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The Curious Guy’s and Gal’s Guide to First Time Anal Sex

first time anal sex

There is probably no sex act more maligned, misunderstood, and feared than anal sex. Use these tips and do it right for a mind-blowing experience!

There are a lot of false assumptions about anal sex, and the worst one is that it’s supposed to hurt.

The very idea strikes fear into the hearts of countless women, and it’s assumed that the only reason to ever do it is because one’s boyfriend or husband really, really wants to.

This could not be further from the truth. When done right, anal sex can be incredibly stimulating to the woman *or man* who is receiving it. Of course, the assumptions don’t come out of thin air. Most people don’t understand the right way to do it, and when done wrong, it will be uncomfortable – or worse!

Anal sex and the taboo around it

Women who have tried it most likely did so when they were younger. They had a young boyfriend who had no idea what he was doing, and he just tried shoving it in like he would with vaginal sex. At best, he squirted a bit of lube. The woman would then swear she’d never try it again, and she’d tell her girlfriends how horrible it was.

Anal sex has always been a huge taboo, and often considered sinful. People assume any woman who would want it is some sort of freak, and others believe that any man wanting to engage in the act, even with a woman, must have some deep-seated homosexual tendencies. This is all quite stupid really. Don’t let ignorant people stop you from enjoying anything. Just the taboo breaking itself can be a huge turn on for anyone. [Read: 14 ways to get your partner to open up and communicate about sex]

Pleasure points

The clitoris is an amazing thing. How amazing? Anal sex can actually stimulate it and bring many women to intense orgasms. You know those iceberg diagrams, where what you see above the water is only 10% of it? That’s kind of like the clitoris. What you see above the skin is a fraction of what’s there.

The G-spot in the roof of the vagina stimulates the clitoris from below. And from where we all know it to be, the clitoris splits like a wishbone and runs down along both sides of a woman’s vaginal lips. It makes it as far as the perineum, next to the anus. When done right, anal sex can stimulate the tips of these extensions by expanding the sphincter. And the penetration, even though not vaginal, can stimulate the G-spot. [Read: 13 untold sex secrets you definitely need to know!]

Before you begin

Anal sex is not something for a random hookup. Couples should spend at least a month making love in more traditional ways before they even think about trying it. And then, especially if it will be the woman’s first time, they should approach it slowly. A couple that doesn’t trust one another should get over that before attempting anal sex.

Before going for the whole shebang, start in the shallow end with a bit of butt play. Once a woman is already wet, either after oral or vaginal sex, the man should put a lot of lube on one finger. Press the finger against her anus and rub very gently. After a few minutes of this, slowly push the finger in.

The woman should relax her sphincter muscle and remember to breathe. Take it extremely slowly, and do this a few times before you try the real thing. And gentlemen, it’s only fair, if she wants to try doing the same to you, let her. There’s a good chance you’ll like it, and that doesn’t make you gay! [Read: 20 hot sex ideas to blow your lover’s mind in bed!]

Nice rims

A rim job, or rimming, is where one person uses their tongue and mouth to massage another person’s anus. A lot of people actually enjoy giving rim jobs, and it’s incredible for the one receiving. After a shower where you wash yourselves thoroughly, try rimming her. You’ll need to work together to get over any discomfort you have with things like this. It will be worth the effort.

Rimming, or any gentle massaging of the anus with lubrication will help to relax the sphincter muscles. This will feel amazing for her, and is a great way to prepare for anal sex. Try it while stimulating her clitoris, or fingering her to drive her wild. To be safe and prevent any infections in her vagina, don’t give her oral sex after rimming, or finger her after touching her anus.

Final preparations

Once you’ve experimented with some butt play and become more comfortable with the idea, you’re ready to take the final step. A note on protection first: Unless you are in an exclusive relationship and are both disease-free, condoms should always be worn. The risk of HIV transmission skyrockets with unprotected anal sex. Other diseases can be transmitted this way as well.

Begin your first anal sex session with a hot shower or bath to relax. A glass of wine or two will also help loosen you both up in both a mental and physical sense. Begin with foreplay as you would any other sexual encounter. Stimulate her vagina, and if you can, bring her to orgasm once through oral or vaginal sex.

Start with rimming, or if you haven’t enjoyed that, some finger play. Gently massage her for at least five minutes before even putting any pressure inward. Add more lube to her anus, and a lot more all around one finger, and then gently slide it in. Slowly finger her for a few minutes to ensure she’s well lubricated.

The grand entrance

It’s time for the man to lubricate his penis, or the condom covering it. Only water-based lubricants should ever be used with condoms for any type of sex. Don’t be afraid to use a lot, and put another dollop on her anus. You can use whatever position you’re comfortable with. Woman on top, missionary, and doggy-style *regular or sideways* will all work.

Very gently push the tip of the penis against the anus. The woman must relax her sphincter muscles and continue to breathe. It should slide in fairly easily, but go extremely slowly. Go in about two inches and then stop and wait. Don’t do anything for two minutes. Let her get used to the feeling. Communicate, touch each other, and kiss if you’re in a position that allows it. It may help for the man to stay completely still and have the woman do the moving at first. [Read: 22 reasons why women fake an orgasm so often]

Now slowly pull out just a fraction of an inch, and push back in. Repeat this, but with each successive pump, pull out a little more, and push in a little deeper. Do this slowly for a few more minutes, and before you know it you’ll be having amazing, hot, dirty, kinky, mind-blowing anal sex.

Once you’ve got it going, kiss, suck on a breast, and rub her clitoris with your finger, or better yet with a vibrator. Don’t start pumping away furiously like they do in bad porn, keep a moderate pace. Finally, don’t forget to enjoy yourselves.

See? That wasn’t so bad!

Not every woman will like it, just like not every woman enjoys any given sex act. If you do it right though, it will not hurt. Don’t confuse discomfort for pain, the first time will probably feel pretty strange, but as long as you follow these instructions, it should not hurt. Obviously, if anyone does feel any pain, you should stop immediately.

Do it right, and the chances are that you’ll both enjoy it. Try a few more times later, you’ll find that as you both become more comfortable and confident with it, it will only get better and better. If you don’t like it, hey, at least you tried. We could all use a little more kink in our lives.

[Read: The top 50 kinky ideas you need to try at least once for a really sex relationship]

Forget what people say about it, anal sex is hot. Follow this guide to find out why breaking the taboo could crank your sex life up to 11!

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Eli Walton
Eli Walton
I'm a freelance writer dividing my time between the beaches of Thailand and my hometown of Chicago....

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5 thoughts on “The Curious Guy’s and Gal’s Guide to First Time Anal Sex”

  1. Hardheykhay says:

    Very 9s article…. Dont be confused, Anal sex is really hot…. ENJOY!

  2. Rebecca says:

    I really want to try anal with my partner I have tried it once before but it hurt. Also I’m shy about asking him or suggesting can any one help me PLEADE

  3. Lubel says:

    Oh, it was painful…. at first! It was with one of my boyfriends who I was visiting at college. He had talked about it a lot, but I never felt like doing it at all, but the more we would have sex the more he would ask and the times we would 69 he would lick my ass which at first I thought was really weird, but got used to it. That turned into just a sliding a finger in and sometimes a thumb when he was behind me. This went on for a few months and until I visted him for his birthday. I drove to his college and we hung out, but always rented a hotel so we didn’t have to deal with his room mates. Of ALL the times I got my monthly friend that weekend so feeling bad after we did a little foreplay I finally said okay and told him he put it in my ass. We didn’t have lube so he just use his spit. Luckly he we went really slow and was great about as far as asking if I was okay and if he was hurting me.. A few times it really hurt, but once he finally slide in he just left it in and didn’t move. It took about 10 mins or so of just breathing and not thinking about it until it finally didn’t hurt. After that we used lube each time and that made a magical difference! Try it, guys!

  4. Tbh derder says:

    Are you honestly asexual? Vaginal sex is (or at peast should be) pleasurable to everyboy involved and if anal is just not you cup of tea, that’s fine but some people don’t mind anal or actualy enjoy it.

  5. Tbh derder says:

    Also, I belive sex isn’t a favor or a thing of negotiation, it’s something done if you love a person and want to express it whilst conviniently pleasuring everybody.

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