Your first experience doing something strongly affects your future expectations of enjoyment, and anal sex is no exception. You can truly enjoy the first time you try anal sex by training your butt first.
Prepare Your Anal
Preparing your ass really just means indulging in a bit of self exploration. You need to get used to how anal penetration feels and the stretching that goes with it. Here's why you need to train your ass before trying anal:
When there's two of you and your butt is in play, you need to be able to explain what you want. If you don't know your body, you can't communicate effectively.
If you don't know your body, you're likely to underestimate how much more carefull you need to be with anal sex (compared to PV sex). This can lead to injury.
Self knowledge and experience gives you confidence to relax with your partner. It's difficult enough to get something as large as an erect penis up there without stress or fear clenching muscles you don't need clenched.
The first time you put something up your butt, it can feel pretty strange. If it feels like a visit to the doctors, you aren't likely to enjoy it. If you're used to it then it'll be arrousing and sexual.
Every sex expert worth their salt recommends learning about your own sexual responses before having sex with another person. In other words, mastering masturbation before trying sex will give you a better first-time sex experience.
This strong logic seems to be forgotten - slipping through the authors fingers like a fist full of the lube they confidently preach you should use to excess - whenever talk turns to anal sex advice. But the truth is that people who already know about their own ass, what feels good and what doesn't, are the ones who enjoy anal sex.
Just like with "normal" masturbation, you need to learn about yourself - in this case, your ass. Find out what you like. Learn what makes you feel good and very importantly, what might hurt you.
Preparation is Knowledge
As you explore, you'll gain a working knowledge, backed up by a theoretical anatomical understanding of your asshole.
You'll learn how long it can take to get even just a finger in, what angle works, how aroused you need to be before you even want anal stimulation. For some, anal play can feel good any time. For others, it's something that only gets the green light after the first, second, third orgasm. Everyone is different and you should know your personal preferences.
You'll learn the difference between ok pain and real pain.
What I call ok pain is the type of pain you can endure without causing any injury. For example, sometimes it can hurt to stretch (say, before running), but we all know stretching is good for you, as long as you don't stretch too hard and strain a muscle. Some discomfort or soft, ok pain can be pushed through to find pleasure on the other side. Other real pain is an indicator of real or potential injury.
You'll learn how different your ass is to your vagina. Your ass doesn't get "wet" like your pussy does when you're aroused. It doesn't stretch to accommodate over-sized penises when you're aroused. It needs special care and it's better to learn this when you are by yourself. You will have much better first-time anal sex if you have a personal working knowledge of your own anus.
Knowledge Helps Communication
Once you know how your body reacts to different types of anal stimulation, this will enable you to communicate properly with your partner.
Communication - being able to explain what you physically feel and more importantly, what you want your partner to do - changes your role from passive to active.
Don't just let sex happen to you. We enjoy sex more when our partner enjoys it too, so being an active participant and pursuing your own pleasure (as well as your partner's) makes for better sex all round.
When in the receiving role in anal sex, you are the co-pilot. Do not discount this role. If you've never even put your own finger up your ass - if you don't know what feels good or bad, you can only react to what is happening.
"Ouch, no, don't do that. Ah! No, that doesn't feel good either...."
If you've taken a few exploratory walks by yourself down the hershey highway, you'll be a much better guide and can give advice and directions based on what you know is going to happen.
"Ok, slow down... No, much slower. Yes, that's good. Right turn up ahead.."
Self-Knowledge is Confidence
Sometimes it is hard to say "No."
In the heat of a sexual moment, when your partner is telling you "It's almost in!" or "You can do it." you might hesitate or even just grit your teeth and endure it. He knows, right? Pain is normal, right? Maybe it will be ok? But... maybe not.
The most important part of an enjoyable anal sex experience is having the confidence to say "Stop." Self-exploration and self-knowledge of your body let you confidently say exactly when you need to stop.
When you know the normal type of stretch your asshole can take and it's limits, you can quickly react with confidence, regardless of any self-interested assurances the man with the cock about to penetrate your ass is giving you.
How to Prepare for Anal Sex
Here's how to prepare your ass for anal sex in the long term:
Get to know your ass as an erogenous zone.
Learn exactly what your ass can and can't do.
Prepare your asshole to take a real penis.
Learn What Feels Good
The first step in training your ass is the meet and greet. Up till now, you've may only have touched your asshole when wiping or when washing in the shower. In other words, never in a sensual manner.
But your asshole is an erogenous zone. Here are some tips for getting to know your asshole as a source of sexual pleasure:
Touch your asshole while masturbating. It's important to approach touching or fingering your ass as a sexual activity. While masturbating, you're aroused and anal masturbation should be part of that feeling.
Even when only touching outside, use something as lube - saliva, moisturizer, oil, real lube. I've even used hair conditioner when including solo anal play during a shower masturbation session.
Don't approach fingering your ass like a doctor and just put your finger right in. Approach it like a lover and prelude it with lots of body touch, especially your buttocks.
Don't force a finger up there, rather massage your finger into your asshole and through your anal sphincters.
++++++++++++++ WRITE AND LINK TO HOW TO FINGER AN ASSHOLE +++++++++++
Learn Your Limits
You may be surprised what your ass is able to do, especially given time. But there are limits; and ignoring them will usually be painful and occasionally require a doctor's attention. Learn your limits so you never accidentally exceed them.
After you're comfortable with a single finger, you could then try:
A slim dildo
A butt plug
Move up in size gradually. You may come to find that as you approach previous limits that caused real pain, you now feel a pleasurable stretch as your sphincters open. You're ass is becoming more malleable and able to take more - if you had've tried with the same size insertion as a beginner, you'd have injured yourself.
But you're not just building up your asshole's abilities, you're learning it's limits and how to recognize ok pain from real pain which lets you avoid injury.
You're learning more about what feels good and how to make yourself feel good - key knowledge when it comes to communicating with your partner about how to make anal sex work for you.
Learning the limits of what you're comfortable taking up your ass isn't only about size, it's also about knowing how long things take, how quickly you can progress from finger to cock, how aroused you need to be before you can even start enjoying anal play (which you should never do if you aren't going to enjoy it).
++++ WRITE AND LINK TO ARTICLE NEVER DO IT IF YOU DONT WANT TO, BAD SEX PARTNER +++++
Preparing Youra Fora
You've figured out that your ass can be a source of sexual pleasure. You're learning your limits and know enough to avoid real pain and injury. The final step is getting your ass ready to take a cock.
The best way to do this is to try inserting something penis sized. Thickness is the most important aspect but it is also good for your future enjoyment of anal sex if you have an idea about how the length of a penis might feel too.
If you have a dildo with a flared base or realistic balls included in the mold, try inserting it up your bum. If you can do it, you're ready to try anal sex.
A lot of people don't bother buying dildos and use things from around the house. This can be dangerous. The list of thing people stick up their butt for fun include:
Slim plastic bottles
Slim steel containers
So much more...
The problem is sometimes, with all the lube, people lose their grip and the object slips right up there. For the list of things people have to visit the hospital to have removed, see the list above. You may also want to read the common sense rules of anal toys.++++++++++++WRITE/LINK++++++++
If you do choose to use a plastic bottle or similar, at the very least, cover it a condom to keep the it somewhat clean but most importantly, to avoid introducing unwanted bacteria into your rectum.
Never, ever put glass up your ass. Never!