Prologue

I’m Charlie, a pilot with one of the largest US airlines. It’s been a while since you heard from me, but I finally managed to track down the mysterious stewardess who dropped her salacious diary in my carry-on over a year ago.

Her name? Sophia Andrews Vasquez.

She no longer works for my airline, having moved on to greener pastures of sorts, both career- and relationship-wise. Sophia now runs a whorehouse in Paris (which she calls a maison close), and she’s in a complicated relationship with a talented Spanish painter named Virginia, who goes by the brush name of Valentina.

These two special ladies have extended an invitation for me to court them both, but that’s easier said than done. I’ve recently gotten to know Virginia intimately (so I know which buttons to press there), but my knowledge of Sophia’s likes, dislikes, turn-ons, and turn-offs is patchy at best.

What I do know comes from my encounters with the parties mentioned in her original diary while tracking her down. The other details included by Sophia in her journal also helped but weren’t enough to tame my obsession in the flesh last time. All I got was a kiss from her, but it was by far the most magnetic, passionate, and breathtaking kiss I’d ever had in my life. I can’t stop dreaming about her multi-colored irises, her curvaceous body, her velvety voice, her delicious lips, her irresistible jasmine scent. I can’t even come up with a word powerful enough to describe my expectations in terms of what sex with her will feel like.

Brain-explodingly astonishing?

Or perhaps dull as fuck, but I highly doubt it.

Based on the detailed tales I’ve read about her and the videos I found, sex with my no-longer-mysterious ex-stewardess will blow my mind.

It’s something I look forward to. Something my mind defaults to every night as I fall asleep. Something I picture every morning as I release my fantasy-induced pressure in the shower.

My obsession with Sophia has taken over my life, and it certainly won’t disappear until I’ve courted her and brought us both past our mutual orgasmic thresholds. Possibly along with Virginia. That would be quite the powerful trio. I hope it happens. Soon.

To help with my new objective, I now possess two new diaries. Tacked to one of them is a yellow Post-it note urging me to not take any entries personally.

Duh. I get it.

Diaries are—by definition—repositories of unfiltered thoughts, meanderings, and first impressions. Their contents could, of course, be misleading, but the words they chose had to be my ladies’ honest truths while they experienced whatever was worthy of a diary entry.

So, I’ll read their raw words and let whatever hurtful comments slide off my back. With more than four decades of practice doing so, I’ve become an expert at not caring about what others think.

I’m eager to dive into Sophia’s and Virginia’s hand-written accounts of what happened to them over the past year while I was busy tracking down Sophia. But the bulk of Virginia’s diary is in Spanish, so it’s forcing me to bring out the dictionary and translate her words as I go along. My Spanish gets me through basic conversations, but glancing at her first entry had me confused and entering words into Google’s online translation tool.

To further complicate things, some of Sophia’s diary entries also contain French. I’ve committed to learning that tricky language (so my application to her whorehouse can be approved). I can’t wait to try Sophia’s in-house delicacies: top-of-the-line escorts offered in a private château-like environment.

You must think I’m a fool for getting excited over the prospect of sleeping with other gorgeous women when my goal is to court Virginia and Sophia. To make them both fall head-over-heels in love with me, to be exact.

Maybe I am.

But my women haven’t specifically requested exclusivity out of me. They aren’t even exclusive with each other, as far as I can tell. Otherwise why would Virginia have slept with me last year—and repeatedly so, might I add?

Truth is, I know why Virginia couldn’t resist. I see myself in the mirror every day. I’m a charming guy, and my job has its own panty-dropping qualities. (Uniforms sometimes have great perks, don’t they?) I’m a ladies’ man, and I’m damn good at it. But I digress.

Getting back to my potentially foolish side quest, Sophia is the one who handed me the application to her maison close. It would be rude of me to not take her up on it (and no single, heterosexual man on earth would turn down the opportunity I’ve been handed).

But there’s lots to do before I can make the world’s best threesome with Virginia and Sophia happen. My looks and smarts have gotten me to where I am today, but I’ll have to work on my language skills and learn more about my ladies if I want to reach my goal.

So I bought myself (very thick) dictionaries, and I’ll keep them by my side as I read the diaries and the complicated application form I have to submit to gain access to Sophia’s fine establishment. Because first impressions count for something (and because I can’t understand their entries at first glance), I haven’t pre-read my ladies’ entries this time. I’ll be reading them in the coming months, writing down my thoughts and journaling about my actions as I go along.

I don’t know how long this process will take, but I’ll do my best to break my ladies’ diaries into small, digestible sections. Possibly ten, like last time, but there’s no guarantee. I’ll learn what they went through over the past year. Then, when it makes sense to do so, I’ll pause to digest the information and share it with you.

I’ve got no idea if I’ll get to travel as much this time around, or if I’ll simply call them every now and then to check in (I sure hope for the former). Their written words will help me catch up on whatever large fight they had—which yours truly superbly resolved.

I’m looking forward to reading the most private details my two special ladies have shared with me, even though I didn’t ask. Their respective diaries will likely contain information I’ll be able to use to win them over.

So in order for you to not miss out on any valuable insights I’m sure to uncover, you’ll find Sophia’s translated entries followed by Virginia’s—which include sketches. As I’m not an artist, I’ll just describe them for you. I’ll then include my post-read evaluation of what I learned and bring the story back to today’s timeline (a year or so after my ladies’ journals were written).

Since I don’t expect their stories to be as self-contained as last year, I’ll also include a brief Too Long; Didn’t Read (TLDR) section at the beginning of future episodes so you can refresh your memory about what happened last time.

To be clear, these stories should not land in the hands of any prude or underage person. If my ladies have taught me anything, it’s that their diaries are sure to contain juicy details about their sexual encounters and other hidden treasures I’m eager to discover.

I’m hard just thinking about it.

Yours truly,

Capt. Charlie

Undisclosed Airline

P.S. If you want to read Sophia’s complete letter, you can download it for free here: https://www.smpratt.com/dear-charlie-season-two

P.P.S. This isn’t the same letter as the one she gave me with the application for her maison close when I met her in person at the airport in Madrid. Yeah, I know… The woman likes to write. A lot. Pen on paper seems to be her favorite mode of expression—along with hot bodies rubbing against one another, of course.

P.P.P.S. This story follows an episodic novel called The Stewardess’s Diary by the same author. Although you can jump in right here (I summarized all the important bits above), I still recommend you read through our previous adventures to better understand the nuances of what happened last year. Learn more here: https://www.smpratt.com/the-stewardesss-diary/

***

The Stewardess’s Diary – 10:00 a.m.

It’s been three weeks.

Three long weeks of not hearing her voice. Three weeks of biting my nails and doing everything I can to not contact her or be too pushy. I haven’t even kept my diary to avoid thinking about her.

But my efforts were all pointless.

Virginia has carved herself a permanent spot in my mind and in my heart.

Ah, the number of times I picked up the phone and almost dialed her number.

Definitely in the two-digit range. Twenty? Thirty?

Was something wrong with me?

Why couldn’t I tap Call when I brought up her number?

While Spain was several hours ahead of New York, Virginia would still have been awake on most of those occasions.

She should be done with my portrait now, right? This would be a legitimate reason for me to contact her without looking too needy…

Or maybe not.

If she wasn’t done, I’d look needy.

But the fact that she hadn’t kissed me at the airport still haunted me. No matter how many times I asked myself why she hadn’t done it, or how many times I tried to relive the experience from her perspective, the only conclusion I could come up with is that she didn’t want to keep the relationship going.

Relationship… Or whatever she called the thing we were having.

A fling? Holiday with benefits? Or just a regular series of painting sessions with a new model?

No matter the name, it was over. And that was a real shame.

Since she’d made absolutely no effort to stay in contact, her previous statements about how much she despised commitment held true.

Well, so much for my initial plan of keeping our relationship going.

The only thing I could do had already been put in motion. Moving to Paris would be a start, and I could travel to Spain regularly if she wanted to see more of me. But my hopes were as dim as dusk.

After three weeks of nothing, it was pretty clear where she stood. There was only one solution: I had to forget about her.

So I went back to writing down my thoughts and recording what was happening in my life, hoping that it would somehow exorcise her from my mind and soul. But thinking about her while writing those last few pages had made my heart beat with gusto, my cheeks flush with desire, and my pussy twitch with expectation.

But my bodily reactions didn’t change a thing. I simply had to move on and focus on something else.

Nicholas!

I looked at the clock to figure out what time it would be for him in Paris. Totally acceptable for me to call him now. In fact, he should still be in the office if he didn’t have appointments with clients.

After three of the familiar international ringtones, Amélie’s voice greeted me.

“Hi, you’ve reached the office of Maître Nicholas Lancelot. How may I help you?”

“Hi, Amélie. It’s Sophia Andrews Vasquez. Any chance I can speak with Nicholas?”

“He’s not in right now. Do you want to leave him a message?”

“Sure. Please tell him to send me information on how to get a work visa, so I can begin to plan my move to Paris.”

“Ah,” she said, her tone sounding more annoyed than pleased.

Assuming she was writing something down, I kept quiet during the pause that followed, although I could totally picture the annoyed expression on her pale face.

She’s never liked me. I’d bet anything on that.

“Do you know when he’ll be back?” I asked after a delay so long it had me wondering if she’d left the receiver unattended or if the line had stopped working.

“Tomorrow morning. I don’t expect to see him in the office before I leave today.”

“Okay then. You enjoy the rest of your day.”

She hung up without further ado, skipping the courtesy of wishing me a good day in return.