I am in high school with my first serious girlfriend. Making out with her is just great but I wind up being pretty frustrated. She says she is not ready to go all the way. I think I am. How do you know when you are ready?
By "going all the way," I assume you mean having intercourse. A lot of people will tell you that if a penis hasn't been put inside a vagina, there hasn't been any sex, no matter how many orgasms took place. I have a different opinion, which is that there are a lot of different ways to please a partner. Intercourse is quite delightful, but it isn't necessarily superior to other forms of satisfaction.
You and your girlfriend have already started being sexual with one another. You're touching each other, kissing, and getting excited. Maybe there's been partial nudity. I'm not sure exactly where hands and tongues have gone, but you get the idea. As you point out, the problem is that making out feels wonderful, but it can be rather painful to get so excited without any release.
I wonder if your girlfriend would feel okay about giving each other orgasms without having intercourse. This takes a few of her potential anxieties off the table—like getting pregnant or saving her virginity for her wedding night with her husband.
Being touched is the way that most of us learn to come. Make sure your hands are clean before touching her vulva. You don't want to accidentally give her a vaginal infection. I hope you have enough space, time, privacy, and lighting to be able to look at her genitals and see her clitoris. It's that little bud at the top of her inner lips. Usually it has a little fold of skin or hood over it. The clitoris needs gentle stimulation, even during intercourse, for most women to have an orgasm. Sometimes it can be enough to just cup your hand over her pubic mound and apply some rhythmic pressure. If she will help you to put your fingers or hand in the right place, you could share a very intimate moment with her without asking her to "go all the way."
If your girlfriend likes or is ready for penetration, you can also try putting a finger or two inside of her. Be careful if she is worried about having her hymen broken. This membrane can be pretty fragile. Sometimes it's pretty tough, or even non-existent. Each woman's body is different. Her body is sensitive, and you are a lot stronger than she is, so be aware of that when you touch her. But if she urges you to go faster or apply more pressure, it's safe to do what she asks. The only rule here is to do what feels good for her.
Of course, your own body needs some attention too. Women love to stroke the back of a man's neck, squeeze and hold him, and touch his arms, chest, belly, back, legs, and feet. I haven't mentioned the one part of your body that probably needs the most attention. If the two of you feel ready, it would be great if she could use her hand to bring you some relief. You may have to show her how firmly to grip your shaft. Some women are afraid to squeeze hard enough. Show her how you masturbate, and let her experiment until she finds a pattern that excites and satisfies you. Some guys like to jerk off with lotion. If so, you might want to have some around for her to use on your cock. And it's always a good idea to have something handy, like a paper towel or tissue, to catch the come. Don't leave tell-tale stains on upholstery or clothing.
A key issue for young women is, does their boyfriend respect their privacy? Will he keep their activities private, or is he going to tell his friends what they are doing? This will inevitably make her the target of gossip at school. The things that people will have to say are not pretty. The two of you know that what you are doing isn't wrong. Men who know how to keep a secret are a lot more popular with the opposite sex. A gentleman doesn't kiss and tell—or get a handjob and tell.
Oral sex is an option or alternative to intercourse. Learning how to do this is easier if you are both clean. Take turns and keep a sense of humor. Don't choke her by cramming your cock down her throat—and don't expect a blowjob if you aren't willing to satisfy her as well. If you have trouble coming with oral sex, which is more common in the beginning for females than for males, be patient and fall back on your hands so nobody goes home frustrated.
There are some more factors to consider. One is the law. Is it legal for you and your girlfriend to have sex? Age of consent laws vary a great deal from one state to another in the U.S. If you are in Canada, there are still age of consent laws there. So make sure you know you are going to be okay. In general, it is not legal for someone over the age of 18 to have sex with someone under the age of 18. And it may not be legal for someone under 18 to have sex at all. If adults disapprove of your sexual activity and find out about it, they could make trouble, so be sure the two of you are all right. Your local Planned Parenthood chapter should be able to answer your questions about this without asking for your name or contact information.
The second big concern is birth control. Contrary to the popular myth, you can get pregnant the first time you have sex. She needs to be on the pill or receiving a hormone shot that makes it impossible for her to conceive, or you need to wear a condom. It is a good idea to back up that condom with some contraceptive foam or jelly. Practice jerkin g off with a condom for a few times before you try to wear one during sex. See how it feels to put one on (do this after you get erect), to receive stimulation while you've got it on, and keep it on while you ejaculate. Some guys complain that it's hard to feel everything while they are using a condom, but it is often necessary to use one anyway. The bonus is that it can make your erection last longer. After you come, hold the condom at the base of your penis while you withdraw. You don't want to lose it and risk spilling the contents.
Withdrawing before you come will reduce your chances of getting pregnant but not eliminate them. Precome can contain enough sperm to get your girlfriend pregnant, so be careful where you spill that juice. Even ejaculating on the outside of her vulva can result in conception. Those sperm are determined little devils.
If you have handled all of these concerns and she (or you) feel that it's wrong to have sex before marriage, don't do it. Respect your code of ethics, moral values, or religious beliefs. Violating these standards will cause regret at some point in the future. You want your first time to be and feel right. You might be able to pressure or manipulate her into having intercourse, but she isn't going to be a very enthusiastic partner, and that will make the whole experience feel pretty crappy for you.
Odds are that if this is your first serious relationship, it's not going to be your last. This is probably not the relationship that you will turn into marriage, a lifelong commitment, or a family. If she wants to be able to have her first intercourse with her husband on her wedding night, you could make that important experience impossible for her by being rash and hasty.
Don't be in a hurry to abandon making out for intercourse. Once you start having intercourse, making out is known as foreplay. It greatly increases the woman's pleasure by getting her ready for penetration. Making out teaches you about each other's bodies and builds your skill as lovers.
Having issued all of these cautions, I will conclude by saying that some high school sweethearts do stay together and eventually marry. And not everyone who has sex as a teenager regrets it. If you are mature enough to take the appropriate precautions and if you both have thought it over and come to the same conclusion and the same desire, it can be a tender and passionate experience that makes your relationship closer.
Maybe I shouldn't say that because the first time you try to have intercourse, the learning curve may be a little too sharp. The encounter may be rather awkward and brief. Some guys get so excited the first time they know they can have intercourse that they come very quickly. Just relax, make out with her some more, and wait until your body can produce another erection. Sex, like most skills, gets better with practice. Again, having a sense of humor and some flexibility are very important. If you have performance anxiety, talk it over with her. Both of you are virgins. She will, I hope, reassure you that she understands this is new territory. Be patient with each other, and things should eventually go more smoothly, last longer, and give you the emotional and physical experience you are seeking.