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Travelling On Extended Dates With Your Favorite Companion

Sex Ed

Travelling On Extended Dates With Your Favorite Companion

I believe traveling and going on extended dates is gaining in popularity. In my opinion, it seemed as though it was previously restricted to mistresses and sugar babies. However, it appears that the idea of travelling with, or spending long durations with your escort is growing in popularity.

I’m always reminding clients and civilians that while of course there’s the boundaries within the framework of the client/companion relationship – there’s ultimately no rules in terms of how you can spend your time together. It is in fact, a relationship, albeit an unconventional one.

When I originally began in this industry, it seemed as if extended duration dates weren’t exactly in demand (or maybe they weren’t for me!)

Many of my clients didn’t realize that I’d even be open to the idea of spending longer with them, let alone feel ecstatic. I know many providers also feel the same way.

I think people are beginning to understand that the friendship you can create with your favourite provider is both of yours to design. We can see each other as often, or as infrequent as you want, and for as long as we’re both comfortable.

Reasons Clients Engage A Travelling Companion

Travelling can be such an amazing experience. Being a big backpacker myself, I’m often finding myself in serene moments, wishing I had someone to share it with.

I think that as the relationship between a companion and her client develops, it can turn into this wonderfully fulfilling, mutually enjoyable experience. It truly is a friendship, and often times, at the end of our dates, my clients and I both wish we had longer together.

Sneaking away for a long weekend, or few days away, allows us to fully let our hair down and unwind from the daily stressors of life. You can be absent from office politics, deadlines, family conflict, and truly be in the moment with her. Think of it as an oasis. There’s something extraordinarily healing when you’re only thought is the way her skin feels under your fingertips.

Preparation Required For The Client Before The Date

This depends on whether you’re meeting her for the first time, or she’s already an established friend.

Some of my best experiences came from a leap of faith, where I flew across the country to spend a few days with a new gentleman. Travelling together on a first date isn’t common, but it does take a lot more preparation on both ends.

For the gentleman, I’d hope that you’ve done your research, and chosen to reach out to someone who really vibes with you. Does her personality seem introverted or extroverted? Do you like the same hobbies? Spending several days together can be either be the most rewarding, or painful experience – make sure you’re spending time with someone you’ll really get along with.

Regardless whether it’s a new friend, or someone you’ve known for a while, there’s still quite a bit of communication required before either of you get on a plane.

How long have you agreed to spend together? When does the time begin? Will you be travelling separately, or together? What is the exact compensation, and how will she receive it? I know it can seem transactional to go over the finer details, however, assumptions and important information left to chance can spoil even the most romantic getaway. Make sure you’re both on the same page.

Last but not least, consider your companion’s preferences, and work out a system that works for you both. As I mentioned, it is a relationship after all. Is she an early bird, or a night owl? Does she need caffeine before functioning? Is there anything you can prepare ahead of time to make her time with you more comfortable? Gentlemanliness goes a long way.

Are There Rules?

Often times, yes! However, every companion is vastly different, as is every client.

When spending extended time together, I encourage both parties to be upfront about their needs. Does he need to fit in a workout first thing? Does she have a daily yoga practice she’s hoping not to neglect? An hour at night for both to catch up on business?

Don’t be afraid to design an environment and relationship that makes you both comfortable. I know of several companions who require a little “alone time” here and there to recharge, while I’m generally okay without it.

Personally, I absolutely must sleep 8+ hours a night, and have tea in the a.m.

My only rule: “Don’t wake me up!


Madison Winter – Madison Winter, Canada’s self-proclaimed ‘girl next door’ is a high-end companion who lives and works out of Toronto, ON.

She’s left a career in finance to become a provider, and now specializes in long engagements and relationship-based dates. In her spare time, she’s usually collecting passport stamps, or at home with her two dogs jamming out to 80’s rock.

Follow Madison Winter on

Website: https://madisonwinterto.com/

Twitter: https://twitter.com/madisonwinterto


Images courtesy of Madison Winter

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Madison Winter

Madison Winter, Canada's self-proclaimed 'girl next door' is a high-end companion who lives and works out of Toronto, ON. She's left a career in finance to become a provider, and now specializes in long engagements and relationship-based dates. In her spare time, she's usually collecting passport stamps, or at home with her two dogs jamming out to 80's rock.

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