You ever see a dude try to mash buttons on a controller to create a combo in a fighting game? Yeah, well some of them apply that same technique to anal. Guess what? If you fuck like that, you aren’t gonna hadouken. Your partner will just shoryuken you into a fucking wall.
Welcome to the second part of Anal Sex 101, otherwise known as “STOP TRYING TO DRY FUCK ME CHAD”.
Chad: What? But like, you just stick it in, right?
No. No you do not. That’s the opposite of what you do. We went over this both times we tried to fuck and the last time you tried to use spit. SPIT.
Chad: Well, you said to use lube, so…
LUBE IS NOT SPIT. Okay. Sit the fuck down. I’m gonna teach you a thing if it fucking kills me.
Hi, hello, and welcome to my class. Chad, put your fucking hand down, I swear to god I will end you. Thank you.
This class is going to be the second half to the article I last posted, this time on the sex act that I am most intimately familiar with–anal sex! Now, these tips are not just for transwomen, but for anyone that wants to explore having sex in this way, though I will admit my experience with anal mainly comes from cis men.
Chad: Ch’yeah it does. Up top!
…I am going to take a deep breath, and when I open my eyes, he’ll be gone, right?
Chad: Still here teach! See what I did there–Teach is kinda kinky, isn’t it?
Please. Just stop. God.
Moving on, anal sex is one of the most intimate acts you can do with a partner of any gender. This is partially owed to it not being standard sex for many people–though it is generally the norm for me and any other transwoman interested in bottoming or topping, for many people it’s almost subversive, though I think attitudes towards it are less damning now than in the past.
While it may seem simple enough to just, you know, use the back hole instead of another one, anal sex is a bit more complicated than vaginal or oral sex. It requires far more prep to do the act, though doing it well takes about the same amount of effort in some ways.
However, there is one thing that is key to anal–one thing that you can absolutely not do it without. And what is that, you ask? It’s not a giant dick or you know, just having an ass. What is the one ingredient that, once your partner agrees to anal, will be the difference between ecstasy and ten minutes of trying to shove your master sword into a too-tight sheath?
Say it with me. L-U-B-R-I-C-A-T-I-O-N. LUBE. LUBRICANT.
There’s no anal sex without lubrication. I don’t care how long you’ve been doing it for, you absolutely have to have lube. This is true for everyone, not just transwomen. Without lubrication, anal sex feels kinda like you’ve cut open a wound in someone’s back and are trying to fuck it with a cucumber–it isn’t fun, there will be bleeding, and there’s risk of tearing. Nothing good.
There is also the matter of making sure you use -enough- lube, and the right kind. Let’s take a brief overview of the types. Generally, there are two types of lubrication.
There are also oil-based lubricants, but those will degrade and break down condoms if you use them, and since most people are likely to use condoms when doing anal, especially early on in a relationship, we’re not going to discuss them. Also, I’ve never use oil-based lubricant. Why? Again, they degrade condoms.
Silicone based lubes are silicone, meaning they won’t be absorbed by the body nearly as quickly as water-based lubes. Water-based lubes, on the other hand, are absorbed more quickly. Though both can be used for all types of sex, some people avoid silicone based lubes for vaginal sex because of the absorption factor–many consider water based lubes to be safer.
HOWEVER–the booty is not a vagina, and many vaginas produce their own lubricant (not all—this can lessen as women age, and that is absolutely fine damn it so fuck off) to make sex easier. The booty does not. And since it can be prone to tearing, and anal sex requires time and work up, it is generally best to stick to silicone for anal sex. Water-based lube will be absorbed too quickly, and, again, will lead to tearing.
No one wants tearing. I’m a huge masochist and I absolutely do not want it. That’s too much information but whatever, it’s staying in here.
Chad: What’s a masochist?
Anyone that would willingly date you, Chad.
Chad: So it means awesome. Sch’yeah, right on!
Are you just fucking stuck in the 90s, or…you know what, I don’t want the answer to that.
Most lubricants will tell you whether they are silicone or water based on the front of the packaging. Be careful, as even anal-specific lubes can be either or, and you don’t want to make a mistake here. Trust me.
So now that you have lube, what’s the next step in this wonderful, magical journey to explore the backside? Prep work.
Anal is not an instantaneous thing for a lot of people. Even with lube it can start out being kind of painful, especially if you fucking try to shove something in there without trying to loosen up the muscles there first. We’re easing into this people, not fucking doing demolition. You’re gonna need to assess the walls before you can tear them down, if you catch my drift.
How you do this is largely up to you. Generally, people will use fingers to relax into anal penetration–this can be done by the person on the bottom (i.e., the receiving partner) or by the one on the top. Many people consider this to be an extremely intimate act–and they fucking should, you have your fingers knuckle deep in someone, treat them with some goddamn respect. If you are uncomfortable with the idea of having your fingers in someone, perhaps you should consider that you shouldn’t be shoving your dick in their ass. Looking at you, Chad.
In practice, this is like any other kind of foreplay. Your goal is to massage the ring of muscle to help with ease. Over time, this will get easier–just make sure to use plenty of lube and go slowly, especially your first time. This needn’t be done with a partner either; you can easily practice this yourself in your own experimentation.
If you have real difficulty doing this with fingers alone, and you are committed to having this kind of sex, you can also get anal training kits both online and in sex shops. These are typically a set of three butt plugs in increasing size that will allow you to ease into the feel and stretch of having anal sex. Obviously, though, you’ll still want to start small.
Now, for the main event. Light some candles. Throw some rose petals on your bed. Put on some lingerie.
Chad: Get on the train to Bonetown, USA!
…or if you’re me, call up some fuckboy from Tinder and throw your legs in the air. God, I hate you, Chad.
After you’ve done the prep, ease into penetration. If you are the penetrating partner, whether you are using your own genitalia, a dildo, or a strap on, be gentle and patient. Your partner will probably need some time to adjust. If you go straight to bang town they’re likely going to be in a lot of pain and will kick you out of bed with all the strength they can summon. No, I am not speaking from experience. No, really, I’m not. I’m–just shut up, alright?
And listen. I do not care how proud you are of your gigantic dick; if you’re well-endowed, this will be HARD for your partner. The larger you are, the more time it will take to adjust, and the more patient you may have to be. They may also not be able to get it in the first time–if they can’t, you need to treat it as being okay, and if they want to do so, continue to do some prep work, or ease them into it slowly over a period of time. Rome wasn’t built in a day, no matter how much buttfucking they did.
Overall, at this stage it is important to remember what I said in the last post–listen to your partner. If there is something you or they don’t like, if they’re uncomfortable, put on the red light and fucking STOP. You will both be better for it in the long run, no matter how much they complain about their blue balls.
Chad: Well, it’s really uncomfortable to have–
Chad, look at me. Look deep into these baby brown eyes. What do you see there?
Chad: I see…darkness. The eternal void. The end. The silence of eternity, oh god.
Yes, excellent. That is what awaits you if you finish this sentence. People. Listen. To. Your. Fucking. Partners. Do not try to coerce them into acts that they can’t or won’t do. Doing that is manipulative, creepy, and cruel.
Chad: So if I stop bugging you you’ll eventually let me tap that ass again?
…jesus fucking christ if the cops wouldn’t put me in a male prison or shoot me on sight.
Sigh. Don’t be a Chad, people. Ease your way into anal sex, use plenty of lube, and above all else–listen to the people you’re mashing uglies with. If you do, you’ll be sure to succeed. Have fun doing butt stuff!
Special thanks to our newest Patreon Supporter–Amy R.! Also, a resounding thank you to Dillon P., who edited this and other articles! We love her.
A brief news note: The update schedule will be changing to once weekly for a number of reasons, ranging from my own sanity, to editing a novel manuscript. Updates will be on Wednesdays!