Curious about your first time with a woman? Nervous, excited, unsure what it might feel like or how to even begin? You're not alone. This one's for you.
All the talk about emotional readiness, mutual respect, and making the first move softly.
By Lisa Opel
Soft Starts Are Still Powerful
Let’s talk about first times. Not the polished, movie-perfect scenes with swelling music and perfectly tousled hair. But the real ones: the fluttering nerves, the unsure glances, the thrill of proximity, and that quiet voice inside whispering what if?
Whether you’re meeting someone new or exploring connection at a Skirt Club event, there’s something tender and mesmerising about those first gentle steps into intimacy.
I remember mine. We spent nearly six months orbiting each other; long conversations, flirty texts, catching each other’s eyes at Skirt Club events. The energy was there, always. Playful. Lingering. But unspoken.
What held me back? Only me.
When I finally gathered the courage to say, “I’d really like to kiss you,” something shifted. She smiled and said, “I was wondering when you’d say that.” And when we finally kissed, it was electric. Not because I knew what I was doing. But because I let myself want it.
“Intimacy is the capacity to be rather weird with someone; and finding that that's OK with them.”
Alain de Botton
Desire doesn’t have to be loud. Sometimes it tiptoes in and changes everything.
Building Confidence to Approach Her (Even When You’re Nervous)
Approaching someone, especially another woman, can feel wildly exhilarating… or downright terrifying. You might worry about reading signals wrong, about rejection, or just not knowing what to say. Trust me, I’ve been there.
But here’s the truth: Confidence doesn’t always look like bold swagger. Often, it’s a soft breath before you walk across the room. It’s choosing to smile even when your heart’s racing. It’s saying “hi” with trembling hands.
Start small:
- Make eye contact and hold it a little longer.
- Compliment something specific and genuine; her laugh, her earrings, her energy.
- Ask her if she’s been to Skirt Club before. A shared space gives you an easy in.
- Or simply say, “I’ve been wanting to talk to you, but wasn’t sure how to start.”
No pickup line, just presence.
Approaching someone isn’t about impressing them, it’s about inviting them in. And the more honest that invitation, the more likely she is to feel safe, seen, and curious to connect back.
What If It’s Your First Time at a Party?
This is a question that comes up often. What if the first time happens at a party? What if people are watching?
At Skirt Club, our parties are created to feel empowering, not performative. That means your experience, whether bold or bashful, is yours alone to shape.
The truth? You’re allowed to wait. To observe. To take your time.
But sometimes, waiting becomes overthinking; and overthinking can talk us out of what we really want. I’ve been there. Stuck in my head, replaying every smile, wondering if the moment was right… and missing it.
Sometimes, we just need to feel more and think less. Tune into your gut. Let your body lead the way. And then, when you’re ready, use your words. A simple, “I’d really like to kiss you. Would that be okay?” can open up a whole new world.
You don’t have to perform. You don’t have to impress. You just have to be honest.
And that? That’s magnetic.
How to Flirt Without Overwhelm
Flirting isn’t about slick lines, it’s about presence. A shared laugh. A lingering look. Fingers brushing hers when offering a drink. That subtle interplay is where real connection begins.
Many women tell me, “I don’t know how to flirt with other women.” But guess what? You already are. Your curiosity and respect are halfway there.
As Capri Campeau, our favourite flirt expert and bisexual big sister, puts it:
Playful with tension plus intention.
That’s the sweet spot to aim for.
In our Embody Your True Body events, we invite experts like Capri to share tips and lived experiences that feel wholesome, sexy, and deeply helpful. Learning to lean into playful intent can be a game‑changer.
Try this:
- Compliment her genuinely: “You have a really beautiful energy.”
- Lean in and ask: “May I kiss you? Where may I kiss you”, It’s honest and bold in the best way.
- Let yourself be a bit awkward, it’s part of the charm, and perfection isn’t expected.
When You’re Both Inexperienced
There’s something beautifully mutual about two women exploring each other for the first time. There’s no pressure to perform. No one needs to know more. It becomes an exploration you take together; slow, excited, shared.
One woman at a Skirt Club Mini Skirt event once whispered to me, “I think she’s as nervous as I am. Is that… okay?” My answer? It’s more than okay. It’s a gift.
“It is not time or opportunity that is to determine intimacy... Seven years would be insufficient to make some people acquainted with each other, and seven days are more than enough for others.”
Jane Austen
No script: just tune into each other.
Confidence Isn’t Required, But Curiosity Is
I spent years wondering what it would be like to kiss a woman. I rehearsed conversations in my head. Googled “how to approach another woman.” Saved TikToks. Lost my nerve.
What helped? Hearing other women say, “Me too.”
Show up open, not polished. You’re not auditioning, you’re connecting.
“There’s something incredibly powerful about saying, ‘I don’t know what I’m doing, but I’d like to try.’”
Anonymous Skirt Club member
Reading Her Cues & Finding Your Courage
“My first time, I kept wondering if she was ready to kiss me or take things further. I was so nervous about coming on too strong…”
Sound familiar? That inner dialogue; "Does she like me? Is she into this? What if I misread the moment?" can get loud. But here’s the truth: it’s okay not to know everything. What matters most is how you stay open, respectful, and responsive.
Start by paying attention:
- Is she holding eye contact just a little longer?
- Is her body language open; shoulders relaxed, leaning toward you?
- Is she mirroring your energy, your smile, your laugh?
These are subtle signals that say: I’m enjoying this. I feel safe here.
Still unsure? Ask. That’s sexy. Try:
“I’m really enjoying this… can I tell you something?”
“I’d love to touch you. Would that feel good to you too?”
Being direct doesn’t kill the vibe, it creates trust. You’re not expected to read minds. You’re expected to care enough to ask.
And as for courage? It doesn’t arrive in a lightning bolt. It comes from tiny moments of honesty. From saying what you feel, even with a shake in your voice. That’s not weakness. That’s intimacy.
But What About the Sex Stuff?
So… what if things do heat up? What if you’re both ready and the moment’s right, but your mind starts spinning: What do I even do?!
First; breathe.
There’s no roadmap for intimacy between women, and that’s part of the thrill. But here are a few things that might help:
- Start with your senses. Kissing, touching, tasting. Let your curiosity lead, not your expectations.
- Mirror her energy. Watch how she moves, responds, sighs. Let her reactions guide your rhythm.
- Use your words. Ask softly: “Do you like this?”, “Want me to keep going?”, or “Can I try something?” this builds trust and connection.
- Let go of the goal. This isn’t about performance or “getting it right.” It’s about pleasure, closeness, and presence.
You might laugh. You might fumble. You might come closer than you ever have before. All of that is perfect.
First times with women can be sensual, awkward, tender, wild, or all of the above. Let them be yours.
About This Article
This guide was written for every woman who’s paused before the leap. For every inquisitive heart who’s thought, “But I’ve never done this before… will that matter?”
Your first time doesn’t have to be perfect. It doesn’t even have to go anywhere. But it deserves to feel safe, respected, and warm.
Whether you’re attending your first Skirt Club soirée or just dipping a toe into fantasy; you’re allowed to go slow. You’re allowed to be unsure. And you’re still valid.
Educational Insight: What Makes a “First Time” Special
There is no one-size-fits-all moment that defines intimacy with another woman. For some, it begins in a long conversation over drinks. For others, it’s a shy kiss or an accidental touch that lingers.
Bi and queer women often feel they must “prove” something; have the experience, the receipts, the clarity. But sexuality is fluid, and readiness isn’t about performance.
“Expectations are everywhere, especially when it comes to intimacy. The real magic lies in being fully present with each other.”
Esther Perel
The most important ingredient for the first time? Mutual consent and emotional readiness. Everything else is delicious detail.
Ready to Explore? Start Here.
Whether you're just taking a peak into your desires or ready to leap into the unknown, we’ve got you. Try our Embody Your True Body online course from the comfort of home, meet like-minded women at a social soirée, or take it to the next level at one of our iconic Signature Parties.
Explore all upcoming events at skirtclub.co.uk/events
A Personal Note from Lisa
First times are rarely perfect, but they’re always powerful. Not because we know what we’re doing, but because we finally let ourselves feel what we want.
You don’t need experience to be valid. You don’t need confidence to be desirable. You just need permission; from yourself.
Wherever you are on your journey, I hope this piece offered comfort, courage, or even just a knowing nod. You're not alone. And you're allowed to want more.
About Lisa Opel
Lisa Opel is a bisexual author, TEDx speaker, and unapologetic pleasure advocate. She is the author of two provocative books - GIVE IT TO ME! and SEX SEX SEX: Your Complete Sexuality Workbook - both bold, beautifully written explorations of eroticism, intimacy, and identity.
Lisa also hosts the bilingual podcast DEEP&DIRTY, where she dives into the real stories and juicy questions around sexuality, sensuality, and self-discovery. Her TEDx talk - Rediscovering sex after a dry spell - tackled the modern complexities of love, lust, and reclaiming desire.
As a confidante to many women navigating their desires and identities, Lisa offers not just her services, her insights, a shoulder, but intimacy; creating spaces through her one-on-one sessions, workshops, writing, events, and live erotic readings where women feel seen, heard, and deliciously understood.
FAQs About Your First Time with a Woman
Q: What if I don’t know what I’m doing?
A: That’s not a problem; it’s a beautiful place to begin. First times aren’t about mastery, they’re about curiosity. Say something simple and honest like, “This is new for me, but I’d love to explore it with you.” Go slow, ask what she likes, and stay tuned into her body language. The sexiest thing you can bring is attentiveness.
Q: Can I be nervous and still sexy?
A: Absolutely. Nerves mean you care; and there’s nothing more attractive than authenticity. Let her know you’re a little shy; it builds trust and opens the door to softness. Try grounding yourself with breath, touch her gently, and let eye contact do the talking. Confidence grows when you give yourself permission to feel it all.
Q: What if we’re both inexperienced?
A: Then you’re on equal footing, which can be incredibly freeing. Start by saying, “I’m not quite sure what I’m doing, but I’m excited to learn together.” Share what feels good. Laugh. Ask questions like, “Do you like this?” or “Can I keep going?” Mutual exploration is the most honest kind of intimacy.
Q: Do I have to do something physical at a party?
A: No way. Skirt Club is a pressure-free zone. You’re welcome to come just to watch, sip cocktails, chat, or dance. You might say, “This is my first event and I’m just soaking it all in.” That honesty is magnetic; and you’ll likely find others doing the same.
Q: What’s the best way to show interest without being too much?
A: Start light and let her energy guide you. Compliment her in a way that feels sincere: “You have a really beautiful presence,” or “Your smile just caught me completely.” If the connection’s mutual, ask gently: “Would it be okay if I kissed you?” Consent is sexy; and confidence doesn’t have to be loud to be powerful.
Q: Do I need to talk about STIs and protection?
A: Yes; and it doesn’t have to kill the vibe. Open, respectful communication is part of what makes queer intimacy feel so safe and special. You might say, “I’d love for us to feel really comfortable; have you been tested recently?” or “I have these dental dams/finger gloves if we want to use them.” It’s not awkward; it’s grown, sexy, and smart.
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