I walked up to the well dressed man in the perfectly fitted suit and smiled at him. He tipped his drink in my direction. “Hello there.” I felt completely out of my league here, but I knew the only way to find out if he might be interested was to try it. I refused to be the underdog who magically changed and got the guy. Instead I just let myself ooze a confidence that I didn’t always feel. I knew I wasn’t the usual picture of desire than many people thought they wanted, but ninety percent of the time, it worked and I got my guy or girl. He smiled and spoke, his voice deeper than I had anticipated. “Hi yourself.”
Taking a sip of my bourbon I smiled and opted for something cheesy and silly, hoping to make him laugh. “So what’s guy like you doing in a place like this?” as I gestured around the quiet, slightly seedy bar that was filled with a number of people having after work drinks, most of them dressed far more casually than either he or I. “I could ask you the same question.” “Nope. You first.”
“Well, I’m just in town for the weekend and this was the bar that an old friend and I used to spend our days at in college. I was hoping we could meet up again, but I’ve been stiffed it seems.” He laughed, shaking his head, “Probably because he found himself a hot guy to spend the night with instead.” I immediately wondered if I had misjudged my target, but I didn’t think so. “Now, why are you here Miss?” I blushed slightly and offered him a perfectly manicured hand (part of the confidence was looking the part you know), “Andrea. And this is my usual place to stop. It’s close to home and has one of the best whiskey collections in the city.” Another sip of my drink and another smile. “I didn’t get your name.” “Oh, I’m sorry. My name is Peter.” He grinned apologetically at me and signaled the bartender. “Another for me and another for the pretty lady here.” I finished my first drink just as the second arrived and I grinned cheekily at him. “So, what shall we drink to?” “Hmmm, I’ll drink to a gorgeous, curvy brunette with a sense of curiosity.” And he raised his glass as I giggled softly, “Well then I’ll drink to the cute blonde guy in the suit.” I raised my glass as well and we drank, both savoring the taste of our respective drinks.
We spent the evening flirting first subtly and not so subtly and after our fourth drink we both decided enough was enough. “Do you want to come back to my place?” I was direct and perhaps a little forward, leaning into him almost aggressively. He agreed, tucking a stray strand of hair back behind my ear. It was a simple gesture, but erotically charged after our flirting and I smiled. I expected him to be killer in bed and I hoped he could keep up with me.
We arrived at my small apartment laughing and talking about nothing important and as I shut the door and turned I found him right there. “I want to kiss you, Andrea.” I leaned against the front door and gave him a naughty grin. “And I want to do all manner of unspeakable things to you Peter. So I think it is safe for you to kiss me.” He leaned in and my lips met his, warm and soft, as I wrapped my arms around his broad shoulders. Even though I am not what one would call skinny he was physically larger than I was, although not imposing and he soon had me trapped against the door as we made out like a couple of horny teenagers.
He lifted my body against his and I was momentarily startled by his strength. Very few men would even try to pick me up like this. I found my legs wrapped around his waist, my skirt riding up my plump thighs to reveal the tops of my stockings. He pulled me closer and trailed kisses down my neck before murmuring in my ear, “Bedroom?” “Down the hallway, all the way to the back. And he carried me there, his hands kneading at my ass. “God, I want you.” He let me down, steadying me as I got my balance on my heels before I stripped to a matching purple satin bra and panty set. My plus size body was fully revealed to him and he smiled wolfishly, eating me up with his eyes before kissing me again, hungrily, needily. It didn’t take long before we were nude and in my bed, unable to keep our hands off each other. He wasn’t a perfect specimen, but his furry chest was warm against me and I reveled in the feel of his body. I could feel his cock and I reached down to stroke it taking pleasure in the look on his face when I did. “Don’t do that,” he rumbled, “or else you’ll have me popping like a teenage boy again. And I want to feel your pussy around me.” I gave a final squeeze and tossed him a condom from the bedside table.
I watched as he sheathed a thick, veiny cock and then pushed him back against the pile of pillows we had built up. Straddling him freely, my breasts and belly bounced as a rocked my hips against him, letting him fill (and feel!) me up. My hands rested on his shoulders as I rode him and his found my breasts, cupping them in his hands, letting the excess over flow. His head lowered to my nipples making me moan as he found out for himself just how sensitive they are. I moved fast, my breathing uneven and ragged as he teased me while I bounced on his cock.
Without warming he grunted and thrust himself against me and I could feel his twitching cock, which set off an orgasm of my own as I ground myself into him murmuring his name over and over. He held me close against him, unwilling to relinquish me quite so easily.
I smiled to myself, thinking how boring my night could’ve been had I not been willing to put myself out there and approach a complete stranger in a bar. It was all about being confident, something more people could stand to learn. I rested my head on Peter’s shoulder and kissed his neck. We might only share tonight, but I was going to make it a memorable one.