The smutty good times in this chapter were a little awkward to write. Spoiler alert: when you write Destiel fanfics so much that straight fanfics seem awkward, maybe you're in too deep in your fandom? Never! :D
"Come on, Anna, is this really necessary?" Dean asked, batting away Anna's hand as she tried to apply makeup to his face.
"Yes!" Anna said excitedly. "I haven't had any girl friends in ages, I'm enjoying this. Besides, it will give you some appreciation of how hard girls have it."
Dean looked at Anna's face, alight with excitement and enthusiasm. She had saved his life, after all, and given up her grace to be with his brother. No one knew it was him under here anyway, so what did it hurt?
"Alright, just hurry," Dean said, settling back into the seat with good patience.
He was already dressed in a cute dress, though God knows he would stab anyone who dared suggest he'd thought it was nice at all. Anna dabbed the concealer onto his face, and Dean almost winced at the goopy feeling.
"So, how do you like it so far? I mean, being a girl and all," Anna asked.
"It's…well, it's uncomfortable as hell, now that you mention it. I just want my guy parts back. This having to sit down and pee thing gets old fast."
Anna giggled, moving on to Dean's eye makeup, which stung and caused his eyes to water briefly.
"Yeah, Sam isn't too happy about that either. But at least you two are hot. Maybe it's 'cause you were good looking men already?" Anna asked.
"Thanks…listen, Anna, do you mind that Sam is a girl?" Dean asked.
"Why would I mind?" Anna answered, confused, finally finishing with the makeup and moving onto hair.
"You like Sam as a man, not a woman," Dean said.
Anna's hands stilled for a moment before a small smile crossed her lips and she continued her work.
"Cas still loves you, Dean," she said, pinning part of the waves up.
"Dammit! Why does everyone always think I'm talking about him?" Dean asked.
"Because you are. Look, you never liked men before Cas, right? Nothing but women?" Anna asked.
"Yeah, so?" Dean said.
"So, why did you fall in love with Cas?"
"Because it's Cas," Dean answered.
"Exactly," Anna said, finishing Dean's hair. "And you would love him no matter what vessel he took. The same goes for you. I have never understood why humans get so worked up over sexual preference. It's not like you fall in love with a body. You fall in love with the soul inhabiting it. Now get up. We need to go eat before I gnaw my own arm off."
She slapped Dean on the back, and he stood, catching a glimpse of himself in the mirror. He most certainly did not think he looked gorgeous, no sir. Not even a bit…and he certainly didn't turn to check out how his butt looked in that dress, either. He jumped when Anna stuck her head back in the bathroom, and turned red in the face.
"You're a soul, Dean, not a body. Let's go."
They made their way to the other motel room, and Dean was surprised at the look on Cas' face when he saw him all dressed up. He walked across the room and took Dean's hand in his, and gave it a small squeeze.
"Sam! Let's go!" Dean yelled, and Sam appeared from the bathroom.
Anna's mouth fell open slightly as Sam came to join them.
"Alright, dinner. We driving?" Sam asked, motioning at his feet. "Heels are just as bad as Dean said."
They clambered into the car to drive the block to the restaurant, and were seated at a booth in the pleasantly lit room within a few minutes of arrival. They all ordered basically the same thing, and soon found themselves talking like regular, normal people for once.
"He jumped off the roof of Dad's shed, and he broke his arm," Dean said, a wicked glint in his eye as he talked about being a kid with his brother.
"Yeah, well, I was a superhero, wasn't I?" Sam answered.
"Even I know that Batman couldn't fly, Sam," Anna laughed.
"I drove him to the emergency room on my handlebars," Dean said, taking a large bite of spaghetti. "Dad was furious. We had to stay at Bobby's that week instead of going on the hunt for the ghost, remember?"
"Ugh, Dean, swallow before you talk. Yeah, I remember. That was the week Bobby taught you to change the oil in his old Ford, wasn't it?" Sam answered.
"Sure was. And you almost cried because he wouldn't let you do it with one arm," Dean teased.
"I could've done it, I swear. Bobby was just too protective," Sam said.
"Yeah, he was. Still is, too…"
Anna stifled a yawn behind her hand, and Sam noticed. He glanced at the time on his phone.
"It's getting late. We should really get back to the motel," he said, and the others agreed.
Sam flagged down the waiter to get their check. He quickly paid and left a tip, and everyone headed back to the motel. When they arrived, Anna said goodnight immediately and headed toward her room. Sam soon followed, though he took his shoes off before walking back, rubbing at his sore toes.
Dean and Cas closed the door to their own room behind them, and Dean noticed Cas had his head tilted at him.
"Everything okay?" Dean asked.
"You look lovely, Dean," Cas said, and Dean's face went red.
"No offense, dude, but that's not making the situation any less awkward," Dean said, looking at the floor.
"You have no reason to feel strange. I have taken multiple vessels before Jimmy in my thousands of years on Earth. Some male, some female. The anatomy is of little importance. To me, you are still Dean, and you are still perfect."
Cas cupped Dean's face in his hand and brought his lips up to meet his own. He pulled Dean into him, feeling the warmth of his body, and Dean parted his lips to allow for a deeper kiss. Cas delved inside, tongue sweeping every part he could reach, hands grazing up Dean's arms, and Dean felt a new sensation.
"Hmm," he said, pulling back. "So that's what it's like for girls. Not exactly comfortable," Dean said.
"Arousal?" Cas asked, and Dean grimaced.
"You can make any word sound technical, you know that?" Dean said, but he smiled and pushed Cas backward toward the bed. "Want to see how this works?"
"I'm perfectly aware how sexual intercourse works. I've seen movies."
Dean rolled his eyes at the angel's lack of understanding of rhetorical questions. He climbed on top of Cas, who reached up and unzipped the green dress. Cas lifted it off and it fell to the floor. That started a chain reaction, and soon both Cas and Dean were naked, kissing and grinding on one another on the bed.
Cas suddenly flipped them over, and was on top of Dean in an instant. He kissed at Dean's neck, down his collarbone, and left lovebites all over. Dean groaned, wanting more. His hips thrust upward, and Cas kissed him deeply.
"You ready?" Cas whispered in his deep voice, and Dean nodded feverishly.
Cas pushed against Dean's entrance and easily slid in. The sensation was unlike anything Dean had ever experienced. He was full of Cas, surrounded by him. Cas started to move, thrusting deep inside. When he would push flush against Dean, little tremors would go off as he touched something sensitive. Dean hadn't experienced it before, but he knew he enjoyed it. Dean picked up the pace to match Cas' thrusts.
"Ah, Cas baby…don't stop," Dean moaned, clamping his legs around Cas' middle and scratching his nails down his back.
Cas sped up, and Dean began to feel a pulling tingle in between his legs. Cas grunted above him, slamming into him with more force than before, and Dean felt himself come close to the edge.
"Dean-," Cas grunted out, almost there as well.
The sound of his name falling from Cas' lips caused Dean to shiver, and his orgasm shot through his body like fire. His insides clenched and convulsed, and the motions caused Cas to come too, spilling inside of Dean with a gasp. He stilled, though Dean was still frantically moving, riding out the last of his orgasm. Cas finally pulled out and collapsed next to Dean on the bed, both of them breathing heavily.
"Okay," Dean said between panting breaths. "Women definitely get the better orgasm. I swear that was three times as long as my normal ones."
"So you'd prefer to stay a woman?" Cas asked, stroking Dean's hand lightly.
"Not a freaking chance. Let's take a shower, then I'm going to bed. Maybe we can find out some more about this mystery monster tomorrow."
The pair showered quickly and climbed back into bed, snuggling up close under the blankets and turning all the lights out. It was peaceful, just the two of them in the dark, huddled together with skin against skin. Dean slowly fell asleep listening to the steady beat of Cas' heart, and the even breathing as his angel on Earth fell into a deep sleep.