Chapter Text
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Dean had never been in love.
Ever.
Not when he was with Cassie, sweet Cassie, an almost 18-year-old college student from Missouri. She fell in love with the almost 15-year-old Dean, who accompanied his father on his business travels during his summer vacation that year.
John Winchester was selling insurance all over the country and stayed for a couple of weeks in Cape Girardeau, where, if he wasn't busy and didn't need to work on a job, he went on lengthy hunting trips with Cassie's father, Martin, who was a Marine friend of Dean's dad.
Meanwhile, Dean had nothing else to do but wait.
When Cassie arrived during her summer vacation, it gradually became nicer. They had liked each other from the start. She was interested in the books Dean read, and let him discover the authors she liked. She liked his music very much, and he started being interested in hers. She showed him the beach. They had long, detailed conversations. She told him a lot about her father's PTSD, and Dean recognized some things about John.
Then she told him that she had fallen in love with him.
From that moment on, she wanted more.
Something else.
Something … Different.
It started with kisses here and some hugs there, which felt comforting and warm at the beginning, but this phase didn't last long. Without even thinking too deeply, Dean also joined everything else that followed.
Because she liked it so much, and he would have done anything to comfort her. Well, almost anything.
If it had been up to Dean, all these new things would not necessarily have been happening. It was alright to do what they did, and he didn't say no. Not to most of it in any case.
He also liked her body, which felt warm and soft under his fingers.
He liked her scent.
He liked it when she bent over and whispered in his ear, where he could touch her.
He liked the instructions she gave him. Without this information he wouldn't have a clue, no imagination, what else he should have done, or what she would have expected from him.
Touching her became a hobby that summer, and, while his father was working on a job, to his own surprise, Dean became more and more a lover.
So was this what was expected of him?
If it were up to him, he could have just listened to his music. His mixtape, which he picked up from the Impala and brought to Cassie's home. If only he had not played Whole Lotta Love and if Cassie hadn't made him pay attention to the lyric line 'I wanna be your Back door man'. Did not everything start with that? Did he unknowingly give her a false impression about himself?
Well, Dean had already stumbled across this line. This one line he never really understood from the beginning, and his father couldn't, or wouldn't explain it to him.
"You'll figure that out on your own” were his words. “You'll figure that out on your own," was, by the way, John's standard answer to most of the questions Dean had.
Anyway, Dean had wondered the whole time why Robert Plant was speaking of the rear entrance of his girlfriend's house. Why was that so important to mention it in a song?
So, since that summer, Dean has had, as he sees it, a mission. He did find something he was actually good at. He became a lover. Someone who knew stuff. Nevertheless, someone who didn't 'jump off the cliff,'. He didn't do that with Cassie, either to the 'back door' or to the 'front door', and he didn't want to start doing one of these. But he was also a lover who didn't put any pressure on the girls. On the contrary, he was very pleased with everything which made her satisfied.
Dean also learned from Cassie what flirting meant, and how to unmistakably recognize that it was exactly that. Since Dean was with Cassie, he knew about all these things.
Following orders was something he was always good at, and that's exactly what he did.
When the summer was over, he helped Carmen from his year have her first orgasm from a boy. She knew exactly what she wanted, and Dean was willingly giving it to her.
He kinda did it with Ronda, who asked him to put her underwear on, which was confusing at the beginning but finally not as awkward as he originally thought, and he kinda did it with Robin, whom he met on Sonny's farm, the next summer, when Sam made it to science camp and Dean didn't even try to reach his own kind of camp.
With Sonny, he had learned to get up so early that it hurt, to feed chickens, to take cows to pasture and milk them in the evening, and to look after machines. All the hard work that a farmer did every day to make ends meet. He also learned to play the guitar, or at least he tried.
Cassie taught Dean to read signals. To know what it meant if she licked her lips when she was looking at him, and then this small smile, and afterward, to brush her hair behind her ear.
“What do you want me to do?” he asked Robin while looking at her. He looked at her properly, licked his upper lip once, and then bit his own lower lip lightly. Now she knew he wasn't talking about the guitar.
Dean knew exactly why he did all this. And why he also enjoyed it so much. It felt so good to please 'her'. When she moaned under his hands. When he pressed the right buttons that felt so good for her and also when 'she' wasn't ready for real sex, which was secretly always Dean's unspoken hope, because proving to her how much he liked it was difficult, to say the least. He wanted to do something for her. For her alone, to make her happy.
Helping a girl have an orgasm felt so good at first. Besides, he could be gentle. No, he had to be. He could take as much time with her as he needed. He could lick her, massage her, lightly bite her nipples, and breasts were no problem at all for Dean. Breasts were a 'safe space' on the way to her mouth. Soft skin under his lips that, when he gave his full attention to them, made her moan with rapture.
Sometimes, he could massage her bottom, sliding a finger lightly inside her every now and then. With a little lubricant, many things went easier. He had learned that by now, and his murmuring, "Oh, that's all right, maybe next time," after she came, and he didn't again, uttered with a slight undertone of disappointment, always seemed believable.
In truth, he was not disappointed. He was always relieved. It had taken him a while to admit it to himself. He didn't really want to have sex. Not yet. Not at all. At least, not for now. He wanted to bring a girl to orgasm. He did. He liked that, but coming inside her himself? Just the idea of doing something like that confused Dean.
And it also scared him a little.
Masturbation never crossed Dean's mind. Why should he have done that? Too often recently, he already had a hard on when he woke up and needed a while and very quiet thoughts, a lot of very quiet thoughts, to get out of bed at all. Recently, he also seemed to have an orgasm during sleep, and his sheets were sticky and smelly, and he was ashamed of himself.
If the worst happened, he collected his sheets and underwear and crept into the basement, where he put the fast washing program on and waited down there to finish.
Sometimes he made it before Sammy and his mom woke up; fortunately, he hardly got to see his father in the morning, if he was home. Then he hung his damp laundry on the clothesline and crept into the kitchen.
Just like this morning.
“Hey Dean,” Sam greeted him and poured him a glass of orange juice. Dean was no good without a first sip of orange juice. Everyone in the house knew that. Even when it was mixed with water. His mother slightly smiled, but she didn't judge. That's what Dean liked about her.
She knew, of course, where he just came from and what he did down there, but she didn't say a word.
Sam, fortunately, had no idea.
“Hey Sammy,” Dean said, and he sat down next to his younger brother at the kitchen counter. He stroked Sam's hair once and pressed him lightly against him, then took one of the slices of toast that their mother had already toasted, smeared it thickly with butter and put a dab of honey on top.
“You could eat something different, darling,” his mother said, "but always this sweet stuff.”
“Why change something if it's working?” He replied, winking at her.
Holy Shit!
Too late, Dean recognized that he had just used his flirty wink with his mother.
There was no excuse for that!
Fine, he was not really awake yet; half the night he had once again lain awake, but even if he was very tired and more than clueless, he wasn't supposed to cross certain boundaries.
Dean had to bring himself under control. But first, he had to wake up.
In all innocence, he asked his mother about a cup of coffee. Just one. With milk and sugar. That was something new, wasn't it? And he was old enough.
Speaking of old enough: how could he even think of leaving school without graduating and then still assume that his parents would approve? But he couldn’t go to school for another year either.
He didn't fit in there. That was no longer his world. He wasn't a nerd, wasn't a stoner, wasn't somebody who was walking around with a skateboard under his arm, and he definitely wasn't a sports person. And absolutely not at all did he want to be one of those guys who had a girlfriend. That was the last thing he needed.
Dean felt more and more how the ice he was walking on, no matter how skilled he was with his fingers or with his tongue, became thinner and thinner.
He knew what was expected from him. He knew that Pamela, after he licked her last week, wouldn't let go. He already told her she wasn't a bitch, and he wouldn't talk with his friends (what friends?) about her. But she liked him. Well, certain parts of him.
Point was: She had her mind set on giving him a blowjob, and no matter what he did or how much he tried to distract from his body, when he gave her what she wanted, sooner or later she always came back to his penis.
But there, he didn't want anybody touching him. Nobody. How could he say this to her?
And she wasn't the only one. Ronda contacted him recently.
He had also tried to make it clear to her in the most diplomatic way possible, that sex just wasn't his thing. So: sex in which his body was involved.
Everything else was a hobby.
He realized how all this followed him into his daily life. Just how often he had had to change the sheets in the last few weeks! He wondered if he, a horrible idea, came loudly in his sleep, and his parents or, good God, poor Sammy, possibly noticed anything.
Sometimes he wished he would be different. That he could be normal. Like everyone else. He thought that maybe he liked boys more, which means being gay, but, no, imagining having sex with a boy and really doing it seemed to him as false as being with girls.
But making out with a boy, kissing him, touching him, all this, Dean, on the other hand, could already imagine. He hadn't made much use of the lube, and something told him that some guys, those who were into that sort of thing, would have appreciated his curiosity at the back door.
More than the few girls so far, anyway. But to follow this path would have unnecessarily damaged his reputation at Rome High School and only caused confusion, so he paid it no further attention.
So be it. For Dean, at least, it wouldn't have made any difference.
Sex was not his thing.
He just didn't want to 'come'. He didn't want to 'let go', didn't want to 'break a dam', didn't want to collapse moaning over her or him, and the idea of sweating while doing it disgusted him.
Making out was simply a hobby for him, but not a very fun one by now, and he did it out of pure habit.
If it had been up to him, he would have liked to just listen to the end of the mixtape. He would have finished his tea, kissed Cassie on the forehead, and said good night. And he wouldn't have fallen out of bed with her on his arm first, smooching, which she thought was funny, but he didn't. No, honestly, he didn't.
So, no sex for Dean.
But unfortunately, that meant he had to leave school without graduating.
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