8 min read

Should I cuck a cop?

Advice on doing anal, cucking cops, and getting over an ex.

From 19th century Italy, a part of the concealed erotic paintings of Sommonte. Cuckoldry is a centuries-old dilemma we eternally encounter. (Thanks PDR!)

Although the framing of the newsletter has always been framed as “part diary, part advice,” I never really leaned into the “advice” aspect. I named this newsletter “HOW TO FUCK LIKE A GIRL” ostensibly to talk about my journey from twinkdom to cubbery to girlhood all primarily through telling stories about my sex life. Despite that, I’m feeling surprisingly self-conscious about finally writing an advice column in earnest, maybe embarrassed to concretely say: “Here’s how you fuck like a girl.” For the most part I’ve domesticated my self-consciousness, put it in a cage in the corner and made it my bitch. But now it’s going beast mode on my psyche. It might be because my life is in total upheaval or it might be because I started a new cocktail of HRT that promises to give me any or none of the following symptoms:

  • Mood Swings
  • Bigger Boobs
  • Less Body Hair
  • Dehydration
  • Brain Fog
  • Nightly Visits from The Void

What you need to know before you read any of the following advice is that I’m in desperate need of some acupuncture, a sound bath, an exorcism, a month supply of adderall, a pat on the head, and bloody fucking steak.

It’s safe to say I’m still Figuring Things Out. Girlhood, adulthood, queerness, political praxis–girl I don’t know! I’m just trying my fucking best. But maybe that’s how it always is? Perhaps there’s no threshold that we magically cross where we feel qualified and ready for what life hands us.

So, let’s call this the “Advice Edition” of HTFLAG but really think of it like all of us sitting around a table, having a kiki, gabbing, and laughing. Maybe somewhere in all of this, we’ll find some truth, something useful. Or at the very least, hear some tea and gag. Maybe it’s like my own little Red Table Talk.

I’ve already collected a couple of questions for this edition, but if you have any sex, gender, or romance quandaries send them to dearverablossom@gmail.com or leave an anonymous message at 3words.ngl.link/cuteflesh.

More from Sommonte. Wonder if this is depicts an orgy or if it reads more like a comic?

My neighbor and I have started hooking up. I’ve been playing around with fucking men for the first time in my life, so this has been really fun. He told me he’d let me peg him. While I’ve Been A Top before, I’ve never done anal play. Any advice for a first timer?

-Everything Bigger, from Texas

Dear Everything Bigger,

First of all, hot. Please bask in the glory of your impromptu neighbor sexuation. Some of us pray our whole lives for a moment like this. Anal can be a bit intimidating, but with a little prep and a lot of communication you should be in for a fun time. Cum dumps on the internet might have you believe that one can be ready for butt stuff at any given moment of any given day - and while you definitely don’t need to douche every single time you bottom, the timing of meals and BMs are not things to be ignored. Some of us can’t center our entire lives around getting fucked in the butt, you demon twinks.

But, this isn’t about those demon twinks, this is about you, Everything Bigger. You’re a top entering a new domain, but a lot of the same stuff applies. Communicate. Try to anticipate what might make your partner feel good.

Bussies, like pussies, take a little petting and warming up before they’re ready for any serious business. They’re just like me in that way. I require a Hippie Speedball, a morning masturbation session, 30 minutes of staring into the middle distance, maybe a little crying, and probably some breakfast before I’m really ready to face the reality of my day. You have to be the Hippie Speedball for your neighbor’s bussy.

Always start slow - maybe rub your finger against his hole before sticking it in. Get yourself to two or three fingers before you whip the strap out. Go to town with your tongue - who doesn’t love a little rimjob? Maybe rub your dick up between his cheeks and lather it up with lube. Throughout all of this, check in. Personally, I think a little too much talking during sex can feel like a turn off, but done correctly, communication can double as dirty talk. “How does that feel, (you slut)?” “Do you like that (bitch)?” (Parentheticals are optional dialogue choices.)

So much of sex makes me feel like an alien in a human body trying new things out–what does this do? Does it feel good if I do it like this? Ooooh weirrrrd. Don’t be embarrassed if it takes a little maneuvering around for you two to find the right position to get your dick to fit in, that’s normal. Everyone’s angles are all different!

Once you’re in, go slowly. Like, a centimeter at a time. Check in with your bottom. If he’s a total butt slut, it might go in super easy and he’ll be begging you to rail him very quickly. If he’s not stretched and supple like an Olympic gymnast, he might do some breathing exercises while he adjusts to having you inside of him. If that’s the case, check in frequently and move really slowly. Once he’s gotten his Speedball and he’s nice and ready, then the two of you can get buck wild.

I have a friend-of-a-friend who is single and swiping. He recently matched with a woman who then made it clear that she wanted my friend of a friend to cuck her husband. The kicker is that the husband is a police officer who is heavily armed in his house. What’s the move here?

-Friend to the Bulls

Up front, let's say it seems rather dangerous. I personally wouldn't get into the potential for bitterness and a revenge fantasy that might spring from a dynamic like this, especially if the cuck's a cop. Especially if he's got more than one gun laying around.

It seems to me that, besides the problem of this cuck's artillery level, the questions here is: should your friend-of-a-friend get sexually involved with a cop? It’s easy to feel like the cuck, the dude in the corner watching, is not involved in the actual fucking part. But sex is about so much more than rubbing your crotches together–it includes who’s looking, whose feelings are involved, and who else is getting off. When you get involved in a non-monogamous situation with another couple, even if you’re only making real sexual contact with one half, you’re enmeshed with both.

Listen, I’ve accidentally had sex with lots of people who hold questionable political values. Politics just never really came up when I was hunting for dick on Craigslist, mostly everyone's advertising their varying levels of eagerness and nudity. The only reason I know any of these dudes' political opinions now is because a lot of men apparently have a penchant for a sudden post-coital political reveal. It's jarring. If you do that, stop it. I've accidentally fucked Libertarian crypto nerds and fuckboy pilots who don't see race and lots of other unhealed idiots (and, to be real, come back for seconds lol) but this feels like a different scenario. The potential to get sexually involved with a police officer is very much being advertised.

Sure, sometimes there’s a level of humiliation involved in cucking someone, which complicates the whole dynamic. Depending on the ways in which your friend is marginalized by this crumbling empire, I think it might even be healing for them to make a cop feel tiny. It may be thrilling to take the power back from someone who has the ability to decimate so many lives without consequence. In that way, I get it. Although, it might be a better idea for them to engage a normal Hot Wife/Cuckold couple and just roleplay out a cuck cop husband story.

In the context of cuckoldry, humiliation can be a way for someone to access erotic pleasure. Some people pay dommes a lot of money to feel the thrill of shame. But sometimes humiliation isn’t even a part of it at all. Sometimes a cuck likes seeing his wife pleasured because he feels like he’s not good enough for her, or that she deserves to have sexual experiences that don’t necessarily involve him.

So I think the answer here is the same answer to this question: is your friend okay with helping a cop find pleasure? Is your friend-of-a-friend cool with fucking a cop?


I’m having trouble letting go of my ex who ghosted me a year ago. She was my first serious relationship (though I wasn’t hers) and our breakup wasn’t particularly contentious (that I know of!) How do I stop dwelling on it and accepting the lack of closure?

-Feeling Forlorn & Forgotten

I wish I had any novel advice for you, Forlorn & Forgotten. My instinct is to tell you the usual: give yourself time. Grieving is a mysterious process. I think the only real tool we have to process the hurt of loss after a breakup is lots, and lots of time. I’m in the midst of a breakup from a relationship of nearly 7 years right now. It’s fresh and complicated--my own breakup wasn’t particularly contentious, either (that I know of). And yet, my ex and I find ourselves bickering, holding each other at a tense distance while we figure things out. We still offer each other snacks and Diet Cokes and do tiny favors for each other. But now, there’s a wall. A wall that was necessary to build, but a new wall nonetheless.

The desire to distance ourselves from each other coexists with a longing – I miss the ease of someone familiar and warm. If there’s anything dykes know how to do it's linger, miss each other, and want to stay. It’s hard to imagine myself beyond this moment, for the two of us to find that ease we had in our old relationship, but I know that it is possible. Maybe not the same familiar ease, but a new one forged between old friends who’ve been through some intense shit together.

Some real advice that I tell myself often: this moment does not indicate some greater absolute truth. You are not alone, you are not doomed to be alone, and the ending of something good does not mean good things can never last.

I find that throwing myself fully into the absolute mystery of this universe, of human emotion, is helpful. I don’t fight the sometimes-overwhelming melancholy. Instead, I unclench my jaw, unfurl my fists, and force myself out of the urge to understand why, why, why? I trust that even in the pure chaos of nature, patterns arise: tides rise and fall, ebb and flow. Right now you are feeling forlorn and forgotten, but, if you give it enough time, the pattern will emerge. The tide will return. You will feel happy and held once more.