Losing My Virginity over a Period of Four Months

Losing My Virginity over a Period of Four Months
by Anonymous

Parting Is Such Sweet Sorrow

At least, that’s what they all say. I suppose if used in certain contexts – a lover, a friend, a family member, even a childhood pet – this years-old cliché is true. However, if what you’re parting with is your hymen, and that parting isn’t going so well, let me tell you: parting is a goddamn relief.

Losing your virginity entails a lot of parting. First, there’s parting your legs. These logistics are fairly simple, taught to us through splits in gymnastics class, the basic physical education crab walk, and the lunges your mom does to “exercise” around the house. Then there’s what your abstinence-only sex education classes teach you: when you have sex you part with your innocence, your childhood and possibly your significant other. I parted with my innocence and my childhood when I found out Santa Claus didn’t exist, and I’m pretty sure nothing – not even sex – could bring me any lower than the first Christmas we didn’t put out reindeer food. As for the relationship aspect, I was two-and-a-half years into a relationship and we were going strong. Lastly, there was the most difficult part:

Parting with Your Hymen

The way people describe a hymen pushes it away from reality and more into a fantastical category. Before I actually parted with my hymen, I would have believed in unicorns before believing in this a basic piece of my anatomy. First, there’s the common phrase “popping the cherry.” Connoisseurs of sex use this phrase to make it sound…I don’t even know, but to me it just makes it all the more confusing. First of all, do you really “pop” a cherry? I have eaten many a cherry in my day and it seems more of a squish than a pop when I crunch it between my molars. Then of course there’s “breaking” your hymen. Now, instead of a cherry shoved between the walls of my vagina there is a piece of glass that will shatter when a penis touches it. No thank you. Not to mentioning the fact that some girls are told that tampons, riding a horse, or gymnastics will cause them to no longer be virgins. I mean, really? If a hymen holds that much power it has to be magical. Not just a piece of anatomy, but a sign that everyone can see that says “I’m a whore” no matter how you lost your virginity. I thought you lost your virginity when a penis entered your vagina but apparently, I was wrong. That magical moment when a tampon pushes a little too deep or a little too hard, that’s the moment all girls should be writing about in their journal labeled “TOP SECRET” with hearts on the cover.

Then there are the descriptions of how it actually feels when you part with your hymen. Considering the amount of mystery wrapped around it, I’m fairly sure it’s the number one most-googled question before each girl loses her virginity. Some say they don’t even feel it. Others say it’s a “sharp pinch” followed my relief and pleasure. Even more say it takes a couple times for it to stop hurting.

So, when our clothes were off and the door was locked, I attempted to – in technical terms – part with my hymen (with help from my boyfriend). There was the assumed fumbling and awkwardness, laughed off as we attempted to roll on a condom and situate ourselves comfortably. Then there was the final moment, preceded with a tensing of every muscle in my body, which I began to lose my virginity.

Okay, Tried (Trying?)

There was pain as my boyfriend pushed into me, and before I could ask myself when the “sharp pinch” would end there was a wall. I gasped loudly and tears pricked my eyes as my boyfriend attempted to go more than an inch deep inside of me. He failed and the pain was too much for me to bear. Both of us being virgins, we had no idea what was supposed to happen and attempted to fix the solution, fairly sure that his penis was supposed to go more than a third of the way inside of my vagina. However every time we tried, there was that wall again, ever-present, and what I assumed was my mythical, fantastical, horrible hymen.

“Maybe it will loosen up if you push harder?” I asked my boyfriend.

“I don’t want to hurt you.”

“You won’t.”

“I’m not going to push harder if it hurts you.” He refused to budge on the subject and as a result I collapsed into a puddle of tears, naked, while a condom was still rolled onto my boyfriend. He awkwardly held me and asked what was wrong but what could I say?

I don’t think there’s a way to explain how much of a failure you feel like when you’re unable to perform a basic biological function. I mean, there are 12-year-olds having sex and getting pregnant with strangers yet I’m unable to have safe sex with a man that I love? Also, given the stigma of sex in our society, it wasn’t like I could have gone to the nearest adult and ask how sex was supposed to feel.

For the week that my boyfriend visited – he went to college in New York, I here in Virginia – we attempted and failed at having sex. My boyfriend left with a kiss on my forehead and the positive words “we can try again in a few months.”

Trying Again

We tried again a few months later, I think it was during Thanksgiving break, and failed. That’s when I completely lost it: I called my mother. My mother has always been an open, loving person and felt no need for tsk-ing at my personal decisions. But calling her about my sex life? A more embarrassing phone call has never happened in my life. It went something along the lines of:

“Hey, mom.”

“Hey! How are you?”

“Well…I’m good. But there’s this thing?”

“Yes?” I’m fairly sure at this point her heart has stopped and was waiting for the declaration of my teenage pregnancy.

“Well, Eric and I had sex,” insert a larger intake of breath from my mother, “and I don’t think it went how it was supposed to…there was a lot of pain. More than I think there was supposed to be.”

Twenty minutes and an ob/gyn appointment later, my mother officially knew I wasn’t a virgin. Though the newest low in this wonderful journey was yet to come.


With your feet in the stirrups at the ob/gyn, you reach a new level of embarrassment. Your legs are completely spread – an extent to which I’m sure no Catholic nuns approve of, regardless of the medical reason – and a person’s head is located approximately at your knees. To make matters even worse in my situation, my gynecologist was what I like to call elbow-deep inside of me. She was looking for a “micro tear,” the supposed cause for my dyspareunia, a fancy word for painful sexual intercourse. The doctor attempted to find this tear by inserting multiple fingers inside of me and pushing around as if a micro tear will appear like braille on the walls of my vagina. Though, I’m not a doctor so maybe that’s exactly how it goes.

In order to find this micro tear more efficiently, the aggressive doctor asked my how the pain felt and where it was located. I hated this question – and still do – because pain is pain, especially when it comes to parts that are inside of you. At the time I didn’t even know what I had eaten for breakfast, so I was even less likely to know exactly where this pain was located.

“The right side?” I ventured, trying to think back three weeks, to the last time I had had sex. Her hands reached even farther and pushed, to no avail. She pulled out her gloved hands, as if they hadn’t been inside of me for the past half an hour and shook her head.

“I don’t feel anything,” she said, her voice seeming to chastise me for being a wimp on the sexual pain factor.

“Well something is there,” I insisted, forcing her to once more penetrate me while I laid back on that crinkly white paper at all doctors’ offices. To me it felt like the cheap toilet paper at public schools and I wondered idly at the time if they had the same supplier. A supplier whose life goal was to make the most uncomfortable people – patients and public school students – even more uncomfortable when they were either ass-up on a table or wiping their ass in a bathroom stall. Above my wide-spread knees my doctor looked up in triumph.



Thanks to my encouragement, she was able to find that my hymen on the right-hand side was thick, too thick. This made it unable to break on its own. This came the fun – actually, completely horrible – part. In order to have normal sex I would have to take a month manually stretching out my hymen.

I won’t go into details, but let’s leave it at this: masturbating is fun if you’re choosing to do it for pleasure. Having to masturbate every day, to stretch out your hymen, while you mother knows you have to do it – that’s beyond explanation.

However, the doctor was right and my hour-long-total molestation paid off. Normal sex is now attainable and my hymen was effectively broken through a month of hard work. And after the two months of failed sex, a month where I waited for my doctor’s appointment and the month of doctor-prescribed masturbation all I can say now, in regards to my hymen, is: parting is a goddamn relief.

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