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What Would’ve Made Your First Time With A Woman Better?

24. Apr 2025
first time lesbian sex stories

What do you wish your lesbian sex for the first time had been like?

The answers of lesbian sex for the first time​ hit like soft waves—sometimes gentle, sometimes gutting. But what stayed with me was the quiet theme underneath: most people didn’t want fireworks. They wanted to feel seen.

My own first time? It wasn’t perfect. We were both nervous. She was scared I wouldn’t enjoy myself, and I was scared I’d accidentally mess everything up. She apologized three times before even touching me. I kept telling her, “I want this because it’s with you.”

So we talked. We giggled. We paused and regrouped. And eventually, we found each other—slowly, gently.

And, How to have lesbian sex first time?

Let’s be real—there’s no “right way” to have lesbian sex.

There’s no script, no play-by-play you have to follow. But if you’re reading this, chances are you (or someone you love) is gearing up for that big, beautiful, nerve-wracking first time with another woman—and you want to do it right. Not perfect. Not porn-y. Just... right.

You care.

You care about how it will feel—for you and for her. You care about doing it slowly, kindly, and in a way that builds trust, not pressure. So here’s a real-talk, soft-hearted guide for making that first time tender, safe, and unforgettable.


1. Drop the pressure to perform. This isn’t a movie.

Forget anything you’ve seen in porn or read in steamy fanfics. The first time doesn’t need to be wild or athletic or involve five different positions and a toy haul.

What matters most? Eye Contact. Connection. Consent. Care.
If all you do is cuddle, kiss, touch gently, and whisper “Is this okay?” while exploring each other’s bodies, that’s already more erotic than most people will experience in a lifetime.

2. Talk. Not just before, but during. And after.

Many people said their first time would’ve been way better if they just… talked more. You don’t need a whole sex TED Talk. Just ask like this:

“How are you feeling?”
“Do you want to try this?”
“You can stop me anytime, okay?”
“Does this feel good, or should I switch it up?”

Being nervous doesn’t make you bad at sex. It makes you human. Communication is sexy. And it helps build the emotional safety that makes physical pleasure even deeper.

3. Go slow. Then slower. Then even slower.

There’s no finish line. Take your time kissing. Take your time undressing. Take your time touching. Many people don’t realize how arousing it is to be seen and wanted without being rushed.

Ask her how she likes to be touched. Tell her what you like too. This is your time to be curious, generous, and present—not performative.

4. Toys are optional. Comfort is essential.

You don’t need a drawer full of lesbian sex toys,  and one of beginner sex toys like strap on vibrator and strap on harness are amzing. Fingers, mouths, grinding, kissing, mutual masturbation—these are all beautiful, valid ways to have lesbian sex.

The key is comfy. Emotionally and physically. If she’s nervous, let her take the lead—or hold her hand while you both figure it out together. Normalize laughter. Welcome awkwardness.

You’re not trying to impress. You’re trying to connect.

5. Validate her. And yourself.

This one’s big: Make her feel wanted. Especially if she’s scared.

Say things like:

“You’re turning me on just by being close.”
“You don’t have to do anything to impress me.”
“This is already so good.”

That emotional safety is the ultimate aphrodisiac. And remember to affirm yourself too—you’re learning, and that’s something to be proud of.

6. Aftercare is real.

After it’s over (whatever it ends up being), stay close. Snuggle. Talk. Check in emotionally, not just physically.

Ask things like:

“How are you feeling?”
“Was there anything you loved?”
“Anything you want different next time?”

Being held after sex—emotionally and physically—is often what makes it feel meaningful, memorable, and safe to do again.

It’s Not About “Doing It Right.” It’s About Being Right Here.
Your first time doesn’t need to be explosive. It needs to be honest.

Let it be slow. Let it be soft. Let it be sweet. Let it be sweaty or shy or silly. Let it be exactly what it is—a beginning. A space you both co-create. And if that space is full of care, consent, and curiosity?

Then you’ve already done it right.

Bonus: Ready When You Are – Beginner-Friendly Lesbian Sex Toys for More

When you’re ready to take things a little further—or simply want to explore new ways to give and receive pleasure—lesbian sex toys can be a beautiful extension of intimacy. Think of them as tools for confidence, connection, and curiosity. Not a replacement for feeling, but an enhancement of it.

At Crassie, we’ve designed a couple of beginner strap on kits options with queer first-timers in mind:

Velvet Touch Dual Density Dildo

This isn’t your average silicone toy. Our dual density dildo with platinum silicone material, design the soft outer layer and firm core, and comes in sizes that feel just right for those new to penetration. Gentle, flexible, and just the right amount of “wow.”

And You’re doing this strap-on play for her, with her.

Build the heat first—this is about mutual pleasure, not rushing to the main event.

If she’s on all fours, doggie-style, anchor one hand gently on her hip while your other hand stays on her clit—giving her something to grind into. Keep checking in, keep reading her body.

If she’s lying on her back, face to face with you, fold her knees toward her chest and hold her thighs. This position is intimate and visually intense—you get to watch every moment your strap slides in and out of her, and the look on her face as it hits just right.

Lean into the rhythm. Have fun. Stay present. Let her know you’re there for every moan, every breath, every yes.

Strap On Vibrator with Dildo Harness

If you’re curious about strap on play but totally new to the harness world, we got you.

This beginner strap on kit comes with:

A super comfy jock harness that’s easy to adjust and fits most body types.

A vibrating dildo that’s soft, smooth, and oh so beginner-friendly.

Lesbian Sex Toys don’t replace intimacy. They invite more of it.
If you’re curious, ready, and supported, your first time (and every time after) can be full of discovery, laughter, and lots of moaning-in-a-good-way.

Explore more in our Beginner Toy Collection – made by queer, for queer.

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