I sipped my drink and let my eyes dart back and forth between my phone and the entryway. I hadn't wanted to risk being late, so I tried to make sure to arrive 10 minutes early. Maybe I had just estimated the traffic wrong, maybe I had just been more eager for this meeting than I was prepared to admit to myself. I showed up almost 40 minutes ahead and schedule. I took my scotch to a booth in the back and did my best to be patient. I was nervous, but I tried to remind myself that the point of meeting in public this way was that, if things didn't go in a direction I liked, I could easily just stand up and walk away at any time. Moreover, I reminded myself, no one knew why I was really here. Well, almost no one.
I knew surprisingly little about the woman I was meeting. I'd never seen a picture of her and I'd never even be given a rough description of her, so while my eyes searched for her, I had to acknowledge the relative futility of the task. All I knew was that she was in her thirties, that she was very dominant, and that she was there to meet me. When a woman walked alone into the bar and started scanning, I felt my body tighten with anticipation. I wondered if I should wave, or make some kind of gesture, but when he scan came my way she locked into my instantly. I suddenly felt very exposed as she stared me down, a knowing smirk creeping across her face.
She moved quickly toward the table, like a predator that knew if had the advantage of a captive quarry. For a moment I felt myself panic as I things became real faster than I had expected. I felt very aware of the fact that they only exit to the bar was on the other side of the woman fastly approaching my booth. I expected her to take a seat in the booth across from me, but she stopped at the edge of the table and stood there, looking down on me as she spoke.
"You must be James," she said with a knowing smile.
I looked up into her eyes for just a moment, but I wasn't prepared for the intensity of her stare, and I gave in to the overwhelming urge to look down and away.
"Yes, I uh...I'm James." I replied and was greeted by silence, I realized why and quickly corrected myself. "Yes miss, I am james."
"Good boy James," she said as she put her fingers under my chin and tilted my face back to look at her. "Make room for me."
I had just expected that she would take the seat facing me on the other side of the booth, but the way she looked into my eyes had me obediently scooting over to make room for her before I had time to think about it. As she slid into place next to me, her hand went to my thigh with such a familiar casualness that I didn't even notice for half a moment. I felt her stroke up my leg and felt her eyes up and down my body. "Did you follow my instructions pet?"
"I thought...I thought you said it was optional miss." I replied as I felt my stomach tighten. She had instructed that, if I was feeling particularly brave, I should arrive for our first meeting without underwear on. I hadn't been feeling particularly brave when I had dressed to leave this evening.
She smiled and her hand stroked every close towards my cock. Even I was surprised about how hard it was already, just the way she was treating me: so bold, so assertive, so confident. "It was."
I relaxed for half a moment, but something about the way she had placed the emphasis on was lingered in my mind. The way she was raising her eyebrows at me made it evident that there was more to that phrase than I had realized. Then it clicked: it wasn't optional anymore. She saw the understanding register on my face.
"Go to the bathroom James, and when you come back you will hand me your underwear." she instructed softly but firmly, this wasn't a request.
I knew that if I did anything other than obey, this would be the end of the evening, and despite my mounting trepidation about all this, I wasn't prepared to let that happen.
"Yes miss," I said as I shifted in my seat, expecting her to stand so I could get out of the booth. But she didn't.
"No pet, I want you to crawl out under the table instead." She said with another wicked little smirk.
I hesitated for a moment, could she really be serious about that? She certainly was, I realized as I started to sink down lower and lower in the booth and slide underneath the table. I felt her gently caressing me with her feet as I crawled past her. I dared a glance to the side, hoping to peek up her skirt, but she closed her legs as if she somehow knew I was looking and wanted to deny me a glimpse of her. I crawled out from under the table and scurried to my feet.
"Oh and pet," she said as I headed towards the bathroom. "Bring a very girly drink back from the bar."
I couldn't feel my feet against the floor as I floated to the bathroom, dazed and dizzy. I was half walk to the bathroom by the time I realized that I was sporting a very obvious erection, but there was nothing I could do about that now. I tried my best to turn my body to hide it until I slipped past the swinging door to the men's room and hurried to one of the stalls. I clumsily unbuttoned my pants, dropped them, and tried to step out of them. I realized with embarrassment I hadn't taken off my shoes first, and I almost fell against the wall of the stall. I took off my shoes and stepped out of them, socks on the dirty bathroom floor. I slide off my pants and underwear, and separated the underwear from the pants. I pulled my pants back on and stuffed the underwear into my pocket.
I went to zip up, and I had to wrestle with my cock to get it back into my pants. Despite my efforts to avoid this, it quickly turned into me helplessly stroking my cock in a public bathroom. I stroked furiously, overwhelmed by how turned on I was by all this. I bit my lips as I felt myself start to go over the edge, but suddenly I panicked and stopped; my cock pulsing as it reluctantly backed away from the edge of an explosive orgasm. I realized that I had nothing to cum on, I was grateful I stopped myself before I was in a humiliating situation of cleaning up my mess from a bathroom floor with toilet paper. I waited a moment and collected myself, then zipped up and headed for the bar.
I tried to think of the girly drink I could, so when the bartender finally looked my way I ordered a fuzzy navel. I didn't even know what was in it, but it was all I could think of. I tried to make sure he saw me looking back at miss. For some reason I wanted him to know the drink wasn't for me, but he didn't seem to care either way. I took the drink back to the table where miss slid over to offer me the outside seat. I slid in next to her and her hand quickly returned to my thigh and leg, checking by touch that my underwear had disappeared. I remember her instructions and reached down to my pocket to pull out the underwear and pass it to her under the table.
"Good boy," she smiled and took my boxer shorts. She folded them once and placed them on the table where everyone could see.
"Miss, what are you doing?" I said with shock as she displayed my underwear for anyone who happened to look. She shot me a look the challenged me to dare speak like that again, and I fell silent.
"Drink your drink pet." she instructed with a gesture. I gave her a quizzical look, why was she pointing to the drink she asked me to bring her? And had she drank the rest of my scotch?
"Drink this?" I asked, confused but less confrontational.
