It depends upon the site; popularity does not guarantee that it is safe or secure. Various factors that can contribute to insecurity are (AND BE AWARE THAT THIS IS ONLY THE PARTIAL ANSWER):
Does it scrape or link to numerous other sites?
There are numerous free sites that collect links and display images to
porn on multiple other sites, but do not host any of it themselves.
One common theme about them is that they all redirect you to
advertisements, other porn collection sites, and continually hit you
with XXX dating site popups and video phone sex sites. In effect,
sending you down a rabbit hole looking for what you wanted, bypassing
browser protections, and offering multiple ways of collecting personal
information.
What resource types of porn does it host - GIFs, downloadable videos, pictures, flash videos?
Any type of content can have something malicious embedded into it. The
more it utilizes the system, the more potentially damaging it can be.
Who created the content, when was it created, and how many times has it been redistributed before it was uploaded to where it was found?
Many of the common porn sites still link to porn from decades ago,
hosted on sites that are not even remotely owned by the people who
originally created it. And it is sad to say, but a lot of porn is not
created or hosted by the nicest of people. There is also the fact that
there has always been a very strong connection between the sex trades
and criminal organizations. With cyber crime in the top 5 of
international crime, there is always a good chance that any site could
be a drive by computer compromise waiting to happen.
Is it an upload site where multiple people can upload whatever they want?
There are sites that allow any person to upload any type of graphic
material they want. Most of them that I have personally seen are
pretty archaic or amateurish in terms of their web technologies or
their execution. So it also implies that the back end protection might
also be old, outdated. or ineptly implemented.
Exceptions like the many Pinterest clones that allow you to upload a
link, and the site will scrape that content, probably have good
protection; but it probably also wouldn't provide protection from
unique malware with custom signatures that target zero day exploits.
There are constantly new forms of viruses, trojans, and worms being
produced that no anti-virus company is aware of. They only know when
someone who has detected a compromise submits a sample for analysis.
Who hosts it - tumblr, reddit, GoDaddy, Amazon EC2, private servers, etc?
Porn on the web can be hosted on any number of blog services, web
hosting companies, cloud platforms, or private servers. Which makes
for a huge number of variables between what is displayed, and the
protections in place to protect both the content and the people who
surf that site. A lot of porn sites are even hosted on compromised
home computers and university/business servers.
What OS, web server, and versions host the porn - Linux (Many), Windows Server (2000, 2003, 2008 R1 or R2, 2012), Apache, Nginx, IIS?
The older the operating system that hosts the web server, the more
outdated the technology and the more exploits and security flaws that
are known about it. The same applies to the various web servers. Every
hacker worth their salt knows how to fingerprint a server's OS to
determine version, scan its ports to find out which ones are open and
what services are listening, as well as make an initial determination
of what exploits and payloads are likely to allow them to compromise
it.
Where is the host located, is it cached in various geographic regions for faster distribution, and who caches it?
The general location of the physical host can give you a strong hint
about how compromising a porn site is likely to be. Servers located in
Russia, China, or Eastern Europe would be very suspicious. A smart way to get around
this is to have a proxy that redistributes the content from the
primary server. This both makes the distribution of the content faster
for various geographic locations since it is cached locally, but can also
obfuscate the actual origin of the content itself and inspire a false
sense of security.
What type and version of programming went into the website - Java, Ruby, Python, HTML, JavaScript, CSS, VisualBasic, etc?
The web pages themselves are composed of numerous possible elements,
all with various versions, possible compromises, sloppy programming,
links to databases, possible security keys, etc. Part of profiling a
web site for compromise is to take apart and analyze the application
itself. Just right clicking and hitting "View page source" will tell
you a lot. Defacing and compromising a website is one of the most
common ways for hackers to compromise identities for profit,
compromise computers to create drones for a botnet, encrypt a hard
drive for extortion, or just for the fun of crashing someone's
computer.