I really enjoy foreplay. I especially enjoy doing whatever is needed to get a woman wet before sex. Recently I was eating someone out and she was really really wet. She did confess to me, she has not had sex in over a year so what happened next made sense. Right before I put the condom she tells me, you are probably not going to fit. I have heard this enough times before but never had any issues with penetration. To my surprise she was right. For the life of me, I could not put it in (granted I only tried doggy and missionary, in hindsight she should could have gotten on top). She proceeds to say, "I bet you feel good it is too big to fit" and I tell her "Why would I be happy at not having sex?". This was really frustrating. My night ended with the worst case of blue balls. On the following nights, we were able to finally have sex. So what has been your worst experience?