Hi guys, I saw this prompt on Twitter and I really wanted to write about it! I hope you all enjoy! Oh and I do not own anything related to OUAT

Today was a big day for both mother and son; it was one they would remember for the rest of their lives, in fact, it was a part of life that no mother ever wished for. As much as Regina tried to prolong the event, Henry was finally moving out and heading to college, her baby boy was on his first steps towards full adulthood. This was the last time for a while where she would get to make him breakfast, the last time she would see him in the comfort of his home without evidence of him ever being away. She knew that this moment would come but she never expected it to happen so fast, she could have sworn that just yesterday she was changing his diaper but although it felt like it, life didn't stop for anything. She had spent the previous couple of weeks trying to prepare herself for this moment so that it wouldn't creep up on her so at least that way she could hold some of her emotions at bay but who was she kidding? This was her baby boy and he was about to lead his own independent life.

When Henry had told her that he had been looking at colleges at the beginning of the year she wasn't exactly surprised, ever since he was a young boy Henry always had a plan and she was glad that he had picked that trait up from her even if it was one of the only ones. Of course, she supported his decision one hundred percent, Regina Mills would not have her only son spending the rest of his life here in Storybrooke working as a janitor, there weren't any colleges in the town and for that she was grateful, at least Henry would be getting a decent education when he left for college. However, what surprised her was when he told her he wanted to become a writer. She knew Henry had always had an active imagination and his stories were out of this world but she always just assumed that he would follow in the footsteps of her brother and become a fireman; he had always admired Neal so it came as a shock to them when he admitted to his passion for writing. Nonetheless, Regina ensured that he received endless amounts of support and a big part of her was glad that he was trusting his instincts and doing something that he loved rather than allowing himself to be influenced by those around him.

Regina stood in front of fireplace with a small but sad smile on her face as she observed the countless photographs of Henry as he aged through the years, she couldn't believe that the floppy-haired, clumsy brown-eyed eight-year-old in the picture was about to move out of their home. The brunette was brought out of her reminiscing by a voice behind her. She hummed as she turned around to face her son, he had grown so tall over the past two years, he towered over her but she could still picture him as the short boy who struggled to steal cookies off of the dining table.

"You ready to go? I've packed my things in the car." Henry said gesturing towards the open front door with his hand.

At first he wasn't amused by the idea of Regina driving him to college on the first day but he immediately changed his mind after seeing how upset she got when he said he would go with Violet. He knew this was a big deal for his mom so, rather than going with his girlfriend, he promised Regina that it would be just like old times when they went on car trips with Emma and Killian.

"Of course, dear," she smiled softly as she headed outside towards the car.

Almost as soon as they were both buckled up, Regina turned to him with concern filling her face. "Are you sure you have everything? Perhaps we should go back inside just to be sure; I can make you some hot cocoa whilst we check."

Henry let out a chuckle as he quickly stopped his mother from unbuckling her belt, "I checked everything twice and then again after I packed them in the car." He chuckled as he feigned a defensive look, "I promise, I'm not completely incapable."

Regina shook her head lightly before letting out a chuckle of her own and starting the car, reluctantly pulling away from their home. They had a long journey ahead of them but Regina knew it would pass quickly so she figured she would make the most of her time left with the eighteen-year-old and so they spent the rest of the car ride talking about what Henry would do when he arrived or when he would come back home and, much to Regina's annoyance, Henry would often jokingly mention how much time she would have to spend with Killian when she got back home. It wasn't that she didn't like the man, in fact they got along just grand, the only downfall of their relationship is that they are far too alike and often clash due to that.

Although it was a four hour drive, the two now found themselves getting out of the car as Regina observed where Henry would be studying for the next few years whilst Henry got his things out of the car.

"So, what do you think?" He asked they began walking towards the dorms.

Regina tried not to grimace at the sight of the obvious frat boys leering and practically drooling over her as they walked through the dorms in search of Henry's but other than that, she was glad that her son had chosen this place. It seemed sophisticated enough but it was clear that the professor's knew how to have fun considering that she just witnessed one of them walking past her with a Nerf gun, boy could she only pray that Henry spent more time focussing on his degree than messing around.

"Just don't get involved with the wrong people." She said with an eye roll as she heard another wolf whistle.

Eventually, they arrived at Henry's dorm and the teenager opened the door, surprised to find it empty aside from the beds on either side of the room, the desk in front of the window and the unzipped bag laying on one of the beds. It appears as though his roommate for the semester had already arrived and had wandered off. The two Mills' stepped inside and again, Regina tried not to grimace at the sight of the small room. It wasn't that she was a snob or anything; she just didn't understand how you were supposed to get work done in such a confined area. However, Henry seemed more than content with his new living arrangements as he happily set his bag down on the floor and observed the outdoor surrounding through the window. The boy then decided that he was going to grab some coffee, telling Regina that he'd be fine to go on his own. After about a minute of her being in the room alone, she was interrupted by the sound of the door opening and closing accompanied by a tall, lean figure entering the room. Regina turned to look at who had just joined her; a clean-shaven male with sandy coloured hair and wearing a t-shirt that clung to his defined body.

Regina tried not to audibly gasp when their eyes met, she could immediately sense the attraction between them. He was perfect in every way with his deep blue eyes she could easily find herself getting lost in, it was obvious that he couldn't have been that much older than Henry considering he had the physique of a twenty-year-old and the face of an angel, she also couldn't help but notice the lust in his eyes as soon as he looked at her and she felt a pool arousal rush to where she hadn't been touched in so long. She quickly removed those thoughts from her mind when she realised that she was almost a decade older than the boy and the fact that he was going to be roommates with her son.

"Robin Locksley, it's a pleasure milady," his eyes sparkled as his small smile showed off his dimples and he stuck his hand out to her.

Regina almost swooned at his accent, it wasn't everyday she met an Englishman. She blushed as she gently took his hand and shook it lightly, "Regina Mills."

"Would I be correct in assuming that we're going to be living together for the next year?" He asked, still holding onto her hand.

Regina chuckled lightly, "I'm actually dropping my son off, he should be back any minute."

Robin bit his lip softly as he hummed, "Pity, it's not every day I have a woman as beautiful as you in my bedroom." He joked.

At first Regina's eyes widened at what she thought was him coming on to her but laughed as soon as she realised that he was kidding, he seemed like a sweet guy and she was happy that he was going to be sharing a room with Henry, maybe he would keep her son out of trouble.

Their small introduction was then interrupted by Henry returning into the room with coffee for him and Regina, smiling when he noticed someone else in the room.

"Hi, I'm Henry Mills," he said to the stranger.

Robin gave him a genuine smile in return, "Robin Locksley, I believe we're going to be roommates."

Henry's smile widened when he heard Robin's accent, "Where in England are you from?"

Regina smiled at the fact that her son had already made a new friend, a new friend who seemed like the type of guy who'd keep Henry on the right track. She watched as the two shared a conversation with each other, all her concerns about her son beginning college disappearing. Eventually, it became time for her to leave otherwise she would get caught in traffic and wouldn't arrive back home until late at night.

"Do you want me to walk you to the car?" Henry asked, hoping that she'd say no so he could spend time with his newfound friend.

"No, that's quite alright, dear," she smiled sincerely, giving him a kiss on the forehead as Robin stood up besides the door.

Regina moved away from Henry and smiled as Robin opened the door for her.

"It was a pleasure, Mr Locksley."

"I can only hope that we'll be seeing each other again soon, milady." He suggested with hope.

Regina looked down and blushed, "Perhaps." She said quietly before leaving the room and heading back to her car.

As soon as the dorm door was closed, Robin sat on the bed opposite Henry's and smiled, "You have a wonderful mother."

Henry just nodded in response, not particularly interested in talking about his mom anymore.

And with that, Robin spent the rest of his day thinking about the woman he had found standing in his dorm room, thinking about how beautiful she was whenever she blushed or how her brown eyes would darken whenever he subconsciously flexed his arms. She was positively beautiful, perhaps the most beautiful woman he had ever seen but he knew he would be playing with fire, she's his new roommate's mother for God's sake but that wouldn't deter Robin. That night he went to bed dreaming about the brunette who refused to leave his mind whilst Regina guiltily thought back to the young English gentleman she had encountered earlier that day, she kept reminding herself that he was just a boy but she could have sworn that his eyes were on her the whole time they were in that room and she slept with a smile on her face as she realised that sending Henry to college wasn't so bad after all.

Hope you guys enjoyed, this will be multi-chaptered so if you did enjoy don't worry, there will be more! Please leave a review and let me know what you guys thought! Thank you