This is too complex a question for a simple answer. I recommend that you read each of the articles listed in the Index found at the top of the main screen.

The Index contains links to helpful informative insightful, as well as how-to articles that discuss the most common questions and concerns people ask about--like yours. Your question has been asked and answered. The reason I am asking you to read each of the articles in addition, is to become well informed. Often we do not know what we do not know, and in this case, knowledge is empowering.

I hope this is of help. Got questions?

There is not medical or physiological reason that you would experience pain. If you were having sex comfortably you will not have "revirginated" and need to repeat the early experiences. You may become tense because of anxiety or you may have need for additional lubrication if you are anticipating a sex marathon. Latex condoms are quite abrasive, so use poly condoms with plenty of lube. You may become sore but that would simply be from overdoing it.