Halfway through my first whisky sour I started to relax a little. I almost forgot that I was tasked out by Sir for an unknown adventure. I kept expecting him to come out of the bathroom. About that time I felt a brush on my shoulder. “Excuse me Miss, is anyone sitting here?”. A man with sandy brown hair in his 30s flashed a teethy grin at me. I hoped this wasn’t who I was waiting for. He seemed to hope otherwise. I smiled back. “I am waiting for someone but you’re welcome to sit with me until they get here.” He offered to buy me a drink, which I accepted. We made small talk and I asked his favorite color. Holding my breath and waiting for his response was torture. His favorite color was blue and I let out a huge sigh of relief. I began to get bored with the conversation and he took a phone call and left. I spoke to several other people, two men and a woman. Two offered me drinks and at this point I was getting just a little tipsy.
I was starting to think the night was a bust and I locked eyes across the bar with him. He held my gaze as he walked over. His eyes were gray blue and incredibly intense. He seemed incredibly confident and I was already intrigued. He barely smiled and ordered me a water from the bartender without asking my thought on the matter. “Can’t have you off your game can we?” as he handed me the water. “You should drink this”. I obeyed without even considering how rude it might be to make assumptions about a stranger. He introduced himself as Grant and strangely, didn’t ask anything about me or why I might be half naked at a bar. He got straight to the point and asked if I had any questions for him. I was almost intimidated and realized I was half stammering when I asked his favorite color. “Brown, like chocolate pudding” he stared a hole through me and I suddenly felt like I had also lost the very small dress I was wearing. My hair was standing up all over my goose pimpled flesh. He held his hand out to me, “time to go doll, be a good girl and take my hand. I don’t want you stumbling on the way to the car.” I held my hand out and felt like my brain was spinning. Where was this man taking me. Who the hell was this man?
He led me to a very nice black sports car and opened the passenger door. I tried to hold my dress down while I stooped down to get in. He smirked like it mattered at all. Grant got in the driver’s seat and pulled a blindfold from his console. Sorry doll, you can’t see where we’re going. My stomach was churning and I was bordering on terrified. It was strangely exciting. We drove in silence for several minutes. Grant spoke at me instead of to me. “I assume you’ve done as you were instructed.” It was more a statement and he didn’t wait for a reply. “Pull your dress up to your waist”. I froze. Was he serious? I felt a hand jerk my knee over towards the gear shift. “Don’t make me repeat myself”. I did as I was told, almost shaking as I pulled and jerked at the fabric of my dress. This man was not my husband. No one else had touched me in 13 years. We had discussed so many fantasy situations and I was always game, but I could feel tears welling up in my eyes. “Spread your legs and lean back”. Again I did as I was told and as I leaned I was instantly reminded of the large plug still occupying my ass. I inhaled sharply. I felt fingers, warm and long, pulling my pussy lips apart. I gasped as two of them slid quickly in and back out. I was drenched.
Suddenly and forcefully the fingers were being shoved in my mouth. “Can you taste yourself and tell me you aren’t excited? I’m going to have to get my car seat cleaned you little slut”. I felt my face turning red. Grant chuckled. “Your face isn’t the only thing that’s going to be red tonight. I want you to pull your pussy lips apart and you will hold them open until we get to our destination”. I reached down and could hardly hold on to my lips without my fingers sliding off of them. I still couldn’t see where we were and had no idea how long we had driven. The first slap from his open hand hit my exposed pussy and I gasped for air. “You will call me Master Grant. Tell me you understand and thank me for slapping your sweet pussy.” “Th…Thank you Master Grant. Yes, I…I understand.” He stroked my throbbing pussy. “Good girl”.
Part 3???
Source: reddit.com/r/eroticliterature/comments/pmx7lw/the_date_planner_part_2
Please write part 3.