Author: Madison Winter

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

Like to be featured on SimplySxy? Drop us an email at editorial@SimplySxy.com!

January 2, 2020
How To Select An Escort For The First Time

I tend to meet a lot of first-timers. That is, gentlemen who have never been with a companion before. I’m always incredibly honoured not only because they chose me for their first date, but that I have the opportunity to introduce them to this wild, wonderful, and complex world.

Nerves is almost always an issue, but it’s not always exclusive to first timer gentlemen. It’s relatively often that when I’m meeting my date for the first time, it’s apparent that he has spent a lot of time anticipating, imagining, and sometimes stressing about our encounter.

Is It Normal For First Timers To Feel Nervous?

Absolutely, first date jitters is completely normal. Given the nature of our encounter, I understand the source. Not only are you meeting someone that you’ve likely admired from afar for months (which is nerve-racking in itself), the stakes are high!

There’s a significant investment on the client’s part, which I try not to take for granted. He’s investing his capital, of course, but also a chunk of his time that’s irreplaceable. In addition to both of these things – there’s also the anxiety provoking stereotypes about escorts that first timer’s sometimes have in the back of their mind. Is she enjoying herself? Is she here because she wants to be?

I encourage my clients to remember that these thoughts are normal and valid. You’re about to enter completely new territory, and your body is reacting, physiologically speaking, in a normal and expected way. It’d be amiss if I didn’t mention that If something feels off, acknowledge that. If there are red flags, take note of them. We should both be doing this in the days leading up to our encounter.

That being said, don’t underestimate the importance of research, and ultimately, trusting your provider. You’re in good hands.

Importance Of Choosing A Good Escort For Your First Time

Researching your provider, and the industry that you’re about to dabble in is important, and comes in various formats.

Firstly, you can peruse various advertising platforms. It’s not just about photos. I always advise reading numerous provider’s copy – their website, and bios. What resonates with you? Who leaves you curious, and wanting more?

Does this provider have social media? Do they promote themselves in a way that’s attractive to you? Do you have similar interests – is your intrigue mounting? Furthermore, do you sense a level of professionalism? Does she appear to have a verifiable reputation?

I think it’s necessary to remember that while physical attractiveness is of course important (and subjective), try not to neglect emotional attractiveness. A name and a photo won’t give you clues about the kind of person you’re meeting, and the experience you’ll have.

My best clients are the ones that paid attention, and did their homework. They read my website in its entirety, took note of my likes and dislikes, followed me on social media, and eventually got to the point where their gut instinct was: “we’re going to get along.”

How A Good Escort Can Calm A Clients’ Nerves

I think a good escort is somebody who has a high level of EQ, and a high sensitivity for empathy. Most of us in this business got into it in the first place because we adore fostering connections. She’s here because she understands people, and all the idiosyncrasies that come along with them, nerves included.

Chances are, we already know you’re nervous.

The beauty of this business is that all of us, while similar in some ways, operate in a completely different fashion. My approach when meeting a nerve ridden client is to somewhat ignore the problem. I personally find that hyper focusing and dwelling on nervousness isn’t the most effective.

Also – I treat my dates like any other first date. We’re here to get to know each other, and we’re both a little nervous. I try to be authentic, transparent, and give genuine compliments if they’re due. I’ll ask thoughtful questions and give you my honest opinions.

As the night progresses, your shoulders might lower, your jaw might unclench, and we might find ourselves laughing and flirting. Usually before the evening’s over, we’ve found a way to connect in a real and sincere way, and all of a sudden, the nerves that we both felt at the beginning are no longer an issue.

Last Tips For First Timer Clients

My biggest tip: trust her.

Nerves are normal, and totally ok. However, that chemistry you’re feeling? It’s very real and palpable.

Try your best not to let anxiousness, self-doubt, and internal worries override the experience you’re having… because it just might turn into something wonderful.

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

Like to be featured on SimplySxy? Drop us an email at editorial@SimplySxy.com!

November 15, 2019
How To Be An Escorts Favorite Client

I’ve been in this industry for 13 months, and it was the best decision I ever made. Like most, I had no idea the business existed. I simply assumed that my male colleagues had long lunch meetings.

The more time I spend in this business however, the more genius it seems. Both the client, and the escort gain from their arrangement. I get an opportunity to explore my sensuality, and am paid to have stimulating conversations, and try things I’ve always wanted to try anyway. My client, gets the opportunity to be unjudged, appreciated, and ravished.. then sneak back to his regular world.

Typical Clients I See

A huge misconception of men who see escorts, is that they’re seedy, unsafe, or crooked individuals. This is entirely the opposite. The mass majority of my clients are white collar, educated, even attractive gentlemen who treat me like gold. I see real estate agents, graphic design artists, doctors, senior finance professionals, and more.

Tips To Be My Favourite Client

Escorting, like any job, requires the worker to feel appreciated and valued in order to keep working. Many clients don’t realize the many hats we wear, and how much time, money, and emotional energy we spend making ourselves the perfect companion. It’s sometimes physically and emotionally exhausting.

My favourite clients, are the ones who get it. They treat me with respect and dignity, and show ample appreciation. That could mean basic things such as leaving on time, and investing a few minutes of our date on conversation.. to more extravagant things such as tipping or bringing a small gift.

I’ve had new clients show up, and dash to the shower without so much as a hello, then expect intimacy immediately after. Granted, that is the jyst of what a client is paying for, and I understand that. However, nothing makes you feel more like a blow up doll than obvious disinterest in you as a person.

Madison Winter – Consider me your approachable, yet classy girl next door. I love nothing more than sharing a meal or glass of red wine over stimulating conversation. Let’s unravel the layers of each other; I really love to take my time exploring… Cant wait to discover you.

Follow me on:

Website: http://www.madisonwinterto.com/
Twitter: https://twitter.com/MadisonwinterTo

Images courtesy of Madison Winter

Like to be featured on SimplySxy? Drop us an email at editorial@SimplySxy.com!

July 15, 2017