This is another one from my trip to Puerto Rico.

Better off going around the corner to the Dominican Republic… In general, with meeting girls online there are four different scenarios:

  1. She meets me directly at my place.
  2. I meet her directly at her place.
  3. We meet in public, with the explicit understanding we are going to fuck as long as I am not a 300lb ogre.
  4. We just meet in public.

These are also ranked in order of my preference for obvious reasons. Throughout the course of our virtual interaction, I was getting the vibe that scenario four was going to be the only option.

I had her meet me at a hotel close to my Airbnb.

She showed up on time (something that is common in most parts of the world, but unheard of in my home city of Los Angeles) and had sweet, nerdy look…Not wow hot, but definitely cute. I gave her a confident hug and made a joke about how it’s been so long since we hung out.

She was hungry so we went to a nearby sushi place. Through out dinner, it became clear (at least to me) that we got along well… but there was no strong chemistry. We can be friends and have sex but put us on an island and we will be befriending the monkeys after a few days. I like to keep the conversation as light and non-serious as possible. Interview questions are best saved for after sex.

I liked her enough as a person to pay for dinner

Something that I’ll only do if I think the girl is genuinely a good person and doesn’t have any shades of a gold-digger. After the check, I took her hand and started walking to my place, without saying where we were going. Most of the time, if you are confident and don’t make a big deal out of it, the girl will go along with it.

We get to my apartment building and there is no resistance. We go in. Once inside, I can tell she feels a little awkward. So I avoid physically escalating and we chat about music for a few minutes… Then, I suggest we watch a movie. She agrees. I take my laptop and lead her to my bedroom.

She sits awkwardly upright on my bed

After a few minutes of technical errors, I throw on a random sci-fi movie. What follows next is about 30-40 minutes of slow “two steps forward, one step backward” escalation. This was made even more difficult, by the snail-like Puerto Rican Wifi speeds which would cause the movie to stop and create awkward silence at random intervals.

My game was pretty on point that night, otherwise, I’m not sure if I would’ve closed. I started, by putting my hand on her lap and gently massaging her thigh, but stopping as soon as I felt her body stiffen. Ten minutes in, I commented on how she has a nice Puerto Rican booty and casually gave it a squeeze. She playfully protested.

This kept going until eventually, I was massaging her ass…

Then we were making out. Then we stopped… Then I put her hand on my dick…. Then we stopped…This continued, all the way until she finally whispered in my ear asking if I have a condom. I took this as a green light and we smashed. She told me that I was the 7th-8th guy she’s ever been with and judging from her inexperience I can definitely believe it.