Stories from the Road: Isabella, Hot Caramel Latina


More memories from my expat adventures on Hispaniola

Stories from the Road | Bro Stories from my Travels

There I was in the middle of another idyllic tropical afternoon. I like to check in on a dating app I use once in a while to see what kind of tail is in town. I had seen this girl pop up from time to time on the app, and would later discover she lives in Santo Domingo but comes here to schmooze with the wealthy gringo expats and, though she won’t say it, look for one to take care of her as she impacts with The Wall in the next few years.

Meantime, she is 29, and although impact with The Wall is on the horizon this girl really has it going on. She’s still a stunner, and really must have been something when she was younger. Light brown skin, well kept hair, very pretty, with perky breasts and legs that evoke an old Bukowski quote in my mind…the one where he says there is a certain mystique about a woman’s legs, and a man always imagines there’s something more than just a cunt at the end of them. This girl definitely got my imagination flowing looking at her pictures, and then later, seeing her in person she did not disappoint.


I love being surrounded by women like this

Anyway, I made my move. “Hola, como estas. Cuando vamos tomar una cerveza?” She was quick on the response. After the usual pleasantries and such the conversation took a turn towards my intentions. She asked if I had a girlfriend, and of course assholes don’t care what women think so I said, “Si.” After some flirting and gaming and general assholery, she must have been taken in by my boldness and invited me over to her place by sending me a map. After sneaking out of the house while my main girlfriend was out, I walked around the barrios of town just after dark looking for her place but I could never find it. It was not to be that night. The map was wrong! Goddammit! After texting her to tell her the map she sent me was totally wrong, we talked and I finally figured out the general neighborhood she was in. But, my girl came home so we would have to wait to get this thing on until the next day.

The next afternoon, I found a way to get out of the house under the guise of walking for exercise, and Isabella told me she would stand outside and wait for me near the little vacation house she has, and that all I needed to do was find the road she was on. I found her, and after looking both ways to make sure nobody was following me and nobody who knew my main girl was around, I walked back with her to her place.

I walked in, and we talked for a few minutes while I marveled at her beautiful caramel body. When Latin women have it, they have it going on. I sent her photo to several of my closest bros and they all agreed she was quite the trophy. I knew it would never last because she was a high-class girl looking for an expensive meal ticket. But, I could at least visit the playground and break it in for some rich boy who she would no doubt end up with.


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First time intercourse is always a little awkward especially when you have just met a girl in person a few minutes before you are inside of them. She was even better looking than her photos. For a 29-year old, Isabella really has a great body. Before I knew it I had her bra off and her nipple in my mouth. I remember her dark nipples and the suppleness of her breasts. Before long I had her cunt in my face (I usually don’t do oral with strange girls but she was very clean) so I went for it.

The next thing I knew she was on top, then I was hitting it from behind, then I was on top. She really knows how to move en la cama so this ended up being 45 minutes of pure pleasure for the both of us. It was quite a ride. She really knows what she’s doing, much more than my regular girlfriend.

Before I knew it, I was sneaking down to her little place every few days and we were getting nasty together. But, this brings up one word of caution for the man considering becoming a player. Once a man gets used to strange all the time he will forever be craving that next “high” with a new chick. Something changes in the male mind and one sex partner, no matter how sexy and how awesome, just doesn’t do it anymore. After a few weeks of our on and off again sexual escapades and her trying to probe me to see if I would leave my girlfriend and go back to Santo Domingo with her, she had to go back home and I let her go. Alone.

She continued to invite me down to see her home in the capital but I had already moved on. I will always remember her though, as this girl is a real stunner and I had an awesome time wearing it out. She was incredibly sexy. But me, being the spoiled man I have turned into have already moved on to new pursuits with strange, new women. I’ve been through so much with women in my life once the thrill is gone, so am I. I have no patience for their needs and their lies and their wants. I tried it that way when I was younger, being the nice guy. It didn’t work. This does.

To those who would criticize: Don’t hate the player, hate the game. I’ve been on both sides of this coin, and trust me this is the better side to be on.

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One comment

  • You are living the dream. I’m going to have to live vicariously through you for a few years until I can make the jump myself. Fortunately, I’ve never married or had children so I have at least avoided the major pitfalls that would complicate that goal.


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