tagErotic CouplingsBailey's Humiliation Games Ch. 02

Bailey's Humiliation Games Ch. 02


{Continuation of "Bailey's humiliation games. Second story.}

I'm Bailey. If you've read my first story you'll know I'm into sexual humiliation games. The first game I played by myself was the first story where I ended up naked, on my knees in an alley behind a bar, sucking an older man who I'd just met.

It was all because of the game. I had made up three jars at home with index cards. In one jar I had tame, or basic things listed on them. Things such as, "I like your hair," "Can I sit here?" etc. They were simple introductory things which may or may not lead to something. In another jar I had moderate flirty things such as, "Can you see my bra?" (where I'd purposely pre-undone several buttons giving them a good view of my cleavage), or "would you like to see one of my tattoo's?" (both are in places where I'd have to show them some skin and give them a good view of either my breast or the top of my ass.) In the third jar, however, were the daring and humiliating tasks. Like I said, in the last story that "humiliation card" had me naked in an alley, sucking that stranger. I've added a couple of extra touches. Before I go out I also have to decide what type of bar to go to, such as, upscale, local, biker, etc. I then decide what I have to wear on a range from dressed to the nines to completely slutty. Then, I'd decide what kind of guy to target. It could be an older guy, a black guy, a nerd, a fat guy, business man, etc. I decided to make three separate small jars for each of those, that way I had no choice in what humiliations I might have to suffer.

It was awesomely scary and an incredible turn-on at the same time. My ex-boyfriend, an older married man, introduced me to all of this. He made me realize how much I dug the humiliation of being used like that. He was right when he said that when I'd do one thing, it would lead to me craving another, then another.

That brings me to my latest story. It'd been a couple weeks of build up after my last episode. I tried the game again. On the first two attempts, I picked a "tame" card. Neither led to anything, which left me frustrated and even feverish masturbation sessions afterwards didn't slake my thirst for more. On the third attempt I picked a "moderate" card. It read, "I'll buy you a drink if you tell me if you like my bra." Make sure you aren't wearing one." In each of these last three attempts a big part of me was disappointed by not picking the "humiliation card" but my ex boyfriend was right when I'd email him and discuss what I was doing on his secret account he keeps from his wife. He told me that being denied on opportunities would only lead to greater desire and satisfaction when it actually does occur.

The third attempt wasn't a total loss, however. After he ogled my bare tits under my revealing top, per the instructions on the card, it didn't take him long to get the idea he could freely hit on me. I'd decided that if the man I'd picked out was bold enough to pursue me with enough fortitude, then I'd not say no to them if they wanted sex. In this last "moderate" case, I ended up in the backseat of the guy's car. The top was down and he had me, with my legs up high in the air as he pounded my wet pussy. He wasn't bad, but it wasn't everything I needed, which wasn't his fault, per se. I needed the humiliation. I knew it was coming, though, eventually fate would have me pick that card.

So, in lustful trepidation on a Friday night, I nervously took out my jars and began to pick. First, I picked out the type of man. (It was most likely a man, but just for the ultimate humiliation I added "woman" to one lone card in the large jar. I didn't have any experience with women, so this was just another total attempt to humiliate myself. I supposed the woman would just flat reject me anyways.) I picked out the card, it said, "Black guy- athlete type." I gulped. I'd never been with a black guy. I'd fantasized about it before but I'd always preferred white guys. I didn't buy the whole, "black guy with a huge cock/never go back" thing. I thought I might have to find that out firsthand now.

Next, I picked out a location. I picked the card. The card said, "upscale." I had the perfect bar in mind. It was a nightclub downtown with a Latin flavor. It was loud, there were all different ethnic groups and flavors there. Many athletes hung out there, I should have no problem finding the right guy.

Then, my heart fluttered when I started to pick out the card from the "outfit" jar. I realized I could pick any card, including cards requiring me to dress completely slutty and inappropriate for this particular venue. It would just be another layer of humiliation. Luckily, I picked out a card that said, "sexy business woman." I had the perfect outfit for that, which was the reason I'd written the card. I had a blue woman's business suit. The skirt was knee length and I'd added a slit up the sides for a sexier effect. The suit coat was such that when buttoned was a little bit tight, which would cause my cleavage to be pressed together nicely to expose the upper part of my tits nicely. I added one of my nicest bras, a lacy one that they'd be able to peek at, when my boobs were jutting out as they'd be when I was buttoned up. I decided upon a nice pair of calf accenting black high heels. To top off the outfit, I wore some glasses. They remind me of sexy librarian types, the rims are black and thick. I pulled my hair back and tied it up. I giggled when I saw myself dressed as I was. I hoped whoever it was I picked would like the look, but I was sure they would, my tits spilled out nicely in the exposed "V" the top formed.

Then, I got to the business at hand. I was dressed as I was, I knew where I was headed, and I knew the type of guy I had to approach. Now the real business at hand. The action jars. You may wonder how I decided which jar to pick from. Obviously I'd know which was which. Originally, in my first story I'd just blindfolded myself after shuffling them around, then picked from one. My ex, being the logical one, told me to just dump them all together in one big jar and mix them up. I thought, "Duh," and laughed at myself for not thinking of that.

I was shaking noticeably when I picked the card out. I wondered if tonight was the night I'd have to suffer the indignities of the wondrously erotic, "humiliation card." I am not allowed to look at it first, though. I stuffed it in my purse and resisted the temptation to look the entire drive downtown. I passed the keys off to the valet and giggled under my breath as I remembered that one of the cards I'd made up for my jar was to please the valet. "Oh well," I chuckled, "he'll have to wait for another time." Still, the thought of that, and what I might have to do later, had my pussy flowing.

I got inside the club and made my way to the bar. I'd already been offered several drinks (and accepted them) before I mustered the courage to focus on the task at hand. As I've mentioned before, drinking just gets me hornier. I knew I'd have to watch it or I'd find myself being used before I even get to play the game.

I scanned the crowd. I felt a nice buzz coming on. Then, I spotted him. He was in the corner of the other end of the bar. He was sandwiched between two women. He was chatting them up, he was obviously flirting with both of them. I could tell he was a charmer. I'm sure he was a "Player" but that didn't matter. It wasn't as if it mattered in the game. Now, I'd considered already what might happen if I was just boldly rejected. Just because I'd picked a certain guy that fit the profile, didn't mean he didn't have his own choice in the matter. For me, the rule would be, if rejected, pick another guy that fits the profile and do the same. It would only end if at the end of the night, I'd exhausted all possible candidates. I knew that would never happen, though. You offer a guy what I was offering, well, very few will say no.

I waited for an hour, at least, after I spotted him. When he went to dance, so did I. I used several of my bar neighbors for this purpose. They thought they might be getting lucky. They were wrong. I danced near the black guy, just to hope to get his attention. I did, on more than one occasion. I flirted, I smiled and batted my eyelashes. I couldn't tell if he was had any interest, the women he was dancing with were at least as hot as I hoped I was.

Finally, I couldn't stall or wait any longer. When the woman he was now chatting up left to go to the bathroom I got up and approached him. He saw me coming. He ogled me up and down without shame then gave me a wolfish smile. I was nervously smiling. It was as if he had just been waiting for me to approach him. He must have been used to women throwing themselves at him. I now recognized him as one of the local sports figures. He was a football player, a linebacker or something. I'm not good at knowing all that, but later, my ex told me who he was. We introduced ourselves. His name was Trevor. His big hand engulfed mine as we shook. Immediately the thought flashed in my mind about big hands, feet and cock size. I blushed. He leered at me as if he already knew what was on my mind. I felt myself melting in a pool of my own shame and lust.

He immediately snapped me back into the moment, " So, what brings you out tonight, Bailey? What are you into?"

"Oh god," I thought. "If he only knew." But then almost as immediately I thought, in just a few short moments he may know more than he should about that.

Meekly, I reached into my purse and handed him the card. He didn't even have a chance to read it before I saw the woman he'd been talking to return from the bathroom. She appeared furious. I walked away before I got into any confrontation. I resumed my seat at the bar while I saw her arguing with him angrily. I was shaking nervously, probably just as much from the lust as the adrenaline from the near dustup. I watched them going back and forth and I realized I might have picked the wrong guy for the night. I remembered my rule that I must just have to pick another guy. Suddenly, it hit me! "Fuck," I thought. "He has the card, I have no idea what it says." I'd no backup card for this situation. I considered driving back home for another one but it would really be too late by the time I could make it back.

Then, I realized another course of action. I'd just have to get the card back. I saw Trevor finally walk away from the angry woman. I watched her storm off. I didn't know where she'd gone but I needed to act. I rushed up to him.

"Trevor, um, sir, can I have my card back?" I begged. I don't even think he remembered having it with all the previous commotion.

"What? Oh, sure, wait, what is it?"

I didn't want to explain it to him with the possible embarrassment of it all, it was as if I wanted to save all the humiliation for the one that actually gets to act on it. I shuffled nervously, trying to think of the right words. Before I could speak he had the card out and read it as I unsuccessfully tried to grab it from him. He batted me away playfully like I was a child.

His eyes got wide and so did his grin as he finished reading it. "I knew you were a hot thing," he laughed. "I could tell you don't mess around, you get right to the point, I like that as well."

I wanted to tell him he wasn't the one. I glanced around for his female companion. Trevor read my mind. "Oh, don't worry about her, she's just some gold digging bitch that thought she owned me for the night. I set her straight, she won't be back," he smiled. "You aren't some gold digging whore too, are you? This isn't all just some setup, is it? You want Trevor's money?"

I almost laughed when he egotistically referred to himself in the third person but I remembered the game. It appeared he actually was "the one," so I had to act accordingly. I honestly told him, "no, I don't want your money, I don't even know who you are. I just, um, do this for the thrill." "Good, I like thrills too," he smiled lasciviously. "So are you serious?" he asked as he waved the card in front of me.

"Yes," I meekly muttered. I already knew it must be a "humiliation card," he wouldn't be acting the way he was if it was anything else. "I make myself do these things for the excitement," I admitted.

"Come with me," he urged as he took my hand in his big paw. I had no idea what was on the card, I just knew the types of things I'd written. I knew he'd be getting me in some lustfully embarrassing way. I tried to peek at the card he had in his other hand as he basically dragged me through the crowd but I couldn't read it as I was bounced and jostled the whole way.

He took me through some doors, into a private section, the bouncers that were guarding those doors stepped aside as he approached. No doubt this was a common occurrence for Trevor. I was pulled past a number of doors, from behind I heard loud music pumping, giggling and even some moaning. "Must be some of Trevor's friends," I giggled, even as I blushed shamefully at my situation.

He pulled me into a room and closed the door behind him. He locked it quickly. "Now," he huffed, "we won't be disturbed." He pulled me into him and kissed me hard. It was a determined kiss. He was good, he'd obviously done this before. His hands pawed at my top while his mouth devoured my lips, his tongued danced and darted with mine. I wasn't sure whose lust was greater, his or mine. He got frustrated with the buttons of my suit coat since his other hand was on my ass, then under my skirt. He stepped back and with both hands ripped my top open, the buttons went flying.

"There," he huffed impatiently. He went back to kissing me while his free hands now fondled my tits through the lacy bra. He started to pull down on it hard, he was obviously going to rip that off as well. I stopped him ( I kind of liked that bra!). I just unsnapped it from the front and let it fall to our feet. His hands immediately fondled and caressed them while we resumed our lustful kissing. I'd jump and dance from foot to foot each time his strong fingers tugged at my nipples. I'm sure he could feel my excitement each time through our kisses.

"Like that, huh?" he teased. He twisted them harder. My knees got weak, I could smell my own excitement. I started to take off the suit coat which was all that was left on top. He stopped me.

"I've never fucked a white business woman before, leave it on," he urged while still pawing me freely.

I still had no idea what was on the card. I had no way to know what I was about to have to do. It turned me on something fierce.

"Sir, sir," I urged before it went too far. I didn't just want the sex. I wanted what was on the card. I wanted to make sure he made me do whatever humiliating thing I'd written on there. "What am I supposed to do?" I begged meekly.

"Right now, you are supposed to get on your fucking knees and suck my fucking cock," he panted as he tugged my nipples hard one last time, adding to my knee weakened state. I dropped easily in front of him. His cock was out in a flash, it was staring at me angrily and red, dangling from out of the zipper of his designer slacks.

"Mmm," I moaned hungrily as I put my mouth over the tip. He was semi hard, but my mouth almost instantly made his cock jerk and fill with blood.

"Oh yeah, that's it, sl....uh, Bailey, suck that dick," he urged.

I sucked him for a few seconds before pulling off. "It's ok," I admitted with a crimson filled face. "You can call me slut, whore, whatever you wish, sir." I said before taking him in my mouth again with increased desire.

"Fuck yeah, slut," he moaned. "I like that. I knew that behind those clothes was just another cock sucking slut. If you like sucking black cock so much I've got some friends who would just love you," he said.

He was settling into a rhythm. His hands caressed my head. I undid the tie I had in and let my hair fall. He took my hair in his hands and used it to guide me on and off his cock. He began to fuck my mouth like that, like it was just a vehicle to get him off. And truly, that's what I was. I wanted to protest, I wanted to stop him before he shot off in my mouth. I wanted what was on the card, no matter what it was. I couldn't, though. He was too strong, too urgent. He began to spasm. He held my head on him as he filled me. I began to choke on it, the cum was thick and copious. He didn't release his grip until he'd filled me. I fell back on my heels, choking and sputtering. He just collapsed back into a soft recliner and watched me trying to down the rest of his cum. I could see his face had some concern on it.

"Don't worry, sir," I managed to cough out, "I don't mind choking on it...happens all the time," I admitted as my face was hot with shame.

That made him smile. "Damn," he groaned. "You are something else, whore."

That made me giggle a little with pride. "Thank you, sir." I said as I finished swallowing him. Then, I remembered my business. "But Trevor, sir, you were supposed to make me do whatever was on that card," I whined.

"Yeah," he smiled. "About that...."

I was still on my knees. I crawled to him and laid my head on his crotch as he stroked my hair. I used my tongue to bathe his soft member.

"What did the card say?" I asked. "I really wanted to do it tonight," I sighed wistfully.

He grabbed my hair suddenly and made me look at him. "Who said we weren't doing it? He said with a serious look. "Don't worry, you are in it now, I can go all night," he bragged. I could see he wasn't lying. Just from my tongue bath and this new revelation his cock was stirring again.

"Why don't I just show you what it says," he said gruffly. He yanked me over to the sofa roughly.

I still had on my skirt, my heels and my suit coat, though my tits were hanging out since I now had no bra and the coat no longer had buttons. He forced me onto my elbows. I was standing, but bent over my elbows on the sofa, my ass in the air.

"How do you not know what it says?" He asked me.

"I never know," I admitted with shameful lust. "I pick them out random...it could be anything," I said as my pussy stirred lustfully.

"Wow, you really are a kinky slut," he said perhaps disdainfully, but I took it as a compliment.

"Maybe you'll recognize it now then," he laughed. "Don't move," he warned sternly. He pulled up my skirt, then yanked my panties to my ankles as I moaned loudly.

Suddenly, his hand smacked my bare ass forcefully. "Recognize it now?" He chuckled. At the same time he put the card down right in front of my head.

"Oh god," I moaned. Yes, I recognized it. I knew what I was in for now.

He continued the spanking. First, one cheek, then the other. He slapped me hard. It was what the card said. I reread it as he reddened my poor ass. It read, "I want you to spank my ass hard, make it red then I want you to fuck me hard from behind so you can see your handiwork..."

I'd added one last touch but his spanking shook me out of my reading for now. He grabbed my hair again and yanked my hair back roughly.

"Is this what you want, whore? Is it too hard? Or do you want me to fuck that ass up?"

He was making me say it, making me beg. Men just seem to know how much I need that.

"Yes, Trevor, yes. Spank my ass raw. No, it's not too hard. It's as hard as you want. I have no say in it," I managed to squeak out as tears filled my eyes. I could take a lot, I knew that, but this was one big, strong guy. I hoped he could control his own lust.

I glanced back through my tears to see his cock swollen and ready again. He was going to get me again, "good," I thought. My ass was on fire and my pussy was basically flooded now. I could feel the air hitting my wetness down the insides of my thighs. I was almost screaming now with each smack. He was firm and determined. I think he also wanted other people in the halls and in the other rooms to hear how he was using me, too. I knew I wanted that humiliation as well.

Report Story

byLaceAndHumiliation© 4 comments/ 76878 views/ 33 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: