Confessions of a Virgin Hunter

Why sexually inexperienced partners can be more fun than you know

Tess Dagger
Published in
8 min readSep 8, 2020


Photo: Jason Leung

I’ll admit it, I’m a sucker for a nervous newbie. It’s been a penchant of mine since forever. There’s something incredibly hot and powerful about being the one steering the sex bus, y’know?

If I have my eye on someone and I find out that well into their late twenties or thirties that they’ve had only 2, 1, maybe 0 partners, it can rev my engine quite a bit. Maybe I can explain why.

Do you remember your school crushes? Think about when the two of you learned nervously to cuddle (and then couldn’t get enough of it), or how they would hesitantly trace a finger along your skin, probably somewhere benign like your arm, and it would set your whole body alight.

All that newness and lead up was setting us up to have our minds completely blown once we finally had sex. And then…they weren’t. And who could blame us? Who of us actually knew how to fuck when we were just learning to fuck?

No wonder people don’t seek to relive that experience. Heck, we actively avoid it. We can read first-hand experiences that pepper the internet, women who tell their stories of the “surprise virgin” who never let them know beforehand, or the post-virginity-taking guilt that it likely wasn’t as special for them as it was for him. The men’s interviews can be even worse.

‘“They take extra prep!” “The sex won’t be good!” “Be prepared for a freak-out!”


So let’s stop right there and ask the big question.

How are people taking each others’ virginities? Because that’s the question that really seems to matter. Sex is as good as we make it — sloppy, drunk, weird, intimate, special, wild, primal, hot, awkward. All of it.

So if you’ve got the experience, why would a partner’s inexperience make it worse?

Spoiler alert: It doesn’t.

That highschool flirting isn’t just for high school.

The light touches, the fingers brushing each other as you walk alongside each other, the beginnings of a cuddle, the nervous first time sharing a bed…these things can be as exhilarating now as they were when you were younger and probably are for the newbie next to you.

When we build up experience with flirtation, we learn to read subtle cues in people that expedite the process for us. Sadly, a lot of those slower and more drawn-out forms of tension-building get lost along the way. As adults, we generally know what we want and how to go about getting it. After all, we’ve had many successes and probably a few failures under our belt.

But not for them. Exploring the body may still be a new and blooming experience for them, depending on what they’ve tried already. And slowing down to another person’s pace can help you appreciate the experience you have while rediscovering the sexy build-up of approaching sex with fresh eyes. Enjoy it!

The build-up is hot, the communication is hotter.

I’ve had bad sex. I’ll spill that particular set of beans right here and now. Hell, I’ve been the bad one at having sex before, probably many times, and it won’t be the last time either. These days I’m pretty confident in what I can bring to the bedroom, but I know where my inexperience is. When I find it, I’m full of questions for my partner.

I think one of the biggest issues with sleeping with first, second, and third timers is that they don’t have practice in asking questions. More importantly, they don’t have practice asking questions during sex. Spontaneity and wild flinging of clothes seems to be the most mainstream portrayal of dirty dancing we see today, and it crowds out the idea that we can slow down and ask questions beforehand, up until and well into the deed itself.

So how do we change that? Ask the questions ourselves! Take the initiative to show them communication is sexy and can be part of foreplay. Be a safe space to seek answers without judgment. If that yummy sexual tension has been building up over time, you can use that opportunity to start a dialogue. You may think it’ll break at the first question, but it won’t — if anything, curiosity will just build over time.

Yeah, but what if it’s a spontaneous hook-up?

Let’s remind ourselves that there’s a way to keep communication seductive and spontaneous all at once, and that’s showing what to do. It’s a piece of advice that’s been in sex columns since the dawn of time. Guiding their hands in the ways you want to be touched and giving sultry, positive verbal cues when they do the right stuff has always been the trick to getting what you want, even out of somebody who feels more lost than the Pope at a bondage club. But I want to add a key piece to that.

Slow. The fuck. Down.

When we slow way, way down, the opportunity to show what you want isn’t a frenzied motion that can get lost between the sheets. It’s a deliberate and awesome power-move that will be cemented in their brain forever.

Our brains automatically like to assume that fast fucking is less emotionally intense and slow sex is the equivalent of making love. If making love is not what you’re after, you may default towards speeding things up a bit. The faster the bang, the fewer emotions, right? Wrong! Slow sex can increase intimacy, sure, but it can also be as primal and raw as we want it to be. You don’t have to fall in love. You just get to feel good.

Gamify the (in)experience

Before my husband and I ever fucked, we played “blindfold”. I’d blindfold him and tell him to touch my entire body, memorize it with his hands, and tell me what he felt. I gave him prompts, like “manhandle me” or “be gentle and sensual”, and he’d fulfill them eagerly. If I were blindfolded, he’d have to learn to give the prompts and communicate, but I made sure he was well rewarded for it. The tension drove us crazy and we would be turned on for weeks afterward.

I traveled a lot for work at the time, and we’d have plenty of phone sex as well. The act of describing what we were doing and what we’d do to each other made it much easier to visualize and, in the end, enact upon each other.

Another example is having my mind blown by a girlfriend before we had ever slept together. She had given me small clues for weeks, through how we lay together cuddling (and the importance of hip positions) or what she’d do to my earlobes and fingertips with her tongue (which showed how she wanted to be gone down on). I’d mimic these clues she was giving me, not realizing what she was driving at until the night we finally did the act. Then, click! She had given me an entire toolbox of skills to use on her exactly the way she wanted. It wound up being an incredible first time.

There are so many things peripheral to sex that we can engage in that will lead to better sex, but most people seem to believe this kind of foreplay is reserved for the sexually experienced to explore after they get their laurels.

Nope! It’s for everyone! And the teasing will be one more thing that builds skills that can be used directly during sex itself.

Ditch the One-Pump-Chump mentality

This is a particularly linear piece of advice, but for women who sleep with men, I can’t drive this point home enough. I’ve heard lots of women complain that the hookup was a dud because he barely lasted at all.

There’s a flipside to this. The complaint that sometimes the sex lasts too long also gets bandied about a lot — guys, 20 minutes of actual penetration can be plenty for most women. There are loads of other things you can do to get juices flowing. Given the choice between the locomotor and the gone-in-60-seconds, I’ll take the latter.

Why? Well, my ego, for one. There’s something that tickles me about the fact that he was so turned on that he could barely contain himself. I must’ve done something right. And why not go again? If you’re really unsatisfied, chances are he will be ready for round two in not too long, and thus the quick finish warrants no dissatisfaction.

I had a partner once who would always cum within two minutes of starting, without fail. But all that meant was a quick pee break and we’d be at it again, and he could always last longer the second time. Give them a chance, and they’ll likely rise (hehe) to it.

Gamification of inexperience is a big plus here too. How could you play up helping him last? The challenge can be a fun way to explore each others’ limits, with you leading the way.

And that brings me to my last point…

Embrace your inner Dom(me)

When you know your experience in bed can satisfy a partner, there’s a power in that which will carry over to your bedroom experiences. So when you’re with somebody who doesn’t know what they’re doing, consider holding the reins unless they truly want them.

A hint — I’ve never met a virgin or near-virgin who wanted to be in the driver’s seat.

This works for spontaneous sex as well as partners you’ve been building up to. Regardless of who you’re about to get horizontal with (or how), it’s always going to be better if you’re confident. Confidence in our sexual prowess can lead to us trying things that we may never have tried before, and being turned on by the sexiest thing in your room — yourself! You’re creating a hot scenario for both of you and have the ability and seduction for two. If that’s not a boost in the pants, I don’t know what is.

Know who else feeds off of that confidence? Your partner. Instead of fearing their own performance, they’ll be willing to put trust in you and relax into the sensation rather than tense up, which is better for everyone. Reassuring them that you’ll ensure your own pleasure means that they can drink it all in while giving you what you asked for.

Who knows? Over time, what you ask for may become their specialty!

So now you know my dirty little secret, and more importantly, you know why. Do I meet many virgins (or near-virgins) at my age? Not really, no. And the more people fuck, the more they tend to stick with what they like, which means that there’s always a chance that my would-be partners and I just won’t find the same things enjoyable. In those moments I can appreciate the inexperience of other lovers who let me influence their first steps into their sexual journey.

There is a chance that being that person will never appeal to you, and to that, I say well done for knowing what you like. But who knows, you may still find yourself sharing pillows with somebody who has no clue what they’re doing. And in those moments it helps to remember that it’s anything but a deal-breaker.



Tess Dagger

BDSM enthusiast and former sex worker, here to write it all down.