Speech Gltich

A funny glitch you may want to use in Skyrim to get your Speech level to 100:

1. Take off for Riften. A guard will be waiting outside the door.
2. Bribe, persuade, or intimidate the guard to let you inside. When you’re in the town, enter the Black Briar Meadrey. Save your game before continuing.
3. You’re looking for Ungrien in the tavern. Just wait if he isn’t around, he’ll eventually show up at the bar.
4. Talk to Ungrien, and choose the “Tell Me About…” speech option. Then choose to Bribe him.
5. After bribing him, choose the “Tell me About…” speech option again. Now, instead of trying to Bribe him, try to Persuade him.
6. Choose the Bribe speech option again, whether you succeed or fail trying to Persuade Ungrien doesn’t matter.
7. Choose the “Tell me About…” option a third time. Then choose the Persuade option for a second time.
8. Now, just keep choosing the Persuade option. You’ll continue to gain Speech skill points. It’s just that easy.

Source: http://www.gamefront.com/skyrim-easy-100-speech-skill-glitch/

If you are a PC game, you might also want to macro your gaming keyboard to repeatedly press enter so that your hands don't get too tired.