Castiel knew that he would not be lucky enough to arrive after everyone fell asleep, or before his brothers were three sheets to the wind. As he pulled in the drive he took a deep breath and decided that Dean could handle himself. The need to pee was pressing, and he was aware the anxiety wasn't helping.
When he put the car in park Dean jumped awake.
"We here?" he rubbed his eyes, looking the average middle class periwinkle blue home over. He smiled at Castiel "You okay, man?" Dean asked, placing a hand on Cas's shoulder.
"Probably not, but I'm trying" Castiel laughed nervously.
"I'm not worried, so you shouldn't be" giving Cas a pat on the shoulder.
He opened the door and began to unbuckle Ishmael who held out his arms to Dean sleepily.

The porch light came on, followed by a voice Castiel hadn't realized he missed as much as he did until he heard it. He and Anna had talked on the phone since the incident, but he hadn't seen her. She was beautiful as ever, looking more like Sarai since she colored her hair a light auburn, it pulled at his heart making him feel even more guilt for having pushed them all away, especially her; Anna was so much like Sarai.
Anna wrapped her arms around Castiel's neck, and he spun her around. Swimming in the sound of her joy, Castiel laughed, too.
"Oh." Anna said, looking at the man holding her nephew and petting his hair as he drooled on his coat "This must be Dean"
Castiel knew he would never hear the end of it from her. Maybe not now, but she saw the way Dean held Ishmael, and she was as gone as Cas.
Dean greeted her with a full smile, extending an arm to hug her as he held the boy. Anna rubbed Ishmael's back sweetly, and he sighed.
"How was the trip?" besides grabbing Ishmael's things out of the back, her full attention was on Dean; leading him into the house with Ishmael. The conversation faded away as Cas grabbed a few more bags out of the trunk.

Cas had met Gabriel's oldest Michael who was now 6, and Gabriel's wife (girlfriend last time Castiel had seen her) Rachel was Due in February with another son. Balthazar and Uriel had married sisters 3 months ago, and were mad enough at the time not to invite any of the family. Balthazar's wife Gennipher was pregnant also, but only just. Uriel and his wife were very obviously still in the honeymoon phase and had no interest in children. Anna's Fiancée Michael was everything that Anna deserved, and was nice enough to help Castiel with bringing the bags up to their room, and gave him the updates on the family (at Anna's request). The children were already nestled together sleeping on the floor in Michael's room, the title screen of The Lion King on repeat.
Castiel watched Dean place Ishmael into an open space in the middle. The boy remained asleep, only letting out a heavy sigh when Dean wiggled him out of his coat. Dean beamed and tip-toed out of the room, smiling at Cas.
"Hey, where are we?" Dean whispered taking off his own coat.
"We're over here, I brought your bag up" Cas hadn't really thought about the fact that the bed might be an issue, he had only ever traveled with Megra. Sure, the bed was a king, but it was still just one bed. He opened the door for Dean to walk in ahead of him, arms full of his coat and Ishmael's. The room had it's own bathroom (as it happened so did all the rooms in Gabriel's home), a walk in closet, and a television.
"Cool" Dean said hanging the coats in the closet.
Cas was reminded suddenly how urgently he now had to pee.
The bathroom wasn't large but was arranged well enough for a corner style Jacuzzi tub and a shower with glass doors. He resolved to make this his retreat if a week here with the family overwhelmed him, which it would. Unfortunately much of the family was downstairs waiting. Gennipher and Gwen had turned in early, so the siblings and Michael were left downstairs.
He opened the door, ready to face the family and put on his happy face. He was not ready for Dean Winchester sliding out of his pants wearing tight black boxer briefs that were hugging his ass. Castiel was ready to die, this was it. In that moment he was lost in an ass, and moments away from being completely mortified.
"Hey, can you hand me those pants" Dean said, sitting on the bed folding the ones he had been wearing. "the bottoms of these ones are all wet"
All Castiel could think about was why he had to take his shirt off to change his pants, why he had to sit on THE bed in nothing but his underwear. He handed the man his pants, and promptly left the room, he was sleeping on the floor.

He met Gabriel in the kitchen pouring more drinks. By the light sway he had going on, Castiel assumed he must be at least five drinks in.
"Hey, Cassy!" Gabriel drew him in for a hug "Where's your boyfriend" he was kind enough to whisper in his ear. Before Castiel could respond, Dean rounded the corner.
"There he is!" Gabriel lifted two drinks in the air, and handed one to Dean, putting his now free arm around the man "Come meet the family" he said, winking back as he lead Dean to the living room. Castiel followed, grabbing himself a drink for each hand.