Chapter Text
Dean likes strong women.
The demure or coquettish are not his cup of tea. He likes a woman who knows what she wants. A woman who knows what she likes and demands it. He loves it when a woman grabs his hand and puts it exactly where she wants it to be, and will even direct its motion if he's not quick enough to figure it out. A woman can be introverted, standoffish, or even downright taciturn socially, so long as she's not shy in bed, as far as Dean's concerned. Blushing virgins need not apply, because Dean doesn't have time to muddle through vague communications.
Worst of all, are women who make him feel like his sexual efforts are only for his own benefit. Nothing turns him off quicker than thinking his partner's not having a good time. Plus, a strong sexually aware woman never seems to get troubled by the aftermath, they know how to have a good time, and can see their night together for what it is: fun. Hell, he's even had women (politely) kick him out when the fun was over. "Well done, now see yourself out".
Yeah, Dean likes strong women.
If Dean was more self-aware he'd probably realize that what he really likes is absolute clarity that he is wanted and desired. All the effort he's put into his sexual prowess and technique was subconsciously done to elicit this reaction. Dean wants to be wanted, with no room for miscommunication.
Of course, liking strong, sexually aware women, carries a correlation that they tend to also be sexually adventurous as well. There's been many adventures Dean's followed his partners into that wouldn't have occurred to him on his own. Some results better than others, but Dean is always happy to follow a lady's lead.
Peggy was a revelation. Of course, her name wasn't actually Peggy, that was just what Dean called her in his head afterwards. Introductions happened at the beginning of a seduction, and it was only afterwards you'd know if the name was worth remembering. By then, though, it was usually a bit rude to ask.
He thought of her as Peggy because she was really into pegging. This was something she'd had to explain to Dean, complete with the visual aid of her favorite strap-on. Dean had to admit, that when she'd opened an *entire chest of sex toys* he felt like he'd gotten in way over his head. She hadn't given any previous sign she was so kinky, Dean had picked her up in a *library* for fucks sake, while his brother had been doing research. His panic must have been obvious, because she turned gentle and knowing.
"Tell you what, how about, I finger you while I blow you and you can stop me at any time. I guarantee you won't, though. I know what I'm doing, and I'm really good at it." She smirked at the end, like a dare.
With inhibitions lowered by arousal and a light buzz, Dean took her up on that dare, and, holy crap, was she right. She was as skilled in her sexual artform as Dean was in his. If Dean had had the power to canonize the petite librarian, he would have dubbed her the patron saint of the male g-spot.
When she'd finished showing him the celestial spheres and the divinity of what a male orgasm had the potential to be, she lustfully crawled up to his side. Her voice was a throaty, blissed out wreck as she muttered in his ear.
"God, I love that feeling, being inside a man. When a woman comes, her pussy clamps down and draws up, but when a man comes..." she grabbed his hand and wrapped her fist around his finger. She drummed her fingers in quick succession to demonstrate the muscle ripples that she had felt when he came. "Mmm... it makes me wish I actually had a dick to fuck you with."
In post-orgasmic bliss, Dean couldn't find it in himself to be reactive to her comment. Plus, he was already distracted as she brought his fingers into her mouth to slick them with her saliva. A move which quickly seemed redundant when she pulled his hand down to the sopping heat between her legs. Dean was grateful she was happy to be finished off this way. He desperately wanted to please her in turn, but he was goddamned wrecked by the orgasm she'd given him. He settled for fingering her while he whispered in her ear, dirty truthful things, like how he'd never done that before and she blew his fucking mind.
Yeah, Peggy had been an absolute revelation, and it was a regret Dean would kick himself over that he hadn't gotten her actual name or phone number. It was certainly better than his usual type of regret, Dean had to admit, but, in all his further exploration of anal play, he never again found a woman that skilled. It certainly wasn't the same when he tried it on his own.
On the rare occasions he had time and privacy to try things out for himself, he internally thought of it as praying to saint Peggy, patron saint of the male g-spot. He had to admit that the blasphemy of it was a definite plus.