tagBDSMBailey's Humiliation Games

Bailey's Humiliation Games


{Part one of "Bailey's humiliation games"}

"I can't believe I'm doing this...again," I thought as I approached him. I had the fateful three cards in my hand. Who was he? I had no idea. But, in just a few moments I knew I could be doing something crazy and humiliating with him. I'd done it before, more than a couple times. I call them the "humiliation games." That's what they are. Purposeful, intentional ways for me to humiliate myself.

I'm Bailey. I'm that mix of girl next door and feisty sass. The men at the bar I work think I'm a cutie, at least I hear that all the time. I'm also a tease, a flirt and, unbeknownst to them, I'm a sexual kinkster. I have managed to keep that part of me unknown to those who know me. Any day though, with the things I make myself do, that could come to an end.

I learned this part of me through John, a mentor, if you will. He actually was an older guy who introduced me to things like bondage, exhibition, and Ds. Ah yes, the Ds. It's the submission to the whims of another that he drew out of me. He actually introduced me to the idea of the games of humiliation.

I was intrigued by the feelings I was having as he showed me how it could be. The submission was like a drug. Little by little we both realized what I seemed to enjoy the most was the embarrassment. It was the shame of having to face the fact that I enjoy things that many others would cringe at, or even flat out reject. He showed me things about myself I didn't know, like the feeling I'd get when he'd show me off to others. It was things like flashing people or being naked in the car. I can't accurately describe the feelings I would get being seen by complete strangers that way, how horny it would make me.

It graduated quickly to sharing me with others. Most often, it was the "stranger at a bar," thing. For example, he'd instruct me on what he wanted me to wear, what to say or do. Then, he'd sit across the room and watch me humiliate myself by doing them. More than a few times it ended with me sucking on some strange guy's cock, or, not quite as often, it ended with me getting fucked in some sleazy hotel room.

It's hard to describe but, it wasn't really the actual sex that was the real turn-on. Instead, it was the submission to it, the "being made to do it," aspect. The humiliation became like foreplay for us and it always ended with a wild fuck session afterwards between John and I. We both discovered how much I liked the embarrassment of being such a "dirty girl."

Sadly, at the time, John was estranged from his wife. Eventually, though, they reconciled. It was just before he went back to his wife he introduced the idea of the games of humiliation. He wanted me to continue with it, knowing how much I enjoyed it. He knew he couldn't be there for me. He knew how headstrong I am and he knew I'd never back down from a "dare" even if it came from my own mind. Thus, he basically left me with a game he knew I'd play, since he came up with it, as sort of a challenge between us.

His basic idea got me started on the path I'm on now. It lead me to tonight, with me approaching the middle aged business man at the bar. I didn't even know what was in store for me, that was the beauty, or cruelty of the game.

His simple idea was this, I'd make out three index cards. On one card I'd write something basic, such as, "can I buy you a drink?" or something innocuous like that. On the second card I'd write something mildly bold or risqué, such as, "one free kiss," or "how do you like my bra?" (if I wasn't wearing one, in order to let him have a lingering look). The third card of course was something totally embarrassing, especially when you remember that it gets seen by a complete stranger. I call it the "humiliation card."

The last few times I was with John and we went to a bar, he had me play the game. The first two times the stranger picked the "tame" card. I bought the guy a drink and, it wasn't a total loss, I ended up getting one of the guy's numbers and ended up fucking him at a later point. The third time was the first of what now is the frequent occurrence of the of humiliation card.

Part of the embarrassment that is built into the game is that even I don't know what's on each card. I make a pile of "tame" cards and keep them in one jar. I make another pile of "mild" cards and keep them in a different jar. And lastly I made a bunch of "humiliation" cards. When I get ready to go out, I randomly pick one card from each jar and put them in my purse without looking at them. So, imagine my surprise when on the third occasion with John I saw the stranger's eyes light up when he read the card.

I'm sure I was blushing profoundly. He asked, "are you sure about this?"

I remember gulping, wondering myself what was written on that card and why on earth I had agreed to do whatever it said on there.

"That depends," I said hesitatingly while avoiding his gaze. "What does it say?"

He smiled lewdly. "It says, "five free minutes of fondling, no restrictions."

I nearly choked. He could see my face, scarlet with heat. He stood there with a leer and a wide grin. He was young, cocky, he immediately took control of the situation. I think that's why John picked him for me to approach. He sensed that this guy would know what to do with such an opportunity.

"Well?" He asked smugly. "Where do you want to do this?"

I kept my eyes down and I shrugged at first in defiance but after shooting a glance at John I knew what I was to do. I motioned over towards the hallway with led to the bathrooms. " Over there?" I said with failing confidence.

"Hehe, sure thing, toots," he laughed cruelly.

I hated him already but I knew deep inside that he was the type that this game was made for. I'd surely get that treatment I seem to crave. He led me by the arm past curious onlookers. He was parading me, his smile was wide and arrogant. He was showing me off, like I was his prized kill. I caught the glimpses of a few of the patrons who were watching me intently. I was braless. I had on a white top which, under certain light conditions was transparent enough to show off what I had. I had on a skirt which showed off plenty of leg, and I had on some pumps which clearly indicated what kind of girl I was that night.

We arrived just outside the women's bathroom which was at the end of the hall. I thought it was a good place because, from what I could tell, there weren't many women in the bar at the time so there was less chance of being interrupted. I could see his smugness, his virility coming out. I couldn't help but wonder what he was like in bed, what his cock was like.

"Five minutes?" He huffed. "What if you want more than that?" he cackled. His blunt reply snapped me out of my musings.

"Five minutes," I said with more firmness, I felt some power returning. I could be in control, it was just going to be his hands. I could do it, I could take this, for John, for our game.

"No restrictions?" He said more urgently. I could see the fire starting to burn within him.

I'm not sure if John had thought this out or whether this was just another part of the humiliation of it, that he wanted me to have to deal with the vaguery of the rules myself. I was burning with embarrassment, but, as always happens to me in these types of situations, I was already wet. In my head I cursed my uncontrolled lust. I nodded meekly to him.

"No..." I mumbled softly, "just no pain."

He laughed at that. His eyes were on fire now, they were burning holes in my top. He hadn't stopped leering at them since we turned the corner. He looked around nervously.

"I really don't want to be interrupted," he said.

He suddenly pushed me into the women's bathroom. He bolted the door behind us. I started to protest. He shushed me. "Five minutes," he reminded me. "Starting...now," he said, pointing at my watch as he pushed me back against the wall.

His hands immediately went to my top. Instead of wasting time unbuttoning it he just yanked it up over my head, leaving me topless in front of him. I shuddered as his hands attacked my tits, My nipples were already firm with excitement. He leaned in and kissed me deeply. I didn't expect it, though, I didn't really know what to expect at that point. I didn't stop him, the words, "no restrictions," kept invading my thoughts. His tongue darted and danced with mine.

He pulled off long enough to gloat, "yeah, I knew you were into it, too."

He was mauling my tits, he didn't want to waste a precious moment. Then, it was as if he realized there was more to explore. His hands found my ass and he began massaging my cheeks. He pulled up my skirt and his hands slid inside my panties. He pushed them down to my ankles unceremoniously. I was standing there being pawed by a complete stranger, topless, my panties around my ankles and my skirt pulled up lewdly over my now bare ass.

It only took him a moment before his finger traced rudely over my asshole. He pushed against it teasingly, as if he was going to finger fuck me there. Instead he just laughed and continued on. His other hand was around front and I gasped as I felt his fingers find my pussy. I blushed again when I realized how wet I was down there.

He knew it too, he just grunted, "mmm, hot little whore," as his fingers found their way up inside my pussy.

I was groaning, I mean, he was an extremely good looking guy, and he was touching me in all the right spots, I couldn't help but wonder again what his cock looked like, how it felt. He had two fingers inside my pussy now and he was almost lifting me onto my toes each time he rammed them back up inside me. He was taunting me.

"Yeah, look at how wet you are, look at you, fucking back onto my fingers, yeah, that's it, fuck yourself on my fingers."

He made me do it. I had to grind myself onto his fingers while he held them still. It was embarrassing, he was making me humiliate myself. God help me, I couldn't stop myself, I came all over his fingers. I slumped against him as his hands had their way with me however he wanted. I suddenly remembered my watch. I looked at it, seven minutes, we were past time. Reluctantly I pushed him away. I pulled up my panties as he protested. I grabbed my shirt from him with a sexy grin.

"Five minutes, that's all you get," I giggled.

"Oh come on, you know you want it," he begged.

"Maybe," I smiled. "But not right now. If you are good, maybe I'll give you my number," I winked at him as I quickly slid the shirt back over me and walked out, leaving him with quite a sizable hardon, from what I could tell.

John really enjoyed the story. That was the last night we fucked each other's brains out. John left me with a suggestion. He said, "I think you are going to find that you will need to expand the game. You'll need to try different venues, not just a bar. Consider what kind of man you'll have to approach, make that part of the game. You'll need to ramp up the excitement, too. No doubt you'll find yourself craving the "humiliation" card.

He was right. The more I played the game, the more humiliation I wanted to add to it. Like I said, it is like a drug to me. So, there I was, approaching the man at the bar. he was probably in his late 50s. He was balding, and had a bit of a beer belly. However, he was well dressed, in a fine tailored suit that suggested upper management at some big company. He was the type of guy who probably still could get a young woman like me, simply with his money. I wasn't that type of girl. I may be a slut, but I'm not a whore, well, at least not a paid one. No, if he was lucky, he'd be getting me for free.

I'd picked this particular guy because it was part of the addition to the game that John had suggested. At home, I'd added a new jar. In it were cards that instructed me on what type of guy to approach, even the type of bar, as I knew most of them in a 20 mile radius, due to the game. On this night I'd picked out the card that said, "older man, at least 50, neighborhood type bar." I tried to challenge myself in this way. I made sure they were the types of guys who would add to my level of humiliation and discomfort. Black men, foreign men, biker types, muscle men, I picked out all my hot buttons. I have had very little experience with these types of men, I knew that I'd be challenged in every possible way before these experiences were over.

I neared the older gentleman. I resisted the temptation of looking at the cards which were in my hand, I noticed they were face up, the writing was visible under my fingers. All I had to do was glance down. I fought the urge. No, this was always better when it was a surprise. That was the challenge that John and I had mapped out. I had to challenge myself, and I couldn't let myself down that way.

I approached him nervously, but with a burning excitement. What would it be tonight? Would it be a kiss on the cheek? Would it be more fondling? Or, would it be one of the more humiliating things I'd thought of to write down. As I approach the men in these games, I always question myself whether or not I can go through with it. Especially now, with more and more embarrassing things to have to do if a humiliation card is selected. No matter, once I commit to it, it's as good as done. The last few steps I managed to shoot a smile in the guy's direction as I marched up to him and smiled.

"Hey there pretty lady," he said with a bit of surprise. "Would you like a drink?"

"Depends," I replied.

"On what?" He asked with interest.

"On whether or not you are willing to play a little game with me."

His look of utter shock was delightful. "What kind of game?" He said with a hint of suspicion.

I realized what it looked like. Again, I was in a tarty outfit. This time I had on a plaid skirt and a very form fitting thin black sweater which accentuated my curves provocatively. It buttoned down the front. I assumed that for a moment he wondered if I was a prostitute. A moment of inspiration hit me. I'd have to add that to the game and make myself pick out a card which described an outfit. Yes, that would be a very humiliating touch for me. The thought got a twinge out of my pussy.

I smiled flirtatiously. "Don't worry, it won't cost you anything," I cooed, "other than a bit of your time."

"Then, I'm all for it. I'm Dan," he said as he stuck out his hand. I was right, he was rich. I could see it in his finely manicured fingernails. He motioned the bartender for a drink for both of us. I started to protest but I saw it was useless, he was used to getting what he wanted, no doubt. I wanted to get right to the game, that was part of the "charm" for me. It was the thrill of the suddenness of it. One second you are complete strangers, the next you might be doing god knows what to him. Good thing for both of us, he bought us shots. I knocked it down and slammed my glass on the bar with purpose. He responded by raising his eyebrow in surprise before downing his own shot.

"There, that's out of the way," I joked. We'd known each other for a couple minutes now. It was far longer than I'd gone with any previous "game player."

I was focused, I was intent on getting on with it. Purposely, I'd made myself wait a few weeks since the last time. John had suggested that too, he knew that denial would heighten it all. He was right, he was always right.

Dan looked at me quizzically. He was watching me fumble with the cards in my hand. For some reason, just the fact that he was looking at me and the cards, made me hesitate. Every time I've done this there is a point where I almost back out. This was that time again. I wondered if I'd waited too long, if it was the right thing to do. But mostly, I think it was because I feared the increasing potential of the humiliation cards, which I knew were now more embarrassing than ever. I had no idea of which one it was, of course, but none were easier than the "fondling" card I'd been forced to do previously.

I took a deep breath. I saw Dan looking at me with concern. Something about the confidence and strength I saw in his eyes convinced me what I was to do.

"Pick a card," I said hastily as I thrust the three cards out to him.

"What's this, a magic trick?" He said smiling.

"Nothing like it, trust me, though, it may be magical...in a different way," I teased.

He hesitated. It was like he was still suspicious. "What's the game all about?" He asked with seriousness. "Why should I play?"

"God," I whined to myself. Even when I had built in humiliation, there were always new ways to embarrass me. I was going to have to convince him to play. Here I was, offering him....who knows what....and I still had to convince him to do it. I'd hoped the hint of sexuality in the whole dealings so far would've lead him to believe it might be in his best interest to do it. But, maybe that was his intention all along, maybe he wanted to exert his own control. He was definitely that type. No doubt he commanded many underlings, I'm sure he was used to being in charge, being the one who made the rules.

"Fine," I thought to myself. "It's just another price I have to play in order to get my humiliation fix that I so crave."

I looked him in the eyes. I could feel his eyes surveying me, penetrating me. I felt like a little girl about to be scolded by the principal. "I have three cards, on each card is something I have to do for you. You pick one, whatever it says, I do. It's simple!" I said as I gave him a shameful smile.

"What if I don't like it?" He wondered.

"You will," I promised him. I thought to myself, "especially if you pick the humiliation card."

"Well, I'm not committing to anything," he laughed.

"You don't have to, sir," I said with an embarrassed look. "It's more about me and what might happen to me," I said.

I think he saw my embarrassment and my weakness and he knew no matter what it was, he'd have the upper hand. He grabbed a card from me quickly. He shoved it into his pocket without looking at it. I protested and tried to grab it. He made a game out of keeping it out of my reach.

"It's mine now," he joked with a confident smile. "I have it and it won't change what's written on it if we wait to read it. In the mean time, have another drink. "

I reluctantly agreed. He was toying with me. He was good. In a way, he was like John. Very controlled, very sure of himself. I felt like his pet sitting there, at the bar. All the while my immediate fate hung in the balance of what was in his pocket. He made me down two more shots with him. This gave him plenty of time to ogle me. I could feel my nipples harden embarrassingly under his gaze. The shots were making me tipsy, I always got hornier when I was tipsy. Maybe he suspected that as well. He was playing his own game.

The anticipation was killing me, I kept sneaking glances at the card which poked out of his suit pocket tantalizingly. I had to go to the bathroom. I think he feared I was trying to "escape." I noticed that he watched me the whole time I walked to the bathroom, I could see him watching me in the bar mirror. There was no escape, really, I'd have to walk past him to get out of the bar anyway.

I was freshening up when it suddenly hit me. Maybe I couldn't tell what card he had in his pocket, but I could tell which ones he didn't have. Nervously, I took out the two cards he hadn't selected. With trepidation, I read the first one. It said, "If you buy me a drink I'll unbutton one button on my sweater. Two, and I'll unbutton two. (There were only three buttons on the sweater, the top one never gets buttoned, it would look too prim).

"Ok," I thought. "That's the medium, risqué one. That means he either has the tame one or...." I shuddered to myself, "...the humiliating one."

My heart was racing as I read the other card. "Do you mind if I sit next to you?" It read. "Oh god," I sighed. He has the "bad" one. I looked at myself in the mirror. My chest was heaving. I was panting. "Fuck," I thought, "look at me, I look like I'm ready to be fucked already." I couldn't help it, this stuff just drove me insane with lust.

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