Since we lose our virginity once, the only way I can approach the subject is with my personal experience.
Once I started thinking about sex, I heard all the horror stories. The main points being:
1. It's painful and unpleasant
2. You bleed
3. You just want to get it over with
With glowing reviews like that, who wouldn't want to jump in the sack? *insert sarcasm*
I had been masturbating on and off since I was about 13. Very light clitoral stimulation, never to completion. I would occasionally insert a finger or two but nothing especially mind blowing. Guys, skip this next tidbit and move onto the next part. Girls, I had tried using tampons but found them extremely painful. I was so scared this was a precursor to even more pain my first time. If you're able to use tampons, you're already ahead.
My opportunity for sex did not arise until I was 16. I started dating my family's friend's son. Sounds more complicated than it was. He was three years older. I guess that's where my affinity for older men began. We started dating in April and over the course of the next few months, rounded all the bases. It was new to both of us. You do not want to run to home plate if you haven't explored all other sexual avenues with each other beforehand. Know how your partner feels and tastes. The more comfortable you are with each other's anatomy, the more comfortable you'll be when it comes time to make the next step. Fingering is especially good warm up for the occasion. You'll slowly stretch the vagina and make tearing less of an issue.
Get your condom ready. Buy new. If you're afraid to be seen buying them, order online through various companies that ship discreetly. Seriously, your parents will not know just by looking at the box. My first toy purchase was so discreet, no one believed me when I told them what was inside. It is better to know and trust a new condom. You should not have the added concern of expiration and temperature control leading to breakage by getting one from a friend. While you're at it, purchase some lubricant. I will leave suggestions at the bottom of the blog.
Find a private place with no chance of disruption. You don't want your experience ruined by a pesky knock on the door etc. The position I used, and recommend, is having the girl on her back, legs slightly bent. My experience involved my boyfriend lubricating the condom and inserting himself using the missionary position. It sounds dull but for your first time, you want to be relaxed and have your body in a position that is comfortable.
I had zero pain and zero bleeding. He went slow but in all at once. I was completely at ease (and in love) and honestly couldn't believe that I wasn't experiencing what everyone warned me about. I can't promise that you will have the exact same experience as I had. Hymens and vaginas are not created equal. With masturbation, fingering and the missionary position, it will only better your chances at a less painful, if not painless penetration.
You'll have plenty of time in the future to experiment and get to the more exciting positions but for your first time, I recommend taking it slow and enjoying the moment while using a traditional position that is comfortable for both. This is just my experience and my suggestions based on how well it went for me.
For condoms, I recommend durex. I've never had an issue with them but I have with Trojans. I've used the regular lubricated, ribbed, warming, large and flavored. I'm a fan of the variety pack.
You can get them discreetly online from the website I use, edenfantasys.com or drugstore.com.
The drugstore box will say drugstore.com on the box. Drugstore.com Durex Link
Edenfantasys uses a fake name. Go through this link for a discount. You can use that link to search "Sliquid" for my favorite lube. I recommend "Sliquid H2O"
Relax. Get comfortable. Be SAFE!