Under the Hawaiian Sun - Love Under Lockdown

“I’m going to Hawaii with my boss!” I blurt out.

It takes a few seconds to register, then she finally looks at me with interest.

“That’s great! What day are you leaving?” she asks excitedly, picking up her phone.

I sigh softly. No doubt she wants to tell her boyfriend when he can stay over. Still, at least she got a little bit excited about my news, even though it wasn’t for the reason I wanted.

I tell her that I’ll get back to her about that. She nods rapidly, then goes back to texting. I take my food and go into my bedroom. I need to relax.

I close the door behind me. My roommate never bothers me, but I feel the urge to lock it anyway, just in case. I set my food on the desk, then strip off my work clothes. Then I change into a nightie to be comfortable and flop on my bed.

I sigh contentedly, before I look at my TV and wonder if I should watch anything, but I decide not to. I close my eyes instead, and I see myself back at work. I’m watching my boss walk around, and I can feel his gaze burning back at me. Suddenly he calls me into his office and closes the door behind me.

I slide my fingers under my nightie and begin playing with myself. I imagine being in Randall’s office, and him pressing me up against the door. He slides his fingers inside of me to check if I am ready for him. I so am. With a smile he lifts my skirt and slides his cock inside of me. I bite my lip at the thought of how incredible it would feel to actually have that happen.

I continue to finger myself, all the while wishing that it was him. To have him take my virginity would be so hot. I’m rather embarrassed to still even have my virginity at the age of twenty. But I’d been so busy working my way up at the law firm – from receptionist in high school to legal assistant a year later and now to a paralegal – that I never had time to date.

Plus, guys my age were so immature. I wish that an older and more experienced guy like Randall would pop my cherry. I bet he has a big cock and that he’d be gentle at first, pushing it into me inch by inch, and then get rougher once I was used to it. Maybe he’d talk dirty to me and spank me for being such a bad girl.

The idea of that pushes me over the edge. I cum, thinking about Randall’s cock in my pussy instead of my fingers, and then I rearrange my nightie. I go to the bathroom across the hall to shower and think about it some more.

I can hear my roommate giggling from the other side of the apartment. She’s no doubt talking to her boyfriend on the phone. They’re probably laughing about all the fun they’ll have together once I’m gone.

That’s fine with me. I’d rather be with Randall in Hawaii, any day.

I make the water warmer and imagine my boss bending me over his desk. I don’t think I would be able to get enough of him being inside of me. I start to wonder exactly how big his cock is.

I blush at my thought and then go back to washing up. I shouldn’t be thinking things like that, but I can’t help myself. My love life is basically nonexistent, so daydreams are pretty much the only thing that I have going on right now.

As I rinse shampoo out of my hair, I wonder if I might meet someone in Hawaii. I laugh a little at that idea.

It’s always possible, but probably not. Good things like that don’t happen to me. I figure that the most that will happen is that I’ll end up hanging around the hotel, and probably sharing drinks with my boss, if I can get away with using my fake ID without anyone noticing, even him. I’m not sure he knows how old I am, so hopefully he won’t care if I drink.

Now there’s an interesting idea. Usually when people drink, exciting things follow, right?

I shake my head and turn off the water. There is no way anything like that would ever come to pass. Bosses and office workers don’t mix like that. Besides, people would start gossiping. I don’t want either of us to get in trouble. But I can still daydream about it, at least.

I finish up in the bathroom and go back to my room. Then I turn on my TV and watch a sitcom while I eat my food. I need the laughs to distract me – even though it’s a cheeseball one, with a fake laugh track, and I’m not a fan of those.