Winning the Lottery - 2. Vancouver is nice, but Honolulu is better

It seemed like Vancouver was one big park with gorgeous beaches. Although I soon discovered that it rained a lot, but when the sun made an appearance the whole city sparkled. Even in April it was warm enough to walk around in shorts and a t-shirt. I loved it!

Luckily it only took me two weeks to land a job. I was hired as an accountant with a rental management company. As you can imagine, my personality was reserved, but my boss, the company’s controller, liked my work and gave me plenty of encouragement and positive feedback. Under his mentorship I began to gain confidence. I worked hard, and appreciated the positive feedback. But I never let my guard down. After all, weren’t my boss’s compliments just another form of motivating me; trying to keep me working hard?

I found a terrific apartment in Vancouver’s West End. It’s an area close to downtown but surrounded by ocean and beaches with a huge park (Stanley Park) at the end, and everywhere you look flowering trees. Rent was expensive, but there I was, living heaven. And the neighborhood was full of gay men. It seemed like a smorgasbord to me. All I needed to do was heap my plate full. But I soon realized that there’s a social reserve in Vancouver. Men weren’t exactly falling all over themselves to meet me. I needed a strategy. Some good old fashioned marketing with me as the saleable product.

It was time to find a boyfriend. Somewhat unrealistically I envisioned finding a guy with whom I could share my life. Not some pick up in a bar—that wasn’t going to be my marketing strategy—but rather a regular, conservative guy like me. I wanted a nester. I wanted a wedding. I wanted stability and love.

When you want something enough it will happen. I met my dream boyfriend on a plane bound for Calgary where I was to attend a meeting. This guy was only a few years older than me, very handsome and very charming—a businessman going to a conference. Flirting on the plane led to an invitation for a “drink” in his hotel room, which I readily accepted. He was smart and funny and he pulled me like a magnet. His hotel room was dominated by a queen bed which we fell into immediately, drink forgotten. There was no hesitation; we both knew what I was there for. It was all firsts for me: kissing, rubbing dicks, feeling his cock and balls, exploring the plains and ridges of his body, receiving a sloppy blowjob, which I gladly returned. I admitted to him that he was my first and he told me he was honored. He didn’t push beyond my comfort zone. Needy and naive, I fell hard. He was very considerate but very passionate about sex; he relished his role as teacher. And in turn, I was an eager student--enthusiastically cooperative. We didn’t go beyond frotting, hand jobs and oral sex that first time. I slept happily in his arms with visions of spending a long and happy life with him. I was intoxicated with newly found love!

I woke up to another amazing, sloppy, blow job. I’d died and gone to heaven.

Just after the blow job, however, my fantasy world crumbled. He told me not to get “hung up” on him because he was married with three kids. Fuck! But when he gave me his phone number and told me to call if I wanted to hook up again I took it. I was naive and stupid and very needy, and maybe still a bit in love, or maybe beguiled by his charm and good looks. And hooked on the sex, let’s not forget that. At any rate, I didn’t have the courage to let him go, so I continued an affair with him for the next six months. We eventually got around to anal sex. I’d heard how nice it could be, but it just seemed to hurt. He’d come to my place when he had a bit of free time, maybe once every couple of weeks. I lived for his visits. He complained about his wife: how they didn’t have sex anymore, how bitchy she was. I guess I took this as a sign he’d leave her eventually, but the truth was he had no intention of doing so. And what had started as a little teacher/student role play took on a darker tone. He became rougher, always thrusting his cock deep into my throat, which I found unpleasant, and his fucks became aggressive. The ‘role playing’ took on a dom/sub nuance. I very definitely did not appreciate being called his bitch. I may have been inexperienced, cooperative even, but enough was enough! I finally grew tired of being used and became resentful and angry. Finally I let all my disappointment and rage come out in one big, firey explosion. I gave him a good telling-off and told him to get lost and never contact me again.

After that, I had no road map to follow; I’d lost trust in pretty much everyone. For the next couple of years I drifted. One thing about Vancouver is that people there are very health conscious. It was easy to find other gay men who enjoyed running, hiking, kayaking and working out at the gym. Most of the guys I met were either already in relationships, or just wanted fuck buddies. I didn’t mind the occasional on-night stand, but it was a little discouraging. For some reason I didn’t pass the ‘boyfriend material’ test. My ego took a real beating.

On a positive note, I took up volunteering with one of the Downtown Eastside homeless shelters. Once a week I’d go help prepare, serve and cleanup after a meal. All the volunteers were extremely compassionate, and for the most part the beneficiaries were appreciative. I loved my once a week evening at the hostel, it was a nice counterpoint to my stagnant love life.

Work was going well. But I never let my guard down. My boss’s behaviour was impeccable, and he seemed nice, but I lived in fear of making a mistake and being shown the door.

My company had two offices: a head office in Calgary and a second office in Vancouver. We managed apartment buildings and parking lots. I was the assistant controller. My main job was to prepare monthly financial reports, but I had a myriad of other small jobs, like banking and payroll. I joked that my job was to do all the things that nobody else wanted to. But I didn’t mind. And as I said, my boss was well behaved. The regular paycheck was nice and my savings account was growing bit by bit. I considered buying a car, but Vancouver’s public transportation is excellent, and it was much more cost effective to use one of the car sharing services for the occasional times I needed one.

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Unbeknown to me, the owner of the company was in negotiations to buy a small rental management company in Honolulu. I guess the negotiations were successful because, on my 24^th birthday, that’s when my boss called me to his office and asked me to shut the door.

Shit, I thought, this is it. Life had taught me to expect the worst; I just couldn’t figure out what I’d done wrong...

But to my amazement, he told me about the new Hawaii office and asked me to transfer.

The Honolulu operation, he told me, was small. It had been a family business whose owners, Mr. and Mrs. Chen, were retiring. Mr. Chen was the manager, and Mrs. Chen ran the office. In addition to the Chens there was an accountant, another manager that took care of client liaison (for things like repairs and cleaning) and three agents who took care of rentals. Besides a couple of apartment buildings and three or four office buildings the business also ran a small tourist rental agency acting on behalf of condo owners. Mr. Chen was willing to stay on as general manager, but Mrs. Chen wanted to retire, so my job was to replace her, but I’d be integrating operations with our Canadian offices so that everything would be reported on a consolidated basis.

I didn’t get a lot of notice. Within three weeks of my boss giving me the good news I was given a bon voyage lunch (where several people promised to come and visit me) then that night I was on a plane bound for Honolulu. I only had a couple of suitcases with me. I’d sold or donated all my furniture. I had only one or two mementos to pack. In lieu of moving expenses my company gave me a fairly generous allowance to get my new apartment furnished and set up.

Hawaii was the first tropical location I’d ever been to, and from my first view of blue ocean water and palm trees from the plane I was fascinated. Then when I stepped off the plane into the open walkway and felt the warm tropical air I was utterly smitten. Hawaii was even better than I dreamed about. Tropical flowers. Warm, scented air. Palm trees. Sunshine. Oh man!

Mr. Chen found me a small apartment in a building just behind the Ala Moana shopping centre. He couldn’t get me a break on the rent, which was fairly expensive, but he did facilitate my jumping to the top of the waiting list for an apartment. It was only a short walk from the beach and just a few blocks from the excitement of Waikiki. It was on the tenth floor had a partial water view! How lucky can a guy get?

I was thrilled with my new apartment. The ocean view was indeed partial, I had to stand right next to the window and look right to see the ocean. Off to the left, I could see the mountains behind Honolulu. My windows faced toward Diamond Head, but I couldn’t see that because other buildings blocked the view. It was about a block behind the big Ala Moana shopping center, and there was a large Asian grocery store nearby.

Mr. Chen turned out to be a delightful man who seemed to know everybody. With my moving allowance and my savings I bought a convertible from his cousin’s car dealership (a ten year old Toyota Solara that was in good shape) and some nice Hawaiian-style furniture from another guy he knew. I made sure to get a sofa bed just in case any of the people who promised to visit actually did come. Of course all the salespeople promised great deals, but they all seemed to be smiling when I left their places of business, so I suspect they got their required profit from me. But I was operating in a haze of happiness, the likes of which I had never known, so I didn’t begrudge them their commissions.

I soon discovered that Hawaii has its own unique dress code. Almost all men wear patterned shirts. Always! Suits are rarely required. So on the evening of my first day of work I found myself in the menswear section of Sears at the Ala Moana shopping center surrounded by a sea of colorful Hawaiian shirts. I felt a little lost and unsure, but soon a very friendly sales clerk arrived. When I explained that I was newly arrived and needed to blend in he explained some of the intricacies of Hawaiian dress code. Fairly complicated! But I picked out several shirts that suited my coloring and physique. He also suggested some good quality slacks that would work well with the shirts. I even got a couple of pairs of new shoes that completed the look. Whoa! My Visa took a big hit that night.

I was a little self-conscious walking into the office the next morning decked in black slacks and a hibiscus patterned shirt, but everyone was very complimentary, and Mr. Chen called me an honorary Hawaiian. I was thrilled, but more than that I had a sense of feeling that I had, at last, found my true home.

Work was a big challenge. Mrs. Chen’s accounting system was a antiquated, and I had to install and convert all the data over to my company’s. That necessitated going everything with a fine tooth comb to create some sort of order out of chaos. For the first few weeks I was working six days a week, ten hours a day.

But I still had plenty of time to explore my new surroundings. I lived close enough to the main tourist area, Waikiki, that I could walk over in the balmy evenings and take in the sights and sounds. The stores stayed open late to accommodate the tourists, and there were always throngs of happy people on the street until late at night. Restaurants and bars were always crowded. It was like a perpetual carnival. I enjoyed just strolling and soaking up the atmosphere. Sometimes, I would buy myself an ice cream cone and sit near the beach watching the moonlight play on the water.

At first, my former colleagues from Vancouver texted me regularly, and I texted back attaching lots of photos. But after just a couple of weeks the texts dropped off. Within four weeks, with the exception of my boss, with whom I was in frequent contact, I was forgotten. Life moved on.

I told Mr. Chen about my volunteer work in Vancouver, and he suggested I do the same in Honolulu where there was a real homeless problem. The need for volunteers was endless, he told me. I was soon working one evening a week at a shelter. At first it was a challenge, because the Hawaiian culture is different than what I was used to. Many Hawaiians were downright suspicious of outsiders, and at first the staff and clients were a little hostile. But after a few weeks we reached a tacit understanding, and I began to see the warmth of the culture. As it turned out, it was a good way for me to “integrate.”

I checked out a couple of gay bars in Waikiki. I was propositioned a couple of times by tourists, and once by a tourist couple, but politely turned down all offers.

One day I got a text from one of those former colleagues who explained that she had a flight attendant cousin who had a layover in Honolulu the following weekend, and would I like to have coffee with her cousin and show her around a little? Me, a tour guide? Well, why not? The idea really played to my ego. Me, the newly minted Hawaiian! Texts flew back and forth and it was arranged that I would meet Cousin Mellissa on Saturday at the Waikiki Hilton. Not the big one facing the beach, but the smaller one a block back. Apparently a lot of airline people stayed there during layovers.

At the appointed hour, I presented myself at the hotel’s restaurant and was met by vivacious cousin Mellissa. We were led to our table where Mellissa kept up a non-stop stream of questions. Did I like Hawaii? Was it warm all the time? Did it ever rain? Had I met any new friends here? I barely had time for one word answers and was beginning to wonder what I had let myself in for. Mellissa seemed a little ADHD. Although she was asking a lot of questions, I got the impression that she wasn’t listening to the answers. I wasn’t sure I wanted to play tour guide to this chatterbox and was beginning to strategize an early getaway.

Suddenly, she looked over my shoulder, beyond me then shouted, “Derrick! Over here! Derrick!”

I turned to see who she was yelling at, and I saw a nice looking guy give a little wave and start in our direction. Mellissa quickly explained that Derrick was one of her crew members, and did I mind if he joined us? I quickly agreed. For one thing the guy wasn’t hard on the eyes, and even better, he might provide some relief to Mellissa’s manic questioning. As I studied him further I concluded that he was good looking in a wholesome sort of way. Green eyes, sandy blond hair with a hint of red, and a disarming smile. A touch of Irish perhaps?

Introductions were made and Derrick sat down. The server arrived with menus and there was a moment of silence as we looked them over. Mellissa, thank goodness, seemed a little more subdued now that Derrick had joined us.

It took a few minutes to establish who I was and why I was meeting with Mellissa, then conversation seemed to flow a little more naturally. Mostly it was between Derrick and me. Another question and answer session, of course, but this time Derrick seemed genuinely interested in my answers, and I was curious about their airline jobs and what that entailed. It seemed like a very glamorous life to me, but they assured me that it wasn’t. Yeah, right, like I believed that!

I was curious about the travel benefits I’d heard so much about and they explained that, yes, they were excellent, but it was always on a ‘space available’ basis and not guaranteed.

Mellissa had been to Waikiki several times but this was Derrick’s first Honolulu layover, and he was curious about everything.

Mellissa nibbled at her fruit place while Derrick and I chowed down on bacon and eggs. Mellissa’s phone chirped and she exclaimed, “Oh my God! Gucci is having a sale! Would you mind terribly if I leave?”

Derrick and I said, “No problem.”

After she’d left I couldn’t help asking how she could afford Gucci on a flight attendant’s salary. Derrick shrugged and said he had no idea.

“I can’t even afford to look in the windows of the Gucci store,” I said.

“Not many people can,” said Derrick. And we both laughed.

Derrick turned out to be good company and conversation flowed naturally. Something clicked between us. It was like we’d been good friends forever. He seemed straight but I couldn’t help feeling a little wistful thinking what a great boyfriend, lover, partner, he’d make. And by some sort of unspoken agreement between us we avoided the usual questions about girlfriends (I assumed he wasn’t married since he didn’t wear a wedding ring). But surely, I thought, a good catch like him would have a girl back home. Her name is probably something sappy like Mary-Sue and they were childhood sweethearts.

I felt a stab of jealousy with those thoughts, and I silently scolded myself for my negativity.

Derrick seemed content to sit chatting with me after our breakfast dishes were cleared away, so thinking that I’d like to spend more time with this charming man, I offered to give him the Cook’s tour of Waikiki.

His answer was to smile broadly and agree enthusiastically. I thought I might have detected a little flirting in his response but quickly dismissed the notion. He was, after all, probably straight or, on the off chance he was gay, in a committed relationship. How could such a handsome, beguiling man not be?

I walked him down Kuhio Street to the International Market, and he seemed delighted by all the touristy bric-a-brac on display. The market’s maze of alleys and a large central tree make it seem bigger than it really is, and we were soon past the gold bangles and hula dolls and out onto Kalakaua Avenue. I pointed to the right to where the high-end stores were but suggested that he might like to cross to the beach and see, what was to me, the real Waikiki. A short alley led to the white sand beach in front of the famous pink Royal Hawaiian Hotel. Derrick’s eyes bugged out when we reached the beach. I couldn’t blame him. The view of the sand, blue water, lounging tourists, catamaran boats and hotel fronts is truly breathtaking.

“Wow!” he exclaimed.

We took our shoes off and crossed the powdery sand to the water. Derrick turned slowly in a circle as he took in the sights and sounds of this magical place that is Waikiki.

He said, “I never knew a place as beautiful as this existed. I mean, I’ve been to Maui, and it’s beautiful, but it’s not as much fun, and I’ve been to Mexico, but their beaches are nothing like this. This is.....wonderful!”

“Glad you like it,” I said, pleased as punch with Derrick’s impression of my new “home.”

We walked until we came to a low seawall then sat, side by side, and took in more of the sights. Derrick asked if I would adopt him so he could come and live here. I laughed and said, yes and gave him a little shoulder bump that sent sparks though me and blood straight to my cock.

“Thank you!” he said. Then he reached around my shoulders and gave me a quick hug. More blood rushed to my dick.

That gesture made me suspect Derrick might—dare I hope—be gay, and I allowed that hope a little light of day. The afternoon passed quickly as we chatted about everything and nothing. From what he told me about his family they sounded like a warm, supportive group. Totally the opposite of mine.

I hadn’t realized it at first, but Derrick was a US citizen. The airline that he and Mellissa worked for was based in Seattle. He told me he lived in Seattle, not far from the airport. He’d grown up on Orcas Island, just north of Seattle, where his parents ran a Buddhist retreat. I asked him if he was a Buddhist, and he said that he subscribed to the philosophy, but he wasn’t really an ‘anything’ when it came to religion.

Soon it was time to deliver Derrick back to his hotel so he could get ready for his flight out that evening. Before we parted we exchanged phone numbers so we could text each other. Derrick promised that the next time he had a layover in Honolulu he would contact me. I sure hoped he wasn’t kidding.

We shared a warm hug at the entrance to his hotel that left me longing for more. He headed inside, and I headed back to my apartment. Saying goodbye to my new friend was bittersweet. On one hand I was glad to have a new friend, and dare I hope, more. Certainly, Derrick and I had bonded quickly and, I could honestly say that in the short time I had known him he had become my new best friend. On the other hand I felt crushed at having to say goodbye after such a short time. I wanted to spend a lot more time with him. With my luck though, I figured he was already in a committed relationship.

Confused as my feelings were, I was horny as hell, and had a quick wank the moment I got in my door.

Once the sexual euphoria faded, I chided myself, You don’t even know him! He probably won’t call. You’ll never hear from him or see him again. Get over it! You know you can’t rely on anyone! Why would he think you’re boyfriend material?

I promised myself I would forget him. I watched a movie. Alone.

At 10pm, just as the movie finished my phone pinged with a text. Derrick had written: Thanks for the wonderful day. You make a great tour guide! Hope to see you again soon. I’ll let you know when my next layover is. xxD.

I was elated that he’d contacted me and I loved the two x’s. I wrote back that I would be delighted to continue our tour of the island next time he was back. He replied with a smiley emoticon.

Two days later I received another text telling me he was bidding for his next month’s schedule and was hoping to get at least one Honolulu layover. I replied, fingers crossed!

The next day: Damn! Couldn’t get a Honolulu layover ;( Very disappointed!

Damn! UR always welcome to come for a visit if you have some time off. You can stay with me. Sofa bed. No pressure J

One hour later: Short notice, but I have 2 days off next week if UR available.

Absolutely! I’ll do my best to get a day off to play tour guide J

Great, I’ll arrive on Tuesday evening and leave on Thursday morning.

Hopefully there will be room on the plane!

I’ll make sure there is LOL.

I took a deep breath to steady myself and wrote back, Please tell me you’re not married, engaged, or otherwise committed.

I have commitments, but not in the romantic department. I will explain all when I get there J

I cleaned my apartment from top to bottom. I had my car detailed. I stocked up on beer, wine. I made grocery lists. I planned a circle-island driving tour. I asked Mr. and Mrs. Chen for advice on what the best sights were. They gave each other a knowing look. I blushed. I asked Mr. Chen three times if he minded if I took Wednesday off, and he assured me three times that it was fine. I phoned my boss in Vancouver, explaining I had a guest coming, and begged for the day off. He laughed at me and told me I was a big boy and didn’t need to ask his permission for a day off. “You’ve earned it,” he said, “Go have some fun!”

I went to a trendy salon and paid for an outrageously expensive haircut.

Time slowed to a crawl.

Eventually, Tuesday arrived....