Theodore couldn’t help thinking his step-son was adorable as he left for school on the day of Halloween. Vivian had decided that he was just going to wear the cat ears and tail with his normal outfit, going to school as a black cat, then change after school into the full outfit. Black cats were after all his favorite type of cat.

Theodore himself had decided, without telling Vivian, that he was also going to dress up as something similar. He was planning on going as a teddy bear in a tuxedo, but when he had searched through his costumes for bear cub ears and a tail, the only ears he could find though were attached to a light blue frilly headband. So Theodore had decided to roll with it and wear a baby blue dress and go as Goldilocks’ Mother Bear. Since this was his hometown, he already knew most of the teachers would be accepting of a early-thirty year old father wearing a Goldilocks costume for Halloween. The people that already knew him from his childhood would be even more comfortable with it.

One of the reasons Theodore decided on his hometown was for how open and accepting they were to all sorts of backgrounds and personalities. His parents were the same way once upon a time, until it was their own son getting up to trouble. They could only put up with so much of his issues before they disowned him and forced him to move out of their home. Coincidentally, they ended up leaving Oakhaven when they retired, leaving their navy blue house empty for several years before a certain step-father and son pair moved in.

Theodore went up the stairs that were all the way in the back of the house. They led to a room that he thought he would never return to when he had left eighteen years ago. Ann had kept everything he had owned and left behind when he couldn’t stand staying in the town and had left for various reasons after three years of independence. Now that he was back, he had moved everything he left behind to this room. He wouldn’t sleep here anymore since he had taken over the guest room on the first floor and had given Vivian the master bedroom, but it still brought many memories. He ran his fingers over the door frame of the closet where he and his friends compared heights growing up. His fingers lingered over a set of smudged initials.

Theodore was a bit nervous about going to the high school and making it officially known that he was back. There were going to be a lot of mixed feelings, but he knew he shouldn’t put it off for longer than the month they had already been there for. He had run into a few people at the library, but most didn’t recognize him since it had already been at least fifteen years and he had grown up a lot.

The person he was most nervous about had yet to run into him though. Theodore wondered if they would recognize him. Would they be shocked about Theodore returning with a teenager? Would it even matter to them anymore? Had they moved on already? Would they forgive him?

Ann had tried her best to keep Theodore up to date about all the news surrounding their group of childhood friends, but Theodore worried if she only told him what he wanted to hear…

Buckling down, Theodore tried to channel his younger years to gain the confidence he knew he needed to rebuild. He usually wasn’t one to become withdrawn and nervous like this, but it just showed how much they meant to him. Fifteen years ago Theodore had accused them of something that they didn’t do because of a misunderstanding. Out of guilt and embarrassment Theodore ran away before the misunderstanding could be cleared up, and hadn’t returned even after he found out the truth.

Theodore turned away from the markings on the door frame and turned his focus on his childhood vanity that he had set up and placed with his stagecraft accessories. It had been a gift from his grandmother when he was just starting up acting, and it was the one piece of furniture he had regretted leaving behind. It was worn down since it was already pretty much an heirloom by the time Theodore had inherited it, and it had seen Theodore through his childhood and teenage years. It was dark oak wood and had tri-fold mirrors with rose décor.

On the top Theodore had organized the various types of make-up he had acquired for the different roles he acted, and had made the corner with the vanity into his theatrical section of his childhood room. He had already set out the costume on the bench seat and the costume makeup front and center. He still had a few more hours until the open house, but he had a tendency to go overboard with making sure his costumes were perfect. Plus it had been a while since he got to dress up, and even longer since he got to show off to his childhood friends.

Theodore plucked a photo off from the upper corner of the center mirror. It was a photo from the first time Oakhaven held the Halloween Masquerade. It contained Ann, her sister Mari, Theodore, Ari, and Tristan. Ann was the only one who was still single that year, but everyone had agreed and insisted that they had to go as the five of them. They were after all the main reason the town started the annual tradition that year.

They had decided to go as characters from Alice in Wonderland since Ann was fascinated with fairy tales even back then. Ann went as Alice, Theodore as the White Rabbit, Ari was the Cheshire Cat, and Mari and Tristan went as the Queen and King of Hearts. They were happy back then, locked in the naive joys of youth. It was taken the same year that his parents would disown him. In fact it was later that week that he would move out of the room that he had finally returned to after so many years.

Theodore smiled as he remembered moving into the first floor of Ari’s house that was originally two upper and lower apartments before Ari’s parents bought the building. The others had decided to also partially move in to help support him with his sudden abandonment, and were constantly coming and going from their own parents’ houses to become his new family.

Ari’s parents had become everyone’s second set of parents, and Theodore was devastated when he had heard of the car accident ten years ago. He had even ended up dragged Vivian along when he had secretly returned for the funeral, his mother being too busy as mayor to watch her five year old by herself for even a weekend. He had wished to give his condolences, but he had only let Ann know he was coming and had felt too embarrassed to talk to anyone. He had ended up just standing in the back corner in discrete clothing holding a toddler, and then staying with Ann since it was such a long way away from Eastedge.

Theodore put the photo back before stripped down to his boxers. He then slipped on the petticoat and front facing corset to give himself more of a feminine appearance. He had always insisted that he could never go too far on small details. Especially when there was a costume contest going on. Once the undergarments were all in place he started on the outerwear. He wore a white blouse with a quarter sleeve, and then slipped on a solid baby blue jumperskirt style dress on top. To add to the sweet lolita look he adjusted and pulled back the front part of his medium length blonde hair with a giant floppy blue bow pinned in the back. He had already pinned the tail to the dress’ waistband before putting it on, so all that was left was makeup and props.

Right as Theodore was finishing up the final touches he heard the doorbell. Looking at the time he realized it had to be Ann since they had agreed to carpool. Grabbing a pair of black Mary-Jane's from a large shoe rack and two blue ribbons, Theodore quickly hurried downstairs and opened the door for her.

“Wow. You have definitely aged well Theo, for you to still be able to pull off female outfits…” Ann just stood in the doorway as Theo stood before her in a full out female costume.

Theo looked Ann up and down as well. “I can say the same to you Ann. Which fairy tale Woodsman are you portraying this time?”

“The one from Red Riding Hood won this year.” Ann smiled brightly through her fake ginger beard. “Are you ready to go yet?”

“Almost, I wanted to tie some bows on my shoes and then I’m ready.” Theodore let Ann come in as he sat down at the island and started to tie the ribbons he had grabbed onto the black shoes.

Ann obliged and came in, sitting down next to him to wait. After a minute she asked him what was obviously on her mind. “How are you feeling? Are you really ready to officially be back at Oakhaven?”

Theodore took a moment before responding. “I’m probably not, but I can’t keep putting it off any longer. I have been convincing everyone that has recognized me to stay quiet for a little longer, but I can’t rely on everyone not to tell. I want to be the one to inform them of my return myself.” They both knew who exactly he was implying about informing. Taking a deep breath, Theodore slipped on his shoes and stood up. “It’s now or never. Let’s go.”

Ann drove Theo to the school and the two of them met Vivian and Philip by the flagpole outside the doors. Neither of the two teenagers were overly shocked at the costumes since they both knew how fairy tale oriented their individual guardians could be. Theodore quickly introduced Ann as Philip’s aunt since he still hadn’t told Vivian that this was his hometown. Vivian knew that Ann had offered to help his step-father carpool since she lived just down the road, and politely greeted and thanked her.

After the greeting was completed the four of them decided to wander around the school together to visit each of the students’ classrooms so the guardians could learn how their charges were doing in school and what projects they were working on. There were also different club displays littered throughout the halls and non-specific classrooms.

Theodore really didn’t know how to feel coming back to his Alma mater. Nothing had really truly changed overall. It was the same building with a new batch of high schoolers. When he met Ann’s eyes he knew that she could see what was going on in his head. She didn’t say anything though because she knew Vivian still didn’t know. This night Vivian would be finding out about his step-father’s past one way or another.

Philip had insisted that they started at the drama club display outside of the music room and had started to hurry ahead, dragging Vivian with him, as the adults lagged behind slightly. Ann immediately saw what her nephew was doing and had leaned over to Theo. “Are you going to be OK? I can tell that you are going through an emotional roller coaster right now, and even my thick-skulled nephew noticed and pulled your step-son away. Do you want a time out?”

“N-no… I’m fine. It’s just been so long since I left…” Theodore started to take deep breaths as they walked and slowly caught up to the teenagers.

“I’m pretty sure you will like Mr. Lawson, Theo.” Vivian turned to his step-dad with all seriousness. “He kind of reminds me of you at times, somehow.”

Theodore didn’t have time to respond since they had already arrived by the music room and the teenagers had already started stepping through the doorway. Theo felt a small push from behind from Ann along with a quietly whispered encouragement. Taking a deep breath yet again, he stepped through the door after Vivian and Philip.

“Hey Ari! It’s been a while!” Theo’s voice cracked slightly at the sight of Aristotle’s back, that he had memorized years ago, as Ari was still writing on the whiteboard.

At the sound of Theo’s voice Aristotle Lawson whipped around. “Teddy?!”