STDs - When you are deciding whether or not to hire a prostitute, STDs are probably the first thing that cross your mind, and for good reason. Any time you are sleeping with a woman who has been a lot of men, you're taking a risk that she has contracted an STD and will pass it on to you. Now, obviously you run this risk whether you are sleeping with a paid hooker, the town slut, your your innocent girl next door who's only had a handful of partners... but let's be real, the odds are probably a little higher with a hooker, right? Think about it, this woman is sleeping with anywhere from 3 to 15+ men per week. It's a pretty big risk, even with a condom. Neither option is risk free, but at least the women on hookup dating sites take the time to somewhat filter through who they choose to casually fuck and don't just have sex with any guy willing to pay.
Money - Prostitutes aren't cheap. If you want one that has all her teeth and isn't loaded on methamphetamines, you'll have to pay up. And assuming you want to fuck one regularly, that really starts to add up. It is much, much cheaper to join a sex hookup site, take a little time to make a profile, and start meeting people who actually want to fuck for free. Not only will you be saving money, but the caliber of woman you will be fucking for free can often be worth the price of a $1000 hooker. This one is a no brainer.
Quality of Connection - Answer this question for yourself: Does it turn me on knowing that the woman I'm sleeping with has been fucked so many times this week that she probably can't even feel my dick right now? Prostitutes see their Johns as dollar signs. You aren't a real person to her. Sex with you is not something arousing to her in the slightest. If you're lucky, she might be a very good actress and make you believe she is into it, but remember... you have to pay extra for that. Unless you're paying $500+ per hookup, most likely she'll be high and drugs or booze and barely present in the moment. On a dating site, you're going to meet women who are horny as hell. They want you, and they want to be fucked by you. That makes all the difference.
Safety - If you are picking up hookers off the street, or going to meet them in a hotel room, you are putting yourself at risk for getting mugged and/or stolen from. Are you prepared to face her pimp? If not, you better go to an upscale whore house, OR... just meet a woman on a dating site. Of course, you might have to deal with an angry husband or boyfriend from time to time, but he is less likely to be carrying a gun.
Legality - In most places, prostitution is illegal. Do you want to risk your reputation, your criminal record?
It's easy to fall into the fantasy of simply paying a reasonable amount of money to get a quick fuck. In a perfect world, something like that is completely possible. In some parts of Europe, that is completely possible. Unfortunately, that is not possible here. Prostitution is illegal and dangerous. If you spend a little time to find yourself a few fuck buddies, you can have sex on the regular, for free, with amazing and passionate women. To get some ideas of where to look for these women you can view our top reccommended hookup sites.