Losing my virginity: From 'Wanna do it?' to 'I peed funny!' in 10 minutes.











I thought I’d jump on the bandwagon and reference Fifty Shades of Grey in a piece of writing. Given my up-to-date timing, it’s obvious I’m very much on the cultural pulse.

To be honest, I needed a little time to take it all in. And not for the flushed, rosy-cheeked reason you’re thinking of. It wasn’t really my cup of tea, but I do think it’s fabulous that it’s awakened the sexual beast in so many women.

The thing that irritated me was the virginity scene. It was painless, pleasurable and perfect. Three things that I’m sure no woman associates with losing her virginity. An orgasm during the first time? Really? The bar was raised incredibly high for young virgins in Fifty Shades, and I’m worried that some (all) of them are in for a very rude awakening.

For a lady, losing one’s virginity is very rarely a pleasant experience. It can be with someone you love; it can be sweet. But it’s also going to be awkward, messy and it’s almost certainly going to hurt. I’ve never met a woman who orgasmed the first time. I’m sure it can happen, but there’s no way it’s the norm. And going in to that experience expecting earth-shattering, romantic waves of pleasure is going to leave a lot of girls very disappointed.

So I’d like to present a virginity story to offset the one in Fifty Shades: mine. No two virginity stories are the same, so I can’t speak for all women, but I would like to offer up something that makes others feel OK about their first time being more hilarious than romantic.


Here goes:

I was sixteen, he was my first serious boyfriend and we’d been rubbing up against each other pretty aggressively for a few weeks. Soon the top came off, then the bra. When we moved on to make-out sessions in just our knickers I knew it was time. There was nowhere else to go but… in. And don’t get me wrong – I wanted to, but I was a little scared. I’d only figured out how to use a tampon six months earlier, so I wasn’t exactly well acquainted with whatever the situation was down there. Let alone his weird-looking bits.

It wasn’t particularly magical when we gave it the go-ahead. It was the middle of the day and we’d somehow transitioned from Oprah into some heavy, almost-naked petting.


“Wanna do it?” I said. (Always the romantic.)

He acted sufficiently concerned about whether or not I was ready, although I’m certain that inwardly he was crying tears of joy for the balls that were slowly turning from blue to purple.

So, having begun the beautiful journey of giving up my flower by asking if we should ‘do it’, it was time to talk protection. I was on the pill already for my skin, but as sexual interns we felt we needed more. I remembered seeing condoms in the upstairs bathroom, so we decided on that plan of action. This is where things took a turn.


I think we both assumed that condoms were a one-size-fits-all situation. Did I mention we were sixteen? Anyway, after taking ten minutes to pry one out of its plastic-packet fortress, he went to put it on and… well… let’s just say whoever hid these condoms in the upstairs bathroom was not as well endowed as the young man currently in my bed.

Yep, it got stuck. Halfway down. It wasn’t going any further and it wasn’t coming back up. That thing was on tight, but we both assumed it was meant to be tight and if we just kept forcing it… Bad move.

Panic took hold of the room. I suggested scissors. He suggested scissors would go nowhere near his penis. I felt helpless, watching my first love hop around the room naked with tears streaming down his face. My next mistake? Deciding this was time to mention that my dad once told me cutting off blood flow like this is how farmers get animals’ tails to fall off.

He hurled himself onto the bed. I approached, not realising my naked body was only making the problem worse (you mean they can’t they control when it moves?). “Put your freaking top back on!” he yelled. I obliged, and gradually, the killer condom loosened. As soon as it seemed safe, I reached down and yanked it off.

It was the most intimate I had ever been with a penis.

Clearly, we had experienced a false start, but that wasn’t going to stop us from trying again. (Not that day, obviously, the remainder of which I spent scratching his head while he lay in the foetal position.)


It actually took a few more tries – I think the initial scare had caused me to close-up shop. And when it finally did happen, it was kind of by accident. We were in the midst of another make-out session when it just… slipped in. It hurt, definitely, but I think eventually, it gets to a point where the desire to make contact outweighs the fear of having a massive, foreign entity jammed inside you. So you just do it.

I can’t even remember the rest. The first thing I do remember is going to the toilet and laughing hysterically because my wee came out like a flood gate had been opened. And not yet understanding that a woman needs some mystique about her, I came running back into the bedroom screaming, “I peed funny! I peed funny!” A true class act.

So, multiple attempts at losing my virginity began with “Wanna do it?” and ended with “I peed funny”. Not exactly the most romantic of stories but that’s what I’m stuck with. I like it actually – it makes me laugh. It’s unique and I wouldn’t change it. It’s awkward and funny and sweet and slightly embarrassing. All the things a good virginity story should be.

But don’t let it encourage you to give up on a passionate Fifty Shades-style sex life. Things certainly get better; you’ve just got to get through some pretty awkward practice first. I was with that boyfriend for three years and we went on to have lots of pleasurable bedroom adventures. But that first time was the only time I peed funny. And things can only go up from there.

Was your first time as eventful as Rosie’s?