A Guide to Buying Your First Jockstrap


As a man who is into stylish undergarments, you’ve probably noticed that jockstraps have been trending recently. Originating as protective pieces for bicycle jockeys in the 19th century, jockstraps have a long history in the gay underwear and fetish scene.

It has only been in the last few years; however, that jockstrap creators have turned to exciting designs and materials to boost the sexiness of this once all-white sports jockstrap.

Whether you are new to the gay men’s underwear scene or you haven’t had the opportunity to purchase a jockstrap of your own, buying your first jockstrap is exciting and overwhelming. Use this helpful guide to buying your first jockstrap to find the perfect garment for you.

Where to Find Jockstraps
To buy your first jockstrap, you have to know where to look. Major supercenters or sporting stores typically carry jockstraps in the athletics section, but these options are more sporty than flirty.

If you are into plain functional white jockstraps with protective cups for sports, you might consider sporting stores. However, if you are looking to buy a jockstrap to spice up your bedroom or give you a confidence boost when out on the town, Timoteo has the perfect selection on offer.

You can browse the wide selection of fashionable and fun men’s jockstraps online, choose whichever style you like, and have it delivered to your front door.

Online jockstrap shopping is not only fast and convenient, but it also provides you with anonymity. If you like to indulge privately, buying a jockstrap online is the right choice.



How to Find the Right Jockstrap
To find the right jockstrap for you, consider the following elements as you browse your options.

Style and design
The style and design of your first jockstrap matter. It is important to find a piece that looks great on your front and back and highlights the size of your package. It is equally important that your jockstrap fits into your personal style.

When browsing an online jockstrap collection, take note of any colors or patterns that catch your eye. If you prefer a jockstrap sport theme, opt for a sporty mesh jockstrap or a football-inspired jockstrap. A floral-patterned jockstrap offers a softer look, perfect for a non-conventional version. If you are looking for a jockstrap for fetish play, opt for a zipper-pouch jockstrap in a bold pattern.

When buying your first jockstrap, make sure to find the right waist sizing. The last thing you want is a loose, droopy jockstrap, or one that is uncomfortably tight. To ensure you buy in the right size range, use a tape measure on your waist to gain an accurate measurement.

To measure your waist, place a tape measure at the top of your hip bone and bring it around your body, across your belly button, or just underneath. Note where the end of the tape measure sits and write down the number of inches. This is your waist circumference and the number you should look for on sizing charts.

The sizing chart for Timoteo’s underwear and clothing selection set the following guidelines:

  • 26” to 28” - Extra Small
  • 28” to 30” - Small
  • 31” to 32” - Medium
  • 33” to 34” - Large
  • 35” to 36” - Extra Large

When buying your first jockstrap, consider why you want one and what you plan to use it for. Will your jockstrap factor into your sexual adventures, or are you more interested in a jockstrap for the comfort and extra support it provides versus regular underwear? The answer helps you decide on the jockstrap that will work for you.

For comfortable, everyday wear, opt for a cotton tight-end jockstrap that cocoons your bulge, providing gentle support. For extra lift and support for your ass, grab a faux leather jockstrap with elastic leg straps. Opt for a fetish jockstrap made of neoprene, rayon, or spandex for easy cleanup after physical activities. The Avon Jockstrap is great for swimming or other wet play as it is made of 97% polyester and 3% spandex.

The fit of your first jockstrap is an important factor to consider when making a purchasing decision. Fit refers to how the jockstrap holds your junk and how it wraps around your backside. Some jockstraps fit tightly, others lift your package, and some models gently cup it, allowing it to sit comfortably within the pouch.

The Tight-End Swimmer Jockstrap offers a relaxed fit, allowing your member to sit freely within the pouch. The Atlas Jockstrap hugs your package a little tighter, giving it an at-attention look. As far as ass support goes, the Kick-Off Lace-Up Jockstrap provides serious plumping support to your cheeks while cupping your footballs in a tempting untieable pouch.

If you aren’t sure what fit you prefer, buy a few different jockstraps to try. You may discover that a certain fit works best depending on the day or activity.

When choosing your first jockstrap, pay attention to the materials the jockstrap is made from. Different materials serve various purposes and act differently when they come into contact with your member. You want to look at the pouch type on the jockstrap and the materials that make up the waistband and leg straps.

Cotton is a breathable material that helps to keep your skin dry and provides ultimate comfort. Opt for a mostly cotton blend if you are sensitive to PU leather, spandex, or neoprene.

Neoprene is a wearable type of rubber, which makes it excellent for sexy, flirty jockstraps. It is versatile and cleans easily, and it fits snugly while still feeling comfortable on your junk. Spandex and polyester are also good choices, as they are long-lasting and do well when they come into contact with fluids.

As for leg straps, brushed elastic provides sturdy, comfortable support. Brushed elastic is extremely durable and holds its shape when stretched, making it great for fun bedroom play. It is also gentle on the skin, only gripping as hard as it needs to.

How to Wear Your Jockstrap

When you buy your first jockstrap, you may wonder how and where to wear it. There are no hard and fast rules about how to wear a jockstrap, especially with the garment’s recent rise in popularity.

Some men wear their jockstrap as an outer layer, above a pair of long briefs. This provides the feel of the jockstrap without it resting directly on your skin. However, wearing a pair of underwear with your jockstrap may detract from the sexy factor.

Wear your jockstrap as underwear underneath your jeans, pants, shorts, or sweats for best results. This gives you the full benefit of feeling the hug of the leg straps and the pouch cupping as you walk. It also makes for a fun surprise for the special man who gets to see you without your pants on.

If you are bold and daring, wear your jockstrap to the beach. A water-friendly jockstrap makes quite the splash as you stroll along the beach, strutting your stuff. Just make sure the location allows for bare backsides before you venture out with your bare cheeks.

Find the Perfect Jockstrap
When looking for your first jockstrap, choose an online retailer that understands men’s underwear. Timoteo specializes in fetish wear, underwear, and swimwear for gay men. They boast a wide selection of bold jockstrap designs, fits, and materials that will make for a great first-time experience with a jockstrap.

Check out Timoteo’s premier jockstrap collection, featuring pieces from Cellblock13 and Vaux, in addition to their own designs. While you are there, check out the men’s thongs, briefs, and shorts to add to your sexy collection.

Back to blog