Around the World with a Stranger Pt. 01

This story is inspired by a real event. A couple split up, but they had this elaborate trip booked. The man didn't want to give up the reservations for the fantastic voyage they had planned, so he posted an online ad looking for women who shared his ex-girlfriend's name and a valid Canadian passport. Several women answered; one was selected to join him on his trip. The news media did several human interest stories on their trip together.

The rest of this is the work of my own imagination and fantasy. I changed the travelers' names and destinations. This in no way is an account of what occurred between the two actual people involved: it is fiction. It starts out a little slow, so if you're looking for quick release, you will probably need to look elsewhere. But if you stick with it, I'd like to think the payoff is immense.

MF, MFF, Exh, Voy, Mast, Int.

Chapter 1 - My wedding and honeymoon are destroyed

"That bitch has broken my heart," I thought as I read the email from Jane. A fucking email! She calls off our engagement and our wedding in a fucking email! I guess I should have seen it coming, but I wasn't expecting this. Jane and I had our problems, but I honestly believed we could work them out. I loved her and wanted to marry her and spend the rest of my life with her. I thought she felt the same, but apparently not. According to her, I was "too busy planning things" and "was too wrapped up in my own notions and set unachievable expectations of even the simplest things". She didn't want "to have her life micromanaged." She wanted spontaneity and I wasn't the guy. It would have been nice to know how she felt before she agreed to marry me, but there you go.

I called Jane, begging and pleading. She wouldn't budge. I told her I could change. She said she didn't think so. Finally I got angry with her and called her all the worst names I could imagine, and said all those hurtful things I had always kept to myself for the past three years. This put the final nail in the coffin of our relationship. We left it with her saying she was going to move on and that she never wanted to see me or hear from me again.

So there I was, sitting in my condo downtown, my heart in tatters. I felt numb as I began calling and canceling things for the wedding (which was supposed to happen in two week's time, November 1st) like the DJ and the reception hall. I also had to field calls from friends and relatives, trying to explain why the wedding was off. I had to return wedding gifts that arrived in the mail. Frankly I was upset that I had so much to do (on top of work), and that she was taking no responsibility for dismantling the apparatus of our wedding.

Then it came time to cancel the honeymoon. She had gotten to plan the wedding (with a lot of input from me, admittedly), but the honeymoon was my baby.

We were supposed to be gone for a month. I had scrimped and saved and had about 18 large tied up in our grand adventure. Our itinerary included 2 weeks in Europe and 2 weeks in Southeast Asia. We were supposed to hit Paris, Rome, Venice and Florence, then fly to Hong Kong, Phuket and Bali. I had booked the best hotels, activities, tours and relaxation days. It was supposed to be the trip of a lifetime, but then Jane went and destroyed me and ruined the trip. I sat there thinking about how hard I had worked and how many sacrifices I made to save the money, and how much effort I had put into the planning. I couldn't do it; I couldn't cancel the trip.

At the same time, all the hotel and activity bookings I had made, not to mention the 10 sets of airline tickets, were for two people: me, Martin Lockwood, and my ex, Jane Tillson. With 13 days until our scheduled departure, I began calling airlines to see if I could switch Jane's ticket and give it to my best friend Charlie. Three airlines said yes, but four said no. I called up my travel agent Sunita (with whom I had managed to become good friends over the past 4 months of planning) and explained the situation, and asked for her advice. "How do I go on my honeymoon with someone who is not Jane?" Sunita thought about it for a moment, and then stunned me with her answer.

"Easy Martin, you go with another Jane. As long as her name is Jane Tillson, and she has a valid Canadian passport, you can go and not lose any money."

My mind raced as I considered the possibilities:

"I will still be able to go..."

"See the piazzas and canals..."

"The Colloseum..."

"...galleries..."

"...beaches..."

"With a stranger."

This brought my mind to a halt. Sunita looked at me, and as if reading my mind, said "Yes Martin, if you want to take your trip and not lose any of the deposits and all the other fees you have paid up to this point, unless you know someone else named Jane Tillson, you will need to find someone you don't know to join you."

"Is there no other way Sunita?"

"Not that I can think of. I'm so sorry to hear about you and Jane, and the situation you're in right now really sucks, but your only options at this point are to lose roughly 8 grand or to get a stranger to accompany you."

The only other Jane Tillson I knew was Jane's grandma, a 75 year old woman living in a palliative care facility. She wouldn't be able to make the trip even if I wanted her to come (which I didn't). I thanked Sunita for all she had done, and left with the gears turning in my head.

Chapter 2 - I find another Jane

The ad I posted on Reddit said, "ISO a girl named Jane Tillson who is seeking adventure. Must have a valid Canadian passport, must be named Jane Tillson, and must be free to travel from November 2 to December 3. My fiancée called off our wedding, but I still want to go on our honeymoon. If you're interested in visiting Paris, Florence, Venice, Rome, Hong Kong, Phuket and Bali with a guy who's just had his heart broken, please respond to this ad. The flights and hotels are all paid for. You would be responsible for your food and other expenses. This is not a joke."

I didn't know what to expect in response. Twelve days until I was supposed to fly out of Toronto Pearson airport for Paris.

I checked my email constantly that first day: I was disappointed to only receive two responses. One from a lady name Jane Tillsonburg, who sounded nice but wouldn't fit the bill, and one from a hooker who said she could be whoever I needed her to be, and it would cost me $500 per day plus expenses for the full "newlywed" treatment.

I was dejected. Charlie came in on the train from the suburbs and took me out drinking. That night I drank way too much and puked in the cab on the way home. I was miserable.

But God bless Charlie. I told him about the trip and what Sunita said, and the Reddit ad. Later that evening, on the train ride home, he tracked down my ad and tweeted it out to his 650 followers. The next day it went viral and my ad went from 28 views to 25,873. It was generating a lot of buzz and the emails started rolling in.

I received about a hundred emails, including messages from 30 different Jane Tillsons in Canada, and a couple media requests. I was able to filter out all the non-Janes and replied directly to the Janes, explaining the situation in a bit more detail, the trip itinerary and answering their questions. I was also being cautious and asked each Jane to send me a hi-res picture of them holding today's newspaper and their passport so I could validate they were who they claimed to be. Over the next couple days this eliminated 10 applicants, while another 8 new ones rolled in. I was also interviewed by a reporter from a Toronto daily newspaper.

I could tell by the emails I received the Janes who might be suitable travel companions: if one could not spell or form a cogent sentence, or if they seemed flaky or evasive, they were out. Since some of the planned activities were "extreme" like rock climbing and parasailing, not to mention all the walking we would be doing in Europe and Asia, I was inclined to eliminate women over 40. I was going to be spending a month with this person, so I wanted to be sure we would have something in common, so I eliminated girls that were too young, or had kids.

My list of 28 Janes was whittled down to 3 within the next day. To each of these Janes, I sent pics of myself, a copy of Jane's email and the travel docs and plans. I arranged to FaceTime each of them.

I had a pretty good exchange with the Jane from Canmore, a disastrous exchange with the Jane from Toronto (her expectations were out of sync with the trip I had imagined in my head, and she also accused me of being a stalker) and a great exchange with the Jane from Kelowna. It also helped that Kelowna Jane (or KJ as I called her) was an active, attractive 23 year old. Ultimately, I was leaning towards KJ because we got along in our email exchanges. I told the other Jane from Canmore that it was great talking to her, but I had decided to choose someone else. Immediately after talking with her, I received a call from the guest booker at Wake Up and Have Breakfast TV, who invited me to come on the show in the morning to tell my story. The Toronto Daily News also wanted to do a story on me if I was able to successfully find a Jane, and they wanted to send along a photo journalist and their travel writer to meet us at a few of our destinations. Both people who called me told me about all the buzz my story had generated up to this point. It got me excited as well and I told them about KJ. The booker for the TV spot wanted to know if KJ could join us on the show tomorrow morning via phone. I said I'd ask her.

I face timed KJ again and explained that I had chosen her as my trip companion. I was happy to have her along, it would be strictly platonic etc. I explained about when we would be leaving, where we would meet in Toronto etc. I told her about the media requests and how excited I was about that (having never received media attention before). She asked a few questions about the media and agreed to have the paper and the show contact her to make arrangements and ask questions of their own.

I called Jackie at the TV show, and Greg at the paper and filled them in on KJ. I answered more of their questions for background and sent the paper our detailed travel schedule at their request. It was now three days until departure and I was pretty content about the trip. I was still mad as hell at my ex, but that anger and hurt were fading.

I was just drifting off to sleep when I got a FaceTime request from KJ. When she appeared in frame, she wasn't alone.

"Hi Martin, this is my boyfriend Josh."

Boyfriend?!? KJ never said anything about a boyfriend before!

"Uhh hi," I said. I was feeling a bit uncomfortable and angry about being surprised by this news. Not that I had any plans to do anything with KJ other than travel, but the boyfriend added a whole new wrinkle.

The silence was awkward and deafening. KJ broke the silence. "Josh wanted to meet you face to face before we fly to Toronto to meet you for real. I'm going to let you guys talk." She left the frame and handed her tablet to Josh.

He looked to be in his mid-twenties. His short blonde hair was a little spiky and he had a nose ring and a gromet earring in his left ear. He regarded me for a moment with cold grey eyes, then spoke.

"So your fiancée dumped you eh? Dude, that's harsh."

"Yeah, it sucked."

"Why do you wanna take my Janey with you for a month? Why not just stay home and move on?"

"Josh, I worked really hard on this trip. I saved the money and did the research and planning. I've put so much effort into it that I didn't want it to go to waste. And honestly I'd be out about 8 grand if I cancelled. I didn't buy cancellation insurance because I didn't think I would need it. So it's like a use it or lose it deal."

"Why Janey?"

"It seems like we will get along." I explained my selection criteria and some of the emails I got and the people who contacted me. "Your Janey was the best fit."

"You do realize she's with me right?"

"Until tonight, I had no idea she was attached. But that was not my plan anyways. I don't want a rebound girl. This is supposed to be a platonic thing. My intentions are honourable here."

Josh was silent for a moment, then he called Jane back. He told me to hold on a sec, went off camera to talk to her, then came back.

"Alright Martin, I'm holding you responsible for her safety. I'm also holding you to your word that you will not make a move on my girlfriend. We will see you in a couple days at Pearson. We are arriving for 7am at Terminal 2." We said our goodbyes and disconnected.

A couple days hence, I got up before the sunrise and went to collect Jane and Josh from the airport. When we all met in person, we shook hands and hopped in my car to head to the TV station in mid town. On the drive, we chatted and laughed and things were going well. We made good time to the station and arrived in good spirits.

We were met by a production assistant and taken into makeup. Whilst in makeup, we were introduced to the host, Kristin Spencer. Kristin was resplendant in a red outfit that was at once modest and form-fitting. Her white blouse had one button undone that hinted at her generous cleavage. I'd been a fan of hers for years, admiring her beauty and grace and wit. And of course she was just so fuckable that when she introduced herself, I actually gushed like a star-struck teen meeting a boy band. Both Jane and Josh played it much more cool.

Kristin was a TV journalist who worked for one of the major Canadian broadcasters. She had started out reporting on entertainment pieces, but had moved on to report on travel. The word on the street is that a major celebrity had made a pass at her, which she rejected so viciously that the celeb went to her boss to complain about her lack of professionalism and tried to get her fired. She had the upper hand though because the pass had been recorded on a hot mic. In the end, it was said that her bosses were doing everything they could to keep her happy, including a generous raise, a weekly spot on the national broadcast and the travel beat. The weekly spot was apparently unheard of for the travel beat. Everyone figred that she had her network execs by the balls and was using that as leverage to further her career.

About 30 minutes after meeting Kristin, we were on the set, answering questions and sweating under the hot lights. I had to answer questions about the weirdest response I had received, what I thought my ex might be thinking, why I'd selected KJ etc. All pretty benign stuff.

KJ made a bigger splash with her revelation about Josh, so they brought him out too and asked some pretty tough questions. I was pleased to see he was so sanguine about it all, and when Kristin asked him why, he told them about our FaceTime interview and how satisfied he had been with my answers.Once the interview was done, Kristin thanked us and told us she'd be meeting us in Venice in 10 days.

Josh, Jane and I went back to my condo to drop off their stuff and freshen up. While Jane was in the shower, Josh went out to the balcony for a smoke and I busied myself with some light packing. We went out for lunch and then came back to the condo so they could rest. I had several errands to run, so we agreed that they'd hang out until I got home, then we'd all go out for dinner.

I went out and did my running around, but I got done more quickly than anticipated, so I returned home about 45 minutes before I had told my guests I'd be back.

As I walked in I heard the shower running, but Jane wasn't in the living/dining/kitchen. I assumed she was maybe in my room which has the en-suite with the shower. Respecting their privacy, I waited another 20 minutes until the water stopped running, then made enough noise so they'd know I was home.

About 10 minutes later, Josh emerged from my bedroom wearing jeans and a T-shirt. Then Jane came out in flannel pajama bottoms and a short cropped T-shirt that bared her midriff. I was struck by how beautiful she was. Her long brown hair was still wet and she was busy towel-drying it. The motions she was making caused her tits to jiggle a bit, and her hard nipples poked at the thin material of the shirt. The flannel pants looked plain, but hugged her curves too. Her beauty and sensuality seemed effortless! I was seeing her in a whole new way, and suddenly her body and face were causing lusty thoughts.

She was startled to see me, and shot a worried glance to Josh. He held out a hand, pulled her to him, and wrapped her in a hug (I'm assuming to reassure her). Josh asked me when I got home, looking worried about my response. He shot a guilty look at Jane, and suddenly it dawned on me that they had been fooling around and potentially fucking in my shower/room. I lied and said I just got back. They both seemed relieved and after that, we made our dinner plans: Mexican. Then I got ready to go and did some more packing.

We left the condo at 7 and hopped a cab to take us to Hombre's. Josh indicated this was his treat and ordered a round of tequila for us. We had nachos and beer and another round of tequila. Then we had our mains and more tequila, and I ended up getting quite drunk again. Josh and Jane were feeling no pain either.

When Jane got up to go to the bathroom, I watched her leave the table, enjoying the way her butt moved in her jeans. Josh must have noticed me ogling his girlfriend's ass because he leaned over and said "This is really good of you to take her Martin, but keep your hands off my girl. I'm trusting you with Jane, so don't stab me in the back."

I assured him as best I could that I'd be cool and that I wasn't after her. I guess he seemed ok with my answer, and when Jane returned, he went to the bathroom. Jane leaned over the table, providing me with a quick view down her top, and told me again how excited she was about the trip, and how well we were going to get along, and how much of a gentleman I am.

All I could think was that I couldn't wait to see her in her bathing suit, or maybe naked.

Chapter 3 - The Trip (and the Teasing) Begins

We made it home from Hombre's at 11, and had an 8am flight to Paris, so that gave us maybe 5 hours to sleep. I got the couch pulled out for them and staggered into my room.

I should have fallen asleep, but apparently my guests decided to have another session, and the enthusiastic sounds she was making kept me up. Jane made no effort to keep quiet, and my prick got hard as I listened to her command Josh to lick her pussy. "Yes Josh, lick it just like that. Yeah right there. Harder. I'm going to cum soon! Oh my god, you're so good at this. I'm going to miss you and your tongue when I'm gone. Yes that's it, lick my clitty! I'm almost there Joshie baby! Ahhh!" She went quiet for a moment, then I heard her groan in satisfaction. Another moment of quiet, then the springs on the pull out bed started squeaking. I pulled out my hard member and stroked it as I listened to them fuck. Their pace picked up, and again she started talking dirty.

"I love your cock! It's so big and it fills up my little pussy! Fuck me harder! That's it, give me all your hard cock. I want it. Oh god fuck yes! Do you want to shoot your load in me? Do you want to spray your spunk in my hot wet cunt? Come on Joshie, fuck me! That's it! You're so deep inside me."

As I heard Josh shout "I'm coming babe!" I felt my own balls clench up and then let go. I came all over myself in forceful spurts as I listened to them reach their orgasms and go over the top. I heard no more that night as I passed out.

The alarm I had set for 4:45 came too early and I played snooze bar tag with it several times, before finally staggering out of bed and into the bathroom. After I finished my oblutions, I went to wake Jane and Josh.