safe sext
June 1, 2011 3:55 PM   Subscribe

how can you safely send sexual content via email?

i use to be very careless and haven't done this in a while. how does one go about safely sending sexual content in emails these days. i don't want it attached to my real name. not that anyone would really care because i'm a nobody, but i don't look forward to this kind of thing slipping out and receiving any kind of unwanted attention.

at the risk of sounding naive i'm in the dark about this and hoping someone who knows better could give me direction.
posted by skwint to Computers & Internet (12 answers total) 7 users marked this as a favorite
I'd AES encrypt it and call it a day. You can do it pretty easily with something like AES Crypt.

As a bonus, you get to have sexy passwords!
posted by grammar corrections at 3:59 PM on June 1, 2011

are you sending sexual content to someone you know and trust? any photos you take can get out at any time for a host of reasons and if that's a life stopper for you, don't take the pictures. other than that - only send this to trustworthy people.

if you're trying to get your internet dating freak on - just set up a gmail account that doesn't use your real name, age, or zipcode and send every thing from there.
posted by nadawi at 4:01 PM on June 1, 2011 [1 favorite]

Create a Gmail account. Give the recipient the password. Instead of sending the content to an address, send the content to the Gmail account itself (i.e. email it to yourself).

Content can still be forwarded out of the account, of course -- it's only as secure as Gmail itself can get. But presuming the the recipient is trusted, you can essentially use Gmail as a dropbox instead of email, and you're limiting the total number of points of failure.
posted by Cool Papa Bell at 4:08 PM on June 1, 2011 [1 favorite]

How nerdy are you and the recipient?

The best-practice solution would probably be to use GPG. You generate a keypair, they generate a keypair, you send each other the public keys, and you can send stuff to each other without anyone being able to intercept it. Very elegant. However, it tends not to work with webmail very well -- if you want to be able to retrieve your pics (or whatever) from an internet cafe, it's probably going to be a no-go (since the internet cafe's computer won't have your key on it).

There are lots of GPG tutorials around, if you want to go this route. (Even video ones.)

However, if that's too complex ... you could just put the files in an encrypted RAR archive or Truecrypt volume, email it, and then communicate the password to the recipient via phone or some other method.
posted by Kadin2048 at 4:13 PM on June 1, 2011

you can essentially use Gmail as a dropbox instead of email

If you're willing to trust a 3rd party service with your content, rather than using Gmail as a dropbox, you could actually use Dropbox.
posted by Kadin2048 at 4:16 PM on June 1, 2011 [1 favorite]

It seems to me Cool Papa Bell's suggestion can be taken a step further: save the content as a draft without sending. That way nothing gets sent nowhere. The caveat that an unscrupulous reader could still make mischief still applies, of course.
posted by ricochet biscuit at 4:19 PM on June 1, 2011 [2 favorites]

There is unlikely to be much difference between sending between two gmail accounts, saving as a draft in one gmail account, uploading as a google doc, etc. In any of those scenarios you have to trust Google but only Google. (Or fill in alternate email/etc provider). It is different from sending between two email domains where the exposed surface is higher.
posted by wildcrdj at 4:25 PM on June 1, 2011 [1 favorite]

you could always buy a cheap usb drive and mail it. slap a password on there and email that to the intended recipient. No one seeing your email would have any idea and in the unlikely even anyone gets their hands on the usb they won't have the password.
posted by drethelin at 4:56 PM on June 1, 2011

I honestly wouldn't bother with all of this encryption; just get a gmail account with an alias and send it from there. The threat you're trying to protect your sexy self from is, your sexy messages associated with your sexy real name. All this crypto stuff is doing is preventing your sexy message from being intercepted either in transit or at the endpoints by some sexy third party.

In order for your sexy encrypted message to be of any sexy value to your sexy recipient, they'd need to unwind all that encryption anyway, at which point it's in the clear. Then your sexy recipient can do whatever they could have done with it if you hadn't done all that work, so why bother? Just set up your sexy email address to something you can plausibly deny belongs to sexy you, and then only use that sexy email address for the sexying.

Having said that, from this point forward I am going to start reading crypto papers, with their "Alice, Bob and Carol" example people in them, as "Sexy Alice, Sexy Bob and Sexy Carol". That should make the average crypto paper a lot more tolerably readable, now that I think about it.
posted by mhoye at 5:11 PM on June 1, 2011 [9 favorites]

Interesting thing about multiple gmail accounts for aliases - unless you use a variety of proxies, gmail, apparently can figure out when you have multiple gmail accounts and your main gmail account gets an option to access the "anonymous" accounts.



OP is a little ambiguous with the question. What parts of sending content do you want to keep "safe?"

1) that you sent stuff (possible)
2) that your sent stuff doesn't get disseminated (hahahahaha)
3) that *you* in particular sent something *particular* to *someone* in particular (easily done)


If all you care is "i don't want it attached to my real name"...

1) upload to random file/image depository site using a proxy/tor
2) anonymous posting to usenet using an anonymous OK provider.
posted by porpoise at 7:43 PM on June 1, 2011 [1 favorite]

Create a Gmail account. Give the recipient the password. Instead of sending the content to an address, send the content to the Gmail account itself (i.e. email it to yourself).
Actually, you could just use google docs for this. Or you and your friend could both get separate gmail accounts.
posted by delmoi at 1:53 AM on June 2, 2011

thank you for all your answers.
posted by skwint at 4:46 AM on April 10, 2012

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