Honestly, if Anal Sex Hurts, You’re Doing it Wrong.
There are enough people in the world that I don’t like and consider to be a pain in the ass that I see no point in letting people I actually like cause me genuine pain in my non-rhetorical ass. That’s not to say it hasn’t happened, but I didn’t like it. Every acquired skill has a learning curve, though, and some people are more intuitive than others, so a certain amount of discomfort is to be expected when exploring the fun to be had sticking things up your butt or the butt of another person.
Much has been said on the subject of anal sex and I am about to say some more. If I had to give an elevator speech about how to have the most enjoyable anal sodomy experience, I would likely boil everything down to taking your time and using a lot of lube. As we in the sex-positive community like to say, “lube, lube, and more lube.” Also, if you’re sticking something other than a penis or dildo on a harness into that tight pleasure hole, please make sure the base is wider than what it’s trying to fit into. There’s nothing like fishing something out that’s slipped into your butt during an intimate moment. Or making a trip to the ER so someone in a lab coat who is not into medical play can fish it out.
I’m not going to explain or suggest ways to talk someone into having anal sex. We can tackle difficult requests and conversations in a future update. For now, let’s just focus on ways that people who know they want to engage in butt play of some sort, including penetration, can do so safely and with minimal discomfort and no actual damage.
This leads me to a mini-rant: If you have an asshole, odds are in your favor that you can enjoy anal sex up to and including penetration. It doesn’t make anyone anymore “gay” to enjoy having the many nerves around their rectum, anus, and perineum stimulated than it makes anyone “gay” to like sucking on a Popsicle. For most of us, guys perhaps especially, the shame association that has been cultivated between anal stimulation, sexual sin, and shit has discouraged many properly planned and prepared explorations and encouraged unsafe, spontaneous, sometimes questionably consensual encounters. The best way to enjoy playing with an ass is to get to know an ass, yours included.
Things to Remember:
It’s Not a Contest: If there’s a goal to anal play it’s pleasure, however those involved define it. The goal is not necessarily to take the biggest cock, the longest dildo, or the most aggressive thrusts, although those whose only exposure to this kind of sexual activity has been through porn may think otherwise. Porn is entertainment, although sometimes it’s smart entertainment. When it comes to butt stuff, I’d say most porn should come with a warning label that reads “Trained Professionals on a Controlled Course. Do Not Try This at Home.”
Start Small, Go Slow: For whatever reason, there’s this popular idea that the first time you play with an asshole should be the first time said asshole gets filled to the rim with dick or toy. Exorcize that thought from your mind! If the ass opens up, great. If it just wants to be played with, also great. Again, the goal should be pleasure. Pleasure comes in many forms.
If it’s inexperienced, get to know the asshole in your bed gradually. Kiss it, lick it, stroke it, place a vibrator against it, and if it’s feeling like guests, slip a finger in there. This allows your bottom to adjust to having that area of their body touched and gives them an idea of what they like and what they’d prefer to put off or never have to think about ever again. If a finger sparks joy, consider two fingers or a slim butt plug.
If it doesn’t spark joy, explore your creativity. The body is a jolly sexual theme park and the asshole is one of its E-ticket rides. You may need to work up to penetration of any kind, may find that some things feel better than others, and may discover that what works one time is a flop the next time. It’s all good. That’s why we call it “play.”
Lube is Your Friend: Back in the 1970s, the idea of using intimate-purpose lubricants was unthinkable. Mostly that was stupid straight people thinking because women felt compelled to “prove” they were turned on by being dripping wet regardless of the reality of their lives, bodies, or the quality of the sex they hoped to someday enjoy. Gay men who engaged in anal sex, which is not all gay men, were way ahead of the straights, as usual, and knew the amazing value lube has in getting big objects into tight spots.
Unlike the vagina or the mouth, the anus is not self-lubricating. It’s also a delicate flower of romance that can easily be injured if you aren’t kind to it. Not only does this mean pain but it can mean infection, neither of which is good or fun. Use a water-based or other condom-safe lube if you’re using protection, which you probably should be doing.
Contraception Matters: It’s lots of fun to joke about “technical virginity” and how ass sex with a fertile woman is a good form of birth control. Hardee har har. And while it’s true that babies are not conceived in the anus, that doesn’t mean one can’t pregnant after only being fucked in the ass. Cum runs. So, if pregnancy is a concern, use a condom. Frankly, as good as skin-on-skin contact feels, a condom will help cut down on potential mess, protect against most diseases, and help make intercourse smoother.
Dirty, Dirty, Dirty as You Wanna Be: Potty training is not one of most parents’ favorite parts of childrearing. There’s a lot of guilt, shame, and hurry associated with peeing and pooping, and not only do parents pass along their own issues, but they often generate new ones because they haven’t dealt with the ones their parents gave them. It’s ok to be a little freaked out about things going into and coming out of your or another person’s butt. And it’s ok to do things to minimize the chance of any muss interfering with your fun.
Probably the best and easiest thing that you can do is evacuate your bowels. Unless you’re planning to go deep, most play won’t encounter much, if any, waste so long as the area is kept clean. For those able, a home bidet can be a pleasurable way to enhance hygiene and make oneself available on shorter notice. Hot beverages like coffee can encourage the intestines to get moving if they’re a little sluggish and you’re worried they’ll embarrass you in the middle of a good time.
Enemas can be part of creative shared butt play or an entirely solo enterprise of purely utilitarian purpose. Be patient with them because they can take longer to work than it seems. I once had some great butt sex after an enema. Upon returning to the bathroom for post-coitus cleanup, I learned that the saltwater solution was still inside of me. There was no negative fallout, so to speak, but had there been, I was with the right person that night. This brings us to…
Talk About It: As always, the best thing to do before trying anything new with a partner is talk about it. You don’t have to swap therapists’ business cards to prove you’ve handled your childhood stuff, but it’s important to make sure both the person whose ass will be touched and the person who will be touching it are on the same page about what “touched” means. Likewise, what degree of mess is cool.
Some people freak out if they see a little color and others delight in administering enemas. Considering what a vulnerable thing it is to bottom for anal fondling, it’s good for everyone to ponder both worst- and best-case scenarios and have some idea how they’ll react. Talk about lube allergies and preferences, experience, apprehensions, hopes, and desires. Then move forward at the pace that feels best for each situation. And remember, sometimes no matter how experienced the ass is, it acts like it’s a damned virgin so lube, lube, and more lube!