The Time I Made It My Mission To Lose My Virginity On Family Vacation


I was at a young ripe age, and fresh out of my first douchebag relationship. Throughout the course of that relationship I found myself more attracted to his nice truck and hot friends, rather than him which leads me to believe that’s the reason I wasn’t willing to give it up quite yet. I inevitably broke up with him, and the following week I was poolside in Maui on a family vacation.

This was no ordinary family vacation, and I knew it from the moment we landed. I had one goal in mind: I was gonna lose my virginity. I figured what could be better than losing the “V,” than losing it on the beaches of Hawaii. I was accompanied by one of my high school friends who was known to be on the wilder side, and I knew her and I together could be unstoppable. After six days of nonstop drinking and partying, it was the last night. I had 24 hours left, and I still had yet to find the oh-so lucky guy. After a long pep talk, I decided it was time to go on a mission. We threw back a few shots and made our way to the beach.

It was about 1 AM, and we were not really sure what we were doing, or where to go. The only thing I knew was that I wasn’t going back to that room without being deflowered. As we stumbled down the beach we happened to bump into two guys we had met the day before. That is when the mixed drinks full of Malibu began speaking for me as I grabbed one of the guys and flat out asked, “are you DTF?”

After about two minutes of conversation, that was about all it took. We knew what was about to go down. We walked a little further down the beach away from our friends until we found a nice enough spot in the sand. This was it. It was finally going to happen. As we started to tumble around in the sand, I paused and looked up to tell him that it was my first time. Not sure if this excited him or horrified him, but we skipped straight through foreplay, and within seconds our clothes were off and he was on top of me.

I was in no way physically ready for what was about to happen. The situation we were dealing with was drier than the Sahara. I had always pictured this moment to be romantic and sweet, but as the intercourse portion began I screamed in pain, and even shed a little tear. About 5 pumps later, the only thing on my mind was “is he done yet”? And there it was. I was no longer a card carrying virgin. Next thing I knew, I was being woken up by hotel security in the lobby of the wrong hotel.

Although anticlimactic, I did, indeed, get lei-ed in Hawaii.

Image via Shutterstock

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