Homo Erotica

Five Tips To Losing Your Anal Virginity With Aplomb

As the world prepares for gay art student Clayton Pettet to publicly lose his anal virginity in London on April 2, we thought we’d offer a few tips to the 19-year-old performance artist, and other gay men who may be thinking about handing out their coveted V-cards.

Bottoming is a rite of passage most gay men make at some point in their lives. (Unless, of course, they’re analphobic or one of those boring “total top” types. In which case, they’re seriously missing out.)

It can be a scary thing, but it doesn’t have to be. Some people, especially fundy Christians, see virginity as some kind of trump card to hold over potential suiters, a sacred act that must take place only after marriage. We don’t see it that way. For gay men, it’s usually simply another of many awesome firsts, like your first great French meal, your first drink, the first time you hear a Madonna song, or perhaps even watching your first football game.

Here are five tips to help make your deflowering a pleasant experience.

1. Finding your fellow

We like to think of losing our virginity as this magical thing between two people who are deeply in love, but the reality is, very few of us actually keep in close contact with the guys who popped our cherries. Chances are five years from now the closest relationship you’ll have with the man who holds your V-card is a Facebook friendship, if that. And that’s okay.

That being said, you probably don’t want to lose your virginity to any old Joe Schmo off the street, although that actually sounds fun now that we mention it. Seriously, don’t agonize over finding someone special and being in love and all that like an evangelical might.

Avoid other fumbling virgins. Just locate a decent-looking, trustworthy guy whose danced the chocolate cha cha once or 500 times before so he can show you the steps. And this is probably the last time you will ever not be a size queen.

2. Location, location, location

The place where you first have your peanut butter stirred is also important. For the rest of your life, the topic of how you gave up your V-card will undoubtedly arise at parties and other social gatherings, and you want to have a good story to tell.

“I lost it in the penthouse suite of a 5-star hotel,” is sure to impress people.

“I lost it in the back seat of mom’s minivan.” Not so much, although that would work, too.

3. Cleanliness is next to godliness

We’re about to get down to the nitty gritty, so brace yourself, virgins.

An unclean butt has a way of instantaneously killing the mood. So wash, wash, wash. And then wash again. If you are doing it publicly as performance art, you might want to repeat the procedure one extra time.

Losing your virginity is stressful enough. (Side note: We like to think of it as gaining a sex life, not losing anything worthwhile.) You don’t also want to be concerned about having an accident on your maiden voyage down the Hershey Highway. One way to reduce this fear is by conducting an enema 30 minutes to an hour before engaging in anal sex.

How does it work? Easy. You insert the tip of the enema , squeeze the water, hold it in for a minute or two, and then release. Full disclosure: Doing an enema isn’t pleasant, but it takes less than five minutes and it makes for a nice clean dip in the pond. If you are feeling less than solid due to the nerves, you may want to pop an Imodium or three.

4. Condoms, lube, and more lube

Condoms are good. Use them with an ample supply of latex-safe, water-based lube. The bottom line (pun intended) is this: The first time a man plows your backfield might involve a little pain. It will be much less painful, however, if you slather yourself up beforehand. You may also find loosening your sphincter with a finger or three helpful, or using a toy, like a dildo or small plug. Of course, the best way to relax is with a good old fashioned rim job, which your top will likely provide with gusto. (After all, it’s the polite thing to do.)

If you are one of those guys who is hell bent never to use a condom, make sure to talk to your doctor about PreP first.

5. Relax and enjoy

After a minute, discomfort subsides. Granted, it can feel like the longest 60 seconds of your life, but once you get through it, it’s done, your muscles have relaxed, and all you can think about is the deeply pleasurable sensation happening in your loins.

So take a deep breath, throw those legs in the air, relax, enjoy, and welcome to the club!

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  • Billy Budd

    I am truly versatile. I like to bottom for older guys and top the younger ones. But sometimes I flip flop. Everything depends on the partner. My orgasms are more intense when I am being penetrated.

  • Captain proton

    With regards to #1, it is better to find someone fully aware that it’s your first time and not some self absorbed hot party animal who will plow into you with no regard to how comfortable and how ready you are.

  • Billy Budd

    You should choose a guy with a small dick for your first time. It is the best thing to do. It won’t be traumatic.

  • Tackle

    Thank you for saying those boring “total top” types. So true.
    And about Clayton Pettet, the art student who will lose his virginity on April 2nd , probably with thousands watching. Take extra precautions, and not only use an enema. 30 min to an hour before the act, I suggest not eating the day before. Since this will be such an event, even with his parents watching, you don’t want this to be a sh!tty experience…

  • sonofabee

    I would add an additional tip to this list: get a dildo and practice with that for a while before you do the real thing.

    A decent quality 6″ dildo can be found for around 10 or 20 bucks. You’ll need condoms and good lube anyway so you might as well buy some while you’re dildo shopping.

  • DonW

    Nice, common-sense tips — but as for Clayton Whatshisname, I’m not sure how much of “the world” really cares about this yawn-fest of a publicity stunt. Personally I’d rather watch lesbian porn than give some self-absorbed, talentless art f*g another set of eyeballs.

  • Sweet Boy

    Close your eyes and think of England…

  • coltonblack

    Like the tips. Wish I would have known these my first couple of times around when I topped a dude so he would not feel so much pain.

  • misterhollywood

    Pretty cool post. And love the photo of the guy with the “come join me” look:)

  • jwrappaport

    Not to sound corny, but I’ve only ever enjoyed it when I love the guy on top. Every other time it’s been terrible.

    @Sweet Boy: Beat me to it.

  • Billy Budd

    I agree that when you love the guy whos on top the experience is different. I had a boyfriend who had a hugh dick and I never felt pain with him, only lots of pleasure. I would almost cu m without touching myself.

  • sonofabee

    @jwrappaport: I don’t think that’s corny at all. There’s actually a lot of science and research that supports it. (not specifically in regards to gay men bottoming, but more generally in regards to whether or not people enjoy sex, whether or not they’re able to have an orgasm, whether or not they find it painful, etc).

  • DarkZephyr

    Is that top image from Corbin Fischer? Careful Queerty or they might have a cow and sue you. You yourself have reported on their litigious ways.

  • ait10101

    I lost my virginity at 11 with my best friend. I didn’t even know what “losing your virginity” was, so it is hard to say I lost anything. I don’t know what the big deal is supposed to be.

  • bmwblonde

    As usual, Queerty is puffy-fluffy, incomplete and shallow.

    So here’s the best trick for easier bottoming, especially for that first time you’re playing Catcher for that cute Pitcher. There’s a little trick of biology that Queery (oops) forgot (duh).

    If the “Catcher” draws his knees up towards his chest (both players on their sides is good, for virgins), your normally “S”-shaped anal passage straightens out quite amazingly. Thus the Pitcher’s dick doesn’t have to PUSH the “S” shaped muscles into alignment. WAY EASIER Hello?

    Sheesh. I bet the editors of Queerty are all about 12.

  • NoelG

    @bmwblonde: Get over yourself. This article in no way pretends to be comprehensive. You list one of dozens and dozens of details that could have been added and you think that’s a good opportunity to act snide.

  • gayarchitect

    I lost my man-cherry in Eugene, Oregon to a swimmer! I never got his name, but he was very handsome and built.

  • NoelG

    In descending order of importance:
    1. Cleanliness. If you are going to bottom regularly, invest in an enema bag or shower attachment to make the process easier. A deep cleansing will take several repetitions but it is worth it to know there is no chance of an accident. Knowing you are totally clean is hugely important in being able to relax, be in the moment, and just enjoy getting worked.

    2. Lube. Lube. And more lube. It’s a good idea to buy one of those injectors and fill yourself with lube.

    3. Toys. It’s all well and good to look for that super-patient guy who will take his time and go at your pace as an inexperienced bottom. It’s better if you can be a hot bitch who can take a good c*ck.

    As a good bottom, you will become familiar with your body in a special way from the food you eat to the rhythms of your digestive tract to how to properly cleanse yourself to the enjoyment of your sphincter muscles, anus, etc. as erogenous zones.

  • Fang

    Great tips! Though I have to say, as I become a (very) experienced bottom, lube isn’t a necessity. And sometimes i like it more without and getting prepped with a nice long rim job.

  • TampaBayTed

    There are enough bottom nowadays to go around hundreds of times over. Just take a look at the sex ads on many gay sites. A large majority identify themselves as bottoms. That can make the smaller number of tops happy, but give me versatiles any day.

  • Tackle

    @bmwblonde: Your attack is unwarranted and uncalled for. Save that for when it’s called for. Sometimes it is. Such as when Queerty puts someone down because of a physical appearance, or when they race-bate. Which I have gotten on them many times for. But this should be puffy- fluff and iincomplete. It’s not a directory or manual for first time male ass virgins. It’s just lighthearted fun. And with all the crazy sh!t we deal with in our everyday day life, this is a welcome relief.

  • lion_king

    Are you actually recommending people have anal sex for the first time without a condom when that study showed it only cut the rate of HIV transmission by 49%? Not that people will treat these steps as the bible but pretty irresponsible don’t you think??

  • joey

    ahh it can feel good but it comes with a lot of work and an enormous cost should anyone fuck up even one time. its not all that safe, eventually it seems many guys dont have a condom or want to try it without one…guys lie about their status and condoms tear. i ended up getting hep b somehow probably from fucking and i ALWAYS USED A CONDOM. now i have to take some med (tenofovir ?)everyday so much for condoms ..i just stopped fuck 2 yrs ago it sucks i miss it but i’m not that stupid to continue to push my luck

  • avesraggiana

    In my experience, all enemas and anal douches have ever done is make an even bigger mess than the one I was trying to avoid. What’s worked best for me is to eat a high fibre diet. I even go so far as taking psyllium fibre husk with a drink everyday. Since taking this stuff, I’ve never suffered the indignity of soiling, mud tracks or ass boogers. Psyllium fibre husk – it cleans you out, and it works you clean every time.

  • Stache99

    @joey: You don’t get hep B from fucking. Give it a break man. Jeez.

  • Stache99

    @avesraggiana: That’s great advise. I usually take the psyllium fiber cookies. They actually taste good.

  • Geoff B

    Missed the one where when a guy tells you how straight he is but leaves with you anyway, don’t worry about any of this because you’re gonna be the top.

  • Ryan26pdx

    My first time was stellar. I learned from my friends’ horror stories in high school and ended up waiting until college. I didn’t lose it to the love of my life, but I properly “prepared” before my first college party and ended up having a lovely experience with a guy who I’m still friends with.

  • Pistolo

    My first time was smooth sailing. I only experienced pain the morning after and it really wasn’t that bad. I was topped and he knew what he was doing. That’s key. If you’re not experienced then it’s better than -he- is so he can show you the ropes.

  • vive

    @Geoff B, you are so right! Any straight guy who visits gayville just desperately wants to be the bottom. Can you blame them? Not having to do all the work and take all the responsibility for once, as they have to do with women. It’s like a sexy vacation to them.

  • vive

    @joey, you bring up a good point. All gay guys must get vaccinated for Hep B and also HPV (Gradasil). I think Hep B might be a standard vaccination nowadays but Gardasil isn’t yet standard for boys, so we should all take the responsibility and go to our local STD clinic and ask for the vaccinations, even if you have to pay for them yourself.

    I am of a generation that wasn’t vaccinated and also got Hep B somehow despite always having safe sex at the time. In my case I had no symptoms and my body cleared it – i only found out I had had it when I aksed for the vaccine and they tested me and found I was already immune due to “natural exposure”, so no harm no foul, but some people get the chronic version and that’s no fun. Having learned my lesson, I paid myself to get the gardasil vaccine recently.

  • vive

    @NoelG, watch it with the toys. There is nothing quite as disappointing as a bottom who is too loose. :)

  • joey

    @Stache99: you most certainly can get hep b from having sex. hep be is transmitted by exchanging body fluids including blood and semen. i never used needles and it wasnt passed on to me from my mother. go look up how a person can contract hep b, it specifically mentions MSM as a higher risk group

  • gaym50ish

    To me, it seems irresponsible to use the terms the homophobes use to describe anal sex. By referring to having your “peanut butter stirred” and calling the anus “the Hershey Highway,” we simply reinforce our critics’ misconceptions about what we do in bed.

    During a hearing on a proposed repeal of New Hampshire’s gay marriage law, a state representative named Nancy Elliott said, “We’re talking about taking the penis of a man and putting it in the rectum of another man and wriggling it around in excrement.”

    Well, no, we’re not talking about that (and what does it have to do with marriage anyway?) except for a few fetishists who is into scat. But this is what people think — that it’s the ONLY thing we do in bed, and that it’s a very messy business. We don’t have to give them ammunition to stand up in a legislative body and claim that we shouldn’t be allowed to marry because gay sex is gross.

    Enough with the “Hershey highway” references.

  • sonofabee

    @gaym50ish: Well said. And the esteemed legislator from New Hampshire should be reminded that plenty of married heterosexual couples do exactly what she so vividly described.

  • Billy Budd

    Here in Brazil, heterosexual men are obssessed with female butts and anal sex. Brazilian guys like to take a woman from behind, on all fours, and have complete control over her.

    Anal sex is also heterosexual sex. People seem to forget it.

  • Throbert McGee

    @gaym50ish: “To me, it seems irresponsible to use the terms the homophobes use to describe anal sex. By referring to having your “peanut butter stirred” and calling the anus “the Hershey Highway,”
    Well, that’s a good point. What about just saying that anal sex has an intrinsic Dom/sub component that isn’t generally present in oral 69 or in mutual masturbation; that anal bottoming is ALWAYS a split-second and a half-inch too deep from crossing into “masochism” territory; and that “After a minute, discomfort subsides. … once you get through it, it’s done, your muscles have relaxed, and all you can think about is the deeply pleasurable sensation happening in your loins” is a bit of an exaggeration, to put it mildly.
    And you might add — because it’s the truth — that there are often brown stains and “santorum” involved, unless (and even sometimes when) the bottom has troubled himself to use an enema. Which is to say that “the Hershey-Nice-Little-Garden-Path” would not be entirely inaccurate, even if “Hershey-Highway” is a definite overstatement.
    P.S. Thanks to Billy Budd for mentioning the control and domination aspect that often plays a role in anal sex. In my experience, people who have actual vaginas rarely prefer to take it in the anus, because doing it vaginally feels much less unpleasant and submissive.

  • Billy Budd

    @Throbert McGee: Don’t forget that women do not have prostates. Anal sex stimulates the prostate and results in more intense orgasms. This is a fact. It may hurt, but it is also pleasurable. Women do not get as much pleasure in anal sex as men do.

  • colin4

    well I guess I should stop lingering on with that task of me now n just find myself a partner soon cuz I dnt think startin relationships go long term eithr

  • Chaz

    I’d really like a lot more detailed info on point 3. I’ve only ever topped but have never ruled out bottoming. I’d like to know in absolute detail about the products and how to prepare as when the time comes I want to relax and feel that’s been taken care off.

    On the issue of condoms in point 4, I am having trouble finding one that fits and works consistently. I’m not sure if other guys have the same trouble but day after day using exactly the same brand seems to provide different sensations and results, many of which kill the mood, so much so I’m actually thinking of going without, something I’m very nervous of doing…

  • murphy0071

    @Billy Budd: NO. Small penises tend to fall out and cause abrasions to the anal sphincter. At least five to six inches is best with someone who knows how to plow.

  • Dominick68

    I do not see this as helpful enough. This should have been more complete, in other words. On the other hand, I am happy to be corrected by someone who does enjoy receiving as to what I’ve written should have been included, which see below:

    My biggest ‘concern’ is that there is too little description of how those receiving can avoid pain and achieve pleasure.

    My understanding is that there are two muscle rings. The sphincter is under conscious control, but the one further inside (name?) can never be under conscious control. For that second muscle to relax so there will not be any injury or pain, ‘medium’ pressure must be continuously applied for around a minute. If true, this information needs to be known of and made use of for the experience to be pleasurable for the first-time bottom. It seems that learning and practicing through the use of a dildo or other kind of prostate stimulator would be ideal.

    As for me, I have tried but never once succeeded in getting pleasure from being the receiver. This came as a big disappointment, actually. My best guess is that how my prostate is situated the ‘issue’. (An aside: I think that sex acts should be pleasurable for both lovers, so I do not think that straight couples should ‘have’ anal sex since women cannot possibly orgasm from receiving.)

  • Trippy

    One word: poppers.

  • glnic1

    Just hoping for some advice from you guys. I douche/enema onoccaison for deep long lasting anal sex but sometimes found that while i manage to get very clean i will sometimes have a small amount of water remerge once we hey started. It’s clean but spa the momentum. I like to clean beyond just the rectum because we can be at it for hours. Any ideas how i can make sure that last bit of water is out?

  • petensfo

    I gotta say, I’ve never douched my butt. Very occasionally, there’s a little mess, but sex is dirty sometimes. The few times I even tried an enema or something, as others have stated, it made things worse: wet farts, or worse. I eat right & stay regular, but unless you’re chasing a donkey-dong, I’ve just never found it necessary.

Comments are closed.