to the high window. She opened it and looked out into the street below. The park beyond was dark but the streetlights illuminated the empty sidewalk. She breathed in the cold air and felt the tears drying on her cheeks. Eventually, Emma's arm looped around her waist as the blonde came to stand beside her, saying nothing, and simply content to be there for her. After a while, long after they had both started to shiver, Regina closed the window and led the way back to the couch.

"We've all done things to fill the void left by a lost love," Emma said as she sat down. "It's a way of grieving, a way of making sure we never get hurt again."

"Yes but it's not what I want any more," Regina said, her voice little more than a whisper. "I don't want to play it safe, Emma. I don't want to hide away from my emotions. I'm tired of feeling empty and hollow. I want to love again. I want to feel loved again. Aside from Henry, I've had far too little of that in my life and I miss it."

Emma pulled Regina into a hug. She could say it. She could let the words tumble oh so easily from her lips. But she didn't. Somehow she knew this wasn't the right time. Whether because it felt too soon, or because it seemed too cliché, she wasn't sure, but the blonde contended herself in simply holding the older woman, hoping that would convey the depths of her feelings.

"I built walls around my heart from a very young age," Emma said when they pulled back from one another. "When I had to leave my second foster family at the age of five, I realised that my life was not going to be easy. There was no point getting close to foster parents or siblings because I'd be moving on soon enough. In hindsight, I guess this attitude was one of the reasons why I moved so much but I thought I was protecting myself. When I reached fifteen and started dating, I realised I wasn't the same as the other girls. I couldn't let the boys in. I couldn't trust them. I didn't like it when they touched me. Not until Neal."

"Who's Neal?" Regina frowned, expecting Emma to say that she had realised she was gay, not bring up a boy.

"My first love," Emma said. "My first proper boyfriend, my first home."

"Oh," Regina said, surprised.

"We met on the streets," Emma said. "I was seventeen, he was nineteen, and we got into all sorts of trouble. But he was fun. He made me laugh, he was sweet to me, and when we were … together, it felt ok. At least, it felt better than it ever had before. I let my walls down. I let him in and I fell in love with him. Of course it didn't work out. He screwed me over and left me in the most vulnerable position I've ever been in. He's the reason I went to prison."

Regina's eyebrows rose. She had never asked Emma about her time inside. True, she had googled some of the details herself but even in her position, she had been unable to gain access to the sealed juvenile file so she had few details beyond the sentencing and the court dates. It hadn't bothered her though, not knowing. Not until she knew there was a man involved.

"He stole some watches," Emma continued, unaware of the way Regina's mind was now racing. "I went to pick up the bag from a locker and then he was supposed to meet me. He never showed and instead a cop appeared and arrested me. I never heard from Neal again. I don't know if it was a set-up or if he genuinely couldn't come. But he never tracked me down to the police station and I never managed to find him once I was out."

"Why did you even want to find him?" Regina asked, a slight bite in her tone. "He screwed you over, right? Why on earth would you want him in your life?"

"There were some things we needed to discuss," Emma shrugged. "Unfinished business between the two of us, if you like. But I guess it will remain just that; unfinished. I went to Tallahassee as soon as I got out because that was where we were going to head with the money from the watches. Never even heard a whisper of him being in town."

"So that's how you ended up in Florida," Regina said slowly. "I was wondering how you went from prison in Arizona to the Sunshine State."

"I was looking for Neal," Emma nodded. "But I found someone else."

Regina's gut twisted. She didn't know why but she got the feeling she wasn't going to like what Emma said next. Regina had known she was a jealous person but she hadn't expected to feel quite so strongly when hearing about the blonde's exes.

"Lily was the first and only girl I've been with," Emma said. "I suppose in theory that makes me bisexual but I never enjoyed sex with men the way I did with her." Regina visibly bristled. "Sorry," Emma said quickly. "I mean, I hate her now. But I'm not going to lie to you about how good we were together."

"I get it," Regina said quickly, her eyes slightly darker than before. "Please, go on."

Emma nodded but paused. She didn't know how much she wanted to tell Regina about Lily. She hated even thinking about her ex, let alone talking about her. This was the relationship which had sent her life into a downward spiral. A spiral which had landed her on the streets, selling her own body for money to buy food, and then finally to Regina and Henry.

"We met in Tallahassee, right after I arrived. She helped me try to find Neal and then she was there for me when we couldn't. We were together for over two years."

Emma stopped again. She didn't know how she was going to explain what happened next. After all, even she didn't understand what exactly had gone wrong.

"Emma," Regina said softly. "You don't have to talk about this if you don't want to."

Emma smiled weakly. "It's ok," she said. "It's just strange, you know? I haven't thought about Lily in a while. At least, I try not to. She broke my heart and I don't want to give her the satisfaction of still affecting me."

"Broken hearts need time to heal," Regina said. "But they do. It takes a while but eventually they mend and then they can love again."

"I'm not so worried about the loving," Emma said. "It's more trusting. I can't trust anyone, Regina. It took so long to learn to trust Lily and then she betrayed me. What if I can never trust someone again?"

Regina didn't answer. She didn't think Emma needed her to. She had already told the blonde, on more than one occasion, that she trusted Emma with her son. Did it hurt that Emma didn't trust Regina? Yes, of course. But Regina was starting to understand why that was. She was also starting to hope that in time things might change and Emma would be able to put her faith in Regina.

"I came back from work one day," Emma continued, "and she'd left. We shared an apartment in Florida and she'd just gone. Taken everything. Literally. All my stuff, all her stuff, all our stuff. She'd left a note; something about meeting another woman and falling in love. How she was sorry that she'd hurt me but she didn't want to continue our relationship because she was no longer in love with me like she used to be. And I got that. It hurt, obviously, but I got it. I didn't want to be with someone who didn't love me. But why did she clean our apartment out? She even wiped out our joint bank account. She took everything I owned in the entire world. It wasn't much, what we had, but it was ours. And then I was alone again. No money, no car, no things. I hopped on a bus to New York that night. I don't know why. I don't know what I was hoping to find here but, well, you know how the rest of my story goes."

Regina didn't know what to say. She doubted there was a correct response to what Emma had just told her. So she didn't say anything. Instead, she pulled Emma into her arms and held her as silent tears slid down her cheeks. Emma curled into the embrace, seeking comfort and reassurance from the woman whose arms were wrapped tightly around her slender body. She didn't wipe the tears away. There was no point. She wanted, no, needed, to cry.

After a long time, Emma tilted her head up towards Regina.

"Thank you," she whispered.

"For what?" Regina asked, swiping away the tear streaks with the pad of her thumb.

"For listening to me, for telling me your story too. I think it's pretty clear we've both been through some crap but maybe now our lives will start to get better."

"I hope so," Regina smiled. "I really hope so, Emma."

"And I'm sorry," the blonde added.

"For what?" Regina repeated.

"For ruining this date. It was all going so well and then I had to remind you that I might have some awful STI and then bring up Dani and then cry about how Lily fucked me over. I shouldn't have said anything. I should have just pretended everything was fine."

Regina kissed Emma softly, their lips damp from the blonde's tears.

"I don't want you to hide your feelings from me," Regina said. "I'm glad you told me. I'm honoured that you felt you could tell me those things and ask me those questions. I know you say you don't trust people but I think you're closer to doing so than you realise."

"I want to be," Emma said.

Regina kissed her again. She already knew she would never tire of kissing the thin, soft, rose-pink lips. Emma's hands threaded into her hair, pulling the brunette's mouth harder against her own and causing Regina to moan in delight at the desperate need with which Emma was now kissing her. She needed Emma too. She really did. But …

"Stop," Regina gasped.

Emma did so at once, uncertainty etched on her face as she looked up at the brunette. Regina's cheeks were flushed and her eyes almost black with arousal. Whatever had made the brunette stop the kiss, Emma was relieved to see it wasn't anything bad but she still cocked her head to one side as she waited for an explanation.

"If we keep going," she said, her breathing heavy, "I'm not going to be able to resist dragging you into my bedroom. And as you said, we need to wait a week."

"One week," Emma nodded.

"One more week."

A/N: and this is the last T rated chapter …