How does one keep a conversation going?

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This is very likely my biggest problem socially, and may very well be my only problem.
Sure it's no magical fix to know how to keep a conversation going but damn, it's pretty close.

Right now I usually just insult people just to keep the conversation going.
I've been getting mixed reviews on the internet, but in meatspace, most people seem to like me.
Asking questions seems to be a viable option, and so it telling stories.

But most of my stories end up being narcissistic ego-fests of my own imagination.

I usually start blurting. (not recommended)

Insulting people more often than not creates an uncomfortable atmosphere which is not good for maintaining a conversation.

It's always quite difficult to make friends, it doesn't always work out even for those of us without social issues. But if you're talking about maintaining conversations with friends you already have:

1. Have in mind what topics of conversation you believe they may be interested in.
2. Open by asking them a general question about how things are going and see if the other person zones in on a particular topic. For example, "How are things?", "I had a bad exam today", then the conversation turns into something to do with that exam. If they just say "fine" and give you poor signals with their voice/body language, maybe they're in a bad mood. If they say "fine" and give no such signals, ask them a general question about something you feel they are interested in.
3. In the middle of conversation, listen to what the other person says and either give advice, talk about how you can relate to them or how you're different (preferably the former; doing the latter too much will alienate people), say make an encouraging remark on the topic, or ask a question about what they just said.
4. If they don't appear to know what to say in response, quickly revert back to asking a question about something they said.
5. Make an excuse to leave when the time is right. If you're walking with them, of course the point where your paths diverge is the ideal place to leave - just say "oh, I'm going this way - I'll see you tomorrow". If you're just standing with them, think of something you might have to be doing. Respect the possibility that they might have to do something as well.

It helps to be relaxed for two reasons. The first is that you may remember details from the conversation well enough to keep it going. The second is that you'll probably appear relaxed as well, which is a great asset in keeping a conversation going.

If eye contact is an issue for you, you might have to work on that.

Stories are good, but you should only tell them if the other person enthusiastically invites you to.

I ask the other person questions about their own interests, and listen to them bask in their glory.

Conversations are like train tracks. You either have to expand your current track, or divert into a new direction and repeat. If you try to force the train to jump, you'll probably end up with a great bloody mess.

You could always just inquire further about something the said or mentioned during your previous lines of questioning, but you should be willing to let a dead conversation die.

Also hobbies are a low risk topic that might at least get you to a second date.

I don't actually do things in rigidly defined things such as dates.
I just go places and see what happens.
I usually talk about music, which interests most people.
But I'd have to let you know this is just about online talks.
Offline talks are so much easier.

Social interaction is complex, but with enough practice, one begins to recognize patterns of causality between what you say and what reaction it invokes. For me, that development involved lots of weird conversational mistakes, but I think I've gotten it down pretty well.
You do have to be comfortable though, I think. That takes practice.