I am a undergraduate college student. I have had 4 relationships. I am now in a relationship with a girl that I really like and I would really like to make come. There are a couple problems. She takes the pill all the time because of blood/period problems. So there is no worry of getting pregnant. Especially since she has never let any guy come inside her, because she is cautious and make me and had made her past boyfriend wear a condom. Now, when I wear a condom, I can go for a good while, and I have gone for a long while in the past. However, with this girl, I can never go long enough for her to come. I know she has come before, just not with me. I like her a lot, but I can't help feeling less like a man when I can't satisfy her. I have also gotten better at cunnilingus, but i don't think she's fully come from that, close though. Now, this is where it gets more complicated. Yesterday, we started to have sex after a short boat cruise, and we were so aroused I didn't even put on a condom. She was not only fine with it, she didn't want me to. Once we started, she also made it clear that she wanted me to come in her. Considering that no one had ever done that, it seemed pretty important to make her come, and make it more special. What actually happened was me not going nearly as long as I do with a condom, and her getting frustrated. Needless to say, I decided not to come in her because I felt embarrassed and unmanly. I need to figure out how to make her come, and just as importantly, last long enough to do it, hopefully more than once. Please, if you feel you have any useful advice, anything would help. Thank you.