I figured you all would like this kind of post, since most of the search terms that bring people to my site have to do with butt sex (and my most-viewed post is about my first time doing it). This guide is mainly written for the receptive partner (the one whose butt will be fucked), but insertive partners (the one fucking the butt) should read it too.
If you’re curious about my first anal sex experience, you can read about it here.
1. Think about whether you actually want to do it.
Do you actually want to have anal sex? If the answer is no, I suggest reading the rest of this guide first, as it may ease any fears you may have. If you still don’t want to do it, then don’t! Don’t let someone pressure you into doing it if you don’t want to; the point of sex is for everyone involved to have a good time, not just one person. Also, apprehension will cause you to be tense during sex, which will likely cause it to hurt.
If you’re curious about the idea but still not sure, you can try some other anal play, which may help you decide whether or not to have full-on anal sex. Read on for more tips on that.
PS: It doesn’t matter what kind of genitals you have, anal sex can feel really good for all different bodies! It’s not pleasurable for all people, but for many, stimulating the anal nerves feels great. Anal sex can also indirectly stimulate the G-spot, and also can stimulate the prostate.
2. Make sure you’re with a partner you trust.
Just as with vaginal sex, anal sex can cause pain and discomfort. You want to make sure your partner will respond appropriately to any concerns you raise before and during the act. Your partner should slow down, pull out a bit, or stop completely if you are in pain.
3. Talk about safe sex with your partner.
Anal sex is the riskiest sexual activity, due to risk of anal tears. These tears not only hurt like a mofo, but also provide an easy path for bacteria and other evil STI-causing organisms/viruses to get into your bloodstream. So make sure you and your partner get tested for STIs, and even if you’re totally STI-free, use a condom anyway, because it’ll help keep things cleaner, and if a penis is involved, it’ll prevent bacteria from going into the insertive partner’s urethra. You may also want to talk about safe-sex tools for manual and oral stimulation of the anus (gloves and dental dams).
4. Wash up.
Sticking stuff up your butt isn’t like sticking stuff into a pile of shit. Your poop is usually stored in the colon, until it’s time for a bowel movement. The penis or dildo will not be going into the colon; it will go into the rectum, which may have some poop in it if you need to use the bathroom. To prevent messes, go to the bathroom and clean around the anus before playtime. (I usually do this right before foreplay.) Enemas generally aren’t necessary, but if it’d make you more comfortable, you can read about them here.
5. Warm up, and USE PLENTY OF LUBE!
Even if you’ve had anal sex many times before, do not go straight into putting the penis/dildo in your ass! It will likely hurt and you may injury yourself. You need to get aroused (to relax your sphincter muscles in your butt) and prepare your ass to have a large object thrusting inside of it.
First, do what turns you on. Touch each other’s genitals, watch porn, dirty talk, lick each other, whatever makes you aroused. Then, start anal play slowly. If you’re into rimming (orally stimulating the sensitive nerves around the anus), you can do that. Many people start out by inserting a finger into the anus, kind of like fingering a vagina (but more slowly!). MAKE SURE TO USE LOTS OF LUBE! The anus and rectum do not self-lubricate, and are sensitive, so if you do not use enough lube, it is more likely to hurt, and you may tear the anal lining. This will hurt even more, and you might even need to get surgery to fix it. Don’t be afraid to ask for more lube at any time during foreplay or sex. Use a water-based or silicone-based lube; many people (like me) prefer silicone, since it lasts longer and is more slippery, but some people are fine with water-based lube.
After inserting one finger and getting comfortable with that, you can insert more. By the way, you can stick your fingers in your own butt, or your partner can stick their fingers into your butt. It doesn’t matter – it’s just a matter of personal preference.
Sex toys are a great way to warm up. Butt plugs, anal beads, and dildos can all help prepare your butt for anal sex. Just make sure any toys you use have a flared base or another design that keeps them from being sucked into your ass. You can read about that here. Don’t forget lube with these as well! But if you’re using a silicone toy, don’t use silicone lube (it may degrade your toys), unless you’ve spot-tested the lube on the toy already and had no problems.
6. Relax, LUBE UP, and stick in the penis/dildo.
Relaxing is super important to prevent pain, discomfort, and injury. So make sure you are relaxed before the penis or dildo goes in.
When it comes to positions, I usually go with doggie style, but lay my head, forearms, and/or upper chest on the bed (or ground, depending on where we’re fucking), and spread my legs a bit. This way, my anus is naturally opened up a bit, which makes things easier, and makes me more relaxed. It’s also good because I’m kind of lazy and don’t like propping myself up. To read up on more anal sex positions, check this out.
Before you stick in the penis or dildo, put on a condom and PUT LOTS OF LUBE ON IT! Then, slowly insert the tip of the penis or dildo. Do this very slowly, take pauses, and make sure the receptive partner is breathing and relaxing. It may hurt at first. If so, pull out and add more lube. Then you can try again. If it keeps hurting, stop and try again some other time.
After a bit more than the tip is in (maybe about 3 inches), try (slowly) thrusting. The insertive partner can control this, or the receptive partner can, depending on positioning and what you’re comfortable with. As you proceed and everything feels fine and dandy, you can increase the speed and depth of penetration. If it hurts, slow down, pull back a bit, and/or add more lube. Soon you will be fucking away!
Make sure to communicate with your partner about how you are feeling during sex! If it hurts, let them know so they can adjust. If it feels awesome, let them know too!
7. Clean up, and talk with your partner.
Following the afterglow of sex (and in my friend’s* case, listening to “I Just Had Sex” by the Lonely Island after every sexual encounter), it’s time to clean up! Remove the condom, clean off your genitals and ass, and wash your hands and any toys you used. It’s also a good idea to talk with your partner about how you felt during sex, what worked, and what didn’t, so next time will be even better!
Other important stuff:
-Do not stick the penis/dildo into a vagina after it’s been in an ass without cleaning the penis/dildo or changing condoms first! This will introduce bacteria that should not be in a vagina, and may cause infection. (It’s fine to go from vagina to ass, just not ass to vagina.)
-Do not use any sort of desensitizing wipe or cream! Pain is your body’s way of telling you something is wrong. If you take this away, injury is very likely.
-It’s not gay for a dude to stick something in his ass! Many straight dudes think that if a woman licks his anus or sticks her fingers/a toy in his ass, that makes him gay. That’s totally not true. Sexual orientation isn’t about the acts themselves, but about the person you’re doing them with. (For example, if a lesbian enjoys being penetrated with a strap on by her female partner, does that make her straight?) If you were born with a penis, then you have a prostate, and sticking stuff in your ass can stimulate the prostate (which feels really good!).
Thanks for reading, and have fun fucking! Do you like butt sex? What was your first time like? Did I forget any important tips? Any questions? Let me know in the comments below!
*By my friend, I mean me. But I stole the idea from my friend.
my camera charger to take pictures of it! So I’m doing a porn review instead.) 
Red Hot Rosaline 