9 Key Tips for Trying a Strap-On for the First Time

Submitted by OliviaD on Thu, 10/23/2025 - 04:02

Let’s be honest the idea of using a strap-on for the first time can feel both thrilling and intimidating. Whether you’re the one wearing it or the one being penetrated, there’s a lot of curiosity, a bit of anxiety, and plenty of potential for pleasure. This guide isn’t just about technique it’s about connection, comfort, and discovering what feels right for you and your partner.

1. Feeling Nervous? Totally Normal.

Before anything physical happens, take a deep breath. Feeling nervous or even awkward is completely okay it’s a sign that you care about the experience. Most people assume they need to “know what they’re doing” the first time, but in reality, it’s a learning curve for everyone.

Talk openly with your partner about your curiosity, fears, and expectations. Laugh about it if you need to laughter breaks the tension and reminds you both that this is supposed to be fun, not a performance. The best approach is to stay curious, go slow, and let the experience unfold naturally.

2. Choosing the Right Toy for the Job

The strap-on itself is just a tool what really matters is how it feels for both of you. If you’re new to penetration play, start small. A shorter, slimmer dildo made of soft silicone can make all the difference.

Think about what sensation your partner enjoys: a curved shape might stimulate internal pleasure zones, while a smoother or straight design gives more control. There are also different materials silicone, rubber, even glass and each one feels unique.

And remember: size doesn’t equal skill. You can always upgrade later once you both know what works best.

3. The Harness: Comfort Is Everything

Your harness is the foundation of the whole experience. If it doesn’t fit well, everything else becomes more complicated. Adjustable straps are key you want it snug, but not so tight it cuts off movement or circulation.

There are several types:

  • Strap-style harnesses with adjustable buckles for a custom fit.

  • Panty or jock-strap harnesses that feel more like underwear.

  • Thigh or chest harnesses for creative positions.

If you want to keep things even simpler, strapless strap-ons can be fun to experiment with. They have a bulb or insertable end that goes inside the wearer, allowing both partners to feel stimulation simultaneously.

Pro tip: practice putting it on before sex. It’s not the moment to struggle with buckles while your partner waits on the bed.

4. Get Familiar Before the Big Night

Once you’ve chosen your toy and harness, spend some time wearing it privately. Walk around, adjust the straps, get used to its weight and movement. This might sound silly, but it helps you feel more confident when things get intimate.

Some people even practice gentle thrusting motions in front of a mirror (yes, seriously). This isn’t about performing it’s about becoming comfortable and natural in your body while wearing something new.

5. Let Go of Perfection

The first time using a strap-on might not look like a movie scene and that’s totally fine. Things might feel awkward, bodies might not line up right, and you might stop to laugh or adjust. All of that is part of the journey.

Instead of aiming for flawless rhythm or perfect penetration, focus on feedback. Ask what feels good, what doesn’t, and adjust as you go. Sex isn’t a checklist; it’s an exploration.

The more relaxed and connected you are, the better it feels for both of you.

6. Communication Is Sexy

Nothing ruins a new experience faster than silence. Communication verbal and nonverbal is the real foundation of great sex.

If you’re the one wearing the strap-on, ask questions like:

  • “Does that pressure feel good?”

  • “Want me to go deeper or stay shallow?”

  • “How’s the angle?”

And if you’re on the receiving end, speak up. Don’t assume your partner can read your body language perfectly. Even soft moans, words of encouragement, or gentle direction help build trust and excitement.

Also, emotional check-ins matter just as much as physical ones. For some people, wearing or receiving a strap-on can stir unexpected feelings about power, vulnerability, or gender expression. Make space for those conversations.

7. Lube Is Your Best Friend

No exceptions here use lots of lubricant. Even if you think you’ve used enough, add a little more. A well-lubed toy makes everything smoother, safer, and infinitely more pleasurable.

Water-based lube works great with silicone toys, but if you want a longer-lasting glide, consider a hybrid (water + silicone) formula. Just make sure it’s compatible with your toy material.

Apply lube to both the dildo and the entrance of the body. Reapply whenever things start to feel dry or too warm. Trust us lube is never optional.

8. Expand the Idea of “Strap-On Sex”

Strap-on play doesn’t have to mean traditional penetration. You can grind, tease, simulate the motion without full insertion, or mix it with oral or manual play.

Sometimes, just the act of wearing it the visual, the role reversal, the sense of empowerment can be incredibly erotic. You can also explore positions that suit your comfort level: missionary, doggy style, spooning, or even standing if you’re adventurous.

The key is to experiment until you find what feels natural and exciting. There’s no single “right” way to do it.

9. Aftercare and Reflection

Once everything’s done, don’t just roll over and call it a night. Aftercare matters it’s the part that turns a good experience into a great one.

Cuddle, talk, laugh, or share what you enjoyed most. Ask your partner how they felt, both physically and emotionally. Maybe you’ll discover new fantasies or preferences to explore next time.

And if something felt off or uncomfortable, talk about that too without blame. Every experience teaches you more about what you like and how to connect better.

Lastly, clean your toys properly with warm water and mild soap (or a toy cleaner). Store them safely and dry for next time.

Trying a strap-on for the first time isn’t just about penetration it’s about curiosity, trust, and the freedom to explore pleasure in new ways. There’s no need to rush or impress anyone. The best experiences come when both people feel seen, safe, and excited to discover together.

So loosen up the straps, grab some lube, and remember: great sex is less about what you do and more about how you feel doing it.