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What To Do When Seeing A Courtesan For The First Time

Sex Ed

What To Do When Seeing A Courtesan For The First Time

At any rate, allow yourself to expand your definition of sex. Relative to my peers, I stumbled late into the party and much preferred to hang out by first-floor windows for less-than-erotic escapes. My early university years proudly presented sex in all its glory. It wasn’t until after I popped my cherry out of much pent-up sexual frustration and making the call on a pricey Brazilian (wax) that I began to draw on what it meant to me to feel desired.

In allowing myself to first get deeply personal, I found what turned me on increasingly more enjoyable. Teasing neck bites in-between the pillows could cast the same frenzy as holding a hushed conversation inches from a stranger’s ear at the bar, well-wrapped up around their thumb. It won’t be the last time you hear it, but for all my firsts out there, know this: a climax cannot be appreciated without breaking a sweat, working out the kinks of foreplay.

How Are First Timer Clients Like?

My first timers are some of the sweetest nuggets out there. They constitute a little less than 15% of my reach who also book. They’re drawn to the playful humour and sly wit they see online and I think show up with just the faintest hope I’ll use it to help quell their nerves in person. They also send the best memes. Hands down.

I’d be naïve to think I could speak for all companions or sex providers (SPs). I find, however, that my first timers either ask all the questions or none. Experienced patrons can be no different but also include ‘not enough’ despite knowing better, you’d think. Our latter group here is not necessarily immune to mounting nervous energy either. It is, after all, a real date.

As with any real date, respectful, non-pushy use of language before and/or during this encounter involve understanding that requesting ‘menus’ right off the bat is off-putting to some SPs, including myself. With first timers and experienced patrons alike, I actively work to normalize effectively communicating boundaries to build an initial sense of trust in these sessions. Listening here is the power move. Both groups typically understand consent once raised—at least, in my experience. I cannot emphasize enough that consent is best expressed verbally by all parties involved to not shoot the mood for the evening. For our readers asking, ‘what if…’, I garner that you’re both adults—an email exchanging written confirmation of consensual acts beforehand is a green-light technicality.

When the door opens, there are a few from both groups that don’t seem to know what to do with themselves and I’m reminded of myself. I find it charming. I’d say I’m quicker now to Shepard’s crook them by the belt holes before they bolt—assuming I’m hosting, of course. Given the sound of room service trolleys fast approaching anywhere, I’ve never been all that slow or shy to lift a few jaws on the walk in. This is only a subtle reminder to have your Do-Not-Disturb signs ready in hand, gents.

Preparing For Your SP Before She Arrives

Prep has got to be half the fun. It’s highly likely the SP’s given you a little reading material for the nights you’ve been sitting up in bed, still awake in anticipation.

Work knocks you out good? Yeah, you can catch their Tweets on your commute to work or in an unassuming corner of the office during your lunch break. The most logical order IMO is starting with the website. Read it proper. If you’re not sold, or just want more than you’d like to admit, hit up the Media section on their Twitter—especially if you’re more of a ‘visuals person’. Then take a moment to check their Likes section to see if they’re still sane enough for you.

Confirmations—along with a complete form submission—can be very important for many SPs. This may include a deposit, which you’ll have made note of if you’ve read her website (proper). Confirm at least the day before. I would advise against looking to confirm more than twice for any date as unnecessary persistence begins to raise yellow flags.

If you’re working with a longer date, be considerate and well-prepared to offer them a bite (check for allergies, nutter butt) and glass of water at least. Drink some yourself. While you’re at it, moisturize your lips and tend to all grooming and hygiene needs. A little rinsey rinsey under the sink faucets would be most unwise. Even I’d pray for you. If the SP appears rather vocal online, do yourself a favor and don’t let yourself be sub-tweeted at. Tend twice to any areas you’d like to be appreciated.

Be mindful to have the compensation ready for them in an envelope or whatever means they’d prefer. Location-wise, it should be in plain sight. You can’t mess this instruction up—it’s my easiest one. Tidy up the place if need be and upon offering to take their coat past the door, kindly also direct their gaze to said patronage along with some direction to the nearest bathroom. I’ll add that this is part of the foreplay I stressed earlier. Though I don’t know you, reader, I do want you to have an amazing time nonetheless. Do as their websites instruct you. Waiting to present their compensation till the end leaves many slightly more reserved in session. The wrap-up at the end is actually a window better suited to tips. On tips, I would say if you have the means to be generous and truly enjoyed your time, prepare this while they’re showering. Even if you’re not tipping, do the decency of giving them the privacy to get ready in there alone. Trust me on this one too. I gargle often and spit facts.

Though not necessary, try to have a bottle of mouthwash, fresh bath towels and a neutral or relatively less ‘masculine’ smelling body wash available for their use at the end of the date. Your SP will appreciate it and not use your liquid hand soap by the sink. Should you fail to do so, don’t comment on how ingenious [she/they] smells.

Once The Meet Up Begins…

You’ve prepared yourself well! Assuming you read most of my last bit. The excitement’s got to be near through the roof at this point, I’ll bet.

I hope you both have a lovely little or long time together. Don’t know what that entails? Did you plan a theater outing together? Holding hands doing nothing? A couples mani pedi before your kink dungeon date? Snakes and Ladders, maybe? An indoor board game atop a new and *very* doable cuddling position? Or was it erotic wrestling? A home-cooked meal for two? Or season two of some genius Netflix realm while you practise your rope basics? Well, why don’t you ask them…?

Ways To Ease Nerves For A First Timer

As if I haven’t been already, this will be a space to be blunt. To engage earnestly with your SP and in more of a wholesome manner at that, do not excessively drink and/or abuse substances to ‘escape’ your nerves prior to your meeting, gentlemen. Even your boss could tell you that. If you’re your own boss, I just did, so have your delusions call my people, if you so must.

Second, read as much as want about your provider until you think you’re ready. This will still not mean you’re actually ready for whatever you’re expecting. Dates may flow every which way and controlling the stream too firm with expectation is a harder take than necessary; you could guarantee a flop. Be present and trust your SP. True intimacy is rooted in that initial trust.

Third, I’d like to separate this little bit of advice about trusting yourself. You have no one to be but yourself on this date. Feel no need to overcompensate or tear yourself down. Unless, of course, that’s your kink, then you will need to express this to your SP before the date to not make things awkward. Communicate what space you want or need with your SP verbally. This could mean starting the date seated across/next to each other and draw yourself closer as you feel more comfortable with each smile. Meet anxiety with some eye contact and a little willingness to laugh in the face of it.

First Timer Etiquette Tips 

My advice for etiquette lies on and in-between the lines I’ve provided above. Everything said pertaining to hygiene, surrounding misc. preparations, and pre-date exchanges are very important. Be on time but don’t be one to watch the clock, that goes for SPs and patrons alike. Leaving on time is major, too. Overstaying your welcome or holding an SP from having to leave is a faux pas, meaning don’t you dare do it. I would also emphasize making sure to brush up on safe sex practices and communicating with your SP that you understand them.

Once the date has started, try to keep your reservations at bay and tune into your newest muse. Feel no pressure for anyone to claim to have climaxed two minutes of walking through that door. Most likely, this will be a mutual feeling for your SP. The real takeaway will be in how well the both of you listen to each other during foreplay. Come as your best self. Be ready to be open and/or equally ready to listen. Have fun!


Léa Rose – Seemingly yet another self-proclaimed high-end companion to the Rose kin, this pun-lovin’, long-limbed lynx reckons you’ll be inquiring more about her writing outlets and phon-atic musings at some point or another. Often tuned into a different frequency having secured her travel bag with a bit of head start than most, she’s a millennial milking every bit of having to stay stagnant living and working in the ever-growing metropolis that is Toronto, ON.

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Website: hellolearose.nl

Twitter: twitter.com/HelloLeaRose

Curious Cat: curiouscat.me/HelloLeaRose

Having successfully just wrapped up her 2020 tours of San Francisco, Los Angeles, and Houston, you can catch Léa shimmying somewhere in Boston, New York City, Las Vegas, Vancouver, Montreal, Ottawa, Edmonton, and Calgary next.


Images courtesy of Léa Rose

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Léa Rose

Léa Rose, Seemingly yet another self-proclaimed high-end companion to the Rose kin, this pun-lovin’, long-limbed lynx reckons you’ll be inquiring more about her writing outlets and phon-atic musings at some point or another. Often tuned into a different frequency having secured her travel bag with a bit of head start than most, she’s a millennial milking every bit of having to stay stagnant living and working in the ever-growing metropolis that is Toronto, ON.

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