What should I do to make (the first attempt at) vaginal sex easiest?

FOR THE VIRGIN FEMALE:

1) Do it in a place where she feels safe, ideally in her own bedroom.

2) Do it at a secure time, when roommates won't come barging in, a firedrill is unlikely, etc.

3) Simulate it in advance:
a. Go almost all the way.
b. Practice the thrusting motions of sex while fully clothed.
c. Have her give you a "hand job" so that she will know what your body does when you have an orgasm.
d. 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 it 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."
a. Nothing that can possibly upset the stomach.
b. 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 the buttocks 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.

12) 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. I'd say 10-30 minutes is a good range, but it is actually going to vary a lot depending on the particular couple involved.

13) Take forever, if necessary, 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.

14) 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.

15) 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.

16) 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.

17) 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.

FOR THE VIRGIN MALE:
(from: Carole Ashmore)

OK. This is on the assumption that he's told you it's going to be his
first (some men tell you *afterward*) and that the two of you are
not first-timers fumbling together. In the both-first-timers
case I recommend strong egos, mutual respect and affection, and a
great sense of humor. Also theoretical knowledge *helps*. Read the
fucking manual. (Sorry I just couldn't resist the play on words.) I
recommend anything by Alex Comfort; THE JOY OF SEX and THE FACTS OF
LOVE are very good.

But on the assumption that he is a virgin and you are experienced:

1. There is a socially prevalent notion that men make love and women
are made love to, so an experienced woman with an inexperienced man
is going to be gritting her teeth enduring his fumbling ineptitude.
*Actively counter this notion.* Tell him the thought of his being
a virgin makes it a special and especially delightful encounter for
you. Tell him the thought of initiating him into the joys of
love-making is *very sexy for you*. Strongly convey the notion
that you expect to have a great sexual experience based on his
attractiveness, his enjoyment, and *your* skill. Make him believe
that he has no responsibility for 'making this work' and can just
enjoy it.

2. Take the initiative physically. You kiss him, don't wait for him
to kiss you. You start undressing him. You make the move in the
direction of the bedroom. ETC. On the other hand, don't insist
on the initiative if he takes it eagerly -- be appreciative,
encourage it, but don't go limp and assume he'll take it from here.

3. Tell him you find at least one thing about his body particularly
attractive. Stay away from "You have beautiful eyes.", but almost
anything else will do: Tell him you love men with hairy chests,
or tell him he has a great ass, or tell him men with strong hands
particularly turn you on, or tell him you love the way he
smells, or tell him running your fingers through his hair is *so*
sensual, or . . . something *specific*, not just, "You've got a
great body." or "You're so sexy." After you tell him this, *show*
him -- run your fingers through his hair, enjoy grabbing the sexy
ass, etc. as appropriate.

4. Tell him you find at least one thing he does particularly
attractive -- again, it is the *specific* thing that is believed
and appreciated. "I love the way you kiss." or "Yes, touch me
exactly like that." beats the hell out of "You're a great lover."

5. He's going to be convinced he was either too fast or too slow --
the chances of simultaneous orgasm after whatever the culture has
led him to believe is the 'proper' amount of time are just about
nil. So be prepared ahead of time to convince him that this:
A. isn't a problem B. happens to just about everybody. For
'too fast' tell him the first time just takes the edge off and
he (not you) will have more time to enjoy the next session of
lovemaking -- and meanwhile he has this wonderful opportunity (of
*unspecified* length) to learn what pleases you while he's not so
distracted. Assure him that you consider 'not being too distracted
while learning' an *advantage* in lovemaking. For 'too slow' tell
him you *enjoy* prolonged lovemaking -- either it gives you a
chance for more than one orgasm or it gives you a chance to enjoy
the wonderful sensuality of post-orgasmic sex. If it's obvious
that it's too slow for him, that he's not going to make it if he
keeps at it for the next two hours, let him know that he gave
*you* a wonderful time and that everybody's nervous the first time,
he'll be more relaxed and ready to enjoy it in the morning.

6. Tell him you want to sleep with him again; don't assume he knows
it -- don't make him ask, you ask.