What is the best ways to prepare for anal sex for the first time?

I lost a bet to my boyfriend and now I have to try anal sex. He doesn't want to hurt me so he said I could have a month to research ways to make sure it doesn't hurt.
1 2

Superb Opinion

  • I am a gay man and an exclusive bottom who just loves getting fucked in the ass. If done right, anal sex does not really hurt at all, but can be a great source of pleasure for the person receiving it.

    The key to success is physical and mental preparation. The physical part requires a clean hole and a lot of lubrication where water-based lubricants often work the best. As for cleanliness, I would recommend making sure you have a complete bowel movement and a good shower before getting fucked. As you can guess, food that helps digestion will also work here to your benefit, like fibers, etc.

    The mental part is about relaxing your body and your asshole. Once your hole relaxes, it can stretch beyond your wildest imagination to help take your man's cock into you...

    A butt-plug may also help. This has been one of my biggest helpers to stretch my hole in order to be able to accommodate guys with really thick cocks. To that end, I'd recommend starting with a small enough plug that you can wear at the beginning. But, it should still be thick enough so you can feel the walls of your asshole stretching a little. After wearing that for a few days, you can gradually move to the next larger size, and then increase the size of the plug to really thick ones that you could not have accommodated at the beginning. This way, I've been able to enjoy really humongous cocks in my ass. I sure hope you will, as well!..

    Finally, the position of anal sex is also important, especially for the person taking it. That could depend on gender, but also personal anatomy. My favorite position getting fucked is the missionary position. Lying on my back with my man on top of me while raising my legs over his shoulders proved to be the most natural position for me where I always draw a lot of pleasure.

    Please feel free to write back if you have any more questions. Good luck!..

Most Helpful Guy

  • I'm going to copy and paste something I wrote yesterday...

    There are many women who love anal sex and experience it without pain. It can feel great and give them very strong and unique orgasms.

    However, it takes time and effort to get ready to a point where you can enjoy it without pain. Unfortunately, most women who try anal for the first time do so before putting in that time and effort, so they end up having a painful experience and many of them get turned off to anal forever as a result.

    It is very important to "train" your ass before trying anal sex. Anyone who tells you otherwise is ignorant. Get a tapered butt plug, preferably one that vibrates (you'll thank me later). It should have a small tip that gradually tapers to a larger diameter in the middle. The widest section should be about the diameter of your man's penis. Get some good water based (NOT silicone or oil) lube and use the butt plug to gently relax and stretch your ass while you masturbate. Do it many times and have lots of orgasms because that associates the sensations with pleasure in your brain. Once you are comfortable taking the full butt plug (which can take weeks) get a dildo of a similar size and shape to your man and use that to masturbate after first relaxing your ass with the plug. Take your time and don't push yourself outside your comfort zone. Don't try the real thing with your man until you are comfortable with the dildo and are enjoying masturbating that way.

    I can't overemphasize how important it is to have orgasms during the training process. You'll understand later when you find you really enjoy anal sex with your man and you have the best orgasms of your life by rubbing your clit during anal.

Most Helpful Girl

  • You can't really prepare to be honest. It's all about getting the sphincter to relax on the day and that's being in the right frame of mind and gentle stimulation of it as your getting lubed up. However practising opening your sphincter by pushing it out will help a lot.

Scroll Down to Read Other Opinions

What's Your Opinion? Sign Up Now!

What Girls & Guys Said

1 18
  • If only I had written a post long ago and bookmarked it. Oh, wait...

    What's the best way to do anal sex for the first time?

    • Wow, thanks that seems like good advice! I also read about these butt plug sets that can be bought to slowly stretch out the hole. Do you have experience with those?

    • As a matter of fact, I've bought such sets for several women over the years. They're fairly inexpensive, so if that's something you think will help or make you more comfortable, then I definitely recommend it. Get some water-based lube and use a decent amount - some people say "you can't use too much" but, actually, you can. Just use enough to make it slippery and you'll be fine. Note: if you're using a stainless or glass plug, you can use silicone-based lube, which will last far longer (it doesn't evaporate like water-based lube), but you'll need to wash with soap (or take a shower) for cleanup. You don't want to use such lube with latex toys, though.

    • this with 1 addition. extra lube. never too much lube.

    • Show All
  • The best way is to not do it at all. Medical science warns against it. Why allow penetration in an area not made for such when you have a vagina made for it?

  • Lube and the slowest of motion

  • Putting somethign small in there like a finger and then working your way up is the best way. Use lube or else it will hurt like hell. Believe me, I tried to fuck a lot of bitches in the ass with no lube it doesn't work.

  • start using a lubed dildo to start gauging the brown eye. Use the bathroom before starting anything. Make sure your rectum is empty. poop means it's not! You may find a simple enema to be pretty effective and sanitary. After you get used to anal, you could always do this real quick in the BR without mentioning this before making the way to the bed. Angle is important with a penis, as these things are pathfinders. when it's time, do lube, but also some finger play down there. it will help relax the sphincter which might otherwise clench on the dick like a cramp that just gets worse and hurts really really really bad. Can just go into it. play, don't be afraid to take little breaks. if one night you can't truly get it ok, then try some other night. don't be like 'it has to be today!!'... when you do get into it, you will love it. it stimulates a lot and women go nuts getting ass fucked. Good times.

  • Lots of foreplay. You have to be more than ready for vaginal sex in terms of wetness, arousal, vaginal stretch. Then lots of anal play, finger massages, small penetrations like starting with a finger and moving up. you have to get your back hole ready for big penetration. While he is fingering and playing with your hole, you will learn to calm your muscles around there, learn to take things in from there. you have to be extremely calm. Keep the communication up

  • That is disgusting! I would not do anal sex if I were you. Bet or no bet. Anus was not meant to be penetrated. It's for excess waste to EXIT from your body. It was never meant to be used for sexual pleasure. Porn has really twisted the norm of having proper sex. Doctors also warned about anal cancer because people are having anal sex. Anal sex is abnormal, and it's just disgusting. Please feel free to share your opinion on this topic. Lmk if you agree or disagree.

  • She should do it slow and finger you there first to relax you

  • You have to be willing, otherwise it will hurt. If you aren't willing any advice offered won't help.

  • Approach me. Will give you demo 😜

  • use lube, and relax. you might also want to try using a finger or something their first to help get used to it

  • U can have some hella Os

  • Use enema to get cleaned before sex.
    As you have a month you can use butt plugs or fingers you can use one finger first and slowly increase the no. Of fingers to get the hole stretched. You can also use a dildo to practice your self and learn the ways to make you feel good and get more pleasure.

  • Get a butt plug get the hole bigger so it dont hurt

  • Ok from my point of view so far i have had more Black women ask for that than white and they were pretty forceful about what they wanted and how

  • lots of lube and start small

  • use lube and just go really slow

  • I hope u want and not just lost a bet bc that is retarded