Midnight Cowboy

My name is Alexander Cheves. My nickname is Beastly. I write about sex. I wrote a book.

Have a question? Email askbeastly@gmail.com or go here.

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I am a 25-year-old gay man who has never had any sexual experience. When the time finally comes when intimacy is on the table, should I tell the man I am with about my virginity? Or should I just go with the flow and see how things turn out? The answer is probably different depending on whether the partner is a boyfriend or a hookup, maybe?

Hi friend,

In my first sexual experience, I told the guy I was a virgin. He was several years older than me and was able to teach me a little bit about sex — and, most importantly, he was able to prepare me for the trials of bottoming (namely, that I would make a mess, there would be poop, and that bottoming would hurt at first).

His experience and advice were helpful, and I can’t imagine bottoming for the first time and experiencing those things — exactly as he said I would — without his guidance and understanding. So naturally, I’d encourage you to have that dialogue with the person you want to explore sex with for the first time.

That said, I know it can be hard to find such a sex partner. Good sex partners are hard to come by, and beginners have to be choosy — there are bad people everywhere who would use your lack of knowledge against you. I still think the best course is to be honest with potential sex partners and tell them you’re new. That’s not as much of a turn-off as you might think it is.

In sex, as in life, the best policy is honesty. There’s no degree of sexual experience that is shameful or embarrassing. People with no experience are no more virtuous and certainly no less desirable than those with lots of experience. Being direct and honest with your sex partners is likelier to result in an enjoyable first time.

Just a heads up: Even with a good and patient partner, first-time gay sex experiences tend to not be great, especially for guys who want to bottom. All sex requires practice and takes time to master, so don’t beat yourself up if the first time isn’t flawless, and don’t obfuscate normal awkwardness and nervousness with shame. Many people find awkwardness and nervousness in first-time sex and these feelings immediately trigger their internalized shame — “This doesn’t feel right, so it must not be right” — and I know quite a few gay men who swore off sex for a bit after their first time. Don’t do that. Everyone — gay, straight, and everyone in between — has an awkward first time (and first several times). Sex will get better. Don’t let your inner shame voices kick in and tell you that you don’t deserve to have it.

Love, Beastly

Hey! How are you? My name is Sohan. I’m now 23 and I’m from Montreal, Canada. I found you online while looking for advice on anal sex and I’ve been following your Twitter page for some time. I really appreciate your posts and advice columns to help men explore sex and their sexuality!! I also found your other Twitter page that features your JFF, but I could not message you from there. And so, I’m DM’ing you here to ask for your help, if that’s ok with you because I am completely lost… I am specifically asking for help in the bottoming department.

I’ve never had sex (yes I’m 23 but still a “virgin” as many would say, please don’t judge me…) but I have tried playing with dildos. I really love the feeling of anal play! The largest one that I could insert however was 6”. Definitely not big, but I am very tight because I’m inexperienced so I can’t do much… I haven’t been able to play with myself for some time now so I’m back to square one: I can only insert 2, maybe 3 fingers.

I know that the only way to be able to take bigger dildos (and bigger dicks too, eventually) is to frequently play and gradually increase in size. However, I need your advice/tips/HELP when it comes to douching… I know it’s not the most glamorous of topics, but I am in need of your help and expertise in this department. I have read all of your posts regarding douching and bottoming, but there are still things that I am struggling with.

I wanted to ask how YOU prepare for anal sex when it comes to douching. I’ve read many blogs, posts, and advice columns that say that diet plays an important role in making the douching process easier. However, I seemingly still can’t get it right! I exercise 6 days a week, I eat all of my greens, I consume a lot of fiber (including the Pure for Men fiber supplements), I drink lots of water, avoid dairy, I don’t eat anything too greasy or that’s fast food and the only animal proteins that I eat are eggs, and occasionally chicken breasts!!! And I still cannot get douching down to save my life, which is frustrating and infuriating. And I don’t think a guy is ever going to consider being with me if I can’t even get douching done right.

I know that you’re very busy, but I would really, truly appreciate it if you could give me some advice on how you get prepared and how to should douche properly from your experience because I am clearly missing something.

My friend,

There is no shame or judgment on this blog. I will not judge you for being a beginner — everyone is a beginner at one point.

If someone is disinterested in you because your body poops, they’re not someone you want to give your heart or hole to. Every human being poops. At some point, you will have to work through the feelings of shame and embarrassment over a natural thing your body does, because even after you figure out your piping and learn what douching regimen works best for you, that shame will still be there.

As I’ve written elsewhere, no one can fully control the body. The cleanliness and douching industries have tricked us into believing that if we get the process right, we can fully be in control of our bowels, and this is simply not true. If you discuss anal sex with guys in their thirties and forties, you will find that many of them have learned that, even after all the special tricks, nothing works 100 percent of the time, and the tummy remains a mystery.

As we age, tummy problems tend to worsen (especially — based on anecdotal accounts — for men who have sex with men) and the gut tends to become harder to control. A lifetime of sugary diets, fast food, soda, booze, bad sleep, and just regular eating start taking their toll almost immediately after you stop growing (around 25 years old). So there is likely no golden future in which you’ve wrangled your tummy into total submission — the body just doesn’t work that way. Your tummy is great and your butt is great, but sometimes they don’t do what you want them to do. This means you are just like everyone else. And that’s okay.

I will share my personal regimen with the caveat that it’s my regimen — it works for me. I found it through trial and error over years, and it has evolved as I’ve grown. Like you, I struggle with douching and have a problematic tummy — I always have — and it’s gotten worse with age. I now have to be very selective with what I eat. I’m nearly on the “paleo” diet. I eat minimal bread and no dairy, but even within these restrictions, my tummy regularly likes to act up. I take the maximum dose of Pure For Men fiber supplements twice a day (three capsules in the morning, three at night) and I take a good probiotic once in the morning and once at night. The probiotic I am currently taking is Dr. Ohhira’s Probiotics, which a friend with similar tummy issues recommended, and I have to say they’re the best probiotics I’ve taken in my life. (Everyone who douches regularly should take a daily probiotic.) I have to order these probiotics as a monthly subscription on Amazon. I hate Amazon but this is the cheapest place where I can find them.

When I’m in the shower, my douching regimen is pretty minimal. First, the water is lukewarm. I tend to use a shower shot, not a handheld douching bulb — though a douching bulb works just fine. With a shoer shot — and with the water at a very gentle pressure — I hold the nozzle in my butt for five seconds, then immediately expel it. Then I hold it in for about ten seconds and keep it in, counting up to about a minute or whenever my body tells me it’s time to expel (your gut will signal when it’s time).

Holding the water in me sends a signal to my brain that there’s something in my rectum that needs to be expelled, which activates my gut to push along anything else that might be further up the pipe. I do this pattern — 5 seconds, expel, 10 seconds, hold, expel — three times at my best, though usually more. When I use a handheld bulb, I do the same: immediately expel, then hold, etc.

In total, my first douching session lasts about 15 minutes. Then, if possible, I relax: I go sit on a butt plug or lie down or do something to clear my mind and let my butt settle — ideally for about 45 minutes if I have the time. Then, before playing, I usually do one more quick check (5 seconds, expel, then 10 seconds, hold, expel) for three rounds max. By then I should be fine. If I’m not fine by then, I’ll shrug and say it’s simply not my day to bottom. I never over-douche or douche very deep. I have to protect my sensitive bowels and douching is terrible for gut health.

If I drink too many protein shakes, I know my douching regimen won’t be great. Regardless of their ingredients, protein shakes hit my stomach hard and make my poops looser. If I don’t drink enough water, I know my douching regimen won’t be great. I limit myself to one cup of coffee a day and I don’t drink soft drinks or anything carbonated. I generally try to avoid processed sugar, but I have a voracious sweet tooth, so this avoidance is my least successful. Even with all this, there are days when my tummy doesn’t behave. I’ve had many hookups where, after multiple attempts at cleaning out, I’ve simply had to say that my tummy was being grouchy and there was nothing more to be done about it. Most sex partners my age and older have been understanding in these situations — most have become aware that the tummy grows less obedient with age. (It is a beautiful thing to grow into a place of mutual understanding and care for other queer men that exists entirely separate from sex.)

It sounds like you’re doing close to what I do. If my regimen doesn’t work for you, book an appointment with a gastroenterologist — preferably one who specializes in LGBTQ care or, better yet, is themselves queer. You don’t need a homophobic man in a white coat telling you that your problem is because you take dick up the ass, because that’s bullshit. Anal sex has been around since humans first started fucking — it’s natural, safe, and good for you. Douching as a common pre-sex practice, however, has been around for less than thirty years — if that. Douching is not natural and not good for you, so you should work to minimize the douching regimen as much as possible — or skip it altogether and just clean up any mess you make after you’re finished.

I know bottoms who have Crohn’s disease, bottoms who’ve recovered from rectal surgery, and bottoms who have a host of GI problems. They all still enjoy great anal sex. Most of them have, through trial and error and doctor support, found a regimen that works for them most — not all — of the time. That’s the best you can hope for. That’s what we bottoms all hope to find.

And finally, let me say this: the idea of a totally shit-free hole, even after douching, is a fantasy. You will never eliminate all trace amounts of fecal matter from the rectum. If your last douche into the toilet has a few wispy particles but no big pieces, you’re clean — or as clean as you can get. It is very, very rare to poop out crystal-clear, spotless water after a douching session, and that should not be your goal. The goal of douching is to “declutter the runway,” not “scrub the walls” — to clear away the big pieces that would immediately be noticeable and uncomfortable. If your last douche release has a little bit of brown water but no big chunks, he will not notice and you will not notice. You are clean enough at that point to have great anal sex.

Douching before gay sex is far more standardized in the United States than elsewhere, which is an important thing to remember. Not everyone does it. You don’t have to do it. You certainly don’t have to master it before you start to explore sex. No one ever “masters” douching — we just get a little better at it with time and practice.

Good tops know what they’re doing, they know they’re playing in a butt, and they know that if they go too deep or too hard, they’ll hit pay dirt. It’s part of the fun of being a top — sometimes you’re going to get shit on your dick. Tops: if you’re fucking someone up the ass and his hole is giving you pleasure, trace amounts of poop are part of that pleasure — unavoidably so — so get over any fears you have of poop, or do something else.

My friend, you are ready to explore sex — and you should. Sex will get easier with time and practice. Try not to be terrified of it. Allow yourself to enjoy it. Your body is the greatest instrument of pleasure you will ever own.

Love, Beastly

Hey Beastly,
I’ve always appreciated your blogs. I was wondering, as I’m someone with no romantic experience (dating or sexual) if you had any advice for navigating how to date or hook up. I have a fear of driving too, so I have no idea where to begin.

Thanks so much for writing these!


I sympathize — I have a fear of driving too, and I can’t get on a plane without anti-anxiety medication. I have terrible claustrophobia (which, oddly enough, manifests as an irrational fear that I’ll suddenly shit myself in public). It’s not accidental that I moved to a city with the best public transit in the U.S., and I decided shortly after moving here that I would never own a car again.

It might sound urbanist to tell you to move to a city with public transit, but that’s my best advice because that’s what I did. You could live in a small city like Savannah, Georgia, where you can easily bike from place to place, or you can live in a large city like New York, London, Chicago, or Washington D.C. with good public transit. To live in the suburbs or in the country is to agree to the condition of driving everywhere — to chain your life to cars and depend on them for dating, sex, groceries, entertainment, and all other parts of living. I could not agree to those terms, so I am effectively banished from suburbs, small towns, farms, and cute mountain cabins. As much as I love nature, I imagine I will spend the rest of my life in cities where owning a car is not necessary.

These conditions of life are things we must think about as adults, and they are not things to disregard or put off till later. Your life is happening now, not later, and as mundane as these subjects may be, discussions on money, access, location, and other topics are intimately tied to sex, romance, intimacy, and identity. I believe that all queer people would benefit from spending at least a short period of their lives in a city — someplace with at least one gay bar and a small local queer community. I did this for the first time at college in Savannah, Georiga (which is, by the by, a very inexpensive city to live in) and this was vital to my development as a queer man. This experience taught me how to date with no prior experience — how to meet and, later, how to vet people.

The fact is, you will only learn from experience, and some of those experiences will not be pleasant, and those unpleasant experiences you will learn the most from. We learn what to look for by learning what not to look for, and we learn what not to look for by going home with (or going on dates with) people who end up being mean, dishonest, judgemental, narrow-minded, immature, or just plain shitty. Having a populace to learn from is key to this experience: what will appear, at first, to be an intimidating bunch of strangers will reveal themselves in time to be friends, acquaintances, lovers, nuisances, people to talk to, people to pursue, and people to avoid. This learning-by-immersion will slowly reveal your own preferences and nature to you by way of contrast: every person you meet will sharpen the features that make you singular and will hone your ability to recognize your own wants and desires.

It is a known queer narrative arc that we escape to cities to join the queer community during our coming-of-age — nearly every stereotypical gay movie has some version of that plot, and many not-gay ones do too. From classics like Midnight Cowboy to queer classics like The Birdcage, Hedwig and the Angry Inch, Cabaret, and Paris is Burning, movies tell us what we know: we find others in cities. Sometimes you have to escape where you are and go to where you can be yourself — and for people like us, that usually means a city. Queer people still do this today, and likely always will.

I recommend finding your closest city with a decent gay population and moving there as soon as possible. If you can find a job before you move, great, but sometimes you just have to go cold: find a friend or relative who has a spare room or couch you can crash on for a week. Live out of a suitcase. Make it work. The first weekend you’re there, go to the nearest gay bar. You don’t have to talk to anyone the first time you go to a gay bar — you can stand against the wall quietly, watching, and try to slip through the crowd unnoticed (that’s what I first did). Visit the gay bar often. In less time than you think, the space will feel less threatening and you’ll feel ready to start talking to people. Dating and sex will come — don’t force or rush it.

You will make mistakes. You will grow. And most importantly, you will be extremely grateful that you did this — that you made the prototypical gay journey and went where there are others. In a few years — after you have some dating and heartbreak and good sex behind you — you can decide if you want to move back to the suburbs or to the country.

Let’s talk about money. Cities can be expensive. But I think it is better to live a little broke during your youth in order to learn about your queer community than to stay in an isolated place saving up for the day you can move somewhere with more financial ease. You will find that many adults who plan to do the latter — who plan to save and move somewhere with more gays, eventually — never actually make that move. They get stuck, bills pile up, responsibilities pile up, and they become adults who dream of what life might have been like if they had gone. It’s never too late to join the queer community, and older folks find their way to us every day, but no one is promised tomorrow. Go now.

Love, Beastly


  1. Hello, if you had to compare and contrast NYC and Savannah and choose one, which do you think would win? Your book has me leaning heavily towards Savannah, but the Big Apple is such an icon.


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