Your First Vacation With Daddy

By Trina

Dec 01, 2016

There are many “firsts” in Sugar relationships that the majority of couples on a budget won’t discuss until much later. If they can even afford it.

For instance, your vanilla boyfriend of two years may finally splurge to take you on a nice four day trip. After you’ve both saved, established trust, and a fair amount of time has passed, of course.

With a Sugar Daddy, these experiences (lavish gifts, vacations, etc.) can come at you hard, fast, and quick.That’s because time and money are no longer an issue. Within a week or two, your Sugar Daddy may offer to sweep you off of your feet to the vacation of your dreams.

The problem? This moved so quickly that you’re not sure how to act, what to wear, what to think, etc. Here are a few tips to help you keep your cool on your first vacation with Daddy.

Safety First

Let’s start with the priorities: your safety. This Daddy may be offering you the world on a platter, but you could be in a situation where you hardly know this man, and the concept of a vacation in an exotic, faraway location causes you more anxiety than happiness. If you have a gut feeling that this is not the right move, you should follow your intuition.

Spend as much time as your can with him prior to the vacation to get a sense of who he really is. Make sure he gives you details up front. If you trust him, it’s still always good to let someone know (a friend, acquaintance, confidante) where you’ll be headed and how long you plan to stay there. That is the only information you need to give them, although you can always give more based on your own personal comfort level.

Appropriate Attire

Now that we’ve focused on your safety, it’s time to talk Sugar. What will you wear? This is fairly simple, depending on the location of your vacation. Is is tropical? Pack a bikini, cover-up, sun dress, wedges and flip flops in a tote. Are you visiting a city? Comfortable (but fashionable) footwear is a must.

I always advise Sugar Babies to bring two versions of outfits—the sexy version and the “girl next door” version. Test the waters to see what Daddy’s personal preference is, or determine your outfit by the occasion (i.e. the beach may call for a sundress, but a night club would call for something a little more sensual).

Play It Cool

So, you’re in a remote location with your Daddy. Perhaps the two of you are still going to know each other. This can be nerve-wracking, because if anything goes awry, you’re in a set location with this person, at least for the time being.  This is why it’s incredibly important to establish what you have in common before this trip. What do you two have in common? What activities would you like to try when you arrive? It’s also important to establish your comfort level when it comes to rooming situations (Will you sleep in the same room? A separate one?)

Chat about things you know you agree on, and tread cautiously when discussing new, potentially sensitive subjects. You can save that talk for later dates and later trips. Remember to keep it light, upbeat, and positive for both of you.

Your comfort and safety should always be number one, but don’t allow “first vacation” nerves to persuade you out of a once-in-a-lifetime (or hopefully many times in a lifetime, if your arrangement works out well) experience. Assess the situation, use common sense, listen to your intuition, and above all–have fun. Happy Sugaring!