How To Use a Condom?

I had to boil this down to the core, so the brackets and ellipses ( [...] ) represent things I've cut out and answered in my email response.

"[...] I have been brought up in a very strict and conservative household with only a mother. I am getting married next week and scared out of my wits. [...] Neither of us have had any sexual experiences. The wedding night has me so nervous that I haven't even been able to masturbate because I can't get an erection. [...] Here in our town sex is not discussed. Church tells us only that we are supposed to get married and have families. We agree we are too young to have children. I had to travel to a fairly large city to even find condoms which I have hidden in my suitcase. I opened the box and there are instructions on how to put them on and take them off. But when do I put it on?"

Young and inexperienced coupled with minimal information can lead to disaster. Untold problems can result in such a lack of education. Families and communities think they are doing their young people a favor by shielding them. Knowledge is key to success. I was happy to read you've done some internet surfing to fill in some gaps. That you're nervous is understandable. And nerves will absolutely cause your difficulty in getting hard. You need to relax - try to do some meditation.

When to put on a condom? Ordinarily, I would tell you to wait until just before you are going to enter her. But, pre-ejaculate - or, pre-cum - can contain sperm. You don't want either your (or her) hands to carry this to her vagina. 

So, I'm going to suggest that until you are both more experienced in foreplay to put the condom in place as soon as your cock is hard, and make sure it is firmly in place.

I don't think you will have trouble getting hard once you are safely in the hotel. You might actually work this into the foreplay. Have her help you put it on. And, remember to communicate during sex. Sex should not only be pleasurable for both of you, it should be fun.

If it seems too awkward to ask pointed questions (Is this good? Do you like this?) you can actually lead by example by telling her when something feels good to you. Moans, sighs work too, in addition to actual words. You can guide her to do what feels good for you. You can place her hands on top of yours and say, "Show me."

You should also know when to remove the condom. (Do not cum twice using the same one.) You can remove it whether your cock has softened or not. But use either TP or facial tissue to wrap the used one(s) and place in a waste can (do not flush them!).

Always have a hand towel to wipe your cock, balls, and hands completely dry and free of cum.

While I encourage you to watch some porn (I suspect you already have), consider watching together. There is a lot of porn that is recommended for women and couples. It will give you both a means of expressing what you might be interested in trying. But, by no means should you rip the condom off to cum (like you'll see in many porn videos).

 Semen has a sneaky way of getting where you may not want it to go.