Anything Goes

We finally arrived and landed at Daniel K. Inouye International Airport in Honolulu. We'd have to get our bags and then transfer to an island hopper to fly us to Kahului Airport on Maui for the first leg of our trip.

While waiting for our bags, I saw Big Red looking Hannah's way. His wife, a very unattractive heavyset bottle blonde with dark roots showing, was staring daggers at Hannah. I guess he had told her what he saw.

Hannah had put on big sunglasses and was ignoring the attention she was getting. I'm certain she was thankful she had worn dark pants.

We took our short flight to Maui after transferring our bags. We got ground transportation to our resort.

We checked in and we're quickly whisked to our modest but still very nice room. As Hannah begun to unpack, I told her I needed to make some arrangements for our plans for the next few days.

I went back down to the lobby and made my over to the concierge desk. I was hoping to find a guy working but instead found a woman. She was short, but very slender, wearing her long brunette hair straight.

"Aloha, mister...?"

"Aloha. I am John Steward. Room 506."

She did a quick scan of her computer, obviously pulling up my reservation.

"Ah, yes. Welcome to the resort, Mr. Steward. I'm Rebecca and I'll be happy to assist you with any needs you have while at the resort. What can I help you with today?"

"I'd, umm, like to inquire about potential massage services. To set an appointment this afternoon for my wife."

"Certainly. Is there a specific type of massage your wife is desiring?" she asked.

It felt like something unspoken was left out there in her question.

"Types?" I asked, hoping playing dumb will allow her to fill in the gap.

"Oh yes. Would she like Swedish, hot stone, deep tissue, Shiatsu, lomilomi, couples... sensual..."

There it was.

"Oh, umm, sensual, I think," I said, trying my best to be discreet.

"No need to be embarrassed, Mr. Steward. We're more than capable of providing a broad range of services for our guests. Is there any specific type of masseur or masseuse that your wife would prefer. We have a broad range of choices in our providers in the area," she replied in a lowered voice.

Her casualness about the request put me at ease but, to be honest, her frankness kind of turned me on. I clearly got the impression Rebecca was more than willing to be an active assistance in our plans.

"Would you have a masseur of a... darker skinned persuasion?"

"Absolutely, Mr. Steward. One gentleman comes to mind. He is highly reviewed and has an excellent reputation for delivering on his client's desires. I'll ring him up to see if he has an opening today. I think there's a good chance he'll have at least one. Do you have a preferred time?"

I left her with an open slot for most of the afternoon as our plans for the day were generally to hang out on the hotel's beach. She let me know she'd contact me with an appointment time and took my cell number to text it to me.

I returned to the room and before I had even entered the door I received a text from Rebecca- "Confirmed appointment. 90 mins beginning at 3pm with Tré. Sensual massage to client's comfort. $300, inclusive of tip, to be charged to your room. Enjoy ;)".

A winky emoji? I could've done without the winky emoji, Rebecca. Naughty girl.

As I walked in I saw that Hannah had finished unpacking and I heard her in our bathroom.

"Hi, babe. I'm back."

She stepped into the room and took my breath away. She had changed into a bikini that was un-fucking-believably hot. It was yellow with a knit pattern of diamonds. It was high waisted and the top had very strong points in a definite sixties style. Hannah wore it like a champ. Somehow it was many times more sexy than some trashy barely there thing might have been.

"I guess you like it?" she said with a smirk.

"Absolutely," I said as I went to her to take her in my arms.

I was shocked as she put her hand out, blocking my intended embrace.

"Oh, sweetheart. Don't get all revved up. I don't want you to mess up my makeup or my hair. You want me looking hot for all the other guys, don't you?" she said coquettishly.

Do you remember the end scene in movie Seven when Somerset realized what was in the box and said something to the effect of "Stay away. John Doe has the upper hand"? That was this moment. I suddenly remembered that Hannah came on this trip knowing she was going to offer herself up to meet my desires. She planned her outfit. She prepared herself to be desirable to others. She knew what would trigger a wannabe cuckold. She may use the talk of me giving her orders to assuage any guilt she might have about break her marital vows and her deep-seeded morals, but she came prepared.

And I don't take lightly the revelations from her past into all of this either. We've been married ten years, together almost twelve, and she has never even eluded to those stories. How they played into all of this, reflective of the revelations of my own previously secretive desires, loomed large in my head.

Fuck me, I'm so screwed, aren't I?

Shaking off being incredibly turned on by both her physical appearance and her denial of my affection, I just smiled back.

"Oh, of course, my love. I completely understand. We have a plan to stick to."

She nodded in earnest agreement with a little, girlish giggle. Damn.

"Well I have an update for you, dear," I began, "I have made an appointment for you at 2pm today to have a massage to get your vacation started off right. So let's go grab us some lunch and enjoy the beach for a bit before you're due back here."

"A massage? Oh honey that's so sweet of you. I can't wait. That'll be wonderful," she beamed.

"I'm glad you're pleased by my little surprise."

We went to the pool side café for lunch. I had an excellent roast pork sandwich with Terra Chips; Hannah had a light chicken salad croissant sandwich. Neither of us are big alcohol drinkers, but to get in the spirit of things we split a Mai Tai. Afterwards, we made our way to the beach.

Between lunch and making our way to the beach, Hannah was very much a center attraction. I saw more than one wife get annoyed with their husbands for staring unabashedly at Hannah. One even punched her hubby in the arm when he literally dropped his jaw with absolutely zero cool. I've always known that Hannah was really out of my league, but moments like this just emphasize that reality.

It also put in my head a thought that hadn't previously occurred to me in the whirlwind of a day we'd already had - if we really go down this path, and it seemed like Hannah had already committed to, would I set myself up to lose her over my more salacious desires? We had over a decade together and truly were deeply in love with each other, but desire and lust can be monumental agents of change in the realm of relationships. This was a high risk/high reward situation for sure.

This was what was going through my head as we set our stuff down at our picked spot on the beach and walked hand and hand to dip our toes in the gorgeous surf. We were smiling at each other as the waves lightly crash upon our legs as our feet sunk into the sand.

"I love you, you know," I said to her, perhaps a little shakier than I intended.

"I love you with all my heart, honey," she smiled. Then, being the very empathic woman that she was, she reached up and caressed my cheek.

"We don't have to do this. I'm going crazy with love and desire for you just with the talk about... all of this... You're enough for me. You don't have to prove anything or pay me back in anyway."

"Oh honey, I know that. I do. If you really don't want to do anything more, just say the word. But I want you to know that I truly do want whatever this may be. To please you, for sure, and also more than a little for me as well. Something has awakened and I'm excited. I feel like I have had butterflies in my stomach ever since I decided to do this for you, for us. And I really like that feeling. To be honest, the genie has left the bottle and I'm not certain I want to put it back in. Is that ok?"

"Oh Hannah, yes, of course. With all this talk about me giving you orders, I don't know. I got worried that I may be pushing you to places you didn't want to go yourself. And if I had to be honest, I'm a little afraid of losing you and we really haven't done anything real. Flashing some guy in an airplane was hot but actually engaging someone to have sex with you is a scarier reality than I ever really gave thought to."

"Honey, I will never, ever leave you. There is no fucking way. I really want to push myself and ride out where this goes, but I don't see ANY future that doesn't include me growing old with you."

And with that, immediately, everything was ok. That little seed of doubt that had crept in was neutralized.

I went to kiss her and while she came in, she moved her mouth to the side and whispered in my ear, "oh, honey. Let's not forget my makeup, right?"

Damn, she was good. The irony here is that she doesn't wear a lot of make-up. She is very much a natural beauty with near flawless skin. Yes, she was wearing a bold red lipstick, but lipstick can be easily re-applied. She said exactly what needed to be said to calm my fears but then seamlessly shifted it right back into the game of denial.

She playfully slapped my ass as she took my hand and led me back to our towels.

We sat out and I worked to apply sunscreen over her body. She'd bake fast in this sun if we didn't. She applied some to me in return. We laid out and took in the rays. I'm not much of a sun bather and she knew that and came prepared.

"Honey, I brought your Kindle in case you get bored. I also got you some new... reading material."

My interest was piqued for sure, so I reached into her bag as casually as I could. Man, she is playing me like a fiddle. Sure enough, I found a nice selection of hotwife/cuckold novels and novellas that I had previously been too concerned to purchase for fear she'd see them. Works by KT Morrison, Kenny Wright, and others were in there. She did her best to hide her grin behind her big sunglasses and broad rimmed beach hat, but I caught it.

Time passed pretty quickly and my Apple Watch shared an alarm that she'd need to head back to our room or she'd be late to the massage appointment. I went to tell her and she was already getting herself together. Obviously she had set a reminder herself. When I went to get up, she stopped me.

"Oh honey, there's no need for you to come. You stay here and keep our spot. Enjoy the sun and your books. I'll come back out to join you or call you if I'd prefer you come back to me."

This was a twist I wasn't prepared for. My hope had been to watch her get her sensual massage.

"Oh no, you know me and sun bathing. I'd rather come back with you."

She stared at me from behind her big movie star sunglasses for a moment and the slid them down her nose slightly.

"Is there something I should know about this massage you have set up for me?" she asked knowingly.

I was so busted. Guys, fair warning that marrying a smart woman is both a great thing AND will also be the death of you.

I swallowed, nervous and stalling for time.

"Yeah. Ummm, I arranged for you to have a 'sensual massage', not just a simple rub down," I admitted to her.

I slight smile crossed her lips.

"I know. I figured that out. I was just wondering if you were planning on telling me or if you'd really let me get into it without knowing."

I blushed. So busted.

"Well, I hadn't thought you would want to know. I was afraid you might over think it."

"So tell me, who am I to meet in our room?"

"His name is Tré."

"And should I expect Tré to be a black man?"

"I think so."

"And what were you hoping that I would do with Tré? Did you think I would have sex with someone you'd paid to pleasure me?"

Shit. Did I? She made it sound sleezy. Crap, because it was kind of sleezy.

"Maybe?"

She simply nodded at my honesty, albeit a little late.

"Ok. So here's what's going to happen. I'm going up to our room. Alone. You'll stay here. But I'll give you what I promised you. I will do anything you tell me to do. So tell me, what do you want me to do with Tré?"

I didn't think, I just said, "I want you to do what you want to with him."

"Do you mean that?"

"Yes, absolutely. I will be ok with whatever that may be. It's your body, you are in control. But you are completely free to take things as far as you want."

"Good answer. Enjoy your reading. I don't expect to see you before my appointment is over. Understand?"

"Yes, ma'am."