Being Loose Is So Much Fun

I’m Alexander Cheves, a writer, author, and sex educator. My nickname is Beastly. I give adult advice on this blog — no question is off-limits. To ask me something, email AskBeastly@gmail.com or send a message via the Ask Beastly contact form.

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Hello Alex,

my name is N**** and a few weeks ago I discovered your video on “10 Tips for Better Gay Sex” on Youtube.

I really wish I had seen it when I first started having sex, I am very grateful that there are people like you producing content that I consider to be essential for every person who is having anal sex.

I really admire the maturity and the responsible manner in which you can talk about anal sex. Thank you for that.

I am writing to you today, because I would like to follow the advice on the video and train my anal sphincter by using a small butt plug. I have two questions on that:

– Is there a specific material the butt plug should be made of? Do you recommend one in particular?

-How would I make sure that by using it I will not eventually become too loose?

I look forward to hearing from you.

Hi N****,

Thanks for the kind message. I recommend sex toys made of premium silicone, glass, and stainless steel. If product specs say the toy is made of “TPR” or “TPE,” I don’t recommend it. Some TPR and TPE products are okay, but most, in my experience, are not.

You don’t have to spend a ton of money on a starter plug. One of my past clients, Fort Troff, makes great butt plugs (usually with great vibrating features, which relax your butt muscles) in many starter sizes that are good quality and fairly affordable. A beginner size plug is between 2 – 5 inches (5.08 cm – 12.7 cm) in insertable length and 3 – 6 inches (7.62 cm – 15.24 cm) in circumference.

On the slightly cheaper end, Doc Johnson has been a leader in the sex toy biz since the seventies and has an extensive list of quality products, and you can always find something good at eXtreme Restraints (including decent beginner kink and fetish gear). I support buying local, so if you have a local sex shop, go there instead of buying online — especially now during the pandemic, since many local sex shops are struggling. Keep the TPR/TPE rule in mind and you’ll find something great for a beginner.

If you want to work up to more advanced ass play or fisting, you’ll eventually have to start spending more money on higher-quality products. Here’s a rule of thumb: the bigger the toy, the more its quality matters. You’ll notice, for example, a difference in the quality of silicone between a small “premium silicone” butt plug on Amazon and a plug from SquarePeg. SquarePeg toys are generally much larger, much more expensive, and are intended for more advanced ass pigs.

Now let’s tackle your fear of becoming “too loose,” which is shared by virtually every gay man who’s brand new to bottoming.

Trust me on this: you want to loosen up. Anal sex will not be very enjoyable until you learn to relax your butt and wilfully loosen your hole. In good anal sex, you should get a little loose — that’s entirely the point. A dick is going inside you. The tighter you are, the more it will hurt.

Your anal sphincter is a muscle. It’s not just flappy skin. When you loosen up for anal sex, it doesn’t stay loose indefinitely after you’re finished fucking. It will tighten back up literally within seconds after sex and you’ll be back to as you were before. Now, as you have more and more anal sex and get better at it, you may notice that you can loosen up more easily and quickly, but that doesn’t mean you’re loose all the time. It just means you’ve trained your body to willfully open up when the time comes — you’ve gotten better at sex by learning to do something that makes sex better and more enjoyable.

Now, for fisters and extreme ass pigs, the situation is a little different. For fisters,  the goal for most of us is to have holes that stay noticeably looser all the time. But even the holes of guys who get punch-fisted several a week are still tight enough to function normally — they’re not incontinent or injured (although injuries can and do happen — fisting is an extreme sex sport). Even after an intense fisting session, your hole closes up again — although, depending on the intensity of the session, it might not tighten as quickly as if you were just having regular anal sex.

Some extreme ass pigs work up to toys that are so large that they do reach a point where they claim to be incontinent — and do so willingly, and incontinence is part of their fetish. That’s fine, that’s their thing. But most fisters, in my experience, are not looking to get that sloppy — and most of us never come close to being that way. You can be a lifetime fist pig and still have a hole that closes back up and functions normally within minutes after an intense fisting session.

And here’s something I want to shout from the rooftops: SKILLED TOPS DON’T LIKE VERY TIGHT HOLES. Sorry, but it’s true.

I’ve had countless guys turn me down on Grindr and Scruff because they see I’m into fisting and assume my ass is “too loose.” This tells me they’re either unskilled at sex or simply inexperienced. Really tight holes actually hurt your dick. Remember when I said the anal sphincter is a muscle? It is one of the strongest muscles in the body — and its default mode is to squeeze tight, meaning whatever’s inside will get vice-gripped, even bruised. If you’re a fun, adventurous top who wants to try different positions, vary your speed and intensity, and really make your bottom feel good, you can’t do any of this with a very tight hole.

The widespread cultural phobia of “loose” orifices is a result of slut-shaming. For centuries, we’ve called harlots and sexually-active women “loose women.” Having lots of sex will give you the ability to loosen up more easily, and since our culture shames sex, we also shame the physical evidence of sexual prowess. Contributing to this problem, gay men tend to make stupid jokes about loose holes around each other. We’ve all heard the quip: “He’s like throwing a hotdog down a hallway”. It wasn’t a funny or creative line ten years ago and still isn’t.

I have been to hardcore sex parties and seen ass gods in action. When I see a man’s gaping hole, I respect him as a pro — someone who’s rejected shame and trained his body to enjoy intense, beautiful sex. At that point, his anal muscle can open and close at will — he can loosen his ass or tighten it around a dick (or toy, or hand) as he pleases. And that’s when things get really fun.

You won’t get “too loose.” You’ll just get better at sex.

Love, Beastly 

7 Comments

  1. I am pretty new to anal toys specifically dildos. I have been disappointed by it because I can’t come by anal play along. I thought it was possible but maybe it is not. Also, I tend to fart afterwards.

    Like

    1. It is possible you may just have to change up the angle of your pelvis or you may need to relax more. Good luck lol

      Like

  2. I have a story to share: I hooked up with a sweet guy late one night. He was not kinky (I am) and so we agreed to have vanilla sex (he made a point of not being into anything rough). We met, and immediately spent quite some time kissing (he was a very good kisser!), then moved on to mutual oral sex. While playing with him, I noticed that he was very tight, so I spent a fairly long time rimming him, to help him relax. He then wanted me to fuck him, so I did.

    I can honestly say that he was the tightest guy I’ve ever had sex with. I took things slowly and gently, but he was clearly in some discomfort. Nevertheless, he knew exactly what he was doing, so had obviously been fucked before. When I mentioned to him that he was very tight, something in his manner gave me the impression that he was actually proud of being as tight as he was. We tried again, but I could see that he wasn’t comfortable, and because of what he had said about not wanting rough sex, I suddenly became terrified of hurting him, and so I lost my hard-on, and we called it a night.

    Alex is right — you don’t get too loose; only better at sex.

    Like

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