So I recently started a bar tending gig at this hotel downtown. I upgraded from waiting tables there to bar tending, as I just turned 21, and the tips really help with extra $$ for extracurricular activities. I'm in between boyfriends right now, as I like to say… and I've been so horny lately. When the bar is empty I like to fantasize about fucking one of the random business men who come in. I'm normally a shy, quiet kind of girl. I do chat up whoever comes up to bar, the basic customer service & small talk usually.
One night, early in the shift, I'm checking out the limited amount of male inventory.. I'm feeling a little more brave since I sneakily put a vodka tonic in my water bottle under the bar. I see a guy who kinda looks like my philosophy professor (whom I have a massive hot for teacher syndrome for) across the room. Mid-forties, 6' tall, brown hair, scruffy 5 o'clock shadow, his sleeves rolled up to show tan strong forearms. He walks up to the bar, holding his cellphone, distractedly texting someone. He looks a bit upset and orders a beer on tap. He barely looks up, like he can't be bother with the 'help'. I usually hate assholes like this. I ask him if he wants to start a tab, and he says no charge it to my room 760. He starts sipping his beer waiting for a reply it looks like and finally he makes eye contact with me. Or more like full body contact… he checks out my 5'7" self with perky B cups in my button up black shirt, and my big light brown eyes, black hair pulled up into pony tail. I smile, tilt my head a little and ask if he wants anything else.
He says, "What do you offer?" with smirk.
I say stupidly, "Whatever you want." I turn around and get on my tippy-toes to reach for a bottle on the high shelf behind me, pushing my ass out as much as possible. Someone's getting really good rum in their rum and coke even though they didn't order it.
"I'll tell you something, I asked someone to meet me here, but she's unavailable. If you meet me in my room after the bar closes I'd appreciate it." And he leaves a $100 bill under a key card. My heart is beating about 100x what it normally does. I'm thinking is this really going to happen? I just whisper out an "okay" and tuck the $ and card into my back pocket.
Now, I had about 6 hours until closing and then clean up. I'm not a prostitute I should not do this. I really shouldn't. But, God, a wanna a nice no strings attached fuck. I can close my eyes and pretend I'm fucking my philosophy professor. I don't drink any more, I completely sober up in the 6 hours and I've done the fastest clean up ever.
I rush to the locker rooms, do a quick wash up and put on a little red lipstick, add more eyeliner. Maybe I'll just see him and give him back the $100.
Up to the 7th floor I go. My palms are sweaty, my heart is racing. What am I going to find when I slide the key card in? Maybe he's a cop, maybe he's with my manager going to bust me for hooking. I slide the keycard into the slot, green light flashes, I turn the handle. It's kind of dark, standard very stark hotel room. First thing I see is the guy, OMG I don't even know his name, sitting in a chair in front of a desk. His laptop is open to a porn site, he closes it, and swivels the chair to face me. All his clothes are on but his cock is out and he's lightly stroking it. He smiles and says, "I thought you'd take the money and run. I was going to start without you, but as you can see I am excited to see you." His cock is glorious, thick, with a bulbous head. I feel mesmerized. I walk toward him, mouth watering, I love sucking cock. I get down on my knees and open my mouth and take in the tip. I inhale that lovely manly musk. His tip feels so soft and warm, a little spongy. I swirl my tongue around then take as much a I can down my throat. I get maybe half of it in before I gag.
He says, "Eager little girl, aren't you." I use my hands and mouth up and down wet with my saliva. He puts some pressure on the back of my head, leans back in the chair and slowly moans, "Fuck… that's nice". I work him for a few minutes. Before he says take all your clothes off and get on the bed.
He sees me pause and says, "You're new to this, huh? I gave you $100 don't worry you'll get the rest afterwards. Just take off your clothes and get on your hands and knees on the bed." My hands are shaking and I don't want him to see, so I turn to face the bed and start to slowly take off my shirt. He turns me back around and quickly unbuttons my shirt. I just have my black tank top and bra on underneath, I take those off. Then I toe off my shoes and I pull off my pants and underwear quickly, glancing at the puddle of my own juices in my underwear. I've been on edge for the passed 6 hours.
I climb onto the bed on all fours. My ass towards the bottom of the bed. He stuffs 2 fingers in my pussy without any warning. I let out a yelp and jump a little. But I immediately clench my pussy walls around his fingers in excitement. He fingers me fast, the tips of his fingers hitting my spot and he uses the thumb of his other hand to rub my clit. Fuck, I'm close already. I turn my head and tell him I'm going to cum. He steps back and brings the head of his cock to my opening, he rubs himself all over my juices. Then he slowly stuffs his cock in my pussy, it feels so good. That fucking big head of his cock, fills me up so well. He put his hands on my butt and peel the checks apart. I can tell he's watching his cock slide in and out of my pussy. Slow at first, savoring the first few thrusts. He hisses out, "Such a tight little cunt". I can hardly breath I want him to fuck me, and fuck me hard. Then he pull almost all the way out till just the head is in me, he grabs onto my ponytail and slams hard into me. I let out an "Oh my god". My mouth and my eyes are open wide. Then he starts pounding into me. Balls deep. I think I made the right choice. Oh my god I made the right choice. I feel that tingly sensation and cum so hard while his cock is deep in me. My legs are shaking and he fucks me right through my orgasm.
He pulls at my ponytail harder, bowing my back in to a C until I can just barely put the tips of my finger on the bed. Every now and then he'll slam into me and grind against me. So deep. So fucking deep. I'm practically whimpering. He says, "I'm going to cum on your back".
I can hardly form sentences my teeth feel like they're rattling. He starts pumping harder and I know he's going to cum. He lets out a growl and lets go of my ponytail I'm finally able to rest my elbows on the bed and feel him squirt his load all over my back. I take deep gulps of air, like I've been underwater.
He drops 3 $100 bills on the bed. He walks into the bathroom. I realize he never took off any of his clothes. I quickly get up and use my tank top to wipe my back up as best I can. I put my bra and button up back on, slide on my pants and panties, slip on my shoes. I leave the room still a little out of breath. I stand in the hallway for a moment getting my bearings. I don't know what I'm supposed to do. I take the stairs and go out the employee exit, throw away the dirty tank top. I get in a my car before it sinks in. I just had sex with a stranger and it was awesome. Plus I made $400. I wonder if he's going to be in town for a while.
Source: reddit.com/r/sexystories/comments/3r5uo2/hotel_bartender_mf