Anal Sex First Time:
How To Get Started At Anal Sex


Hi ladies! Are you considering having your anal sex first time? Great! A whole world of new pleasure is ahead of you; but first, you must get well-informed about the precautions you and your partner must have, in order to have a pleasurable experience, instead of a painful one. (Guys click here)


Hi ladies! Are you considering having your anal sex first time? Great! A whole world of new pleasure is ahead of you; but first, you must get well-informed about the precautions you and your partner must have, in order to have a pleasurable experience, instead of a painful one. (Guys click here)

Anal sex is one of the biggest sexual fantasies for most men! And one of the things most women are afraid to try...

Therefore, if your man is fantasizing about it, and he’s trying to convince you to try it, but you're afraid of it, or even if you're also curious...

The best thing you can do is to first get informed.

Anal sex requires certain preparation and some precautions that both, you and your man, need to take care of, to be able to enjoy anal sex.

Anal sex can be quite pleasurable or quite painful... Depending on how it is performed.

This article will explain you all the main things you need to know before having your anal sex first time and start enjoying the very erotic world of anal sex.


1. Get informed

Either you have tried anal sex before or not, getting informed first about the proper way to perform this sexual activity is a MUST! This goes for you and for him, but keep in mind that he’s basically the one who will have the main control of the situation; therefore, make sure he knows what he’s doing because he can hurt you if he doesn't do it right.

There’s a number of things that you guys need to do as anal-prep. As well as, there some things that you need to keep in mind during the practice of this sexual activity.

First, you must know that anal sex is very pleasurable, but it must be done very carefully, or it will be quite painful. Your partner must be very well informed about how to do it properly and gently, to not end up hurting you.

No matter how much he wants it, don’t let him pressure you. Take your time, and try it only when you are sure about it, and you know you can trust him.

Remember, you’re letting him enter you through a body part that wasn’t designed for penetration; therefore, it can be quite painful if it’s done wrong.

Actually, even if it’s done right, you need to know that it’s quite uncomfortable at the beginning. You must past through the somehow painful initial stage before being able to feel pleasure.

Read all the info I have about anal sex in my website, and take a look at “Anal Pleasure For Her” to learn about everything you need to know for safe and pleasurable anal sex. Make sure he reads it as well! Send him this link Anal Sex Tips: How To Make Anal Sex Pleasurable For Her Instead Of Painful.


2. Communication

Communication is very important in the couple’s sex life, but when it comes to anal sex, it’s crucial.

First of all, if he tells you he wants to try anal sex, ask him why and how he would perform it. Make him describe you what he would do, with all the info you’re reading now, it will be very easy for you to know if he really knows what to do.

Now, let him know about any concerns or fears you may feel about it, and listen to what he has to say. Pay attention about how much he knows about the topic, and how well he eases your concerns. Remember, you need to trust in him, and feel comfortable enough to try having anal sex with him.

If he makes you feel secure enough for you to know that he knows what he’s doing, and that he will properly take care of you by being extremely careful and gentle, then go ahead and give it a try...

... But, if it’s obvious that he doesn’t know much about the proper way to have anal sex, and he shows you that he’s so excited to try it that he may end up rushing things, then make him get informed first before letting him having anal sex with you.

So remember, before agreeing to have your anal sex first time with him, make sure that:

1. He knows what he’s doing.

2. He will be patience to wait until you’re ready.

3. He will take all the precautions needed for your experience to be safe and as comfortable as possible.

4. He will be extremely careful, slow and gentle to not hurt you.

5. He will stop anytime you want to.


Depending on how much confidence he gives you, and how much he shows you that he’ll take care of you, is that you can decide to try it or not. It’s always YOUR decision.

Besides communication before engaging in anal sex, communication during the sexual act is also required.

Anal sex will be successful and pleasurable depending on how good you guys communicate during the process. You always need to tell him what feels right and what feels wrong, and make sure he’s willing to follow your directions.

No matter how aroused he is, if you say “slow down”, he MUST do it; if you say “it hurts or stop”...  He MUST stop!.. Because he can really, not only hurt you, but also damage something inside or outside of your anus.


3. Anal prep

Yes, anal sex can really hurt, but it doesn't need to, if you do things right. In fact, other than the initial discomfort, if it hurts... You guys are doing something wrong! 

To minimize the discomfort and the pain, there’s some anal prep that is needed to be done before and during this sexual activity.

The first few times will be the ones that may hurt the most, while you and your anus get used to the new sensation of having something “foreign” going inside; however, no matter how experienced you guys get, you never should skip the following anal preparation:

1. Use lots and lots of a good silicone-based anal sex lubricant.

2. Choose a comfortable anal sex position for you that allows easy access. Doggy style and elevated missionary are the best options.

3. Relax!!! Make sure he takes his time to warm up your body with lots of foreplay. Massages, oral sex, and analingus are great options.

4. Anal fingering is the best warm up for the area of your anus. His fingers will prepare you to get used to the new sensations, as well as, prepare your anus to accommodate something bigger... His penis.

Now, you can take anal prep one step further and get extra clean before the anal sex session. Your regular cleaning habits should be enough, but if you want to make sure you're completely clean you can use an enema.

This is not required; it is more of a personal choice that make things more comfortable for both of you. Just don’t use enemas too often because frequently douching can dry out the anal canal.

Keep in mind that either you use an enema or not, the real function of your anus is not sex, so things can get messy, and you and your partner need to be aware of that and be comfortable enough about it.

Normally, it shouldn't be a problem, well fecal matter is stored in the vowel not in the anal canal, but if you want to feel extra comfortable, go ahead and use an enema. You can do this on your anal sex first time to make you feel more comfortable, and later any time you feel like it.

As a tip, make sure you include lots of fiber and water in your diet to keep yourself regulate.


4. Engage in anal play before anal sex:

Anal play is a good introduction for you to get used to the new sensations outside and inside your anus, as well as, a great transition between the warm up and the actual anal sex.

Actually, anal play is the proper way for him to warm up your anus before introducing his penis.

Here are the different ways he can use anal play as a warm up for anal sex. 

He can choose one or use them all. The best way he could do it is to use them all progressively. Either each one in separate times to introduce you little by little to anal sensations, or all at the same time to gradually build up your way to use his penis.


- Anal fingering

- Anal sex toys

- Analingus


1. Option: He can start by giving you oral sex while stimulating your anus with his well lubed fingers.


2. Option: He can go from oral sex to analingus (licking of your anus and all the area around it). If you both are comfortable with it, this is a very pleasurable prelude to anal sex.


3. Option: He can stimulate your anus only with his fingers using some of the anal fingering techniques. This will prepare your anus to accommodate his penis, and will help to turn you on very much. Anal fingering should always be part of the anal warm up, indifferently of any other kind of anal warm up he’s using.


4. Option: He can use small anal sex toys to start getting you used to anal penetration, with something smaller than his penis.

The advantage of these toys is that these are less intimidating than a penis, and some of them have vibration, which you will feel very pleasing. Let yourself discover the new world of sensations that anal play can offer.

Remember to always buy anal sex toys that have a wide, flared base, a cable or ring on the bottom that keeps the toy from sliding too far into your anus.

Engaging in anal play before attempting anal sex, will let you gradually get used to the new sensations around and inside your anus. Also, it will help you ease the discomfort of the anal stimulation; with every occasion you will be more relaxed and the discomfort will be less, so when you’re finally ready for full anal sex, your body will be already used to the feeling of penetration, and it will less painful.

You will be able to start enjoying the pleasure of anal play, start liking it, and increase your curiosity and anticipation for anal sex.

Also, your tension will significantly be lowered the first time(s) by knowing that he’s just gradually playing a little bit, here and that there, and it won’t be a full penetration of his penis yet.

Remember, the more patient he is in this process, the better chances he has for you to want to feel his penis, and the more comfortable the experience will be for you.


5. Lots of warm up to get relaxed

Once you feel you’re ready, mentally and physically, to fully experience anal sex, let him indulge you with plenty of warm up to relax you. This is crucial.

When it comes to anal sex, he MUST warm you up to relax you!

The more you’re relaxed, the more the muscles of your anus get relaxed, and the easier the penetration will be.

Tell him to do everything you love to get you the more aroused and relaxed he can. Take your time and enjoy all the kisses, caresses, massages, licks... As a tip, oral sex and analingus are great here.


6. Anal fingering first... Always

Because anal sex is a new experience for you, the proper way for him to introduce you to the pleasurable world of anal sex is first using his fingers NOT his penis.

In your anal sex first time, he should only give you anal stimulation with one finger at a time, starting with his smallest finger, and work his way up to the middle finger, letting you get used to the sensation.

First, he should press the opening of your anus with his finger, then with his palm up aiming to your front wall,  he should insert only one knuckle in and stop, to let the anus expand and make more room for his finger.

Now, he should insert the second knuckle and stop. Finally insert the third knuckle and stop again.

If you’re ok with the stimulation, he can go ahead and move his finger in a “come hither” motion to stimulate indirectly your G-Spot.

YES! He can actually stimulate your G-Sop indirectly through your anus because there’s only a thin membrane separating your vagina and your anus canal.

He should start the movement slowly and increase a little bit of the pressure to give you your first anal orgasm! He should let you enjoy the sensation and discover the pleasure of anal sex, and stop for that time.

The second time, he’ll do the same, but after warming you up with one finger first, he will go ahead and insert two fingers at a time, one on top of the other not side by side. He should follow the same process described above to try to make you orgasm, and stop anal stimulation for that “night”.

The third time, he’s going to warm you up with one finger, then two fingers, and then he could try to use his penis if you’re ready for it:

So, in the third time, after using his fingers to warm up and prepare your anus for a bigger penetration, he will start with his smaller finger and work his way up to his middle finger.

He must use lots and lots of lube and perform the best anal fingering techniques to relax you and “open” your anus.

If he manages to give you an orgasm by finger stimulation, it will be even better!... You will be more relaxed to receive his penis, but don’t sweat it!... Don’t force it to happen; concentrate on relaxing to feel the less discomfort as possible.

Now, he will go ahead and insert his second finger and give you some good stimulation to prepare you for his penis.


7. Gradual, slow, and gentle penetration

Once you’ve been able to handle the full stimulation of his middle finger, you may be ready to try his penis.

If you couldn't handle his bigger finger, don’t even let him try introducing his penis because it will hurt you. Stop, and try anal play some other time. Only let him use his penis when you see you’re ok with his finger or a toy.

If you feel you’re ready for his penis, make him put lots and lots of lube in your anus and his penis, and let him start pressuring very slow and gentle to introduce only the tip of his penis.

Tell him to take his time, stop, and give you some time to get used to, and if you’re ok, let him go a little bit further inside; have him to stop again, and keep going a little bit further - only as far as you’re able to handle without pain.

Normally, a little bit of discomfort is felt at the beginning, while his penis is passing through the first sphincter, but after that, it should not be that painful, maybe some discomfort but not painful. If it hurts, stop and try some other time.

With time and practice, the discomfort will be less and less once your anus start getting used to the penetration.

Remember, once inside, tell him not to thrust too hard or too fast because he can hurt you, causing you pain, and even maybe some tears outside and inside your anus.

In your anal sex first time(s), do not concentrate on having an orgasm; you just need to relax!... The orgasm will come with time, once you’re more used to anal sex, and you’re able to get relaxed enough to start feeling pleasure.

The first few times concentrate on relaxing to get the less uncomfortable experience as you possibly can, for you to be willing to keep trying and reach the quite pleasurable stage that anal sex offers.


8. Finish it up the proper way

When it comes to anal sex, his orgasm is not always the big finale. Here, the end comes when you say that’s all you can handle. The first time, it may be even only his finger the only one who had a bit of a chance to get in. Maybe his penis made it, but only for a short time.

Some other times, he may get the chance to go deeper, and slowly do some strokes. If you guys keep trying (not every day of course, give yourself time to want to try again) at some point, he will be able to give you anal sex orgasms, and you will let him go all the way until he orgasms too!

Patience and practice will get you both there, but in the meantime the finale is when you say stop.

After you guys are finished, you both should get cleaned up with warm water and soap. Now, as far as what went inside, if you used a silicone-based lubricant, it will all be flushed out with your next bowel movement as long with the semen, if he ejaculated inside of you.

For extra cleanness, you can use an enema afterwards, but this is not completely necessary; it's more of a personal choice.

Remember, that if you guys decide to stop anal and switch for vaginal or oral sex, make sure he changes the condom and/or clean his fingers, penis and mouth with water and soap before getting close to your vagina, to avoid spreading bacteria and give you a vaginal infection.

Now, if the first attempt wasn’t successful, and you guys call it off for the "night"... Don’t feel discouraged! Remember this is a process, it can take some time for your body to get used to anal sex.

You can always try some other time. Work on getting even more relaxed by taking more deep breaths, and having him increase the foreplay.

Remember, you can always stick with some anal play first, and later give anal sex another chance.

However, if the reason why it was not successful was because your partner rushed things out and penetrated you too fast or too hard making it painful for you, then talk to him and don’t try again until you’re sure that you can trust him.


With all of these recommendations and precautions, I know it might sound a little bit discouraging to try; however, keep in mind that the kind of pleasure you could feel from anal sex, it can be even more powerful and intense that vaginal or oral sex; you only need to make sure that you guys handle it with caution.

Be smart and responsible, and learn all you can about anal sex. The best source that I've found to recommend you to get ALL the information you need is Anal Pleasure For Her by Gabrielle Moore.

This is the most complete guide for Anal Sex that I have found so far. However, I must tell you that it is directed to men - it actually teaches men how to give anal pleasure to their woman CORRECTLY - but, I needed it to recommend this guide to the Ladies too because you all MUST know this info!

It is true that when it comes to anal sex, your man is pretty much in charge, BUT you need to know what is going on back there! You NEED to know how to guide him correctly so he doesn't hurt you...

Specially with anal sex, you MUST be well informed. This is a very delicate area and you need to make sure that he's doing things right. 

Remember: Anal sex can be very pleasurable or very painful depending on how it is performed!

Make it a pleasurable experience! Learn about anal sex and make sure your man learn how to perform it properly... and then, give yourself the opportunity to experiment the erotic world of anal pleasure and get mind blowing anal orgasms!...

... Yes! It is possible!... If you guys carefully and patiently follow all of the process explained above, and learn more about anal orgasm techniques, he would be able to give you the best anal orgasms of your life! So, go ahead and take a look at Anal Pleasure For Her here.


Angie :)

Connecting you with the best love and sex advice for a healthy relationship!



Next: Dangers Of Anal Sex: Uncovering The Myths... Is Anal Sex Safe?... Dangerous?... Painful?

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