I do not own the characters in this story, they are owned by whomever produced or directed the tv show Once Upon a Time.

Summary: Trapped in a loveless arranged marriage to the local Mayor, Regina Mills admits something private to two of her best friends who promise to help her. Along the way, she is surprised to find not only love but strength, happiness, and a new family.

Two days later, Regina found herself pacing the floor of a hotel room, panicking. Her breathing was ragged, sweat dripped profusely down her head leaving her body and hands clammy. She knew she had to calm herself down or she will pass out and that is definitely not how she wanted this first meeting to be; with a stranger finding her unconscious on the floor.

She moved over to a decanter and glasses atop a bench in the room, the normally stoic and dignified woman poured herself two fingers of whiskey before she drained the glass of its contents and refilling. Thankfully, the drink helped to calm her palpitating heart. She inhaled and exhaled for a few minutes; Regina closed her eyes to think about her imminent future. She held fast to her decision, opened her eyes and reached down to pick up her duffel bag that sat at her feet before she walked into the in-suite.

Forty minutes later, Regina was ready and once again paced the floor. The brunette had finally worked up enough courage to continue with this travesty of a date but the escort had yet to arrive.

"Maybe this is a sign." She growled feeling deflated. "Enough is enough."

The beautiful brunette adorned her jacket, stormed towards the door with her duffel in her hand, and halted by the sudden knock on the door. "Great, just great!" She mumbled. She opened the door with every intention to dismiss the person on the other side and walk right out of this room. "I understand this is not…" Regina started before her breath caught and her words disappeared at the sight of the woman that stood in front of her.

"Hi." The blonde smiled. "I'm sorry I'm late, I had car trouble and no idea how to get in touch with you." She blushed.

Regina couldn't move, she was absolutely aghast at the sight of the blonde. Her chocolate eyes roamed the delicate features of the blonde's face, her emerald jeweled eyes that sparkled with hope, her glorious smile that highlighted her dimpled chin and her lips… thin pale lips that coughed and woke the brunette from her trance.

"Well, considering it's a death trap, dear, that's no surprise." Regina snapped.

"Oh Regina, don't talk about my baby like that, she's a classic." The woman smirked as the brunette beauty rolled her eyes in response.

"Emma, what are you doing knocking on my door? I'm waiting for someone."

"I know." The blonde replied. "I'm… um… I'm that someone." She informed Regina.

"You're what?" Regina gasped, stunned by the information. "What the hell are you doing working for an escort agency, Emma? You're the damn Sheriff of the town."

Emma laughed and infuriated the brunette more.

"What the hell is so funny?" Regina fumed; her hostile voice instantly cut off the laughter.

"Regina. May I come in so we can talk?"

"I suppose so, Miss Swan. I'm sure this is some misunderstanding." Regina replied as she stepped to the side and allowed the blonde to enter. She gestured for Emma to sit on the only seat in the room, while she stood beside the bed. "So, care to explain?" She asked.

Emma took a deep breath and exhaled slowly before she began. "Ruby didn't call the agency; she called me and explained your ah… dilemma."

"My d..d..dilemma?" Regina stuttered. How could Ruby do that to her after that episode with Mal and her girlfriend? "Why in God's name would she do that?"

"Ah…" Emma knew her next words could determine if Regina stayed or left the room, but she had to take the chance. "Because she knows that I have the biggest crush on you," Emma whispered and at the sound of a gasp in the room she lowered her eyes to the floor.

"You have a crush on me?" Regina couldn't believe her ears.

"Yes. Look, Ruby told me the reason for an escort, Regina. Please let me do this for you."

"No… I can't do this with someone I know… I can't do this with you. Ruby had no right. I'm sorry, I need to leave." Regina blurted out before she fled the room with her jacket and duffel bag, leaving a rejected Emma behind.

"How could you, Ruby?" An angry Regina demanded; she barged her way into her friend's front door of their home. Rage painted across her face as she stormed towards her shocked friend. "Why would you send her to me and tell her about me? Why? Why someone I know? Why her? I thought we were friends, sisters even. You're just as bad as Mal!" She wiped the tears that drenched her cheeks.

"Because you deserve to be loved by someone who respects and admires you, Regina. That woman likes you, for you. Not for what your mother can do for her, not for your heritage. That woman likes you, really likes you, all of you. I know Emma and I know she would cherish the time making love to you. That's why I asked her and not an escort." Ruby explained as she gently moved Regina to sit on the sofa. "I understand that you're angry at me, and shit Regina, you have every right to be. But I do love you. You are a sister to both Belle and I and we would do anything to make you happy. All we wanted to happen was for your first time with a woman and your first orgasm to be with someone who will care for you and bring you so much pleasure, all the pleasure that you deserve."

Regina's anger had quickly dissipated as Ruby explained, only to be followed by remorse as she recalled leaving Emma behind in the room, alone. "I think I might have ruined it, Ruby. I ran out of the room after she told me that she has a crush on me. If it were anyone else, I would have probably laughed, but it's her, Emma Swan and I can't do this with her." Regina exhaled slowly.

"Why? What is wrong with Emma that you're willing to let a perfect stranger touch you instead of her?" Ruby couldn't understand Regina's problem with Emma. The blonde was stunning, and her personality highly complemented Regina's. Unless…. "Do you like Emma, Regina?" She asked her friend who neither confirmed or denied, well not verbally. However, the sudden dust of red creeping up Regina's cheeks was all the confirmation Ruby needed. "Okay, well that explains everything! We just need to get you two back into that hotel room." She smiled.

Meanwhile, Emma sat alone in her bedroom disgusted with herself for thinking Regina Mills would have ever seen her as anything but the town Sheriff. She had returned home not long after Regina fled the hotel room, abandoned and rejected. It's not often that Emma opens herself up for emotional hurt, but today she felt she needed to take that risk and in return, she was rejected. She had not felt this bad since she was a young kid in foster care and it's a feeling she hates with a vengeance. She wiped at her tears with the thought that there is only one person that can help soothe this pain in her heart. So, she got herself up, undressed and clothed herself in her normal armor of blue skinny jeans, white tank top, brown knee-high leather boots, and her trusty red leather jacket. She then called her parents to inform them that they no longer need to care for her son tonight as her plans had changed and left the house to collect her son from school. She needed his arms wrapped around her.

Unfortunately, the gods still wanted to punish her for her stupidity because standing outside the school was none other than Regina Mills. "Why the fuck does shit always happen to me?" Emma screamed inside her car, she cursed herself quietly for insisting Henry stay in school until he is collected by either Emma or her parents. She exited her car and ran quickly across the road, giving Regina a wide berth in the hopes that she would be stealth enough to go unnoticed. Her gaze not lifting until she was on the school grounds.

On arrival at her son's classroom, she saw his smile shine brightly like a star in the night sky when he saw that she had arrived to collect him.

"Ma!" He called and launched himself into her open arms.

"Hi, Hen." She greeted and returned his smile.

"I thought grandma was picking me up?"

"Change of plans kid, I hope you don't mind?"

"Of course not, Ma." He smiled as he pushed to be released.

"What do you say we go home, make a fort, watch movies and order pizza for dinner?" The blonde mother asked excitedly.

"Awesome, Ma." The brunette nine-year-old squealed as they walked to the school gate. But Emma stopped when she noticed Regina standing at the gate staring at her.

"Ma, are you okay? Come on, let's go."

'Yeah kid, let's go." Emma replied. She kept her head down as they passed through the gate until the deep sultry voice she loved to hear stopped her in midstride.

"Emma, can we talk?" The brunette asked quietly; she hoped Emma would still give her the time of day.

"I'm sorry, I need to get my son home." She replied calmly before she turned to leave.

"Please, Emma. I just want to talk." Regina pleaded.

Emma frowned and returned to look at the regal woman who always made her heart pound with want for her. "I think we said all that was needed to be said, don't you think? I understood your actions quite clearly when you left."

"No, no, you don't. I was confused, please let us talk." Regina begged. She knew she hurt the blonde by leaving but she needed to explain herself.

"I'm sorry, Regina. I don't believe there is any more to be said. Have a good day." Emma turned and left without another glance towards the brunette, missing the tears that cascaded down the beautiful tan cheeks.

"Mom, are you okay? Did Henry's mom hurt you?" Regina's son Roland asked when he noticed her tears as he arrived by her side.

"No, no she didn't."

"It's okay Mommy, I won't let anyone hurt you anymore." He smiled up at her.

"Thank you, my love. I love you so much, Roland."

"I love you too, Mommy."