Don't!

But seriously, folks: The most important things are:

  • Focusing on the virgin, not yourself (this also applies, if you're both virgins).
  • Don't expect yourself to get anything out of it.
  • Don't rush it.
  • Don't push him/her into doing it if he/she regrets halfway through.

And now, assuming that the virgin is female:

Probably the best thing is to make sure that she has an orgasm even before your start sticking your Big Willie into her. There are multiple ways of achieving this - think of one yourself. Furthermore, as always, when you fuck, give her the control: Lead her hands down to be able to make space for the thang. And let her come on top of you.

But in general, the top advice should do: Keep calm - and don't forget to end it all with a nice "oh my god i'm coming" face!

Some further notes:
  • Eat light food - if you eat heavy food, you get sleepy and your body becomes less sensitive. Do not drop eating, though - being hungry will distract you from the experience, and thus also decrease sensitivity.

  • Choose a time when you are both rested.

  • If both are virgins: Remember that 'wet' means 'wet', not 'damp'. Foreplay to achieve this takes time; try to spend hours, not minutes (unless both of you suddenly feel that you need it to happen now, in which case you are probably ready :)

    Apart from that, I still like the writeup overall, and definitely agree with the part at the end - it is not very likely to be a wonderous experience, but it will be an experience you remember, will look back at, and will have emotions around.

  • Males will (usually) ejaculate quickly the first time. However, coming does not mean you have to stop! In most cases, you can get an erection again inside a reasonably short period of time (minutes to an hour.) Spend the time between just cuddling, enjoying the new closeness you've found, and talking about how it feels.

  • People usually bond to the person that takes their virginity. Make sure this will not create problems in the life of either of you. I do not believe it is extremely important to love the first person you make love to (though it probably heighten the experience), but you should be very comfortable with him or her - it should be someone that is a friend, no matter what.

  • There are a lot of ways to be sexually intimate without having intercourse. Spend the time to get to know each other's bodies before going for The Big One. I think progressing from simple caressing through kisses to petting, petting to orgasm, and oral sex, and ending it all with intercourse will give you the most enjoyment out of the latter - and spending the time to build up to it should make the final act much more exciting.

  • Make sure you have time for each other afterwards; at least a few hours, preferably days.

  • Talk to each other about it. If you are the virigin party: Tell your partner that it is the first time, talk about how it feels, what is good, what is not so good, things you want to try, etc.

  • Make sound - sound is exciting. If you are used to being quiet when masturbating - try to suppress the habit when you're with a partner. Few things are more exciting than hearing that what you are doing with somebody works for them.

  • Do not hunt for orgasms, particularly not as a part of the actual intercourse. What is important is the closeness, the round, enveloping feeling of having somebody be as close to you as is physically possible. Orgasms will come in time, and your technique and adaption to each other will mature - do not stress about it.

... and the most important point: Try to relax, be comfortable and enjoy it!


daz eddy: I do not agree with the advice (for males) of wearing a condom unless this is required for "the usual reasons." In my opinion, time to ejaculation is not important, and especially not something that you should see as important for the first time you have sex. Closeness and comfort is important, and most males feel sex with a condom as much more distant. If you feel you come too fast when you have the background to evaluate, there are a lot of techniques for extending the time to ejaculation (or dropping ejaculation alltogether); I personally have gotten a lot of pleasures from the sexual Tantra techniques. However, a small warning: I'd not recommend the Kama Sutra for actual technique - get other references. The Kama Sutra is an interesting work, but it is sort of like the bible - written by a lot of different authors, not easily comprehensible, and with things that are more or less repeated (for instance, the variation between two of the different positions are at which angle the female holds her hand.)

As for females: I'd recommend using a lubricant rather than or in addition to condoms. As far as I know, the feeling of increased distance when using condoms is weaker in females than in males, and often absent alltogether - so the advice for males above doesn't apply that much. Feeling comfortable is what is most important - if you feel more comfortable with a condom than without, by all means use one.

Apart from that, I agree with eddy's advice.

A couple of small additions/ammendments to the above:

Virgin guy:
Before the action he will be thinking 'wahay!!' mixed in with worries of stories he's heard about premature ejaculation.

  • Wear a condom. - it makes the guy less sensitive so he might last a bit longer.
Virgin girl:
Probably (after all, us guys have no idea what's going on in the female mind) worrying about whether she should be doing this and whether something is going to go wrong and she'll end up pregnant. She'll be curious as to how it will feel and she will find out that it will feel something like somebody trying to push an elephant through an extremely tender eye of a needle.
  • Wear a condom. - it helps to lubricate the whole process, therefore reduces the pain. Also will help to calm her fears about pregnancy, even though it is not as reliable as the pill it is a protection that she can see and feel doing its job and you instantly know if it hasnt.
  • I agree with Cyt that there's a chance that she'll have a change of heart - go with it, the more space and time you give her the sooner she will be prepared to have another go.
  • Chances are on the first attempt you won't even get half way in before she starts whincing in pain. You've heard the stories of various countries where men proudly showed off the blood stained bedsheets that were used by him and his bride the night before, well imagine your meat and two vegetables being stretched to the point of ripping and bleeding everywhere - sounds painful, doesn't it? think you're going to enjoy an orgasm in the middle of that? not likely.
  • But guys, the main point here (and I can't stress it enough) is that you really have to take it slowly in fact, imagine slow, divide it by the largest number you can think of and you still 'aint slow enough - and that's just for an experienced girl who doesn't have the added excruciating pain, for a virgin you have to move so slowly that you're practically moving backwards.
And now for the obligatory ending note:
Don't worry about the first time, it is heralded as the most wonderful event in your life but more often than not it is embarrasing for guys and painful for girls. Stick with it - It does get better!!!!

EE - Time to ejaculation may not be important for everyone but I know that an extremely large number of guys see things otherwise. That's why I included the bit about the condom .... as an example, I do everything possible to make sure I come last (This is the only sport where I do that ;) ) - it sort of seems polite that way.

I'm addressing a man about to share sex with a woman. It is her first time. It may or may not be his. He loves her, or at least cares about her and is able to act lovingly. I cannot give advice about sex-without-love as it is something I think is a Bad Thing. YMMV.

Make sure you have a whole heap of time together and in privacy before you begin. That's hours and, if at all possible, days I'm talking about. No one should be worrying about their dad coming home and getting mad, or their parents getting a phone call to find out why they aren't in school
No one's virginity should be given in rushed or fearfilled circumstances
Don't rush either her or yourself

Hurried sex is for later when you know one another's bodies and pleasures.

She may well be feeling shy and, as a result of this, tense. The solution to this is simple: love her
Truly. Love her with your heart and face and eyes as well as with your body
Don't take anything even one step one second faster than she is not only comfortable with, but obviously ready for. Talk to her. Listen to her. Listen to her body as well as any words she says.

And if she says stop, stop

Right that second.

Have lots of lube on hand (and a non-knockoverable bowl of warm water to float it in is a good idea, too) and don't be afraid to use it. Nervousness can make a lot of women dry out fairly rapidly. Dry sex will hurt her, hurt you and quite possibly give her thrush.
Pain in a first sexual experience is a serious off-putter when considering a second.

Unless you make huge amounts of precum (and perhaps even if you do) putting some lube on the glans of your penis can be very useful. 
If you are uncircumcised put it on while your foreskin is extended, let a little sort of soak in underneath the edge, then retract and extend your foreskin several times fairly gently, adding as much more lube as you like until the top inch or so of your penis is covered both in- and outside your foreskin. This should help with any pain you might feel. 
If you are circumcised there is nothing I can really say except "I'm sorry."

Another way to help minimise pain for both of you is to use your hands on her quite a lot. Finger her slowly for a while, and try using two fingers if she is agreeable. The more stretched she is the less trauma either of you will have, and hey, no one said a hymen had to be broken by a penis, did they?

Take time to explore on another.  You are two people trying to connect in the most intimate way possible. So communicate, damnit. Kiss. Cuddle. Talk. Listen. Stroke. Cry. Nibble. Laugh

Hold one another.

Be gentle. Be loving. Be honest. Be kind.

Have fun.

And most importantly...

Remember to call her next day.

A response to Daz Eddy:

Your advice to go slowly to avoid hurting the woman is well taken. There are few cases where the penis is fundamentally too large, but if the woman is nervous, insufficiently lubricated, or rushed, her vagina might not stretch comfortably. However, I do not believe that there are many cases where this causes bleeding! The blood-spot that husbands in some cultures proudly display after the consummation of marriage comes from the hymen, a thin piece of tissue that covers the vagina and is harmlessly destroyed the first time the vagina is substantially penetrated. Many women bleed when this happens; others don't; others had thin hymens that wore away throughout their youth or were broken in an accident or during masturbation or oral sex.

This writeup seems to be getting downvoted. If I am factually incorrect, please let me know! I would really hate to be confused about something like this.

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