The First Step

By HedbangerSA

I was on the boat before I really thought about why I was doing it. My secretary talked me into it. She went on a cruise with her family and gushed about it for weeks afterward, and then started hounding me to do it. Taking a break sounded pretty good—I’d been putting in a lot of hours since the divorce. So when Brianna, that’s my secretary, brought in the brochures and broke it down to baby steps for me I never really had to say “yes.” I picked Western Caribbean over Eastern. Six days over five days. Grand Cayman over Ochos Rios.

A lot of things in life, large and small, work out that way. Even really big decisions that change your life. I couldn’t remember making a conscious decision to get married. I remember deciding to ask Julie out the first time, but after that things just sort of blurred. Living together made sense because we were spending all of our time together anyway, with double expenses. Getting engaged seemed unavoidable because that’s what people expected and after I agreed to go into the first jewelry store to “see what they’ve got in a nice solitaire setting” the rest just happened.

My marriage was an expensive lesson, but I applied what I learned to my job with impressive results. I was part owner of a venture capital firm that specialized in turnarounds of failing companies. That meant I earned my living by getting people to do things they probably shouldn’t do on a regular basis. I firmly believe that you could convince a normal, rational person to jump off the John Hancock Building as long as you broke the decision down into small enough steps and made each one sound logical.

I boarded the boat in Miami, feeling like I was being processed at Ellis Island. For a fairly expensive vacation, cruises seemed to attract an unimpressive crowd. You’d think they backed the damned thing up to a Wal-Mart and started loading people on at random.

My cabin was nice, though calling it a “suite” was a stretch. One decent sized room with sleeping and sitting areas, a small walk-in closet, and full bath, but it had its own balcony and a big window. After I peeked into a few of the regular cabins from the hallway I started to appreciate my own—they looked like sleeper compartments on a train. The service was great, though. You couldn’t walk three feet without tripping over a crewmember wanting to help you, usually with something to eat or drink.

The first couple of days I slept a lot, ate a lot, and caught up on my reading. I skipped the shore excursions in Grand Cayman because I’d been there recently and the effort required to sign up for a jeep tour or snorkeling trip didn’t seem worth it.

By the third night I was getting restless, so after dinner I wandered up to the casino. It looked like casinos everywhere and it was packed. That felt good because of the familiarity and the artificial camaraderie so I stayed. I ended up at a $25 blackjack table and after four hours I had a very pleasant beer-induced buzz and was maybe a couple of hundred dollars ahead. The other six spots at the table churned, with someone new joining every half-hour or so—a stream of faces studying cards, laughing, and drinking. Only a few registered with me, one in particular.

About ten o’clock a woman took the seat two to my left. She seemed out of place, particularly given the table stakes. Long, dark brown hair, late twenties, wearing a “Maryland is for Crabs” sweatshirt and a nice pair of jeans. Even with no makeup her eyes were striking—they were an odd shade of blue-gray with long lashes. Despite the bulky sweatshirt you could tell she had an impressive rack.

She was wearing a wedding band and matching engagement ring with a tiny diamond but wasn’t with a guy as far as I could tell. She seemed distracted, glancing around the casino, and it showed in her play. She lost steadily for nearly two hours before she finally pushed away from the table. She left the casino with another woman, and they made for an odd couple. The best-looking woman I’d seen on the boat, slim and leggy, paired with a short, fat, waddling, frizzy-haired gnome of a female.

I quit gambling about the same time and went up to the Lido deck for the midnight buffet. I concentrated mainly on the enticing array of desserts and tried to keep it light. Sleeping on a rocking boat with a full stomach worried me. I wandered toward the back of the dining area looking for a table and on the way passed my beautiful former blackjack companion and her fat friend. The gnome had two plates piled with enough quesadillas and tacos to feed at least three normal people. The cute one seemed to agree with me—she was eating a small portion of bread pudding. She looked sad.

~~~

The next day I got up around nine and went to the health club. It was great not having to rush through my workout. I spent a good two hours in an impressive gym that looked out over the bow of the boat and the rolling chop of the western Caribbean sea, then another hour in the steam room and Jacuzzi. They had a full service health spa too, and I thought about a massage but decided to pass.

I showered, changed, and went to the Internet café to check my messages. Across from the café was a row of large picture windows, each with a padded viewing bench built in. In one of them I spotted the “Maryland is for Crabs” woman from the night before. She was sitting with her back to the wall, feet up, staring out the window. She looked even unhappier now.

I rushed through my messages and logged off, then walked over.

“Can I help?” I asked. She glanced up.

“No, I don’t need anythi…” she stopped, apparently expecting a crewmember. She looked at me, confused and wary.

“Sorry. I didn’t mean to startle you,” I said. “You looked troubled. I was wondering if there was something I could do to help.”

She opened her mouth a little but didn’t say anything, looking even more confused and thrown off balance by my offer. Her eyes were gorgeous, especially in the sunlight. She had great cheekbones, a nice nose—narrow and delicate—and a long, slender neck. Her clothes clashed with her physical perfection—a striped sweater and slacks that looked like they’d been tailored for someone else. The sweater was too big at the shoulders and waist, but in between it confirmed my theory about the woman’s tits. They were bodacious, straining the fabric of the sweater, and from the way they rode on her chest they looked natural. I smiled at her.

“You sat at my blackjack table for two hours last night. That creates an unbreakable bond—I’m obligated to look after you for the rest of our natural lives.”

She squinted at me, then smiled. “Oh, right. You’re the guy who was winning.” Then she laughed—a beautiful, clear musical laugh that suited her.

“That’s pretty funny. Thanks, I needed a laugh. But it’s nothing, really.”

I gave her a skeptical frown. “I bet it would feel good to talk about it and I’m a great listener. Why don’t we go have lunch? I’ll buy.”

I nodded toward the dining area, where the free buffet was underway.

She laughed again, but looked unsure. I reached out my hand.

“I’m Andy.”

She took it. Her hand felt terrific, warm and soft with long, slender fingers.

“I’m Beth.” She bit her lower lip, still deciding. I made it easier for her—I kept my grip on Beth’s hand and gently pulled her to her feet.

“Come on, Beth. What’s the worst that could happen?”

She smiled and nodded. Like I said, the first decision is the hardest.

We got lunch, both taking soup and the Creole chicken and shrimp with rice. After we sat down I kept the conversation on small talk for a while—unthreatening and light, mainly about the cruise. Beth was a little shy, unsure of herself socially, which seemed strange for someone so striking.

“So, what had you so troubled earlier?” I finally asked. “Is it the money you lost last night?”

She blushed. “That’s part of it. I shouldn’t have been gambling so much. But I was kind of depressed anyway and I thought that might help. It didn’t.”

“So why is that so bad?”

“Ronnie—he’s my husband—is going to be mad when I get home. I put it on our credit card and I lost almost five hundred dollars.” Saying the amount out loud seemed to upset her. She looked like she might cry.

I reached over and took her hand.

“Hey, it’s okay. Your husband isn’t on the boat?”

She shook her head. “That’s part of why I was depressed.” She paused, taking a deep breath to stay in control. Her hand was shaking.

“Tell me about it, Beth.”

“Well, we were going to come together. It was kind of a big deal, at least for me. A chance for us to spend time together, you know, and be close again. But a couple of weeks ago these buddies of his asked him to go ice fishing up in Canada and he said he would. He said it would be more fun than some dumb cruise.”

Now Beth was crying, quiet tears rolling down her cheeks, shoulders shaking. I was dumbstruck. This loser would rather sleep in a freezing cabin or tent with some beer-soaked, unshaven buddies than be here banging the daylights out of a babe like Beth. There was no accounting for taste.

“So you decided to come with your twin, huh?” I asked, keeping a straight face.

“What?” she asked, wiping her cheek with her other hand. She was making no effort to reclaim the hand I was holding. Then she made a little snorting noise and started to laugh.

“You’re horrible. That’s my friend Emma. She’s nice!” Beth said, smiling through her tears.

“I’m sure she is,” I said, shrugging. Beth seemed calmer now, the laughter had helped. So I asked her to tell me about herself, how she met her husband—the story of her life. It took about an hour. She met Ronnie in college, when they were both sophomores. He was her first serious boyfriend. She turned up pregnant and quit school after they got married. Then she miscarried and never went back to college, though Ronnie finished. He was some kind of auditor for a restaurant supply company, and Beth worked as a supervisor at Target. She seemed to like her job and made a point of telling me that her grades had been a lot better than Ronnie’s before she quit.

It sounded as if Ronnie felt like he got tricked into getting married and cheated out of his youth. And that he’d been making Beth feel guilty about it every day for the last seven years. I didn’t ask her why they never had another child. I just listened, prodding her occasionally.

I noticed that Beth got these great little dimples in her cheeks when she laughed. And I loved her voice, soft and warm. It flowed over you like velvet. I was still holding her hand, giving the palm a little massage with my thumb. She stopped talking and we just looked at each other for a minute before she blushed and seemed to notice what I was doing with her hand. She finally pulled it away.

“This has been fantastic, Andy. I can’t thank you enough. You were right You’re a great listener and I do feel better.”

“Then why stop?”

“Huh?”

“Have dinner with me. I’ve got the late serving in the main dining room, table 43. There’s an open spot at my table. We could talk some more. Come on, it’ll do you good,” I said. Beth frowned.

“What about Emma?”

“She’s on her own—she’s a big girl. Is she a really good friend?”

Beth shook her head. “I’ve barely seen her since college, but she lives in Miami and she was available to fill in at the last minute.”

“So what’s the problem?” I asked.

“None, I guess. Okay, I’ll do it!” Beth said, smiling. She started to stand up but I reached for her hand again. It felt natural sliding back into mine.

“One more thing. How about if after dinner we hit the casino?” I asked.

Beth looked horrified. “I can’t afford to lose any more money, Andy.”

“You won’t. You can gamble with my money.”

Now Beth looked hurt. She pulled her hand away. “I couldn’t take your money,” she said. She looked like she was going to leave. I kicked myself mentally—I’d pushed Beth too far, too fast. I shouldn’t have said anything about the gambling until after dinner, when she’d had a few drinks.

“I wouldn’t really be giving it to you, Beth. It would still be mine. I’d just split the winnings with you,” I said, scrambling.

“What if I lost?” she asked, still looking wary but less upset.

“You won’t, believe me. I’ll be with you, making sure you play the percentages. You’ve got to stop doing stuff like taking a hit on sixteen when the dealer has a five showing.”

Beth smiled. “Was I doing that?” I nodded vigorously. She sighed, staring at her hand in mine for a long moment. She finally looked up.

“That sounds like fun but… it’d be wrong. I don’t want you to get the wrong idea about me, Andy. Ronnie may be a jerk, but I don’t… well, do stuff like…”

Beth stopped talking, flustered.

“I know that, Beth! I’m not trying to get you to do anything you don’t want to do.” I paused. What I said was true. It was just a matter of getting her to admit what she wanted.

“I like you, Beth. I could use a friend on this cruise and I think you could, too. Come on, we’ll have fun. And believe me, no pressure.” I made eye contact with her and held it for a long moment. “Friends, okay?”

She bit her lip, brow furrowed. Then she sighed, and smiled.

“I guess that would be okay. It does sound like fun,” she said. Another decision made, a line crossed.

She extracted her hand and backed away a couple of steps. I was afraid to say anything, for fear of messing things up again.

“Well then, I guess I’ll see you at eight o’clock. Table 43?” she asked.

I nodded. “Table 43. I’ll be wearing a jacket, no tie.”

“I’ve got a dress I can wear,” Beth replied, then turned toward the exit, acting self-conscious. Her butt looked fantastic as she walked. At the door she gave me a little wave and a cute smile.

As I talked to Beth, through the awkward first moments and the effort it took to get her to begin to trust me, I’d flashed back to a similar experience in college. I shared an apartment with five guys my senior year. To liven up a dreary spring semester we decided to throw a formal dinner party with some unusual rules to make it challenging.

We went to the lobby of a women’s dormitory and each drew a number between one and ten out of a hat. If you drew a three, then you were assigned the third woman who got off the elevators as your date for the party. There were points awarded for difficulty—if the woman was dating someone or engaged for example, and for how far you got your date to go the night of the party. There was a separate prize for the guy who got his date to wear the most audacious dress to the event.

What I was doing with Beth was different—I would be the only guy playing the game. But I still loved a challenge and it would certainly make the cruise more interesting.

Anything worth doing is worth doing right, so I did some research. I stopped by the health spa and beauty salon and spoke to the manager about a special package of services I might want. The boat had a nice woman’s clothing shop, and I went there next to see what they had and to get acquainted with the woman in charge. It pays to be prepared.

I went to the dining room early and spoke to the maitre d’. I moved Beth to my table for the rest of the cruise, which wasn’t easy given that she wasn’t present. Money talks, especially on a cruise ship, and a sizable tip got the job done.

~~~

At eight o’clock sharp Beth arrived. The dress she was wearing was hideous. Black and white geometric shapes, with a modest squared-off collar and puffy three-quarter length sleeves. It was all wrong for Beth—for her age, her coloring and her body type. The skirt looked designed to cover up matronly hips, something Beth clearly didn’t need.

Still, it was hard for Beth to look bad in anything. The dress was gathered enough at the waist to show just how long and slender Beth’s was. While it was probably supposed to be loose across the chest it wasn’t on Beth, who had a set of tits on her that wouldn’t quit.