Chapter 2 - Mike
Staring out over the ocean from my cabin window, I wonder what Willow is doing.
I arrived on the boat this morning after an overnight flight, so I’m still jet lagged, but already I can tell this cruise is going to be a little different from ones I’ve taken in the past.
Every year, my company sends me on this cruise.
It’s part work and part reward. We provide the entertainment for the ship—musical acts, comedians, and such—and I’m there to check that everything is going okay from the point of view of an average customer.
No one knows I work for the company, so they don’t treat me special.
So every December, I go on a three-week singles cruise around the Caribbean, and while I’m there, I enjoy casual hook ups with other like-minded people. I may be getting on in years, but on the ship, there’s usually no shortage of women who’re looking for an older dom to fool around with.
On previous trips, I’ve been able to relax and enjoy myself. But this year, I can tell there’s going to be a problem.
The problem is Willow.
Within half an hour of getting on the boat, a woman hit on me—long blond hair, tanned body in a tiny bikini, emerald eyes. She’s stunning, and she invited me to her cabin to rail her senseless.
But I said no.
I surprised myself, not knowing I was going to say it even as I opened my mouth. But as soon as the word was out, I knew I said the right thing.
As hot as this woman was, she wasn’t Willow.
After that, I saw a lot of women that normally I would try to screw, but I knew in my heart of hearts that it would be meaningless fun. Because I would be thinking of Willow the entire time.
I don’t know what it is about her that’s gotten under my skin. She’s gorgeous and sexy, but there’s something more than that.
For the first time in a long time, I’m comfortable around someone.
It’s not just the sex. When we cuddled up on the sofa, I wanted her to rest her head on my chest and feel her hand in mine.
Or when we woke in the morning, cuddling up in each other’s arms felt like a treat rather than something I should do before sending her on her way.
I want to spend time with her rather than going back to my usual self-inflicted isolation.
This is the first time since my wife has died that I want to have a relationship with someone. I’m not saying dating, but something more than fuck buddies.
My phone buzzes, and I glance at the screen. It’s a message from Willow. I’d just sent her a picture of the view from my cabin.
Willow:
Oh, very nice. But you know the view I want to see.
She signs it with a winking emoji. I’m old-fashioned with my texting and rarely send hearts or funny GIFs. But when she does it, it makes me smile.
I snap a picture of myself, giving her my best dom pose.
She replies almost instantly.
Willow:
Are you shirtless?
Mike:
Yes. I’m heading to bed.
I climb into bed as I wait for her reply. One of the advantages of an all-expenses-paid trip is that I get a decent-sized cabin with a luxurious bed. It’s as soft as a cloud and my eyes are already starting to close.
The ping from my phone brings me back and I check Willow’s message.
Willow:
So, you’re completely naked then?
Mike:
Yes.
I wonder where she is while she’s messaging me. Probably in that depressing apartment. I hate to think of her there, especially when I’m in such nice surroundings.
Willow:
Hmm, how can I believe you? Maybe you need to prove you’re naked.
She’s certainly less shy than when we first met. I can’t imagine that woman asking to see me naked. But just because she’s coming out of her shell doesn’t mean I won’t make her work for it.
Mike:
Where are you?
Willow:
At home.
With one hand I type a message to her, while with the other I wrap my fingers around my cock and gently stroke. The dom side of me has woken up and is ready to play.
Mike:
Go to your bed and get naked. I want you under the covers and ready for me.
There’s no waiting for a reply. She sends an instant, “Yes, Sir.”
My cock grows in my grasp as I imagine her rushing to the bedroom and throwing off her clothes. I smile as I think about her tits bouncing as she leaps into the bed and gets under the covers. I bet she’s excited and has an adorable grin.
Willow:
I’m in bed.
Mike:
Good girl. Now, tell me what picture you want.
Willow:
I want to see you naked.
Mike:
No, that’s not what you want. What is it you really want?
There’s a pause and I remember that even though she’s becoming bolder, she’s still a rather shy sub. But then I get her reply.
Willow:
I want to see your cock. I want to see you hard for me.
Now that’s my good girl.
Mike:
Slip your hand between your legs and touch yourself. I want you fuzzy and wet before I send you anything. Understand?
Willow:
Y
Whenever she gets turned on, her replies get shorter, either from rushing or because her head gets foggy and she can’t form the words. It’s how I can tell if she’s into what I’m doing.
I pull down the covers and angle the phone at my cock, making sure that the curve is visible. Willow likes the curve; she says that it hits the perfect spot. I believe it based on how it makes her moan.
I make sure the picture is clear and hit send.
It’s a little strange for me, as I’m not into taking dick pics.
When I was with my wife, it wasn’t a thing.
And now that I’m single, I don’t normally stay with anyone long enough to send pictures back and forth.
I’ve only done it a few times, and this one looks impressive.
My phone pings again.
Willow:
Oh. That’s hard, and the tip is so red. Your hand is really wrapped around it.
Mike:
Red and hard for you. Now I want you to lie back in your bed and rub your pussy. Give your clit attention and imagine it’s me rubbing circles against it. I want you to think of me watching you. And you’re going to send me a picture to show me how turned on you are.
It takes a few minutes before she replies, and I sit there stroking my cock while I wait.
I can picture her, head back and legs wide open.
Her fingers inside her pussy as she imagines me watching her from the end of the bed.
Maybe when I get back I should do that. Get her to put on a show for me and tell her that if it’s good enough, she can have my cum.
I’m sure that would be the right incentive for her.
Her reply comes back and I open the picture.
She’s lying on her back holding her phone camera above her, wearing a gorgeous black lingerie set with her breasts spilling out the top.
Her eyes are shut and her mouth is slightly open.
I can’t see where her other hand is, but I’m pretty sure it’s between her legs.
This is the first time I’ve asked her for a picture, and she sent it without question. Not only is that a sign of a good sub, but also that she trusts me.
As I focus on the picture, I stroke myself harder and some pre-cum leaks out. I wish Willow were here to lick it and swirl her tongue around the tip, then look me in the eyes as she swallows.
Mike:
I want you to lift your finger to your mouth and suck it. Taste yourself and imagine how good it’ll be when I’m there and eating out your pussy. Now I want you to take that finger and rest it against your clit. Can you do that for me?
Willow:
Y
Mike:
Rub your clit, round and round. Nice and slow so that it makes your mind all empty. I want you to get soaking wet. And Willow...
Willow:
Yes?
Mike:
No coming till I give you permission. That’s for the entire trip.
All thoughts of sleep are now gone. My sweet submissive is in bed, ready to do whatever I want and fuck herself following my commands. If this is how every night is going to go, maybe this cruise won’t be so bad after all.