Whenever i finger or perform oral on my girlfriend she shows all the signs of loving it, including moaning, clenching the sheets, quickening or erratic breath, and other signs but as soon as i think she's going to reach orgasm she tells me to stop because its too much for her to handle or sometimes even hurts. She wants to get there but we dont know how to overcome this obstacle. Any help or advice is appreciated!
Have her let you know when it just begins to get sore. Then move back about 3 inches and stimulate her only with your breath. (Remember to make a joke about giving her a "blow job" afterwards.)
In my experience, it is quite common for guys to be somewhere between aweful and barely tolerable when it comes to giving oral stimulation to me. But even worse is 'fingering.' Guys generally just don't have a clue how to pleasure me with their hands and it can be unpleasant or even mildly painful. Of course that's just been my experience. There's no need for any guys to defend their fingering or cunnilingus skills. My advice: Avoid the fingering, just rub gently over the panties a bit (this helps distribute the pressure and avoid the unpleasant friction of coarse fingertips against the clit). And once the panties are off, hands off. Have her sit on your face so she can grind a little and have some control. Or better yet, stimulate her clit with your dick. IMO, that works a thousand times better.