How to Have Anal Sex: Preparation, Pain, and The Experience

If it hurts, You’re doing it wrong!

Ancient illustrations of sex clearly show anal stimulation, and perhaps for that reason, it has often had a featured role in the way various sexologists have taught modern sex, even though the topic is controversial and turns many people off.

I was interested to find that roughly a third of the couples I talked do incorporate some form of anal stimulation or play into their routines.

However, I’ve left it out of the instructions until now because it’s clearly optional and it does trigger some very negative reactions.

Taboo, Mess, and Pain?

The negative reactions are understandable. We’re all taught that poop is dirty, smelly, nasty, and dangerous, and there’s a strong taboo about talking about it and where it comes from.

Furthermore, a fair number of women have had at least one painful experience with a partner who forced anal penetration on an underlined, unprepared, and unenthusiastic woman, and hurt her badly.

The nerves around the anus are among the most sensitive in the body, so pain in this area can be excruciating. On the other hand, these nerves have the potential for strong pleasure as well.

As is often the case, knowing what you’re doing makes all the difference!

Your Guide

Rather than trying to summarize the necessary info in inadequate space, I’m going to refer you instead to Ultimate Guide to Anal Sex for Women by Tristan Taormino.

I strongly recommend that you read it. It’s thorough, clear, and excellent. In spite of the title, the info is equally applicable to men.

If you are determined to experiment on your own, all I can suggest is that you follow common sense and good hygiene, take it very, very slow, use way more lube than you think is necessary, and always remember,

Rule #1:

If it hurts,

STOP!

You’re doing it wrong!

What it was like?

Among the couples I talked about, anal penetration with penile thrusting was the rare exception. Most women, however, did like sitting in yab-yum position with anal penetration and did it fairly often.

They said, in the words of one, that it created,

“tighter, firmer, stronger connection”

than vaginal penetration and that their partner’s erection lasted better with anal penetration during the relative immobility of yab-yum.

A couple liked to use a vibrator slipped between her and her partner while staying in that position.

The other two said they liked to segue from anal yab-yum into “back-door cowgirl,” with a lot of clitoral stimulation (hand or vibrator), having multiple anal/clitoral orgasms before switching to vaginal sex.

Please note that;

• Use condoms for anal penetration and carefully remove the condoms before having vaginal sex.
• Having a paper towel handy makes safe removal much easier.
• Wrap the towel around the condom, slide it straight up and off the penis, and throw it away.)

Fingers

Using fingers and various anal toys for anal stimulation was far more popular than penile insertion. Some couples limit anal play to finger massages of the external area or minimal finger insertion.

One woman said she liked insertion during yoni massage;

“But only the first joint of his little finger.”

One of the men said his wife inserted her thumb and;

”She used it kind of like an anchor,”

Tugging on the curled thumb as she tickled and stroked his perineum, balls, and lower shaft with the other fingers of that hand. On the other hand, two of the men like rather a deep prostate massage during and especially at the very end of the lingam massage.

Toys

Two types of anal toys were most popular, and both come in versions with and without vibrators.

It can be described as “like beads on a stick” consisting of round balls joined together, in some cases by small tubular sections. This type is usually molded all as one piece of plastic, with a ring, handle, or flared base at one end and a small ball-shaped tip at the other.

Inserting or removing this creates a series of stretching sensations as the spherical sections are pushed or pulled, bump-bump-bump, through the anus.

You can think of it as a slim, but very bumpy, anal dildo.

Buttplug

The other favorite is called a “butt plug” a vaguely pear-shaped plastic or rubber item with a narrow neck joining the wide base of the pear to a ring, handle, or flared base.

The main part is lubricated and slowly pushed through the anus, which then closes around the narrow neck at the bottom, holding it in place.

The fullness and pressure this creates feel good to many people, and the handle allows the wearer’s partner to manipulate the toy, stimulating the anal nerves, without having to worry about sanitation issues.

It’s Better Then Vaginal Sex

In addition, the plug stimulates a man’s prostate and puts pressure against the back wall of a woman’s vagina, pressing it toward the front wall and narrowing the vagina, thus increasing the amount of sensation when a finger or penis is inserted.

If you’ve ever noticed that vaginal sex is sometimes weirdly better;

When you’re constipated and your rectum is full, you might want to try a butt plug to recreate that feeling.

Several couples routinely insert his-and-her butt plugs before the start of Tantric Sex and leave them in the whole time to allow for spontaneous anal play at any time without mess or fuss.

They say that once you are used to them, they’re very comfortable.

Prostate Massage

A few couples used a third type of anal toy, a prostate massager. This is generally a slim curved rod made of stainless steel, tempered glass, or fairly hard plastic, with a smooth, round tip.

The tip is inserted into the man’s anus, and then the curve of the rod makes it easy to press and rub the tip against the prostate, which is located under the front wall of the rectum at the outlet of the bladder, behind the perineum.

Sanitation

Toys allow the benefits of anal play without the sanitary problems involved in putting fingers or a penis inside the rectum. Those who prefer fingers all use condoms, gloves, or finger cots to cover their fingers.

Whichever you do, just be sure you have paper towels or other appropriate materials available so that when you remove toys, condoms, or gloves from the anus you can wrap them in something that will contain any mess in a sanitary way.

Some advice;

Be very cautious about using excess lube or massage oil near the anus, especially while the receiver is;

• prone (face down)
• or in the “face down with butt in the air” position.

This applies to everyone, but especially to those who are inserting toys or fingers.

Use Enough Lube

Given the importance of using enough lube in this area, it’s easy to slosh too much on and forget that it is going to flow downward from the anus, carrying bacteria with it.

Even if the lube doesn’t carry bacteria directly into the vagina or down to the tip of the penis, it can still easily contaminate the perineum or the butt cheeks, which will then contaminate your hands, which will then carry the bacteria to other places where they definitely aren’t wanted.

Wipe Properly

The point is that everyone needs to keep tissues, hand wipes, paper towels, or old diapers handy so that excess lube can be wiped up promptly. And it’s not a bad idea to have a hand sanitizer or alcohol wipe handy and use it on hands and on areas like the perineum if there has been any risk of contamination.

Oil Dissolves Latex

If you use latex condoms, gloves, or finger cots, do not use any kind of oil nearby. You need to use water-based or silicone-based lube instead.

You can still use massage oil as long as you stay clear of the anus and anywhere else you plan to use latex, and as long as you get all of the oil off your penis or fingers before putting condoms, gloves, or other latex items on them.

Use nitrile lab gloves;

• No latex allergy,
• Cheap,
• Resists to oil much better.

Female Condom (FC2) for Anal Play

If you do anal penetration, whether it’s with toys, fingers, or penis, use the FC2 “female” condom.

It’s much more sanitary than going bare and is much less likely to get lost inside the rectum than a regular condom.

In addition, when used for full penile penetration, the friction is between his penis and the lubricated inside of the FC2, instead of being between the condom and her anus/rectum, which is much harder to lubricate properly.

So he gets more pleasure with the FC2,

And she is protected against abrasion and pain from being underlubed.

Tips:

• Grip the inside ring with a cloth or paper towel to squeeze it before insertion, otherwise, it can get away from you.
• Stick a finger or a slim, smooth rod or anal dildo inside the condom to aid insertion.
• Alternatively, you can remove and discard the inside ring first. That makes putting it in much easier, but it also makes it more likely to slip out during sex, so you will need to be more careful about force and angles. (This can be the way to go if you didn’t get a chance to put it in beforehand.)
• The FC2 is made of nitrile, not vinyl or plastic, so you can use any kind of lube — water-based, silicone, or oil.
• It comes with a lot of lube on it. Get some of it on your fingers and slather it on your butt. Use just enough lube on the outside of the FC2 to get it into place comfortably, and then wipe up any excess on the outside.
• Be sure you have a lot of lube on the penis and/or inside the FC2 when you’re ready to start using it!

All of this applies equally well to men who like anal toys, fingering, and prostate massage during sex.

From: How to use the FC2 for anal sex

• Use lots of lube!
• Make sure the FC2 is inserted straight.
• It should be smooth against the walls of the vagina or anus…
• DO NOT USE AT THE SAME TIME AS A MALE CONDOM!

Practice, practice, practice!!

Think of other frustrating firsts like inserting a tampon, putting in contact lenses, or first time having sex?

Remember:

It Takes Practice!!!

Also, the FC2 can be put in place well in advance and left in place after you’re finished, to be removed at a later time.

This means that a man can switch between fingers and penis, and the partners can alternate between anal and vaginal sex, or even between anal and oral, without having to remove the FC2, deal with a mess, or worry about cross-contamination.

If the male partner ejaculates inside the condom, it’s a good idea to twist the outer ring several times after he withdraws to avoid dribbling and leakage.

Being able to include anal fingering in the middle of a yoni or lingam massage without concerns about contamination is a BIG advantage, and this finally provides an answer for couples who like sitting yab-yum with anal insertion but want to finish with vaginal sex without having to stop for a big cleanup.

Don’t Push

I am definitely not urging anyone to experiment with anal play if they are deeply uncomfortable with the idea. But there are also people who try it and find it enjoyable but only occasionally worth the extra effort.

And, of course, there are many others who never get past the “Ewww!” factor.

Relax & Trust

However, the critical thing is that both of you need to be on the same page about this. If you’re interested and your partner is grossed out by the idea, just quietly let the matter drop.

Remember that Anal Sex completely depends on deep relaxation and trust.

Pushing your partner to do something that he or she finds uncomfortable or repugnant will just break the mood, violate that sense of trust, and completely mess up the experience for both of you!