WebWorker Daily had an article about how to get the boss to allow you to tele-commute. I found it rather disturbing because of a base assumption that the boss is wrong. Pardon me if this gets rather lecture-y, but I think the people who most need to hear this are the people least likely to hear it.
The most important way to "convince" the boss of anything is to (duh) be a great worker. It is much easier to give telecommute privileges to someone who does their job well, with minimal supervision.
The reasons the article cites that a boss would not want a worker telecommuting mostly presume that the boss is an idiot. Employees who approach the issue with that kind of attitude are unlikely to get what you want. Try imagining that the boss has some good reasons. Remember, your boss has a boss, too, and if we’re smart, we will look for ways to all succeed together.
The article mentions the idea that perhaps the manager doesn’t trust you. That’s probably the most important point. While “you can’t make someone trust you,” you can earn trust.
There are certainly bozo bosses out there and maybe yours is one of them. But you also have to ask yourself if you’re part of the reason (especially is this is a repeating theme in your career). Even if it's not you, you'll benefit from making it work anyway. If you consider your boss’s success to be part of your mission, you’ll do better. Even if this job is a dead-end, you can practice better boss-relationship skills and they will serve you throughout your career.
OK, end of lecture. I'm working at home today and better get back to it. ;)