Her First Time
Most women are naturally a bit afraid of their first time making love. There's a lot on the line, her virginity, which most likely she only wants to give to someone with whom she is deeply in love with. Will she do well? Will she satisfy her man? Will it hurt? These are all questions that go through the minds of virgin females. Of course, if you're here, and you are a virgin female that may be making love sometime soon, you're probably wondering, "What should I do to make my first vaginal sex experience easiest?" And if you're an experienced male who will be making love with a virgin female, you also could benefit from this guide by knowing how best to help her through this important and special time in her life. The best possible solution I can think of is the following list of guidelines:

  1. Do it in a place where she feels safe, ideally in her own bedroom.
    2. Do it in a place where she feels safe, ideally in her own bedroom.
  2. Do it at a secure time, when roommates/parents/friends/pets won't come barging in, a fire drill is unlikely, etc
  3. Simulate it in advance: - Go almost all the way. - Practice the thrusting motions of sex while fully clothed. - Have her give you a hand job or blowjob so that she will know what your body does when you have an orgasm. - Have a bright lights "show and tell" session, to allow you to feel secure around each other's naked bodies.
  4. Plan it, but don't talk about it being planned, on the actual day that you do it.
  5. Stretch the vagina out a lot with the fingers in advance. If she feels comfortable with the idea, she can even do this herself when you're not around.
  6. Remember that this is her day: everything within reason should be done how she wants.
  7. Spend the day with her beforehand; do something fun but generic. If you do something complicated, it will become "your" thing to do together forever, due to the association, so make sure it's something you can stand doing again on any potential anniversaries.
  8. Have a special dinner before you "start." - Nothing that can possibly upset the stomach. - A moderate amount, even if you're nervous. You should both stay a little hungry and not feel bloated.
  9. Use plenty of lubricant. I recommend K-Y jelly for the first few times. After that you may want to consider a slightly less slippery but spermicidal lubricant, several brands are available commercially.
  10. Entry should be "missionary" style; this leaves the vagina as wide open as possible. Some women find that placing a pillow under their butts enhances this effect; others have said it doesn't matter.
  11. If she can do it, she may be best off to do the actual entry herself, but many women would rather not. Just make sure this act is accomplished in a way that makes you both happy.
  12. Take everything during the actual intercourse session as slowly as possible because you're trying to make this as easy as you can for her. Thrusting a big hard penis into her before she's ready or at too rapid a pace can really hurt her physically and emotionally. Try inserting it extremely slowly, go in as far as possible, and be sure to communicate with her during this whole process on at least some level. If it hurts, back off, and try again later. If insertion goes well begin lightly and slowly thrusting in and out, then decide what, if any, variety to add.
  13. There's no point in getting it over with right away, since it will only hurt the next time, but there is also no need to draw it out. An appropriate time frame depends on your previous sexual activity with this person (oral/anal sex) and how well you already know each other and your bodies.
  14. Take as much time as you need before putting it in. Only when the woman is really ready should this be done. I'd recommend asking verbally, and then interpreting that to see if she really means it's time.
  15. Stay with her afterwards. Spend the night, at least. If possible, take her to do something spontaneous the next day. Discuss what happened if she wants to, many women won't want to until some later time.
  16. Encourage her to talk to other women ahead of time to give her some idea of what to expect. The unknown means fear, fear leads to tension, tension leads to difficulty relaxing, and difficulty relaxing leads to pain.
  17. A useful technique, for guys who can do this, is to keep the erection soft, at a sort of middling state, and then push the penis in with a finger. Then slowly let it harden. This will produce a stretching rather than a sudden opening of the vagina. If you can't do this, then at least go in slowly and gently, "getting it over with fast" is not likely to be better.
  18. Be more or less "in love." This is something you can't just decide to do, but it can help to wait until you love each other. And from my point of view, making love is the only option; there isn't just "sex." Make sure you're sharing something, not just getting something for yourself.
    Remember, this experience should be an extremely special and intimate time for both partners. This list does little to accurately describe how any one experience will or should go, but rather you should use it to come up with ideas of your own or use it as a vague set of guidelines when considering what to do and how to make it go the best. Good luck, and remember, the best companion to great lovemaking is love and the best vessel for love is communication.