An Extensive Guide to Butt Stuff: It's Time to Get Comfortable with Being Uncomfortable

If you know how to enter correctly, the backdoor leads to world of new pleasures.
ILLUSTRATOR Jasrelle Serrano

It’s time to get comfortable with being uncomfortable! Because that’s what anal sex is in the beginning: It’s uncomfortable in all aspects. It’s uncomfortable to talk about with your partner, it’s uncomfortable to perform. But being uncomfortable should in no way deter you from expressing your sexuality and your sexual fantasies, if this is what you really want.  

In the past decade or so we’ve really opened up about anal sex. It’s no longer just for gay guys, yo. Hell, it’s no longer for straight men to perform on women either. You know what I’m talking about… pegging is hot with the right partner. What’s pegging you ask? Read on, gentle reader. 

But first off, anal sex should not hurt. It’s a new ooh ahh ahh sensation that may be slightly uncomfortable at first, but pain should not be a factor in anal sex if done correctly. And you know you’re doing it correctly if you’re going slowly and communicating properly.

Get relaxed. Take your time. Have a couple of orgasms first (both of you, don’t be greedy now). It’s best to build up to anal, especially on your first go. Don’t head straight to the back door. Be a gentleman!  

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How about some rimming for starters? What’s rimming? Rimming is when you kiss, lick or penetrate your partner’s anus with your tongue. It’s a gentle start to the proceedings, especially if you combine regular oral sex with some action further down south. Or how about massaging your partner’s anal opening with your finger? The inner and outer part of the anus has thousands of nerve endings that are incredibly sensitive and can be used to your advantage and her enjoyment. Just don’t forget to lube your finger up.  

Now speaking of lube, here are some very handy tips for those who would like to try anal for the first time (but don’t really know how to go about it). It doesn’t really matter if you’re boy or girl, gay or straight, these tips will give you what you need to know before doing the deed in a safe, sane, and fun environment.  

1| Make a Mess 

Scared to make a mess? Don’t be! Usually the mess from anal comes from lube and not from your butt. That being said, dark sheets or a dark towel can also ease your worries. There is always a tiny amount of fecal matter inside your anus whether or not you need to use the bathroom, so please do not think that enemas are your friend here.  

Eating right, using good quality lube, and having baby wipes close at hand are always good ideas. If you’re still worried... dude, you do realize you’re entering a butthole, right? The place where poop comes out? Everyone poops. There’s a children’s book that explains all that. If you can’t be cool with that, then maybe anal just isn’t for you.   

2| Use lots of lube 

Lube. Lube. Lube. And then lube up some more. When exploring anal sex, lubrication is incredibly important. The anus, unlike the vagina, is not a self-lubricating area. So if you want a good (and safe) time, the more lubrication, the better. Lubrication helps decrease bad or painful rubbing or chafing and increases positive or pleasurable friction.  

While silicone-based lubes are best for anal, since they are slippier and last longer, they cause condoms to break and destroy latex toys in the long run. If in doubt, go for a water-based lubricant which would be safe for any latex-based condom and toy. There are also hybrid lubricants that are the best of both worlds: safe to use with condoms and toys, but gives you the long-lasting slickness of silicone.  

Also, do not scrimp and buy cheap lubricants, dude. Splurge on the good stuff. My personal brand of choice (that is available locally) is Sliquid, which has silicone, water, and hybrid variations. There is also a version called Sliquid Organics Natural Gel, which is a cushier version, perfect for anal play. Ilya carries a good selection of the brand, though they don’t carry the silicone or hybrid variations. 

3| Engage in safe sex only 

Now this is important: Whether you’re straight or gay, you should always play it safe with anal sex. Women are 17 times as likely to contract AIDS or HIV through anal sex than they are through vaginal sex. Just because you can’t get someone pregnant doing anal doesn’t mean you can’t get any number of sexually transmitted infections. 

The amount of trauma the anus and rectum receive during the deed makes the likelihood of you getting a sexually transmitted infection higher than during vaginal intercourse. The anus itself, since it does not self-lubricate and has fragile skin that can easily tear, allows sexually transmitted infections to pass easily into the bloodstream. Do yourself and your partner a favor and practice safe sex. Always.  

4| Mind your position 

Here’s a tip: Backing up instead of pushing forward is a great way for beginners to start. That way she who is on the receiving end can control the insertion and her own comfort level. You can also try the lap dance position when doing this. It not only provides a sexy view, but helps give your partner total control of the situation.  

Oh, and don’t forget to breathe as penetration is occurring. As you breathe deeply, your inner sphincter muscle will relax and help facilitate penetration. It’s important to go slowly when you do have anal sex. Don’t go all porno and start pounding away. Communicate with your partner. If something hurts, stop and take a breather. Tensing up will only make things more difficult and a lot less fun. 

For guys, the male G-spot, or the prostate, naturally swells up when you’re aroused so when you’re up for some anal loving, try elevating your legs and have your partner gently massage the entrance to your anus before inserting fingers or a toy (well-lubricated of course) once your muscles are nice and relaxed. She will recognize that G-spot as a chestnut-sized bump about two inches inward. 

5| Employ toys 

Now there are two ways toys are your friends when it comes to anal play. The first way is getting your butt used to what insertion feels like. A small butt plug is a good beginner toy since it gets you used to insertion and having something inside your butt. Try having your usual vaginal intercourse with the butt plug in place. Being filled up in both places is definitely an experience, and can lead to very powerful orgasms.  

Now the other way to use a toy is if you’re interested in pegging. For the uninitiated, pegging is a sex move wherein the man is penetrated anally by a strap-on dildo worn by a woman. Shocked? Don’t be. It’s gotten pretty common, especially among the younger set.  

In the realm of sexploration, it was only a matter of time before straight men finally began to wonder what it was like to have anal sex themselves. If gay men were enjoying it and now straight women were starting to enjoy it too, then what were straight men missing? Pegging is the answer.

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6| Know the peg

Honestly, men, if you’re all so gung-ho to do it to your women, don’t be so scandalized if your woman wants to turn the tables around and do it to you. Equality, remember? It happens in the bedroom, too, darling. 

All the above tips work perfectly fine for pegging, you just need the right accoutrements, which in this case is a strap-on and a dildo. You can do the shopping online. Involve your partner in the process and get the excitement going well before the actual event takes place. The Internet is a veritable smorgasbord of toys for big boys and girls.  

Be as picky as you want. Some strap-ons already come with the dildo and some strap-ons come without. Dildos come in all shapes and sizes and colors. Don’t go off starting with the biggest and baddest toy in town now. Let’s leave something for later. Also for later can be a double-ended toy that can double your pleasure since it penetrates both you and her at the same time. Cool, huh? 

7| Establish a safe word

In the end (pun intended), what is important is that you and your partner keep things open, keep things cute, keep things sexy. Leave your judgement at the door and explore your sexuality together in a safe and caring environment. If at anytime you don’t feel safe, you should stop. Listen to your feelings, listen to your gut.  

This may be the time you and your partner come up with a safe word. Banana, perhaps? Or use the common three-step safeword of most BDSM practitioners: red, yellow, green.  

Red means to stop everything now, things are not okay. Yellow means to slow down or to keep it at this level, do not escalate while I process what is going on. Green means everything is fine.

Remember, in any kind of out-of-the-box (yet another pun intended) sexual exploration, if your partner dismisses your concerns or can’t respect them, you’re doing it with the wrong partner.

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Felicia Wang
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