Aunt Vadge: why can’t I go deeper?

Hi Aunt Vadge,

I’m in my late 20’s and a virgin. I finger myself but I don’t go deep, well, actually I am not able to go deep. So half of my finger goes inside. I am comfortable with two fingers as well. Sometimes it’s pleasurable, but mostly not.

I want to have sex but I feel my vagina is too tight, and even if I do try, it gets painful and we stop (penetration with a penis). I am always very wet, whenever I finger myself. I have been fingering myself for a week now but I fail to understand how deep can I go, and how to gain confidence to take a step further.

I don’t really feel pain after fingering. I’m just very aroused. I have a very loving partner but I need direction. What am I doing wrong? And how long is the wait, do you think, before I can enjoy a sex life with my partner? I just need guidance as to how to do it. Do you think I can now try with a toy?

Thanks so much,


Hi Deeper,

Thanks for your email. Sounds like you are having a tough time getting into your vagina, which sometimes happens when you are first starting out.

The stage you are at with your sex life is a delicate one for pushing into the next phase, in this case being penetrative sex with either your partner, fingers or a sex toy.

You said you have only enjoyed fingering a couple of times, and the other times, you get to a certain point then you have to stop before it becomes uncomfortable. The vagina is a very stretchy part of your body, and when you are fully aroused, it tends to want to open up a bit more than usual. This, combined with your natural lubrication, would usually make penetration a successful and pleasurable event, but this takes some practice – nobody is good at it at first.

The things that can interrupt this process are numerous, though you have already ticked off a couple: being sexually aroused is critical, which means being turned on by the partner you are with. (It is unexpectedly common for women to have sex with men they don’t really like/aren’t attracted to, and then be genuinely curious as to why their body won’t perform.) Let’s assume both those elements are covered.

Because you are a virgin, the feeling of something being right up inside of you is unfamiliar and can feel quite unusual – that’s because sex is weird, gross and unusual – and also fun, hot and special. Your hymen will be long gone if you can put two fingers in up to the second knuckle – your hymen is quite close to the vaginal opening, though it’s possible part of it remains – check the diagrams.

What to do and how to do it

You don’t mention if you are able to use tampons or if a doctor has ever examined your cervix or vagina with a speculum – the stainless steel tool that holds the vagina open so the physician can shine a torch into the vagina and check it or take swabs during a pap test. If you have been examined and can use tampons, you could indeed push on and very slowly and gently try using a sex toy. Try different angles, and be slow and gentle. You will feel when it hits your cervix.

It shouldn’t hurt though it is possible that it might feel a little uncomfortable at first – when the vaginal tissues are aroused, they swell up with blood and create a sort of cushion, but up until that point, when you are not sure what to expect, it can feel just like you have something shoved up your vagina (which you do!). This aroused blood-swelling protects against pain and damage. What this means is that prior to trying to insert the toy, play with your partner and get very turned on – make out, try oral sex, touching, and stimulate your clitoris in a way that you find extremely enjoyable. I would advise against using the vibrator function on any toy just yet, as this can really interrupt the true sensation.

The clitoris is the key to your sexual satisfaction, so make a point to focus on it. Be gentle, discover what you like, and then when you are hot and wet, slowly insert a small toy. You need something like the Lady Finger, which is thin and long. Start off with smaller objects and graduate when you feel able. This process might take days, weeks or months – everyone is different so take your time and find out what your vagina likes.

When it comes to your partner’s penis, the weight of a man behind a penis can make a penis more full-on than a toy you can control, meaning your partner’s penis – though warm and hard and delicious – may be part of your graduation, not the first step. Go slow! Try to find your g-spot together. Get your boyfriend sucking your nipples or licking your ears or clitoris or if you’re game, your anus, while penetrating your vagina with a toy or finger. Just sticking something in your vagina and hoping it feels good doesn’t work, so keep the clitoris stimulated at the same time as penetration occurs – it’s key.

Also spend time pleasuring your partner, as giving him pleasure will help you to become aroused without it being so focused on your vagina being open or closed – it can get pretty single-minded when there is an obstacle to what you think should be happening, and so removing the focus and indirectly becoming turned on by touching him is useful. Find pleasure in giving pleasure. If you aren’t sure what to do with him, download some oral sex guides off the internet for both of you and learn how to do it from a pro – this works both ways, so practice and learn on each other.

The focus really doesn’t have to be on P-in-V action, and if your body just isn’t ready, maybe it’s time to shift the focus to becoming experts in oral sex and hand-jobs and getting each other off – to orgasm – other ways. No doubt your boyfriend would love to bring you to orgasm with his mouth, among other ways. Sexual intercourse, remember, isn’t just about making babies – it has a social function where we use it to connect with each other, making P-in-V sex wonderful indeed, but not the only “main course” of sexual activity.

Dealing with hidden anxiety and learning how to relax

You could have some anxiety present, which is completely normal, but your brain could be sending unconscious messages to your vagina to stay ‘shut’. To counteract this, take some deep breaths and deliberately relax each muscle, without just focusing on your vagina, but relaxing those muscles too. Sex is a physical, emotional and spiritual encounter with another person, not just having a penis in your vagina, so pay attention to the other aspects to be sure you are feeling happy, relaxed and horny. It matters!

Just because you were born in your body doesn’t make you automatically an expert, but it makes you the only one who can possibly be any good at it. Practice, experiment and master yourself.

I know it can seem maddening when you don’t understand how your own body works, but the work you do now is the starting point of your lifetime of great sex, so it’s important you learn about your body in a peaceful and holistic fashion: try everything! Twice. Once to see if you like it, and if you don’t like it, try again later just to be sure.

Dealing with discomfort along the way

Sometimes things will be uncomfortable, which just means you need to try a different way. It’s also ok to try something that hurts a bit if you want to as part of your explorations, to find where your edges are. It’s your sexual adventure, so get amongst it. It’s pretty hard to do any lasting damage.

Just try to make sure everything feels good, because otherwise, what’s the point? Sex is supposed to be fun, not painful, anxiety-ridden or uncomfortable, but there is indeed a long list of things you have to try, and discard, before you figure out what does feel good. This can mean a bit of pain and discomfort in your journey. Poking around in something you can’t see is always going to be an intrepid journey.

Could something be wrong?

If you think maybe something isn’t right in your vagina, like for example you have a blockage of some kind, it is advisable to visit your local sexual health clinic (there should be a free one around) and ask to be examined. If there is something to be found, it should be very easy to spot. (Undiscovered anatomical abnormalities, or maybe a growth like a cyst or tumour.)

If not, you know you have to work on this the long way – playing around and letting your inner dirty minx out to play.

The medical name for an unyielding vagina is vaginismus, but it is not a disease – it is often the result of psychological hindrances triggered by trauma, abuse in the past or by a current partner, or really anything your brain ‘didn’t like’, but it can also be triggered off by other medical conditions. If the inability to penetrate your vagina persists despite some sexy effort on your part, it does warrant further investigation.

Other ways to help open you up

If you feel out of your depth, or just want some help resolving it in a holistic and healthy fashion, you could try:

1. EFT/NLP therapy to retrain your brain and body without heaps of effort.

2. Meditating to relax – find guided meditations in a free app that offers ten free guided mediations called Headspace. There are many other options online too – find meditations that you like or ask for help from someone who is experienced – usually there is someone in your community offering free or cheap group meditations to start you off.

3. See a counsellor to deal with any past abuses or traumas that could be blocking your vagina.

4. Visit an osteopath to check your muscles and bone position (incorrect/poor posture can cause the wrong muscles to tighten).

5. Find a specialised sexual therapist who can help figure out the problem.

Or all of the above!

Your problem seems very solvable, so go forth and try it all.

Good luck, and let us know how you go!

Warmest regards,
Aunt Vadge


Jessica Lloyd - Naturopathic Practitioner, BHSc(N)

Jessica Lloyd - Naturopathic Practitioner, BHSc(N)

Jessica is a degree-qualified naturopath (BHSc) specialising in vulvovaginal health and disease, based in Melbourne, Australia.

Jessica is the owner and lead naturopath of My Vagina, and is a member of the:

  • International Society for the Study of Vulvovaginal Disease (ISSVD)
  • International Society for the Study of Women's Sexual Health (ISSWSH)
  • National Vulvodynia Association (NVA) Australia
  • New Zealand Vulvovaginal Society (ANZVS)
  • Australian Traditional Medicine Society (ATMS)
Read more about Jessica and My Vagina's origin story.
Jessica Lloyd - Naturopathic Practitioner, BHSc(N)

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