Losing your virginity: DIY

brown uninterrupted
4 min readNov 3, 2020
Photo by Dainis Graveris from Pexels

In light of normalising sexuality and sex and the fact that it is a fundamental part of being human, here’s an exposé on losing your virginity — to yourself.

The terms “virginity” or “virgin” always irked me.

Maybe it’s the unconscious bias, the potential societal embarrassment of saying you’re one. But, why does losing your virginity have to be a milestone in life? Why does anyone have to judge the age at which one loses their virginity? Why does the age at which you lose your virginity somehow define you sexuality or your open-mindedness?

Maybe it’s my extreme independence that I’d like to say I don’t need no man, I lost my virginity to myself. That’s what fingers and dildo’s are for, no? Do I really need to have had penetrative sex with another human in order for me to say I’m no longer a virgin?

But, this post isn’t a rant about the societal constructs around virginity. This is to all the curious but slightly afraid girls who want to know what sexual exploration, awakening, liberation, pleasure whatever you want to call it feels like but aren’t sure how to go about it.

Most of us understand how sex and other associated erotic activities work. But, no one really speaks about what it feels like or what to expect. They tell you what to expect when you’re expecting but no one ever tells you what to expect to get to that stage.

I spent most of my teens and 20s claiming to be asexual. It was easier to tell everyone that I was asexual than to get into a deep conversation on why I couldn’t bring myself to be intimate with anyone. Because anyone touching me in any kind of way, triggered memories of sexual abuse I didn’t want to remember.

But, that didn’t mean I did not crave romance and intimacy — the sort you see on TV. I just wasn’t ready to explore or share it with another human. I watched my fair share of porn, fancied the men on TV, fantasised them making love to me, moderate attempts at masturbating including an embarrassing moment when my dad caught 18 year old me humping a bolster when he came to check on me to see if I feel asleep studying. The horror.

My sexual explorations never went further than bolster-humping until I was emotionally and physically ready to be around men romantically, years later.

So, here‘s a late-bloomer’s guide that I wish I had:

Boys

The first boy I was with — things escalated quickly from cuddling to making out to clothes off and him wanting me on top. Having watched this very sequence of events on film and porn many times, I’d confidently assumed this was an easy in, pun intended.

No entry, cockblock. We swapped with him on top. No entry, again.

I saw it in his face and he instantly knew I’d not done this before. For a long time, I kept replaying his face in my head because it was mildly embarrassing and disappointing. I hated that I felt that way, I shouldn’t have.

It looks so easy on screen but girls, for some of us, you can’t just stick it in. Some deeper reading and open conversations with close friends revealed that some of us require enough foreplay to open up our orifices.

A friend advised: “Typical straight guy. They never get that an extra 20 minutes foreplay means you could f*** like horses after that with no inhibitions.”

Fingers

The feeling of not being able to deliver meant my hyper-independence kicked in and I needed to take it into my own hands to open myself up. The thrill of the challenge made me bold enough to stick a finger in.

But, I never quite got to two until a few months, which was frustrating. I diagnosed myself with an inability to have penetrative vaginal sex — dr google said it could be Vaginismus.

Having now managed two fingers in months later, I was still experiencing performance anxiety, which held me back from future adventures.

*enter* Toys

My best friend, gifted me a vibrator to get through my “dry spells”. Both of us inexperienced in this matter, later educated ourselves that there are different types — ones that stimulate your clit, i.e., wands and others that facilitate penetration, i.e., dildos.

I invested in a dildo because I really wanted to be less stressed about no entry and enjoy it when I was with a boy I liked. But no amount of porn or erotic literature could open up those tight orifices.

Enjoy

As if by divine intervention, I started dating a boy I was completely comfortable with, sexually. We were sexting for a few weeks and that helped loosen up my inhibitions. This “losing virginity” became something I wanted to enjoy versus something I needed to achieve.

I wasn’t pressured to perform to prove I could do this, I was relaxed enough to enjoy. And I remember being pleasantly surprised but that dildo slid right in — because I was wet and warm enough — opening me up to seek, explore and enjoy pleasures on my own or with partners.

My hyper-independent self was proud of losing my virginity to myself, on my own effort. It is a completely weird concept that potentially only a sociopath like me could come up with but I am not going to lie, I felt more confident, relaxed and at the risk of cringing at myself, liberated.

Let’s stop looking at “losing virginity” or “having sex” as something to attain, a milestone to cross by a certain age, a definition of your “open-mindedness” or one that needs to happen with someone else.

Let’s make sexuality something to enjoy exploring and have fun with in our own time, space, pace, and comfort.

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brown uninterrupted

For the longest time, speaking out was out of character for (brown) girls like me. So, here’re stories that are easier written than spoken, uninterrupted.