Practice Round

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

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I just read Fuck Your Way Into Confidence. The guy was in his 30s and coming out late. I am a gay male, almost 70, and came out about a year and a half ago. I was in the closet for over 50 years, living in fear and self-condemnation because of my intense, lifelong evangelical religious environment. I married a woman (who I dearly loved) at age 23, and we had three children. We were married for 39 years before her death. Finally being able to be myself has been absolutely incredible. But, I don’t want to die a gay virgin. I have fantasized for so long. I want to know that full-body intimacy that I was made for and never have had. Some days I feel really desperate. Where I live (rural Midwest) you can barely find any gay men, let alone someone my age. I’ve been told that experienced gay men are not interested in breaking in a “baby gay.” I am hoping to move to a larger city, but I don’t know if that will change anything. You mentioned being supported by pillars (or not). I know my physical appearance is a weak pillar. I lost a lot of weight (more to go) but now I have loose skin. I am very aware of my age and my looks when it comes to thinking about having sex. I do have other pillars. I am returning to a graduate program and will be starting a new career after I graduate. I love to write, prose and poetry. I am in a better place mentally than I ever have been in my entire life. But I don’t think I will ever feel complete as a gay man until I can be active sexually. I would appreciate any advice.

Hi Larry,

It is great to hear that you are in a good — or at least improving — mental place. Healing from an evangelical background is never easy. I am proud of you.

You predict what I will suggest: leave. You do not have to move to a big city. I do encourage cities (I think every queer person would benefit from spending a few years in one) but few people can afford New York City or Los Angeles. It does not matter where you go. You just need to go somewhere there are others, somewhere with at least one gay bar.

A gay bar is evidence that your people are nearby. Gay bars exist in cities across the United States and across the world. They can be found in small towns in the South, like Savannah and Charleston, and they are dotted through the Midwest like safety beacons. And, of course, they are densely clustered on the coastal cities of the U.S. The existence of a gay bar proves the existence of a local gay population.

(Beastly’s Note: a kind reader had some additional advice shared after this post was published, which I am adding here: “Something that may be worth mentioning to Larry and other rural queers (specifically guys, since a lot of these spaces are either male-dominated or men-only) is the existence of gay campgrounds. I am a 20-something queer woman so my insights are limited, but based on the campground that I have been to, there are a lot of older men compared to the bar and circuit party scene, and many guests are rural gay men for whom the trek to their nearest city is inconvenient, so Larry and others like him may feel right at home making friendships, hooking up, etc. at the gay campgrounds during warmer months. is a good starting point for finding campgrounds, although there may be others.” I can agree to this. I have been to some wonderful campgrounds. Some are quite fun. Some are clothing-optional. Gay campgrounds support the point I’m making here: you need to go where you know there are others like you.)

When queers feel trapped — as we often do — leaving is a brave, difficult, and life-changing choice. The reason I tell people to leave their small towns and go to cities is not part of some urbanist agenda, though it might seem that way. When your identity is shared by a small sliver of the population and you want to find others, you simply have to go where you will better odds of doing so. That’s not fair, but that’s the reality of queer life. That’s why queer meccas exist.

Cities are hard. But this is the classic queer trade-off: we tend to exchange the comfort of a quieter life for the migraine of an urban capital because that is where we find sex, freedom of expression, and people who understand us. There’s no rule saying you can’t find all this in a small town, but cities exist for many reasons including this important one: they bring lost, uncertain “others” together and turn rejects into tribes.

This is equally true for people who are not queer. If you live in an isolated place and happen to be a hardcore goth or aspiring ballet dancer or future fashion designer, you have a choice: you either suffer being disconnected or you go where there are better odds of finding your people.

It is not fair to tell you (or anyone) to uproot your life for better odds. But loneliness is brutal. We are not meant to be alone.

Larry, there are many men all over the world like you. You have no idea. There are truly countless men out there who share your story. They are older, have insecurities about how they look, and are newcomers to gay sex. They are new to being out after decades in the closet, and they are looking for men just like you. They want someone like you to explore sex, love, and intimacy with. You simply have to go find them.

Straight people never have to think about this stuff. The world is made for them. They crawl the earth in droves. They move through life on the guarantee that everything is for them, because 99% of the world is. Can you imagine assuming that every pop song reflects your sexuality? I cannot. Like you, I am an outcast in the world. I am a kinky, non-monogamous, polyamorous fist pig with a long list of fetishes, which means I am an oddball even among most gay men. I live in the fringe of a fringe community. My nature forces me to hunt for others who share my oddities. It is a lifelong pursuit: finding one’s people.

But really, what else is life for? Our lives are a string of entanglements, not solo journeys. So I encourage you (and everyone) to do what is necessary to find your tribe, and it is a sad but unavoidable fact that the necessary thing often involves leaving the places that are familiar and going to places that are expensive. There is no way around that ugly fact. Wealth, access, and privilege play massive roles in how connected queer men feel to others, but that’s the world we live in. Home is made, not found, but for a gay man, the bare minimum requirement for home is, I believe, a few other gay men.

The perks of cities — even smaller and more affordable ones — include greater access to gay sex workers. A gay sex worker could help you right now. Sex workers go to cities because that is where the work is. A sex worker could give you practice (and practical feedback) that would boost your confidence without all the messy emotions of dating and romance that can muddy the experience of just learning how to fuck.

With a sex worker, you would not have to worry about the sting of rejection that everyone feels at some point on the sex hunt. Right now, a sex worker is worth the price. You can ask a sex worker questions — we tend to be good at answering them. I’d encourage you to hire someone older who’s been in the business for a few years and is more established, not a kid just trying to make some extra cash.

I did not grow up in cities, so I have never fully adjusted to them. I grew up in open space – farmland, African bushland – and I breathe better when I can look out a window and see nothing but land. But open land has become synonymous in my life with the certainty that I am the only one like me for miles around. That feeling of disconnection and isolation was my youth, and I would rather die than return to it. Someday I might exhaust myself of cities, move to a cabin, and live out the rest of my life surrounded by trees and nature. That is where my soul truly rests. But for now, I need my people, so I go where I have better odds of finding them, where I can beat the odds stacked against guys like us.

Good luck.

Love, Beastly

Hiiii! So im about to have my first sexual experience but I don’t want to go to the drug store and buy a douching item because you know what if my parents find out. Would a water bottle work and if not what alternatives are there?


Drugstore enemas are disposable, so you can toss it in the bin when you are finished, but I understand fearing that your parents might find it in the trash.

To answer your question directly: no, water bottles do not work well for douching, though certain products make them work better. But if you are worried about your parents snooping through your trash, I would probably not advise ordering something in the mail.

Online, you can find douching nozzles that screw on to water bottles, but these are better for a quick check at a club or bar and should not be used as a primary douching tool. These silicone “water bottle” douche nozzles easily fit in your sock or underwear. (The brand Boneyard was, I think, the first toy brand to make one of these “water bottle douches” but many others do now.) If you have one of these and need to do a quick check in a club or bar, just buy a bottle of water, take the nozzle from your sock, and do a quick douche — the water will be cold, no way around that — in a bathroom stall, then go get fucked. The downside to these is that not all plastic bottles are the same size. Their mouths vary in size between soda bottles and standard water bottles, and that’s just in the United States. The next club you visit could sell some strange, off-brand water bottle that doesn’t fit the grooves of the nozzle you have. So again, this is a backup douche, not a primary douche. And all this is useless information for you, my discreet friend, because again, you probably do not feel safe ordering something online.

A more expensive alternative: you can buy a nasal irrigation kit — the bottle version of the classic Neti Pot, the NeilMed Sinus Rinse, which can be found at most U.S. drugstores — which is more expensive than a standard drugstore enema but makes a great last-minute butt-cleaner if you have nothing else. The downside is that you should not use it to rinse out your sinuses after using it to clean your butt, even after a thorough wash (imagine inhaling micro particles of poop). But if your parents were to find it, you would be able to say it is verifiably not a douche, especially if you kept the original packaging.

Douches are used for many reasons besides prepping for anal sex, but I understand your concern. I remember life in the closet, when I felt like any discovery, no matter how small, could upend my life (and, eventually, one did). I hope you reach a point where you are no longer living with your parents and are safe from them so you can explore sex without having to worry about this stuff. This is no way to live. Get out as soon as you can.

Love, Beastly

Hey Alex,

I’m a bicurious college student with a lot of anxiety about sex. I have a crush on this guy (first time that’s happened) and I keep thinking about having sex with him and with other guys but I’m not sure I’m ready. I ventured into porn and was really freaked out by how rough it is. I want sex to be gentle and sweet, two people making love in each others arms. I know porn is a fantasy but it helped me realize I want intimacy more than anything.

When I start having sex with guys (because I do want that at some point) do I need to establish these things beforehand? If I tell someone I’m a virgin how do I know they’ll treat me right instead of trying to take advantage of me? During a really rough week I considered hiring a sex worker but I don’t even know where to start and I would rather find real connection anyway. Did I mention I have a lot of anxiety?

It’s been about 8 months since I started accepting my sexuality and your columns have been really helpful for me. Being comfortable with my emotions and my body has taken a long time and I’m glad someone’s there who understands that.

Thank you, Alex.


Hi L,

Thanks for the kind words. Hiring a sex worker is always a good idea. As I told the gentleman above, a sex worker can be a test run for the “real thing”. Speaking as a sex worker, I can say for certain that none of us would be offended at the idea of being a practice round.

I have said this before on this blog but will say it again: sex workers are great for virgins, especially if you hire someone more established. An experienced sex worker (or escort, or whatever term you are most comfortable with) has had many conversations with clients about desires and expectations. The experience of talking about sex with someone who can lead that discussion (a sex worker) will be valuable, because some version of that conversation should happen before most sexual encounters.

If you want gentle, intimate sex, you should have gentle, intimate sex, and you should tell all potential sex partners that is what you’re looking for. A sex worker can give you some practice in doing so — in talking about what you want.

Porn is a visual medium, which means it cannot convey all the other senses that are involved in sex. Rough sex, jackhammering: these things look hot on camera, but few people — tops as well as bottoms — actually enjoy sex like this. The kind of sex that really makes people moan doesn’t look intense on camera. Porn stars perform fast, hard sex to convey intensity, and the pleasure is faked. Porn has resulted in generations of tops who think it’s good to slide in and immediately start fucking roughly. When someone does this to me, I assume they are a beginner and have been mostly watching porn, not having actual sex. Porn has created countless bottoms who think they are lacking in skill when they can’t fuck hard, as if hard fucking is somehow an ideal form of gay sex. It’s not.

A good, well-established sex worker knows all this. A good sex worker can give you a taste of the sex you want. Between the sex you crave and the necessary pre-sex dialogue, a sex worker can be a guidebook to intimacy, which is why it’s odd to me that people assume a sex work experience is not intimate. Our entire job is intimacy.

In general, I recommend being honest about your virgin status, but some people disagree with me on this. I have heard many great “first time” stories that happened so well exactly because those folks said nothing about the fact that it was their first time. So there is no one-size-fits-all rule here. Everyone gives advice based on their experience. My first time having penetrative sex was, while far from perfect, a success because I told him I was a virgin. He prepared me for the less-than-comfortable parts of gay sex (he warned me that there would be pain and poop, and there was), and I am indebted to him for that. I understand that not every first-time playmate is as kind and generous as he was.

I was talking to him on a regular basis, and we were friends. So I suppose there lies my recommendation: a first-time experience with someone you know and trust will allow for more honesty and vulnerability over an anonymous hookup from Grindr. You can have a great first time with a headless torso, but I would not tell him (a stranger) that you are a virgin. You don’t need to have a relationship with your first fuck, but some connection would help.

Most first-time anal sex experiences are not great. Like any other life skill, sex gets easier and more enjoyable with practice. Don’t give up. Keep fucking.

Love, Beastly

1 Comment

  1. Hi there! Something that may be worth mentioning to Larry and other rural queers (specifically guys, since a lot of these spaces are either male-dominated or men-only) is the existence of gay campgrounds. I am a 20-something queer woman so my insights are limited, but based on the campground that I have been to there are a lot of older men compared to the bar and circuit party scene and many guests are rural gay men for whom the trek to their nearest city is inconvenient, so Larry and others like him may feel right at home making friendships, hooking up, etc. at the gay campgrounds during warmer months. is a good starting point for finding campgrounds, although there may be others.


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