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Master Post || Part 1 || Part 2 || Part 3 || Notes

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Master Post || Prologue || 1 || 2 || 3 || 4 || 5 || 6 || 7 || 8 || Epilogue || Notes



Prologue

Dean knew John had tried to be a good dad. He'd loved his boys, done what he thought was right, prepared them for a world most people should never even know existed, let alone little boys that meant the world to him, little boys he wanted prepared for that world.

That didn't mean John would have won Father of the Year. Sure, Dean loved his dad, and Dean believed his dad had done his best in most of the situations he'd been thrown into, but the older Dean got, the more he realized that some of the things John had done and said weren't what people would call accepting or open-minded.

Dean swore to himself as a teenager that if he ever had kids, he'd love them no matter what, accept them no matter what. He'd let them be whoever they wanted to be. Dean knew his dad loved him, would kill and die for him, but the acceptance of whoever Dean wanted to be, well, that was an area where Dean was pretty sure his dad fell short.

It wasn't until he was in his twenties, though, that Dean fully understood what he'd let his father and society do to him. Living the way they had, Dean wasn't exposed to a wide variety of people for more than a short period of time when he was helping them, and when someone was scared for their lives or being attacked by something supernatural, it wasn't the best time to sit down and discuss feelings and other shit like that.

So Dean had stuffed his feelings down. He had built a wall. He'd developed a persona for himself. It worked well enough. He was attracted to girls his whole life anyway, so it was easy enough to fake the other shit.

When it came to hanging out with guys at school, he'd quickly learned to act like the loner. Not only did girls get a kick out of that, but he didn't have to put up with teenage boys.

Dean never fit in with boys. He felt disconnected. He never thought the way boys did. It was painfully obvious to him from a young age. It wasn't that he played with dolls or dressed up in pink outfits, danced about saying he was a pretty, pretty princess. No, Dean just knew his brain didn't work the way other boys' brains did.

Right about the time girls were saying boys were stupid and gross, Dean began agreeing with them. Not that he never did gross things himself, he wasn't a big baby, but boys just had this way about them that grated on him when girls never grated.

- - -

Part 1

Then

1987

“Dad, I want to grow my hair long like hers,” a six-year-old Dean said to his dad, pointing to a little girl about his own age sitting a few tables over in a diner. The girl's hair was dirty blonde, parted to the side with a tiny butterfly barrette holding her curls in place.

Dad had smiled at Dean. “Boys don't have long hair, and boys certainly don't wear barrettes in their hair.”

Dean had frowned as he looked back at the little girl's hair. “Why?” Dean asked.

“They just don't, kiddo,” Dad said, and the smile slipped from his face as he looked at Dean.

Dean wasn't sure why at the time Dad had looked at him that way, but as he got older, he realized that's when John started to see that his son was different and that difference had scared the shit out of John.

“When you're a boy,” Dad said with a sad look in his eyes, “you can't have everything you want in life. That's life. You just gotta suck it up because that's what a man does, all right, buddy?”

Dean wanted his dad's approval, like all little kids do, so he said okay, stole covert glances at the little girl's hair until she left the diner with her grandparents, and finished his dinner.

- - -

1989

Sarah and Dean had met a week ago when Dean had moved to town and started going to Springdale Elementary School. She came up to him at recess, asked if he'd wanted to play on the swings with her, and they'd become good friends by the end of the day.

Sarah's mom had set the two of them up out in the backyard with some lemonade, and Sarah had come outside with her My Little Pony collection and her brand new bottle of purple nail polish.

Eight-year-old Dean was so proud of the nice job he had done painting Sarah's nails, and Sarah had a big smile on her face as she held up her nails for him to see. He was so happy to have made her smile.

“Do you want me to paint your nails now so yours can be pretty like mine?” Sarah asked, holding the nail polish up and wagging it in Dean's face.

“Yeah!” Dean said without hesitation.

Sarah squealed, then very carefully painted Dean's nails for him. She was very good at keeping the paint on his nails, and she didn't get any on the skin of his fingers like Dean had done a little with hers.

Dean walked home an hour later, just in time for dinner. Dad was dishing up some goulash, and Sammy was sitting at the table with his spoon, all ready for his food.

“Dad, look! Sarah painted my nails for me! Aren't they pretty?” Dean said as he wriggled his fingers high in the air for his dad to see.

“Dean!” Dad said as he put the pan down on the potholder. He sounded exasperated. “Boys don't wear nail polish.”

“Why?” Dean asked as Dad took him by the arm and led him into the bathroom. He wasn't being rough, so Dean assumed this wasn't a huge deal.

“Because they just don't,” Dad said, picking Dean up and sitting him down on the counter.

“But I like it. It looks nice,” Dean said with a pout.

Dad got a bottle of clear liquid out from under the sink, doused a cotton ball with whatever was in the bottle, and then cleaned off Dean's nails. Dean's nose scrunched up at the strong smell, but he sat still and let his dad clean off his nails.

“But, dad, I like them!” Dean said a little louder, not pulling his hands away, but clearly upset about what his dad was doing.

“That's enough, Dean,” Dad said as he wiped Dean's fingers completely clean of any trace of the pretty purple nail polish.

Dean knew better than to throw a temper tantrum, but he was upset. He didn't cry, although his eyes were stinging. Dad had put his foot down, and Dean wanted to ask why, because Dad's answer hadn't really explained anything at all.

Dean washed his hands to get the stinky cleaner off, then followed Dad back out to the kitchen. Dean was quickly distracted by Sam having gotten goulash down the front of his shirt, so the issue of his nails was forgotten for the night.

Dean thought about what had happened for a really long time as he lay in bed that night, his flashlight playing over the cracks and imperfections in the ceiling. He didn't understand why girls got to do different things than boys, and he just wasn't satisfied with the answer of “just because.”

The next day was Monday, and since Dad hadn't given him a good answer, Dean decided he'd ask a teacher. He found a teacher, walked up to him, and asked, “Why can't boys do the same things girls do?”

Mr. Jessup had smiled at Dean, gestured toward the restrooms they were standing by, and had said very kindly and patiently, “Boys and girls need to have separate restrooms because they have different bodies and they need restrooms that are made just for them.”

Dean hadn't been asking about the restrooms, and it frustrated Dean, but he didn't want to backtalk a teacher, so he said, “Okay, well, thanks, Mr. Jessup.”

It still wasn't a clear answer to Dean. He knew boys and girls had different body parts. He wasn't stupid. Dad had been very open with him whenever Dean asked about stuff like that.

Dean found it silly that the other kids at school would giggle and blush whenever they talked about the differences between boys and girls' bodies, and he found it even more silly that some of the kids' parents had lied to them about those things. He didn't understand what good it did to lie about stuff that everybody had, to make up stories about babies when the truth wasn't really all that complicated.

Anyway, Mr. Jessup smiled at Dean, then walked away, so Dean ran outside to find Sarah. There were ten minutes left for recess, and he really wanted to play with her.

“Why did you take your nail polish off?” Sarah asked with a hurt look on her face, pointing at his nails.

Dean felt horrible. He really liked Sarah, and she'd worked so hard on his nails. The fact that her nails were still purple hurt his chest, because he'd really liked his nails painted, and Sarah had done it for him.

He was a little embarrassed that his dad had reacted that way, and he didn't want to tell Sarah the truth both because of the embarrassment and because he didn't want to hurt her feelings. It wasn't her fault that Dad had taken the nail polish off. Dean knew that in his heart.

“Sorry, Sarah,” he said as he held up his hands. “I was helping Dad clean something, and I didn't notice until I was done, but it washed off all the nail polish.”

“Oh,” Sarah said, the bridge of her nose scrunching up while she thought about it for a moment, then her face changed, a smile taking over her face, making her look happy again. “Okay, so do you want to play on the swings or the slides?”

Dean smiled at her, relieved that he managed to keep from hurting her feelings. “Slides!” he said as he took her by the hand and they ran to the slides.

- - -

1990

When Dean was nine years old, he was invited to a birthday party. Dad seemed happy that Dean was interested in playing with kids his age, so Dad drove him to the party, promising Sammy a pizza and movie night at home so Sam would stop whining about missing out on the party.

The kids at the party quickly separated into groups of boys and girls. Dean hadn't thought much of it at the time, and he'd just migrated toward the girls' group because he was more interested in what they were talking about and what they were doing anyway.

It wasn't a conscious decision of “I want to be with the girls instead of the boys,” but rather it was just where he'd ended up.

Ian, one of the boys at the party, saw Dean with the girls. Later Dean would remember Ian Sanders' name well, because even at only nine years old, this boy was responsible for Dean's epiphany, though Dean hadn't even known what that word meant yet.

Ian walked up to Dean, who was sitting on the floor with the girls in a circle. “Why are you playing with the girls and not the boys?”

Dean was puzzled by the question, but he answered anyway. “I just wanted to,” he said with a shrug, because really that was the only reason. There wasn't some deep philosophical meaning to his actions or anything.

Ian laughed at him, pointing and smirking. “Are you gonna let them paint your nails, Deanie?” Ian teased loudly, drawling out every other word like he was the funniest comedian ever. “Are you all gonna braid each others hair? Why don't you let them dress you up like a girl, and then when we play spin the bottle, maybe you can get one of the boys to kiss you!”

Dean was shocked speechless. Sure, Dad had said things before like “boys don't play with dolls” and “boys don't paint their nails” when Dean had shown an interest in each of those things, but it was a totally different thing to have it thrown in his face that he was different from the other boys and that actually all those things Ian had said sounded like fun other than the part about kissing a boy. That one was just eww!

Before Ian, Dean had thought other boys felt the way he did. It didn't matter that Dad had said boys don't do those things. Dean was a kid, so he'd always figured it was the same as “kids shouldn't run out into the street” and “only grownups can look at the magazines you found in Daddy's duffel bag.” Other boys wanted to play with the same things Dean wanted to, adults just didn't let them, right?

As Dean sat there, staring up at Ian with a dumbfounded look on his face, Allison, one of the girls in his group, stood up, shoved Ian so hard in the chest that he fell on his ass with a grunt, and then she said, “Leave him alone. We'd rather play with him than you anyway because he's much more fun than you, asswipe.”

Dean turned to look at Allison with a feeling growing in his chest, a feeling that made his lungs feel too big, like they were going to burst. Allison had accepted him without question. She'd even said she'd rather play with him than Ian, even though Ian was “so cute,” according to all the girls in his class, which he never agreed with anyway, but that wasn't the point.

“Don't worry about him, Dean,” Allison said with more confidence than Dean had ever heard from another kid. “He's just jealous because you're doing what you really want to do instead of what somebody else tells you that you should do.”

Allison then grabbed Dean's hand, dragged him closer to her, and along with all the other girls in the circle, completely ignored Ian and began another round of telephone.

Allison became Dean's first girlfriend, the title becoming official by the end of the night when she asked if he wanted to go steady and have lunch with her at the cafeteria the following Monday.

When the other kids at school found out he had a girlfriend, the little bit of teasing he'd endured over the weekend abruptly stopped. Apparently, Dean learned, if you hang around with girls and don't have a girlfriend, you're a complete freak, but if you hang around with girls and you got a girlfriend out the deal, you're really cool. Therefore, Dean was cool.

So even though Dean's epiphany had changed him drastically on the inside, if anything, his outside appearance had already cemented him as a normal boy, and Dean didn't do anything to dissuade anyone's notions about him.

- - -

1991

Dad was proud of him, and Dean was very happy that his dad was proud of him. Dean had a few more girlfriends after Allison, though all they'd done was hold hands and exchange a few kisses that were more like pecks.

Dad had talked to him plenty of times about being nice to girls, being careful with sex when he did decide to have it, and Dad had even gave him some pointers on how to make girls happy both in bed and in general so Dean could be a good boyfriend.

Ian was a big reason for Dean to not only realize a lot of things about himself, but he also was the reason Dean built up his persona, and not many people ever knew anything but Dean's persona.

It wasn't like Dean closed his real self off completely. He was just careful what he let slip. His life wasn't a complete lie, and nearly everything Sam knew about Dean was completely true.

Dean met a girl named Kayla at the end of the school year after turning twelve. Kayla was a year older than him, so they didn't share the same classes, but she was fun to be around, and they ate lunch together every day.

Kayla had gotten a makeup case for Christmas, and since she was very careful with her things, there was still plenty left by the time school was out.

Dean and Kayla played at her house because she had some really cool toys, and Kayla loved doing makeovers on Dean. Dean wasn't a huge fan of blush and eyeshadow, and the lipstick would get stuck on his teeth, but he really liked Kayla, and she really liked him, and anything that made her smile was worth in Dean's eyes.

Kayla had some makeup remover that Dean would use before he left her house. He knew his dad wouldn't like it if he found out Dean was wearing makeup. Dean hadn't ever asked, hadn't ever come home with it on, but considering the nail polish incident, Dean assumed makeup would get the same reaction.

One night Kayla and Dean had been making and then playing with origami fortune tellers, which Dean hadn't known how to make, so Kayla was showing him how to make really cool ones.

They hadn't played makeover, but Dean couldn't resist putting on a little bit of lipstick, not caring it would get on his teeth because it made his lips look pretty. They played until it was time for Dean to grab Sam, who had been playing with Kayla's little brother downstairs, and get home to order a pizza.

Dad had just pulled into the driveway of the apartment complex when Dean and Sam had walked up. Sam ran inside while Dean took Dad's duffel from the back seat of the car.

“What's that on your lips?” Dad asked, his eyebrows drawn down.

Dean felt a rush of panic run through his body, but he kept his cool. Even at twelve, Dad had taught him well how to play people.

“Kayla had lipstick on,” Dean said with a leer and a waggle of his eyebrows.

Dad laughed, ruffling Dean's hair. “That's my boy,” he said as they walked to the apartment.

Dean breathed a sigh of relief as he followed his dad. John had assumed, just like most other people, that Dean's persona was the real thing. It kind of hurt that his dad hadn't seen through it, but Dean also knew Dad wouldn't like what was beneath that persona.

- - -

Over the years, a few girls had noticed small things, but they never got the whole picture. Rhonda Hurley had been thrilled when Dean agreed to wear her pink panties, but other than the whole thing being a big realization for Dean that some women got a kick out of men wearing women's panties sometimes, he hadn't really told her about anything else.

And Dean would be forever grateful to Rhonda for not only his realization of girls getting a kick out of that, but also that he himself got a huge kick out of it. Her panties felt so soft, and if only his dick and balls weren't in the way, the panties would have fit perfectly, but he'd take what he could get.

Dean kept a pair of panties underneath the rest of his things in his duffel bag after he was with Rhonda. They weren't hers, but he'd had no trouble going out and buying a pair at the store. He'd lied and said they were for his girlfriend, and the salesgirl had cooed over what a wonderful boyfriend he must be, and Dean had a great time picking them out with the salesgirl's help.

He was careful about when and where he wore them. He knew better than to wear them on a hunt, because if he'd gotten hurt, he might've needed to be stripped by dad or Sam. He enjoyed panties, but he wasn't careless with them.

He loved looking at himself in the mirror with them on. The muted maroon color looked so pretty with his skin tone, and the way it hugged his body, the way the lace at his waist tickled his skin, it made something fall into place inside him. Something he never thought would feel so right.

The panties weren't a completely sexual thing, but that didn't mean he didn't jerk off plenty of times into the panties.

- - -

Meeting Cassie was both the worst and the best thing that ever happened to him. She wasn't a stupid girl, so she'd seen through his carefully-made persona so quickly that it had taken Dean's breath away.

She was okay with it. She was accepting in a way Dean wished everyone could be. She didn't act like it was something that needed to be talked about or something that needed to be focused on. It was simply who Dean was, and she wanted Dean, all of him.

Except that she didn't. Dean had figured since Cassie had dealt with his gender issues so well, she'd have no problem accepting the supernatural. In his mind, he'd built up his gender issues to the point where the supernatural was a piece of cake in comparison.

It hurt. A lot. She wasn't mean about it, and she reassured Dean it had nothing to do with him as a person, but Dean had always thought of true love in a romantic way. True love was something that broke through barriers, was unconditional like you see in the movies, and that if someone just loved him enough, they wouldn't care about anything else.

After all, wasn't Dad's entire mission in life seeking revenge on the demon that destroyed the fairy tale romance that was Mary and John Winchester?

It wasn't until his experience with Cassie that Dean's romanticized view of love got shattered. Sure, there could be romance, and there could be love, but no one's love was completely unconditional, no matter how much a person thought it was. So Cassie had been the worst and best thing that had ever happened to him.

- - -

Lisa? Well, she was so much fun that Dean couldn't have cared less if she'd accepted anything else. They'd done everything together, including pegging, which was a first for Dean at the time, and he discovered that he'd really liked it.

She took charge in the bedroom, and he gladly gave her that control. Not that he was a slouch in bed, but rather she came up with all the stuff they did, had the toys to play with, and when it came time for their weekend to be over, she was the one who let him know fun times were had by all, it was time to go back to their real lives, and it would be great if he could stop by every once in a while to do it all over again.

Dean knew he wasn't the type to settle down, at least not yet. And even when Sam made him promise that he'd settle down with Lisa, Dean knew it wouldn't work. Lisa was great. He even loved her, would always love her, but settling down wasn't for Dean. Not yet.

But Dean had skipped ahead in his musings, in this story of his life. Mostly because the thing he'd skipped over had been something that really rocked his world in a bad way, made him question everything about himself, and hurt so badly that he wished he could erase it from his head.

Dean had always thought that maybe he'd just accidentally been given a male body. He knew about biology. He knew that an extra few doses of testosterone or estrogen while a baby was developing had a big enough impact on a person that it could make a girl a tomboy or a boy more effeminate. So he figured some kind of accident happened when he was developing. Accidents happened, right?

But when he'd been remade as a male by an angel, an angel sent by God, well, it was a huge blow to everything he'd ever known.

Angels and God had seen him as male, without a question. And they should know. So maybe Dean was just confused. Or maybe he was fucked in the head. Maybe he was just a pervert who liked women's clothes and liked women so much he didn't even care to be around a guy other than his own brother.

Whatever it was, Dean seriously reevaluated his lot in life. After all the chaos died down from his resurrection, meeting an angel, and all of the utter ridiculousness of the shit the angels pulled on them and everyone else in the world, Dean gave up.

Not on life. He didn't really want to die. But he gave up on letting himself be who he was on the inside. It didn't even hurt anymore. He was too numb from life, from Hell, and from fighting for something that never should have been in the first place.

Drinking helped. And the fact that he still wanted to fuck girls helped. Dean liked sex. It was fun, it was a distraction, and making a woman come over and over again was something that never got old, something he was very good at.

The strangest part of the whole gender thing, in Dean's opinion, was that none of it had been used against him in Hell. He figured everything was used against everyone in Hell. When it was his turn to torture souls, he'd used everything he could find against them.

So it was a mindfuck in and of itself to have Alastair completely ignore something so significant about Dean as his gender issues.

And of course that made him question how much of it had been real and how much had been something he'd built up in his head.

- - -

Everything came to a head when he met Charlie. She was great. He instantly felt something for her. And when he'd found out she was a lesbian, a part of him craved that feeling he used to let himself have around women like Rhonda, Cassie, and Lisa, but he'd been hit too many times in life. He was tired of getting back up again.

He figured Charlie would want nothing to do with him sexually. She seemed to like him as a person, and she was so funny and adorable that he wished for more. She was just so damned cute!

And even though she was scared of the supernatural, she didn't back down. Dean could respect that in anyone, especially a hot chick.

But she was giving him calculated looks, and she was smarter than most people gave her credit for at first glance.

- - -

Now

So even though Dean had given up on letting himself be who he really was around one-night stands, whether he thought they might be up for it or not, it isn't a complete surprise when Charlie comes to his room at the bunker and pulls two bottles of beer out from behind her back as she flops down on his bed.

He smiles on the inside because he realizes she's probably trying to liquor him up, trying to get him to open up and talk to her, but the poor girl doesn't know how much liquor it would take to get him thoroughly sloshed, and it isn't one damn beer.

She holds a bottle out to him, waggling it back and forth with a grin on her face. Dean chuckles. He can't help it. As previously mentioned, she's damn cute.

Dean sits down on the bed, turned toward Charlie, takes the beer from her hand with a grateful smile and takes a sip.

“So, Dean,” she says in a way that seems like it could get awkward soon.

But Charlie has always had this amazing ability to be un-awkwardly awkward. Dean doesn't know how to describe it other than that, but it's part of what he's grown to love about her.

“So, Charlie,” Dean says as he relaxes back against the head of his bed, comfortable in his T-shirt, jeans, and socks.

“I have this really strong urge to do something with you,” Charlie blurts, then runs her fingers through her hair nervously. “I don't want to be presumptuous, but I think if I leave it up to you, you're never going to bring it up or do anything about it. And I think you really do want to bring it up, because I think it's something you really want. And if I'm totally off base here, just tell me and I'll never bring it up again, but you have to swear never to bring it up again and use it against me. Because I care about you, and that's why I'm bringing it up. It's not because I want to humiliate you or something like that. So don't hate me,” she says, ending with a wince.

“Breathe,” Dean says with a small smile on his face. The words are hitting him, making his stomach clench because he has an idea what she wants to talk about, but Charlie rambling on is so adorably her that he can't help but smile.

Charlie takes a deep breath, then bites her lip, plays with the hem of her tan V-neck shirt, which makes her tits look awesome, in Dean's opinion.

“I have to just say it. And for the love of god, please stop me if I'm saying something really, really stupid before I finish it, and please don't hate me,” she repeats.

Dean chuckles. “I'm not gonna hate you, Charlie,” he assures her. “Blurt it out. Just get it over with.”

“Okay, fine,” she says, then seems to consider her words for a moment. She looks up at him with determination shining in her eyes. “I think you're not comfortable in your own skin, that you want to be on the outside who you are in the inside, but it hasn't happened for whatever reason, and it's made you give up.

“I think you've stuffed it down so deep that you think nobody sees it, but I'm seeing something because you can't stuff something like this down completely, and it's hurting you, and I really like you, and I want to help you, and stop looking at me with that adorable mix of apprehension, excitement, and relief,” she finishes with a pout.

Dean doesn't know what to say, and he sits there staring at her as if she's a bomb about to go off. She still hasn't said flat out he's a woman trapped in man's body, and Charlie might not have even gotten that far in her observations, but she's close enough that the apprehension, excitement, and relief she saw on his face was exactly right.

He looks down at his beer bottle and picks at the label, not wanting her to see how vulnerable he feels. He can't let himself be that vulnerable.

“Am I wrong and I should shut up and we forget everything I just –,” Charlie starts.

“No,” Dean interrupts, then lets out a nervous chuckle, but still stares at his beer, still picks at the label. “You're not wrong. I'm just wondering how far you've taken this idea in your head and how close it is to the truth.”

“So,” Charlie drawls. “I'm not just reading you wrong?” she asks.

Dean shakes his head. He wants to look up at her. It's becoming hard to keep his eyes on the bottle, but he's scared of what she'll see, what he'll see. “No,” he says, but he doesn't know what else to say.

“How long have you felt like you don't fit in?” she asks with nothing but care and concern in her voice. There's no censure, no judgment.

Dean chuckles awkwardly and leans his head back against the wall, his eyes closing. That conveniently lets him hide for just a little longer. “I figured it out at a birthday party when I was nine years old,” he says softly.

“Uhm, okay,” Charlie says, obviously floundering for what to say, hoping he'll fill in a few blanks, or maybe even just confirm what she probably already knew instead of simply filling in blanks.

Dean sighs, shoves the bottle down between his legs, then plays with the mouth of the bottle with his fingers. “I was different before then, but the party was the eye opener,” Dean says with a huff of laughter over something that wasn't all that funny. “I didn't always hide it. There were a few women over the years who have known or have found out or ones who I've told, and they've been really okay with it. Surprisingly okay with it. Others who didn't handle it so well,” Dean says vaguely.

“So since you're apparently not going to put me out of my awkward misery, I'll just have to make an educated guess,” Charlie says, and Dean lifts his head up to look her in the eye finally. “You've always fit in with the girls instead of the boys and you've thought you should've been born a girl instead of a boy, and you've always been attracted to women, so it allowed you to, in a relatively easily way, keep up the facade of heterosexual ladies' man.”

Dean doesn't know what to say, so he just nods, feeling numb. He purposely had kept eye contact with her, learning in the past that it was a good tell for women, made it easy to spot if they were okay with him or not.

Women were always fairly easy to read for Dean. Not in the way men were. Women didn't blurt out their feelings or proclaim it for the world through body language and loud remarks like men. No, women were usually subtle, even the ones who were more loudmouthed and brash. It's all in the minute changes of their posture, the tension in their shoulders, the changes in their eyes, the small movements of their lips, where they look, and everything in between the words they say.

Charlie's not disgusted. There's still no judgment. She's concerned, obviously cares about him, but there's no pity, no motherly instinct kicking in and forcing her to come to his rescue. She's looking at him with confidence even though her words might tell the average observer she's unsure of herself.

And maybe she is a little hesitant, but it's only because she wants to be delicate about this, doesn't want to hurt him with lack of tact, and it's not because she's unsure whether or not she's right about this.

Playing with the hem of her shirt gives her something to do with her fingers, not out of a nervous habit, but because he can tell she wants to touch him, even if it's just to rest her hand on his knee.

Dean has no idea why men have such a hard time reading women other than they're probably just not paying attention. Sure, women can be sneaky, they can hide their feelings under layers of subterfuge, but if you care enough to figure them out, a women will tell you everything you want to know with every atom of her being, and if you earn her trust, she'll give you the world.

“Have you ever told your family?” Charlie asks, tilting her head to the side in a way that Dean finds adorable.

Dean shakes his head. “No, not directly. My dad was the type of guy who said boys don't play with dolls, which I was never interested in anyway, and even though I never said anything to him or let the whole truth show in front of him, I don't think he would've handled it well because of how he handled the things I did let slip as a kid. And with Sam, I really don't know how he would've reacted, but I never tried with him either.”

There's still no pity on her face or in her body language. There is, however, a subtle straightening of her posture that shows intent, shows that she thinks she can help.

“Do you want to do anything about it?” Charlie asks. “I mean you've been doing this for a long time, I know that, but you don't have to. And I don't want to put you on the spot or anything, but I want to help. You have this way about you, this look on your face like you've given up, and I want to do something about it, because I really do like you.”

Dean smiles at her. “I really like you too,” he admits, though he figures she doesn't know how much he likes her. Then he thinks about the rest of what she said. “Oh, about the whole giving up thing,” he says with a big sigh, runs his fingers through his hair, but doesn't elaborate yet.

Charlie holds up a hand. “You don't have to tell me if you don't want to, but like I said, I'd really like to help,” she says with a hopeful look on her face, her hand going back to her lap, fingers teasing the hem of her shirt again.

Dean can't resist being honest. She's being genuine. She's not teasing him or walking away. Her posture, body language, facial expressions all say she's safe. He can tell her.

“You know all that shit about me going to Hell and coming back?” he asks.

“Yeah,” she says, and Dean's relieved that there's no look of pain or disgust on her face when Hell is brought up.

“That's about the time I gave up,” he says with a sad smile. This part hurts, and he feels it in his chest before he even says it. “When Cas brought me back, he made me this body,” he says pointing at himself.

She takes that in. “Oh, I see,” Charlie says with a wrinkling of her nose, almost like she's a little pissed. Her voice when she speaks again gives an edge of challenge. “So an angel remakes you, and because you'd grown up thinking it was a mistake that you were in a male body, it totally blew you away to have an angel throw it in your face that it wasn't a mistake, you had the right body the whole time, so you figured you were wrong all your life and you should just suck it up and live with it, right?”

Dean looks back down at the beer bottle. His chest is hurting even more, and he doesn't know if he wishes Charlie were less observant or if he likes that she's seen this about him. He likes commiserating with women. Never felt right with men. And she's practically begging.

The challenging tone in her voice turns into fire. “Well, I think that's bullshit,” she says indelicately.

Dean looks back up at her, surprised by the conviction in her voice. “What?” he asks, one eyebrow raised.

She snorts. “How do you know Cas didn't just remake your body that way because he was doing just that; remaking your body?” Charlie asks as if he's a dork for never thinking of it that way

Dean's mind is blown. It's blown so badly that it must show on his face because Charlie's expression softens some. “I, uhm, hadn't thought of it that way,” he admits, a sheepish grin on his face, and he feels his cheeks flush.

“You've said before that angels are so totally different from humans,” Charlie argues.

She sets her bottle down on the floor beside her, and Dean knows it's because she wants to involve her hands in the conversation. It's another one of those things he really likes about her.

Charlie looks him in the eye, her hands already getting involved now that they're freed up. She waves toward the ceiling. “They're built for carrying out God's will. Even though they have the ability to have emotions, they're still awkward and have a hard time fitting in with humans even after being with them for a long time,” she says, then smacks his leg. “So what makes you think Cas wasn't just doing his job, carrying on in his mission from God by recreating you?”

His head's spinning. “I hadn't thought of that,” Dean says softly, feeling stupid for it never having occurred to him. He shrugs. “I just figured Cas saw me, inside and out, and saw that everything about me was male and recreated that.”

“Did you ever ask him?” she asks, her hands going out to her sides in a posture Dean likes to call a woman's 'well, did ya?' pose.

Dean shakes his head. “No. I didn't see a need to ask,” he says, setting his bottle down on the nightstand. “And I figured I was fucked in the head, so I just assumed he did the whole soul searching, creating-me-the-perfect-body thing, that's why he did it, and I gave up on ever having anything else.”

“Did Cas tell you that you were fucked in the head?” Charlie asks with her hands flopping down onto the bed on either side of her, fingers clenched and showing that she's ready to punch Cas in the face if he did say that.

Dean thinks about that for a moment, tries to remember if Cas ever even implied it. “Well, no,” he admits, sheepish grin on his face again.

Charlie rolls her eyes, her fingers relaxing now that the possible need to punch Castiel in the face has passed. “From what you guys have told me, you were supposed to be the righteous man,” she says, then uses her index finger to poke him in the chest, “and don't get me started on how things can get lost in translation as far as the whole man versus woman versus human thing,” Charlie says with a roll of her eyes, “but anyway, why would an angel let something that big go without saying anything about it? Why would he side with you, disobey Heaven and fall for you if he thought you were that fucked in the head or perverted or whatever?”

Dean feels as if he's been punched in the gut. “I don't know,” Dean whispers.

Charlie obviously can't take it anymore. She has to touch, so she reaches out and rests her right hand on his calf. “Has Cas ever sat you down and given you the 'boys play with toy cars, girls play with dolls' speech and tried to set you straight?” she asks.

“No,” Dean mumbles, liking the warmth of her hand on his leg.

“Well then snap out of it!” Charlie nearly growls as she flings her arms out to the side, the bed shaking with her enthusiasm. “You feel like this your whole life, you squash it down, only letting yourself out to play a few times with a few women, then completely squash it down just because some angel gave you a look-alike body,” she says incredulously, then she scowls at him. “I say fuck that. If God can accept murderers and rapists if they repent, why can't he accept someone he's already damn well accepted who has felt like she's in the wrong body her whole life.”

The change in pronouns makes Dean's eyes widen and his breath catches in his throat. No one has ever said anything like that to him outside the bedroom. Not even Cassie had switched and used she or her outside the bedroom. And Dean considered bedroom time roleplay, so it never meant more than fun.

A grin spreads across Charlie's lips. “That felt good, didn't it?” she asks, watching him carefully.

Dean chuckles and blinks away the tears that had started to form in his eyes. “You're evil,” he says as he points at her, trying for light before he starts bawling all over the place.

She chuckles, then her smile dies away, and in its place comes a serious look. “What's in your pants doesn't define you,” she says, her hand coming to rest on his calf again. “People are so stuck on physical appearance even when they want to be all politically correct and accepting and see what's on the inside, and it usually doesn't happen until you truly get to know someone, but Dean, what's on the inside really does matter more than what's on the outside,” she says as she squeezes his calf.

Dean puts his hand over hers. “That all sounds good, but the steps toward that seem...,” he trails off with a huff. “Well, they don't seem all that fun or easy.”

Charlie tilts her head. “You have to do what's right for you, but like I said, I want to help,” she says with a reassuring smile. “As you know, I'm a woman,” she says with a chuckle, and it makes him laugh. “And as you also know, I really, really like women, and I really like you, so who better to help you with this?”

There's nothing but sincerity coming from Charlie. And he wants this so badly. He's scared. Hell, he's scared out of his mind of what this could all mean, how people would react, but he's never been all that much for conforming to society anyway, so why should he give a shit?

“We could start small,” she says with a grin, a raised eyebrow. “You don't have to tell anybody. Or you could decide you want to go all out and have a party and dance around in a sexy teddy!” she says as if she finds the idea of a party very exciting, and she bounces on the bed a little in her excitement.

Dean laughs. “Oh, god, no. I'm not ready for that,” he says as he shakes his head.

“Then we start slow. Not a problem!” she says with complete confidence, and he can feel the excitement growing in the room. It's coming from her, and it's giving him hope.

And the way she says it, how easy it sounds, how 'normal' it sounds, well, it makes Dean's shoulders relax a bit. She's made it sound easier than he'd built it up to be in his head. She makes it sound as if it's something he could try.

“Oh, and just to get the disclaimers out of the way,” she says as she smacks his leg. “If we start doing all this and you decide you don't like it or it's not for you, I'm not going to have a problem with it. I'm not going to tease you or say you're a failure. It's just you, and I already like you, and I'm not going to stop liking you just because you've decided lacy panties aren't your thing.”

Dean groans loudly, his eyes falling shut and his head thunking against the wall. He feels Charlie hop off the bed, and he looks up at her, her face alight with 'I'm so thrilled I can't stand it' written all over it.

“Now I totally know what we're doing first!” she says as she bounces on her toes. “We are so getting you panties! Come on! Come with me!” Charlie says, then gasps, her eyes widening even more. “Let's both get some! Ooh! We can get matching panties!”

Dean feels his dick twitch as he chuckles, and he hopes Charlie doesn't notice that his dick is interested. Well, even if she does, he can blame it on the panties themselves, which really is something he wants as well as being a turn on personally, but it also is the idea of seeing Charlie in panties.

- - -

Dean tenses as they get closer to the doors of the lingerie store. Since Charlie's holding his hand out of sheer enthusiasm, she has to be able to feel him tense.

She stops, turns to him, and gets a stern look on her face. “There's a difference between telling everyone your personal business and being comfortable enough with yourself to leave things up to imagination.”

“Huh?” Dean says with a puzzled expression. He feels very out of his element even though he's gone into lingerie stores before. He's bought panties under the guise of being an awesome boyfriend, but this time is different.

Charlie snorts and grabs him by the chin. “Just because we tell the salesgirl I'm your girlfriend and you're picking out panties for me doesn't mean we're compromising or selling out or conforming to society's standards. We're picking our battles,” she says.

Dean chuckles, the anxious feeling that had crept in receding. “Okay. Thanks,” he says, feeling silly now for having thought Charlie would announce his real intentions for purchasing panties to the entire store.

Charlie grins, grabs his hand again. “And if we happen to grab a few pairs of panties that are a few sizes bigger than my size, that's nobody's business but ours,” she chirps, then drags him inside the store.

- - -

Two and a half hours later and three bags full of lingerie later, Charlie and Dean get back to the bunker and sneak to Dean's room. Dean still isn't comfortable with Sam knowing about any of this, and Charlie has reassured him multiple times that it's okay, that he may never feel comfortable enough to tell Sam, but it's his choice.

There's something new with Charlie too. Walking into the lingerie store was a turning point in Charlie's speech patterns. Dean hopes she won't say anything like this around Sam, and Dean figures Charlie won't because she's just that cool about it all, but Charlie has been calling him Dee and has made a couple of comments about “how pretty this will look on you” and even offhandedly commented when Dean picked up a green tank top, “She knows what'll go with her beautiful green eyes!” to no one in particular, but it made Dean smile.

Dean's not sure if he's ready for Sam to hear things like this. But it's growing on him, and the first few times Charlie called him Dee, he felt a thrill go through his body. And the way Charlie says Dee sounds so natural, like a shortening of his name and one that can be taken as just that instead of a feminizing of his name means that Dean doesn't really have to worry about it even in front of Sam. Charlie is so... Charlie.

And if she called him Dee in front of Sam, Sam might tease him a bit for it, but only because it's so adorable, and Sam would just have to because he's Dean's brother. Brothers have to tease. It's in the sibling handbook.

Whatever it is Charlie's doing, Dean's warming up to the idea quickly. It feels good down to his core. Charlie is more than accepting. She's more than helping him. And he's more than just falling in love with her a little bit.

“Try them on! Try them on!” Charlie squeals as Dean closes his bedroom door behind them.

He turns around and nearly falls over his own two feet as he sees Charlie pulling her shirt off. His mouth drops open and he flat out stares at her.

She looks at him over her shoulder. “Clothes! Off! We couldn't try them on in the store, so you have to now! I wanna see!” she demands.

She has so much excitement in her voice that it stops Dean from staring, but then he hesitates when he realizes she means he should strip right here, right now. Not that he minds getting naked in front of a chick, but usually there's sex involved.

“Clothes! C'mon!” Charlie says as she looks over her shoulder again. She unhooks her plain black bra and flings it into the corner of the room.

He knows she knows he's hesitating, that he's not sure what to do. And he knows she's purposely trying to lighten the mood to get him to just forget about his reservations and just go for it. So that's what he does. His boots go first, then his shirt.

By the time he's undoing his belt, Charlie's completely naked, and he tries not to stare at her adorably perfect ass, tries to work at getting his clothes off, but it's hard.

And speaking of hard.

Dean freezes. He can't take his pants off now. He wouldn't even get away with hiding it if Charlie were to turn around right now.

He grumbles to himself. Dicks are so inconvenient. He shouldn't have to deal with this. Dicks are ugly, messy, and there's no way in hell to hide it if you're aroused. It's like dicks have a mind of their own and want everyone else to know what's going on.

Pussy is perfect, in Dean's opinion, and not for the first time he wishes he had one. They're so pretty and soft, and even when they do get messy, it just makes them more fun to lick and suck. But he has a dick, and he wishes he had a bag of ice to shove down his pants to get rid of the growing inconvenience.

“Nobody's in complete control of their bodies,” Charlie sing-songs loudly. “I'm not going to run away screaming just because you're hard.”

Dean blushes hard and lets out a nervous chuckle. “Sorry,” he says, not knowing what to do with his hands.

“Don't be sorry,” she says as she starts pulling their recent purchases out of the bag nearest to her. “I have a cute ass, as I've been told many times, and it leads to reactions from body parts,” she says as she turns to him, batting her eyelashes.

Dean lets out a bark of laughter, then decides to just do it. He takes a deep breath and just undoes his pants, pulls them off, and gets his socks off. He tries to ignore the semi he's got going on and walks over to the bed, where Charlie has spread out some of their new panties.

She's looking over their choices. “You should probably try these first, at least until your dick calms down a bit and you can fit inside some of the smaller ones,” she says as she holds up a pair of panties that have a little more substance to them than some of the other panties they've bought.

Dean takes the panties from her, and his cock twitches at the idea of putting them on. Charlie had picked these panties for him. They're light blue cotton boy shorts with bright pink trim around the waist and the same bright pink around the legs in lace. They're simple, and Dean had expected Charlie to go with thongs and more revealing panties, but he figured she knew what she was doing. He wasn't complaining.

He's momentarily distracted, getting his first fairly good glimpse of Charlie's pussy. From what he can see, Charlie's got just a little tuft of dark red hair at the top of her pussy, and the rest looks like it's either shaved or waxed. He tries not to stare, closes his eyes a moment to stop himself, then remembers the panties in his hand.

Dean pulls them on, not really knowing what to do with his very hard cock once he gets the panties up, and he yelps when Charlie just grabs his dick, holds it against his pelvic area to the left, and pulls the panties up around it, letting the waist snap up against his lower belly, the panties bulging out obscenely around his dick, but still managing to covering it.

“Mmm, very nice!” Charlie says, nearly growling and clearly checking him out. “Turn around, sexy,” she says with a twirl of her fingers.

Dean does as he's told, feeling only slightly ridiculous until he finally notices how nice the panties feel. They're the perfect size. Charlie had done a great job with picking them. Dean shivers when he feels Charlie's finger run over the lace, and it's then that he realizes the back side of the leg holes curve up a bit, leaving his lower ass cheeks outside the panties.

“Your ass looks amazing in these,” Charlie informs him, practically leering.

He does feel sexy. He feels soft and warm at the same time. He feels right. Even though his dick is hard, he's never been in a situation where he's wearing panties with someone else right there and it's not a sexual thing. He kind of wishes it was sexual, but at the same time it's nice to share this with Charlie. He'll take her however he can get her, and this right here is fun, and it'll have to be enough.

“Put on the tank top,” Charlie says, holding the matching top out to him.

He slides it on, loving how it molds perfectly to his upper body. The straps are about half an inch wide and bright pink, just like the trim on the boy shorts. The body of the top is the same light blue as the boy shorts, and the cotton is very soft.

“That. Is. Hot,” Charlie breathes as she stands back and checks him out from top to bottom and back up again. “How does it feel?” she asks as she looks up at him expectantly.

Dean runs his fingers gently over the top, making himself shiver. “Awesome!” Dean says with a big smile.

“My turn!” Charlie says as she grabs a pair of panties in her size from the pile.

She pulls them up and does a little spin so Dean can see how they look. They're sheer white with half-inch, white elastic bands at the legs and waist, the sheer fabric ruffled at the edges. They hug her body just right, and the little green bow below her belly button finishes the look. Dean moans loudly, nearly drooling.

“I take it that's a yes on keeping them,” Charlie says with a giggle, then picks up the matching bra. She gets the bra on and then strikes a pose for Dean. “Well?”

He can see her nipples through the fabric, and even though he'd just seen her nipples without anything obstructing them, now he really wants to lick them through the fabric, but he controls himself, motions for her to spin around for him, then nods as she does a spin.

“They accentuate the shape of your hips. Very nice,” he drawls.

She smiles at him. “And you can see my nipples,” she stage whispers at him.

Dean chokes out a laugh. “Yes. Yes, you can,” he says, his eyes roving over her breasts.

“Okay, get them off. We have a bunch more to try on!” Charlie says as she unhooks her bra and tosses it on the bed.

Charlie pulls on a pair of yellow-trimmed Batman underoos, then the matching tank top. The fabric is thin cotton, and Dean wants to mouth over the Batman symbol that's resting just above her pussy.

“Less drooling, more changing!” Charlie insists as she bounces on her toes, her tits bouncing along with her.

Dean gets lost watching her breasts bounce in his face, so Charlie grabs a pair of black lace tanga panties and tosses them at Dean.

“Your dick is never going to calm down if you keep getting all excited,” Charlie teases with a smile.

Dean chuckles. Charlie doesn't seem to give a damn that his dick is standing at attention, so he relaxes a little. He'd rather it either calm down or even just turn into a pretty little pussy, but if Charlie's okay with it, he can chill out about it.

He holds the panties in between the fingers of his left hand as he pulls off the boy shorts and tank he's wearing, then pulls the tanga panties on. Again they're a perfect fit other than his hard dick, and again Dean is a little confused as to what he should do with said dick.

“Here, let me get this for you,” Charlie says, and before Dean can protest, she grabs his dick again and positions it so the left hip band is holding it against his body, but the head is peeking out toward his left side and leg.

“Sorry,” Dean mumbles, his cheeks flushed again. Okay, so maybe he wasn't as okay with his dick joining the party as he'd told himself.

Charlie stands up straight, looks him in the eye. “Dee, it's part of your body. I know you'd rather have a pussy, but until you decide different, it's part of you, and it's not bothering me, so chill out, okay?”

Dean gives Charlie a dorky grin. “Okay.”

“Good, now that looks hot! You're totally keeping those!” Charlie says as he spins for her.

Dean chuckles. “You would tell me if you didn't like something, right?” he asks, wondering if she's just trying to build him up about the whole thing.

She looks at him with a 'well duh' look on her face. “Of course!” she says. “But I'm pretty sure most of this stuff's going to look amazing on you, so suck it up and put this on,” she says as she hands him a silky white teddy with little pink polka dots.

Dean takes it from her, then can't help but shiver again. It's just so soft and silky. He wants to fully experience this one, so he slides it slowly over his head, lets it fall gently over his chest and stomach. Charlie had purposely picked out a teddy that was more flowing and silky versus fitting so his lack of breasts wouldn't be painfully obvious.

“Oh, Dee, it's so pretty!” Charlie coos as she fixes the straps on his shoulders.

It falls to just below his panties, and everywhere it touches he feels all tingly. Dean is just about to start feeling himself up when Charlie leans in and rubs her cheek against his chest. His breath stutters, but he tries to hold still. She wraps her arms around his waist and tickles his back with her fingers through the teddy.

“I bet if you were to bend over, your panties would look so gorgeous peeking out from under this,” Charlie says.

Dean swallows a moan and tries his best to stay still even though he can feel Charlie's breath ghosting across the fabric on his chest.

“Do it,” she says suddenly as she pulls away from him. She does a spinning motion with her index finger. “Turn around and bend over a little.”

Dean blushes again. At this rate, his cheeks are just going to give up and remain red for the rest of his life. He huffs at her.

“C'mon, I want to see your panties,” Charlie whines.

Dean lets out a nervous chuckle, but he turns around and bends over a little. His cheeks feel like they're on fire.

“Hell, yeah!” Charlie yells from behind him.

Dean flinches at her outburst, so nervous that he's on edge. Charlie doesn't seem to notice, or maybe she's just trying to make him realize all of this is okay and to stop being such a big baby about it. Dean yelps as Charlie smacks his right ass cheek.

“Gorgeous! You're keeping these too,” she declares.

Dean quickly stands back up and turns around. “Your turn,” he says, then picks his way through one of the bags he'd carried in.

He picks out a green lace thong for her, knowing the outfit will look beautiful with her hair and skin tone. As Charlie puts the panties on, Dean grabs the top. It's the same green as the panties, but is sheer fabric instead of lace. It fits like a bikini top, the sheer fabric falling from the bottom of the bra to just above the top of the panties. The spaghetti straps and stitching are a slightly darker green and accent the rest of the fabric.

She puts the top on and she wriggles around a little, getting a feel for it. “This one isn't as comfortable as the other ones. I might take this one back,” Charlie complains.

“No!” Dean blurts. “It's fucking amazing. Even if you don't wear it all the time, you've got to keep it to impress a date.” He doesn't say he'd like if she kept it for him even if that's what he means.

“Really?” Charlie says as she looks down at herself.

“Really. The green is perfect on you, and the whole thing is...,” he trails off, mostly because he's trying to think of how best to describe just how hot it is. “It's very feminine and flattering,” he finishes, surprised when he's able to speak coherently.

Charlie giggles. “Okay, well, since you say I have to keep them, then I guess I have to keep them,” she says with a big smile.

“I do insist,” Dean says, nodding exaggeratedly.

Charlie's stomach growls and the two of them laugh. “I'm hungry, if you hadn't noticed,” she says without any embarrassment. “All this trying on clothes has got me starving! How about you throw all this stuff back in the bags, get comfortable on the bed with my laptop, and find a movie to watch while I grab something for us to eat.”

“Okay, dinner and a movie sounds good,” Dean says, then freezes as he wonders if he stepped over the line.

Dean watches as Charlie takes off her top, tosses it on the bed, then puts her shirt back on without a bra. She wriggles into her jeans, then waves to him as she leaves.

He's relieved she didn't freak over his dinner and a movie comment. But now Dean doesn't know what to do with himself. Charlie's been great about this whole thing so far, and he doesn't want to fuck it all up. Does he change what he's wearing? Does he pick out his favorite pieces from what they just bought and wear them?

He really wants to wear the boy shorts and the matching top. They were so soft and comfortable. He makes a decision and shoves the panties and tops from the bed back into the bags, leaving the ones he really wants to wear out, slipping into them after he takes off the teddy and lacy panties.

Dean settles onto the bed with Charlie's laptop, feeling only slightly awkward, but it's enough awkwardness that his dick is finally softening, which he's completely relieved about.

Charlie had told him her password, so he gets into the OS, opens her browser, finds her bookmarks for movie and TV, and picks out an action flick. Then he wonders if Charlie is into shit like that. He ends up second guessing himself over and over with the movie genres until Charlie walks in.

“I knew you liked that set!” she says as she smiles at him, pointing at the panties.

He looks down at his chest, then back up at Charlie with a grin. “Yeah, they feel really good, and they're also the best at holding in the junk,” he says with a chuckle.

Charlie laughs as she hops onto the bed, then spreads out the food. Dean is surprised by what she's picked. He so used to girls not eating much around him or picking things that look like healthy choices.

She brought ham, cheese, and bread to make sandwiches, a bag of chips, a six-pack of soda, and a bag of bite-sized candy bars.

Dean likes it when a girl doesn't try too hard. He's never had one eat like this in front of him, but he's already excited about not only how good everything looks to him, but also he really likes that Charlie must feel comfortable enough around him to eat like this.

It may put him in the Friends Zone, but he reminds himself that he'll take what he can get, and if this is all he gets of Charlie, he'll take it.

“I want a horror movie,” Charlie drawls as she looks at her laptop, waving her hand at the page he's on like she wants it to go away.

Dean had been in the romantic comedy section, having second guessed himself right out of action, horror, comedies, and independent movie categories.

She looks at him. “Or at the very least something with lots of explosions and guns and violence,” Charlie says with a grin, then waggles her eyebrows at him.

Dean settles back against the head of the bed. He could definitely get used to this.

- - -

If Sam had noticed Dean and Charlie were spending a lot of time together, he hadn't said anything. Dean was kind of freaking out over what to say to Sam if Sam asked or mentioned anything about their relationship or whatever.

Charlie had said he didn't have to tell Sam anything if he didn't want to, but the way it always worked out with them, Sam would be figuring out something was up soon. Keeping secrets never worked out well between them, and the only thing he'd ever successfully kept from Sam had been his gender issues.

He knew he had to say something, and the fact that Sam was still sticking around after everything they'd both done over the years, well, it eased Dean's nerves just a bit. He still felt like his throat was going to spontaneously close off and suffocate him, but he supposed that's better than feeling like he's going to flop over dead of a heart attack.

Sam had been too tired the other night to notice Dean's fingernails had been painted green, and Dean had hid his fingers discretely in his jeans pockets. Charlie had shown off her own painted nails to Sam, but she hadn't said it was Dean who'd painted them for her, and she didn't say anything about Dean's own nails, for which he thanked her later. She gave him her 'duh' face and smacked his arm, then asked if he wanted to go for a walk because she was bored.

Dean was wearing his new wardrobe of panties all the time now. They felt great under his clothes, and he felt a little more like he was becoming what he'd always been meant to be. His dick wasn't even bothering him so much anymore with all of Charlie's encouraging words about being accepting of his body and that it didn't have to define him.

Charlie was a huge help. She was accepting of his feelings on the matter, not pushing when he needed her to back off and being very supportive whenever he wanted to try something new. She gave him advice on things, let him know what she had done and would do in situations, and she listened every time he had questions or concerns or when he just wanted to ramble on for a while.

Dean hadn't meant to, but he'd fallen for Charlie completely. It made him sick to his stomach to think about it, because he knew he was just setting himself up for a world of hurt, but he couldn't help it. She was amazing. Sure, she wasn't flawless, but he could more than handle those flaws, and she sure as hell could handle his.

He hadn't said anything to her about how he felt. He didn't want to ruin what they had. He didn't want to make her feel awkward around him. So he sucked it up. He could do this. She was a great friend, and he'd take what he could get.

- - -

“Sam,” Dean says as they're sitting at the table. Dean thinks he might die. His pulse is racing, his throat is dry, and his palms are sweaty.

He really wants to do this, but he's scared of what could happen. He doesn't want to lose Sam, of course, and he really doesn't think he will over this. What he does see happening in his mind's eye, though, is Sam having a hard time accepting this and the whole thing affecting their relationship.

“Yeah?” Sam replies, not looking up from the book he has spread out on the table.

Dean turns to Charlie, and she gives him a reassuring smile and a nod. They'd talked about it, and she'd offered to be there for him while he and Sam had The Talk if Dean wanted. He did want her to be there.

“Sammy?” Dean says, then waits.

Sam's not ignoring him really, just half listening like they do when they're saying something not horribly important. Pausing like this will let Sam know there's something serious to talk about and he needs Sam's full attention.

Sam looks up from his book, noticing both Dean and Charlie are there. “What's up, guys?” he asks as he pushes the book away from him.

“I want to tell you something,” Dean says, his voice cracking on the last word. He clears his throat, wonders if that heart attack will strike at any moment now.

“Are you okay?” Sam asks, concerned look on his face, straightening up in his seat a little.

“Yeah, yeah, I'm okay,” Dean tells him with a nervous smile. “I just want... I need to tell you something, and I'm, I don't know how you're going to react, so I just –,” Dean starts, but then trails off.

Sam's eyes widen, and he's starting to looked spooked. “You're scaring me, here, Dean. Just blurt it out, dude,” he says.

Dean winces, takes a deep breath. “Okay, so I-I've never felt like I've been in the right body,” Dean starts, then plows on ahead since he's already said this much. “I feel like I should've been born a girl, and Charlie is, well, Charlie has been helping me work this out, but I just wanted you to know because you're my brother and we've learned time and time again that secrets don't work out well for us.”

Dean keeps eye contact with his brother, but it's hard. His chest is burning, and he realizes he's holding his breath. He wants to say he was just kidding and run off to his room. Especially when he sees that Sam's getting mad. Scratch that. Sam's getting pissed off.

“You –,” Sam starts, but cuts himself off as he sighs and looks down at the table. When he looks back up at Dean, Sam's furious. “I can't believe you'd do that. You want to get in Charlie's pants so bad that you fake an 'I'm a chick stuck in a dude's body' because she's a lesbian? That's low, Dean. That's just amazingly low,” Sam says with disgust.

Dean's world takes a jump to the left and his stomach doesn't like it one bit. His mouth is hanging open, but nothing's coming out. It would have hurt less had his brother stabbed him in the back with an actual knife. A dull one.

Dean gets up and hurriedly goes to his room. He's got tunnel vision, and when he slams his door, he can't hear anything but the rushing in his own ears. He feels his eyes burning, but he's so upset he doesn't even think he can cry.

He doesn't want to break something. He doesn't want to fling himself onto his bed and smother his face in a pillow. He doesn't know what he wants, but he knows it isn't pacing back and forth with his hands clenched into fists, but it's what he's doing anyway.

He knows Charlie will come to see if he's okay eventually, but he doesn't even know if he wants to talk to her about this. He won't turn her down if she wants in, but he's in pain, and he wants to calm down. He wants to take the last few minutes of his life back. He should get a redo on this.

It seems like forever that all he hears is the rushing in his ears, but he finally hears Sam talking to him through the door. Dean hadn't locked the door, but he figures Sam is giving him at least the dignity that the closed door allows him.

“Dean, I'm so sorry,” Sam yells through the door. “That was amazingly stupid of me, and I'm really sorry. Please open the door.”

“No,” Dean yells. Sure, it's childish to want to hide, but that had hurt, damn it.

“Dean, I swear I thought you were being an asshole, and I really am sorry,” Sam says, sounding genuinely sorry. “It wasn't until I saw your face that I realized I was the one being an asshole. You really meant what you said, didn't you,” Sam says rather than asks.

Dean doesn't respond. His throat feels tight, and he just wants Sam to leave him alone. He was so stupid for thinking his brother would handle this well. Sam may have accepted a lot of things, but maybe he was more like John than even Dean had even thought he was.

Sam sounds as if he's got his face shoved into the space where the doorjamb and door meet. “I should know you better than that by now, and it was just a knee-jerk reaction,” Sam says through the door. “After I said what I said, as soon as I saw the look on your face, I knew you were trying to tell me the truth, and Dean, I am so sorry. I can't tell you how sorry I am. You were trying to tell me something you've felt since you were a kid, and I threw it in your face because I wasn't thinking straight.”

Dean feels a flare of anger. “I wouldn't do that to Charlie just to get into her pants, Sam,” he yells back at Sam.

Sam sighs. “I know you wouldn't. And if I would've taken a minute to think about it, I wouldn't have ever said that to you,” Sam says, sounding horribly apologetic and like he's already beating himself up over the whole thing.

“Did Charlie threaten to kill you?” Dean asks, almost hoping she did, but at the same time he wants Sam to have come to him on his own.

Sam chuckles. “She didn't have to. As soon as you got up and left I called myself a few choice names and went after you,” he says, sounding very sheepish.

“You deserved whatever names you called yourself, you know,” Dean says, feeling a little mean.

Sam snorts. “I know. I really do. And if you wanna open the door to call me a few more names, that's okay too.”

Dean runs his hand over his face, letting out a big sigh. “The door's open, bitch,” he says.

“Yeah,” Sam drawls, “but can I come in?”

“Yeah,” Dean replies, turning toward the door.

Sam opens the door and shuffles into the doorway. He looks as if he's just kicked a whole box of puppies. He's got his arms out to the side. “I'm sorry,” he says with a wince.

“So you've said,” Dean says, still feeling a bit mean, but he's warming up to Sam's apologies.

Sam looks at the floor, then back up at Dean. He says, “The only problem I have with this whole thing is that you felt you couldn't come to me about this before, and that's probably because you expected something like what just happened, but I mean it, Dean. This doesn't change how I feel about you. You're still my brother,” Sam says, then his nose scrunches up adorably as he thinks about what he just said. “Well, I guess that'd be 'you're still my sister,' if that's what you wanted.”

Dean can't stop the laughter that bubbles out of him. And it has the desired effect on Sam, which is to say Sam looks greatly relieved, and a smile works its way onto Sam's face.

Sam shakes his head, the smile falling. “I mean it,” Sam says, serious and sincere face firmly back in place. “I'm totally okay with this, and whatever you want to do about it is fine with me. I don't say it often enough, but I love you, and all I care about is that you're happy.”

Dean rolls his eyes. “Okay, now you're just taking advantage of the situation to have a chick flick moment. Knock it off,” Dean says with about as much affection as he can shove into his words.

“Yeah, I did, didn't I.” Sam chuckles. “But seriously, Dean. Just let me know what you want. If you want to change your name, change your clothes, change your hair. If you want me to start referring to you as she and her, just tell me. I can't say I won't slip up and say the wrong thing, but I want to make whatever transition you want to make go smoothly.”

Dean flashes a genuine smile at his brother. He has an awesome brother. “Thanks, Sam.”

- - -

“Dee, Charlie!” Sam yells through the door.

Dean jerks awake, jostling Charlie, who lifts her head off of his chest and starts rubbing her eyes. “Yeah?” Dean replies in a scratchy voice.

“I made us all breakfast. Come eat,” Sam says.

Dean groans. Yesterday had been a very long day. He and Sam had been teaching Charlie how to use weapons, specifically knives. She learned quickly and was excited about it all, but it still made for a long day, and they were so tired they'd fallen asleep about a quarter of the way through the first movie they started on Charlie's laptop.

“We're coming,” Dean grumbles.

Charlie whines and shoves her face into the space between Dean's chest and the bed, which makes Dean chuckle.

“C'mon, Charlie. Sam's getting really good at cooking, and he likes trying out new stuff. It'll be worth it,” Dean promises.

“Fine,” Charlie growls, then pulls herself out of her Dean cave.

By the time they get to the kitchen, they're both more awake and Dean's stomach is growling. It smells wonderful. Dean and Charlie sit down at the table and grin at each other after getting an eyeful of Sam in an apron, which never fails to amuse the both of them.

“I tried something new, so let me know what you think,” Sam says as he sets down three plates, then takes a seat at the table.

“Ugh, this isn't some sort of veggie shit, is it?” Dean grumbles as he tilts his head to the side, looking for hidden bean sprouts or something else that will jump out and attack him with its vegetable goodness.

Sam chuckles. “Nope. It does have avocados and tomatoes and corn, but those are real eggs. It's extra thin Indian flat bread with a little cheese, corn, black beans, straight up eggs, and the stuff on top is kinda like a sweet salsa,” Sam says as he points out each item. “There's avocado, onions, and tomato in there.”

“It looks wonderful, Sam,” Charlie says as she digs in.

Dean's unsure. There are eggs, and he supposes the cheese does attempt to make up for the lack of bacon, but the whole thing looks too pretty to be awesomely tasty. Dean watches Charlie take a bite and the moan that comes from her makes Dean rethink his initial assessment.

“Sam! This is so good!” Charlie says as she gets another forkful.

Sam turns to Dean and raises an eyebrow. “There. Charlie has taste tested it for anything poisonous. You're free to try it now,” Sam snarks.

“Hmm, we'll see,” Dean says, then takes a bite.

The flavor mix might have seemed a little odd to look at, but once they're in his mouth, Dean thinks it's one of his new favorite breakfasts. He moans almost as loud as Charlie had.

“That's it,” Dean says through his mouthful of food, “we're chaining you to the stove and never letting you leave the kitchen.”

Sam lets out a bark of laughter. “I'm glad you like it,” Sam says with a big smile.

The three of them don't talk for a while as they enjoy their breakfast, but soon Dean notices that Sam's throwing sidelong glances at him, so when he's all but licked his plate clean, he turns to Sam.

“Spit it out,” Dean says.

Sam's eyes widen, and he swallows his last bite. He seems to think about it for a moment, then sighs. “It's a personal question that I have absolutely no business asking, but...,” Sam says with a grimace.

“Go for it,” Dean says.

Sam's mouth opens, but nothing comes out. Then he tries again, seems as if he's thinking carefully about how to say it. “You don't have to answer if you don't want to. And again, this is none of my business,” he says, but Dean's impatient hand motions make Sam smile. “Do you hate the fact that you have a dick? Would you want that to change or are you okay with your body? Did you want to have a sex change when you were a kid? Do you want to now? It's just you'd like to do some things more on the feminine side or, well, because Charlie's been calling you Dee and you get a smile on your face when I call you Dee, and I saw bags in your room from a lingerie store, and I didn't want to pry, but you and Charlie have been spending a lot of time together, and I just don't want to step on toes or offend you, but –.”

Dean starts waving his hands around to stop Sam before he dies of lack of oxygen to the brain from all the babbling. “Dude. Chill,” Dean says.

Sam chuckles, then relaxes. “Sorry.”

Dean turns so that he's facing Sam head on. “When I was a teenager, yes, I wanted to have a sex change operation, but then I researched it. It's still not a very commonplace surgery, but back then it was even less common, and I read about how you can lose sensation in parts or all of your sex organs, and that right there stopped any ideas I had about getting the surgery.”

“Oh, yeah, damn. I guess that would be a big consideration,” Sam says with a look of alarm on his face.

“Hell, yeah,” Dean says with a smile. “And drugs mess with your hormones, which fuck with your sex life, in case you were wondering. Oh, and to answer your question about my dick, I don't hate it in the sense that it's responsible for orgasms, and anything that gives me orgasms is very important in my book,” he says with a grin. “If I was able to, by some sort of miracle or spell or what-the-hell ever, just change over to a female body, complete and as natural as if I was born that way, then yes, I'd do it in a heartbeat. But as far as anything less than that, I'm not going to take the chance that it'll fuck with my sex life.”

“Gotcha,” Sam says as he nods, then looks down at the table as if taking in everything he's just heard.

“Dicks are annoying,” Dean blurts.

Sam laughs hard at that. “I suppose that's true, even though I really, really like mine.”

Dean winces. “They're not pretty, they're messy, they announce your arousal to the world,” Dean lists with a disgusted look on his face, then he grins and waggles his eyebrows, “and they don't taste nearly as good as pussy.”

Charlie giggles and nods enthusiastically. “I concur!”

Sam laughs again. “Your arguments are all valid and completely true.”

“Charlie's helping,” Dean says as he throws a glance at her. Charlie gives him a sweet smile. “Before her, my dick was a necessary annoyance. One that I wouldn't give up, of course, but I was embarrassed and I didn't even like the way I looked in clothes because of it and because of the lack of tits. She's helped me with accepting what I've got even if it's not what I'd like to have or what I think I should've had from the start.”

“Charlie's smart, “ Sam stage whispers. “You should listen to her.”

“I am smart,” Charlie says with a smile and a nod. “You should totally listen to me.”

Sam chuckles, then turns to Dean again. “Thanks for letting me ask awkward questions. I don't want to make you uncomfortable, but I kinda feel like any information I can get out of you will make it so there's less confusion and room for me saying or doing something monumentally stupid in the future.”

“Not a problem, Sammy. If you do ask something I don't feel like answering, I'll tell you,” Dean says.

“Okay, that seems fair,” Sam says with a relieved look on his face. “Then I have another question.”

“Okay,” Dean says.

“Are you attracted to women or men? It's not because I have a problem with it either way, but I've seen you go after a lot of chicks over the years, and you seem to really, really like chicks, but I also know that just because you feel you should have been born a female, that doesn't mean automatically you'd be a heterosexual female, and your comment before about dicks being ugly and messy gave me some idea of your feelings on the matter, so I... and I'll stop talking now, sorry,” Sam finishes with a blush to his cheeks.

Dean chuckles. His brother is adorable when he's trying to be supportive. “I like women. A lot. And dicks are not something I'm interested in. But it's more than just that. I've never been attracted to a male personality, never gotten along with one other than you, and Cas doesn't count because of the whole angel thing, so yes, I'd definitely say I was a lesbian,” Dean says.

“And no,” Sam says, “I'm not going to say you should just keep your dick if you like women anyway. I'm not a total asshole.”

Charlie laughs. “I knew there was a reason I liked you, Sam Winchester,” she says with a smile.

“Why, thank you, Charlie,” Sam says, beaming at her with dimples in full effect. “And Dean, I just want you to know that you can go as far as you want with all this, and I'm not going to give you a hard time besides some necessary little brother-like teasing. You do what makes you happy.”

Dean feels his eyes burn, his throat gets a little tight, and his breath catches in his chest. “Thanks, Sammy,” he manages to say without crying at his brother.

“Thank you for the wonderful breakfast, Sam,” Charlie says as she gets up and starts gathering the dishes. “Since you made breakfast, I'm doing the dishes, then you guys can teach me how to use an easily-concealed knife.”

“You got it,” Dean says as he gets up from the table. “I'll go pick out a few knives. Sam, can you get the floor mats set out?”

“Yup,” Sam says as he gets up, “and thanks for doing the dishes.”

“No problem,” Charlie says, already filling the sink with soapy water.

- - -

“I'm sorry! Fuck!” Dean yells as he pulls away from Charlie. “I'm really sorry!” he says as he sits on the mat, panting and berating himself internally.

Charlie rolls into a sitting position and sighs. “Dee, it's okay. We're wrestling all over the ground, you're getting stimulated, adrenaline's pumping, and I really don't mind,” she says sincerely.

Sam stays quiet where he sits against the wall, cleaning the guns and discretely watching them.

“I fucking hate it,” Dean growls. “And why aren't you more upset about this? You hate dick, and here I am stabbing you with it every time we get close because you're so fucking hot and, oh fuck, I really do want to get in your pants.” Dean shoves his face into his hands.

Charlie huffs indelicately. “If you're going to be a woman, you really need to knock off this stupid shit of listening like a man,” Charlie says.

Dean startles, his hands coming away from his face so he can look at Charlie. He hears Sam snort, but Sam doesn't comment.

“Huh?” Dean asks stupidly.

“All that shit I said about trying to get you to accept the body you're in if physical transitioning isn't what you want to do right now, everything I said about how I care about what's on the inside, about how, hey, isn't it cool that you feel the same way as me about guys versus girls, and, holy shit, Dee, you didn't get it even when I was grabbing your dick to get it positioned in the panties we bought and were trying on together!” Charlie babbles with a shocked look on her face.

Dean hears Sam choke after Charlie's last line, but he's too shocked himself over what Charlie's saying to tease Sam about it. Dean knows it's the first Sam's heard that he and Charlie had tried on lingerie together.

“You didn't get any of this?” Charlie nearly squeals. “You're so stuck on me being a lesbian even though I've been flirting with you almost this whole time and practically screaming in your face that I wished people would look beyond physical bodies to see the real person that you didn't see I was attracted to you as a person, and that I don't give a shit about you having a dick beside the fact that you're upset about it?”

“Uhm, I –,” Dean splutters.

Charlie gets to her hands and knees, crawls over to Dean, then kisses him. Dean's head is swimming, not only because this is really fucking happening, but because he really had been so stuck on Charlie not being into him physically that he'd not even considered it a possibility.

He'd been so stupid. He'd even explained to Sam, with Charlie sitting right there, that Dean himself was attracted to girls, not boys his whole life because he just never connected with male brains and personalities.

Charlie continues to kiss him, probably knowing he's working this all out in his head, though she probably doesn't realize he's having a harder time working through it because Charlie's such a great kisser.

She shoves her tongue into his mouth and he moans. It's been so long since he's had any kind of sexual contact, and being so close to Charlie these past few weeks, trying on lingerie with her, lying in bed and watching movies with her, it's been kind of a slow torture.

Dean lets her control the kiss, and he shivers when she grabs his face with her hands. She's damn near eating him alive, and he loves it. She finally pulls back and looks him in the eye.

He lets out a nervous chuckle and feels his eyes well up with tears. He still feels stupid about this whole thing, but he also feels very grateful that something he's dreamed about, wished for, fantasized about for weeks now is not only a possibility, but it's actually happening.

He thinks about when he first met Charlie, how he felt an attraction even then, but how he'd been careful to keep a bit of distance after finding out she was a lesbian. But he'd still wanted her. And a part of him had wanted her even more knowing that she was a lesbian, because there was a small niggling hope in the back of his mind that she'd be open to his seemingly overwhelming mountain of issues, open to what she was now offering him.

Dean tries to blink away the tears, but instead a few fall down his cheeks. He smiles at Charlie as she wipes them away. Dean glances over to where Sam had been sitting, happy to see Sam has left. His brother is awesome.

“You were flirting with me?” Dean asks, scrunching up his nose.

Charlie snorts. “Well, I do tend to be dorky, and I've been accused of being cute whether I'm flirting or not, but yeah, I haven't been blurting out sexual innuendos around Sam, and I certainly haven't tried on lingerie with him,” Charlie says.

Dean chuckles. “See, that's what threw me. I thought the two of you went and got panties in Sasquatch's size and tried them on together. If I would've known it was just for me, I'd have clued in a little faster.”

“Are you done being oblivious now?” Charlie asks sweetly.

“God, I hope so,” Dean says, rolling his eyes.

“Yay!” Charlie squeals as she does a little body wiggle of joy, making Dean chuckle. “And I just want you to know that I'm okay with whatever.”

“Uhm, whatever what?” Dean asks with a raised eyebrow.

Charlie giggles. “Communication; I has it,” she says, then snorts at herself. “What I'm trying to say is that I want you to know as far as a relationship and-slash-or anything sexually you want to do with me, I'm totally up for it.”

Dean sees the excitement on her face, yet he's still not quite sure what all she's offering him. “Okay, now don't hit me or anything, because I really did listen to your little speech about seeing the person within, but, uhm, I do still have a dick,” Dean says, the bridge of his nose scrunched up.

“I'm not going to hit you,” she says, then adds with a leer, “unless you're into that.”

Dean really digs the leer, and his dick twitches at the thought of Charlie finding him leer-worthy. “I might be,” he flirts back.

“Okay, just so we're on the same page, here,” she says, “I really, really like pussy, but when it comes to anything beside a quickie with some hot chick I just met, it's all about brains, personality, sense of humor, and all that other good stuff.”

“Have you ever been with a guy?” Dean asks.

“Yes,” she says.

Dean is shocked. “Okay, I hadn't expected that, especially after your reaction to that guard. You couldn't even flirt with him,” he says, the sentence somehow turning into a question.

“You didn't see the guy,” Charlie says with a frown.

“I thought you just said you don't go by looks so much,” Dean says.

“That's true, but initially there has to be some judging of a book by its cover,” Charlie says, throwing her hands up. “He was definitely totally male. The maleness was just radiating from him like a giant neon sign, and it's an instant turn-off for me.”

“Oh, well, that does make sense, because I'm not really attracted sexually to overly butch lesbians,” Dean says reasonably.

“There you go!” Charlie says with a grin. “The guys that I've been with –,” Charlie starts.

“Guys, plural?” Dean interrupts with a raised eyebrow.

She smacks his arm. “Yes, plural,” she says, faking annoyance. “The guys plural that I've been with have had that same something about them that attracts me to them. One guy was bisexual, and while he really didn't have gender issues about himself, his entire personality and way of life, well, I just meshed well with him. We dated for a while, but it didn't work out, so we went our separate ways.”

“And when you say you were with him...,” Dean prompts.

“I don't have any video or pictures,” Charlie teases him with a really disappointed look and a sympathetic shrug.

“Dork,” Dean says as he chuckles.

“Another guy that I went out with for a while couldn't decide if he wanted to be called he or she,” Charlie says, and Dean notices that Charlie doesn't seem like that idea was odd or an inconvenience, rather she says it like she's telling Dean the weather. “Remmy was just Remmy. He had gotten breast implants a few years before we started dating, which I had fun with,” Charlie says with a lascivious grin, “but he was completely on board with keeping his dick and balls. He dressed in women's clothes sometimes and men's clothes other times. He liked to say he dressed to fit his mood.”

“That's actually refreshingly awesome sounding. Cool that he was that comfortable with himself and you let him do what he felt like doing,” Dean says, feeling chills run down his spine. A big part of him is jealous of Remmy, but another part wonders just how much he would have been like Remmy even if he had thought it would have been acceptable.

“It would've been really selfish of me to try and keep him from doing what he felt like doing,” Charlie says. “The thought never occurred to me. Remmy was one of the happiest people I've ever met, and I hope he never lets anybody make him feel like he can't be who he wants to be.”

Dean's eyes burn again, but he blinks away the emotion. What's done is done, and even though he let others dictate how he should live before, Charlie and Sam being so great about all this was opening up so many new options to Dean, and he was very grateful.

“I've been with a few more guys than that, but I just thought you might like to hear how much I don't have a problem with you or what you want out of life,” Charlie says with a little smile that makes her eyes look so very warm and welcoming, drawing Dean in.

Dean winces. “After seeing how well you've taken this, and after seeing how well Sam's doing with it after that first knee jerk reaction and misunderstanding, I think I'm probably going to be the one that has more difficulty with this.”

Charlie grabs both sides of Dean's neck with her hands, pulls him in for a quick but firm kiss, then pulls back to look him in the eye. “Sam and I have talked about it,” Charlie says.

Just as Dean tenses, he sees the look in Charlie's eyes, one that tells him she knows he's upset they talked about him when he wasn't there, but to just hear her out, calm down, so he does, nodding at her, and she gives him a little smile when she feels him relax.

“Sam loves you so much,” Charlie starts.

Dean feels his breath catch in his chest. Not that he didn't know his brother loves him, but the conviction Charlie has when she says it takes Dean's breath away, like Sam's love for him was so significant and noteworthy that Charlie was moved.

“He wants you to be happy. That's all he's ever wanted when he hasn't had his head up his own ass, which admittedly has been fairly often,” Charlie says with a chuckle.

Dean snorts. Yeah, that sounds like something Sam would say, and it's completely true. Dean has always loved Sam, even when he knew Sam had his head up his ass, and even when it hurt to love Sam.

“He's a little hurt that you didn't say something to him over the years, especially given how close you guys are,” Charlie says.

When Dean opens his mouth to speak, Charlie puts a finger over his lips. He huffs, but he doesn't speak, so she takes her finger away.

“He knows it's a big thing,” Charlie says, “and he knows that your dad probably wasn't the type to handle it well. But I think you should talk it out with Sam because he's got it in his head that he gave off anti-tolerance vibes over the years or said things that made you think you couldn't tell him about something so significant in your life. I told him I wasn't sure because I didn't grow up with you guys. Take time if you need it to think about it, but I really think you should talk with him about it.”

Dean nods. “I will. And thanks for talking to him.”

Charlie smiles. “You should totally thank me, and you should definitely show me your appreciation in fun and interesting ways,” Charlie says with an eyebrow waggle.

Dean chuckles. “I can so do that,” he says as he laces his fingers through Charlie's, holding her hand.

“I'm sure Sam will tell you in more detail, but he's more open to things like this than I think you knew,” Charlie says.

“I know Sam well enough that I have no problem believing you,” Dean says, “but I was purposely blind about it because I was too scared he'd not be okay with it.”

“He understands that you'd be scared. Just talk to him,” Charlie says again.

“Yes, ma'am,” Dean says.

“Mmm, “ma'am.” I think I like that,” Charlie says with a shiver.

Dean feels his dick twitch again at Charlie's reaction. Now that he knows Charlie's okay with all of this and is on board, Dean doesn't have to hide how he feels about her. It feels great to be able to flush with arousal and not worry she's going to be offended or upset.

“And as far as me,” she says with a grin as she grabs him by the front of his shirt, pulling him closer to her, their noses inches apart. “I want to do lots of fun stuff with you.”

“Mmm,” Dean moans as his eyes fall closed.

“I get the feeling you like a sexually aggressive woman, even though from what I gather, your previous long-ish-term girlfriends weren't all that aggressive,” Charlie says, then licks his lips.

Dean gasps at the tease of her tongue. “You heard that from Sam, right? The thing about the girls I liked being submissive and pushovers?” then leans in to kiss Charlie.

Charlie pulls back suddenly, leaving Dean questing after her lips. “Sam's wrong?” she asks with a grin.

Dean whines at the missed opportunity to kiss Charlie, then leans in anyway and kisses the side of her mouth. “Sam saw both Cassie and Lisa in situations where they were scared for their lives and their families. Neither of them backed down or ran away from those situations, but Sam saw them at their least confident.”

Charlie grins. “I see,” she drawls. “That works perfectly with all my evil plans for what I intend to do to you,” Charlie says, then lets out an evil overlord laugh that both impresses Dean and makes him laugh along with her.

Dean ducks his head, then looks up at Charlie. “I can get aggressive, and I like making my partner very happy in bed, but yeah, I like a woman who knows what she wants and takes it.”

Charlie dives down and kisses Dean with a fierceness that makes him groan into the kiss. She wraps one hand around the back of his neck, the other around his back as she climbs into his lap and opens his mouth with her tongue.

Dean's hands flutter at Charlie's sides for a moment before he wraps his arms around her. She starts grinding down on his crotch, her breasts rubbing against his chest as it feels like she's trying to get herself off on the friction through their clothes alone.

Charlie moves her right leg to be in between Dean's legs so that she's riding Dean's left upper thigh, then starts grinding down on him, getting herself in a position that must feel great by the way she sticks to that spot and works down hard on him. Dean's getting friction on his dick from how enthusiastically Charlie is grinding on him.

“This all right with you?” Charlie asks, voice breathless and scratchy in a way that makes Dean's whole body tighten in a delicious way.

“Yeah, fuck, yes,” Dean mumbles as he lets his head fall to Charlie's shoulder, licks her neck, then moans as he feels her shudder against him.

“I've been waiting so impatiently for you to catch a clue, Dee,” Charlie gasps, then scratches her nails over Dean's scalp.

The use of this new name Charlie has given him excites him. He could have it. It could be his name. Charlie uses it. Sam uses it, only having slipped a couple of times and called him Dean, then corrected himself without fanfare.

Dean wants it. He wants to be Dee. He wants to have awesome tits. He wants to have a pretty little pussy, but he wants to be what Charlie wants, wants this idea of being what he's hoped for so long, even if it's not complete, not physical.

He'll still be stuck with a dick, but he knows life isn't fair. He learned that long ago. But he can have this. He's happy for this. He's thrilled Charlie was the one to give this to him, that Sam was willing to give this to him.

And she's right here, right in his arms, grinding against him so sweetly it's taking his breath away. She's so lost in arousal that her eyes are falling closed seemingly against her will, because every time it appears she remembers, she opens her beautiful green eyes to watch Dean again. To watch Dee again.

Dean holds Charlie tighter, yanks her against him, and Charlie lets out a squeak. Dean's so hard it hurts, and he's so close to coming he's almost embarrassed.

“You gonna come in your pants for me, Dee?” Charlie whispers in his ear.

Charlie's voice is so sultry, so unbelievably wasted on arousal that Dean whimpers, shoves his face into the space between her neck and shoulder and comes so hard he grits his teeth and growls, “Charlie, fuck, Charlie!”

“Oh, my god, y-you, fuck, you really came in your pants,” Charlie nearly whines, straining against Dean, sounding so desperate, so fucking turned on and damn near mindless. “Dee!” Charlie yelps as she comes, jerking hard against Dean.

Dean holds her firmly, but not so tight as to stop her from moving however she wants to move. Just hard enough that every jerk and wave her body makes goes straight through him. As the waves wash through her, the grinding gets slower, but she's still moving, still using his body as she pants into his hair, nails gripping his shoulders, and Dean hopes they leave marks on his skin.

Charlie finally slows to a stop and drops her weight on Dean, totally spent and enjoying the afterglow. Dean happily holds her up, then realizes there's a mat beneath them, and he doesn't have to do all the work.

Charlie squeaks as Dean lets himself fall backward. She doesn't seem surprised, but more as if it's a squeak of “yes, that was a good idea,” and then she wriggles a little until she's comfortable sprawled all over Dean.

Charlie turns her head so that Dean can feel Charlie's breath ghosting over his right ear and neck. “I made you come in your jeans, Dee,” Charlie says in one of the sexiest afterglow voices Dean's ever heard, like she's completely pleased with herself for having had that effect on Dean.

“Yes, you did,” Dean says with a lazy chuckle.

“'Cuz I'm just that hot, huh?” she asks as she lets her fingers trail over his left nipple and chest.

Dean chuckles again at Charlie's adorableness. “Yes, you're just that hot. And you seemed to find me coming in my pants a turn on, so I'll try not to be embarrassed.”

“Hell, no, don't be embarrassed,” Charlie groans as she tweaks his nipple as if in punishment for ever having considered being embarrassed. “Are you embarrassed when a girl comes just from getting fingered before your tongue or anything else ever even touches her?”

“Mmm, no,” Dean admits, his eyes falling closed.

“So imagine how sexy I feel having made you get those pretty panties all dirty with your spunk,” she whispers in his ear.

“Oh, fuck,” Dean groans at the dirty talk. He hadn't forgotten he was wearing a pair of pink polka dot panties with a little pink bow at the front. It seems Charlie hadn't forgotten either.

“I plan on sharing many, many more orgasms with you,” Charlie mumbles as she snuggles into Dean as if she's going to fall asleep right here on the mat. “That all right with you?”

“I have no problem with that plan,” Dean says, caring less and less that he's lying on a mat and not in bed.

- - -

Next: Part 2

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January 2025

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