Catching Up On Some Dear K. Letters

***WARNING!!! This is officially my most graphic and potty-mouthed post to date. Be 18+ and proceed with caution! I’ve channeled my inner Dear Abbey, if you will.***

Oh, my dearest Pervy Readers,

I’ve decided to break another rule. This one involves Butt Sex. If you’ve read my books, you know there’s A LOT of it. Why? Because we love it. Yet for many of my readers this is unchartered territory. Which is asinine, If we’re honest. It is the year of our lord 2015 (or 2016, depending on when I retweeted this) and we’re all twisty, naughty people and should be past this by now.

butt sex

Still, I get so many messages about this very thing. They range from: “How much time a day do you spend contemplating gay sex?” (approximately 8 to 10 hours) to “Have you had a lot of gay sex” (Not the sort I write about as I’m anatomically challenged) to “Is anal sex as good for women as it is men?” (I’d assume the ratio of gay men that enjoy it is similar to women) and “I’ve never tried it but I want to. I’m just scared it will hurt and get gross” (If we’re honest, all sex is gross at times).

Before I get to the completely groundbreaking and marvelous point of this post, I wanted to address a few cliches about gay sex. Well, I’ll do my middle-aged, drunk, soccer mom best, at least.


  1. Not all gay couples have defined male/female sex roles. They’re a lot like straight people in that they enjoy variety. Some do lean heavily in one direction, but stop staring at gay couples trying to decide who’s the “man” and who’s the “woman”. That’s ignorant and narrow-minded. Especially if you’re hanging dry wall in your wife’s panties while you’re at work.
  2. Some gay couples don’t enjoy penetration. There are loads (punnnnssss!!!) of other ways to get off. Frotting, intercrural, hand jobs, blow-jobs, mutual masturbation, watching this gif…tomshower
  3. Gay men are not more promiscuous than their straight counterparts. I sweartagawd, if hook-up apps had been around in the 2,000’s, my thumb would have fallen off from all the swiping and the straight men that wanted to make me the Queen Of The Motel 6 would have had dozens of candidates to polish their swords nightly. And don’t pretend for a minute that there aren’t straight people on “dating” apps looking for their just-for-tonight soul mates. WE. ARE. ALL. WHORES. Some just got stuck with kids faster than others.duggar

Now, with all of that out of the way, I’d like to introduce the not so original but reoccurring theme of the letters I’ve been receiving from my incredible readers. Brace things and grip your buttocks tenaciously. This goes for my adorable boy readers as well.

Here it is:

Sarah aka K. Sterling’s Guide To Anal Sex For The Uninitiated

  1. Talk. Get over those squeamish 12 year old girl nerves and have an honest conversation about this. This is important for two reasons: 1.  You’re opening up and showing him/her what he or she’s up against. They’ve got some work to do if they want to make this happen. 2. If they don’t appreciate your honesty and aren’t willing to put you at ease, get the fuck out. They’re not worthy.
  2. Google your brains out. Read every first-hand account and step-by-step guide you can find. Then, go on a porn binge. DM me if you want links.
  3. Masturbate. Alone. Go with your normal routine and add the daintiest tickle. DO NOT grease up your fist and jam it up your no-no. That’s advanced technique and better left for experts and anniversaries. Just go for some mild tickling and see how that goes. Later, you can lubricate your narrowest digit and give it a prod. Just take your time.
  4. Once you’ve acclimated to two or three fingers swirling and probing you can invite your most trusted guest. IMPORTANT: make sure that whichever location you’ve chosen is your happy place. I like candles that smell like old school men’s shaving cream, low light, a relaxing massage and some Wu Tang. Booze, pot and/or Xanax are often participants as well. But, you do you, boo.
  5. If you’re like me, you’ve got some hang-ups when it comes to your body and you’re terrified that something could go amiss. Meaning: there could be poo. I read one of those “Dear Elderly Lady-Friend That’s Probably Never Had Sex” columns about the unluckiest girl that’s ever been born. Her boyfriend surprised her with the most romantic night ever and when they got to the hotel room, he leaned in close and whispered “I want to put it on your butt.” There would have been a Sarah shaped hole in the door ten seconds later, I would have run so fast. Unfortunately, our sad girl thought this was the path to a proposal so she slipped off her big girl panties and did a lot of grimacing and silent sobbing. Low and behold, there was poo and she was mortified. Not only did he not propose, he never called her back. This brings me to a VERY crucial point: As arousing as butt sex may be, that’s where most of us store our poop. No matter how you prepare, sometimes, shit happens. You need to make sure that all parties involved have at least a minimal grasp of bodily functions. Fun Fact: If you enjoy a healthy diet, you’re probably pretty clean to begin with. More on that later.
  6. Which brings me to my next point. A lot of readers have pointed out that I don’t address preparation beyond foreplay in my books. 1. It kind of kills the mood when my gays are about to throw down. 2. It’s not exactly kinky. Unless you’re into that and I’m sure there are plenty of books that discuss that in detail. I like a lot of fantasy sex in my books, so I leave the enemas out. But this is you and me and we should be at the point where we can discuss this. I won’t go into detail here. Just know that there are all sorts of ways you can prepare yourself. If you want the full deets, DM me and I’ll tell you whatever you want to know. I’ll say this though, cleanliness is next to deliriousness. If you aren’t worried about a mortifying accident, it’s a lot easier to get caught up in the moment.
  7. Now that you’re clean enough to pretend you’re a human mentos dispenser, it’s time to consider accoutrement. This is extremely vital: have a lot of lube on hand. Remember the candy man from Charlie And The Chocolate Factory? Your sex toy drawer or cabinet should resemble his shop. KY is not going to cut it, unless you’re not a fan of pleasure or utilizing seats. Lidocaine is my bff. It’s tricky to get in prescription strength but you can find loads (puuuuuunny!) of commercial lubes that contain it. Get some. Then, get some. Trick: Give it time to work. They sell plungers that are nothing like the creepy medical grade ones no one wants in their home that are lovely for inserting enough lube to get you started. Then, move on to whatever else you think might get you in the mood for ten or fifteen minutes. I don’t know, watch porn together or work on your blow-job technique.
  8. It’s been 10 or 15 and you’re feeling a helluva lot more into this but calm your tits, it’s still not time. We need to talk toys and more foreplay. Maybe you don’t have an arsenal of vibrating plugs. If you don’t, consider this: it’s $14 with Prime shipping and is great for beginners: Screen Shot 2015-11-17 at 8.45.30 PM Have your partner slather his or her hand in that miraculous numbing lube (I swear, you’ll still feel enough to sing your favorite aria) and gently ease a digit into your new favorite place. Now, play this by ear (or rear, as it were). As you become more comfortable, get more adventurous. Eventually, you should be ready for the above mentioned toy, if you’ve got one. If not, no sweat. If you are experimenting with toys, go slow until you’re ready for the real deal. Just don’t get over ambitious. Rome wasn’t built in a day, neither was your butt.
  9. Here’s where it gets tricky. This is the part you’ve been afraid of. It’s what the skanky girl that smoked in the bathroom during study hall warned you about.Why are we still listening to her? Even with lidocaine enhanced lube (and he better be doused with it), you might have to grin and bear it for a few seconds. You’ve got muscles that just don’t like letting things that large in or out. You know that time you ate half a block of white cheddar and two days later you cried when it came out? It’s a lot like that and lasts about as long. Do this: breathe through it and push back. I know, you don’t want to push because what if you accidentally push out a loaf. It’ll be ok. Breathe and push. Then, he’ll slip past that angry, clenchie ring. Now and then, your body will pull him in. Or, you’ll feel like you might split open. Relax, please. Your body just needs a minute to stretch. And you will. If he has manners of any sort, he’ll give you time to catch your breath and settle into it. If he’s marriage material, he’ll provide you with a soothing back rub while he waits.
  10. Then, it’s on. If you’re a dude and you are in possession of a prostate,   huzzah! If you are a woman and aren’t blessed with one, all is not lost. Many women are anal-erotic and experience orgasms that are as fulfilling or more so than traditional methods. If you aren’t anal-erotic but still enjoy anal sex, throwing in a few toys never hurt.

A final note about what to expect: 1. Unless you get ambitious and ask your partner to clap while he or she has both hands inside of you, your body should function relatively normally the next day. There may be a little lube leakage but that’s something you can giggle to yourself about while you’re in the checkout line. 2. Depending on your partner and how out of hand things got, you might be a little sore but it’s nothing to write home about. 3. Be mindful of your diet! I don’t care how serious you are about cleansing, being on a first name basis with the guy that asks if you want hot, mild or fire sauce with your Taco Bell order, you’re going to be a hot mess. If you’re serious about the butt stuff, kale is your friend.



So are lentils and fruits and veggies of all colors. And Fiber One bars. I’m partial to those.



You know, I can’t really think of anything else to add. Except find yourself an openminded and sensitive partner with a serious sense of humor.

I realize Wu Tang isn’t for everyone. So, I’ll throw this in for mood music.


Catching Up On Some Dear K. Letters

2 thoughts on “Catching Up On Some Dear K. Letters

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