I've had a thing for my boss Harry for as long as we've been working together. Maybe it's a power thing, maybe it's desiring the unattainable, but I've harbored a crush on him for years now. I work insanely hard, pulling long hours, but it's mostly to impress him, and because I enjoy doing what he tells me to. I admit that I am not subtle with how I feel about him. I never let my coworkers badmouth him, and I act incredibly submissive towards him, even though I usually hate being told what to do.
In my defense though, he is very hard to resist. He is flirting with me constantly, always sneaking up behind me to whisper in my ear and scare me, or taking every possible opportunity to tease me. He will joke about punishing me while holding something like a paddle, or wink at me from across the room so fast I think I must have imagined it, and once he called me "little one".
A little about Harry, he is six foot two and gorgeous, and ten years older than me. He is balding but keeps his hair shaved close, and he has the most intense dark eyes I've ever seen. He has a New York accent, and a great sense of humor. He is very charismatic and charming, but a lot of people at work don't like him. He can be pretty demanding and sometimes makes people cry and/or quit. He never gives me a hard time though, probably because I am quick to do what he tells me to. I go to him whenever I need something despite having multiple superiors, because he always gives me what I want and never gets mad at me.
The only time he actually did give me a hard time was when I tried to date another guy at work named Lucas for a couple months. We would go to lunch together and talk at work a lot. I tried to keep our relationship a secret, but Lucas made no such attempt and word quickly spread. Harry's attitude towards me changed immediately. He made a rule that I could not go on lunch at the same time as Lucas, and would get mad if he saw us talking together at work. He gave poor Lucas a really hard time, picking on him for every little thing and even threatening physical violence until Lucas cursed him out then quit. Not long after that, he moved away and we stopped seeing each other.
As for me, I am thirty-five but look much younger, like early twenties. I don't smoke or drink, and I take care to stay out of the sun without sunblock, so I was able to avoid wrinkles. I don't want to describe myself too much, as everything I said up until this point is true and I don't want to be identified.
Today we are all on an overnight business trip. I worked my butt off to make sure I was chosen to attend. They are putting us up at a decent hotel for the night. They keep us busy with meetings all day, and meals in the hotel restaurant are provided.
During the meetings and lunch I can't keep my eyes off of Harry. When he catches me watching him, my eyes flicker away. Multiple times I look up and see his eyes on me too. His eyes are so intense and deep, I catch my breath each time.
At dinner I get there a bit late, and one of the last seats is next to Harry. I nervously drop into the chair and smile at him. Throughout the dinner, I manage to drop my fork under the table twice and spill my water. I was mortified! It flows over to his side, so I hurry to mop it up with my napkin before it got his clothes wet. He stands up with an extremely irritated look on his face until I get it mostly wiped up. Total disaster.
I heard that all the VPs get their own room, so I make a plan. I may never get this chance again. I follow Harry after dinner to find out his room number, peeking around the corner until he goes in a room, then I run over to the room to see the number, it's 223. I sneak off. It's not time yet.
I go back to where I'm rooming with some other girls I work with, and I hog the bathroom for over an hour, showering, shaving, fixing my hair, even blow drying it and putting on some light make-up. I leave my hair down with loose curls around my shoulders, and twist two pieces to tie together in the back for a delicate feminine look. Every inch of my skin is soft and smooth. It's a good time for my new purple lacy bra and panty set. I put on a blue tank top, some comfy capri leggings that show off my ass, and my rainbow tie-dye slip-ons, because it's such a warm night.
I claim I'm getting a drink, and ask the girls to cover for me a bit before midnight. I slip out and buy a six pack from the hotel bar, then bring it up to room 223. I knock softly, my face burning from embarrassment and feeling a bit light-headed from my heart pounding so fast. What if he gets angry I came? I could get fired. A few seconds pass before the door opens.
Harry raises an eyebrow at the sight of me. He is wearing a t-shirt and pajama pants, and I admire how sexy he could look dressed so simply. I hold up the Heineken, I remembered he liked it from a picture on his Facebook. "I brought you a six pack." An unspoken offering he is free to refuse hangs in the air.
"Get in here before someone sees you," he mutters, grabbing my arm and pulling me in, shutting the door quickly behind me. He puts up the chain lock, then takes the beer from me, and sets it on a small table, his eyes holding me in place.
"You just don't give up, do you?" Harry presses me up against the door with his chest. His face is inches from mine. He grabs both my slim wrists and pins them above my head with one hand.
"I'm sorry, I just thought--" I whisper before he cuts me off by wrapping his hand tightly around my neck. I could still breathe, but my breaths are coming out shallow and light. He towers over my frame, leaning even closer. I could feel his upper body pressing against mine. My head comes to his chin, so I have to strain my neck to look up at him.
"You're going to be a good girl and do what you're told tonight, understand? I know what you need and I'm going to give it to you. Say 'Yes, Master'," Harry's velvety smooth voice rolls over me, putting me in a trance-like state. He lets go of my neck so I could reply, and runs his hand soothingly up and down my bare arm. Goosebumps spring up at his light touch.
"Yes, Master," I say softly, drinking in the opportunity to gaze at his face up close and take in every detail. He has a strong nose and chin from his Mediterranean heritage, and a neatly trimmed goatee, although the times I have seen him not shave for a week or so, I think he looks even better. He has nice skin and has honestly only gotten more sexy as he has aged. My eyes land on his slightly thin lips, and my tongue slides along my own lips, tasting my vanilla lip balm as I imagine what it would be like to kiss him.
Harry releases my wrists and grabs one of the beers I brought. He walks over to the couch and cracks it open as he sits down. He pats the spot next to him and smiles. "Come sit with me and keep me company while I drink this. None for you though, I want you aware."
"Yes, Master," I trot over to the couch and sit in the spot indicated for me. Harry immediately puts a hand possessively on my inner thigh, and strokes his fingers up and down while I attempt to sit primly.
"Good girl," Harry nods approvingly, giving my upper thigh a squeeze before letting go. He grabs the remote and flicks on the TV, putting on some action movie, then casually puts his hand in his pajama pants and starts stroking his dick.
I stare down at him stroking, my eyes wide. Harry grins and leans over to whisper in my ear, "What are you staring at? Do you want this dick, little one?" his warm breath making me shiver. I swallow and nod, not trusting myself to speak. "Get on your knees in front of me." He spreads his legs to make room for me on the floor, and takes a long swig of his Heineken.
"Yes, Master," I drop down and crawl between his knees, and reach for the bulge in front of my face. His pants are really loose, so I slide my hand into them and my hand closes around his semi-hard dick. Harry's fingers slip into my hair, and he gently pulls me closer to him. I pull his dick out of his pants and study it for the first time as I lightly stroke it. It has a fat head and it's a nice size, thick and smooth as it gets harder.
"Suck it," Harry maintains a tight grip in my hair, and keeps pulling me closer until my mouth is closed around the end of his dick. I swirl my tongue around the head, then suck it in deeper as Harry starts a rhythm, forcing my head up and down as he begins face-fucking me.
I don't have much control over the blowjob as Harry holds my hair tightly and keeps shoving his dick deeper in my mouth as I choke and drool all over it. I try my best though, to lick and suck lovingly, desperate to make him feel good.
