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Where It All Began

"The first lesson I learned from when I lost my virginity."

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Author's Notes

"I decided to go back to where it all began. Not the most erotic story but explains a lot about who I am. Even though this is a story about first kisses and first times, I think the leading role in this story should be my little erotica book. <p> [ADVERT] </p>I honestly didn’t realise how much it meant to me until I wrote this story."

I was pretty late to the party when it came to losing my virginity.

I had crushes in high school, but I was never able to go beyond that. I was at ease around my close peers and had wonderful friends, but I avoided interacting with other people.

I was notoriously shy and I stumbled over words and was totally insecure. I read books where I could escape into the world of the author. I listened to music, so I could hide in my room and escape from my own world.

I loved to write stories, and it was here on paper that my words never stuttered. I could manicure these words into beautiful paragraphs of expression. Refine them in my own time, and be as confident as I wanted and as sassy as I felt like. I was a poet. I was communicating in a way that made me comfortable.

I remember when I was sixteen, I stole a little book from my older sister. It was a book of erotica short stories. It was like finding a hidden treasure and that book hid under my mattress for years. It was probably the equivalent to a porn magazine that belonged to a teenage boy.

Those pages were well worn, ear-tagged with favourites, and fully covered in my pussy juices from reading them over and over again. As I masturbated to its words, over and over again.

In my hands I had a book of naughty sex stories, and it was my holy grail. For me, reading is an adventure and get to take trips to places all around the world. I met people of all different natures as they explored each other's bodies.

My obsession with erotica had begun. A fascination with cocks, pussies, clits, BDSM, head jobs, nipples, tits, breasts, and did I mention boobs? I read about fetishes and kinks and got excited about asses and their holes. I was addicted.

Our family didn’t have a computer at this stage, and it was well before we had the internet at the tips of our fingers. I think my current smart phone has enabled more porn videos than phone calls.

I have access to so much erotica. Stories by the thousands, with topics and categories to my heart's desire. I still take the time to appreciate that little book, though. I wish I had kept it for sentimental reasons, because I remember it often.

I’d quickly developed a fetish for breast play and masturbation, and I also knew how to be really quiet. This started my art of quiet orgasms. Quietly spoken and silently orgasming.

When I got to my senior year, I eventually let people read some of my poems and stories. They appreciated them, which was a relief because it was a big deal to let people into my mind. I also started to love the feeling of stepping over the imaginary line that was my comfort zone. I was slowly starting to feel more confident.

I’d had a few chances to have relationships after I turned eighteen and the first one was with a mate. He was funny, handsome, kind, and probably too good for me. He was so nice that I kept thinking that I’d struggle to break up with him if it didn’t work out.

I didn’t want to ever hurt his feelings. I didn’t allow him to be my first kiss, as much as I wanted to. I probably regret this a little because my sexual journey could be completely different if I’d settled for my friend, but would I be who I am today? I don’t think so.

There were a couple of others that aren’t even worth mentioning. A bit of putting myself out there but not getting anything in return. Rejection at its finest. Loneliness was starting to set in and friends were starting to couple up, and I was left walking home alone and masturbating to my little book of erotica.

So, then it finally happened. I was nearly nineteen, and a guy I’d liked in high school showed an interest. I think I was at the stage where I said,

"Fuck it! Let’s get this shit over and done with."

This was my moment. I could use this previous crush that I liked, but wasn’t attached to, to advance my sexual game to the next level. I could use him to teach me and further my reach outside my comfortability zone.

He was four years older than me and still had the same long, curly hair that he’d had in high school. He lived around the corner from my parents' house, and on this particular night we got a taxi home together, you know, for convenience. He asked if I wanted to come over for a drink, and I said, "Hells yes!"

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We had a drink, and I remember him kissing me, which was my very first kiss. Yes, my friends, you heard that right. First kiss and virginity all in one night, so no one can say that I do things in halves.

I don’t know what I expected from kissing, but it felt like he was licking the inside of my mouth. Nothing like what I’d read in the romance books. Damn those pesky, clever erotica writers with their amazingly visual imaginations, giving me false expectations.

He knew I was a virgin because we'd talked about it while hanging out together previously. He had an obvious liking for bigger girls, and as we got undressed, he turned down the lights to make me more comfortable. He knew how self-conscious I was, and I appreciated it. It was quickly developing into a really great experience.

As we lay kissing on his bed, he caressed my breasts and sucked in my nipples. I was in heaven. He let me touch his cock and showed me how to put on a condom. When I felt his penis, I was so intrigued. Soft skin, but hard underneath. He wasn’t huge, but he wasn't small either.

He lay on top of me and inserted his cock into my pussy. He pumped his hips, and I could feel his cock entering and leaving my pussy. I was excited and nervous. All the things I should be feeling for the first time. My legs came up and wrapped around his hips, so I could feel him entering me deeper.

He kissed and licked my neck as he thrust his hips forward. I was so nervous and wanted to try really hard to please him. He was breathing heavily in my ear. He put his arms under my knees to use my legs as leverage, and he kept thrusting his hips. Shoving his cock in and quickly pulling it back out.

He groaned and came, and before I knew it, our deed was done. His jerky movements slowed, and he pumped the last of his cum into the condom. I remember thinking that I didn't cum, but I assumed it was probably because I was so nervous.

After years of masturbating and reading my book of short stories, I think I foolishly thought all women could orgasm solely through penile penetration. It took me years of further reading to realise that clitoral-only orgasms were not only common but also normal.

He took off the condom, and I was awkwardly lying in his bed with the sheet over me. I will always remember the words that came out of his mouth.

"So this was just sex; don’t go falling in love with me or anything!" - The Lesson Giver

My reply came after a short pause, and I said, "As if I could now."

I jumped into bed, knowing that this wouldn’t transpire between us. I used him as much as he used me. I wasn't looking for a boyfriend, and I certainly wasn't looking for a long-term relationship.

I was looking for some mutual respect, someone to share this moment with. Someone to give me an experience, but I was treated like a naive virgin. Oh, right! Eye roll, that’s exactly what I was.

A night of first kisses. Tick.

A loss of virginity and a healthy dose of reality check. Tick-ity, fucking tick.

I got dressed and walked home. I was happy that the deed was done but confused by the lack of actual passion and pleasure. I was also somewhat confused by the lesson that I had just learned. I mean, I get it, but what makes him think that I would actually fall for him just because he’d been my first?

This was the catalyst for my promiscuous sex over the next few years. For years after this, I never had a regular relationship with a man. I used men, and I loved being used by them. If they took an interest in me, then that was all they needed, and they had me.

Was this healthy? Probably not, but I think I’d sexually freed myself without even realising it. Was I lonely? Yes, I was extremely lonely.

I don’t regret my first time. It happened for a reason and taught me lessons. I got where I am through my own twists and turns. The decisions I made and the people I chose to be intimate with. I’d go on to learn more lessons from my future sexual partners over the next few years, but those are future stories.

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Written by Helsbels
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