Introduction
Welcome to Train Vacation, a fictional five-part series featuring Alistair and his wife Jennifer. They are members of DESERT FANTASIES, an escort service. The membership provides an avenue for the occasional role play. They have made it clear that Jen’s escort services were available to only one client: her husband.
Both she and Al are adept at role playing. This time, Jen decides to kick it up a notch by acting the overall role of a client instead of escort. Within the larger role of client, she kicks things up further, switching her roles or personality multiple times within a single larger event, without warning. In this case, the single larger event covers multiple days. To some degree Al is not sure whether the woman with whom he ate supper is the same woman in his bed that night or whether it’s a different woman again at breakfast.
Note for readers: Throughout this series, blocks of plain text indicate Al’s point of view, while italics indicate Jen’s perspective.
Prologue
The phone rang a few times, then a female voice picked up on the other end. “Good morning, Desert Fantasies. This is Samantha. Thanks for calling. How may I help you?”
I hesitated momentarily. It had always been Al who called the service to set things up. Taking a deep breath, I calmed down. “This is escort 523. I have a message for client 1723. I will be making reservations for him and sending tickets for a train vacation.”
“Any special instructions I should pass on to him?”
“I’ll send them to you over email. Please forward them to him.”
Train Vacation – Part 1: The Escort
I noticed the arrival of a text message notify me that I was to call the escort service. I was a bit curious why they might want to talk with me. It had been months since Jennifer and I had used it. My morning coffee break was the first opportunity to call.
“Good morning, Desert Fantasies. Thanks for checking in.” Candy told me that I had been scheduled to as an escort, and read off the dates over the phone. “Is that going to work for you?”
“I’ll have to adjust my schedule a bit, but it’s not a problem,” I said. “Anything else I should know?”
“She left instructions, which I’ve sent to you as an email.”
“Anything else?”
“If you have a moment and don’t mind a question or two…?” Candy asked hesitantly. “About some of the notes she left here…”
I knew which notes she was talking about, left there the previous adventures Jen and I had experienced through Desert Fantasies. With a smirk, I said, “I believe those are ‘private matters’ that I can cover with my client. No need to discuss them now. Thank you for the call, and have a nice day.”
I hung up the phone, leaving her to blush at the thinly-veiled notes about raunchy sex acts.
I checked my email to see what kind of sexy instructions my “client” had left for me. Apparently, she had planned quite the adventure:
On Monday, my chauffeur will pick you up at your home and take you to the airport. My company’s jet will fly you to the departure point of our train vacation.
On Tuesday, you are to go to breakfast in the train’s dining car. I will come fifteen minutes later. I’ll be wearing a plaid shirt. A bit tight. Untucked. No skin showing. Comfortable jeans showing signs of wear. I’ll make the impression of a sweet innocent country girl, greet one or two diners, then make a show of undoing several of the buttons. With one button missing, there will be only two holding things together. I’ll look more like a slut than a school girl.
I will come to your table and drop a penis pendant fastened to a delicate necklace. You will respond with a lewd remark. It will be the start of verbal foreplay. I will act offended. Somewhere in the course of our interaction, I will grope at your erection—discretely of course. On my way out of the car to my compartment, I will stop, turn, and flash a full frontal.
– Your slut client
Monday
My client (Jen) had described her company’s business jet on a previous vacation we had shared. The description didn’t prepare me adequately for what I encountered as I stepped on board. The cabin could rival the suite of a 4-star hotel: leather seats, flat screen TVs, and a mini bar. And it appeared there were no other passengers on board either, so I had it all to myself! Well, there was the flight attendant, of course. She actually looked strangely familiar, but gave no sign of recognizing me.
The flight attendant stowed my carry-on and helped me with my seatbelt. I pulled out some reading material as I settled in, then immediately jumped as the attendant started rubbing my crotch! Odd. How had my client arranged this? Regardless, neither I nor my cock complained.
Stopping abruptly, she jumped up and removed her hand. “We’ll be getting airborne shortly. Sorry to leave you ‘high and dry,’ but madam would not approve of me ‘attending to your comforts’ like this. Have a nice flight. Your client will join you after we’re airborne.”
Again, odd. Was I to take care of things myself?
My seat was one of those that recline fully, I settled in for a nap and fell asleep.
What felt like just a few minutes later, I woke up staring into the crotch of a woman’s tailor-made, navy blue slacks. Her crotch and mound must have been only a few inches from my eyes. Looking upward, the dark red blouse also appeared tailor-made. It fit her perfectly, clinging tightly around the two globes of her very female body. I caught a fleeting glimpse of flesh through a small gap between the buttons. My cock was quickly waking up as well.
The pronounced peaks of her nipples poking into the blouse made it difficult to look up at her face, but from the glance I got, she was definitely my client. Funnily enough, she looked a bit like the flight attendant, who had disappeared somewhere.
“Are you a member of the Mile-High Club?” she asked.
“Mile-High Club?”
“Six miles actually. Sex at thirty thousand feet.”
A memory popped into my consciousness. One from another flight. “My seat mate gave me a hand job once. Does that count? She invited me to her hotel room during my eight-hour layover.”
“No.”
“Then I guess not.”
She unfastened my seat belt and said, “Follow me.” She led me through another door to a suite with a king size bed. “This will be more comfortable.” After making sure the door was securely closed, she sat on the edge of the bed.
“Come.” She started to stroke me. “Today will be more than a hand job or a blow job. First, I’m going to watch you take your clothes off.”
I had no intention of objecting.
She continued giving instructions: “I want you to suck a hickey on my right boob. Take all the time you need. Grope the other if you like. Or anything else, if that’s your thing. Except my pussy. Then I’m going to ride you.”
I was proud of the purple splotch I gave her just above and to one side of her right nipple. I would liked to have sucked one on the other breast too, but my client seemed anxious to climb on in a reverse mount. The plane flew into some turbulence. It resulted in me not having to work so hard at thrusting myself into my client. Several times she came down quite hard, driving my penis deep into her. While disappointed that I couldn’t watch her bouncing boobs, I enjoyed the workout my cock was receiving. She started screaming when another set of turbulence buffeted the aircraft, but I don’t think she was screaming out of fear.
As she rolled off of me, I pulled her left breast to my mouth and slid my hand between her legs. She swatted my hand away with a sharp reprimand. Oh well. She was the client after all. Perhaps her pussy had had enough. Or perhaps she had some urgent business needing her attention. “I’ll send the flight attendant to escort you back to your seat.” Then, snatching up her clothes—and without putting them on—she scampered out of the bedroom.
I was shocked at first, but then wondered if that might be normal on these flights with almost no one on board.
Moments later, the flight attendant from earlier greeted me—topless.
I hadn’t even had a chance to get dressed. Did she notice my erection? How could she not? If she did, it didn’t seem to bother her. She escorted me back to my seat and made sure it was in the full upright position for landing. I expected she would be fastening my seat belt next. She leaned over in front of me, but hesitated a few seconds before continuing with her duties.
“They please you, no?” she asked hopefully. To emphasize the question, she cupped both boobs in her hands and twisted her nipples. Maybe she was hoping to get some too, regardless of whether madam approved. “Madam apologizes for…” She paused, searching for the right word. “…for her abrupt departure. But she says you like breast play.” She lowered her hands to mine and brought them up. I was beginning to wonder what my client was up to. “She says you like this too…”
In one slow, languid movement, she knelt, spread my legs, and popped my erection into her mouth. And she didn’t slap my hand away when it started to slip up under her shorts. Her tongue was wonderful. Smooth. Silky. Experienced. Successful. At least this time, I caught glimpses of magnificent breasts while her head bobbed up and down on my shaft. And now that her hands had stopped cupping her breasts, I recognized a very fresh-looking hickey next to one breast.
Did I mention my client was a master of disguise? It was a bit of an odd thought to pop into my brain, just as the flight attendant and I were cumming. But even though I was occupied enjoying the beauty of her boobs and the pleasure of my fingers in her cunt, I couldn’t help remembering that bit of trivia.
I told you she could kick it up a notch.
To be continued in Part 2.
**********
Here are a few other related roleplay stories!
Nurse Jen (August 23, 2022)
Conduct Unbecoming (December 8, 2022)
Overnight Service (January 10, 2023)
Playing with Matches (February 26, 2024)
Letting Go of the Reins (May 11, 2024)
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