Bailey's Humiliation Games


I still had an "out" though, in the back of my mind. This was my game. If he didn't play by the rules I could call it off at any time. With that thought emboldening me I returned to the bar. The card was still tucked deeply in his pocket. I wondered if he'd looked. I surmised that he was the kind of guy who would could resist that temptation, though. By his demeanor, he didn't look like he'd changed any in the time that I'd been gone. If he'd read one of my humiliation cards, no doubt he'd be giving off a vibe that said so.

He motioned for the bartender to get us another round. I loudly told him no, I noticed that I slurred the words a bit. The alcohol was getting to me. It was also lowering my inhibitions, as well as enflaming my lust. All of it would come tumbling out. I turned towards Dan.

"No more drinks, buddy. If you don't want to play my game then fine," I huffed. "But, I'm not drinking anymore and if you don't want to play then I'll just go and leave you to your solitary drinking."

He was taken aback by my boldness at first. Then, he just leaned back and smiled. 'Feisty one, eh? I respect that. Fine. So your game is, I read the card, you do what it says?"

Suddenly, my anxiety returned. Why was I being so bold? He had the bad card, the humiliating one. I know what types of things I'd written on those cards. In a few moments I may be having to do one of those things.

"Oh, not so bold now?" He smirked. "Cat got your tongue?" He said as he lifted my chin so that I couldn't avoid his gaze.

"Don't worry, beautiful," He intoned deeply, "I have an idea that it might be something...erotic...I've never forced myself on a woman, and I wouldn't start now."

He saw my eyes pooled with tears of anxiety. He was evaluating me, measuring me.

The alcohol, the denial induced lust, and now the sheer power of his being made me make the final push.

"No sir, that's not my game," I said meekly. "Whatever it says on that card, I want you to promise me that you'll hold me to it. No exceptions. That's my game. I won't let you allow me to say no."

"Hmm," he said, as he stroked his chin. "Then it's as I suspected. Did someone put you up to this, a husband perchance?"

"No sir," I said. "Though the idea itself comes from an old lover of mine. I couldn't believe what I was revealing to him. "Please sir, just read the card, let me out of my misery," I begged. I knew he liked me begging. He also smiled every time I called him "sir."

"Turn your head," he instructed. I did as he said. I still watched him in the reflection of the bar mirror as he took out the card and read it to himself.

He chuckled. "Wow."

I burned in embarrassment, even though I didn't know exactly what it said.

"And you want to do this?" He asked.

"Yessss...." I hissed. "Whatever it is, make me do it."

"You mean you don't know what it is?" He said incredulously.

My head lowered in shame. "Not exactly..." I sputtered, trying to find the right words. "I know...the possibilities, just not the exact thing."

"Wow, this is really some game. I like this game," he chuckled. "And in a minute I'm going to love this game." I nodded submissively. He had me.

"What...what is it?" I managed to squeak out.

He grinned broadly. "I think you'll like it more if I reveal it in pieces."

I blushed absolutely crimson. He was a maestro.

"First, walk outside by yourself. You'll see a red Porsche parked on the outer row of the lot. I wouldn't want any lowlife types dinging my bumper, you know." He saw he had my interest. Get to my car, then, take off your panties, if a slut you like you is wearing any," he laughed, while watching me squirm under his gaze. "I'm guessing you like me talking to you like this," he asked with a gleam in his eye. I could only nod, stupidly.

"At the car, also take off that bra I see you wearing. Do not hide in any bushes or behind anything, in fact, take them off as you stand in front of my front bumper. Take both of those garments and lay them carefully across the ragtop, do not leave any scratches, or I'll start my own game with you, you understand?"

I nodded weakly. I could feel my knees weak like butter. I wondered if I'd be able to walk out of there at that point.

"Then, meet me around the back, in the alley."

I knew this part. This part made more sense to me. I'd written something like that on one of the cards. "But sir," I started to protest, "I know I didn't write anything about leaving my bra and panties..."

He cut me off. "No, not exactly, but it does get to your point. Think of them as souvenirs for me. You'll get what is on the card, you see?"

I could only nod submissively. "Ok, sir. Should I go now?"

"Yes," he answered with an air of certainty. "When you get back there, you'll know what to do," he said firmly. You want this, you want to do this right, don't you?" He asked rhetorically. "So go," he barked. He shoved the card back into my hand and sent me on my way.

I could feel the stares all bombarding me as I walked out of the bar. I swore that everyone could see inside my head at what I was about to do. I reached his car. It was under a light post. "Great," I whined to myself. "Even the gods like humiliating me," I thought.

I looked around nervously. The light seemed to spotlight me. I was just a exhibitionistic performance artist for the night. I slipped off my panties quickly. The bra was going to be more difficult. The only way to do it would be to take off my sweater first. I knew he knew that as well. I could only imagine him laughing at my discomfort. I pulled off my sweater and yanked off my bra in as much haste as I could muster. I managed to get the sweater back on just as a car went driving by. It honked on the way by. How much they saw I'll never know. I sighed one last time and I laid the garments carefully on the roof of his car as instructed. They were going to be his little trophies of the night, something to remember me by. I supposed it was only right. I knew what I was going to have to do now. I also knew that he'd never forget me after I did what I knew I was going to do for him.

I walked around to the back of the bar. It was a dirty alley. The dumpster's odor was foul as I turned the corner. I saw him standing in the shadows, smoking a cigar. He must've used the emergency exit. I wondered if it had alerted anyone else that we were back here. Suddenly I remembered the card I'd written and what I'd promised I would do. I still had some light from the parking lot illuminating me from behind. I knew he could see me. I started to peel off my sweater. My breasts popped out into the free air. I stopped only a moment to slide my skirt down, all the while being careful not let it touch the foul looking pavement, wet with stagnant water from a previous rain. I carried them and my purse in my hands as I approached him. I was nude except for my slut heels. I saw him smile as they click clacked towards him.

When I reached him he just nodded me down. I obeyed. I dropped to my knees on that cold, hard, nasty pavement.

"Take it out," he urged.

I unzipped his zipper and I freed his straining cock from his expensive pants. He didn't even unbutton his belt, he just let me take him in my mouth like that through the zipper hole. I'm sure he didn't want his expensive pants soiled by the filth on the ground. He was fully clothed, I was naked on my knees. It was just as I'd described on the card. I'd written it, he made sure I did it.

For an older man, his cock was surprisingly hard and thick. I gave him sloppy head while he ogled me from above. I'm sure he enjoyed watching the firm, ample tits sway in the night as my mouth devoured him. I knew he was getting a good look at my curvy ass too, as I worked my magic on him. I could hear people on the other side of the door. We were just outside the kitchen area. I wondered if any of them ever came out here on their breaks to smoke.

"Oh well," I said to myself as my mouth was filled with hard cock, "I'm here to be humiliated."

Thankfully, he didn't last too long before he began spurting his seed into my hot, willing mouth. I slurped it all up and kept it in my mouth as he shot, I wanted him to fill me, as I'd wished from my fantasy. I milked him for every drop until he started softening between my lips. Finally, I let his cock go with a soft "pop."

"Was that everything you wanted?" He managed to sputter as he regained his senses.

"Yes, sir. Thank you," I murmured submissively.

"Good," he said after regaining his control. "Now, one last thing. I think you'll like this, if you'll indulge me for a moment."

"Yes, sir. What is it?"

"I'm going to take your clothes and your keys..." he began.

He saw the panic in my eyes. "Hush," he barked quickly. "I said you'll like this. I'll take your clothes and your keys, you tell me which car is yours. I'll drop them off in your car. You wait here until you hear three taps on that door there. That'll mean I'm back and you can go."

"Oh god," I moaned.

"Humiliating....right?" He grinned mischievously.

"Very," I said with a shudder. "How can I be sure you'll leave them in my car?"

"Please," he said with some indignation. "Haven't I played your game exactly as you wanted it? Have I been anything but a man of my word?"

"No, sir," I agreed softly. "Do it, sir. I'll wait here. Please hurry."

It seemed like ten minutes as I waited back there in the semi-darkness. I kept looking for escape routes through the trees or behind the dumpster, just in case anyone else showed up. It didn't happen though. I heard the three taps and I nearly ran out of my heels getting back to my car. Luckily, he was true to his word, my clothes and my purse were all safely inside. I sighed in relief. I started the car and I went to grab my clothes. There was a note on top of them.

"If you would indulge me one last thing, my beautiful slut, drive home nude and when you reach home, wherever that may be, carry them in in your hot little hands. I think that would be humiliating. Also, if you ever feel the need to experience anything like this again feel free to contact me."

I saw he had left his business card. The humiliation card was next to it. I reread it, it said, "I'm going to suck your cock in the alley behind the bar. I'm going to be totally nude for you."

I tucked that card back into my purse. "Yes," I thought. "I'm going to have to return that one back to the jar," I giggled to myself.

My pussy was on fire. I considered going back into the bar and letting him take me to a hotel but I think he was probably spent and past being any good for me. I suppose I could've picked someone else up but I felt like I owed him his last request which was to drive home nude. I did as he asked.

I think he was right about it being humiliating. I cringed at each light I had to stop at. When I got home I wondered if any of my neighbors got a look at my naked, slutty ass as I fulfilled his last request to the letter. I had a real workout with my vibrator that night. I thought about making sure that from now on, I needed to leave wiggle room which would allow me to get satisfied as well but then I reasoned, correctly I believe, that the humiliation was the main purpose. Not getting off was just another possible humiliating outcome. I could get fucked any time. The humiliation was special. I came so hard on my vibe that night I swear I came in colors. I didn't know if I could wait very long for my next game.

{Look for further "Bailey" stories}

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