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

Compiled, edited, and reorganized by [email protected]
with material from ([email protected] (Sharon Tsou), KAT,
[email protected] (Christopher L. Wood), [email protected]
(Atomic Playboy), and [email protected] (Raymond Peck)

STRETCH FIRST

The key is to attempting anal sex is two-fold: stretching exercises and
relaxation. This is to accomplish two things:

1) to get your virgin ass used to something inside it, and
2) to get your ass used to something as large as your partner's cock.

Stretching exercises will give you a chance to learn the needed relaxation
for the first attempt. The faster you learn to relax the muscles involved,
the easier it will be. You can use either a dildo or fingers for the
stretching exercises.

USING A DILDO

These are available at just about every adult bookstore and many
mail-order places (see question c2-6). Once you get one, you should
just practice using it. You'll probably find it easier to at least use
some lubricant, at least on the first couple inches of it (more on this
later), as well as on your asshole, and a little inside your anus.

This is to make the penetration much easier. The actual penetration of
the head of the penis is probably the most difficult part, which is why
a dildo is more realistic, and you should most likely spend a fair
amount of time getting used to it. This can either be just inserting
it up to the head, then pulling it out and putting it in again, or
completely inserting it, and then removing it. You should do it enough
until you get to the point where you feel pretty comfortable with it.
(Well, as comfortable as it can be.).

There are two steps to practice insertion with the dildo. First, you want
to insert it the "normal" way, moving and rotating the dildo around to
find the most comfortable position for you. Do it this way, so that you
know which ways are more acceptable, and which ways are more difficult or
feel a bit painful.

When you have this down, you want to repeat the "exercise", only now
trying to keep the dildo as stationary as possible, moving your ass and
body to facilitate its entry. This is a better simulation of when he
really tries to penetrate you, because (especially if you're on the bottom
and he's on the top) you really can't expect to be able to reach around
and move his cock to where you want it. You're going to have to be able
to adjust your body to his thrusts. I really can't tell you the best way
to do this, although doing it in whatever position you expect to be in
with him (on your stomach or back, for example) would probably be the
best way to also practice it.

USING FINGERS

All you need are your or your partner's fingers. Of course, you can't
have long nails. You start out by slowly pushing one well-lubricated
finger (index is best and hand lotion or vaginal juices work fine).

Slowly move this in and out, gradually pressing more against the walls
of the anus. Since an "anal virgin" will probably be nervous about this,
his/her anal muscles will tend to contract, causing pain. So it helps if
he/she/you (I'll use 'she' from now on) reads, listens to music, or
masturbates so her mind will be off her anus. After the muscles loosen
up, put another finger in along with the first, and then keep moving
them the same way. Eventually, add a third, and, usually, by the time
you can put four fingers in comfortably, an average sized penis should
be able to fit (although keep in mind most penises are *longer* than
fingers, so you may not be able to push it in as far).

THE REAL THING

USE A CONDOM AND LUBRICANT

When the time comes that you do have anal sex with him, I would
recommend having a condom. I think we all know the potential dangers of
sex (especially anal sex) when not using one, so there's no real
explanation needed.

They also help reduce the mess (although if you go to the bathroom before
this, and wash your ass with a wet rag, the inside of your rectum will be
quite clean, and you should be able to put a finger in it without it
picking up any solid particles), and you can have anal sex with a condom
on, then pull off the condom and have vaginal sex. Remember to urinate
before getting buttfucked, because this position puts pressure on the
bladder.

The next item is a good lubricant. I always use it with my one inch
thick dildo, so I have to think you would definitely need to use some
with a much larger real cock. While Vaseline is okay to use when practising
yourself, it is unacceptable to use when using a condom, since it will
start to break the latex down. KY is usually the preferred choice.

Lube up both the outside of the anus and the penis shaft (very important!).
Any lubricant that is condom compatible is ok, that means water-based.
So do not use vaseline, baby oil, or cold cream. Use KY Jelly, AstroGlide,
HR, or PrePair. PrePair is a good one because it contains nonoxynyl-9,
which is a spermicide that also can kill many bacteria. Spit is also
a viable lubricant, provided that you keep replenishing it. It
evaporates more readily than other lubricants, especially during lengthy
(ho ho) sessions, so you'll have to be aware.

GOING FOR IT: take it *slow*

Okay, now that we've got the preparatory details out of the way, it's
time to enter. You should proceed VERY slowly. Place the head of
your penis against the anus, and then, apply a SMALL amount of
pressure so that the penis enters very slowly. It is important to
maintain control on entry because if you apply too much pressure and
the anal muscles just 'give way' it could hurt like hell. Once you
two become accustomed to doing this, it will become much easier.

Getting inside may take anywhere from 15 seconds to 15 minutes. Don't
be impatient! If you push too hard or go too fast, you can tear her.
This isn't really serious, but it'll surely end you fun for the day! She
may want you to ease up on the pressure at times to allow her body to get
used to the opening. When she gives you the go-ahead, it often helps to do
a bit of short stroking, starting with ~1/8" and going to maybe 1". When
you start to slide inside, she will most likely open up and relax better.
Don't start out thrusting, just gently move back and forth, or just get
it inside and rest it there until she's used to it.

This is the most important part for her comfort and pleasure. Basically,
you apply a bit of pressure, and as she relaxes she will let you in.
Sometimes the act of her "pushing out" (like defecating) will relax her
sphincter. After you become more used to it, a slight (~ 1/4") pumping
of the pressure will let her open up faster.

Sometimes she will find it painful for you to go in all the way:
it's similar to hitting the cervix. Don't go in all the way!
Just be very gentle at bottom of the stroke 'till it eases up.

After a while, if she is properly relaxed, you should not need to be
gentle: you can pump away with mad abandon. In fact, some find this
most stimulating. I pump all the way in, and then all the way out,
pulling completely out of her for a moment (although not too long, 'cause
she'll start to contract right away).

OTHER STUFF

Never switch orifices (i.e. going from anal to vaginal play) without
carefully washing with soap and water. Bacteria from the colon can cause
nasty vaginal infections. If you are using sex toys (dildos or anal plugs)
cover it with a condom first, so you can simply pull off the condom and
put on a fresh one to use on another orifice or another partner, provided
that you don't have contaminated lubricant oozing all over the place.

You may or may not be need some type of pillow. This is basically to
prop under the ass or lay under the stomach to make the angle of
penetration a little easier. Whether you need this will depend on
where you have sex (it may be impractical to bring one, or the positioning
may be good enough already).

If you are into learning from pornography (and if you just want a good
laugh ;-)) I would suggest that you check out Hollywood Video's "The
Best of Caught From Behind: Part II". It's very pornographic, very
informative, and very funny. It's up to you though.

POSITIONS

As for positions, it's usually easiest for insertion (unless she's
*really* excited!) in the spoon position. This also gives you access
to easily stimulate her in other ways. Be careful not to transfer anything
from the anal region to the vagina: this can cause infections. I usually
keep a set of fingers or a hand "clean" for this purpose. This is also, of
course, important for non-intercourse anal stimulation, such as cunnilingus
with some fingers rubbing, some inside her vagina, and some in her anus.
Keep those fingers partitioned!

We usually switch to "on the knees-face in the pillow, her pressing hard
on her clit and pubic bone", to avoid severe abrasion burns! ;-) Spoon
position allows her more control over initial insertion, while the other,
well, it has its own advantages!

The other positions, after initial insertion, to face-to-face, with her
legs on my shoulders. This really allows some serious depth.

The position depends largely on how well you two fit together. If you
are tall and if your SO is short, you might want to try having her lie
flat on her stomach. You could also have her lie on her back with her
knees drawn up. In this situation, it might be a good idea to place a
pillow under her buttocks (depending on what the two of you like). If
dimensional factors permit, she could also be on her hands and knees.