The rest of the afternoon was filled with Henry's laughter and small conversations amongst everyone else. After a while Henry crawled into Dean's lap and snuggled up against his chest.
"Is someone sleepy?" Dean asked while brushing Henry's hair back.
"Nuh." Henry huffed and pushed Dean's hand away.
"I think you are." Dean chuckled. "Do you want to go home?"
"No."
"Do you want to come sit on grandma's lap?" Mary asked. Henry turned his head to look over at Mary.
"No."
Everyone laughed at Henry's stubbornness but left him be and he eventually drifted off, clutching Dean's shirt in his fist.
"I can go set up the pack 'n play if you want." Ellen offered.
"Nah, we're alright thanks though." Dean said adjusting his son just a little. About an hour later Dean carefully transferred his son to Mary's lap. "We're going to start packing up our stuff and get home."
After a quick supper Dean bathed a sleepy toddler which was way more work than he was intending to have to do. Once he was wrapped in his towel he gave him a kiss, told him goodnight and passed him over to Cas.
When Cas came into the bedroom almost an hour later Dean raised an eyebrow. "What took you so long?"
"He fought sleep. I had to read him two stories and look under the bed and in the closet for monsters." Cas explained.
"I wonder if he's nervous for school tomorrow." Dean said almost sadly.
"Could be possible. I just hate that I can't be here in the morning to see him off." Cas sighed and crawled into bed.
"Well, just make sure you're there for kindergarten… Preschool isn't as important." Dean said cuddling up to Cas' side and turned on the tv, making sure the volume was low enough not to wake Henry.
After taking extensive amounts of pictures of Henry's first day, Henry was getting antsy.
"Come on Daddy!" He yelled from the front door, all ready for school.
"I don't know buddy. Maybe we should keep you home until next year." Dean teased while he put his camera away and grabbed his keys.
"NOOO!"
"Alright, alright I'm coming, go ahead and get in your carseat." Dean told him as he shut the lights off and locked up the house. The closer to the school they got, the quieter Henry got. Noticing his son's usual quietness Dean peaked back at him.
"Hey. You okay buddy?" He asked.
"I don wanna go daddy." Henry whined.
"What? You were so excited earlier." Dean said pulling into a parking space. Dean got the back door open and started to unbuckled Henry when Henry started crying.
"No! Daddy I don wanna!" Henry tried hitting Dean's hands away.
"No hitting." Dean warned but continued to unbuckle the 3 year old. Henry refused to move which resulted in Dean picking him up and carrying him inside.
"NOOOOOOOO!" Henry screamed. Dean's face was burning hot of embarrassment, just like at the hospital with Henry's checkup.
"Henry stop it." Dean huffed while he set Henry down. "Look at me."
Henry continued to sniffle but looked up at his daddy who had knelt in front of him. Dean wiped away the tears and spoke softly while signing, "I know this is scary but you need to be a big boy. Some of your friends from daycare are here and I know you'll have fun playing with them all day. If I get a good report from your teacher, we'll get ice cream after school okay?"
Henry nodded and wrapped his arms around Dean's neck. Holding back his own emotions, Dean carefully pulled Henry away. "Alright, here's your book bag, don't loose it and be a good boy for me." Dean glanced up and saw one of the teachers smiling softly at him. Dean turned Henry around and gave him a gentle push towards the teacher.
Once she had his hand Henry looked back and waved. "Bye daddy."
"Bye buddy." Dean smiled and waved back, staying knelt on the floor until the door closed, letting out a shaky sigh, Dean got up and headed to the impala.
Once inside the safety of his car Dean let the tears flow. He just couldn't believe his baby was starting school already. What was he going to half of the day? The "3 year old" preschool only went from 9-12:30 on Monday's and Wednesdays and 9-1 on Fridays.
Dean took a couple of deep breaths and wiped his face off before heading home. He still needed to look for a job and he was also waiting on the lawyer he and Cas hired for his lawsuit to get back to him about a court date.
Mary was waiting for him on the front steps when he pulled into his driveway. She took one look at Dean's face and pulled him into a hug.
"Oh sweetie. It'll get easier, I promise." She said softly while rubbing his back. Dean let a few more tears flow before pulling out of the hug.
He cleared his throat and asked what Mary was doing here.
"Well, I have a few hours before I go into work so I figured I'd come see how you were." she smiled softly.
"I'm okay." Dean said while opening the front door. He tossed his keys on the small table near the door and kicked his shoes off, Mary following suit. They made their way to the living room and Dean quickly picked up a few things that were scattered around the room.
Mary let out a chuckle, "no need to clean up for me."
"I know it's just I've been behind on a few things around the house." Dean confessed. "I've just been so stressed about trying to find a job and this lawsuit."
Mary sat there and listened to her son. "Honey, you need to try and not stress too much since you're pregnant. I can take some time off and watch Henry for a few days so you can catch up on some things if you'd like."
"No, it's fine mom." Dean sighed, "he's my responsibility… I mean you didn't force me to get pregnant at 16."
"No, but I didn't force you to keep him either." Mary said and grabbed his hand. "Just because you had him at a young age doesn't mean you can run yourself thin. I'm sure with Cas gone most of the time things have been extra harder on you. You just need to remember that you have a family that loves you and will help you anytime you ask."
Dean couldn't look up from his and Mary's hands while she spoke. When he didn't say anything for a while Mary continued. "I'm going to take a week off at the beginning of next month, I have plenty of vacation time I need to use. I'll take Henry for the week and you are going to catch up on sleep, house chores and anything else you need to do."
"Mom-" Dean started, but Mary interrupted him.
"Don't mom me. It's happening, just deal with it." She said and pulled Dean to her side wrapping her arm around him while he rested his head on her shoulder.
"Thank you." he whispered.
Dean and Henry were sitting in a small Ice cream shop after he had picked him up from school when his phone rang. "Hey babe, what's up?" Dean answered after seeing it was Cas.
"Hey, just on break thought I'd give you a call and see how Henry's day went."
"The teacher said he did pretty good, we're at Mo's dinner having ice cream."
"Oh, that's nice. But hey, the real reason I wanted to call was to tell you I have a surprise for you and I'll take care of dinner tonight."
"Oooo I want mexican. And what's the surprise?" Dean asked.
"Alright, and I'm not telling. You'll see tonight, I gotta go, I love you."
"Love you too. Be safe." Dean said and hung up.
"Was that papa?" Henry asked, chocolate syrup and ice cream smeared all over his face.
"Yes it was, and how did you end up with more ice cream on your face than in your mouth?" He asked and started wiping down Henry.
He giggled, "I dunno."
Not knowing what the surprise was, Dean got busy cleaning the house once Henry was down for a small nap. He had gotten a text from Cas wanting to know what he wanted from the Mexican restaurant and he still wouldn't budge on what the surprise was.
He had just finished cleaning when he heard Henry's voice upstairs. "Daddy?"
"I'll be right there buddy!" He called back. Upstairs Henry was sitting up in his bed rubbing his eyes. "Hey, did you have a nice nap?"
Henry nodded, "can we swims?"
"Not today. We can tomorrow if the weather's nice." Dean told him and scooped the toddler up, "do you need to go potty?" Henry nodded so Dean made a detour to the bathroom before going downstairs.
Once they were at the bottom of the steps Dean set Henry down, who went straight for his toys. "Hey, don't make a huge mess!" Dean told him.
It was just about 6 when Charlie came in. "Special delivery!"
"Aunt Charwie!" Henry yelled and ran towards her.
"Hey buddy!" Charlie grinned and ruffled his hair.
"What's up and why do you have my food?" Dean asked after giving her a side hug.
"Cas had me pick it up, I'm joining you guys for supper." Charlie explained.
"Oh, wait are you my surprise?" Dean asked helping her with the bags.
"Nope." She grinned.
"Ugh. How much do we owe you?" Dean asked.
"Nothing Cas venmoed me." Charlie said pulling out the container of salsa and a bag of chips. Once Henry was strapped into his chair Dean gave him a few chips and a little bit of salsa while he and Charlie divided up the rest of the food. A few minutes later they heard the front door open, "Dean, close your eyes!" Cas yelled.
"Why?" Dean yelled back.
"Just do it!"
"Alright, fine they're closed!" Dean yelled, "Cas I swear if this surprise is a dog I'm gonna punch you."
"Ah come on now Cher, is that anyway to treat an old friend?"
Dean gasped and his eyes flew open, "Benny?!"
"The one and only." Benny grinned.
"Holy shit! What are you doing back?!" Dean asked running over to give his old friend a hug.
"I moved back, I work with Cas now." Benny grinned.
"You're a cop? What happened to wanting to be a chef?"
"Eh, some things change." Benny shrugged. "Now, let's eat. I'm starving."
