Does this flirtation involve your having nude photos and videos of him too, or is just one way?

Oh wait, it doesn't matter. Revenge porn almost always hurts the woman. For her to be able to say "wait, I have nude photographs of you in compromising positions too" generally doesn't work.

Forget what you want from him. Forget what you're likely to get from him. Forget why he says he wants the videos.

Here's why he wants the videos: He can make money with them. He can make money selling them as porn. He can make money blackmailing you with them. It's not exactly money, but he can show the videos to his buds as a notch in his bedpost: Look what I got N-DWM to give me for free.

DTMFA and run!

@raindrop, to be fair to @Fuchu, that was my first thought too, and I'm not a particularly suspicious person.

L-dub, you aren't going to get what you want from this guy. Proceed accordingly.

Demiirelevant.. love it. Yes LW, cut this guy off whatever his story is.

It's possible that he is a voyeur and demisexual/demiromantic just BS

Why are you sending nude videos to a man you've never met and will never met? He can upload them in youporn or make money from them in patreon or onlyfans. Be prepared to have your ass all over the internet. You may have an online pimp and you're not even aware! he maybe even stringing more women for content too. Why do women fall for this demi crap?

Short but sweet. Great advice, Dan.

Who cares why? What matters is, are you satisfied? Are you happy? Does this interaction continue to be fulfilling for you? If not, move on.

Don't try to change him. I hope he finds the right non-touching-but-video-exchanging friend for him, and I hope you find and out of this world sex partner who makes you feel sexy, cherished, and desired!

Really? Are people stupid enough to do this?

Never mind. The Kardashians are multi-millionaires despite having no discernible talent.

Send those videos to everyone you’ve never met!

@7, Patriciav: yes, I notice the male arsenal for conning women has grown much more sophisticated since the blue balls days.

Why are you falling for this utter bullshit, LW? Come on, now. You are 39 years old, not 18! It’s way past time to wake up and smell the coffee.

And this woman is 39 yrs old, not an early twenties learning the ropes young woman.
LW, stop thinking men want you because they want nude photos/ videos of you. It’s tough not to easily trust half the world, but there you go.

@1 You're an idiot.

Here's the real explanation. He likes looking at you naked. And he likes the cheap thrill of telling you what to do. But he's not that into you. And it's not uncommon.

Here's the cheap breakdown:

60% of the world (here "world" means "the gender/s I'm attracted to) we want nothing to do with and have no real sexual interest in at all.
1% of the world, is a viable sexual/romantic partner. These are our "swipe rights."
The other 39% is you!

Amen Dan.

Did they ever meet in person? I couldn’t figure that out and it would be a major factor in my decision making process.
I started exchanging pictures, experiences, fantasies, c2c with others some 10 years ago and continue doing so on a smaller scale till this very day.
While it never occurred to me to publish any of the stuff I got over the years, regardless of how things ended, I wouldn’t write off Fichu @ 1 as unfortunately this stuff still happens. It was also confirmed by two qualified friends who said the w4w section on the late CL casual relationships section was full of straight men acting out a lesbian fantasy while phishing for pix in the process.

I’m no fan of LukeJoseph@13, yet would like to point out that common sense and mutual trust are paramount to this kind of arrangement, apparently like all others, and it is indeed possible to establish that. Like most others.
By common sense I mean taking the time to gauge what can be communicated or not, some safety measures like not revealing your true identity nor face, at least at the early stages.

The turns-ons may vary from watching and showing , ability to be intimate while maintaining anonymity, often discussing and acting upon stuff you may be reluctant to bring up with people you know. One can also negotiate a safe fantasy relationship of any kind. There's the thrill of telling others what to do, there's the thrill of following through.

She said they’ve been friends for several years. I re-read the letter, and saw nothing to indicate that this friendship was purely online. Not sure where people are getting this idea that they never met and never will.

Um, this guy is afraid of real intimacy. He's not Demisexual by accident. Probably a grown up damaged kid. Is this even complicated?

He's getting what he wants, you're not getting what you want. Proceed accordingly.

Not that complicated sporty @ 17. All of us are “grown up damaged kid(s)” to some degree or another. No doubt I’m qualified. As such I'm honored to rely on my experience and cherish the opportunity to speculate on others.

Good point KillerSmile @16, and this guy is thirteen years younger, which makes him twenty six.
Concur with Sportlandia @17, this kid is damaged or while pictures and videos of an older women are hot, actually dealing with her in the flesh is way different. What would mother say?
My advice stays the same...cut him loose.
Nobody is clued in LW, why this man is behaving this way. That you know him maybe lessens the fear your pictures might do the rounds.
Whatever label this man has stuck on himself, doesn’t matter. He wants content for his spank bank, so please stop obliging him.

He's just not that into you. Move on.

Killer @16, only one person seems to have got that idea. I see nothing to indicate it's the case either.

I'm not sure I follow the lw's reference to what she only does in 'live shows'--is she a cammer or some other kind of sex worker? This was my interpretation; but there isn't much (anything) about sex work in the comments backing it up. So maybe 'live shows' is just a metaphor? Could it be that the lw's ordinary way of starting a relationship is to offer something like a striptease only to guys she has started to meet in person, to have 'sleepovers' with--as a prelude to (more) sex? Well... if this is so, I'd suppose she has to offer a sleepover, offer sex, and get a clear 'yes' or 'no'. Whatever the reason for a 'no', stop obsessing and move on.

M? Harriet@23, I took the fact that “live shows” was in quotes to mean things that she only does when she is actually with someone in person. I will confess that it gave me pause, and my first thought was camming, but that didn't really fit in with the context of the letter or my own experience (yes, projecting, but it reminded me of a friend I sexted with who wanted graphic pics of things that I am comfortable with an actual sexual partner seeing but not someone I have never had sex with. It felt awkward without all the stuff that makes irl sex not so embarrassing.)

He wants to wank off to you without any emotional support, connection, or any of the messy and tedious parts of an actual relationship or physical contact. It's not that complicated. Unless you get off on this as well, move on. He's a user.

Meh. As an older woman that has enjoyed younger men, I would comment that they certainly can be fun and hot, but are often of a me me me type persuasion, and cannot be relied upon for anything substantial or to know really what they want.

This usually becomes tiresome after a brief (yet often delightful) period of time.

Tachy @24, I had the same interpretation of "'live' shows" as you: She will do this thing in person, but not record herself doing it and send it to someone. (No projection, if that bolsters your interpretation.)

Sandwiches @26-@27: I agree; the only thing that makes putting up with them worthwhile is the sex, which she's not getting. If she wants a fling with a young man, there are plenty of sexual ones out there. Tinder it up and start swiping, NDWM.

"...something I only offer in "live" shows..."

Indeed interesting phrasing by the LW that she 'offers shows'.

I think by "live shows" LW meant "in person." I see no indication she is doing commercial camming. If she would there would be no issue sending a custom video. For a fee.

Am I the only one who just learned the term Demisexual? And where do those semi non-sexuals have to do to get in the alphabet?

When done in good faith online erotic exchange can be a lot of fun. It works for whatever reasons and doesn’t need to be put down in case participant/s never meet face to face.
I found CBU @ 29 to be somewhat condescending with “A landmark birthday, thoughts of aging, starting to feel invisible and maybe a little desperate, sudden attention from a younger man...”

I also found out few minutes too late that tachy @ 24 and BDF @ 28 have already stated what I attempted to convey in my previous post.
For the record, I am projecting.

Hmmm.... She says the "flirtation has escalated to include nude photos and videos," but the specific instances she alludes to involve her sending videos and photos that he requests.

Here's an explanation that jumped out at me: he is attracted to her but has a sexual hang-up (micro-penis -- or if she has seen nude pictures of him, severe premature ejaculation, or something like that) and is absolutely terrified of having to open himself up in the context of an IRL sexual relationship. So now he's basically laundering his crushing sexual anxieties through the guise of an identity.

Which doesn't mean she should stick around. She needs to find someone who meets her sexual and emotional needs. But it wouldn't surprise me if there were some straightforward body image issue or sexual dysfunction lurking behind his behavior.

Cocky @29, this isn't a sudden midlife crisis move for her: "For several years I’ve had a increasingly flirtatious friendship with a man thirteen years my junior." Which means that he was only in his early 20s when this flirtation began. Many have been there indeed, but this doesn't necessarily mean this woman is one of them. Believe it or not, there are 39-year-old women out there with self-esteem! :)

CMD @33: Somewhat? ;) Thanks for sticking up for us invisible old ladies, haha.

Pythag @34: I think he's just giving her the old-fashioned runaround, but if she wants to tell herself he has ED or a tiny penis to help get over this mad crush, that may indeed be a good strategy.

BDF- I attempted to be polite to cbu. My heart, as well as my exposed bum once on my knees cleaning the kitchen floor wearing my short sexy maid outfit, are 100% with visible and invisible old ladies.

In related news: I’m getting tired of people suggesting here that there must be something fundamentally wrong with people who are up to online exchanges. They’re fucked up, they’re too old, they must be hiding something.

Some of us are simply happy to indulge, mostly as a sexy add on to our lives. Take it as a preference, just like anal sex or domming your spouse which were discussed recently.

@36 CMDwannabe We are all involved in an online exchange of sorts here, though not an intimate one. Do any of us know each other in real life? I doubt it.

BiForDan @35 -

Your comment seems kind of dismissive to me.

Her description of their relationship does not fit any version of "the old-fashioned runaround" that I'm familiar with. If he were not attracted to her, or he were worried about the impact of a sexual dimension on their friendship, he would not be actively requesting sexually explicit videos from her. If he were simply callous and toying with her emotions, then why is he doing so in a way that doesn't him get laid? That makes no sense. Men act out of motives, too.

There is an unwillingness to acknowledge male body issues or the impact they have on people. I offered a simple explanation that fits all of the known facts, one that I think is at least as plausible as the explanation popular on this forum, which essentially boils down to, "even though she has found years of friendship with him to be worthwhile, he's probably doing this because he is a fundamentally bad person."

@24 tachycardia, @26 Bi & 30 curious. OK, she isn't camming. It's just a slightly awkward phrase. It's being 'live' shows, not 'live shows' makes it a bit clearer to me she's making a joke. Though maybe it's not inconceivable that cammers get crushes on their johns.

Ms. Mooz @ 37
I think that over the years some of us have already established at least an online connection with others. I can recall one who offered their D/s expertise, another who referred us to their poetry website, and at least one clean kitchen.

cbu @ 38
Rest assured, we’re all projecting, we all have our shticks. Adding a personal connection to an assertion of some sort is likely to make it more meaningful, probably less likely to make it come across as an offensive generalization to others.
It may still happen on occasion, life goes on.

@25 Oh, I would put a million dollars on the thing he wants most being emotional support.

Lava @10, I used to believe that blue balls were an entirely fictional thing men used to convince women to have sex with them out of pity. Then one night I had sex for a long time when I was far too drunk to come. The next day, They Hurt. So. Much! After that, for quite some time I could get blue balls from pretty minor sexual arousal without release. Now things are good again, but blue balls are not always a lie.

Oh no dcp123, I never thought them a lie, just used as a well worn excuse to pressure girls to have sex.

He uses term demisexual, but it seems he is afraid of real emotional connection. You wanted to get closer to him emotionally; you have real feelings for him. You wanted to go beyond videos and flirtation. He got scared and could not let you get that close, though he may really want to.

Like a lot of people, he may get scared by closeness. He probably has good reason to be. He has been hurt and the damage is still there. Show him compassion. And try to remember: It's not about you.

Probably best not to expect him to change this deep pattern or be able to reciprocate in the way you want. Look at it this way: He has a broken arm; he can see about it and you hope he will. Until he does, though, he won't be playing sports and he would not be a great teammate for you.

Cocky @38, apology accepted! I sympathise -- internalised ageism is a bitch, I struggle with it sometimes myself.

Pythag @39, perhaps my comment reads as "dismissive" because I believe it's in her best interest, indeed, to dismiss him. Perhaps he is dismissing her because he is ashamed of some sexual dysfunction. What difference does that make to the situation? She wants to take their flirtation to a more physical level, he does not. Are you suggesting that she try to override his "no" with requests that he see a doctor? Sure, men have motives; aside from his stated explanation that he is demisexual/demiromantic and prefers masturbating to partnered sex, he may not want to get involved with someone her age; he may have another partner, and this isn't "cheating" to his mind but physical contact is; he simply doesn't want the drama of dating; he has an STI he may not want to disclose; he thinks she would get too attached. Many reasons he might be giving her the newfangled runaround, and it just struck me as classic toxic masculinity to suggest that if he doesn't want to fuck her that there must be something wrong with him. In the end, from her perspective the reason doesn't matter. He doesn't want her. Console herself however she needs to, and move on.

Dan was right that this is a situation in which deep analysis is pointless. All you need to know is you aren’t satisfied, you probably won’t be satisfied. So for your own sanity just go back to being solely platonic with this dude.

In Isaac Asimov's books, there's a planet called Solaria whose inhabitants are terrified of direct human contact, and prefer to interact exclusively via holographic screens. This turns out to be quite a prescient bit of writing on Asimov's part.

There's are a LOT of young people out there who feel really uncomfortable interacting with others in person, prefer to live and socialize through their phones and computers exclusively -- and, frankly, many of them would rather masturbate to the IDEA of someone than actually have sex with them, even if that person is willing and available.

Obviously there have always been people like this -- folks on the spectrum have a tendency to end up in this kind of situation, both because of their social difficulties and because they struggle with the sensory overload and uncontrolled chaos of normal human interaction. (I knew someone who dated a guy who preferred to text rather than converse, even when they were in the same house.) And then there are other, culturally-specific phenomena like Japan's hikikomori.

But we're going to see more and more of this over the coming years, and I think LW's guy is but one example. It's partly an anxiety thing, but also has to do with control and objectification -- not wanting to have to interact with all aspects of a person, but instead confining things to only that narrow slice of their personhood that suits their needs at that time.

(Is she hot in that one Instagram shot? Then why not rub one out to the picture, instead of having to see all the angles where she looks far more ordinary? And then you've got your release for the day, and can go back to playing Fortnite or whatever distraction you've got going.)

I think we've unwittingly taught kids the dangerous lesson that they have the right to complete control of their interactions -- that other people are an à la carte menu, from which you take what you want and aren't obligated to be responsible toward the things you don't like -- before they go on to live a world that inevitably teaches EVERYONE that control is the one thing they don't have and will ultimately be taken away from them, no exceptions.

Though I'm very hesitant to dismiss the given explanation of demisexuality, as someone with sometimes crippling anxiety, I can totally see this behavior coming from an anxiety disorder. (Projection alert!) The categorical refusal to make things more personal is what sticks out to me, especially rejecting a sleepover where there is no suggestion that sex could even take place.

Social anxiety can make the very idea of being near a person overwhelming, and if it's coupled with depression, even thinking about interacting can feel exhausting. At least for me. This can lead to avoiding broad categories of situations that are even peripherally related to what the anxiety is about. Avoidance is a key behavior to target in treatment where anxiety is concerned.

Not that the LW should tell the non-boyfriend this theory; it would be condescending at best, even if this was the reason for his behavior, and dismissive of his stated identity at worst.

I agree that the explanation has no bearing on what the LW should do. The relationship (or non-relationship, whatever it is) is not only not working for her, it's taking an emotional toll. She needs to end it one way or another.

Ytterby @48, gold star. This GenX woman can't understand how her millennial crush interacts with the world, including her. I think you have nailed it.
Calliope @49, social anxiety is a good possibility too. And you're right that she shouldn't challenge the guy's demisexual identity and offer her own theories as to why he isn't interested. He isn't interested. That's all she needs to accept.

I wish I could remember what it's called, but I know I've heard of a weird spot on the asexuality spectrum where someone is intellectually interested in sex, and interested in facilitating/watching it, but not interested in actually participating. Maybe this is a case of that?

Ytterby @ 48 - If you're interested (and haven't read it already), "City" by Clifford D. Simak had a similar concept. Most of humanity has left Earth, and the few who remain become terrified of meeting face-to-face.

@52 - You might be thinking of autochrissexuality? I've seen it refer to 'people who fantasise in third-person without incorporating themselves in the fantasies'. When I'm having a bit of solo fun, it's like I'm directing a porno in my head - but I don't make an appearance at all.