Dean/a&Caleb

24 – He likes you

Caleb Bailey looked up when the blondes walked in. His buddy nudged him and he nodded. The younger one was barely legal and the older one had a scar across her face. They both had bodies he would bang but it was too early in the evening. He needed more whiskey after what he'd seen on this last hunt. Fucking Rawheads.

Four beers and seven shots later, he was grinning at the young blonde who was trying to get a look at him around her mother. Looked like she was gonna make a get away when the older blonde greeted a dark-haired man who'd walked in shaking off the cold. She made it halfway across the room when a tall blonde man intercepted her and returned her to her mother.

Caleb gave up and his buddy ribbed him before settling up and heading out. Caleb had one more shot and one more beer. Jeff only liked hunts. He wasn't much into bonding. Caleb was just lonely mostly but he might have gotten too drunk to hook up. With the nightmares behind his eyes, tonight would have turned out badly. Night terrors and motels were a revolving door in Caleb's life. He hated when the two intersected with his attempts at normalcy.

Just as he was settling up, the blonde man came to settle up for the foursome in the back room. He looked Caleb over. Caleb returned the gaze. That was a pretty man. Blonde, green-eyed and muscles in the right enough places as not to be to intimidating. Wrong bar, Caleb told himself and waited for the declaration. If there was a universal thing in the planet, it was a big brother with something to say. "She's 19. Leave her alone."

"Hey. I've been right here on this stool. Ain't said word one to her all night." Caleb took his change and left a tip before getting his jacket on. The bar spun and he shut his eyes for a second.

The blonde man furrowed his brow and nodded as he collected his change. "Good."

Three days later, Caleb was in a different bar with different expectations and a familiar face appeared. Caleb waved the startled fellow over. "Caleb Bailey."

"Dean Winchester."

He waved his hand around. "First time in this bar?"

"Um… sure."

"It's a gay bar. For bikers." Caleb motioned around again at the leather and smoke.

"Right." Dean nodded and gestured to the door. "I should leave."

"You looked uncomfortable. I just gave you some information. Doesn't change your purpose for coming into the bar. I'm here for a drink. If I feel like a hook up with a man, I can have it. If I don't. I don't. Ain't no one here going to bother either of us unless we want them, too."

"You're pretty drunk already."

"I am. Join me." Caleb gestured around. "I will keep the gay men at bay."

"Okay." Dean ordered a beer and sat down.

The conversation was okay. Caleb was drunk. That had been his entire focus anyway. Dean helped him get thoroughly tanked. Caleb ended up dropping the kid off at his house. The lights were burning.

Caleb should have left at sun-up but he stayed in town. Bought the room for the week. On a whim, he went to the same bar that night. And the next. Then the next. Dean showed up every night. They shot the shit and got fucked up. Took turns dropping each other off. They looked over Dean's gun collection in the parking lot. That got them on hunting. Then Hunting. Once, Dean came to his room for more booze and more gun talk.

Then it'd been a month of companionship, chats, beer, scoping women… Dean letting Caleb scope men. Caleb liked that kid and he didn't know why. The walls on that one were sky high. Once, maybe, he thought he caught Dean looking but if anything, that kid was good at playing it cool. That was a game Caleb was a master at.

Then came the night that a biker got the drunken nerve to hit on Dean. Dean brushed the guy off. Guess the guy had been crushing hard and thought Dean had been giving off signals. Took a couple of his friends and Caleb to bust up the scuffle. Dean ran hot for a while, pacing the parking lot and muttering to himself. Caleb picked up some booze and they went for a ride to cool the kid's head. Dean sat with his head out the window for 20 miles around town. There was a moment, when Dean picked his head up to get Caleb's attention, that Caleb thought the kid might be on the precipice of… something but then his nose started bleeding and they had to pull over to get first aid supplies.

Sometime, after midnight, Dean made his move while reaching for the bottle they were passing back and forth on a park bench. The kid could kiss. He started to freak out a bit. Caleb yanked him back onto the bench and passed him the bottle again. Dean killed the bottle and they had to get out of there before the cops did their sweep. Caleb ended up sitting on Dean's couch with a cup of black while they shot the shit with his dad, who was up planning a hunt.

"You are two sorry looking young men." John told them as he put another pot on. "No one got laid but you two are smashed. We got a hunt in two days, Dean."

"Yeah, I know. I just didn't want to drink where Sammy was scamming." Dean lied to his cup of coffee.

"She's a big girl, Dean." John shook his head. "Your mother is watching out for her."

"I know."

"He's got a point about being worried." Caleb cut in. "She was making eyes at me not so long ago. I ain't exactly Prince Charming."

"Jesus Christ." John set his cup down and took a seat in an armchair. "How old are you, 30?"

"28."

"Fuck." John took a deep breath. "I'll talk to your mother, tomorrow."

"What are you all hunting?"

"Rawhead. Maybe two of 'em." John scratched at the back of his head. His eyes on his offspring on the couch.

"I got one last month. Thought maybe there was another. Lost its trail." He motioned to Dean. "Once we figured out the other was hunting…"

"We're on it." John nodded. "We'll get him by the end of the week." He eyed the two of them. "How did the two of you manage not to pick up any girls tonight?"

"Gay bar." Dean shrugged. "I don't know. Didn't know what it was when I started going there but…"

"But you did?" John motioned to Caleb.

"I sometimes pick up some male tail. Wasn't in the mood for either, tonight." Caleb shrugged and took a deep drink of his coffee. It wasn't really helping.

"We told stories all night." Dean lowered his eyes into his cup.

"Come with me." John stood up and grabbed Dean by the neck and pulled him into the kitchen. Caleb watched an intense discussion happen quietly before Dean swung at his father, missed, then ran out the back door. John stood there breathing heavily where he'd landed himself against the kitchen counter in his efforts to dodge Dean's fist. John poured himself more coffee and brought the pot over to refill Caleb's cup. "That's not what that looked like."

"So, you weren't warning him to stay away from the bisexual hunter?"

"Not for the reasons you're thinking." John sighed and took his seat once more. "Dean likes you. He's… gotta. He doesn't bring anyone home. Not civilians. Not hunters. Not girls. Not boys. No one."

"He seems like a bright kid."

"He's 23 and he's only been a man for six years." John admitted. "God gave me two beautiful girls. When she was 17, she went home with the wrong man. I still don't have all the details. She come home… wasted, beat up… just… I was ready to go out and find the son of a bitch who did that to her and put him in an early grave. She was in so much pain. We had to soundproof her room so the cops didn't come around. We tried all sorts of doctors. It took two weeks before we figured out what was happening. Took a full month to transition. Then I got myself a son."

"That's awful." Caleb glanced toward the door. "Why did you tell me that story?"

"Cause I saw him watching you. He wasn't going to tell you. He was gonna drive himself crazy trying to be your friend… I love my kid… He's… decided that he's into girls and he puts them off because they can all see that he's not into women. He's desperate. Smiles too big, comes on too strong… I knew it was never going to work… it was too easy." John took a breath. "He don't bring anyone home. He don't usually notice when Sammy's got her eye on some troublemaker. Means he was watching you watch her."

"I still don't…"

"He doesn't have a clue what he's doing. Not sure he's a virgin but I'm not sure anything's gone all that well. I mean… I had… It's probably different when your kid is three and you teach them to pee standing up. He was 17. It's only half a thing you just figure out. You know your old man showed you. Mine showed me. I'm sure it skeeved him right out. It took me… three or four months to realize he needed to be taught. I've watched him hit on women and just… crash and burn. I've seen him befriend men who… just aren't that comfortable around him because he can't control his own intensity. You seem pretty comfortable… I want my kid to be happy. I hate that I have to worry that my 23 year old son… my son… he's not going to make it… I need you to go easy on him. I need you to understand what the risk is… He's tried killing himself a few times and it kills his mother every time. I know I can tell you all this… because he brought you home. He trusts you."

"Honey?" The tall blonde came out of the hallway with her hands in her hair. The scar on her face covered in some sort of cream. "Is Dean in the backyard?"

"I hope so." John answered. "This is Caleb. Dean's new friend."

"Oh." She straightened and wiped at her eyes, smearing cream and making her wipe her hands on her shirt. "Mary. Good to meet you. I'll go talk to him, hon. He's stomping again."

"He needs it." John nodded.

It was quiet awhile. Caleb's buzz was gone. This Dean kid was nice looking. Could kiss, even if he'd been out of practice. Could even see that maybe he'd been a girl once. Then he wrapped that around in his mind. "Spell? Blood magic?"

"Far as we could figure. One way deal." John waved his hand in the air and shut his eyes. "We ran through it all. He was a wreck for a long time and we… well. Hunting is what my wife's family does and we dove in and it seemed to calm him. I got so good at it, my father-in-law actually seems to like me these days."

"My folks wished I'd quit it, I think."

"Truth be told… didn't want it. Deanna went chasing it after a friend of hers went missing when she was 10. Didn't let it go. Her mother said it was in her blood. Maybe she's right." John shrugged. "Maybe it's the hunting that got her cursed… but it's the hunting that's saved her life… maybe mine, too."

"Dad said it's like that sometimes." Caleb nodded. "Dad's been gone since I was a teenager. Werewolf got him. Mom was gone long before that."

"Dad!" The door burst open and the blonde's eyes went wide.

"It's damn near dawn. Where in the hell have you been?" John roared.

"I…"

"Go to your room." John didn't even leave his chair. The girl skittered off down the hallway. "That one… she was 13 when Deanna became Dean… Brains in her like I've never seen in anyone. It's baffling. I've known her her whole life and it's like all her brains fell out when her tits come in."

"John!" Mary chided when she slipped back into the house.

"She's your daughter and she just got home." John pointed to the hallway with his coffee cup.

"Dean's coming back in. You're an embarrassment, honey." She kissed his head, leaving a smear of cream in his hair, and stalked down the hallway to throw open her daughter's bedroom door. "Samantha Winchester."

"Never have girls." John tipped his cup back.

Dean walked back into the house. "I'm going to bed… I'll take you to your car in a few hours."

"Go on. Dean's got room enough for the both of you to crash where the light ain't gonna burn your eyes." John nodded toward the basement door where Dean was headed.

"You got some nerve." Caleb told the man quietly as he got up to follow Dean down the stairs. Sleep was all that happened next. Some time the next afternoon, Caleb woke as Dean was finishing his shower in a makeshift stall in the corner. "You got a shower in your basement?"

"Dad said it would help… keep the stink down if I wasn't gonna leave my room. And I didn't for like six months when I was 17." Dean tried to laugh it off.

Caleb eyed the open toiletry. "He did a nice job of it."

"It suits." Dean shrugged and wrapped a towel around his waist. "I can take you out to your car… Mom wants you to stay for lunch."

"Y'all got that whole… hunting family thing down."

"Mom was raised in it that way." Dean shrugged. "Surprised she ain't tried to come down here and fix this up so I can move in a girlfriend."

"Or a boyfriend?"

"I…"

"It's okay. It's weird the first time you do it. After that… it's okay."

"I'm not…"

"But it's okay if you are."

"Can we not talk about this while I'm naked?"

"Might be easier if you are."

That was the last said for a long while. It didn't go far but Caleb finally got a real smile out of Dean. Got him to laugh. Caleb leaned against the wall, shoulder to shoulder with Dean, still in that damned towel. "So… I know this girl."

"We're talking about girls, now?" Dean's face was red and his eyes downcast.

"Let me finish."

"Go on."

"She's my back up piece."

"How's that?"

"Let's say I'm out. I don't like what I see, male or female… and I ain't got none in a while… she's a sure thing. Pretty. A little crazy… that's the good part." Caleb cleared his throat. "She likes to play. I know you… aren't… sure… what you're doing. She'd take care of you."

"I… um…"

"She'll… share."

"Share…"

"She's… cool with a lot. A lot, a lot. I mean, we wouldn't have to tell her about… you but, she'd be cool… teaching… experimenting… with us." He could see Dean thinking it over. "Sometimes… she's already got someone, I join… or she requests a gender and I bring."

"I don't know."

"Keep it in mind. I like you but you don't gotta like me back."

"I like you." Dean cleared his throat. "My dad put you up to this?"

"He just… pulled back the curtains. He worries about you and I think… he wants to make sure I'm not gonna hurt you. I'll try not to."

"You know he's gonna think we've been down here screwing."

"Doesn't matter. People are gonna think what they're gonna think." Caleb got up and Dean found his pants. They got upstairs for a couple of brisket sandwiches that Mary was churning out. Sammy was sitting on the counter, eyeing Caleb. John whapped her with his newspaper and sat down to eat. Mary brushed her hair out of her face, moved the machetes off the extra chair and joined them.

"How come Dean gets to have sleepovers with boys?" Sammy asked, her mouth full of carrots.

"Dean's friends help with hunts, do yours?" Mary looked at her daughter. "And get your eyes off, he's too old for you."

"You coming with on this Rawhead tomorrow night?" Dean asked Caleb to emphasize the point to his sister.

"Yeah, yeah. I gotta swing back by the room for the stuff I had for the last one." Caleb nodded. "This is amazing brisket."

"Thanks, kid." John belched. "Mary's mom gave me the recipe. Mary's useless with a barbecue unless it's a funeral pyre for a monster."

"I love you, too, honey." Mary glared at him. "He can't cook anything else but my mother's brisket."

"Hey. I can absolutely do my mother's apple pie justice."

"No, you can't." The Winchester children muttered together. Mary laughed. Caleb grinned.

"Maybe, I can't." John shrugged and kissed his wife.

"Hey… uh… Caleb's gonna help with the Rawhead… but he's got this campsite he knows pretty well. I wanted to see if I could um… practice my tracking out there." Dean rubbed his hands together and kept his eyes on items on the table without making eye contact.

"You got tracking skills, Caleb?" John looked to Caleb.

"I got a friend. She's an expert. Figured I'd hook them up." Caleb ignored Sammy's giggle. So did everyone but Dean, whose eyes turned murderous when he lifted them to his little sister.

"Sounds wonderful." Mary responded. "I'll get you guys set up for the week. Three of you, then?"

"Mom." Dean groaned.

"Say "thank you," Dean." John growled.

"Thanks, Mom." Dean sighed.

"I'll get spoiled, honestly." Caleb admitted as he polished off his first sandwich. "I haven't had a decent home cooked meal since my dad passed."

"He's polite. Why aren't your friends polite?" Mary looked to her daughter.

"Wow. Dean's got a friend. Let's throw a fucking parade." Sammy made faces at her lunch.

"Watch your fucking mouth. We've got company." John took a deep breath. "You owe me seven miles for that stunt you pulled last night."

"If it was Dean, he wouldn't have to run seven miles." Sammy complained.

"Dean checks in." John scolded her. "And he runs 10 a day… like I tell you to and you never do. Maybe if you did, you could keep it in your pants."

"John." Mary sighed and took a breath. She scratched at her scar and looked at her son. He seemed still, for the first time in a long time.

Dean liked Rosemary. She was nice. And gentle. And relaxing. It was a crazy week. It marked his fifth and most successful foray into heterosexual sex as a man, his first time with homosexual sex and his first threesome. On the ride back home, he and Caleb got to chatting for a bit. "I was 17… and I was kind of a slut. If it had a penis, it was my type. I ran off to get laid and I shacked up with this dude for like… three days. The booze was… really sweet…"

"So, what'd you look like as a girl?"

"Like Sammy… but with bigger tits. And a much better ass. She's so fuckin' lazy." Dean shrugged. "Anyway… I passed out, I guess. I woke up on a table. All these folks in robes. They tied up the wrong girl. No one told them that you don't fuck with a Winchester, especially not one who is also a Campbell. I fought my way out. My pussy was wrecked… I jumped to those conclusions. Then… Somehow… I made it home."

"Your dad said it was pretty painful."

"Took a whole month to change. One molecule at a time." He tapped his knee. "I… haven't told anyone this… Um…"

Caleb waited but Dean's knee was jumping hard enough the car seemed to rock a bit. "What?"

"I haven't fucked a woman in a while cause… the last time I did… I changed back."

"What?"

"Yeah. I turned back into a woman. Then… I freaked. I told him I was on the tail of something. I fucked a man… and I turned back. It was quick. Almost painless. I've been abstaining for awhile."

"Shit." Caleb looked at him. "You gonna be okay?"

"I think so… cause it was her, then you and then both. It might all cancel itself out."

"What happens if it doesn't?" Caleb looked him over but Dean had suddenly become completely still.

"Would it be so bad if I was a girl?" Dean waited a beat, his eyes on his knees, before he motioned between them.

"No. You're fucking pretty for a man. Your sister's hot. Your mom… she's hot. Fuck… your dad… he's hot. No way you're not hot as a woman."

"You're really gross."

"Your dad is hot. I'd fuck him. It's in the eyes. He's seen some shit and he carries it."

"Yeah. He watched his daughter sprout a penis."

"Your dad surprises me. I mean… he looks like this… Total Man. But he's cool. He's not all red state about it. And he kind of looks like a red state guy."

"I think he used to be like that. I mean, he was a Marine and after he married my mom… they started hunting together and he used to try to put her in the backseat, I think." Dean smiled at his knees. "She's… proper and didn't used to want to hunt but she didn't like it. Her house… was different. They hunted differently. The… dynamic, I guess, was different."

"Hunting houses are always different." Caleb commiserated. "I don't remember so much about my folks being with each other but I know my friends thought they were weird."

"I think… the whole thing… the way it happened… he just… like everything else… just rolled with it. Taught me to piss standing up, how to walk like a man… how to stop tumbling like I still had 10 lbs strapped to my chest. Fucking throws off your center when you're used to having huge tits." Dean shucked his shoes and pulled his jacket around himself. "Why did you let this get so heavy, so fast? You're a freak."

"Yes. I am. I like you."

"I'm gonna sleep."

"Go for it." Caleb heard the snores almost immediately. He glanced over every once in a while. It took three hours but by the time he'd pulled into the Winchester driveway, Dean was Deanna. There might have been a growl of pain and bit of stretching but the Winchester slept through the transformation. He picked her up and carried her inside passed the curious John and Mary and the obnoxious Sammy. He took her down to the basement and laid her out on the bed. She was beautiful. Way prettier than his usual tail. He got sixes and sevens. Deanna was a solid nine.

Mary was the first one to muster the courage to get all the way to the bottom of the stairs. "Caleb… is that…?"

"Yeah…" Caleb smoothed Deanna's hair back, it had grown two feet already. "I got Dean laid… a few times… and when we were almost here… this happened."

"After all this time." Mary breathed out and knelt next to the bed.

"It's not permanent." Caleb warned her. "Dean told me that it's happened before."

"But…"

"I don't know."

"Mmmth." Deanna started to open her eyes. "Where am I?"

"At home. In your own bed." Caleb told her. "Your secret is out."

"Ummpth." She slapped a hand on her chest. "God dammit. I don't have bras for these."

"Honey." Mary touched her face. "We'll go shopping… we'll raid Sammy's closet."

"It may not stick." Deanna finally got her eyes open. "I'm starving."

"No wonder… We've had a busy week and you… were busy while you were sleeping." Caleb laid a kiss on her forehead.

"Dude… did you just friendzone me?"

"No."

"You did."

"I was… being affectionate."

"Yep. Still Dean." Mary clapped Caleb on the shoulder and got up to herd the rest of the family back up the stairs.

"I didn't want them to see this." Deanna shut her eyes.

"They'll be okay. I'm okay. You're smokin'… even drowning in Dean's clothes."

"Why do you like me?"

"I like good tail." He shrugged. "And… it kind of fills my quotas. Some nights, I get pussy and some nights, I get dick."

"I've never been able to have anything this intense."

"Me either." Caleb kissed her forehead. "Maybe… we'll be able to figure this out… Maybe this will end in disaster."

"Maybe it'll be fine."

"One thing… I've never been able to share with any of the pussy or the dick or… the very lovely Rosemary… the hunting. It's part of me. It's in my soul. I dig what your folks got. I know your dad wasn't in it but he got in it and he stayed. Maybe it takes time to build it. I feel like maybe I could have it."

"We could have it?"

"You want this baldness in your life?"

"Yep. We gotta rope in Rosemary, though."

"You went there, fast."

"She could fit."