How I Slept with 51 Dominican Girls in 4 Short Months

Last Updated Nov 25, 2021

My time in the Dominican Republic was nothing short of epic.  Dominican girls are some of the hottest women in the world.

My journey saw me through Santo Domingo > Cabarete > Santiago > Cabarete > Santo Domingo.

I will share a lot of information about this small Caribbean jewel and may someday dedicate a book to it.

This post serves as a microcosm of why I love Dominican women.

Ups and Downs in the DR

During my time in the Dominican, I engaged in some of the freakiest, most ardent and flat-out fabulous lovemaking of my life.  The Dominican girls were ambitious in the bedroom, fiery in nature and stacked.

There were dangerous times packed in there as well – walking the tightrope so to speak.

Living in Santo Domingo made me more street smart than any other city I have visited.


A staph infection in my elbow left me sidelined for a month over Christmas.

It required surgery, and luckily, my travel insurance covered the total cost (over $2k).  It stemmed from a minor motorcycle accident.

Scoring like a Pro in the Dominican

After I healed, I went on an absolute tear that put a stamp on my time in the DR.  While still tending to the wound, I hit the online dating market hard in the month of January.

In 21 days, I hooked up with 31 Dominican girls including some repeats.

I reached 51 lays total and had my first 4 threesomes in a 4-month period.

Most of my time was spent in Santo Domingo followed by Cabarete.

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Some Unlocked Achievements:

  • Hooked up with my first Dominicana
  • Hooked up with my first Haitian
  • Had my first threesome with one Haitian and one Dominicana
  • 4 threesomes in total, all FFM, and one was with half sisters
  • Had one girl pleasure my jewels while the other attended to my limb (the half-sisters)
  • Achieved 4 girls in a 24-hour period, including my first threesome
  • Continued to achieve 5 girls in a 36-hour period to cap off the 4 girl achievement
  • Deflowered a stunning 18-year-old virgin, white Dominicana w/ green eyes and freckles
  • Dated an 18-yr-old for a month that resembles Rihanna
  • Discovered the amazingness of baby oil in bed
  • Played with the biggest melons I have ever seen in my life, time and time again
  • The Holy Grail achievement of a different girl for every day of a month.  I accomplished the feat in 21 days with 31 girls including 3 threesomes.  Every day was dedicated to finding a new girl(s).

Other Interesting Achievements:

  • Learned how to surf
  • Learned how to ride a motorcycle
  • Upgraded my street smarts
  • Survived a staph infection
  • Wrote a bunch of Ukulele Songs
  • Discovered the true nature of cigar smoking and made a Dominican friend for life
  • Discovered that I needed to start working online
  • Took my overall virility to a more evolved state
  • Evolved as a man after making lasting connections with some of the most beautiful people in the world

The Dominican Republic enhanced my life on countless levels.  The culture is exceptional.  Here is a list of some of the Pros and Cons:


  • Dominican Girls have huge curves and are fiery in the bedroom.
  • Dominican Women are tighter and moister than American Women.  I have experienced this in general with women of Latina descent.
  • Foreigner value is high.
  • Beaches are great for surfing and kitesurfing.
  • Relatively cheap
  • Easy to travel around the island
  • People are welcoming in general.
  • Cheap fresh coconut juice on every corner
  • I love avocados and have tasted varieties from around the world.  The best ones I have eaten were from Hawaii, Dominican Republic (Street vendor in Santo Domingo) and Medellin in an expansive Colombian market (Chilean Variety)


  • It’s hot.
  • It’s dangerous at night in some sections and sometimes during the day.
  • Locals constantly try to rip off foreigners.
  • The food is not great, a lot of fried food and rice.
  • If you’re dating girls outside of online, beware of pros (I used almost no night/street game to avoid them)
  • Dominican girls can be flaky, but it’s nothing compared to some other countries.

Seducing Dominicanas

I almost exclusively used online dating to find dates.  Dominican Cupid boosted my success.  That’s where I found my GF and other curvy Dominican girls.

The Hidden Online Gem

During my time there in 2014-2015, this dating site was an absolute goldmine.  It was like living in a dream world the way the dates just kept rolling in.  I should write them a check someday.

The best part was talking about sex upfront worked well.  I began making leads a month or so in advance.


Over that span, girls sent me risqué photos, videos, texts, and confirmations of meeting upon my arrival.

Arriving in Santo Domingo

Upon arriving, a lot of the dates came fast with some of my favorite girls.  If you’re a curves guy, this is your Mecca.  I can not stress this enough!

Dominican women do range.  There are a lot of mixed-race women and even white Dominican women.

City Overviews

In Santiago, the Dominican girls are a little paler with longer hair.  After spending time in Colombia, some Dominican women remind me of Colombianas, especially the women I saw in Santiago.  I was only in Santiago for a couple of days.

In Santo Domingo, the women have darker complexions with more prolific curves.  If you are a fan of an occasional large round fiesta, like me, you will enjoy this place.  Since it’s the capital and largest city in the country, the women are diverse.  The girl I dated the longest was from here.  She was long and thin with a beautiful face.  Her eyes were mesmerizing.


Cabarete is not a great spot for dating, but my Dominican buddy was the consummate wingman.  Cabarete is next to Sosua, a place where men from all over the world travel to meet pros.  I only went there one night with my Dominican friend after we blazed.  We enjoyed some hearty laughter that night.

The reason Cabarete is awesome is that there is a surfing beach close by and the kitesurfing culture.  It is a nice place to go with a GF and do some surfing.  You can also find women from all over the world in this little town depending on the season.

Highlights in the DR

I’d like to highlight one girl who sent me a legendary video before I arrived.  She was a petite, cinnamon goddess.  She set the tone for my entire voyage.

On my second day there, I was lucky enough to meet her, and oh the things we did that day.

I hope this article serves as a decent overview of the Dominican Republic.

It’s an incredible Caribbean country for numerous reasons, and the fiery feminine women make it a must-see for any savvy bachelor.


  1. Josh Bar

    Great stuff !
    What are your travel plans for 2016?

    • 199Flags

      What’s up Josh? glad to see you here. I’ve got some plans in the cooker. Thinking of going back through South America for a couple months before Eruope or going straight to Eastern Europe. How about you?

      • Josh Bar

        DR, Brazil, Colombia this summer

      • Josh Bar

        DR, Brazil, Colombia this summer

        • 199Flags

          Good plan. If you need any info on the DR or Colombia let me know. I may go down there myself, it’s hard to stay out of Colombia after tasting the nectar. Good Latina pussy is like opening a fresh bag of skittles.

    • 199Flags

      What’s up Josh? glad to see you here. I’ve got some plans in the cooker. Thinking of going back through South America for a couple months before Eruope or going straight to Eastern Europe. How about you?

  2. Josh Bar

    How many you RAW dog?!?

    • 199Flags

      haha well there was virgin, the second girl I banged that was 18 and 1 black girl I know for sure. I think after the black girl had her period late, I started wrapping up every time.

    • 199Flags

      haha well there was virgin, the second girl I banged that was 18 and 1 black girl I know for sure. I think after the black girl had her period late, I started wrapping up every time.

  3. Stefan

    Can you describe how did you arrange the meetings with the girls?
    Did you go to restaurants, bar, dancing clubs and then offered “perhaps we can go to my place?” 🙂

    • 199Flags

      Dominican girls are very sexual, but the important part is weeding out the hookers. A lot of girls were willing to come to my place or meet close by if I paid for the taxi.

      I’m not really into nightlife, but I’d assume there’s a lot of Dominican hookers lingering in there.

      Finding girls who are students is your best bet. Achieving 100% free sex in the Dominican is no easy task though. The best way is agreeing to pay the taxi with girls who don’t live very far.

      The women are hot enough where it’s worth spending money anyway. The boobs alone.

      • Stefan

        Thank you for quick reply.

        I have other questions, many of them :):
        1. You were so successful, that it sounds awesome. Co you look like a mix of DiCaprio and 50 cent? 🙂
        2. How did you manage threesome? Found two girls at the same time or asking two separate girls if they want play that game
        3. How can I make a quick hooker-test (to eliminate them?) 🙂
        4. So you met girls online, proposed meeting and the only think what you have paid was taxi?! 🙂 You didn’t go out with them for a “date”
        5. I read somewhere always to ask BEFORE going to your place if the girl wants money
        6. What about your spanish? Did you communicate in spanish or in english?
        7. How looked your day like? Online chatting, date, online chatting date. Did you find time to speak with them a little bit? 🙂
        8. Did you rent a flat and brought the girls there?
        9. What about safety? Some strange experiences with the girls?

        Again thanks for quick response

        • 199Flags

          if you’re interested in a consultation email me at If not, have a great trip! You’ll do well there.

          I can answer most of these questions with my will and levels of hunger. Like someone great once told me, if you want it in your heart, you’ll get it. If you’re heart isn’t in it, you won’t succeed.

  4. Brianmark

    What towns did you find were the best for hunting?

    • 199Flags

      Santo Domingo is my favorite, but it’s definitely not for everyone. A lot of guys prefer Santiago.

      • Brianmark

        I made my first trip to DR in January. Were you in Boca Chica? Do you speak Spanish? I think it’s only OK. The girls are mercenary. There are many guys that want to be your “tour guide,” but are just leeches.

        • 199Flags

          Yeah, it’s important to be careful with who you trust in the Dominican. Dominicans will want to start coming to your place and party haha. Boca Chica is more touristic, I never went there. I love Dominican women.

  5. kc


    I noticed yours and other sites mention the Cupid sites as a good hookup resource . I’ve browsed most of the sites I’m interested in and it seems to be full of gold diggers,phony profiles and girls who are aware of it being used to hookup up. Many of the better looking girls who aren’t gold diggers seem to have or are being hit up by mostly old guys with no game looking for a fling.Are there any indicators in profiles or filters that can be used to weed out the ones who aren’t looking to hookup.

    • 199Flags

      I’ve seen similar concerns, and the first question I’ll ask is did you actually sign up, pay, and use the site? Which site are you finding golddiggers?

      In my extensive experience using these sites, I’ve had GREAT success. I run into zero golddiggers, and old guys with no game don’t affect my game.

      Where is your game level? Personally, I don’t talk to girls about hooking up before I meet them. You won’t find much quality with that approach. If you’re seasoned all need is to get on the date and let your game do the rest.

      Phony profiles I’ve never seen on cupid sites so again which site are you using? If it’s a site I’ve used and reviewed on 199flags, I’m not following where you’re coming from.

      • kc

        I actually signed up (I haven’t paid)and browsed the Cupid sites due to discussions I’ve seen online.I consider a profile phony when it only a picture or just pictures and no profile details.As far as what im mean gold diggers I’m referring to girls who are:

        Young and looking for old guys with high incomes in major cities like New York.

        These are girls I was actually searching for but still seem to show up randomly.

        My comments were meant as an attack just how to find girls that actually fit the ones described in this post.

        • 199Flags

          I know it wasn’t an attack and neither was my response. Considering users can’t message girls without paying, I don’t know how you came to your conclusions. Also, I don’t recommend using Cupid sites to find girls in America, better to use Tinder.

          Cupid sites are best reserved for use in other countries e.g. SEA and Latin America. Best of luck!

    • HitNquit

      Cupid is a goldmine for women if you weed through them.I avoid the long whatsapp bs.Usually get going online week or so before i go an however long you are there you will leave sore an tired from all the work u just put in.Never a night off.1st chat nude pics i notice is gimmie $$..Dont lol ,skip on to the next ,your phone will never stop beeping.Who cares who is chatting them up Old ppl or not as they are usually old fkers in another country jerking off to them an you are there…..They will work them an fuck you.I agree with 199 it gets crazy esp- @ night.Online game is the best weapon,

      • 199Flags

        Now, this is the truth. The only complaints I’ve seen come from guys who never paid to use the site. Considering it’s not possible to message girls without paying, I don’t know where they come up with the complaints.

        The site’s interface may look old, but it’s a goldmine if you know how to filter. All a guy really needs to do is go platinum, post a few good photos, then copy and paste messages to all the girls he’s interested in.

        Sure, there will be some duds. Why waste time of duds? Getting laid is a numbers game, and there’s a lot of quality tang on Cupid sites with less competition from other guys. When a dating site gets overpacked with dudes, it’s instantly ruined. This doesn’t happen on Cupid.

  6. HitNquit

    I don`t know how i came across this, though so true an so funny.Nice job writing it can not stop laughing.

    • 199Flags

      Laugh it up amigo! That’s what running these schemes is all about 🙂

  7. Ed

    Big dawg when was the last time you were in Santo Domingo? My cousin and Will be there in May 2019. We stayed In Santiago last year May and I bang 3 girls in a 24 hour time period. This go around we want to see what the Capital is all about. I’m a on Dominican Cupid now and got many baddies numbers. Great post, got me excited about this trip.

    • 199flags

      Nice! I haven’t been there since 2015, but I’m planning to return someday. I think you’re going to like Santo Domingo even more than Santiago, depending on your taste. I really like the vibe in Santo Domingo. The energy of the place gets in my bones. Have a blast and report back after your trip.

      Cupid treated me well in Santo Domingo. The mass message approach is the way to go, then filter through the replies.

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