Hot sex on a Passport? (Part II: Hot and not so Bothered in Negril)

“Tucker, we’re going to the store.  Wanna come?”

“Is he going?”


“Then I’m going.  Come on.”

*Stunned stares*

It was Memorial Day Weekend 2007.  After the debauchery of Memorial Day Weekend in Miami the previous year (perhaps I’ll make a post about it…besides, it was my first trip after all) I decided I wanted a more low-key destination.  A few friends decided on Jamaica, and I agreed.  We spent a few days in Montego Bay before voting to head down to Negril for the day.  I suppose it was fate, but we literally chose the first hotel that looked pretty nice.

Good choice indeed.

The owner was an older, Jamaican gentlemen, who then introduced us his sons.  All accomplished.  All handsome.

Especially the youngest.

I won’t reveal his name out of respect (I’ll just call him “Crush”), but I must say that I found myself instantly attracted to him.  Tall, nice smile, caramel complexion, a very good combination.  As a bonus, I found him to be very friendly and welcoming.   It was official.  I had a vacation crush (which I suppose now in 2016 this would be known as a potential mini-Baecation).  As he spoke about his life and goals all I could do is sit and stare, trying desperately not to look so obvious.  If the smirks from my friends were any indication, I was failing miserably.  Back then I was hardly what anyone would refer to as a “bold” woman, but when I was asked about going to the store I had to make my dorky flirtatious move.  He seemed taken aback by the statement, but at least he didn’t show visible disgust (I mean, das good rite?)

Later on that night, we all packed into a van to attend a weekly outdoor event known as “Happy Mondays.”  For those who are not at least somewhat familiar with Jamaican dancehall culture, Happy Mondays is modeled after “Passa Passa,” an outdoor party that lasts throughout the night and can get quite wild.  None of us were in the mood to stay too long, but wanted to at least enjoy a little music.

There was no way that I was going to ask to dance with Crush, so I elected to merely stand beside him and enjoy the music.  Imagine my surprise and excitement when he grabs me, pulls me in, and asks, “where are you going” while I attempted to walk away for something to drink.

Shortly after, we make our way back to the hotel.  Crush tells us that he is just going to stay downstairs and we head to our room.

(Pardon the language)





(PLEASE pardon the language)





“He is down there!  This is your chance to go make it happen!”

“Make what happen?”

“You know what you DUMMY!  Get outta here!”

Honestly speaking, I didn’t even think about making anything “happen” with Crush before, but I would be lying if at that very moment, for the very first time in my life, I didn’t give “making it happen” some serious thought.  I mean, why should I have been worried about what he would think of me?  Besides, I’d never see him again right?  Then doubt creeps in.  What if he turned me down flat?  I’ve never been able to handle rejection well.

I was tempted to at least see if I could get a kiss out of him, but alas fear prevailed in the end.  Fear of the unknown.  Fear of rejection.  Fear of Herpes.

Yes, the same hangups I have about sexually transmitted infections now  (which I briefly discussed in part I) I held back then.  I just couldn’t imagine myself going through with it.  I was, and still am very scared of catching something I cannot throw back.  What did transpire that night was four girls and one guy in one hotel room having the most absurdly hilarious conversation deep into the night.  I never talked so much trash about what I was going to do if I had the chance (except I actually had the chance and didn’t capitalize).

Whenever I have to defend myself against accusations of being prudish or having draconian ideas regarding sexuality, deep in the back of mind I think of this experience.  Although I do have normal sexual thoughts as  a woman who is 30+, it has always been difficult for me to imagine having sexual intercourse with someone I just met.  There are plenty of people who would not have thought twice about “making it happen” (more on that in part III).   The weather was beautiful, the vibe was cool, and the attraction was there.

I was hot, but not so bothered.

Enough at least.


Have you ever had a sexual encounter while on vacation?  Please take the ANONYMOUS survey here Sexy Time on Vacation and rest assured that I will not know who responded…







You free spirited whores ( just kidding 😀 ).


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