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As some may know, I’m a fan of Sheila O'Malley’s reviews. In them she many times described Jensen Ackles, and by proxy - Dean Winchester - as an “Erotic Muse” - a la “Old Hollywood”. And I think this trans-sipping of erotic quality is crucial in the understanding of this illusive character. It was also stated and talked over many times before - Dean’s charisma, his “pull”. Be he covered in blood and grime, wearing a dashing, flawless tux or utterly wasted from over-consumption of pills and alcohol - he is still, strangely enough - very attractive.
Of course, it is all debatable, and tastes may vary, but going with that assumption - it would be, in my opinion the numero uno step of the ladder that leads to his promiscuous behavior and his attitude towards his body and the way he seems to, well, market it.
There are many tidbits and little innuendos within the show that give us the doubt, wherever Dean did/didn’t sell his body (which I do not have on me right now. Be free to comment and add). Also, if you consider Word Of God as a source (and I actually, when it comes to Jensen, do) - this instance should be reminded (JA answers on the Q ~ where the boys ‘drum up their funds’, 2008):
It was “ruled out” as promotional “noise”, but I tend to give JA more credit than that. Just imho.
In any case, it’s out there, it was mentioned, no, you are not feverish for “seeing it”. So, did he? Didn’t he? I bet:
1. He did.
2. It began very early one, and I dare say very early (get your minds out of the gutter, not like that. I’ll get to it later).
3. Also, it was not what you would expect (that would be “take your mind out of the gutter #2″).
4. No, it wasn’t crucial to his physical survival or was his prime source of funding.
So, stating the above, I would reason that:
1. I think it would be too naive to think that as a child and a teen, he didn’t notice his surroundings, the people occupying the nearby no-tell-motel rooms, the weirdos in the gas stations, etc etc. As young as pre-puberty he would’ve already noticed the stares. He may have been a “goofy looking kid”, as Missouri described him, but I bet that was way early on, as a 6 y/o or so. I think he was very aware of the leering pretty early on. I dare say, as early as 10, he noticed that the right kind of smile, or posture, or sentence, would get you “stuff” from the cashier, the office clerk, the security guy, the nice lady in the booth, the motel cleaning lady and so on. This is actually the sad part, because it means he lost his “innocence”, the idea of smiling because he is happy or optimistic. That would have been erased early on, like I describe in my meta Dean Winchester Is The Immigrant Kid (in short: he was raised to show a very very tough front - he learned on his own skin that it is better this way. And it became as thick as it could get. I see dean as a very optimistic, loving, care-free, free-spirited child, that got hit on, hard, by life early on and repeatedly. He eventually had to put a sturdy facade of fake to survive).
And so, smiling became a way to get things instead of a feature of positive social interaction.
This is step number two, an ingrained physical trait, almost occurring by instinct.
And Dean? Is opportunistic. As much as human kind are opportunistic, he would make the most of it, as I see it. He “rides” beneficial situations: in research, intel/info gathering, scamming (he is, after all, a con man) etc.
2. So, it starts with a smile. As older he gets, and more observant, it spreads to other gestures, imho. Just look up for JA as Brady and turn on your imagination.
Later on, but not so late (again, lets stop being naive. I’m literally the only person out of my classmates that I know of that didn’t have sex before age 20. But oh well, it’s not a prime need of mine. But all my friends? Starting with the age of 12. STOP BEING NAIVE), as he began to “feel”, to grow, I think he connected the dots. He began seeing, not only pleasure, and maybe need, but also an opportunity. A way to a mean. And don’t forget that Dean’s social/sexual education came from the TV. THE TV! 80′-90′ TV! Poor child. He learned the hard way, of everything. From observation and from experience.
So I think that, very fast, he understood the stakes. The do’s and don’ts. How? Some sex-ed here, some eavesdropping there, some whatever else you might think of.
Dean is cautious enough, and was already training as a hunter. Which brings me to -
3. Dean Winchester is a killing machine. From a very young age, too. He will not be victimized by a human, he can strangle bigger opponents by the age of 16, and break some knee-caps as early as 9. It is comedic at best (me scusi) to say that he would earn by kneeling over. He wouldn’t, come on. Why would he? He can literally punch the sleaze out of conscious and just rob him. Like, who you gonna call…? The police…? “A male whore robbed me….?” No. (He may have used it, though.. Why not?).
That said, not all funds could be obtained by stealing and pool games. imho, sometimes, making money fast and hustle-free (pun intended) is the way to go. Which brings me to -
4. Why go further at all? Some of the most self-sufficient and financially independent people I know, are the way they are literally because they were young smokers: they had a need which they had to fund secretly, and fast. Addiction is expensive, and one’s body is a free resource, no extra “effort”. (I know, I’m simplifying. But drug addicts spiraling down to sell themselves for “just a little more” is not a movie trope. It’s very real).
No, as I imagine it, at some point, Dean took up smoking. Hell, everybody smoked back then, John probably smoked too, It would be a bit redundant to think otherwise, imho.
Booze, painkillers and sleeping pills, cigarettes - all of those would have been accessible to Dean. Hell, they all three Winchesters probably set down together and shared it at times!
But, as we all - fandom savvy ship-war veterans and meta-debate-old-silver-foxes - probably know, Dean needed more. Or at least, wanted more.
I figure, at times, when he had to make extra money for his own n(w)eed, and fast, he would definitely resort to prostitution. Too many opportunities and possible clientele were available.
I don’t think, up till very very much later on, he actually processed what he was doing, what he was a part of. (Remember - “No cash for ass” comment? In later seasons he refuses to pay for sex. It irks him on some level. I think that at some point he began facilitating a fine line between business and pleasure. It correlates with the steady rise of his self esteem).
Now, as to the mechanics.
Dean is straight. But, he “will trying anything once”. So he might be along the lines of the “experience curious”, and the “I don’t judge” mindset, which is perfectly aligns with anything he said or did Show-wise.
@teamfreewillbettertogether stated it perfectly:
There are men who sexually identify as bi and gay. There are men who have sex with men. The men who have sex with men often identify as bi or gay, but do not necessarily do… so Dean could’ve hooked with women or men. The men could’ve been straight, bi, or gay.
There are straight identified men who are not romantically or physically attracted to men who enjoy sucking cock.
Because of Dean’s upbringing and hang ups, I like to head canon him as straight, but possibly into dude sex [But with stronger emotional attachments to men] //Enter Benny…?
He seems to openly id as straight.
I definitely think Dean has issues, but I honestly see it as more Dean hiding domestic desires/wants… He has this idea that feminine = weakness… And in early seasons he equates homosexuality with feminine.
Also, apparently, as a straight male sex worker, there are plenty of ways to satisfy whoever you cater to, like I was made aware of recently [X]
So, combining all this information, the casual reader can assume what he would, or wouldn’t do for money. And I’ll leave that to you’ll to think of on your own.
My guess, also, that when a “client” is also “hot”, he would go for it as businessXpleasure combined. But other times, in more… dire situations? Well, we all know how well Dean can just shut himself off.
…Also, all of the above can actually explain Bad Boys: drugs is probably the only severe enough of a reason for John to do what he did, because any other explanation literally fails to do any justice with John Winchester and make this Swiss-cheese of an episode a proper canon.
As for John knowing or not knowing about Dean’s “extra income”, there are two ways to consider: he knew, and did nothing (no idea how to approach), or he had no idea. Either way, it wouldn’t have mattered. imho, he had his suspicions. And we saw Dean as bait under John’s leadership so it is very plausible they had some kind of muffled “talk” about it, or other circumstances, fitting for a different meta.
In any case, to assume John didn’t notice the extra attention his eldest receives wherever they go would be, again, naive.
Sam had to know, probably have guessed and pulled out the truth from Dean at some point. Probably also hated it, or was at least very uncomfortable about it.
So, that would be my very incomplete, brief and on-the-go half-assed meta on Dean and sex work. There is oodles of information, evidence and analysis that could be added here, and I will be glad to hear whatever whoever would like to comment and add.