Kinky Meet Cute

I'd once heard that women decide if they will sleep with a man within three minutes of meeting him. And that was the case the first time I had sex with a stranger—the first time I met you—I knew within minutes.

A few years ago I was in Chicago on a trip for work, my colleagues had left earlier that evening, and I found myself in the hotel bar, nursing a vodka tonic alone. This particular bar was fairly small, placed in front of the entrance to the hotel's pricy restaurant. I saw you in the long mirror that ran the length of the old oak bar, a tall figure with broad shoulders, dark eyes, dark hair. I always was a sucker for tall, dark and handsome in a suit. I watched you order a drink, something manly that came in a low tumbler, nothing pink served in a frosted martini glass for you. I saw you glance my way, eyes lingering on my legs, "Excuse me, mind if I join you?" gesturing to the empty seat next to me.

"Not at all," I replied. Giving you a small smile, I slowly swiveled my chair around to face you, my legs crossed, my black dress clinging, glad I had touched up my makeup before leaving my hotel room. Looking you up and down—taking in the dark hair, the casual way you wore your suit, the drink served neat—I said, "Let me guess: your name is Don Draper?".

"If it was, that would make you Joan Holloway," you immediately shot back.

"But in the show, Joan never sleeps with Don," I pointed out.

"Well, that's true. But he should have," you said, while signaling for the bartender to pour another round. "And if you don't mind me saying, you certainly have the figure—and the style—for the role." Leaning a little closer—as if you were about to tell me a secret—your voice became a little lower, as you told me, "You know, I've always loved seeing a woman wearing seamed stockings—something about how they frame the legs—how they disappear into that little square bit at the heel, like they're teasing me. Making me want to take off that heel and follow the seam down to the tips of your toes."

I took a long sip of my fresh drink. I could hear the trace of an accent in your voice, something southern, but not the harsh and twangy accent of my childhood, something smoother and more costal. You saw my eyes flicker down to the gold wedding ring on your left hand, wondering where this was going. Up close I could see that you were older than me—late thirties or well maintained forties— and your hair was starting to go gray around the temples, with laugh lines crinkling out from the corners of your eyes. I liked what I saw. "I don't usually have conversations like this with married men I don't know," I told you.

"Oh, so just the single guys you don't know?" you replied, giving me a knowing look.

"No, just the married men I do know," I laughed, as you watched me.

Still staring at me, you took a sip of your drink before teasing, "Just remember, anytime you want to stop, the safety word is rhinoceros." I knew you were joking but I couldn't help replying, my mouth opening before my filter could kick in, "Actually my safety word is red. I usually use the red, yellow, green system. It cuts down on confusion."

"Now Joanie," you said, "you know it's not nice to tease a man. Especially a man like me who's been traveling for work a lot lately, and feeling a little lonely and a little frustrated—and who finds you incredibly sexy".

I suddenly felt flushed, and couldn't tell if it was from the vodka or the way you looked at me. Feeling as if it was someone else speaking, I said, "No Don, I never joke about men or kink. And I'm feeling a little lonely and frustrated too." I downed the rest of my drink and, after a moment, slipped my room key into your breast pocket. I whispered into your ear, "I want you to finger me until I cum all over your wedding ring," before leaving you to take care of the tab.

Back in my hotel room, I freshened up my lip-gloss and smoothed my black dress down over my hips. I straightened my stockings and with a sigh and slipped off my pumps to sit and wait for you, my stomach in knots. That's how you found me, legs demurely crossed, head whipping up when I heard the soft click of the door unlocking.

I remember you looming over me, reaching down to pull me up so that I was standing in front of you. Forcing me to stand on tip-toe as you placed my arms around your neck. I don't know how long we stood like that, my arms around your neck, your hands running up and down my back, over the curves of my hips and down to squeeze my ass. You pressed yourself against me, letting me feel how hard your cock already was, as you hands greedily touched each new part of me.

Eventually, you led me to the bed, pulling me down on top of you. With my legs straddling you, I could feel your hard cock pressed up against my cunt. You undid the buttons of my dress, letting my breasts spill out, cupping them and making my nipples ache as you squeezed them. You kissed me, wrapping your hand around the back of my neck to pull me to you, while I moaned into your mouth and moved my hips, slowly, back and forth. We did that a long time, until I was panting, making small keening sounds and pulling at your hair. Your kisses became more demanding, more cruel and insistent as you rocked me harder and harder against your cock.

You could feel how wet you were making me, how close I was to cumming just from the feel of your hands and the friction of my pussy rubbing over the fabric covering your cock. You gave me a little smile, saying "Not yet baby. You're going to have to earn the right to cum." That's when you pushed me off of you, stood up, sat down in the chair facing the bed and told me to "be a good girl and undo Daddy's belt".

I sank to my knees between your legs, proud that my hands were steady as I undid your belt, pulled down your zipper and watched as your huge cock sprang out. I remember bits and pieces from the those first moments: how turned on it made me to hear you call yourself "Daddy", how your head tipped back as you looked down at me with heavy lidded eyes, the sound you made when I grasped your cock and opened my mouth to kiss it, and the way you bit your lip when I wrapped my lips around it. Your smile and groan as I began to slowly bob my head up and down, taking more and more of your cock into my mouth each time. My panties grew wetter the longer my lips spent wrapped around your cock. I felt your hands in my hair. Gently combing your fingers through it at first, then beginning to guide me with more and more insistence.

"No hands," you said, your voice low and more demanding with each thrust. "Give Daddy what he needs. Give me your mouth." Nodding my head, I let my hands drop to your knees, my fingers gripping the wool of your slacks as you began fucking my face. With each lick — each gulp, each gasp — I could feel myself slipping more and more into who I now was: your toy, your filthy, perfect, seductive plaything.

My eyes never left yours as your fingers tightened in my hair and you started thrusting up into my open mouth. As the saliva began to pool and run down your cock, as my throat opened up to take more and more of you into me, as your breath quickened, as my moans became louder, as I began gagging when you forced another inch inside of me and my eyes teared up and my mascara began to run, you told me, "Take it. Take every fucking inch of your Daddy's cock. You love it don't you? You love having your mouth wrapped around my cock? You love feeling me filling your throat and the taste of my precum on your tongue, don't you? I own you baby. Don't I? Yes, that's right, I own you. Now make your Daddy cum and don't you dare spill a fucking drop."

You stilled, your hands pulling me down even farther, forcing your cock even deeper into my mouth, deeper than any other cock I'd ever sucked. For a second, your eyes closed and I felt your cum shooting down my throat, overflowing to run down your cock as your hips jerked and you let out one long groan.

You slowly loosened your hold on my hair, letting your hand rest on my temple, fingers making slow soothing circles. Watching as I pumped your cock, my tongue lapping up every drop of cum, making you shudder and groan one last time.

"Show me," you said. "Be a good girl and show me your reward."

Like a good girl, I opened up my mouth, some of the cum running down my chin to drip down onto my chest. And with your eyes never leaving mine, I swallowed saying, "Thank you Daddy".