How to Wear a Thong Comfortably: Step-by-Step Tips for a Perfect Fit

Every guy remembers his first thong. You pull it on, catch the view from behind in the mirror, feel quite pleased with yourself, and then spend the next hour wondering whether that strap is supposed to feel like that.

Mostly, it is. The rest comes down to how you put it on, and that's the bit nobody explains. Plenty of men give up on thongs after one bad fit or a rushed first outing, and the style takes the blame.

At Bill and Brandon, thongs are some of the boldest pieces we make, so here's the guide we wish someone had handed us. Below is how to wear a thong as a man, how to tell if it fits and how to make the first week a lot more comfortable.

HOW TO WEAR A THONG AS A MAN, STEP BY STEP

Putting one on takes about ten seconds once you know the order. Most of the discomfort first-timers complain about comes from rushing step two.

1. Step in and pull it up a touch higher than a brief

Put a leg either side of the back strap and pull the thong up to your waist. Go slightly higher than you would with a brief, then let it settle back down. That small extra lift gives the strap room to sit where it should instead of tugging on the front.

2. Settle your package into the pouch

Reach in and position everything forward and up so it's supported and centered. This is the step that makes or breaks comfort. A thong has no leg fabric holding things in place, so the pouch does all the work (and your "precious bits" will tell you fast if you skipped it).

3. Let the back strap lie flat

Run a finger down the back strap to check it isn't twisted or folded over. It should rest flat between your cheeks with no rolling at the top. A twisted strap is the most common reason for that "something is very wrong back there" feeling.

4. Check the waistband

The waistband should sit flat around your hips without rolling over or leaving a deep red line when you take it off. Ours use a super soft waistband for exactly this reason, because a stiff band is the first thing you notice after lunch.

5. Do the walk, sit and bend test

Before you head out, walk around the room, sit down and bend to tie your shoes. If nothing shifts or rides up, you're sorted. If something does, go back to step two before you blame the thong.

HOW TO WEAR A THONG CORRECTLY: THE FIT CHECKS

So should a thong be tight or loose? Snug enough that it stays put when you move, relaxed enough that you forget about it after a while. Knowing how to wear a thong correctly mostly comes down to finding that middle ground.

A few signs something isn't quite right:

• The back strap keeps creeping up or digging in, which usually means the waistband has slipped too low and is pulling the strap tight.
• You feel squashed rather than supported at the front, which points to everything being pushed down instead of forward into the pouch.
• The waistband rolls or leaves marks, which means it's sitting in the wrong spot on your hips.

Our thongs come in one size, cut from a soft, stretchy blend of 92% cotton and 8% spandex that gives enough to suit a wide range of builds. If you're not sure one will work for you, drop us a message before you order and we'll talk you through it.

One thing worth admitting: a thong takes a few days to feel normal. On the first morning you'll notice the strap. By the end of the week you mostly won't.

CHOOSING YOUR FIRST THONG

For a first pair, keep it simple. A plain color in a soft, breathable fabric is far easier to live with than anything sheer or ultra-minimal, and it tells you whether you actually like the style before you go bolder.

Our Thong in black is the one we'd hand any first-timer. It has a body-defining fit, that super soft waistband and a cotton-stretch fabric that breathes far better than the shiny synthetic pairs you find in novelty shops. Black goes under anything too, which matters more than you'd think on day one.

Once that first pair has earned its place in the drawer, the white and black thong set gives you a pair for each mood. Rotating between pairs also helps the elastic last longer, so you can thank us later.

A quick warning if you travel. In Australia, "thongs" are flip-flops, so asking a Sydney shop assistant for a black thong will get you pointed toward the beach sandals.

If your first thong is also your first step into bolder underwear generally, our guide to erotic underwear for men covers where to go next.

NOT SURE YET? START WITH A JOCKSTRAP

Some guys love the idea of a thong but get nervous about the strap. A jockstrap is the easiest halfway house. You keep the full front pouch and the open, show-off back, with two straps framing the bum instead of one sitting between the cheeks.

Bill's Jockstrap in white is a good place to start. It has a hang free pouch design, the same soft cotton-stretch fabric as our thongs and a body-defining fit. One tip from the product page: go one size up from your usual. Wear a jock for a week and the jump to a thong will feel much smaller. Our guide on how to wear a jockstrap goes into more detail.

WHAT TO WEAR OVER A THONG

For most men, the whole point of a thong is a clean line. With no fabric around the legs or across the bum, there's nothing to show through fitted trousers, tailored shorts or jeans that fit the way they should.

It works best under clothes that sit close to the body. Under baggy joggers you lose the benefit, and the thong has more room to shift around.

This is the reason Bill and Brandon makes mens sexy undies to be worn every day rather than saved for special occasions. A thong under a sharp pair of trousers is the perfect example. Nobody else knows it's there. You do, and that's half the fun.

HOW LONG DOES IT TAKE TO GET USED TO A THONG?

Usually a few days. The first time you wear one, you'll be very aware of the back strap. After a handful of wears it fades into the background, the same way a new watch stops feeling heavy on your wrist.

Ease in. Wear your first thong around the house for an hour or two, then on a short trip out, then for a full day. Save the long-haul flight and the twelve-hour workday for when you know the fit is right.

And if it still doesn't click after a couple of weeks? That's allowed. Thongs aren't every man's favorite cut, and plenty of guys find they prefer the security of a jock or a brief. Finding out costs you £20.99 and a little nerve.

IS IT HYGIENIC TO WEAR A THONG EVERY DAY?

Yes, with the same habits you'd use for any underwear. Change it daily, pick a breathable fabric like cotton and make sure you're fully dry after a shower before you put it on. If you wear one to the gym, swap into a fresh pair afterward.

Care is simple. Machine wash cold, skip the bleach and tumble dry on low heat to keep the elastic springy. A thong that has lost its stretch stops holding you properly, and that's when the riding up starts.

READY TO TRY YOUR FIRST THONG?

Wearing a thong comfortably comes down to a few habits. Pull it up a touch higher, settle everything into the pouch, keep the strap flat and give yourself a few days. Get those right and the thong goes from the scary pair at the back of the drawer to the one you reach for under your favorite jeans.

When you're ready, our range of men's thongs runs from plain black to bold reds, greens and oranges, all cut in the same soft cotton-stretch fabric.

We're a UK brand with daily dispatch, discreet eco-friendly packaging and more than 500 reviews from guys who came back for another pair. Have a browse of the full range, check the FAQs if you have a question or get in touch and we'll help you find your fit.