It was a late October day. I was getting ready for a casual night out with some buddies after work at a local pizzeria. When I got to the bar, my friends were all a couple beers deep. It was not busy. The bar was a speakeasy type in the basement of the pizzeria. A cozy, private vibe.
There were some couples scattered throughout the tables and bar, our group, and one older woman sitting a few seats away from us at the bar. She was striking. It was tough to judge sitting down but she was on the shorter side and very fit. Dark hair and tan, smooth skin. Sitting legs crossed, with a whiskey, she wore 5 inch black heels, dark black pantyhose, a tight turquoise dress, and skeleton earrings. She was in the Halloween spirit. The red painted toe nails on her cute, small feet showed through the nylon.
Guys and girls are a lot different when it comes to sex. While a woman's good looks can carry her to a life of sexual gratification, for a man it's more than that. They need to be bold, loud, and confident. Unfortunately despite my 6'3" toned body and boyish good looks, I was a little shy. I had longish shaggy hair and a soccer player's body. Including a firm shapely butt. Suffice to say I got a little bit of butterflies when I made eye contact with the woman a couple seats down. Yet every time she turned the other way, I had to sneak looks at her nylon encased feet and legs.
Despite my slight advantage in the looks department, my friends were a bit more bold than me as they invited her into our conversation.
"Hey! I'm David how's it going?" yelled my large friend from the end of the bar.
"Hi boys. My friend brought me here then ditched me, so I've been better" she pouted, looking at David.
"No need to worry, you have a few new friends now" David said. He smiled and looked at Chris and myself who reciprocated welcoming smiles to our new friend.
"Perfect! How bout you have your cutie pie friend here refresh my drink?" She smiled, turned to me an looked me up and down. Was that hunger I saw in her eyes? Am I imagining this? The simple act of being talked about like I was below my more confident friend, of being ordered around caused a slight swell in my pants.
"You heard her, buy the woman a drink" David said as he and Chris snickered to hide their jealousy. Ok, so I wasn't imagining it. I hailed the bartender and ordered her another Old Fashioned.
We continued to chat and knock back a few drinks. Sarah was her name. She appeared to be paying special attention to me. Asking me questions about myself. Flirting with me despite the effort being put forth by Chris and David to reel her in for themselves. I felt like a prey being pursued. And I liked it.
"How bout some shuffleboard?" Chris suggested. We all thought that was a good idea and headed over to the table with our drinks. Sarah savvily suggested we go on opposite teams so that we could stand on the same side.
The game was tight. We were down 18-20 and I had the last shot of the round. A three would win the game. I was feeling calm and composed.. until Sarah stood behind me and covertly grabbed my ass hard and said "don't miss, cutie pie." Of course I become horny and flustered, blew the shot and she had the winning shot the next round. Sarah came up behind me and whispered in my ear, "I always end up on top." She flicked her tongue the inside of my ear.
By this point Chris and David could see what was going on. "We're gonna head out lovebirds. Sarah, can you take care of the boy for the rest of the night?"
"I won't let him get to any trouble, will I cutie?" she turned to me and put her fingers on my chin. I had no choice but to nod in the affirmative. She had such a powerful vibe about her. When Chris and David turned to go, she whispered to me "as long as you behave yourself" and grabbed my ass again. This time it was in clear view of a couple very good looking men who laughed at my expense.
"Be a good boy and buy us some drinks at the bar. I'll meet you there in a second."
Hearing the words good boy immediately sprang my boner back to life. She mesmerizingly walked to the bathroom. I performed as I was told, which for some reason I felt compelled to do with Sarah. On her way back, she stopped at the table with the two men who laughed. They exchanged some flirty looking exchanges, looked at me, laughed, then came back to sit next to me.
"So, since you're too cute and shy to bring it up, I'll talk about the dynamic we are going to have. We both know who is gonna wear the pants between us. I love boys like you. So attractive yet so submissive."
"I'm not submiss-"
"Shut up. You are submissive. Everybody in this bar can tell." She looked over at the two men who were eying us up and laughing still. "So here's the deal. I've had a bad day at work and my friend ditched me. And it just so happens I was looking for a new boy toy. So apparently the stars aligned when your sweet ass dropped right next to me. What's going to happen is you are going to drive me home and give me a massage on those feet you can't stop staring at tonight you pervert." She stared me in the eyes. I was stunned, confused, and so so horny. I couldn't agree fast enough.
"Yes ma'am you deserve it of course." The words felt so natural. She smiled and knew at that point I was totally in.
She paid our bill and handed me the keys to her Mercedes C Class. On our way home, she repositioned her body such that she was leaning on the car door and propped her feet up on my lap. In the bar I couldn't smell them, but dang! They glistened with a light layer of sweat on the nylon and smelled like she ran a 5k during the day. She saw me make a face that was a combination of pleasure and surprise.
