First Time Sex at 19 | Yes, ME!

This story won’t be released at Amazon, but I thought I’d share it with you and maybe you’ll enjoy it. Here’s a story about the very bizarre experience I had the first time I had sex at nineteen years old while on the island of Oahu in Hawaii.

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The First Time

Her flirty smiles over the shoulder of the guy she was dancing with caught my eye a number of times as I danced within feet of her. Her light wavy golden hair glistened gently all the colors of the rainbow in the sparkling lights of the Masquerade nightclub in Waikiki. I remember clearly Spandau Ballet’s True played perfectly through the BOSE speakers and it was shaping up to be a magical evening.

I don’t remember how it happened that we came to be dancing together that night. I was a bit lost in my own world, half-crocked on mai tais, and yet sober enough to see this girl was incredibly beautiful, and if I wasn’t mistaken, coming on to me.

We danced for thirty minutes or so, it was late and the club would be closing in fifteen minutes at 2:00 a.m. Beyond seductive smiles, attempts at communicating inside the loud club were fruitless, the music negated everything we said. We walked outside and sat at a bus stop to talk and stare into each other’s eyes without the smoke and fog of the club between us.

Her name was Heather. She was seventeen and from Squamish, British Columbia. Being a typical geographically challenged American, the word Columbia kept throwing me and I couldn’t help thinking she was from South America somewhere. She had also said Canada at some point during the conversation, so it wasn’t really making any sense to me at all that night. It didn’t matter so much. I was hypnotized by her incredible blue eyes and tall supermodel body.

She’d come with her father to the islands. He’d brought their maid with them. Heather had a separate room in the hotel, a major expense, but one that made obvious sense to her father.

Her mom had passed away when she was thirteen. She said her dad worked her dear mom to death.

Once we got off the morbid topics, she told me she would be coming back to Honolulu for a couple of months of college classes at the University of Hawaii – Manoa. That was great news because I figured I’d be seeing more of her then. Turns out, I was right.

At 2:30 a.m. on the bench we were sitting on, we kissed.

At 6:30 a.m., still sitting on the bench talking, we watched sunrise come up through the hotel skyscrapers and I drove her back to her hotel room. We met again at mid-afternoon and had a late lunch and then a couple hours at the beach for sunset.

I was surprised when she invited me to join her in her hotel room.

“What about your dad? What if he comes in and sees me?”

“He won’t. He leaves me alone when we come here. He has enough on his hands with Darla.”

I found out later that they came a couple of times a year for a week vacation and her father had never even knocked on her door. He left her entirely on her own.

I went up the hotel elevator with her. Eyes from workers at the front desk followed us, surely wondering who I was and if the father knew I was going to her room.

Nobody stopped us and we made it inside the room. It was the nicest hotel I’d ever been in at nineteen years old. Her dad had to be loaded.

She had a cassette player by the bed that she turned on. The eeriest sounds I’d ever heard came through the speakers. It was like we were in a voodoo ceremony or something. I had never heard anything like it.

“Do you know Yello? They’re my favorite band.”

“No, never heard of them.” I kept my opinion to myself, but the whole situation was already very odd. There I was with a seventeen-year-old in a five-hundred-dollar per night hotel, and her father in the room next door.

I love you!
I know.
I love you!
I know.

You know I need it while driving in the car.
You know this is dangerous, we’re going too far.
This is a sensual.
The way you drive is just sensational.


I hate to love you
Love you all the same
You know baby, driving is a serious game

Voodoo tribe music screamed loudly with hypnotic beats through the speakers of a stereo by the bed that was obviously going to continue playing while we did whatever was next. I felt a little bit like a lamb to the slaughter.

She came out of the restroom in a shiny satin pink negligee. Her beautiful blonde hair nearly to her waist. Her large breasts strained against the fabric. I was instantly primed, as you might imagine a nineteen-year-old would be.

I hadn’t had actual genital sex before, but I’d done everything else. It was looking like this might be the night I lost my true virginity. I was as ready as ever.

Tweaking it all up a notch, Lost Again, something like Amazonian jungle music began on the stereo. Here, listen for yourself.

I know this is crazy
Don’t ask where I come from
Don’t ask what I’m thinking
I told you lady…

She came over to the bed where I was sitting and it was mere seconds before what little clothes we had on flew across the room hitting furniture and fruit baskets. I ran my fingers softly through her hair and she grabbed overtop my hand and squeezed and pulled. My heart skipped a beat, but I obliged and grabbed tightly the hair near the back of her head, great handfuls of it, and squeezed, sending her into small squeals of ecstasy. I kissed her softly and she pulled closer, mashing our lips roughly against each other.

I have to admit to you, I didn’t know what I was doing. At nineteen, having grown up in Western Pennsylvania where the only sexual kink I’d ever had consisted of a blow job in the back seat of a girlfriend’s father’s car while he drove us to South Carolina on a family vacation.

Pulling a girl’s hair was new territory for me, but I seemed to be somewhat of a natural if Heather losing her mind was any indication.

She grabbed me with authority and yanked me to just within the threshold of pain, cupping and pulling my scrotum all in some bizarre, but very fulfilling rhythm.

We went immediately into a frenzied sixty-nine that culminated in a massive release. In five minutes we were at it again. I didn’t know if she would want to have sex or not, it didn’t really matter to me. My high school girlfriend wasn’t ready during the four years we dated. I was accustomed to waiting.

Heather wasn’t slowing down though. She pulled me on top of her and I began to enter her. Then, every muscle in her body tensed and she grabbed my arms forcefully, pushing me away. I stopped. We were both panting like overworked stallions. Then she pulled me to her chest for a while then grabbed my ass to pull me on top of her again, this time reaching down and guiding me in.

I enjoyed a quick two-inch dip this time before she again pushed away.

This charade went on for a good twenty minutes before I finally rolled off her and went into the shower. I was frustrated as hell and yet I fully respected her right to stop me if she wasn’t ready for it.

Was she a virgin? I didn’t know. It didn’t matter, the mood was going out of it for me. We were already through the Yello cassette front and back and now starting on side one again. The music, the situation, was so bizarre it was like I was on mushrooms – surreal.

In the restroom, she attacked me from behind and we did everything we’d done in bed up against the wall and on the floor of the shower.

Then we nearly ran back to the bed as she started the – give it to me, I don’t want it game a couple of more times. The last time it was me who pulled away, ready to jump off the bed and go home when she pulled me back, putting her face right up to mine whispering loudly, “I want you to FORCE ME TO DO IT.”

And that was how my first time having sex happened! This seventeen-year-old girl from the backwoods of Canada wanted me to push past her defenses and rape her to the backdrop of the craziest sounding music I had ever heard.

Maybe I was naive. Until she told me, I just wasn’t getting it. I’d never forced a girl to do anything, but as you can imagine, I certainly learned how to make Heather happy.

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The band Yello is famous for that song, “OH YEAH” which was a soundtrack tune for the “Ferris Bueller’s Day Off” film. The name of the Yello CD is “You Gotta Say Yes To Another Excess” and I strongly recommend listening to it if you haven’t before. Amazon has a link to the full CD with samples of songs here.

Pay particular attention to the really bizarre ones like:

  • I Love You
  • Lost Again
  • No More Words
  • Crashdance
  • The Swing
  • Smile On You

This became, during successive nights, one of my favorite collections of songs – ever.